Crosslinking aid, fluorine-containing polymer composition, crosslinked fluorine-containing polymer, molded article, and compound

Abstract

Provided is a crosslinking aid represented by general formula (11). General formula: Z-(Ph-[(CX1X2)m-CY1=CY2Y3]n)2. In the formula, Ph denotes a phenylene group, X1 and X2 each independently denote H, F, OH, a non-fluorinated alkyl group that may have one or more substituent groups, a fluorinated alkyl group that may have one or more substituent groups, a non-fluorinated alkoxy group that may have one or more substituent groups, a fluorinated alkoxy group that may have one or more substituent groups, or a group represented by general formula: -(O)r-(CX1X2)1-CY1=CY2Y3 (in the formula, r is 0 or 1, and l is an integer between 1 and 10), Y1, Y2 and Y3 each independently denote H or F, Z denotes a single bond, -NH-, -NR- (R is an alkyl group having 1-6 carbon atoms), -O-, -S-, -CO-, -SO2-, a non-fluorinated alkylene group that may have one or more substituent groups, or a fluorinated alkylene group that may have one or more substituent groups, instances of m are each independently an integer between 1 and 10, and instances of n are each independently an integer between 1 and 5.

Description

Crosslinking Aid, Fluorine-Containing Polymer Composition, Crosslinked Fluorine-Containing Polymer, Molded Article and Compound

[0001] The present disclosure relates to a crosslinking aid, a fluorine-containing polymer composition, a crosslinked fluorine-containing polymer, a molded article and a compound.

[0002] Patent Document 1 describes a crosslinking agent consisting of a compound represented by the following formula (1). (In formula (1), R １ , R ２ , R ３ are each independently a fluorine atom, an alkyl group, a fluorinated alkyl group, or a substituted or unsubstituted aryl group. Plural R １ may be the same or different. Plural R ２ may be the same or different. Plural R ３ may be the same or different. Provided that at least one of R １ , R ２ , R ３ is a fluorine atom or a group containing a fluorine atom. m is an integer of 2 to 6, and l is an integer of 0 to 2. A hydrogen atom on the benzene ring may be substituted.)

[0003] International Publication No. 2015 / 019581

[0004] An object of the present disclosure is to provide a novel crosslinking aid.

[0005] According to the present disclosure, there is provided a crosslinking aid represented by general formula (11). General formula (11): (In the formula, X １ , X ２ are each independently H, F, OH, a non-fluorinated alkyl group optionally having one or more substituents, a fluorinated alkyl group optionally having one or more substituents, a non-fluorinated alkoxy group optionally having one or more substituents, a fluorinated alkoxy group optionally having one or more substituents, or a group represented by the general formula: -(O) ｒ -(CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ (In the formula, r is 0 or 1, l is an integer of 1 to 10), Y１ , Y ２ , Y ３ Independently, H or F, Z is a single bond, -NH-, -NR- (R is an alkyl group with 1 to 6 carbon atoms), -O-, -S-, -CO-, -SO ２ - A non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents, where m is an integer from 1 to 10 independently, and n is an integer from 1 to 5 independently. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.

[0006] This disclosure provides a novel crosslinking aid.

[0007] The following describes specific embodiments of this disclosure in detail, but this disclosure is not limited to the embodiments described below.

[0008] Conventionally, when crosslinking fluorine-containing elastomers by peroxide crosslinking, a technique using crosslinking aids is known. A typical compound used as a crosslinking aid is triallyl isocyanurate (TAIC).

[0009] Patent Document 1 states that triallyl isocyanurate (TAIC) was generally well known as a crosslinking aid, but that there was a need for a novel crosslinking agent that could further improve the heat resistance and steam resistance of crosslinked fluoroelastomers. To solve this problem, it is proposed to use a crosslinking agent consisting of the above-mentioned compounds as a crosslinking aid (crosslinking agent).

[0010] This disclosure provides a crosslinking aid that can produce molded articles with even greater heat resistance than those obtained by crosslinking a fluorine-containing elastomer using triallyl isocyanurate (TAIC), and moreover, molded articles with even greater crosslinkability than those obtained by crosslinking a fluorine-containing elastomer using the crosslinking aid (crosslinking agent) described in Patent Document 1.

[0011] 1. The first crosslinking aid The crosslinking aid of this disclosure is the crosslinking aid represented by general formula (11) (which may be referred to as the "first crosslinking aid" in this disclosure). General formula (11):

[0012] Since the first crosslinking aid has the above-described structure, it can be suitably used as a crosslinking aid when crosslinking a fluorine-containing elastomer by peroxide crosslinking. By using the first crosslinking aid, it is possible to obtain a molded product with superior heat resistance compared to a molded product obtained by crosslinking a fluorine-containing elastomer by peroxide crosslinking using triallyl isocyanurate (TAIC), and moreover, a molded product with even better crosslinkability than a molded product obtained by crosslinking a fluorine-containing elastomer using the crosslinking aid (crosslinking agent) described in Patent Document 1.

[0013] In general formula (11), X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ This is the base represented by (wherein r is 0 or 1, and l is an integer from 1 to 10).

[0014] In this disclosure, unless otherwise specified, “substituent” means a substituteable group. Examples of such “substituent” are aliphatic groups, aromatic groups, heterocyclic groups, acyl groups, acyloxy groups, acylamino groups, aliphatic oxy groups, aromatic oxy groups, heterocyclic oxy groups, aliphatic oxycarbonyl groups, aromatic oxycarbonyl groups, heterocyclic oxycarbonyl groups, carbamoyl groups, aliphatic sulfonyl groups, aromatic sulfonyl groups, heterocyclic sulfonyl groups, aliphatic sulfonyloxy groups, aromatic sulfonyloxy groups, heterocyclic sulfonyloxy groups, sulfamoyl groups, aliphatic sulfonamide groups, aromatic sulfonamide groups, heterocyclic sulfonamide groups, amino groups, aliphatic amino This includes a no group, an aromatic amino group, a heterocyclic amino group, an aliphatic oxycarbonylamino group, an aromatic oxycarbonylamino group, a heterocyclic oxycarbonylamino group, an aliphatic sulfinyl group, an aromatic sulfinyl group, an aliphatic thio group, an aromatic thio group, a hydroxy group, a cyano group, a sulfo group, a carboxyl group, an aliphatic oxyamino group, an aromatic oxyamino group, a carbamoylamino group, a sulfamoylamino group, a halogen atom, a sulfamoylcarbamoyl group, a carbamoylsulfamoyl group, a dialiphatic oxyphosphinyl group, or a diaromatic oxyphosphinyl group.

[0015] X １ and X ２ The non-fluorinated alkyl group may be a non-fluorinated alkyl group having 1 to 20 carbon atoms, a non-fluorinated alkyl group having 1 to 10 carbon atoms, a non-fluorinated alkyl group having 1 to 5 carbon atoms, or a non-fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ３ , -C ２ H ５ , -C ３ H ７ These are some examples.

[0016] X １ and X ２ The fluorinated alkyl group may be a partially fluorinated alkyl group or a saturated fluorinated alkyl group. １ and X ２The fluorinated alkyl group may be a fluorinated alkyl group having 1 to 20 carbon atoms, a fluorinated alkyl group having 1 to 10 carbon atoms, a fluorinated alkyl group having 1 to 5 carbon atoms, or a fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ２ F, -CHF ２ , -CF ３ , -C ２ F ５ , -C ３ F ７ These are some examples.

[0017] X １ and X ２ The non-fluorinated alkoxy group may be a non-fluorinated alkoxy group having 1 to 20 carbon atoms, a non-fluorinated alkoxy group having 1 to 10 carbon atoms, a non-fluorinated alkoxy group having 1 to 5 carbon atoms, or a non-fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ３ , -OC ２ H ５ , -OC ３ H ７ These are some examples.

[0018] X １ and X ２ The fluorinated alkoxy group may be a partially fluorinated alkoxy group or a saturated fluorinated alkoxy group. １ and X ２ The fluorinated alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, a fluorinated alkoxy group having 1 to 10 carbon atoms, a fluorinated alkoxy group having 1 to 5 carbon atoms, or a fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ２ F, -OCHF ２ , -OCF ３ , -OC ２ F ５ , -OC ３ F ７ These are some examples.

[0019] Also, X １ and X ２ The general formula is: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y３ may be a group represented by (wherein r is 0 or 1, and l is an integer of 1 to 10). l is independently an integer of 1 to 10, and may be an integer of 1 to 8, an integer of 1 to 6, an integer of 1 to 4, or an integer of 1 to 3. X in this general formula １ and X ２ are as described above. In addition, Y in this general formula １ , Y ２ and Y ３ are as described below.

[0020] In general formula (11), Y １ , Y ２ , Y ３ are each independently H or F.

[0021] In general formula (11), Z is a single bond, -NH-, -NR- (R is an alkyl group having 1 to 6 carbon atoms), -O-, -S-, -CO-, -SO ２ -, a non-fluorinated alkylene group optionally having one or more substituents, or a fluorinated alkylene group optionally having one or more substituents. Z is preferably a single bond or a fluorinated alkylene group optionally having one or more substituents.

[0022] The non-fluorinated alkylene group for Z may be a non-fluorinated alkylene group having 1 to 20 carbon atoms, a non-fluorinated alkylene group having 1 to 10 carbon atoms, or a non-fluorinated alkylene group having 1 to 8 carbon atoms, for example, -(CH ２ ) ｓ -(s is an integer of 1 to 10), and the like. s is an integer of 1 to 10, may be an integer of 1 to 8, and may be an integer of 2 to 10 or an integer of 2 to 8.

[0023] The fluorinated alkylene group for Z may be a partially fluorinated alkylene group or a fully fluorinated alkylene group. The fluorinated alkylene group for Z may be a fluorinated alkylene group having 1 to 20 carbon atoms, a fluorinated alkylene group having 1 to 10 carbon atoms, or a fluorinated alkylene group having 1 to 8 carbon atoms, for example, -C(CF ３ ) ２ -, -(CF ２ ) ｓ- and the like. s is an integer of 1 to 10, may be an integer of 1 to 8, and may be an integer of 2 to 10 or an integer of 2 to 8.

[0024] Further, X １ , X ２ , Y １ , Y ２ , Y ３ and at least one of Z also preferably contains one or more fluorine atoms. The use of a crosslinking aid having such a configuration tends to provide a molded article that is further excellent in heat resistance. The crosslinking aid is X １ , X ２ , Y １ , Y ２ , Y ３ and Z having a fluorine atom or a functional group containing a fluorine atom has advantages that, for example, when the crosslinking aid is mixed with a fluorine-containing polymer, the affinity between the crosslinking aid and the fluorine-containing polymer is improved and mixing is facilitated. Further, the crosslinking aid is X １ , X ２ , Y １ , Y ２ , Y ３ and Z having a fluorine atom or a functional group containing a fluorine atom, for example, when a molded article is produced by crosslinking a composition containing a crosslinking aid and a fluorine-containing polymer, the electron density of a benzene ring introduced into the crosslinked structure of the molded article is reduced, and the oxidation resistance of the molded article is improved.

[0025] In general formula (11), each m is independently an integer of 1 to 10, and may be an integer of 1 to 8, an integer of 1 to 6, an integer of 1 to 4, or an integer of 1 to 3, or may be an integer of 2 to 10, an integer of 2 to 8, an integer of 2 to 6, an integer of 2 to 4, or an integer of 2 to 3.

[0026] In general formula (11), each n is independently an integer of 1 to 5. n may be 1 or 2, and may be 1.

[0027] In general formula (11), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0028] In one embodiment, the crosslinking aid of the present disclosure is represented by general formula (12). General formula (12):

[0029] In general formula (12), X １ , X ２ These are independently H or F, preferably both being F.

[0030] In general formula (12), Z is a single bond or a fluorinated alkylene group which may have one or more substituents.

[0031] The fluorinated alkylene group of Z may be a partially fluorinated alkylene group or a saturated fluorinated alkylene group. The fluorinated alkylene group of Z may be a fluorinated alkylene group having 1 to 20 carbon atoms, a fluorinated alkylene group having 1 to 10 carbon atoms, or a fluorinated alkylene group having 1 to 8 carbon atoms, for example, -C(CF ３ ) ２ -, - (CF ２ ) ｓ - are some examples. s is an integer between 1 and 10, may be an integer between 1 and 8, or may be an integer between 2 and 10 or an integer between 2 and 8.

[0032] In general formula (12), m is independently an integer between 1 and 10, which may be an integer between 1 and 8, an integer between 1 and 6, or an integer between 1 and 4, which may be an integer between 2 and 6, or an integer between 2 and 4.

[0033] In general formula (12), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0034] In one embodiment, the crosslinking aid of the present disclosure is represented by general formula (13). General formula (13):

[0035] In general formula (13), X １ , X ２ These are independently H or F.

[0036] In general formula (13), X ３ These are independently OH, a nonfluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｋ -CH=CH ２ This is the base represented by (wherein r is 0 or 1, and k is an integer from 1 to 10).

[0037] X ３The non-fluorinated alkoxy group may be a non-fluorinated alkoxy group having 1 to 20 carbon atoms, a non-fluorinated alkoxy group having 1 to 10 carbon atoms, a non-fluorinated alkoxy group having 1 to 5 carbon atoms, or a non-fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ３ , -OC ２ H ５ , -OC ３ H ７ These are some examples.

[0038] X ３ The general formula is: -(O) ｒ - (CX １ X ２ ) ｋ -CH=CH ２ The base may also be represented by (wherein r is 0 or 1, and k is an integer from 1 to 10). １ and X ２ k is independently H or F. k is independently an integer from 1 to 10, and may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3. In one embodiment, X ３ is -O-CH ２ -CH=CH ２ It is the group shown by .

[0039] In general formula (13), X ４ Independently, the general formula is: -(CX １ X ２ ) ｌ -CH=CH ２ The group is represented by X. １ and X ２ l is independently H or F. l is independently an integer from 1 to 10, and may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3. In one embodiment, X ４ is, -CH ２ -CH=CH ２ It is the group shown by .

[0040] In general formula (13), Z is a single bond or a fluorinated alkylene group which may have one or more substituents.

[0041] The fluorinated alkylene group of Z may be a partially fluorinated alkylene group or a saturated fluorinated alkylene group. The fluorinated alkylene group of Z may be a fluorinated alkylene group having 1 to 20 carbon atoms, a fluorinated alkylene group having 1 to 10 carbon atoms, or a fluorinated alkylene group having 1 to 8 carbon atoms, for example, -C(CF ３ ) ２ -, - (CF ２ ) ｓ - are some examples. s is an integer between 1 and 10, may be an integer between 1 and 8, or may be an integer between 2 and 10 or an integer between 2 and 8.

[0042] In general formula (13), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3, which may be 1 or 2, which may be 2.

[0043] In general formula (13), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C6 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0044] The first crosslinking aid includes a novel compound, as will be described later. A method for producing the novel compound that can be used as the first crosslinking aid will be described later.

[0045] 2. Second Crosslinking Aid The crosslinking aid of this disclosure is the crosslinking aid represented by general formula (21) (which may be referred to as the "second crosslinking aid" in this disclosure). General formula (21):

[0046] Since the second crosslinking aid has the above-described structure, it can be suitably used as a crosslinking aid when crosslinking a fluorine-containing elastomer by peroxide crosslinking. By using the second crosslinking aid, it is possible to obtain a molded product with superior heat resistance compared to a molded product obtained by crosslinking a fluorine-containing elastomer by peroxide crosslinking using triallyl isocyanurate (TAIC), and moreover, a molded product with even better crosslinkability than a molded product obtained by crosslinking a fluorine-containing elastomer using the crosslinking aid (crosslinking agent) described in Patent Document 1.

[0047] In general formula (21), X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ This is the base represented by (wherein r is 0 or 1, and l is an integer from 1 to 10).

[0048] X １ and X ２ The non-fluorinated alkyl group may be a non-fluorinated alkyl group having 1 to 20 carbon atoms, a non-fluorinated alkyl group having 1 to 10 carbon atoms, a non-fluorinated alkyl group having 1 to 5 carbon atoms, or a non-fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ３ , -C ２ H ５ , -C ３ H ７ These are some examples.

[0049] X１ and X ２ The fluorinated alkyl group may be a partially fluorinated alkyl group or a saturated fluorinated alkyl group. １ and X ２ The fluorinated alkyl group may be a fluorinated alkyl group having 1 to 20 carbon atoms, a fluorinated alkyl group having 1 to 10 carbon atoms, a fluorinated alkyl group having 1 to 5 carbon atoms, or a fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ２ F, -CHF ２ , -CF ３ , -C ２ F ５ , -C ３ F ７ These are some examples.

[0050] X １ and X ２ The non-fluorinated alkoxy group may be a non-fluorinated alkoxy group having 1 to 20 carbon atoms, a non-fluorinated alkoxy group having 1 to 10 carbon atoms, a non-fluorinated alkoxy group having 1 to 5 carbon atoms, or a non-fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ３ , -OC ２ H ５ , -OC ３ H ７ These are some examples.

[0051] X １ and X ２ The fluorinated alkoxy group may be a partially fluorinated alkoxy group or a saturated fluorinated alkoxy group. １ and X ２ The fluorinated alkoxy group may be a fluorinated alkoxy group having 1 to 20 carbon atoms, a fluorinated alkoxy group having 1 to 10 carbon atoms, a fluorinated alkoxy group having 1 to 5 carbon atoms, or a fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ２ F, -OCHF ２ , -OCF ３ , -OC ２ F ５ , -OC ３ F ７ These are some examples.

[0052] Also, X １ and X ２The general formula is: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ The base may be represented by (wherein r is 0 or 1, and l is an integer from 1 to 10). l is independently an integer from 1 to 10, and may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3. In this general formula, X １ and X ２ Regarding this, it is as stated above. Also, Y in this general formula １ , Y ２ and Y ３ The details are as follows:

[0053] In general formula (21), Y １ , Y ２ , Y ３ These are independently H or F.

[0054] Also, X １ , X ２ , Y １ , Y ２ and Y ３ It is also preferable that at least one of the components contains one or more fluorine atoms. Using a crosslinking aid having such a configuration tends to result in a molded product with even better heat resistance. The crosslinking aid is X １ , X ２ , Y １ , Y ２ and Y ３ As such, by having a fluorine atom or a functional group containing a fluorine atom, for example, when a crosslinking aid is mixed with a fluorine-containing polymer, the affinity between the crosslinking aid and the fluorine-containing polymer is improved, which has the advantage of making mixing easier. Also, if the crosslinking aid is X １ , X ２ , Y １ , Y ２ and Y ３For example, by having a fluorine atom or a functional group containing a fluorine atom, when a molded article is produced by crosslinking a composition containing a crosslinking aid and a fluorine-containing polymer, the electron density of the benzene ring introduced into the crosslinked structure of the molded article decreases, and the oxidation resistance of the molded article is improved.

[0055] In general formula (21), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3, which may be 1 or 2, which may be 2.

[0056] In general formula (21), Z １ is a benzene ring, N or CX'. X' is OH, F or H, and therefore Z １ It is a benzene ring, N, COH, CF, or CH.

[0057] In general formula (21), p is either 0 or 1. In the crosslinking aid represented by general formula (21), the molecule contains the general formula: There are q groups represented by .

[0058] Z １ When is a benzene ring, in general formula (21), q represents the number of the above-mentioned groups bonded to the benzene ring. In general formula (21), q is an integer from 2 to 6, and may be 2 or 3.

[0059] In general formula (21), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0060] Z １ If is a benzene ring, then in general formula (21), in q of the group, p is either all 0 or all 1.

[0061] Z １ If is N or CX', then in general formula (21), q is 3. Also, Z １ If is N or CX', then all p are 1. That is, Z １ When is N or CX', in the crosslinking aid represented by general formula (21), the molecule contains general formula: There are three groups represented by this symbol, all of which are bonded to the N, COH, CF, or N or C of CH.

[0062] In one embodiment, the crosslinking aid of the present disclosure is represented by general formula (22). General formula (22):

[0063] In general formula (22), X １ , X ２ These are independently H or F.

[0064] In general formula (22), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3, which may be 1 or 2, which may be 2.

[0065] In general formula (22), p is either 0 or 1. In the crosslinking aid represented by general formula (22), the molecule contains the general formula: There are q groups represented by . In general formula (22), in q of these groups, p is either all 0 or all 1.

[0066] In general formula (22), q represents the number of the above-mentioned groups bonded to the benzene ring. In general formula (22), q is an integer from 2 to 6, and may be 2 or 3.

[0067] In general formula (22), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0068] In one embodiment, the crosslinking aid represented by general formula (22) is the following compound. (In the formula, the number (4) at the end represents the number of groups bonded to the benzene ring. It is preferable that four groups are bonded to positions 1, 2, 4, and 5 of the benzene ring.)

[0069] In one embodiment, the crosslinking aid of the present disclosure is represented by general formula (23). General formula (23):

[0070] In general formula (23), X １ , X ２ These are independently H or F.

[0071] In general formula (23), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3, which may be 1 or 2, which may be 2.

[0072] In general formula (23), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0073] In one embodiment, the crosslinking aid of the present disclosure is represented by general formula (24). General formula (24):

[0074] In general formula (24), X １ , X ２ X' is independently H or F, and X' is OH, F, or H.

[0075] In general formula (24), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3, which may be 1 or 2, which may be 2.

[0076] In general formula (24), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0077] 3. Third Crosslinking Aid The crosslinking aid of this disclosure is the crosslinking aid represented by general formula (31) (which may be referred to as the "third crosslinking aid" in this disclosure). General formula (31):

[0078] Since the third crosslinking aid has the above-described structure, it can be suitably used as a crosslinking aid when crosslinking a fluorine-containing elastomer by peroxide crosslinking. By using the third crosslinking aid, it is possible to obtain a molded product with superior heat resistance compared to a molded product obtained by crosslinking a fluorine-containing elastomer by peroxide crosslinking using triallyl isocyanurate (TAIC), and moreover, a molded product with even better crosslinkability than a molded product obtained by crosslinking a fluorine-containing elastomer using the crosslinking aid (crosslinking agent) described in Patent Document 1.

[0079] In general formula (31), X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ This is the base represented by (wherein r is 0 or 1, and l is an integer from 1 to 10). １ and X ２ H is preferred.

[0080] X １ and X ２ The non-fluorinated alkyl group may be a non-fluorinated alkyl group having 1 to 20 carbon atoms, a non-fluorinated alkyl group having 1 to 10 carbon atoms, a non-fluorinated alkyl group having 1 to 5 carbon atoms, or a non-fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ３ , -C ２ H ５ , -C ３ H ７ These are some examples.

[0081] X １ and X ２ The fluorinated alkyl group may be a partially fluorinated alkyl group or a saturated fluorinated alkyl group. １ and X ２ The fluorinated alkyl group may be a fluorinated alkyl group having 1 to 20 carbon atoms, a fluorinated alkyl group having 1 to 10 carbon atoms, a fluorinated alkyl group having 1 to 5 carbon atoms, or a fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ２ F, -CHF ２ , -CF ３ , -C ２ F ５ , -C ３ F ７ These are some examples.

[0082] X１ and X ２ The non-fluorinated alkoxy group may be a non-fluorinated alkoxy group having 1 to 20 carbon atoms, a non-fluorinated alkoxy group having 1 to 10 carbon atoms, a non-fluorinated alkoxy group having 1 to 5 carbon atoms, or a non-fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ３ , -OC ２ H ５ , -OC ３ H ７ These are some examples.

[0083] X １ and X ２ The fluorinated alkoxy group may be a partially fluorinated alkoxy group or a saturated fluorinated alkoxy group. １ and X ２ The fluorinated alkoxy group may be a fluorinated alkoxy group having 1 to 20 carbon atoms, a fluorinated alkoxy group having 1 to 10 carbon atoms, a fluorinated alkoxy group having 1 to 5 carbon atoms, or a fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ２ F, -OCHF ２ , -OCF ３ , -OC ２ F ５ , -OC ３ F ７ These are some examples.

[0084] Also, X １ and X ２ The general formula is: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ The base may be represented by (wherein r is 0 or 1, and l is an integer from 1 to 10). l is independently an integer from 1 to 10, and may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3. In this general formula, X １ and X ２ Regarding this, it is as stated above. Also, Y in this general formula １ , Y ２ and Y ３ The details are as follows:

[0085] In general formula (31), Y １ , Y ２ , Y ３ Y is independently either H or F. １ and Y ２ H is preferred.

[0086] In general formula (31), Z is a single bond, -NH-, -NR- (R is an alkyl group having 1 to 6 carbon atoms), -O-, -S-, -CO-, -SO ２ - is a non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents. A fluorinated alkylene group which may have one or more substituents is preferred for Z.

[0087] The non-fluorinated alkylene group of Z may be a non-fluorinated alkylene group having 1 to 20 carbon atoms, a non-fluorinated alkylene group having 1 to 10 carbon atoms, or a non-fluorinated alkylene group having 1 to 8 carbon atoms, for example, -(CH ２ ) ｓ Examples include -(s is an integer from 1 to 10). s is an integer from 1 to 10, may be an integer from 1 to 8, or may be an integer from 2 to 10 or an integer from 2 to 8.

[0088] The fluorinated alkylene group of Z may be a partially fluorinated alkylene group or a saturated fluorinated alkylene group. The fluorinated alkylene group of Z may be a fluorinated alkylene group having 1 to 20 carbon atoms, a fluorinated alkylene group having 1 to 10 carbon atoms, or a fluorinated alkylene group having 1 to 8 carbon atoms, for example, -C(CF ３ ) ２ -, - (CF ２ ) ｓ - are some examples. s is an integer between 1 and 10, may be an integer between 1 and 8, or may be an integer between 2 and 10 or an integer between 2 and 8.

[0089] In general formula (31), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be 1 or 2, which may be 1.

[0090] In general formula (31), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0091] In one embodiment, the crosslinking aid of the present disclosure is represented by general formula (32). General formula (32):

[0092] In general formula (32), X １ , X ２ X is independently either H or F. １ and X ２ H is preferred.

[0093] In general formula (32), Z is a single bond or a fluorinated alkylene group which may have one or more substituents. A fluorinated alkylene group which may have one or more substituents is preferred as Z.

[0094] The fluorinated alkylene group of Z may be a partially fluorinated alkylene group or a saturated fluorinated alkylene group. The fluorinated alkylene group of Z may be a fluorinated alkylene group having 1 to 20 carbon atoms, a fluorinated alkylene group having 1 to 10 carbon atoms, or a fluorinated alkylene group having 1 to 8 carbon atoms, for example, -C(CF ３ ) ２ -, - (CF ２ ) ｓ- are some examples. s is an integer between 1 and 10, may be an integer between 1 and 8, or may be an integer between 2 and 10 or an integer between 2 and 8.

[0095] In general formula (32), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be 1 or 2, which may be 1.

[0096] In general formula (32), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0097] 4. Compositions Furthermore, the present disclosure provides compositions containing the above-mentioned crosslinking aid and fluorine-containing polymer.

[0098] The amount of crosslinking aid in the composition is preferably 0.1 parts by mass or more, more preferably 0.5 parts by mass or more, and even more preferably 1.0 part by mass or more, per 100 parts by mass of the fluorine-containing polymer, in order to improve the sealing properties of the molded product. Furthermore, the amount of crosslinking aid in the composition is preferably 20 parts by mass or less, and more preferably 10 parts by mass or less, per 100 parts by mass of the fluorine-containing polymer, in order to improve the mechanical properties of the molded product.

[0099] As a fluorine-containing polymer, fluorine-containing elastomers are preferred because they have excellent sealing properties, chemical resistance, and heat resistance.

[0100] In this disclosure, "fluorine-containing elastomer" refers to an amorphous fluorine-containing polymer. "Amorphous" means that the magnitude of the melting peak (ΔH) observed in differential scanning calorimetry (DSC) (heating rate 10°C / min) or differential thermal analysis (DTA) (heating rate 10°C / min) of the fluorine-containing polymer is 4.5 J / g or less. Fluorine-containing elastomers exhibit elastomer properties by crosslinking. Elastomer properties refer to the ability of a polymer to be stretched and to retain its original length when the force required to stretch the polymer is no longer applied.

[0101] The fluorine-containing elastomer may be a partially fluorinated elastomer or a perfluoroelastomer, but it is preferable to use a perfluoroelastomer because it has even better chemical resistance and heat resistance.

[0102] In this disclosure, a partially fluorinated elastomer is a fluorinated polymer containing fluoromonomer units, wherein the content of perfluoromonomer units relative to the total monomer units is less than 90 mol%, and which has a glass transition temperature of 20°C or lower and a melting peak (ΔH) of 4.5 J / g or lower.

[0103] In this disclosure, a perfluoroelastomer is a fluorine-containing polymer having a perfluoromonomer unit content of 90 mol% or more, preferably 91 mol% or more, relative to the total monomer units, having a glass transition temperature of 20°C or less, and having a melting peak (ΔH) of 4.5 J / g or less, and further having a fluorine atom concentration of 71% by mass or more, preferably 71.5% by mass or more. In this disclosure, the concentration of fluorine atoms contained in the fluorine-containing polymer is calculated from the type and content of each monomer constituting the fluorine-containing polymer.

[0104] In this disclosure, a perfluoromonomer is a monomer that does not contain carbon-hydrogen atom bonds in its molecule. The perfluoromonomer may be a monomer in which some of the fluorine atoms bonded to the carbon atoms are replaced with chlorine atoms, or it may have nitrogen atoms, oxygen atoms, sulfur atoms, phosphorus atoms, boron atoms, or silicon atoms in addition to carbon atoms. Preferably, the perfluoromonomer is a monomer in which all hydrogen atoms are replaced with fluorine atoms. The perfluoromonomer does not contain monomers that provide crosslinking sites.

[0105] Examples of the partially fluorinated elastomers mentioned above include vinylidene fluoride (VdF)-based fluororubber, tetrafluoroethylene (TFE) / propylene (Pr)-based fluororubber, tetrafluoroethylene (TFE) / propylene / vinylidene fluoride (VdF)-based fluororubber, ethylene / hexafluoropropylene (HFP)-based fluororubber, ethylene / hexafluoropropylene (HFP) / vinylidene fluoride (VdF)-based fluororubber, and ethylene / hexafluoropropylene (HFP) / tetrafluoroethylene (TFE)-based fluororubber. Among these, it is preferable that at least one is selected from the group consisting of vinylidene fluoride-based fluororubber and tetrafluoroethylene / propylene-based fluororubber.

[0106] In this disclosure, the content of each monomer constituting the fluorine-containing polymer can be calculated by appropriately combining NMR, FT-IR, elemental analysis, and X-ray fluorescence analysis depending on the type of monomer.

[0107] The fluorine-containing elastomer described above may also be a perfluoroelastomer. Examples of the perfluoroelastomer include perfluoroelastomers containing TFE, such as TFE / fluoroalkyl vinyl ether copolymers.

[0108] The above fluoroalkyl vinyl ether is: General formula (3): CF ２ =CF - ORf ３ (wherein, Rf ３) represents a perfluoroalkyl group having 1 to 8 carbon atoms. Fluoromers represented by the general formula (4): CF ２ = CFOCF ２ ORf ４ (wherein, Rf ４ Fluoromers represented by (where C1-C6 is a linear or branched perfluoroalkyl group, C5-C6 is a cyclic perfluoroalkyl group, or C2-C6 is a linear or branched perfluorooxyalkyl group containing 1-3 oxygen atoms), and General formula (5): CF ２ = CFO (CF ２ CF(Y ５ )O) ｍ (CF ２ ) ｎ F (wherein, Y ５ represents a fluorine atom or a trifluoromethyl group. m is an integer from 1 to 4. n is an integer from 1 to 4. Preferably, it is at least one selected from the group consisting of fluoromonomers represented by ), and more preferably a fluoromonomer represented by general formula (3).

[0109] As perfluoroelastomers, at least one selected from the group consisting of TFE / fluoromonomer copolymers represented by general formula (3), (4), or (5), and fluoromonomer / monomer copolymers that provide crosslinking sites represented by TFE / general formula (3), (4), or (5) is preferred.

[0110] The composition, in the case of a TFE / perfluoromethyl vinyl ether (PMVE) copolymer, is preferably 45-90 / 10-55 (mol%), more preferably 55-80 / 20-45, and even more preferably 55-70 / 30-45.

[0111] In the case of a TFE / PMVE / monomer copolymer that provides a crosslinking site, the preferred values ​​are 45-89.9 / 10-54.9 / 0.01-4 (mol%), more preferably 50-77.9 / 20-49.9 / 0.1-3.5, and even more preferably 55-69.8 / 30-44.8 / 0.2-3.

[0112] In the case of a fluoromonomer copolymer represented by general formula (3), (4), or (5) with 4 to 12 carbon atoms, the ratio is preferably 50 to 90 / 10 to 50 (mol%), more preferably 60 to 88 / 12 to 40, and even more preferably 65 to 85 / 15 to 35.

[0113] In the case of a TFE / fluoromonomer represented by general formula (3), (4), or (5) with 4 to 12 carbon atoms / monomer copolymer that provides a crosslinking site, the preferred range is 50 to 89.9 / 10 to 49.9 / 0.01 to 4 (mol%), more preferably 60 to 87.9 / 12 to 39.9 / 0.1 to 3.5, and even more preferably 65 to 84.8 / 15 to 34.8 / 0.2 to 3. Outside these composition ranges, the properties as a rubber elastic material are lost, and the material tends to have properties closer to those of a resin.

[0114] The perfluoroelastomer is preferably at least one selected from the group consisting of TFE / fluoromonomer represented by general formula (5) / monomer copolymer that provides a crosslinking site, TFE / fluoromonomer copolymer represented by general formula (5), TFE / fluoromonomer copolymer represented by general formula (3), and TFE / fluoromonomer / monomer copolymer that provides a crosslinking site.

[0115] Examples of the above-mentioned perfluoroelastomers include those described in International Publication No. 97 / 24381, Japanese Patent Publication No. 61-57324, Japanese Patent Publication No. 4-81608, Japanese Patent Publication No. 5-13961, etc.

[0116] A monomer that provides crosslinking sites is a monomer (curesite monomer) that has crosslinkable groups that provide crosslinking sites to a fluoropolymer for crosslinking by a crosslinking agent.

[0117] The monomer that provides the crosslinking site is General formula (6): CX ６ ２ = CX ６ -Rf ６ CHR ６ X ７ (In the formula, X ６These are the same or different hydrogen atoms, fluorine atoms, or CH ３ , Rf ６ is a fluoroalkylene group, a perfluoroalkylene group, a fluoro(poly)oxyalkylene group or a perfluoro(poly)oxyalkylene group, R ６ is a hydrogen atom or CH ３ , X ７ Fluoromers represented by the general formula (7): CX (where is an iodine atom or a bromine atom) ６ ２ = CX ６ -Rf ７ X ７ (In the formula, X ６ These are the same or different hydrogen atoms, fluorine atoms, or CH ３ , Rf ７ X is a fluoroalkylene group, a perfluoroalkylene group, a fluoro(poly)oxyalkylene group, or a perfluoro(poly)oxyalkylene group. ７ Fluoromers represented by (where is an iodine atom or a bromine atom), general formula (8): CF ２ = CFO (CF ２ CF (CF ３ )O) ｍ (CF ２ ) ｎ -X ８ (In the formula, m is an integer from 0 to 5, n is an integer from 1 to 3, X ８ This includes cyano groups, carboxyl groups, alkoxycarbonyl groups, iodine atoms, bromine atoms, or -CH ２ Fluoromer represented by I, general formula (9): CH ２ = CFCF ２ O(CF(CF ３ ) CF ２ O) ｍ (CF(CF ３ )) ｎ -X ９ (In the formula, m is an integer from 0 to 5, n is an integer from 1 to 3, X ９ This includes cyano groups, carboxyl groups, alkoxycarbonyl groups, iodine atoms, bromine atoms, or CH ２ Fluoromers represented by OH, and general formula (10): CR １０２ =CR １０ -Z-CR １０ =CR １０ ２ (In the formula, R １０ is the same or different hydrogen atom or a C1-C5 alkyl group. Z is a linear or branched alkylene group having an oxygen atom, having C1-C18, a cycloalkylene group having C3-C18, a C1-C10 alkylene group or oxyalkylene group that is at least partially fluorinated, or -(Q) ｐ -CF ２ O-(CF ２ CF ２ O) ｍ (CF ２ O) ｎ -CF ２ - (Q) ｐ It is preferable that the monomer is at least one selected from the group consisting of monomers represented by - (wherein Q is an alkylene group or an oxyalkylene group, p is 0 or 1, and m / n is 0.2 to 5) and has a molecular weight of 500 to 10000.

[0118] X ６ It is preferably a fluorine atom. Rf ６ and Rf ７ It is preferable that the group is a perfluoroalkylene group having 1 to 5 carbon atoms. ６ It is preferably a hydrogen atom. ８ This is a cyano group, an alkoxycarbonyl group, an iodine atom, a bromine atom, or -CH ２ I is preferable. ９ This is a cyano group, an alkoxycarbonyl group, an iodine atom, a bromine atom, or -CH ２ It is preferable that it be OH.

[0119] As monomers that provide crosslinking sites, CF ２ = CFOCF ２ CF (CF ３ ) OCF ２ CF ２ CN, CF ２ = CFOCF ２ CF (CF３ ) OCF ２ CF ２ COOH, CF ２ = CFOCF ２ CF (CF ３ ) OCF ２ CF ２ CH ２ I, CF ２ = CFOCF ２ CF ２ CH ２ I, CH ２ = CFCF ２ OCF (CF ３ ) CF ２ OCF (CF ３ ) CN, CH ２ = CFCF ２ OCF (CF ３ ) CF ２ OCF (CF ３ ) COOH, CH ２ = CFCF ２ OCF (CF ３ ) CF ２ OCF (CF ３ )CH ２ OH, CH ２ =CHCF ２ CF ２ I, CH ２ =CH(CF ２ ) ２ CH=CH ２ ,CH ２ =CH(CF ２ ) ６ CH=CH ２ , and CF ２ = CFO (CF ２ ) ５ Preferably, it is at least one selected from the group consisting of CN, and CF ２ = CFOCF ２ CF (CF ３ ) OCF ２ CF ２ CN and CF ２ = CFOCF ２ CF ２ CH ２ It is more preferable that it be at least one selected from the group consisting of I.

[0120] The above-mentioned fluorine-containing elastomer is preferably such that its glass transition temperature is -40°C or higher, more preferably -20°C or higher, and even more preferably -10°C or higher, in order to have excellent compression set characteristics at high temperatures. Furthermore, in order to have good cold resistance, it is preferably such that its glass transition temperature is 10°C or lower, more preferably 5°C or lower, even more preferably 0°C or lower, and most preferably -3°C or lower.

[0121] The above glass transition temperature can be determined using a differential scanning calorimeter (Mettler Toledo, DSC822e). A DSC curve is obtained by heating 10 mg of the sample at 10°C / min, and the temperature is found as the midpoint of the intersection of the extension of the baseline before and after the second-order transition of the DSC curve and the tangent line at the inflection point of the DSC curve.

[0122] The above-mentioned fluorine-containing elastomer is preferably heat-resistant, and more preferably has a Mooney viscosity ML(1+20) of 30 or higher at 170°C, more preferably 40 or higher, and even more preferably 50 or higher. Furthermore, in terms of good processability, it is preferably 150 or lower, more preferably 120 or lower, and even more preferably 110 or lower.

[0123] The above-mentioned fluorine-containing elastomer is preferably heat-resistant, and more preferably has a Mooney viscosity ML(1+20) of 30 or higher at 140°C, more preferably 40 or higher, and even more preferably 50 or higher. Furthermore, in terms of good processability, it is preferably 180 or lower, more preferably 150 or lower, and even more preferably 110 or lower.

[0124] The above-mentioned fluorine-containing elastomer is preferably heat-resistant, and more preferably has a Mooney viscosity ML(1+10) of 10 or more at 100°C, more preferably 20 or more, and even more preferably 30 or more. Furthermore, in terms of good processability, it is preferably 120 or less, more preferably 100 or less, and even more preferably 80 or less.

[0125] The above Mooney viscosity can be measured using an ALPHA TECHNOLOGIES MV2000E Mooney viscometer at 170°C, 140°C, or 100°C, in accordance with JIS K6300.

[0126] The partially fluorinated elastomers and perfluoroelastomers described above can be produced by conventional methods, but iodine compounds or bromine compounds can also be used as chain transfer agents because they result in a narrow molecular weight distribution of the resulting polymers, allow for easy control of molecular weight, and enable the introduction of iodine or bromine atoms at the terminals. A polymerization method using iodine compounds or bromine compounds includes, for example, emulsion polymerization in an aqueous medium under pressurized conditions in the presence of an iodine or bromine compound, in a substantially oxygen-free environment (iodine transfer polymerization). A typical example of an iodine or bromine compound used is, for example, one with the general formula: R １１ I ｘ Br ｙ (In the formula, x and y are integers from 0 to 2, and satisfy 1 ≤ x + y ≤ 2, R １１ Examples of compounds are those represented by a saturated or unsaturated fluorohydrocarbon group or chlorofluorohydrocarbon group having 1 to 16 carbon atoms, or a hydrocarbon group having 1 to 3 carbon atoms (which may contain an oxygen atom). By using an iodine compound or a bromine compound, an iodine atom or a bromine atom is introduced into the polymer and functions as a crosslinking point.

[0127] Examples of iodine and bromine compounds include 1,3-diiodoperfluoropropane, 2-iodoperfluoropropane, 1,4-diiodoperfluorobutane, 1,5-diiodo-2,4-dichloroperfluoropentane, 1,6-diiodoperfluorohexane, diiodomethane, 1,2-diiodoethane, 1,3-diiodo-n-propane, and 1-bromo-4-iodoperfluorobutane. These compounds may be used individually or in combination with each other.

[0128] Among these, 1,4-diiodoperfluorobutane, 1,6-diiodoperfluorohexane, and 2-iodoperfluoropropane are preferred in terms of polymerization reactivity, crosslinking reactivity, and availability.

[0129] As the fluorine-containing polymer, a fluorine-containing elastomer containing an iodine atom or a bromine atom is preferred, and a fluorine-containing elastomer having an iodine atom or a bromine atom at the main chain ends and / or side chains is more preferred.

[0130] As the perfluoroelastomer containing an iodine atom or a bromine atom, at least one selected from the group consisting of a perfluoroelastomer containing monomer units having an iodine atom or a bromine atom, a perfluoroelastomer having an iodine atom or a bromine atom at the main chain terminus, and a perfluoroelastomer having an iodine atom or a bromine atom at the main chain terminus and also containing monomer units having an iodine atom or a bromine atom is preferred.

[0131] A monomer having an iodine atom or a bromine atom is given by formula: CX ４ ２ = CX ５ R ｆ ２ -X (wherein, X ４ , X ５ Each of these is independently H, F, or an alkyl group having 1 to 5 carbon atoms, and R ｆ ２ Examples of monomers represented by (where X is a linear or branched alkylene group or oxyalkylene group which may have one or more ether-bonded oxygen atoms, may have an aromatic ring, and may have some or all of its hydrogen atoms substituted with fluorine atoms, and X is an iodine atom or a bromine atom) include:

[0132] Examples of monomers having an iodine atom or a bromine atom include, for example, formula: CX １６ ２ = CX １６ -Rf １６ CHR １６ X (wherein, X １６ Each of these is independently a hydrogen atom, a fluorine atom, or CH３ , Rf １６ is a fluoroalkylene group, a perfluoroalkylene group, a fluoro(poly)oxyalkylene group or a perfluoro(poly)oxyalkylene group, R １６ is a hydrogen atom or CH ３ A fluoromonomer represented by the formula: CX (where X is an iodine atom or a bromine atom). １６ ２ = CX １６ -Rf １７ X (wherein, X １６ Each of these is independently a hydrogen atom, a fluorine atom, or CH ３ , Rf １７ X is a fluoromonomer represented by a fluoroalkylene group, perfluoroalkylene group, fluoro(poly)oxyalkylene group, or perfluoro(poly)oxyalkylene group, where X is an iodine atom or a bromine atom. Formula: CF ２ = CFO (CF ２ CF (CF ３ )O) ｍ (CF ２ ) ｎ -X (wherein m is an integer from 0 to 5, n is an integer from 1 to 3, and X is an iodine atom, a bromine atom, or -CH) ２ A fluoromonomer represented by formula I, formula: CH ２ = CFCF ２ O(CF(CF ３ ) CF ２ O) ｍ (CF(CF ３ )) ｎ Examples include monomers represented by -X (where m is an integer from 0 to 5, n is an integer from 1 to 3, and X is an iodine atom or a bromine atom), which can be used individually or in any combination.

[0133] X １６ It is preferably a fluorine atom. Rf １６ and Rf １７ It is preferable that the group is a perfluoroalkylene group having 1 to 5 carbon atoms. １６ It is preferable that it be a hydrogen atom.

[0134] Examples of monomers having an iodine atom or a bromine atom include CF ２ = CFOCF ２ CF (CF ３ ) OCF ２ CF ２ CH ２ I, CF ２ = CFOCF ２ CF ２ CH ２ I, and CH ２ =CHCF ２ CF ２ Preferably, at least one selected from the group consisting of I, CF ２ = CFOCF ２ CF ２ CH ２ I is preferable.

[0135] The iodine and bromine content of the perfluoroelastomer containing iodine or bromine atoms is preferably 0.001 to 10% by mass, more preferably 0.01% by mass or more, even more preferably 0.1% by mass or more, and more preferably 5% by mass or less. The iodine and bromine content can be measured by elemental analysis.

[0136] As the perfluoroelastomer containing an iodine atom or a bromine atom, it is preferable to select at least one from the group consisting of perfluoroelastomers containing an iodine atom or a bromine atom containing a TFE unit, for example, a TFE / fluoromonomer copolymer represented by general formula (3), (4), or (5), and a fluoromonomer / monomer copolymer having an iodine atom or a bromine atom represented by general formula (3), (4), or (5).

[0137] When the perfluoroelastomer containing iodine or bromine atoms is a TFE / perfluoro(methyl vinyl ether) (PMVE) copolymer, the composition (mol%) of the perfluoroelastomer containing iodine or bromine atoms is preferably 45-90 / 10-55, more preferably 55-80 / 20-45, even more preferably 55-70 / 30-45, and most preferably 56-69.5 / 30.5-44.

[0138] When the perfluoroelastomer containing an iodine atom or a bromine atom is a TFE / PMVE / monomer copolymer having an iodine atom or a bromine atom, the composition (mol%) of the perfluoroelastomer containing an iodine atom or a bromine atom is preferably 45 to 89.9 / 10 to 54.9 / 0.01 to 4, more preferably 55 to 77.9 / 20 to 49.9 / 0.01 to 3.5, even more preferably 55 to 69.8 / 30 to 44.8 / 0.03 to 3.0, and most preferably 55.3 to 69.5 / 30.3 to 44.5 / 0.05 to 2.5.

[0139] When the perfluoroelastomer containing an iodine atom or a bromine atom is a fluoromonomer copolymer represented by general formula (3), (4), or (5) with 4 to 12 carbon atoms, the composition (mol%) of the perfluoroelastomer containing an iodine atom or a bromine atom is preferably 50 to 90 / 10 to 50, more preferably 60 to 88 / 12 to 40, even more preferably 65 to 85 / 15 to 35, and most preferably 66 to 84 / 16 to 34.

[0140] When a perfluoroelastomer containing an iodine or bromine atom is a TFE / fluoromonomer represented by general formula (3), (4), or (5) with 4 to 12 carbon atoms / monomer copolymer having an iodine or bromine atom, the composition (mol%) of the perfluoroelastomer containing the iodine or bromine atom is preferably 50 to 89.9 / 10 to 49.9 / 0.01 to 4, more preferably 60 to 87.9 / 12 to 39.9 / 0.1 to 3.5, even more preferably 65 to 84.8 / 15 to 34.8 / 0.2 to 3.0, and most preferably 66 to 84.3 / 15.5 to 33.8 / 0.2 to 2.0. Outside these composition ranges, the properties as a rubber elastic material are lost, and it tends to become closer to the properties of a resin.

[0141] As the perfluoroelastomer containing an iodine atom or a bromine atom, at least one selected from the group consisting of TFE / fluoromonomer copolymer represented by general formula (3), TFE / fluoromonomer / monomer copolymer having an iodine atom or a bromine atom, TFE / fluoromonomer copolymer represented by general formula (5), and TFE / fluoromonomer / monomer copolymer having an iodine atom or a bromine atom is preferred.

[0142] Perfluoroelastomers containing iodine or bromine atoms are preferably glass transition temperatures of -70°C or higher, more preferably -60°C or higher, and even more preferably -50°C or higher, due to their excellent compression set properties at high temperatures. Furthermore, due to their good cold resistance, the glass transition temperature is preferably 5°C or lower, more preferably 0°C or lower, and even more preferably -3°C or lower.

[0143] The above glass transition temperature can be determined using a differential scanning calorimeter (Mettler Toledo, DSC822e). A DSC curve is obtained by heating 10 mg of the sample at 10°C / min, and the temperature is found as the midpoint of the intersection of the extension of the baseline before and after the second-order transition of the DSC curve and the tangent line at the inflection point of the DSC curve.

[0144] Perfluoroelastomers containing iodine or bromine atoms are preferably heat-resistant, with a Mooney viscosity ML(1+10) at 100°C of 10 or more, more preferably 20 or more, and even more preferably 30 or more. Furthermore, in terms of good processability, the viscosity is preferably 120 or less, more preferably 100 or less, and even more preferably 80 or less.

[0145] The above Mooney viscosity can be measured at 100°C in accordance with JIS K6300 using an ALPHA TECHNOLOGIES MV2000E Mooney viscometer.

[0146] Fluorine-containing polymers can be manufactured by conventional methods.

[0147] The compositions of this disclosure preferably further contain an organic peroxide.

[0148] Examples of organic peroxides include 1,1-bis(t-butylperoxy)-3,5,5-trimethylcyclohexane, 2,5-dimethylhexane-2,5-dihydroperoxide, di-t-butylperoxide (Perbutyl D), t-butylcumylperoxide (Perbutyl C), dicumylperoxide (Permil D, Permil D-40, Permil D-40MB(T)), α,α-bis(t-butylperoxy)-p-diisopropylbenzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane (Perhexa 25B, Perhexa Examples include peroxides such as 2,5-dimethyl-2,5-di(t-butylperoxy)-hexyn-3 (perhexyn 25B, perhexyn 25B-40), benzoyl peroxide, t-hexyl peroxypivalate (perhexyl PV, perhexyl PV-50E), t-butyl peroxypivalate (perbutyl PV, perbutyl PV-40E), polymer blends of t-butylperoxy-3-methylbenzoate and t-butyl peroxybenzoate (perbutyl ZT), and t-butyl peroxybenzoate (perbutyl Z). Among these, dialkyl types are preferred. Furthermore, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane is particularly preferred. Generally, the type and amount of organic peroxide used are selected considering the amount of active -O-O- and the decomposition temperature.

[0149] The content of organic peroxides in the composition is preferably 0.05 parts by mass or more, more preferably 0.5 parts by mass or more, even more preferably 1.0 part by mass or more, even more preferably 1.5 parts by mass or more, particularly preferably 3.0 parts by mass or more, per 100 parts by mass of fluorine-containing polymer, in terms of facilitating crosslinking, and preferably 15 parts by mass or less, more preferably 10 parts by mass or less, even more preferably 9.0 parts by mass or less, in terms of preventing scorching in primary crosslinking processes such as press molding and facilitating molding.

[0150] The compositions of this disclosure may contain fillers.

[0151] Examples of fillers include imide-based fillers having an imide structure such as polyimide, polyamideimide, and polyetherimide; organic fillers made of engineering plastics such as polyarylate, polysulfone, polyethersulfone, polyphenylene sulfide, polyetheretherketone, polyetherketone, and polyoxybenzoate; metal oxide fillers such as aluminum oxide, silicon oxide, and yttrium oxide; metal carbides such as silicon carbide and aluminum carbide; metal nitride fillers such as silicon nitride and aluminum nitride; and inorganic fillers such as carbon black, aluminum fluoride, carbon fluoride, barium sulfate, silica, clay, and talc.

[0152] Among these, carbon black, aluminum oxide, yttrium oxide, silicon oxide, silicon carbide, polyimide, and carbon fluoride are preferred in terms of their shielding effect against various plasmas.

[0153] Furthermore, the inorganic fillers and organic fillers mentioned above may be used individually or in combination of two or more types.

[0154] The amount of filler added is preferably 0.5 to 100 parts by mass, more preferably 5 to 50 parts by mass, per 100 parts by mass of the fluorine-containing polymer.

[0155] In fields where high purity and non-contamination are not particularly required, conventional additives that are incorporated into fluorine-containing polymer compositions, such as processing aids, plasticizers, and colorants, may be added as needed.

[0156] The composition may contain an organic basic compound. An example of an organic basic compound is: CH ３ (CH ２ ) １７ -NH ２ Octadecylamine; Formula: H ２ NC(O)-(CH ２ ) １１ -CH=CH-(CH ２ ) ７ CH ３ Elkaamide; Formula: H ２ NC(O)-(CH２ ) ７ -CH=CH-(CH ２ ) ７ CH ３ Oleamide; formula: H ２ N-(CH ２ ) ６ -NH ２ The hexamethylenediamine formula: Examples include 1,8-diazabicyclounda-7-ene (DBU).

[0157] The compositions of this disclosure can be prepared by mixing the above-mentioned components using conventional polymer processing machinery, such as open rolls, Banbury mixers, and kneaders. Alternatively, they can be prepared by using a closed-type mixer. Furthermore, the compositions of this disclosure can be prepared by dissolving or dispersing the above-mentioned components in a fluorine solvent, mixing them, and then volatilizing the fluorine solvent. The compositions of this disclosure are suitably used as molding materials for obtaining molded articles by crosslinking.

[0158] 5. Crosslinked Fluorine Polymers and Molded Articles By molding the compositions of this disclosure, crosslinked fluorine polymers and molded articles can be obtained. Furthermore, by molding and crosslinking the compositions of this disclosure, crosslinked fluorine polymers and molded articles can be obtained.

[0159] One method for obtaining molded products from a composition is to first obtain a pre-molded body by molding the composition as a molding material, and then to crosslink the pre-molded body. The method for obtaining a pre-molded body from a composition can be a conventional method, and can be carried out by known methods such as heating and compressing in a mold, press-fitting into a heated mold, or extruding with an extruder. In the case of extruded products such as hoses and electric wires, molded products can be obtained by heating and crosslinking with steam or the like after extrusion.

[0160] The above crosslinking can be carried out in the order of primary crosslinking followed by secondary crosslinking. Primary crosslinking is preferably carried out at 150 to 250°C for 5 to 120 minutes, and more preferably at 160 to 200°C for 5 to 60 minutes. Any known crosslinking method can be used as the crosslinking method, such as press crosslinking.

[0161] Secondary crosslinking is preferably carried out at 180 to 320°C for 2 to 48 hours, and more preferably at 180 to 310°C for 3 to 24 hours. Temperature variations within this temperature range may also be introduced. Any known crosslinking method can be used, such as oven crosslinking.

[0162] The change in swelling rate of the molded product before and after heat treatment at 300°C for 72 hours is preferably less than 600%, more preferably less than 450%, even more preferably less than 300%, and most preferably less than 150%, in that the cross-linked structure is maintained without collapse. The change in swelling rate of the molded product can be determined by the method described in the examples.

[0163] The molded articles of this disclosure can be suitably used as sealing materials for semiconductor manufacturing equipment that requires particularly high heat resistance, especially semiconductor manufacturing equipment that undergoes high-density plasma irradiation. Examples of such sealing materials include O-rings, square rings, gaskets, packings, oil seals, bearing seals, lip seals, and the like.

[0164] In addition, it can be used in various polymer products used in semiconductor manufacturing equipment, such as diaphragms, tubes, hoses, various rubber rolls, belts, etc. It can also be used as a coating material and lining material.

[0165] Furthermore, the semiconductor manufacturing equipment referred to in this disclosure is not limited to equipment specifically for manufacturing semiconductors, but broadly includes all manufacturing equipment used in the semiconductor field that requires a high degree of cleanliness, such as equipment for manufacturing liquid crystal panels and plasma panels. Examples include the following:

[0166] (1) Etching equipment Dry etching equipment Plasma etching equipment Reactive ion etching equipment Reactive ion beam etching equipment Sputter etching equipment Ion beam etching equipment Wet etching equipment Ashing equipment (2) Cleaning equipment Dry etching cleaning equipment UV / O ３ (3) Cleaning equipment: Ion beam cleaning equipment, laser beam cleaning equipment, plasma cleaning equipment, gas etching cleaning equipment, extraction cleaning equipment, Soxhlet extraction cleaning equipment, high temperature and high pressure extraction cleaning equipment, microwave extraction cleaning equipment, supercritical extraction cleaning equipment (4) Exposure equipment: Stepper, coater, developer (5) Polishing equipment: CMP equipment (6) Film deposition equipment: CVD equipment, sputtering equipment (7) Diffusion and ion implantation equipment: Oxidation diffusion equipment, ion implantation equipment

[0167] The molded articles of this disclosure exhibit excellent performance as sealing materials for, for example, CVD equipment, plasma etching equipment, reactive ion etching equipment, ashing equipment, or excimer laser exposure machines.

[0168] 6. The first compound of this disclosure is a novel compound represented by general formula (11a) (which may be referred to as the "first compound" in this disclosure). General formula (11a):

[0169] In general formula (11a), X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ This is the base represented by (wherein r is 0 or 1, and l is an integer from 1 to 10).

[0170] X １ and X ２The non-fluorinated alkyl group may be a non-fluorinated alkyl group having 1 to 20 carbon atoms, a non-fluorinated alkyl group having 1 to 10 carbon atoms, a non-fluorinated alkyl group having 1 to 5 carbon atoms, or a non-fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ３ , -C ２ H ５ , -C ３ H ７ These are some examples.

[0171] X １ and X ２ The fluorinated alkyl group may be a partially fluorinated alkyl group or a saturated fluorinated alkyl group. １ and X ２ The fluorinated alkyl group may be a fluorinated alkyl group having 1 to 20 carbon atoms, a fluorinated alkyl group having 1 to 10 carbon atoms, a fluorinated alkyl group having 1 to 5 carbon atoms, or a fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ２ F, -CHF ２ , -CF ３ , -C ２ F ５ , -C ３ F ７ These are some examples.

[0172] X １ and X ２ The non-fluorinated alkoxy group may be a non-fluorinated alkoxy group having 1 to 20 carbon atoms, a non-fluorinated alkoxy group having 1 to 10 carbon atoms, a non-fluorinated alkoxy group having 1 to 5 carbon atoms, or a non-fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ３ , -OC ２ H ５ , -OC ３ H ７ These are some examples.

[0173] X １ and X ２ The fluorinated alkoxy group may be a partially fluorinated alkoxy group or a saturated fluorinated alkoxy group. １ and X ２The fluorinated alkoxy group may be a fluorinated alkoxy group having 1 to 20 carbon atoms, a fluorinated alkoxy group having 1 to 10 carbon atoms, a fluorinated alkoxy group having 1 to 5 carbon atoms, or a fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ２ F, -OCHF ２ , -OCF ３ , -OC ２ F ５ , -OC ３ F ７ These are some examples.

[0174] Also, X １ and X ２ The general formula is: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ The base may be represented by (wherein r is 0 or 1, and l is an integer from 1 to 10). l is independently an integer from 1 to 10, and may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3. In this general formula, X １ and X ２ Regarding this, it is as stated above. Also, Y in this general formula １ , Y ２ and Y ３ The details are as follows:

[0175] In general formula (11a), Y １ , Y ２ , Y ３ These are independently H or F.

[0176] In general formula (11a), Z is a single bond, -NH-, -NR- (R is an alkyl group having 1 to 6 carbon atoms), -O-, -S-, -CO-, -SO ２ - is a non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents. Z is preferably a single bond or a fluorinated alkylene group which may have one or more substituents.

[0177] The non-fluorinated alkylene group of Z may be a non-fluorinated alkylene group having 1 to 20 carbon atoms, a non-fluorinated alkylene group having 1 to 10 carbon atoms, or a non-fluorinated alkylene group having 1 to 8 carbon atoms, for example, -(CH ２ ) ｓ Examples include -(s is an integer from 1 to 10). s is an integer from 1 to 10, may be an integer from 1 to 8, or may be an integer from 2 to 10 or an integer from 2 to 8.

[0178] The fluorinated alkylene group of Z may be a partially fluorinated alkylene group or a saturated fluorinated alkylene group. The fluorinated alkylene group of Z may be a fluorinated alkylene group having 1 to 20 carbon atoms, a fluorinated alkylene group having 1 to 10 carbon atoms, or a fluorinated alkylene group having 1 to 8 carbon atoms, for example, -C(CF ３ ) ２ -, - (CF ２ ) ｓ - are some examples. s is an integer between 1 and 10, may be an integer between 1 and 8, or may be an integer between 2 and 10 or an integer between 2 and 8.

[0179] In general formula (11a), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3.

[0180] In general formula (11a), n is an independent integer between 1 and 5. n may be 1 or 2, or 1.

[0181] The compound represented by general formula (11a) contains X １ , X ２ However, none of these compounds are F, Z is a single bond, and m is 1.

[0182] Also, in general formula (11a), X １ , X ２ , Y １ , Y ２ , Y ３ One of them is H. X １ , X ２ , Y １ , Y ２ , Y３ When both are H, Z is a fluorinated alkylene group which may have one or more substituents.

[0183] In general formula (11a), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0184] In one embodiment, the compound of the present disclosure is represented by general formula (14). General formula (14):

[0185] In general formula (14), X １ , X ２ These are independently H or F.

[0186] In general formula (14), X ３ These are independently OH, a nonfluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｋ -CH=CH ２ This is the base represented by (wherein r is 0 or 1, and k is an integer from 1 to 10).

[0187] X ３The non-fluorinated alkoxy group may be a non-fluorinated alkoxy group having 1 to 20 carbon atoms, a non-fluorinated alkoxy group having 1 to 10 carbon atoms, a non-fluorinated alkoxy group having 1 to 5 carbon atoms, or a non-fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ３ , -OC ２ H ５ , -OC ３ H ７ These are some examples.

[0188] X ３ The general formula is: -(O) ｒ - (CX １ X ２ ) ｋ -CH=CH ２ The base may also be represented by (wherein r is 0 or 1, and k is an integer from 1 to 10). １ and X ２ k is independently H or F. k is independently an integer from 1 to 10, and may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3. In one embodiment, X ３ is -O-CH ２ -CH=CH ２ It is the group shown by .

[0189] In general formula (14), X ４ Independently, the general formula is: -(CX １ X ２ ) ｌ -CH=CH ２ The group is represented by X. １ and X ２ l is independently H or F. l is independently an integer from 1 to 10, and may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3. In one embodiment, X ４ is, -CH ２ -CH=CH ２ It is the group shown by .

[0190] In general formula (14), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3, which may be 1 or 2, which may be 2.

[0191] In general formula (14), s is an integer between 1 and 10, may be an integer between 1 and 8, or may be an integer between 2 and 10 or an integer between 2 and 8.

[0192] In general formula (14), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0193] The compound represented by general formula (14) can be produced as the compound represented by general formula (14-3) by reacting the compound represented by general formula (14-1) with the compound represented by general formula (14-2).

[0194] General formula (14-1): (In the formula, s is as explained in general formula (14).)

[0195] General formula (14-2): ClMg-(CX １ X ２ ) ｍ－１ -CH=CH ２ (In the formula, X １ , X ２ , m is as explained in general formula (14).

[0196] General formula (14-3): (In the formula, X １ , X ２ , m, X４ s is as explained in general formula (14).

[0197] After obtaining a compound represented by general formula (14-3), the compound represented by general formula (14) can also be produced as a compound represented by general formula (14-5) by reacting the compound represented by general formula (14-3) with the compound represented by general formula (14-4).

[0198] General formula (14-4): Z ３１ -X ３１ (In the formula, Z ３１ is I or Br, X ３１ It combines with OH to form X in general formula (14) ３ (However, it is a monovalent group that gives off OH.)

[0199] General formula (14-5): (In the formula, X １ , X ２ , m, X ３ , X ４ s is as explained in general formula (14). However, in general formula (14-5), X ３ (This is a group other than OH.)

[0200] The reaction between the compound represented by general formula (14-1) and the compound represented by general formula (14-2) can be carried out in a solvent. Examples of solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), sulfolane, dimethyl sulfone, diphenyl sulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, dimethoxymethane, cyclopentyl methyl ether (CPME), and 2-methyltetrahydrofuran (2-MeTHF).

[0201] The reaction temperature is preferably -40 to 60°C, and more preferably -20 to 40°C. The reaction time is preferably 0.1 to 50 hours, and more preferably 1 to 36 hours.

[0202] The reaction between the compound represented by general formula (14-3) and the compound represented by general formula (14-4) can be carried out in a solvent. Examples of solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), sulfolane, dimethyl sulfone, diphenyl sulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, dimethoxymethane, cyclopentyl methyl ether (CPME), and 2-methyltetrahydrofuran (2-MeTHF).

[0203] The reaction temperature is preferably 10 to 100°C, and more preferably 20 to 60°C. The reaction time is preferably 0.1 to 50 hours, and more preferably 1 to 36 hours.

[0204] In one embodiment, the compound of the present disclosure is represented by general formula (15). General formula (15):

[0205] In general formula (15), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be 1 or 2, which may be 1.

[0206] In general formula (15), s is an integer between 1 and 10, may be an integer between 1 and 8, or may be an integer between 2 and 10 or an integer between 2 and 8.

[0207] In general formula (15), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0208] The compound represented by general formula (15) can be produced by reacting the compound represented by general formula (15-1) with isopropylmagnesium chloride lithium chloride to obtain a Grignard reagent in which the iodine atom of the compound represented by general formula (15-1) is replaced with magnesium, and then reacting the Grignard reagent with the compound represented by general formula (15-2).

[0209] General formula (15-1): (In the formula, s is as explained in general formula (15).)

[0210] General formula (15-2): Br-(CH ２ ) ｍ -CH=CH ２ (In the formula, m is as explained in general formula (15).)

[0211] The reaction between the compound represented by general formula (15-1) and isopropylmagnesium chloride lithium chloride can be carried out in a solvent. Examples of solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), sulfolane, dimethyl sulfone, diphenyl sulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, cyclopentyl methyl ether (CPME), and 2-methyltetrahydrofuran (2-MeTHF).

[0212] The reaction temperature is preferably -50 to 0°C, and more preferably -40 to -10°C. The reaction time is preferably 0.1 to 50 hours, and more preferably 1 to 36 hours.

[0213] The reaction between Grignard reagents and compounds represented by general formula (15-2) can be carried out in a solvent. Examples of solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), sulfolane, dimethyl sulfone, diphenyl sulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, cyclopentyl methyl ether (CPME), and 2-methyltetrahydrofuran (2-MeTHF).

[0214] The reaction temperature is preferably -40 to 10°C, and more preferably -20 to 5°C. The reaction time is preferably 0.1 to 50 hours, and more preferably 1 to 36 hours.

[0215] In one embodiment, the compound of the present disclosure is represented by general formula (16). General formula (16):

[0216] In general formula (16), m is independently an integer between 2 and 10, and may be an integer between 2 and 8, an integer between 2 and 6, an integer between 2 and 4, or an integer between 2 and 3.

[0217] In general formula (16), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is R １１ and R １２ It is not substituted by any other substituent.

[0218] The compound represented by general formula (16) can be produced by reacting the compound represented by general formula (16-1) with the compound represented by general formula (16-2).

[0219] General formula (16-1):

[0220] General formula (16-2): I-(CF ２ ) ｍ -CH=CH ２ (In the formula, m is as explained in general formula (16).)

[0221] The reaction between the compound represented by general formula (16-1) and the compound represented by general formula (16-2) can be carried out in the presence of a copper catalyst. Furthermore, the above reaction can be carried out in the presence of a ligand such as 2,2'-bipyridyl.

[0222] The reaction between the compound represented by general formula (16-1) and the compound represented by general formula (16-2) can be carried out in a solvent. Examples of solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), sulfolane, dimethyl sulfone, diphenyl sulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, dimethoxymethane, cyclopentyl methyl ether (CPME), and 2-methyltetrahydrofuran (2-MeTHF).

[0223] The reaction temperature is preferably 50 to 250°C, and more preferably 80 to 150°C. The reaction time is preferably 0.1 to 50 hours, and more preferably 1 to 36 hours.

[0224] In one embodiment, the compound of the present disclosure is represented by general formula (17). General formula (17):

[0225] In general formula (17), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3.

[0226] In general formula (17), s is an integer between 1 and 10, may be an integer between 1 and 8, or may be an integer between 2 and 10 or an integer between 2 and 8.

[0227] In general formula (17), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0228] The compound represented by general formula (17) can be produced by reacting the compound represented by general formula (17-1) with bis(pinacolate)diborone to obtain the compound represented by general formula (17-2), and then reacting the compound represented by general formula (17-2) with the compound represented by general formula (17-3).

[0229] General formula (17-1): (In the formula, s is as explained in general formula (17).)

[0230] General formula (17-2): (In the formula, s is as explained in general formula (17).)

[0231] General formula (17-3): Br-(CF ２ ) ｍ -CH=CH ２ (In the formula, m is as explained in general formula (17).)

[0232] The reaction of the compound represented by general formula (17-1) with bis(pinacolate)diborone yields 1,1-bis(diphenylphosphin)ferrocenedichloropalladium(II) (PdCl ２This can be carried out in the presence of a palladium catalyst such as (dppf).

[0233] The reaction between the compound represented by general formula (17-1) and bis(pinacolate)diboron can be carried out in a solvent. Examples of solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), sulfolane, dimethyl sulfone, diphenyl sulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, dimethoxymethane, cyclopentyl methyl ether (CPME), and 2-methyltetrahydrofuran (2-MeTHF).

[0234] The reaction temperature is preferably 50 to 250°C, and more preferably 70 to 150°C. The reaction time is preferably 0.1 to 50 hours, and more preferably 1 to 36 hours.

[0235] The reaction between the compound represented by general formula (17-2) and the compound represented by general formula (17-3) can be carried out in the presence of a palladium catalyst such as tris(dibenzylideneacetone)dipalladium.

[0236] The reaction between the compound represented by general formula (17-2) and the compound represented by general formula (17-3) can be carried out in the presence of a base. Examples of bases include carbonates such as sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, cesium carbonate, and cesium hydrogen carbonate; hydroxides such as sodium hydroxide, potassium hydroxide, and cesium hydroxide; and fluorides such as sodium fluoride, potassium fluoride, and cesium fluoride.

[0237] The reaction between the compound represented by general formula (17-2) and the compound represented by general formula (17-3) can be carried out in a solvent. Examples of solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), sulfolane, dimethyl sulfone, diphenyl sulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, cyclopentyl methyl ether (CPME), and 2-methyltetrahydrofuran (2-MeTHF).

[0238] The reaction temperature is preferably 50 to 250°C, and more preferably 70 to 150°C. The reaction time is preferably 0.1 to 50 hours, and more preferably 1 to 36 hours.

[0239] 7. The second compound of this disclosure is a novel compound represented by general formula (21a) (which may be referred to as the "second compound" in this disclosure). General formula (21a):

[0240] In general formula (21a), X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ This is the base represented by (wherein r is 0 or 1, and l is an integer from 1 to 10).

[0241] X １ and X ２The non-fluorinated alkyl group may be a non-fluorinated alkyl group having 1 to 20 carbon atoms, a non-fluorinated alkyl group having 1 to 10 carbon atoms, a non-fluorinated alkyl group having 1 to 5 carbon atoms, or a non-fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ３ , -C ２ H ５ , -C ３ H ７ These are some examples.

[0242] X １ and X ２ The fluorinated alkyl group may be a partially fluorinated alkyl group or a saturated fluorinated alkyl group. １ and X ２ The fluorinated alkyl group may be a fluorinated alkyl group having 1 to 20 carbon atoms, a fluorinated alkyl group having 1 to 10 carbon atoms, a fluorinated alkyl group having 1 to 5 carbon atoms, or a fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ２ F, -CHF ２ , -CF ３ , -C ２ F ５ , -C ３ F ７ These are some examples.

[0243] X １ and X ２ The non-fluorinated alkoxy group may be a non-fluorinated alkoxy group having 1 to 20 carbon atoms, a non-fluorinated alkoxy group having 1 to 10 carbon atoms, a non-fluorinated alkoxy group having 1 to 5 carbon atoms, or a non-fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ３ , -OC ２ H ５ , -OC ３ H ７ These are some examples.

[0244] X １ and X ２ The fluorinated alkoxy group may be a partially fluorinated alkoxy group or a saturated fluorinated alkoxy group. １ and X ２The fluorinated alkoxy group may be a fluorinated alkoxy group having 1 to 20 carbon atoms, a fluorinated alkoxy group having 1 to 10 carbon atoms, a fluorinated alkoxy group having 1 to 5 carbon atoms, or a fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ２ F, -OCHF ２ , -OCF ３ , -OC ２ F ５ , -OC ３ F ７ These are some examples.

[0245] Also, X １ and X ２ The general formula is: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ The base may be represented by (wherein r is 0 or 1, and l is an integer from 1 to 10). l is independently an integer from 1 to 10, and may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3. In this general formula, X １ and X ２ Regarding this, it is as stated above. Also, Y in this general formula １ , Y ２ and Y ３ The details are as follows:

[0246] In general formula (21a), Y １ , Y ２ , Y ３ These are independently H or F.

[0247] In general formula (21a), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3, which may be 1 or 2, which may be 2.

[0248] In general formula (21a), Z １ is a benzene ring, N or CX'. X' is OH, F or H, and therefore Z １It is a benzene ring, N, COH, CF, or CH.

[0249] In general formula (21a), p is either 0 or 1. In the compound represented by general formula (21a), the molecule contains the general formula: There are q groups represented by .

[0250] Z １ When is a benzene ring, in general formula (21a), q represents the number of the above-mentioned groups bonded to the benzene ring. In general formula (21a), q is an integer from 2 to 6, and may be 2 or 3.

[0251] In general formula (21a), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0252] Z １ If is a benzene ring, then in general formula (21a), in q of the groups, p is either all 0 or all 1.

[0253] Z １ If is N or CX', then in general formula (21a), q is 3. Also, Z １ If is N or CX', then all p are 1. That is, Z １ When is N or CX', in the crosslinking aid represented by general formula (21a), the molecule contains general formula: There are three groups represented by this symbol, all of which are bonded to the N, COH, CF, or N or C of CH.

[0254] In general formula (21a), X １ , X ２ , Y １ , Y ２ , Y ３ One of them is H, and it is not possible for all of them to be H.

[0255] In one embodiment, the compound of the present disclosure is represented by general formula (22a). General formula (22a):

[0256] In general formula (22a), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3, which may be 1 or 2, which may be 2.

[0257] In general formula (22a), p is either 0 or 1. In the compound represented by general formula (22a), the molecule contains the general formula: There are q groups represented by . In general formula (22a), in q of these groups, p is either all 0 or all 1.

[0258] In general formula (22a), q represents the number of the above-mentioned groups bonded to the benzene ring. In general formula (22a), q is an integer from 2 to 6, and may be 2 or 3.

[0259] In general formula (22a), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0260] In one embodiment, the compound represented by general formula (22a) is the following compound. (In the formula, the number (4) at the end represents the number of groups bonded to the benzene ring. It is preferable that four groups are bonded to positions 1, 2, 4, and 5 of the benzene ring.)

[0261] In one embodiment, the compound of the present disclosure is represented by general formula (23a). General formula (23a):

[0262] In general formula (23a), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3, which may be 1 or 2, which may be 2.

[0263] In general formula (23a), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0264] In one embodiment, the compound of the present disclosure is represented by general formula (24a). General formula (24a):

[0265] In general formula (24a), X' is OH, F, or H.

[0266] In general formula (24a), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be an integer from 2 to 10, an integer from 2 to 8, an integer from 2 to 6, an integer from 2 to 4, or an integer from 2 to 3, which may be 1 or 2, which may be 2.

[0267] In general formula (24a), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0268] The second compound can be produced, for example, by reacting a compound represented by general formula (21a-1) with a compound represented by general formula (21a-2).

[0269] General formula (21a-1): (In the formula, Z １ p and q are as described in general formula (21a). The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.

[0270] General formula (21a-2): I-(CX １ X ２ ) ｍ -CY １ =CY ２ Y ３ (In the formula, X １ , X ２ , Y １ , Y ２ , Y ３ , m is as explained in general formula (21a).

[0271] The reaction between the compound represented by general formula (21a-1) and the compound represented by general formula (21a-2) can be carried out in the presence of a copper catalyst. Furthermore, the above reaction can be carried out in the presence of ligands such as 2,2'-bipyridyl and 1,10-phenanthroline.

[0272] Alternatively, a complex formed from the above ligand and a metal ion such as a copper ion may be reacted with a compound represented by general formula (21a-2), and then the resulting intermediate (complex) may be reacted with a compound represented by general formula (21a-1) to produce a second compound.

[0273] The reaction between the compound represented by general formula (21a-1) and the compound represented by general formula (21a-2) can be carried out in a solvent. Examples of solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), sulfolane, dimethyl sulfone, diphenyl sulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, dimethoxymethane, cyclopentyl methyl ether (CPME), and 2-methyltetrahydrofuran (2-MeTHF).

[0274] The reaction temperature is preferably 50 to 250°C, and more preferably 80 to 150°C. The reaction time is preferably 0.1 to 50 hours, and more preferably 1 to 36 hours.

[0275] 8. Third Compound The compounds of this disclosure are novel compounds represented by general formula (31a) (which may be referred to as the "third compound" in this disclosure). General formula (31a):

[0276] In general formula (31a), X １ , X ２These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ This is the base represented by (wherein r is 0 or 1, and l is an integer from 1 to 10). １ and X ２ H is preferred.

[0277] X １ and X ２ The non-fluorinated alkyl group may be a non-fluorinated alkyl group having 1 to 20 carbon atoms, a non-fluorinated alkyl group having 1 to 10 carbon atoms, a non-fluorinated alkyl group having 1 to 5 carbon atoms, or a non-fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ３ , -C ２ H ５ , -C ３ H ７ These are some examples.

[0278] X １ and X ２ The fluorinated alkyl group may be a partially fluorinated alkyl group or a saturated fluorinated alkyl group. １ and X ２ The fluorinated alkyl group may be a fluorinated alkyl group having 1 to 20 carbon atoms, a fluorinated alkyl group having 1 to 10 carbon atoms, a fluorinated alkyl group having 1 to 5 carbon atoms, or a fluorinated alkyl group having 1 to 3 carbon atoms, for example, -CH ２ F, -CHF ２ , -CF ３ , -C ２ F ５ , -C ３ F ７ These are some examples.

[0279] X １ and X ２The non-fluorinated alkoxy group may be a non-fluorinated alkoxy group having 1 to 20 carbon atoms, a non-fluorinated alkoxy group having 1 to 10 carbon atoms, a non-fluorinated alkoxy group having 1 to 5 carbon atoms, or a non-fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ３ , -OC ２ H ５ , -OC ３ H ７ These are some examples.

[0280] X １ and X ２ The fluorinated alkoxy group may be a partially fluorinated alkoxy group or a saturated fluorinated alkoxy group. １ and X ２ The fluorinated alkoxy group may be a fluorinated alkoxy group having 1 to 20 carbon atoms, a fluorinated alkoxy group having 1 to 10 carbon atoms, a fluorinated alkoxy group having 1 to 5 carbon atoms, or a fluorinated alkoxy group having 1 to 3 carbon atoms, for example, -OCH ２ F, -OCHF ２ , -OCF ３ , -OC ２ F ５ , -OC ３ F ７ These are some examples.

[0281] Also, X １ and X ２ The general formula is: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ The base may be represented by (wherein r is 0 or 1, and l is an integer from 1 to 10). l is independently an integer from 1 to 10, and may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3. In this general formula, X １ and X ２ Regarding this, it is as stated above. Also, Y in this general formula １ , Y ２ and Y ３ The details are as follows:

[0282] In general formula (31a), Y１ , Y ２ , Y ３ Y is independently either H or F. １ and Y ２ H is preferred.

[0283] In general formula (31a), Z is -O-, -S-, -CO-, -SO ２ - is a non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents. A fluorinated alkylene group which may have one or more substituents is preferred for Z.

[0284] The non-fluorinated alkylene group of Z may be a non-fluorinated alkylene group having 1 to 20 carbon atoms, a non-fluorinated alkylene group having 1 to 10 carbon atoms, or a non-fluorinated alkylene group having 1 to 8 carbon atoms, for example, -(CH ２ ) ｓ Examples include -(s is an integer from 1 to 10). s is an integer from 1 to 10, may be an integer from 1 to 8, or may be an integer from 2 to 10 or an integer from 2 to 8.

[0285] The fluorinated alkylene group of Z may be a partially fluorinated alkylene group or a saturated fluorinated alkylene group. The fluorinated alkylene group of Z may be a fluorinated alkylene group having 1 to 20 carbon atoms, a fluorinated alkylene group having 1 to 10 carbon atoms, or a fluorinated alkylene group having 1 to 8 carbon atoms, for example, -C(CF ３ ) ２ -, - (CF ２ ) ｓ - are some examples. s is an integer between 1 and 10, may be an integer between 1 and 8, or may be an integer between 2 and 10 or an integer between 2 and 8.

[0286] In general formula (31a), m is independently an integer from 1 to 10, which may be an integer from 1 to 8, an integer from 1 to 6, an integer from 1 to 4, or an integer from 1 to 3, which may be 1 or 2, which may be 1.

[0287] In general formula (31a), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0288] In one embodiment, the compound of the present disclosure is represented by general formula (33). General formula (33):

[0289] In general formula (33), s is an integer between 1 and 10, may be an integer between 1 and 8, or may be an integer between 2 and 10 or an integer between 2 and 8.

[0290] In general formula (33), the hydrogen atom bonded to the benzene ring may be substituted with any substituent. Examples of such substituents include halogen atoms, optionally branched alkyl groups, optionally branched alkyl halides, cycloalkyl groups, cycloalkyl halides, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, and substituted or unsubstituted phenyl groups. Among these, fluorine atoms, C1-C3 alkyl groups, C1-C3 alkyl halides, C1-C3 alkoxy groups, C1-C3 acyl groups, C1-C3 acyloxy groups, or C1-C3 alkoxycarbonyl groups are preferred, fluorine atoms, methyl groups, trifluoromethyl groups, methoxy groups, acetyl groups, acetoxy groups, or methoxycarbonyl groups are more preferred, and fluorine atoms or trifluoromethyl groups are particularly preferred. In one embodiment, the hydrogen atom bonded to the benzene ring is not substituted with any substituent.

[0291] The third compound can be produced by reacting a compound represented by general formula (31a-1) (a diiodine compound) with a compound represented by general formula (31a-2) to obtain a compound represented by general formula (31a-3), then reducing the compound represented by general formula (31a-3) to obtain a compound represented by general formula (31a-4), and then dehydrating the compound represented by general formula (31a-4).

[0292] General formula (31a-1): I - Z - I (wherein Z is as explained in general formula (31a).)

[0293] General formula (31a-2): (In the formula, X １ , X ２ ,m is as explained in general formula (31a).

[0294] General formula (31a-3): (In the formula, Z, １ , X ２ ,m is as explained in general formula (31a).

[0295] General formula (31a-4): (In the formula, Z,１ , X ２ ,m is as explained in general formula (31a).

[0296] The reaction between the compound represented by general formula (31a-1) and the compound represented by general formula (31a-2) can be carried out in the presence of a copper catalyst. Furthermore, the above reaction can be carried out in the presence of a ligand such as 2,2'-bipyridyl.

[0297] The reaction between the compound represented by general formula (31a-1) and the compound represented by general formula (31a-2) can be carried out in a solvent. Examples of solvents include N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), tetramethylurea (TMU), 1,3-dimethyl-2-imidazolidone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), sulfolane, dimethyl sulfone, diphenyl sulfone, cyclopentanone, cyclohexanone, tetrahydrofuran (THF), 1,4-dioxane, dimethoxymethane, cyclopentyl methyl ether (CPME), and 2-methyltetrahydrofuran (2-MeTHF).

[0298] The reaction temperature is preferably 50 to 250°C, and more preferably 80 to 150°C. The reaction time is preferably 0.1 to 50 hours, and more preferably 1 to 36 hours.

[0299] The reduction of the compound represented by general formula (31a-3) is carried out in a solvent by reducing the compound represented by general formula (31a-3) with sodium borohydride (NaBH). ４ This can be done by heating it together with ( ).

[0300] Dehydration of the compound represented by general formula (31a-4) can be carried out by heating the compound represented by general formula (31a-4) together with p-toluenesulfonic acid monohydrate (PTSA) in a solvent.

[0301] The first to third compounds of this disclosure can be suitably used as crosslinking aids for crosslinking fluorine-containing polymers.

[0302] Although embodiments have been described above, it should be understood that various modifications to the form and details are possible without departing from the spirit and scope of the claims.

[0303] <1> In the first aspect of this disclosure, a crosslinking aid represented by general formula (11) is provided. General formula (11): (In the formula, X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ The base represented by (wherein r is 0 or 1, and l is an integer from 1 to 10) Y １ , Y ２ , Y ３ Independently, H or F, Z is a single bond, -NH-, -NR- (R is an alkyl group with 1 to 6 carbon atoms), -O-, -S-, -CO-, -SO ２ -, a non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents, m independently represents an integer from 1 to 10, and n independently represents an integer from 1 to 5. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.) <2> According to a second aspect of this disclosure, a crosslinking aid according to the first aspect is provided, represented by general formula (12). General formula (12): (In the formula, X １ , X ２is independently H or F, Z is a single bond or a fluorinated alkylene group which may have one or more substituents, and m is independently an integer from 1 to 10. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.) <3> According to a third aspect of this disclosure, a crosslinking aid according to the first aspect is provided, represented by general formula (13). General formula (13): (In the formula, X １ , X ２ These are, independently, H or F, X ３ These are independently OH, a nonfluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｋ -CH=CH ２ The base represented by (wherein r is 0 or 1, and k is an integer from 1 to 10) X ４ Independently, the general formula is: -(CX １ X ２ ) ｌ -CH=CH ２ (wherein l is an integer from 1 to 10) a group represented by, Z is a single bond or a fluorinated alkylene group which may have one or more substituents, and m is independently an integer from 1 to 10. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.) <4> According to a fourth aspect of this disclosure, a crosslinking aid represented by general formula (21) is provided. General formula (21): (In the formula, X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３a group represented by (wherein r is 0 or 1, and l is an integer of 1 to 10), Y １ , Y ２ , Y ３ are each independently H or F, Z １ is a benzene ring, N, or CX' (where X' is OH, F or H), m is each independently an integer of 1 to 10, p is 0 or 1, when Z １ is a benzene ring, q is an integer of 2 to 6, when Z １ is N or CX', q is 3. When Z １ is a benzene ring, all p are 0 or all are 1, when Z １ is N or CX', all p are 1. A hydrogen atom bonded to the benzene ring may be substituted with any substituent.) <5> According to a fifth aspect of the present disclosure, there is provided a crosslinking coagent according to the fourth aspect represented by general formula (22). General formula (22): (wherein, X １ , X ２ are each independently H or F, m is each independently an integer of 1 to 10, p is 0 or 1, q is an integer of 2 to 6. All p are 0 or all are 1. A hydrogen atom bonded to the benzene ring may be substituted with any substituent.) <6> According to a sixth aspect of the present disclosure, there is provided a crosslinking coagent represented by general formula (31). General formula (31): (wherein, X １ , X ２ are each independently H, F, OH, a non-fluorinated alkyl group optionally having one or more substituents, a fluorinated alkyl group optionally having one or more substituents, a non-fluorinated alkoxy group optionally having one or more substituents, a fluorinated alkoxy group optionally having one or more substituents, or a group represented by general formula: -(O) ｒ -(CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ (wherein r is 0 or 1, and l is an integer of 1 to 10), Y１ , Y ２ , Y ３ Independently, H or F, Z is a single bond, -NH-, -NR- (R is an alkyl group with 1 to 6 carbon atoms), -O-, -S-, -CO-, -SO ２ -, a non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents, m independently represents an integer from 1 to 10. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.) <7> According to the seventh aspect of this disclosure, a crosslinking aid according to the sixth aspect, represented by general formula (32), is provided. General formula (32): (In the formula, X １ , X ２is independently H or F, Z is a single bond or a fluorinated alkylene group which may have one or more substituents, and m is independently an integer from 1 to 10. The hydrogen atom bonded to the benzene ring may be substituted with any substituent.) <8> According to the eighth aspect of this disclosure, a composition is provided which contains a crosslinking aid according to any of the first to seventh aspects and a fluorine-containing polymer. <9> According to the ninth aspect of this disclosure, a composition is provided according to the eighth aspect in which the crosslinking aid is contained in an amount of 0.1 to 10 parts by mass per 100 parts by mass of the fluorine-containing polymer. <10> According to the tenth aspect of this disclosure, a composition is provided according to the eighth or ninth aspect in which the fluorine-containing polymer is a fluorine-containing elastomer. <11> According to the eleventh aspect of this disclosure, a composition is provided according to any of the eighth to tenth aspects in which the fluorine-containing polymer contains an iodine atom or a bromine atom. <12> According to the twelfth aspect of this disclosure, a composition according to any eighth to eleventh aspect is provided, further containing an organic peroxide. <13> According to the thirteenth aspect of this disclosure, a composition according to the twelfth aspect is provided, wherein the content of the organic peroxide is 0.05 to 10 parts by mass per 100 parts by mass of the fluorine-containing polymer. <14> According to the fourteenth aspect of this disclosure, a crosslinked fluorine-containing polymer is provided, obtained by crosslinking a composition according to any eighth to thirteenth aspect. <15> According to the fifteenth aspect of this disclosure, a molded article obtained from the crosslinked fluorine-containing polymer according to the fourteenth aspect is provided. <16> According to the sixteenth aspect of this disclosure, a molded article according to the fifteenth aspect is provided, which is a sealing material. <17> According to the seventeenth aspect of this disclosure, a compound represented by general formula (11a) is provided. General formula (11a): (In the formula, X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O)ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ The base represented by (wherein r is 0 or 1, and l is an integer from 1 to 10) Y １ , Y ２ , Y ３ Independently, H or F, Z is a single bond, -NH-, -NR- (R is an alkyl group with 1 to 6 carbon atoms), -O-, -S-, -CO-, -SO ２ -, a non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents, m independently represents an integer from 1 to 10, and n independently represents an integer from 1 to 5. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. However, X １ , X ２ However, this excludes compounds where all are F, Z is a single bond, and m is 1. １ , X ２ , Y １ , Y ２ , Y ３ Either of them is H, and when both are H, Z is a fluorinated alkylene group which may have one or more substituents.) <18> According to the eighteenth aspect of this disclosure, compounds according to the seventeenth aspect are provided which are represented by general formula (14). General formula (14): (In the formula, X １ , X ２ These are, independently, H or F, X ３ These are independently OH, a nonfluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｋ -CH=CH ２ The base represented by (wherein r is 0 or 1, and k is an integer from 1 to 10) X ４ Independently, the general formula is: -(CX １ X ２ ) ｌ -CH=CH ２(wherein l is an integer from 1 to 10) a group represented by m is independently an integer from 1 to 10, and s is an integer from 1 to 10. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.) <19> According to the 19th aspect of this disclosure, compounds according to the 17th aspect represented by general formula (15) are provided. General formula (15): (wherein m independently represents an integer from 1 to 10, and s represents an integer from 1 to 10. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.) <20> According to the 20th aspect of this disclosure, compounds according to the 17th aspect, represented by general formula (16), are provided. General formula (16): (wherein m independently represents an integer from 2 to 10. The hydrogen atom bonded to the benzene ring may be substituted with any substituent.) <21> According to the 21st aspect of this disclosure, a compound according to the 17th aspect, represented by general formula (17), is provided. General formula (17): (wherein m independently represents an integer from 1 to 10, and s represents an integer from 1 to 10. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.) <22> According to the 22nd aspect of this disclosure, compounds represented by general formula (21a) are provided. General formula (21a): (In the formula, X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ The base represented by (wherein r is 0 or 1, and l is an integer from 1 to 10) Y １ , Y ２ , Y ３ These are independently H or F, Z１ is a benzene ring, N, or CX' (X' is OH, F or H); m is independently an integer of 1 to 10; p is 0 or 1; Z １ is a benzene ring, q is an integer of 2 to 6, and Z １ is N or CX', q is 3. When Z １ is a benzene ring, all p are 0 or all p are 1, and when Z １ is N or CX', all p are 1. A hydrogen atom bonded to the benzene ring may be substituted with any optional substituent. Provided that any one of X １ , X ２ , Y １ , Y ２ , Y ３ is H, and all are not H at the same time.) <23> According to a twenty-third aspect of the present disclosure, there is provided the compound according to the twenty-second aspect, which is a compound represented by general formula (22a). General formula (22a): (wherein, m is independently an integer of 1 to 10; p is 0 or 1; q is an integer of 2 to 6. All p are 0 or all p are 1. A hydrogen atom bonded to the benzene ring may be substituted with any optional substituent.) <24> According to a twenty-fourth aspect of the present disclosure, there is provided a compound represented by general formula (31a). General formula (31a): (wherein, X １ , X ２ are each independently H, F, OH, a non-fluorinated alkyl group optionally having one or more substituents, a fluorinated alkyl group optionally having one or more substituents, a non-fluorinated alkoxy group optionally having one or more substituents, a fluorinated alkoxy group optionally having one or more substituents, or a group represented by general formula: -(O) ｒ -(CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ (wherein r is 0 or 1, and l is an integer of 1 to 10); Y １ , Y ２, Y ３ Independently, H or F, and Z are -O-, -S-, -CO-, -SO ２ -, a non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents, m independently represents an integer from 1 to 10. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.) <25> According to the 25th aspect of this disclosure, a compound according to the 24th aspect is provided, which is a compound represented by general formula (33). General formula (33): (In the formula, s represents an integer from 1 to 10. Hydrogen atoms bonded to the benzene ring may be substituted with any substituent.)

[0304] Next, embodiments of the present disclosure will be described with reference to examples, but the present disclosure is not limited to such embodiments.

[0305] <Synthesis of Crosslinkable Fluorine-Containing Aromatic Compounds> Synthesis Example 1 1.7 g of 1,4-diiodobenzene, 2.9 g of copper powder, and 0.72 g of 2,2'-bipyridyl were placed in a reaction vessel for the synthesis of compound 1. After purging with nitrogen, 6.5 ml of dimethyl sulfoxide (DMSO) was added and the mixture was stirred. 5.5 g of 3,3,4,4,5,5,6,6-octafluoro-6-iodohexa-1-ene was added and the mixture was reacted overnight at 110°C. The reaction mixture was allowed to cool to room temperature, water and diethyl ether were added and the mixture was stirred, followed by filtration using Celite. The organic layer was washed with dilute hydrochloric acid, water, and saturated brine. After solvent removal, the crude product was purified by silica gel column chromatography (hexane) to obtain 0.60 g of the aromatic compound (compound 1) shown in the following formula.

[0306]

[0307] １ H-NMR (CDCl ３ , 400MHz): 5.75-5.81 (m, 2H), 5.89-6.06 (m, 4H), 7.73 (s, 4H) １９ F-NMR (CDCl ３, 376MHz): -111.0 to -111.3 (m, 4F), -113.7 to -114.0 (m, 4F), -121.0 to -121.9 (m, 4F), -122.6 to -123.3 (m, 4F)

[0308] Synthesis Example 2 In a reaction vessel for the synthesis of Compound 2, 1.5 g of 4,4'-diiodobiphenyl, 1.88 g of copper powder, and 0.8 g of 2,2'-bipyridyl were placed, and 15.0 ml of anhydrous dimethyl sulfoxide (DMSO) was added and the mixture was stirred. 7.2 g of 3,3,4,4,5,5,6,6-octafluoro-6-iodohexa-1-ene was added and the mixture was reacted overnight at 100°C. The reaction mixture was allowed to cool to room temperature, water and ethyl acetate were added, and the mixture was stirred and then filtered by Celite filtration. The organic layer was washed twice with water, and after solvent removal, the crude product was purified by silica gel column chromatography to obtain 0.92 g of the aromatic compound (Compound 2) shown in the following formula.

[0309]

[0310] １ ¹H-NMR (acetone-d6, 400 MHz): 5.92–6.01 (m, 4H), 6.17–6.27 (m, 2H), 7.69–7.79 (m, 4H), 7.90–8.00 (m, 4H) １９ F-NMR (acetone-d6, 376 MHz): -109.4 to -109.7 (m, 4F), -112.4 to -112.7 (m, 4F), -120.1 to -121.2 (m, 4F), -122.4 to -122.7 (m, 4F)

[0311] Synthesis Example 3 In a reaction vessel for the synthesis of compound 3, 2.4 g of 4,4'-diiodobiphenyl, 6.5 g of copper powder, and 1.7 g of 2,2'-bipyridyl were placed, and 18.0 ml of anhydrous dimethyl sulfoxide (DMSO) was added and the mixture was stirred. 5 ml of 3,3,4,4-tetrafluoro-4-iodobutene was added and the mixture was reacted overnight at 160°C. The reaction mixture was allowed to cool to room temperature, water and ethyl acetate were added, and the mixture was stirred and then filtered by Celite filtration. The organic layer was washed twice with water, and after solvent removal, the crude product was purified by silica gel column chromatography to obtain 0.22 g of the aromatic compound (compound 3) shown in the following formula.

[0312]

[0313] １ H-NMR (CDCl ３ , 400MHz): 5.70-5.72 (m, 2H), 5.83-6.88 (m, 2H), 5.98-6.08 (m, 2H), 7.62-7.71 (m, 8H) １９ F-NMR (CDCl ３ , 376MHz): -111.67 to -111.75 (m, 4F), -114.07 to -114.09 (m, 4F).

[0314] Synthesis Example 4 In a reaction vessel for the synthesis of compound 4, 1.65 g of 4,4'-diiodo-2,2'-bis(trifluoromethyl)-1,1'-biphenyl, 3.86 g of copper powder, and 0.24 g of 2,2'-bipyridyl were weighed out. After purging with nitrogen gas, 20.0 ml of anhydrous dimethyl sulfoxide (DMSO) was added and the mixture was stirred. 15.0 g of 3,3,4,4,5,5,6,6-octafluoro-6-iodohexa-1-ene was added and the mixture was reacted overnight at 95°C. The reaction mixture was allowed to cool to room temperature, water and ethyl acetate were added and the mixture was stirred, followed by filtration using Celite. The organic layer was washed twice with water, and after solvent removal, the crude product was purified by silica gel column chromatography (hexane) to obtain 0.98 g of the aromatic compound (compound 4) shown in the following formula.

[0315]

[0316] １ ¹H-NMR (acetone-d6, 400 MHz): 5.90–6.06 (m, 4H), 6.19–6.29 (m, 2H), 7.71–7.81 (m, 4H), 7.98–8.12 (m, 4H) １９ F-NMR (acetone-d6, 376 MHz): -57.2 to -57.3 (m, 6H), -109.9 to -110.0 (m, 4F), -112.5 to -112.6 (m, 4F), -120.9 to -121.1 (m, 4F), -122.5 to -122.7 (m, 4F)

[0317] Synthesis Example 5 In a reaction vessel for the synthesis of compound 5, 3.37 g of 1,3,5-tris(4-iodophenyl)benzene, 9.47 g of copper powder, and 1.62 g of 2,2'-bipyridyl were weighed out, and 30.0 ml of anhydrous dimethyl sulfoxide (DMSO) was added and the mixture was stirred. 13.0 g of 3,3,4,4,5,5,6,6-octafluoro-6-iodohexa-1-ene was added and the mixture was reacted overnight at 100°C. The reaction mixture was allowed to cool to room temperature, water and ethyl acetate were added and the mixture was stirred, followed by filtration using Celite. The organic layer was washed twice with water, and after solvent removal, the crude product was purified by silica gel column chromatography (hexane) to obtain 0.61 g of the aromatic compound (compound 5) shown in the following formula.

[0318]

[0319] １ ¹H-NMR (acetone-d6, 400 MHz): 5.92–6.03 (m, 6H), 6.12–6.22 (m, 3H), 7.70–7.80 (m, 6H), 8.12–8.15 (m, 9H) １９ F-NMR (acetone-d6, 376 MHz): -110.64 to -110.71 (m, 6F), -113.95 to -114.05 (m, 6F), -121.77 to -121.79 (m, 6F), -123.52 to -123.56 (m, 6F)

[0320] Synthesis Example 6 500 mg of 4,4-biphenyldiboronic acid, 1.30 g of 3-bromo-3,3-difluoropropene, 75.7 mg of tris(dibenzylideneacetone)dipalladium, 857 mg of calcium carbonate, 18.6 μL of water, and 10.4 mL of dimethoxymethane were added to the reaction vessel for the synthesis of compound 6, and the mixture was stirred at 80°C for 24 hours. The reaction solution was allowed to cool, diluted with tetrahydrofuran, filtered by Celite, and the filtrate was concentrated. The obtained crude product was purified by silica gel column chromatography (hexane, ethyl acetate) to obtain 126 mg of the aromatic compound (compound 6) shown in the following formula.

[0321]

[0322] １ H-NMR (CDCl ３, 400MHz): 5.52 (d, J = 10.4Hz, 2H), 6.62 (dt, J = 16.9, 3.2Hz, 2H), 6.13-6.25 (m, 2H), 7.59 (d, J=8.7Hz, 4H), 7.65 (d, J=8.7Hz, 4H). １９ F-NMR (CDCl ３ , 376MHz): -93.3 (d, J=9.0Hz, 4F).

[0323] Synthesis Example 7 Synthesis Example 7-1 of Compound 7 Synthesis of Intermediate (M-1) 8.3 g of 4-iodoaniline and 11.1 g of copper powder were added to a reaction vessel, and after purging with nitrogen, 22.7 mL of dimethyl sulfoxide (DMSO) was added and the mixture was stirred at 110°C. A DMSO solution of 1,6-diiodoperfluorohexane (1.8 M, 2.8 mL) was added dropwise to this solution and the reaction was carried out overnight. After diluting the reaction mixture with diethyl ether, it was filtered by Celite and washed with water and saturated brine. After solvent removal, the mixture was purified by silica gel column chromatography (hexane, ethyl acetate) to obtain an aromatic compound having an amino group represented by the following formula (M-1) (intermediate (M-1)).

[0324]

[0325] Example 7-2 Synthesis of Intermediate (M-2) 5.34 g of intermediate (M-1), 5.04 g of copper(I) iodide, and 6.72 g of iodine were added to a reaction vessel, and after purging with nitrogen, 44.7 mL of tetrahydrofuran (THF) was added and the mixture was stirred. 7.7 mL of t-butyl nitrite was added to this solution and the mixture was reacted at 50°C for 5 hours. The reaction mixture was diluted with ethyl acetate, filtered, and washed with aqueous sodium sulfite solution and saturated brine. After solvent removal, the mixture was recrystallized from ethyl acetate / hexane to obtain the diiodic aromatic compound (intermediate (M-2)) represented by the following formula (M-2).

[0326]

[0327] Example 7-3 Synthesis of intermediate (M-3) In the reaction vessel, add 2.00 g of intermediate (M-2), 1.58 g of bis(pinacolate)diborone, and Pd (dppf) ２ Cl ２137 mg of potassium acetate, 1.67 g of potassium acetate, and 31.2 mL of DMSO were added and heated at 80°C for 22 hours. After cooling to room temperature, the mixture was diluted with diethyl ether, and water was added for extraction. The organic layer was washed with saturated saline solution, dried, and the solvent was removed by distillation. The resulting solid was rinsed with chilled dichloromethane, yielding 1.46 g of the target M-3.

[0328] １ H-NMR (CDCl ３ , 400MHz): 1.35 (s, 24H), 7.57 (d, J=7.8Hz, 4H), 7.91 (d, J=7.8Hz, 4H). １９ F-NMR (CDCl ３ , 376MHz): -110.9 to -111.0 (m, 4F), -121.1 to -121.3 (m, 4F), -121.8 to -121.9 (s, 4F).

[0329] Example 7-4 To a reaction vessel for the synthesis of compound 7, 500 mg of intermediate (M-3), 445 mg of 3-bromo-3,3-difluoropropene, 119 mg of potassium hydroxide, 25.9 mg of tris(dibenzylideneacetone)dipalladium, and 3.54 mL of dimethoxymethane were added and the mixture was stirred at 80°C for 24 hours. After the reaction solution was allowed to cool to room temperature, it was diluted with tetrahydrofuran and filtered through Celite. The resulting filtrate was concentrated and purified by silica gel column chromatography (hexane, ethyl acetate) to obtain 71.9 mg of the target compound 7.

[0330]

[0331] １ H-NMR (CDCl ３　 , 400MHz): 5.53 (d, J=11.0Hz, 2H), 6.60 (dt, J=16.9, 2.3Hz, 2H), 6.09-6.21 (m, 2H), 7.64 (d, J=8.7Hz, 4H), 7.68 (d, J=8.7Hz, 4H). １９ F-NMR (CDCl ３ , 376MHz): -94.4 (d, J=8.9Hz, 4F), -111.06 to -111.08 (m, 4F), -121.02 to -121.26 (m, 4F), -121.15 to -121.17 (m, 4F).

[0332] Synthesis Example 8 1.0 g of the synthesis intermediate (M-2) of compound 8 was added to the reaction vessel, and after purging with nitrogen, 3.0 mL of THF was added and the mixture was stirred at -30°C. 3.3 mL of a THF solution (1.3 M) of isopropylmagnesium chloride lithium chloride complex was added dropwise to this solution and the mixture was reacted for 2 hours. 0.50 mL of allyl bromide was added to the reaction mixture and the mixture was stirred at -10°C for 1 hour, then the reaction was allowed to continue overnight at 0°C. The reaction mixture was quenched with dilute hydrochloric acid, extracted with diethyl ether, and washed with saturated brine. After solvent removal, the mixture was purified by silica gel column chromatography (hexane) to obtain a white solid aromatic compound (compound 8) having a bifunctional allyl group as shown in the following formula (0.46 g).

[0333]

[0334] １ H-NMR (CDCl ３ , 400MHz): 3.45 (d, J = 6.63, 4H), 5.06-5.16 (m, 4H), 5.89-6.03 (m, 2H), 7.41 (q ＡＢ , J=8.23, 8H) １９ F-NMR (CDCl ３ , 376MHz): -110.0 to -110.6 (m, 4F), -121.0 to -121.5 (m, 4F), -121.6 to -122.1 (m, 4F)

[0335] Synthesis Example 9 Synthesis Example 9-1 of Compound 9 Synthesis of Intermediate (M-4) 4.193 g of methyl 4-iodobenzoate, 3.05 g of copper powder, and 0.25 g of 2,2'-bipyridyl were added to a reaction vessel, and after purging with nitrogen, 13.7 mL of DMSO was added and stirred. A DMSO solution of 1,6-diiodoperfluorohexane (0.6 M, 13.7 mL) was added dropwise to this solution and the reaction was carried out at 90°C for 10 hours. Water and ethyl acetate were added to the reaction mixture, and the mixture was filtered by Celite and washed with water and saturated brine. After solvent removal, the mixture was washed with cold methanol to obtain an aromatic compound having an ester group represented by the following formula (M-4) (intermediate (M-4)).

[0336]

[0337] Example 9-2 Synthesis of Intermediate (M-5) 4.56 g of intermediate (M-4) and 34.2 mL of THF were added to a reaction vessel, stirred, and cooled to 0°C. 19.2 mL of 2 M allyl magnesium chloride THF solution was added dropwise to this solution, and the reaction was carried out at room temperature for 16 hours. After quenching with dilute hydrochloric acid, the mixture was extracted with ethyl acetate and washed with water and saturated brine. After solvent removal, the crude product was recrystallized from hexane to obtain an aromatic compound having an allyl group represented by the following formula (M-5) (intermediate (M-5)).

[0338]

[0339] Example 9-3 Synthesis of Compound 9 0.78 g of sodium hydride (liquid paraffin dispersion, 60%) was placed in a reaction vessel, suspended in 24.7 mL of THF, and cooled to 0°C. A THF solution of intermediate (M-5) (0.2 M, 24.7 mL) was added dropwise over 20 minutes, and the mixture was stirred at 0°C for 1 hour. 1.21 mL of methyl iodide was added dropwise to this solution, and the temperature was raised to 35°C and the reaction was carried out for 2 hours. After quenching with dilute hydrochloric acid, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine. After solvent removal, the mixture was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain a white solid (2.54 g) of an aromatic compound (compound 9) having four allyl groups, as shown in the following formula.

[0340]

[0341] １ H-NMR (CDCl ３ , 400MHz): 2.66 (dd, J=7.09Hz, 8H), 3.14 (s, 6H), 4.98-5.11 (m, 8H), 5.52-5.65 (m, 4H), 7.53 (q ＡＢ , J=8.69Hz, 8H) １９ F-NMR (CDCl ３ , 376MHz): -109.6 to -111.2 (m, 4F), -121.3 (m, 4F), -121.5 to -122.2 (m, 4F)

[0342] Synthesis Example 10: Synthesis of Compound 10. The procedure was carried out in the same manner as in Example 9-3, except that 1.21 mL of methyl iodide was replaced with 1.68 mL of allyl bromide, and an aromatic compound (Compound 10) having six allyl groups, as shown in the following formula, was obtained as a white solid (2.59 g).

[0343]

[0344] １ H-NMR (CDCl ３ , 400MHz): 2.24 (s, 2H), 2.48-2.76 (m, 8H), 5.04-5.20 (m, 8H), 5.48-5.68 (m, 4H), 7.55 (q ＡＢ , J=8.92Hz, 8H) １９ F-NMR (CDCl ３ , 400MHz): -110.0 to -110.7 (m, 4F), -120.9 to -121.5 (m, 4F), -121.5 to -122.1 (m, 4F)

[0345] Synthesis Example 11 Synthesis Example 11-1 of Compound 11 Synthesis of Intermediate (M-6) 7.20 g of 1,6-diiodoperfluorohexane, 5.76 g of 5-bromo-1-indanone, 0.406 g of 2,2'-bipyridyl, and 4.96 g of copper powder were placed in a reaction vessel, purged with nitrogen, and 33 mL of DMSO was added and stirred. The mixture was reacted at 85°C for 20 hours. Chloroform and water were added to the reaction mixture and filtered by Celite. The organic layer was washed with dilute hydrochloric acid and saturated brine. After solvent removal, the crude product was washed with methanol to obtain the aromatic compound shown in the following formula (intermediate (M-6)).

[0346]

[0347] Example 11-2 Synthesis of intermediate (M-7) 5.40 g of intermediate (M-6) was placed in a reaction vessel and suspended in 43.2 mL of THF, and stirred at 45°C. 1.852 g of sodium borohydride was added and the reaction was carried out for 18 hours. The reaction mixture was cooled to 5°C and quenched with dilute hydrochloric acid. Extraction was performed with ethyl acetate, and the organic layer was washed with saturated brine. The solvent was removed by distillation to obtain the aromatic compound represented by the following formula (M-7) (intermediate (M-7)).

[0348]

[0349] Example 11-3 5.32 g of intermediate (M-7) was placed in a reaction vessel for the synthesis of compound 11 and suspended in 61.7 mL of toluene. 0.178 g of p-toluenesulfonic acid monohydrate was added, and the mixture was heated under reflux at 130°C for 2 hours. 5% sodium bicarbonate solution was added to the reaction mixture and stirred. The mixture was then extracted with diethyl ether, and the organic layer was washed with water and saturated brine. After solvent removal, the mixture was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain a compound having an indenyl group (compound 11), represented by the following formula, as a white solid (2.61 g).

[0350] １ H-NMR (CDCl ３ , 400MHz): 3.45 (s, 4H), 6.60-6.80 (m, 2H), 6.84-7.01 (m, 2H), 7.36-7.58 (m, 4H), 7.66 (s, 2H) １９ F-NMR (CDCl ３ , 376MHz): -108.6 to -110.0 (m, 4F), -119.5 to -122.6 (m, 8F)

[0351] Synthesis Example 12: Based on Example 4 of Japanese Patent No. 6374867, an aromatic compound having a perfluorovinyl group represented by the following formula was synthesized.

[0352] Synthesis Example 13 Synthesis Example 13-1 of Compound 13 In a reaction vessel for the synthesis of intermediate (M-8), 45.0 g of copper(II) chloride was placed, and 670 mL of ethanol was added and stirred until dissolved. A solution of 60.4 g of 1,10-phenanthroline dissolved in 670 mL of ethanol was added and stirred for 30 minutes. The precipitated blue-green solid was filtered off, washed with ethanol, and dried. 43.9 g of the obtained solid was placed in a reaction vessel, and 1120 mL of anhydrous THF was added and stirred. Then 26.8 g of sodium-tert-butoxide was added and stirred for a further 10 minutes. To this suspension, a solution of 35.4 g of bispinacol diborane and 24.7 g of 3,3,4,4,5,5,6,6-octafluoro-6-iodohexa-1-ene dissolved in THF (280 mL) was added dropwise over 30 minutes. After stirring for 1 hour, the suspension was filtered through Celite and concentrated to obtain 51.6 g of the crude solid product. 400 mL of hexane was added to the obtained solid, filtered, washed with hexane, and dried under reduced pressure to obtain 4.74 g of the brown solid intermediate (M-8).

[0353] Example 13-2 Synthesis of Compound 13 In a glove box, 4.0 g of intermediate (M-8), 0.39 g of 1,3,5-triiodobenzene, and 8.0 mL of anhydrous THF were added to the reaction vessel. After stirring overnight at 80°C outside the glove box, water was added to quench the mixture, and the mixture was filtered by Celite while washing with chloroform. After liquid-liquid separation of the filtrate, the aqueous layer was extracted with chloroform, and the solvent was removed by distillation to obtain 0.83 g of a black oily crude product. The crude product was purified by silica filtration and preparative GPC to obtain the target product shown in the following formula as a colorless oil (0.19 g).

[0354]

[0355] １ H-NMR (CDCl ３ , 400MHz): 5.72-5.87 (m, 3H), 5.87-6.06 (m, 6H), 8.00 (s, 3H) １９ F-NMR (CDCl ３ , 376MHz): -110.8 to -111.8 (m, 6F), -113.5 to -114.4 (m, 6F), -121.0 to -122.1 (m, 6F), -122.5 to -123.5 (m, 6F)

[0356] Synthesis Example 14 Synthesis of Compound 14 In a glove box, 1.0 g of intermediate (M-8), 0.13 g of tris(4-iodophenyl)amine, and 2.6 mL of anhydrous DMF were added to the reaction vessel. After stirring overnight at 100°C outside the glove box, the mixture was filtered by Celite. After concentrating the filtrate, chloroform and water were added to the residue and liquid-liquid was separated. The organic layer was concentrated to obtain 0.18 g of a black oily crude product. The crude product was purified by silica filtration and preparative GPC to obtain the target product shown in the following formula as a brown oil (0.12 g).

[0357]

[0358] １ H-NMR (CDCl ３ , 400MHz): 5.75-5.80 (m, 3H), 5.92-6.07 (m, 6H), 7.18 (d, J = 8.8Hz, 6H), 7.50 (d, J = 8.8Hz, 6H) １９ F-NMR (CDCl ３ , 376MHz): -110.7 to -111.3 (m, 6F), -114.0 to -114.9 (m, 6F), -121.5 to -122.6 (m, 6F), -123.0 to -124.0 (m, 6F)

[0359] The values ​​in each example were measured using the following method.

[0360] (Monomer composition) １９ This was determined by F-NMR analysis.

[0361] (Iodine content) Measured by elemental analysis.

[0362] (Mooney Viscosity) The Mooney viscometer was measured at 100°C using an ALPHA TECHNOLOGIES MV2000E model, in accordance with JIS K6300.

[0363] (Crosslinking Properties) For the fluorine-containing elastomer compositions produced in the examples and comparative examples, the temperature dispersion (40-230°C) was measured using an ALPHA TECHNOLOGIES RPA2000 at a strain of 10% and a frequency of 1 Hz. The lowest value of the loss tangent tanδ above 150°C was used as an indicator of the degree of crosslinking. A smaller tanδ indicates greater elasticity and higher crosslinking ability.

[0364] (Heat resistance test) After evaluating the crosslinking properties, the samples were heated in an electric furnace at 300°C for 72 hours. The heat-treated samples and the unheat-treated samples were subjected to C ４ F ８ Cl ２ The samples were immersed in a fluorine-containing solvent with as the main component for 72 hours at room temperature, then removed and their volume was immediately measured. Since the samples swelled upon immersion, the change in volume from before immersion was calculated as the swelling rate using the following formula: Swelling rate (%) = ((Volume after immersion) - (Volume before immersion)) / (Volume before immersion) × 100 Change in swelling rate (%) = (Swelling rate after heat treatment) - (Swelling rate before heat treatment)

[0365] The swelling rate correlates with the crosslink density; the higher the crosslink density, the smaller the swelling rate. When molecular chains or crosslinking points are cleaved by heat treatment, the crosslink density of the sample decreases after heat treatment compared to the untreated sample, resulting in a larger swelling rate. Therefore, the smaller the change in swelling rate before and after heat treatment, the less likely molecular chains or crosslinking points are to be cleaved at high temperatures, indicating superior heat resistance.

[0366] (Compression Set) The compression set was measured according to the method described in ASTM D395 or JIS K6262. The O-ring was compressed to a compression ratio of 25% at room temperature using a compression device (an O-ring with a thickness (wire diameter) of 3.5 mm was compressed to a thickness of 2.625 mm).

[0367] Next, the compression device with the compressed O-ring fixed in place was left in an electric furnace at 200°C or 250°C for 72 hours and 168 hours, respectively, before being removed from the electric furnace. The O-ring was removed from the compression device, and the removed O-ring was left in a constant temperature room at 23°C for 30 minutes, after which the thickness of the O-ring (t2) was measured. The compression set was calculated using the following formula: Compression set rate (%) = (t0 - t2) / (t0 - t1) × 100 t0: Original thickness of the O-ring (mm) t1: Thickness of the spacer (mm) t2: Thickness of the O-ring after the compression test (mm) In the above test, t0 = 3.5 mm and t1 = 2.625 mm.

[0368] The compression set is a value that indicates the heat-sealing ability of a sealant; the higher the heat resistance of the sealant, the lower the compression set. Therefore, the lower the compression set after heat treatment, the higher the heat resistance.

[0369] The following materials were used in the examples and comparative examples: Fluorine-containing elastomer: TFE / PMVE / CF ２ = CFOCF ２ CF ２ CH ２ I copolymer TFE / PMVE / CF ２ = CFOCF ２ CF ２ CH ２ I (mol%): 67.2 / 32.6 / 0.2 Iodine content: 0.4% by mass Mooney viscosity ML (1+10) (100℃): 64 MT carbon: Thermax N-990 Cancarb Perhexa® 25B: 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, manufactured by NOF Corporation

[0370] 1. Crosslinking evaluation: Fluorine-containing polymer (100 parts by mass), compounds 1-7, 11, 12, 13, 14 and triallyl isocyanurate (TAIC) as crosslinking aids (amounts shown in Tables 1 and 2), Perhexa 25B (2 parts by mass), MT carbon (15 parts by mass), C ４ F ８ Cl ２ The mixture was mixed in a fluorine-containing solvent with the main component and subjected to ultrasonic treatment for 30 minutes. The fluorine-containing solvent was evaporated at 23°C to obtain fluorine-containing elastomer compositions 1 to 16. The temperature dispersion (40 to 230°C) of the obtained fluorine-containing elastomer compositions at a strain of 10% and a frequency of 1 Hz was measured using an RPA2000.

[0371] The minimum value of the loss tangent tanδ at temperatures above 150°C was measured, and the evaluation criteria were as follows. The results are shown in Tables 1 and 2. VG: Minimum tanδ value less than 0.05 G: Minimum tanδ value between 0.05 and 0.08 NG: Minimum tanδ value of 0.08 or higher

[0372] 2. Heat Resistance Evaluation A heat resistance test was performed on the samples obtained after the crosslinking property evaluation. The swelling rate before heating and the change in swelling rate after heat treatment at 300°C for 72 hours were measured. The evaluation criteria were as follows. The results are shown in Tables 1 and 2. (Swelling rate before heating) G: Swelling rate less than 150% NG: Swelling rate 150% or more (Change in swelling rate) VG: Change in swelling rate less than 150% G: Change in swelling rate 150% or more, less than 600% NG: Change in swelling rate 600% or more

[0373]

[0374]

[0375] 3. Measurement of compression set The fluorine-containing elastomer compositions 1, 2, 6, 8-10, and 13-16 obtained in 1. were pressed at 170°C for 30 minutes to crosslink, and then oven-crosslinked in an electric furnace at 250°C for 4 hours to obtain molded articles (O-rings). The compression set of the obtained molded articles was measured. The composition containing TAIC was pressed at 160°C for 10 minutes to crosslink, and then oven-crosslinked in an electric furnace at 180°C for 4 hours to obtain molded articles (O-rings).

[0376] The compression set of molded articles obtained from fluorine-containing elastomer compositions 1, 2, 6, 8, 9, and 13-16 was measured after being compressed at 200°C for 72 hours. The measurement results are shown in Table 3.

[0377] The compression set rates were measured for molded articles obtained from fluorine-containing elastomer compositions 1, 2, 9, 10, and 13-16 after being compressed at 250°C for 72 hours and 168 hours. The measurement results are shown in Table 4. The "-" in Comparative Example 4 indicates that the test sample did not recover from compression, and therefore the thickness could not be measured and calculated.

[0378]

[0379]

[0380] Tables 1 and 2 show the tanδ and swelling rate measurements in fluorine-containing solvents before heat treatment. These results suggest that when the compound of this disclosure is used as a crosslinking aid, it exhibits higher crosslinking ability and solvent resistance compared to compound 12. Furthermore, it was confirmed that when the compound of this disclosure is used as a crosslinking aid, the change in swelling rate is smaller and the heat resistance is higher compared to TAIC. Table 3 shows that, compared to compound 12, which has high heat resistance but low crosslinking ability, using the compound of this disclosure results in a lower compression set of the resulting molded article. As shown in Table 4, when the compound of this disclosure is used, the compression set values ​​and the increase in compression set of the molded article after 72 hours and 168 hours of standing were suppressed compared to when compound 12 and TAIC were used. These results indicate that when the compound of this disclosure is used as a crosslinking aid, it exhibits high crosslinking ability and high heat resistance of the molded article.

Claims

A crosslinking aid represented by general formula (11). General form (11): (In the formula, X １ , X ２ each independently represent H, F, OH, a non-fluorinated alkyl group optionally having one or more substituents, a fluorinated alkyl group optionally having one or more substituents, a non-fluorinated alkoxy group optionally having one or more substituents, a fluorinated alkoxy group optionally having one or more substituents, or a group represented by general formula: -(O) ｒ -(CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ wherein r is 0 or 1, and l is an integer of 1 to 10, Y １ , Y ２ , Y ３ H or F, independently Z represents a single bond, -NH-, -NR- (R is an alkyl group with 1 to 6 carbon atoms), -O-, -S-, -CO-, -SO ２ - A non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents, m is an integer from 1 to 10, independently. n is an independent integer from 1 to 5. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. 　 A crosslinking aid according to claim 1, represented by general formula (12). General form (12): (In the formula, X １ , X ２ H or F, independently Z is a single bond or a fluorinated alkylene group which may have one or more substituents. m is an integer from 1 to 10, independently. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. A crosslinking aid according to claim 1, represented by general formula (13). General form (13): (In the formula, X １ , X ２ H or F, independently X ３ These are independently OH, a nonfluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｋ -CH=CH ２ (wherein the formula r is 0 or 1, and k is an integer from 1 to 10) the base represented by, X ４ Independently, the general formula is: -(CX １ X ２ ) ｌ -CH=CH ２ The base represented by (where l is an integer from 1 to 10 in the formula), Z is a single bond or a fluorinated alkylene group which may have one or more substituents. m is an integer from 1 to 10, independently. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. 　 A crosslinking aid represented by general formula (21). General form (21): (In the formula, X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ (wherein the formula r is 0 or 1, l is an integer from 1 to 10) the base represented by, Y １ , Y ２ , Y ３ H or F, independently Z １ is a benzene ring, N, or CX' (where X' is OH, F, or H), m is an integer from 1 to 10, independently. p is 0 or 1. Z １ If it is a benzene ring, then q is an integer from 2 to 6, Z １ If is N or CX', then q is 3. It represents. Z １ If it is a benzene ring, then p is either all 0 or all 1, Z １ If is N or CX', then all p are 1. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. 　 A crosslinking aid according to claim 4, represented by general formula (22). General form (22): (In the formula, X １ , X ２ H or F, independently m is an integer from 1 to 10, independently. p is 0 or 1. q is an integer between 2 and 6. It represents. 　 p is either all zeros or all ones. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. 　 A crosslinking aid represented by general formula (31). General form (31): (In the formula, X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ (wherein the formula r is 0 or 1, l is an integer from 1 to 10) the base represented by, Y １ , Y ２ , Y ３ H or F, independently Z represents a single bond, -NH-, -NR- (R is an alkyl group with 1 to 6 carbon atoms), -O-, -S-, -CO-, -SO ２ - A non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents, m is an integer from 1 to 10, independently. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. 　 A crosslinking aid according to claim 6, represented by general formula (32). General form (32): (In the formula, X １ , X ２ H or F, independently Z is a single bond or a fluorinated alkylene group which may have one or more substituents. m is an integer from 1 to 10, independently. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. 　 A composition containing a crosslinking aid according to any one of claims 1 to 7, and a fluorine-containing polymer. 　 The composition according to claim 8, wherein the amount of the crosslinking aid is 0.1 to 10 parts by mass per 100 parts by mass of the fluorine-containing polymer. 　 The composition according to claim 8 or 9, wherein the fluorine-containing polymer is a fluorine-containing elastomer. 　 The composition according to any one of claims 8 to 10, wherein the fluorine-containing polymer contains an iodine atom or a bromine atom. 　 The composition according to any one of claims 8 to 11, further comprising an organic peroxide. 　 The composition according to claim 12, wherein the content of the organic peroxide is 0.05 to 10 parts by mass per 100 parts by mass of the fluorine-containing polymer. 　 A crosslinked fluorine-containing polymer obtained by crosslinking the composition according to any one of claims 8 to 13. 　 A molded article obtained from a crosslinked fluorine-containing polymer as described in claim 14. 　 A molded article according to claim 15, which is a sealing material. A compound represented by general formula (11a). General form (11a): (In the formula, X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ (wherein the formula r is 0 or 1, l is an integer from 1 to 10) the base represented by, Y １ , Y ２ , Y ３ H or F, independently Z represents a single bond, -NH-, -NR- (R is an alkyl group with 1 to 6 carbon atoms), -O-, -S-, -CO-, -SO ２ - A non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents, m is an integer from 1 to 10, independently. n is an independent integer from 1 to 5. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. However, X １ , X ２ However, this excludes compounds in which all are F, Z is a single bond, and m is 1. X １ , X ２ , Y １ , Y ２ , Y ３ If either of them is H, and both are H, then Z is a fluorinated alkylene group which may have one or more substituents. 　 The compound according to claim 17, represented by general formula (14). General form (14): (In the formula, X １ , X ２ H or F, independently X ３ independently represents OH, a non-fluorinated alkoxy group which may have one or more substituents, or a group represented by the general formula: -(O) ｒ -(CX １ X ２ ) ｋ -CH=CH ２ wherein r is 0 or 1, and k is an integer of 1 to 10, X ４ Independently, the general formula is: -(CX １ X ２ ) ｌ -CH=CH ２ The base represented by (where l is an integer from 1 to 10 in the formula), m is an integer from 1 to 10, independently. s is an integer from 1 to 10. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. 　 The compound according to claim 17, represented by general formula (15). General form (15): (In the formula, m is an integer from 1 to 10, independently. s is an integer from 1 to 10. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. 　 The compound according to claim 17, represented by general formula (16). General form (16): (In the formula, m is an integer from 2 to 10, independently. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. The compound according to claim 17, represented by general formula (17). General form (17): (In the formula, m is an integer from 1 to 10, independently. s is an integer from 1 to 10. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. 　 A compound represented by general formula (21a). General form (21a): (In the formula, X １ and X ２ are each independently H, F, OH, a non-fluorinated alkyl group optionally having one or more substituents, a fluorinated alkyl group optionally having one or more substituents, a non-fluorinated alkoxy group optionally having one or more substituents, a fluorinated alkoxy group optionally having one or more substituents, or a group represented by the general formula: -(O) ｒ -(CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ (wherein r is 0 or 1, and l is an integer of 1 to 10), Y １ , Y ２ , Y ３ H or F, independently Z １ is a benzene ring, N, or CX' (where X' is OH, F, or H), m is an integer from 1 to 10, independently. p is 0 or 1. Z １ If it is a benzene ring, then q is an integer from 2 to 6, Z １ If is N or CX', then q is 3. It represents. Z １ If it is a benzene ring, then p is either all 0 or all 1, Z １ If is N or CX', then all p are 1. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. However, X １ , X ２ , Y １ , Y ２ , Y ３ (One of them is H, and not all of them can be H.) The compound according to claim 22, which is a compound represented by general formula (22a). General form (22a): (In the formula, m is an integer from 1 to 10, independently. p is 0 or 1. q is an integer between 2 and 6. It represents. 　 p is either all zeros or all ones. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. A compound represented by general formula (31a). General form (31a): (In the formula, X １ , X ２ These are independently H, F, OH, a non-fluorinated alkyl group which may have one or more substituents, a fluorinated alkyl group which may have one or more substituents, a non-fluorinated alkoxy group which may have one or more substituents, a fluorinated alkoxy group which may have one or more substituents, or the general formula: -(O) ｒ - (CX １ X ２ ) ｌ -CY １ =CY ２ Y ３ (wherein the formula r is 0 or 1, l is an integer from 1 to 10) the base represented by, Y １ , Y ２ , Y ３ H or F, independently Z is -O-, -S-, -CO-, -SO ２ - A non-fluorinated alkylene group which may have one or more substituents, or a fluorinated alkylene group which may have one or more substituents, m is an integer from 1 to 10, independently. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent. 　 The compound according to claim 24, which is a compound represented by general formula (33). General form (33): (In the formula, s is an integer from 1 to 10. It represents. The hydrogen atoms bonded to the benzene ring may be substituted with any substituent.

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