Fluoropolyether compound

Abstract

To provide a compound having sufficient compatibility with a monomer and sufficient curability.SOLUTION: Provided is a fluorine-containing compound represented by formula (S1), (S2), or (S3) [where RF1 independently represents a monovalent organic group containing a fluorine atom; RF2 independently represents a divalent organic group containing a fluorine atom; L1 independently represents a group containing a monovalent radical-generating group; and L2 independently represents a group containing a divalent radical-generating group], where the fluorine content is 50 mass% or more, the fluorine-to-oxygen content ratio is 2.0 to 10.0, and the minimum interatomic bond dissociation energy is 300 kJ / mol or less.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present disclosure relates to novel fluoropolyether compounds. [Background technology]

[0002] Although various compounds are known as polymerization initiators, there are few examples of polymerization initiators containing fluorine atoms. For example, Patent Document 1 discloses a polymerization initiator having a site that generates radicals by light via a linker containing an amide bond. Patent Document 1 also discloses a polymer that generates radicals by light. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2021 / 229331 Summary of the Invention [Problem to be solved by the invention]

[0004] When the compound described in Patent Document 1 is used as a polymerization initiator, it cannot be said that it has sufficient compatibility with monomers and curability. [Means for solving the problem]

[0005] The present disclosure includes the following aspects. [1] Formula (S1), (S2) or (S3): [ka] [In formula: R F1 each independently represents a monovalent organic group containing a fluorine atom, R F2 each independently represents a divalent organic group containing a fluorine atom, L 1 are each independently a monovalent radical-forming group, L 2 are each independently a group containing a divalent radical-forming group. A fluorine-containing compound represented by the formula: The fluorine content is 50% by mass or more, The fluorine content / oxygen content ratio is 2.0 to 10.0; The minimum bond dissociation energy between atoms is 300 kJ / mol or less. Fluorine-containing compound. [2] L 1 are each independently -X 1 -L R1 and X 1 is a divalent group having no single bond or no amide bond, L R1 is a monovalent radical-forming group, The fluorine-containing compound according to the above item [1]. [3] X 1 are each independently Single bond, C 1-6 an alkylene group, or -(CH 2 ) z1 -O-(CH 2 ) z2 - [In the formula, z1 is an integer from 0 to 6, z2 is an integer from 0 to 6, Here, at least one of z1 and z2 is 1 or more. The fluorine-containing compound according to the above item [2], [4] L 1 are each independently -X 1 -L R1 and X 1 each independently represents a single bond or the following formula: -(R 51 ) p5 -(R 52 ) q5 - [In formula: R 51 is a single bond, C1-20 an alkylene group, or an o-, m- or p-phenylene group; R 52 each independently represents -O-, -S-, o-, m- or p-phenylene group, -COO-, -OCO-, -CONR 54 -, -NR 54 CO-, -O-CONR 54 -, -NR 54 CO-O- and -NR 54 - is a group selected from the group consisting of R 54 are each independently a hydrogen atom, a phenyl group, or C 1-6 is an alkyl group, p5 is an integer from 0 to 6; q5 is an integer from 0 to 6, wherein at least one of p5 and q5 is 1 or more, and the order of the repeating units enclosed in parentheses with p5 or q5 is arbitrary. is a divalent organic group represented by L R1 is a monovalent radical-forming group, The fluorine-containing compound according to the above item [1]. [5] X 1 are each independently Single bond, C 1-6 an alkylene group, or -(CH 2 ) z1 -R 53 -(CH 2 ) z2 - [In the formula, R 53 -O, -COO-, -OCO-, -CONR 54 - or -NR 54 CO-, R 54 are each independently a hydrogen atom, a phenyl group, or C 1-6 is an alkyl group, z1 is an integer from 0 to 6, z2 is an integer from 0 to 6, Here, at least one of z1 and z2 is 1 or more. The fluorine-containing compound according to the above item [4], [6] L 2 -R 2 -R 4 -L R2 -R 4 -R 2 - is a group represented by R 2 each independently represents an alkylene group, an oxygen atom, -COO-, -OCO-, or -CONR 11 - or -NR 11 CO-, R 11 is a hydrogen atom or C 1-6 is an alkyl group, R 4 are each independently a single bond or a divalent organic group, L R2 The fluorine-containing compound according to any one of the above [1] to [5], wherein: is a divalent radical-forming group. [7] The monovalent radical-forming groups are each independently one of the following groups: [ka] [In formula: Y is a single bond or a divalent organic group; W 1 is an oxygen atom or NR 25 and W 2 OR 25 , or NR 25 2 and R 25 are each independently a hydrogen atom or a hydrocarbon group, R 20 is a hydrogen atom or a monovalent organic group, R 22 are each independently a hydrogen atom or a monovalent organic group, R 23 are each independently a hydrogen atom or a monovalent organic group, R 24 are each independently a hydrogen atom or a monovalent organic group, Ar 1 is an arylene group, Ar 2 is an aryl group, However, R in the formula 22 and R 22 , R 23 and R 23 , R 24 and R 24 , R 25 and R 25 , or Ar 1 and Ar 2 is optionally linked via a linker L, L is a single bond or C 1-6 -(C s H 2s ) x -(X 3 ) y -(C t H 2t ) z -, phenylene, or naphthylene; X 3 is O, S, or NH; s is an integer from 1 to 6; t is an integer from 1 to 6; x, y, and z are each independently 0 or 1; However, at least one of x, y, and z is 1. The fluorine-containing compound according to any one of the above [1] to [6], [8] The divalent radical-forming groups are each independently one of the following groups: [ka] [In formula: Y is a single bond or a divalent organic group; W 1 is an oxygen atom or NR 25 and W 2 OR 25 , or NR 25 2 and R 22is a hydrogen atom or a monovalent organic group, R 23 are each independently a hydrogen atom or a monovalent organic group, or two R 23 may be bonded to form a ring, R 24 is a hydrogen atom or a monovalent organic group, R 25 is a hydrogen atom, an oxygen atom, or a hydrocarbon group, R 26 is a divalent organic group, Ar 1 are each independently an arylene group; However, R in the formula 23 and R 23 , R 25 and R 25 , or Ar 1 and Ar 1 is optionally linked via a linker L, L is a single bond or C 1-6 -(C s H 2s ) x -(X 3 ) y -(C t H 2t ) z -, phenylene, or naphthylene; X 3 is O, S, or NH; s is an integer from 1 to 6; t is an integer from 1 to 6; x, y, and z are each independently 0 or 1; However, at least one of x, y, and z is 1. The fluorine-containing compound according to any one of the above [1] to [7], wherein the group comprises: [9] The divalent radical-forming group is the following group: [ka] [In formula: Ar 5each independently represents a phenyl group which may have a substituent, Ar 6 each independently represents a phenylene group which may have a substituent, R 31 are each independently 1-6 is a hydrocarbon group, R 32 each independently represents a single bond or C 1-6 is an alkylene group. The fluorine-containing compound according to any one of the above [1] to [8],

[10] The fluorine-containing compound according to any one of the above [1] to [9], wherein the monovalent radical-forming group and the divalent radical-forming group are groups that generate radical species when irradiated with light having a wavelength of 200 to 500 nm.

[11] R F1 are each independently R F3 -(Z 1 -R F4 ) k - and R F2 are each independently -R F4 -(Z 1 -R F4 ) k - and R F3 are each independently Rf 1 -R F -O q - and R F4 are each independently -Rf 2 p -R F -O q - and Rf 1 C may be substituted with one or more fluorine atoms 1-16 is an alkyl group, Rf 2 C may be substituted with one or more fluorine atoms 1-6 is an alkylene group, R F are each independently a divalent fluoropolyether group, p is 0 or 1; Each q is independently 0 or 1; Z 1 are each independently a single bond or a divalent organic group, Each k is independently an integer of 0 to 20. The fluorine-containing compound according to any one of the above items [1] to

[10] .

[12] Z 1 each independently represents a group containing a divalent radical-forming group.

[13] R F are each independently represented by the following formula (f1), (f2), (f3), (f4), (f5), or (f6): -(OC 3 F 6 ) d -(OC 2 F 4 ) e - (f1) [In the formula, d is an integer of 1 to 200, and e is 0 or 1.] -(OC 4 F 8 ) c -(OC 3 F 6 ) d -(OC 2 F 4 ) e -(OCF 2 ) f - (f2) [In the formula, c and d each independently represent an integer of 0 to 30; e and f each independently represent an integer of 1 to 200; The sum of c, d, e, and f is an integer of 10 to 200; The order of occurrence of each repeat unit enclosed in parentheses with the subscript c, d, e, or f is arbitrary in the formula. -(R 6 -R 7 ) g - (f3) [In the formula, R 6 is OCF 2 Or O.C. 2 F4 and; R 7 is O.C. 2 F 4 , O.C. 3 F 6 , O.C. 4 F 8 , O.C. 5 F 10 and O.C. 6 F 12 or a combination of two or three groups selected from these groups; g is an integer from 2 to 100. -(R 6 -R 7 ) g -R r -(R 7’ -R 6’ ) g’ - (f4) [In the formula, R 6 is OCF 2 Or O.C. 2 F 4 and R 7 is O.C. 2 F 4 , O.C. 3 F 6 , O.C. 4 F 8 , O.C. 5 F 10 and O.C. 6 F 12 or a combination of two or three groups independently selected from these groups; R 6’ is OCF 2 Or O.C. 2 F 4 and R 7’ is O.C. 2 F 4 , O.C. 3 F 6 , O.C. 4 F 8 , O.C. 5 F 10 and O.C. 6 F 12or a combination of two or three groups independently selected from these groups; g is an integer from 2 to 100; g' is an integer from 2 to 100, R r teeth, [ka] (In the formula, * indicates the bond position.) .]; -(OC 6 F 12 ) a -(OC 5 F 10 ) b -(OC 4 F 8 ) c -(OC 3 F 6 ) d -(OC 2 F 4 ) e -(OCF 2 ) f - (f5) [In the formula, e is an integer of 1 or more and 200 or less, a, b, c, d, and f are each independently an integer of 0 or more and 200 or less, the sum of a, b, c, d, e, and f is at least 1, and the order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula.] -(OC 6 F 12 ) a -(OC 5 F 10 ) b -(OC 4 F 8 ) c -(OC 3 F 6 ) d -(OC 2 F 4 ) e -(OCF 2 ) f - (f6) [In the formula, f is an integer of 1 or more and 200 or less, a, b, c, d, and e are each independently an integer of 0 or more and 200 or less, the sum of a, b, c, d, e, and f is at least 1, and the order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula.] The fluorine-containing compound according to the above item

[11] , wherein the R is a group represented by the following formula:

[14] The fluorine-containing compound according to any one of the above [1] to

[13] , which has a number average molecular weight of 1,000 to 100,000.

[15] The fluorine-containing compound according to any one of the above [1] to

[14] , wherein the lowest bond dissociation energy among the bond dissociation energies for each bond in the fluorine-containing compound is 185 kJ / mol or less.

[16] (i) A fluorine-containing compound according to any one of the above [1] to

[15] , and (ii) Fluorine-containing polymerizable monomer 1. A curable composition comprising:

[17] The curable composition according to the above

[16] , wherein the SP value of the fluorine-containing compound and the fluorine-containing polymerizable monomer is in the range of 6.0 to 7.4.

[18] The curable composition according to

[16] or

[17] above, having a solvent content of 20% by weight or less.

[19] The curable composition according to any one of the above

[16] to

[18] , wherein the fluorine-containing polymerizable monomer is a compound having a fluoropolyether group and a (meth)acrylate group.

[20] The fluorine-containing polymerizable monomer is represented by the following formula (M): (CH 2 =CR 71 -O-) m1 -X 7 -R F72 -X 7 -(OCO-CR 71 =CH 2 ) m1 [In formula: R F72 is -Rf 2 p -R F -O q- and Rf 2 C may be substituted with one or more fluorine atoms 1-6 is an alkylene group, R F are each independently a divalent fluoropolyether group, p is 0 or 1; Each q is independently 0 or 1; R 71 are each independently a hydrogen atom or C 1-6 is an alkyl group, X 7 are each independently a divalent to pentavalent organic group, Each m1 is independently an integer of 1 to 4. The curable composition according to any one of the above

[16] to

[19] , wherein the compound is represented by the following formula:

[21] The curable composition according to any one of the above

[16] to

[20] , wherein the fluorine-containing compound is used in an amount of 0.1 to 50 parts by mass per 100 parts by mass of the fluorine-containing polymerizable monomer.

[22] A cured product obtained by curing the curable composition described in any one of the above

[16] to

[21] .

[23] Mixing the fluorine-containing compound according to any one of the above [1] to

[15] with a fluorine-containing polymerizable monomer to obtain a mixture. A method for producing a cured product, comprising irradiating the mixture with light having a wavelength of 200 to 500 nm to obtain a cured product.

[24] The method for producing a cured product according to the above

[23] , wherein the mixture has a solvent content of 20 mass% or less.

[25] Equation (S3a): AR F2 -A [In formula: R F2 is a divalent organic group containing a fluorine atom, Each A is independently represented by the following formula: [ka] (In the formula, R 23 are each independently a hydrogen atom or a monovalent organic group, or two R 23 may be bonded to form a ring, Y is a single bond or a divalent organic group; However, R 23 At least one of Y does not contain a phenyl group. It is a group containing a group represented by the following formula: A compound represented by the formula:

[26] Each A is independently -R 7 -R 8 -R 9 and R 7 is an alkylene group, an oxygen atom, -COO-, or -CONR 11 - and R 11 is a hydrogen atom or C 1-6 is an alkyl group, R 8 is a single bond or a divalent organic group, R 9 is expressed by the following formula: [ka] (In the formula, R 23 are each independently a hydrogen atom or a monovalent organic group, or two R 23 may be bonded to form a ring, Y is a single bond or a divalent organic group; However, R 23 At least one of Y does not contain a phenyl group. is a group represented by The compound according to the above

[25] .

[27] R F2 are each independently -R F4 -(Z 1 -R F4 ) k - and R F4 are each independently -Rf 2 p -RF -O q - and Rf 2 C may be substituted with one or more fluorine atoms 1-6 is an alkylene group, R F are each independently a divalent fluoropolyether group, p is 0 or 1; Each q is independently 0 or 1; Z 1 are each independently a single bond or a divalent organic group, Each k is independently an integer of 0 to 20. The compound according to any one of the above

[25] and

[26] . Effect of the Invention

[0006] According to the present disclosure, it is possible to provide a novel compound containing a fluoropolyether group that has excellent compatibility with a fluorine-based polymerizable monomer. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] As used herein, the term "monovalent organic group" refers to a monovalent group containing carbon. The monovalent organic group may be a hydrocarbon group or a derivative thereof, unless otherwise specified. The derivative of a hydrocarbon group refers to a group having one or more N, O, S, Si, amide, sulfonyl, siloxane, carbonyl, carbonyloxy, etc. at the end or in the molecular chain of the hydrocarbon group. In addition, when simply referring to an "organic group", it refers to a monovalent organic group. In addition, the term "divalent organic group" refers to a divalent group containing carbon. Such a divalent organic group is not particularly limited, but includes a divalent group obtained by further removing one hydrogen atom from a monovalent organic group.

[0008] As used herein, the term "hydrocarbon group" refers to a group containing carbon and hydrogen, which is a group obtained by removing one hydrogen atom from a hydrocarbon. Such a hydrocarbon group includes, but is not limited to, C1-20 Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The "aliphatic hydrocarbon group" may be linear, branched, or cyclic, and may be saturated or unsaturated. The hydrocarbon group may contain one or more ring structures. The hydrocarbon group may be substituted with one or more substituents.

[0009] As used herein, examples of the substituent of the "hydrocarbon group" include, but are not limited to, a halogen atom, a C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 Alkynyl group, C 3-10 Cycloalkyl groups, C 3-10 Unsaturated cycloalkyl groups, 5-10 membered heterocyclyl groups, 5-10 membered unsaturated heterocyclyl groups, C 6-10 Examples of the alkyl group include one or more groups selected from an aryl group and a 5- to 10-membered heteroaryl group.

[0010] (Fluorine-containing compounds) The present disclosure relates to a compound represented by the following formula (S1), (S2) or (S3): [ka] [In formula: R F1 each independently represents a monovalent organic group containing a fluorine atom, R F2 each independently represents a divalent organic group containing a fluorine atom, L 1 are each independently a monovalent radical-forming group, L 2 are each independently a group containing a divalent radical-forming group. A fluorine-containing compound represented by the formula: The fluorine content is 50% by mass or more, The fluorine content / oxygen content ratio is 2.0 to 10.0; The minimum bond dissociation energy between atoms is 300 kJ / mol or less. Provided is a fluorine-containing compound. 2 and R F2 are bonded to each other at both ends to form a ring compound.

[0011] Conventional initiators such as those used in Patent Document 1 have low compatibility with fluorine-based monomers, but the fluorine-containing compound of the present disclosure is a fluorine-containing cyclic polymer having a radical initiator moiety and has high compatibility with curable monomers. In addition, the fluorine-containing compound of the present disclosure can effectively cause the fluorine-based monomer to act even at a low concentration. In particular, the fluorine-containing compound of the present disclosure has high compatibility with fluorine-based monomers and exhibits high curability even when the amount of solvent is small or no solvent is used.

[0012] In addition, the compound represented by formula (S1) generates low molecular weight radicals and polymer radicals during radical generation. On the other hand, the compounds represented by formulas (S2) and (S3) basically generate polymer radicals. The generated radicals act as initiators and the curing reaction proceeds, so due to the difference in radical species, it is expected that the compounds represented by formulas (S2) and (S3) have higher chemical resistance and better curing efficiency than the compound represented by formula (S1).

[0013] The monovalent radical-forming group and divalent radical-forming group are groups capable of generating radical species upon light irradiation or heat treatment.

[0014] In one embodiment, the monovalent radical-generating group and the divalent radical-generating group may be a group that generates a radical species upon irradiation with light having a wavelength of 200 to 500 nm.

[0015] In the above formula, L 1 are each independently a monovalent group containing a radical-forming group.

[0016] In a preferred embodiment, L 1 are each independently represented by the formula: -X 1-L R1 [In formula: X 1 are each independently a single bond or a group represented by the following formula: -(R 51 ) p5 -(R 52 ) q5 - (In the formula: R 51 is a single bond, C 1-20 an alkylene group, or an o-, m- or p-phenylene group; R 52 each independently represents -O-, -S-, o-, m- or p-phenylene group, -COO-, -OCO-, -CONR 54 -, -NR 54 CO-, -O-CONR 54 -, -NR 54 CO-O- and -NR 54 - is a group selected from the group consisting of R 54 are each independently a hydrogen atom, a phenyl group, or C 1-6 is an alkyl group, p5 is an integer from 0 to 6; q5 is an integer from 0 to 6, Here, at least one of p5 and q5 is 1 or more, and the order of the repeating units enclosed in parentheses with p5 or q5 is arbitrary. is a divalent organic group represented by L R1 is a monovalent radical-forming group. It is a group represented by the following formula:

[0017] In one embodiment, X 1 is a single bond.

[0018] In another embodiment, X 1 is -(R 51 ) p5 -(R 52 ) q5 - is a group represented by the formula:

[0019] R 51is preferably C 1-20 An alkylene group, or an o-, m- or p-phenylene group, more preferably C 1-20 It may be an alkylene group. 1-20 The alkylene group is preferably 1-10 Alkylene group, more preferably C 1-6 It may be an alkylene group. Such an alkylene group may be a straight chain or a branched chain.

[0020] R 52 is preferably -O-, -COO-, -OCO-, -CONR 54 -, -NR 54 CO-, -O-CONR 54 -, -NR 54 CO-O- or -NR 54 -, more preferably -COO-, -OCO-, -CONR 54 -, -NR 54 CO-, -O-CONR 54 - or -NR 54 CO-O-, more preferably -CONR 54 --It could be.

[0021] R 54 is preferably a hydrogen atom or C 1-6 It is an alkyl group.

[0022] In one embodiment, R 54 is a hydrogen atom.

[0023] In another embodiment, R 54 is C 1-6 Alkyl groups, preferably C 1-3 It is preferably an alkyl group, more preferably a methyl group. The alkyl group may be linear or branched.

[0024] In one embodiment, p5 is 0.

[0025] In another embodiment, p5 is an integer from 1 to 6, such as an integer from 1 to 3, or 1.

[0026] In one embodiment, q5 is 0.

[0027] In another embodiment, q5 is an integer from 1 to 6, such as an integer from 1 to 3, or 1.

[0028] In addition, X 1 In the case of two or more homogeneous R 52 are not consecutively combined.

[0029] In a preferred embodiment, X 1 are each independently Single bond, C 1-6 an alkylene group, or -(CH 2 ) z1 -R 53 -(CH 2 ) z2 - [In the formula, R 53 -O, -COO-, -OCO-, -CONR 54 - or -NR 54 CO-, R 54 are each independently a hydrogen atom, a phenyl group, or C 1-6 is an alkyl group, z1 is an integer from 0 to 6, z2 is an integer from 0 to 6, Here, at least one of z1 and z2 is 1 or more. It is a group represented by the following formula:

[0030] In another embodiment, X 1 is a divalent group that does not have a single bond or an amide bond.

[0031] In another preferred embodiment, X 1 are each independently Single bond, C 1-6 an alkylene group, or -(CH 2 ) z1 -O-(CH 2 ) z2 - [In the formula, z1 is an integer from 0 to 6, z2 is an integer from 0 to 6, Here, at least one of z1 and z2 is 1 or more. It is a group represented by the following formula:

[0032] L R1 is a monovalent radical-forming group.

[0033] The radical generating group is preferably the following group: [ka] [In formula: Y is a single bond or a divalent organic group; W 1 is an oxygen atom or NR 25 and W 2 OR 25 , or NR 25 2 and R 25 are each independently a hydrogen atom or a hydrocarbon group, R 20 is a hydrogen atom or a monovalent organic group, R 22 are each independently a hydrogen atom or a monovalent organic group, R 23 are each independently a hydrogen atom or a monovalent organic group, R 24 are each independently a hydrogen atom or a monovalent organic group, Ar 1 is an arylene group, Ar 2 is an aryl group, However, R in the formula 22 and R 22 , R 23 and R 23 , R 24 and R 24 , R 25 and R 25 , or Ar 1and Ar 2 is optionally linked via a linker L, L is a single bond or C 1-6 -(C s H 2s ) x -(X 3 ) y -(C t H 2t ) z -, phenylene, or naphthylene; X 3 is O, S, or NH; s is an integer from 1 to 6; t is an integer from 1 to 6; x, y, and z are each independently 0 or 1; However, at least one of x, y, and z is 1. is

[0034] In one embodiment, Y is a single bond.

[0035] In another embodiment, Y is a divalent organic group.

[0036] The divalent organic group is preferably C 1-10 It may be an alkylene group or a phenylene group, more preferably a phenylene group.

[0037] Above C 1-10 The alkylene group is preferably 1-6 Alkylene groups, such as C 2-6 It may be an alkylene group. The alkylene group may be a straight chain or a branched chain.

[0038] The phenylene group may be an o-, m- or p-phenylene group, preferably a p-phenylene group.

[0039] W 1 is an oxygen atom or NR 25 and preferably an oxygen atom.

[0040] W 2 OR 25 , or NR 25 2 and preferably OR 25 It is.

[0041] R 25 is a hydrogen atom or a hydrocarbon group.

[0042] In one embodiment, R 25 is a single bond.

[0043] In another embodiment, R 25 is a hydrocarbon group.

[0044] The hydrocarbon group is preferably C 1-6 An alkyl group or a phenyl group, more preferably C 1-6 It is an alkyl group.

[0045] Above C 1-6 The alkyl group is preferably C 1-3 It is preferably an alkyl group, more preferably a methyl group. The alkyl group may be linear or branched.

[0046] R 20 are each independently a hydrogen atom or a monovalent organic group.

[0047] In one embodiment, R 20 is a hydrogen atom.

[0048] In another embodiment, R 20 are each independently a monovalent organic group.

[0049] The monovalent organic group is preferably C 1-10 An alkyl group or an aryl group, preferably C 1-10 It may be an alkyl group.

[0050] Above C 1-10 The alkyl group is preferably C 1-6 Alkyl groups, more preferably C1-3 It may be an alkyl group, more preferably a methyl group. The alkyl group may be a straight chain or a branched chain.

[0051] The aryl group is preferably a phenyl group or a naphthyl group, more preferably a phenyl group.

[0052] R 22 are each independently a hydrogen atom or a monovalent organic group.

[0053] In one embodiment, R 22 is a hydrogen atom.

[0054] In another embodiment, R 22 is a monovalent organic group.

[0055] R 23 are each independently a hydrogen atom or a monovalent organic group.

[0056] In one embodiment, R 23 is a hydrogen atom.

[0057] In another embodiment, R 23 is a monovalent organic group.

[0058] R 24 are each independently a hydrogen atom or a monovalent organic group.

[0059] In one embodiment, R 24 is a hydrogen atom.

[0060] In another embodiment, R 24 is a monovalent organic group.

[0061] R 22 ~R 24 The monovalent organic group in is preferably an optionally substituted C 1-10 It may be an alkyl group, or an aryl group.

[0062] Above C1-10 The alkyl group is preferably C 1-6 Alkyl groups, more preferably C 1-3 It may be an alkyl group, more preferably a methyl group. The alkyl group may be a straight chain or a branched chain.

[0063] The aryl group is preferably a phenyl group or a naphthyl group, more preferably a phenyl group.

[0064] Ar 1 may be an arylene group, preferably a phenylene or naphthylene group, more preferably a phenylene group. The phenylene group may be an o-, m- or p-phenylene group, preferably a p-phenylene group.

[0065] Ar 2 may be an aryl group, preferably a phenyl group, or a naphthyl group, more preferably a phenyl group.

[0066] In the above group, R and R or Ar 1 and Ar 2 may be linked via a linker L. That is, R and R, or Ar 1 and Ar 2 may form a ring structure together with the linker L. For example, the above group may have the structure: [ka]

[0067] L is a single bond or C 1-6 -(C s H 2s ) x -(X 3 ) y -(C t H 2t ) z -, phenylene, or naphthylene.

[0068] -(C s H 2s )x -(X 3 ) y -(C t H 2t ) z -medium, X 3 is O, S, or NH; s is an integer from 1 to 6; t is an integer from 1 to 6; x, y, and z are each independently 0 or 1; However, at least one of x, y, and z is 1.

[0069] In one embodiment, L is a single bond.

[0070] In another embodiment, L is C 1-6 -(C s H 2s ) x -(X 3 ) y -(C t H 2t ) z -, a phenylene group, or a naphthylene group.

[0071] In one embodiment, -(C s H 2s ) x -(X 3 ) y -(C t H 2t ) z - is unsubstituted.

[0072] In another embodiment, -(C s H 2s ) x -(X 3 ) y -(C t H 2t ) z - is C 1-6 It is substituted with an alkyl group.

[0073] In one embodiment, y is 0.

[0074] In another embodiment, y is 1.

[0075] In one embodiment, L is C 1-10 An alkylene group, a phenylene group, or a naphthylene group, preferably C 1-10 It is an alkylene group.

[0076] Above C 1-10 The alkylene group is preferably 1-6 Alkylene group, more preferably C 1-3 It may be an alkylene group. The alkylene group may be a straight chain or a branched chain.

[0077] In a preferred embodiment, the radical generating group is the following group: [ka] [In formula: Y is C 1-6 an alkylene group or an optionally substituted phenylene group, R 23 are each independently 1-6 It is a hydrocarbon group or a phenyl group which may have a substituent.] It could be.

[0078] The substituents in the phenylene group and phenyl group are not particularly limited, but examples thereof include halogen atoms, C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 Alkynyl group, C 3-10 Cycloalkyl groups, C 3-10 Unsaturated cycloalkyl groups, 5-10 membered heterocyclyl groups, 5-10 membered unsaturated heterocyclyl groups, C 6-10 Aryl groups, 5-10 membered heteroaryl groups, nitro groups, and C 1-6 Examples of the alkoxy group include one or more groups selected from the group consisting of alkoxy groups.

[0079] The phenylene and phenyl groups are preferably nitro or C 1-6 The phenylene group and the phenyl group may be substituted with an alkoxy group, or an unsubstituted phenylene group and a phenyl group, and more preferably, the phenylene group and the phenyl group may be substituted with a nitro group, or an unsubstituted phenylene group and a phenyl group.

[0080] In the above formula, L 2 are each independently a group containing a divalent radical-forming group.

[0081] In a preferred embodiment, L 2 are each independently represented by the formula: -R 2 -R 4 -L R2 -R 4 -R 2 - [In formula: R 2 each independently represents an alkylene group, an oxygen atom, -COO-, -OCO-, or -CONR 11 - or -NR 11 CO-, R 11 is a hydrogen atom or C 1-6 is an alkyl group, R 4 are each independently a single bond or a divalent organic group, L R2 is a divalent radical-forming group. It may be a group represented by the formula:

[0082] R 2 each independently represents an alkylene group, an oxygen atom, -COO-, -OCO-, or -CONR 11 - or -NR 11 It is CO-.

[0083] In a preferred embodiment, R 2 is R 2a and R 2b That is, L 2 -R 2a -R 1 -R2b -It is.

[0084] R 2a is an alkylene group, an oxygen atom, -COO-, or -CONR 11 - and R 2b is an alkylene group, an oxygen atom, -OCO-, or -NR 11 CO-. Note that R 2a is R on the right 1 Binds to R 2b The left side is R 1 Bind to.

[0085] R 2a and R 2b are preferably groups corresponding to each other. 2a and R 2b The combination of is preferably an alkylene group and an alkylene group, an oxygen atom and an oxygen atom, -COO- and -OCO-, or -CONR 11 -and-NR 11 It is CO-.

[0086] In a preferred embodiment, R 2a -CONR 11 - and R 2b -NR 11 It is CO-.

[0087] R 2 The alkylene group in is preferably C 1-6 Alkylene group, more preferably C 1-3 It is an alkylene group. The alkylene group may be a straight chain or a branched chain.

[0088] R 11 is a hydrogen atom or C 1-6 It is an alkyl group, and preferably a hydrogen atom.

[0089] R 11 C in 1-6 The alkyl group is preferably C 1-3 It is preferably an alkyl group, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. 1-6The alkyl group may be straight or branched.

[0090] R 11 is preferably a methyl group or a hydrogen atom, and more preferably a hydrogen atom.

[0091] R 4 are each independently a single bond or a divalent organic group.

[0092] In one embodiment, R 4 are each independently a single bond or -(R 15 ) n1 -It is.

[0093] In the above formula, R 15 may each independently in each occurrence be 1-6 an alkylene group, a 3- to 8-membered cycloalkylene group, a 3- to 8-membered cycloalkenylene group, a 3- to 8-membered heterocycloalkylene group, a 3- to 8-membered heterocycloalkenylene group, an arylene group, or a heteroarylene group; and n1 is an integer of 1 to 6.

[0094] In a preferred embodiment, R 4 are each independently 1-6 Alkylene group or -R 17 -R 18 -R 19 -. Note that R 4 In R 17 R 6 Bind to.

[0095] In the above formula, R 17 is a single bond or C 1-6 is an alkylene group, R 18 is an arylene group, R 19 is a single bond or C 1-6 It is an alkylene group.

[0096] In one embodiment, R 17 is a single bond, and R 18is an arylene group, R 19 is C 1-6 It is an alkylene group.

[0097] R 4 C in 1-6 The alkylene group is preferably 1-3 Alkylene group, more preferably C 1-2 It is an alkylene group. 1-6 The alkylene group may be straight or branched.

[0098] R 4 C in 1-6 The alkylene group and the arylene group may be substituted. The substituent is not particularly limited, but examples thereof include a halogen atom, a C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 Alkynyl group, C 3-10 Cycloalkyl groups, C 3-10 Unsaturated cycloalkyl groups, 5-10 membered heterocyclyl groups, 5-10 membered unsaturated heterocyclyl groups, C 6-10 Examples of the alkyl group include one or more groups selected from an aryl group and a 5- to 10-membered heteroaryl group.

[0099] L R2 is a divalent radical-forming group

[0100] The divalent radical generating group is preferably the following group: [ka] [In formula: Y is a single bond or a divalent organic group; W 1 is an oxygen atom or NR 25 and W 2 OR 25 , or NR 25 2 and R25 is a hydrogen atom, an oxygen atom, or a hydrocarbon group, R 22 are each independently a hydrogen atom or a monovalent organic group, R 23 are each independently a hydrogen atom or a monovalent organic group, R 24 are each independently a hydrogen atom or a monovalent organic group, R 26 is a divalent organic group, Ar 1 are each independently an arylene group; However, R in the formula 23 and R 23 , R 25 and R 25 , or Ar 1 and Ar 1 is optionally linked via a linker L, L is a single bond or C 1-6 -(C s H 2s ) x -(X 3 ) y -(C t H 2t ) z -, phenylene, or naphthylene; X 3 is O, S, or NH; s is an integer from 1 to 6; t is an integer from 1 to 6; x, y, and z are each independently 0 or 1; However, at least one of x, y, and z is 1. It is.

[0101] In the above divalent radical generating group, Y and W 1 , W 2 , R 22 , R 23 , R 25 , Ar 1 , L, X 3, s, t, x, y, and z are the same as those in the monovalent radical generating group.

[0102] R 26 is a divalent organic group. 26 is preferably a hydrocarbon group, more preferably an alkylene group or an arylene group, still more preferably an alkylene group having 1 to 6 carbon atoms or a phenylene group, and particularly preferably a phenylene group.

[0103] In a preferred embodiment, the divalent radical generating group is the following group: [ka] [In formula: Ar 5 each independently represents a phenyl group which may have a substituent, Ar 6 each independently represents a phenylene group which may have a substituent, R 31 are each independently 1-6 is a hydrocarbon group, R 32 each independently represents a single bond or C 1-6 is an alkylene group. It is.

[0104] In one embodiment, Ar 5 is non-substitutive.

[0105] In another embodiment, Ar 5 has been substituted.

[0106] In one embodiment, Ar 6 is non-substitutive.

[0107] In another embodiment, Ar 6 has been substituted.

[0108] Ar 5 and Ar 6The substituent in is not particularly limited, but examples thereof include a halogen atom, a C 1-6 Alkyl group, C 2-6 Alkenyl group, C 2-6 Alkynyl group, C 3-10 Cycloalkyl groups, C 3-10 Unsaturated cycloalkyl groups, 5-10 membered heterocyclyl groups, 5-10 membered unsaturated heterocyclyl groups, C 6-10 Examples of the alkyl group include one or more groups selected from an aryl group and a 5- to 10-membered heteroaryl group.

[0109] R 31 are each independently preferably C 1-6 Alkyl groups, more preferably C 1-3 The alkyl group is preferably a methyl group, and the alkyl group may be a straight chain or a branched chain.

[0110] In one embodiment, R 32 is a single bond.

[0111] In another embodiment, R 32 is C 1-6 It is an alkylene group.

[0112] Above C 1-6 The alkylene groups are each independently preferably C 1-3 It may be an alkylene group. The alkylene group may be a straight chain or a branched chain.

[0113] In the above formula, R F1 are each independently a monovalent organic group containing a fluorine atom, and R F2 are each independently a divalent organic group containing a fluorine atom.

[0114] In one embodiment, F F1 and R F2In the above, the fluorine content is preferably 50% by mass or more, more preferably 55% by mass or more, even more preferably 57% by mass or more, and even more preferably 60% by mass or more. F1 and R F2 In the above, the fluorine content is preferably 76 mass % or less, more preferably 70 mass % or less, alternatively preferably 77 mass % or less, more preferably 73 mass % or less, and particularly preferably 68 mass % or less.

[0115] Conventional initiators have a low fluorine content and low durability against chemicals. In addition, there is a problem in increasing the amount of initiator to improve reactivity. The fluorine-containing compound of the present disclosure has a high fluorine content and high chemical resistance. In addition, the compounding amount can be increased to increase the curing efficiency and maintain chemical resistance.

[0116] In one embodiment, F F1 and R F2 In the above, the compatibility parameter (hereinafter also referred to as "SP value") is preferably 6.0 to 7.4, more preferably 6.2 to 7.2, and further preferably 6.4 to 7.0. The above SP value can be determined by Fedors' estimation method.

[0117] In one embodiment, R F1 are each independently R F3 -(Z 1 -R F4 ) k -It is.

[0118] In one embodiment, R F2 are each independently -R F4 -(Z 1 -R F4 ) k -It is.

[0119] R F3 are each independently Rf 1 -R F -O q - and R F4 are each independently -Rf 2 p -RF -O q -It is.

[0120] Rf 1 C may be substituted with one or more fluorine atoms 1-16 It is an alkyl group.

[0121] C which may be substituted with one or more fluorine atoms 1-16 "C" in alkyl group 1-16 The "alkyl group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C 1-6 Alkyl groups, especially C 1-3 is preferably a straight-chain C 1-6 Alkyl groups, especially C 1-3 It is an alkyl group.

[0122] Above Rf 1 is preferably C substituted by one or more fluorine atoms 1-16 is an alkyl group, more preferably CF 2 HC 1-15 A perfluoroalkylene group, more preferably C 1-16 It is a perfluoroalkyl group.

[0123] Above C 1-16 The perfluoroalkyl group may be linear or branched, and is preferably a linear or branched C 1-6 Perfluoroalkyl groups, especially C 1-3 A perfluoroalkyl group, more preferably a linear C 1-6 Perfluoroalkyl groups, especially C 1-3 Perfluoroalkyl groups, specifically -CF 3 , -CF 2 CF 3 , or -CF 2 CF 2 CF 3 It is.

[0124] Rf 2 C may be substituted with one or more fluorine atoms1-6 It is an alkylene group.

[0125] C which may be substituted with one or more fluorine atoms 1-6 "C" in the alkylene group 1-6 The "alkylene group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C 1-3 It is preferably a linear alkylene group. 1-3 It is an alkylene group.

[0126] Above Rf 2 is preferably C substituted by one or more fluorine atoms 1-6 is an alkylene group, more preferably C 1-6 A perfluoroalkylene group, more preferably C 1-3 It is a perfluoroalkylene group.

[0127] Above C 1-6 The perfluoroalkylene group may be linear or branched, and is preferably a linear or branched C 1-3 A perfluoroalkylene group, more preferably a linear C 1-3 Perfluoroalkyl groups, specifically -CF 2 -, -CF 2 CF 2 - or -CF 2 CF 2 CF 2 -It is.

[0128] p is 0 or 1. In one embodiment, p is 0. In another embodiment, p is 1.

[0129] Each q is independently 0 or 1. In one embodiment, q is 0. In another embodiment, q is 1.

[0130] R F are each independently a divalent fluoropolyether group.

[0131] R Fis preferably -(OC h1 R Fa 2h1 ) h3 -(OC h2 R Fa 2h2-2 ) h4 - [In formula: R Fa are each independently a hydrogen atom, a fluorine atom or a chlorine atom, h1 is an integer from 1 to 6, h2 is an integer from 4 to 8; h3 is an integer equal to or greater than 0, h4 is an integer equal to or greater than 0, However, the number of repeating units of h3 and h4 is 1 or more, preferably 2 or more, and more preferably 5 or more, and the order of the repeating units enclosed in parentheses with h3 and h4 is arbitrary in the formula. It may contain a group represented by:

[0132] In one embodiment, R F R can be linear or branched. F is preferably of the formula: -(OC 6 F 12 ) a -(OC 5 F 10 ) b -(OC 4 F 8 ) c -(OC 3 R Fa 6 ) d -(OC 2 F 4 ) e -(OCF 2 ) f - [In formula: R Fa are each independently a hydrogen atom, a fluorine atom or a chlorine atom, a, b, c, d, e, and f are each independently an integer of 0 to 200, and the sum of a, b, c, d, e, and f is 1 or more. The order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula. However, all R Fa is a hydrogen atom or a chlorine atom, at least one of a, b, c, e and f is 1 or greater.] It is a group represented by the following formula:

[0133] R Fa is preferably a hydrogen atom or a fluorine atom, more preferably a fluorine atom. However, all R Fa is a hydrogen atom or a chlorine atom, at least one of a, b, c, e and f is 1 or greater.

[0134] Preferably, a, b, c, d, e and f may each independently be an integer of 0 to 100.

[0135] The sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more. The sum of a, b, c, d, e and f is preferably 200 or less, more preferably 100 or less, and even more preferably 60 or less, and may be, for example, 50 or less or 30 or less.

[0136] These repeating units may be linear or branched. For example, -(OC 6 F 12 )- is -(OCF 2 CF 2 CF 2 CF 2 CF 2 CF 2 )-, -(OCF(CF 3 )CF 2 CF 2 CF 2 CF 2 )-, -(OCF 2 CF(CF 3 )CF 2 CF 2 CF 2 )-, -(OCF2 CF 2 CF(CF). 3 )CF 2 CF 2 )-、-(OCF 2 CF 2 CF 2 CF(CF). 3 )CF 2 )-、-(OCF 2 CF 2 CF 2 CF 2 CF(CF). 3 ))-without-(OC 5 F 10 )-は、-(OCF 2 CF 2 CF 2 CF 2 CF 2 )-、-(OCF(CF). 3 )CF 2 CF 2 CF 2 )-、-(OCF 2 CF(CF). 3 )CF 2 CF 2 )-、-(OCF 2 CF 2 CF(CF). 3 )CF 2 )-、-(OCF 2 CF 2 CF 2 CF(CF). 3 ))-without-(OC 4 F 8 )-は、-(OCF 2 CF 2 CF 2 CF 2 )-、-(OCF(CF). 3 )CF 2 CF 2 )-、-(OCF 2 CF(CF). 3 )CF 2 )-、-(OCF 2 CF 2 CF(CF). 3 ))-、-(OC(CF). 3 ) 2 CF 2 )-、-(OCF 2 C(CF).3 ) 2 )-, -(OCF(CF 3 )CF(CF 3 ))-, -(OCF(C 2 F 5 )CF 2 )-and-(OCF 2 CF(C 2 F 5 ))-. -(OC 3 F 6 )-(i.e., in the above formula, R Fa is a fluorine atom) is -(OCF 2 CF 2 CF 2 )-, -(OCF(CF 3 )CF 2 )-and-(OCF 2 CF(CF 3 ))-. -(OC 2 F 4 )- is -(OCF 2 CF 2 )-and-(OCF(CF 3 ))-.

[0137] In one embodiment, the repeat unit is linear.

[0138] In one embodiment, the repeat unit is branched.

[0139] In one embodiment, R F may include a ring structure.

[0140] The ring structure may be a three-, four-, five-, or six-membered ring as shown below. [ka] [In the formula, * indicates the bond position.]

[0141] The ring structure may preferably be a four-, five-, or six-membered ring, more preferably a four-, or six-membered ring.

[0142] The repeating unit having a ring structure may preferably be the following unit. [ka] [In the formula, * indicates the bond position.]

[0143] In one embodiment, R F are each independently a group represented by any one of the following formulas (f1) to (f6). -(OC 3 F 6 ) d -(OC 2 F 4 ) e - (f1) [In the formula, d is an integer of 1 to 200, and e is 0 or 1.]; -(OC 4 F 8 ) c -(OC 3 F 6 ) d -(OC 2 F 4 ) e -(OCF 2 ) f - (f2) [In the formula, c and d each independently represent an integer of 0 or more and 30 or less, and e and f each independently represent an integer of 1 or more and 200 or less, The sum of c, d, e, and f is 2 or more, The order of occurrence of each repeat unit enclosed in parentheses with the subscript c, d, e, or f is arbitrary in the formula. -(R 6 -R 7 ) g - (f3) [In the formula, R 6 is OCF 2 Or O.C. 2 F 4 and R 7 is O.C. 2 F 4 , O.C. 3 F 6 , O.C. 4 F 8 , O.C.5 F 10 and O.C. 6 F 12 or a combination of two or three groups independently selected from these groups; g is an integer from 2 to 100; -(R 6 -R 7 ) g -R r -(R 7’ -R 6’ ) g’ - (f4) [In the formula, R 6 is OCF 2 Or O.C. 2 F 4 and R 7 is O.C. 2 F 4 , O.C. 3 F 6 , O.C. 4 F 8 , O.C. 5 F 10 and O.C. 6 F 12 or a combination of two or three groups independently selected from these groups; R 6’ is OCF 2 Or O.C. 2 F 4 and R 7’ is O.C. 2 F 4 , O.C. 3 F 6 , O.C. 4 F 8 , O.C. 5 F 10 and O.C. 6 F 12 or a combination of two or three groups independently selected from these groups; g is an integer from 2 to 100; g' is an integer from 2 to 100, R r teeth, [ka] (In the formula, * indicates the bond position.) .]; -(OC 6 F 12 ) a -(OC 5 F 10 ) b -(OC 4 F 8 ) c -(OC 3 F 6 ) d -(OC 2 F 4 ) e -(OCF 2 ) f - (f5) [In the formula, e is an integer of 1 or more and 200 or less, a, b, c, d, and f are each independently an integer of 0 or more and 200 or less, and the order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula.] -(OC 6 F 12 ) a -(OC 5 F 10 ) b -(OC 4 F 8 ) c -(OC 3 F 6 ) d -(OC 2 F 4 ) e -(OCF 2 ) f - (f6) [In the formula, f is an integer of 1 or more and 200 or less, a, b, c, d, and e are each independently an integer of 0 or more and 200 or less, and the order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula.]

[0144] In the above formula (f1), d is preferably an integer of 5 to 200, more preferably 10 to 100, further preferably 15 to 50, for example, an integer of 25 to 35. In one embodiment, e is 1. In another embodiment, e is 0. In the above formula (f1), -(OC 3 F 6 ) d - is preferably -(OCF 2 CF 2 CF 2 ) d -or-(OCF(CF 3 )CF 2 ) d -, and more preferably -(OCF 2 CF 2 CF 2 ) d - is a group represented by the formula:

[0145] In the above formula (f2), e and f are each independently an integer of preferably 5 to 200, more preferably 10 to 200. The sum of c, d, e and f is preferably 5 or more, more preferably 10 or more, and may be, for example, 15 or more or 20 or more. In one embodiment, the above formula (f2) is preferably -(OCF 2 CF 2 CF 2 CF 2 ) c -(OCF 2 CF 2 CF 2 ) d -(OCF 2 CF 2 ) e -(OCF 2 ) f In another embodiment, formula (f2) is a group represented by -(OC 2 F 4 ) e -(OCF 2 ) f - may be a group represented by the formula:

[0146] In the above formula (f3), R 6 Preferably, OC 2 F 4In the above (f3), R 7 Preferably, OC 2 F 4 , O.C. 3 F 6 and O.C. 4 F 8 or a combination of two or three groups independently selected from these groups, more preferably OC 3 F 6 and O.C. 4 F 8 is a group selected from the group consisting of OC 2 F 4 , O.C. 3 F 6 and O.C. 4 F 8 Examples of the combination of two or three groups independently selected from the group consisting of, but not limited to, -OC 2 F 4 O.C. 3 F 6 -, -OC 2 F 4 O.C. 4 F 8 -, -OC 3 F 6 O.C. 2 F 4 -, -OC 3 F 6 O.C. 3 F 6 -, -OC 3 F 6 O.C. 4 F 8 -, -OC 4 F 8 O.C. 4 F 8 -, -OC 4 F 8 O.C. 3 F 6 -, -OC 4 F 8 O.C. 2 F 4 -, -OC 2 F 4 O.C. 2 F 4 O.C. 3 F 6 -, -OC 2 F 4 O.C.2 F 4 O.C. 4 F 8 -, -OC 2 F 4 O.C. 3 F 6 O.C. 2 F 4 -, -OC 2 F 4 O.C. 3 F 6 O.C. 3 F 6 -, -OC 2 F 4 O.C. 4 F 8 O.C. 2 F 4 -, -OC 3 F 6 O.C. 2 F 4 O.C. 2 F 4 -, -OC 3 F 6 O.C. 2 F 4 O.C. 3 F 6 -, -OC 3 F 6 O.C. 3 F 6 O.C. 2 F 4 - and -OC 4 F 8 O.C. 2 F 4 O.C. 2 F 4 In the above formula (f3), g is preferably an integer of 3 or more, more preferably an integer of 5 or more. The above g is preferably an integer of 50 or less. In the above formula (f3), OC 2 F 4 , O.C. 3 F 6 , O.C. 4 F 8 , O.C. 5 F 10 and O.C. 6 F 12 may be either linear or branched, and is preferably linear. In this embodiment, the above formula (f3) is preferably -(OC 2 F4 -OC 3 F 6 ) g -or- (OC 2 F 4 -OC 4 F 8 ) g -It is.

[0147] In the above formula (f4), R 6 , R 7 and g have the same meanings as those described in the above formula (f3) and have the same embodiments. 6’ , R 7’ and g' are R 6 , R 7 and g have the same meaning and behavior. r is preferably [ka] [In the formula, * indicates the bond position.] and more preferably [ka] [In the formula, * indicates the bond position.] It is.

[0148] In the above formula (f5), e is preferably an integer of 1 or more and 100 or less, more preferably an integer of 5 or more and 100 or less. The sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, for example, 10 or more and 100 or less.

[0149] In the above formula (f6), f is preferably an integer of 1 or more and 100 or less, more preferably an integer of 5 or more and 100 or less. The sum of a, b, c, d, e and f is preferably 5 or more, more preferably 10 or more, for example, 10 or more and 100 or less.

[0150] In one embodiment, the R F is a group represented by the above formula (f1).

[0151] In one embodiment, the R F is a group represented by the above formula (f2).

[0152] In one embodiment, the R F is a group represented by the above formula (f3).

[0153] In one embodiment, the R F is a group represented by the above formula (f4).

[0154] In one embodiment, the R F is a group represented by the above formula (f5).

[0155] In one embodiment, the R F is a group represented by the above formula (f6).

[0156] In one embodiment, R F1 and R F2 The fluorine content of each of R is independently 50% by mass or more, preferably 55% by mass or more, more preferably 57% by mass or more, and further preferably 60% by mass or more. F1 and R F2 The fluorine content of each of R is independently 76% by mass or less, preferably 70% by mass or less, more preferably 77% by mass or less, even more preferably 73% by mass or less, and even more preferably 68% by mass or less. F1 and R F2 By setting the fluorine content within the above range, the chemical resistance of the obtained cured film is improved.

[0157] In one embodiment, R F1 and R F2 The calculated compatibility parameters (SP values) of R are each independently 6.0 to 7.4, preferably 6.2 to 7.2, and more preferably 6.4 to 7.0. F1 and R F2 By setting the SP value within the above range, the chemical resistance of the obtained cured film is improved.

[0158] Z 1each independently represents a single bond or a divalent organic group.

[0159] In one embodiment, Z 1 is a single bond.

[0160] In another embodiment, Z 1 are each independently a divalent organic group.

[0161] Z 1 is preferably a group containing a divalent radical-forming group.

[0162] In a preferred embodiment, Z 1 is expressed by the following formula: -R 2 -R 4 -L R2 -R 4 -R 2 - [In the formula, R 2 , R 4 , and L R2 is the above L 2 ] It may be a group represented by the formula:

[0163] Each k is independently an integer of 0 to 20, preferably an integer of 0 to 10, more preferably an integer of 0 to 8, and further preferably an integer of 0 to 5.

[0164] In one embodiment, k is 0.

[0165] In another embodiment, k is 1.

[0166] In another embodiment, k is 2 or greater.

[0167] The number average molecular weight of the fluorine-containing compound represented by formula (S1), (S2) or (S3) of the present disclosure is not particularly limited, but may be 300 or more, preferably 500 or more, more preferably 1,000 or more, and even more preferably 2,000 or more. The number average molecular weight of the fluorine-containing compound represented by formula (S1), (S2) or (S3) of the present disclosure is not particularly limited, but may be 100,000 or less, preferably 30,000 or less, more preferably 20,000 or less, and even more preferably 10,000 or less. The number average molecular weight of the fluorine-containing compound represented by formula (S1), (S2) or (S3) of the present disclosure is not particularly limited, but may be, for example, 300 to 100,000, preferably 500 to 30,000, more preferably 1,000 to 20,000, and even more preferably 2,000 to 10,000. The number average molecular weight can be measured by GPC (gel permeation chromatography).

[0168] The molecular weight distribution (weight average molecular weight / number average molecular weight) of the fluorine-containing compound represented by formula (S1), (S2) or (S3) of the present disclosure is preferably 1.0 or more, but may be 1.1 or more or 1.2 or more. The molecular weight distribution of the fluorine-containing compound represented by formula (S1), (S2) or (S3) is preferably 4.0 or less, more preferably 3.0 or less, and even more preferably 2.0 or less. The molecular weight distribution of the fluoropolyether group-containing chain compound represented by formula (S1), (S2) or (S3) is preferably 1.0 to 4.0, more preferably 1.0 to 3.0, and even more preferably 1.0 to 2.0. Here, the molecular weight distribution can be measured by GPC (gel permeation chromatography).

[0169] The fluorine content of the fluorine-containing compound represented by formula (S1), (S2) or (S3) of the present disclosure may be preferably 50% by mass or more, more preferably 55% by mass or more, and even more preferably 60% by mass or more. The fluorine content of the fluorine-containing compound may be preferably 80% by mass or less, more preferably 75% by mass or less, and even more preferably 70% by mass or less.

[0170] The fluorine content of the above fluorine-containing compound is measured by measuring the molecular weight by GPC and 19 The average fluorine content can be determined from the monomer unit ratio by FNMR.

[0171] The fluorine content / oxygen content ratio of the fluorine-containing compound represented by formula (S1), (S2) or (S3) of the present disclosure may be preferably 1.0 or more, more preferably 1.5 or more, even more preferably 2.0 or more, and even more preferably 2.5 or more. The fluorine content / oxygen content ratio of the fluorine-containing compound is preferably 10.0 or less, more preferably 8.0 or less, even more preferably 7.0 or less, and even more preferably 5.0 or less. The fluorine content / oxygen content ratio of the fluorine-containing compound may be preferably 1.5 to 8.0, more preferably 2.0 to 7.0, and even more preferably 2.5 to 5.0. Here, the fluorine content / oxygen content ratio is the mass ratio of the fluorine content to the oxygen content.

[0172] The fluorine content / oxygen content ratio of the fluorine-containing compound can be determined by various nuclear magnetic resonance measurements and gel permeation chromatography. That is, the average molecular weight of the molecule is calculated from the number average molecular weight of the polymer portion calculated by gel permeation chromatography and the structure of the radical generating portion confirmed by nuclear magnetic resonance, and the ratio of the weight determined from the number of fluorine atoms in the structure to the weight derived from the number of oxygen atoms can be calculated.

[0173] The wavelength of light irradiated to generate radicals from the fluorine-containing compound represented by formula (S1), (S2) or (S3) of the present disclosure is preferably 500 nm or less, more preferably 400 nm or less, for example, 275 nm or less, or 255 nm or less. The lower limit is preferably 200 nm or more, more preferably 210 nm or more.

[0174] The lowest bond dissociation energy among the bond dissociation energies for each bond in the fluorine-containing compound represented by formula (S1), (S2) or (S3) of the present disclosure may be preferably 300 kJ / mol or less, more preferably 250 kJ / mol or less, more preferably 200 kJ / mol or less, and even more preferably 185 kJ / mol or less. The lower limit of the lowest bond dissociation energy is not particularly limited, but if the value is too small, it is unstable as a polymerization initiator. A normal carbon-carbon bond and a carbon-oxygen bond have a bond dissociation energy of more than 300 kJ / mol. In addition, a carbon-fluorine bond has a bond dissociation energy of 400 kJ / mol or more. Therefore, the fluorine-containing compound of the present disclosure can cleave such a site with high efficiency by having a bond with a bond dissociation energy of 300 kJ / mol or less.

[0175] Here, bond dissociation energy is the amount of energy change when a covalent bond in an AB bond is homolytically cleaved to produce A· and B·.

[0176] The compound of the present disclosure may have a structure capable of generating radicals by dissociation of carbon-carbon bonds and carbon-oxygen bonds. Usually, irradiation with light for dissociating such bonds may simultaneously cause cleavage at various sites of the molecule, and there is a concern that unintended low molecular weight or decomposition may result in undesired by-products that lead to the fragility of the cured composition. On the other hand, the compound of the present disclosure has a bond with a bond dissociation energy of 300 kJ / mol or less, and therefore cleavage can occur at this site. In other words, radicals can be generated with high efficiency at the targeted site.

[0177] The bond dissociation energy is calculated by Gaussian16, a quantum chemical calculation program manufactured by Gaussian, using B3LYP as the density functional and 6-31+g(d) as the basis function. The bond dissociation energy is calculated as follows. First, the radical generating group L1 or L2 in the fluorine-containing compound represented by (S1), (S2) or (S3) is taken out, and R F1 or R F2The bond with is terminated with a hydrogen atom to create a radical generating group model molecule, and the energy of the optimized structure is calculated and the value is E(A+B). Next, two radical model molecules are created by cutting the radical generating group model molecule at the bond for which the bond dissociation energy is to be calculated, and the energy of the optimized structure is calculated. These values ​​are E(A) and E(B), respectively. The bond dissociation energy ΔE is defined as ΔE=E(A)+E(B)-E(A+B). The charge and spin multiplicity in calculations using Gaussian16 are set according to the following rules. The charge is set to 0 in calculations for all model molecules. The spin multiplicity is set to 1 in calculations for radical generating group model molecules. The spin multiplicity is set to 2 in calculations for radical model molecules generated by cutting single bonds. The spin multiplicity is set to 1 in calculations for radical model molecules generated by cutting double bonds. The spin multiplicity is set to 2 in calculations for radical model molecules generated by cutting triple bonds.

[0178] In one embodiment, the fluorine-containing compound of the present disclosure is a fluorine-containing compound represented by formula (S1). The fluorine-containing compound represented by formula (S1) can generate a low molecular weight radical and a high molecular weight radical upon radical generation.

[0179] In another embodiment, the fluorine-containing compound of the present disclosure is a fluorine-containing compound represented by formula (S2) or (S3). The fluorine-containing compound represented by formula (S2) or (S3) can generate a polymer radical when generating a radical. By using the fluorine-containing compound represented by formula (S2) or (S3), the curing efficiency is improved and the chemical resistance of the obtained film is improved.

[0180] The fluorine-containing compound of the present disclosure can be synthesized, for example, from a perfluoropolyether group-containing compound having a functional group at its terminal.

[0181] In one embodiment, the fluorine-containing compound of the present disclosure has the following groups at both ends: TIFF2025079212000019.tif4034 (in the formula, R 23are each independently a hydrogen atom or a monovalent organic group, or two R 23 may be bonded to form a ring, Y is a single bond or a divalent organic group; However, R 23 At least one of Y does not contain a phenyl group. The polymerizable compound can be obtained by polymerizing a compound having a group containing a group represented by the following formula:

[0182] Therefore, the present disclosure provides a compound represented by the formula (S3a): AR F2 -A [In formula: R F2 is a divalent organic group containing a fluorine atom, Each A is independently represented by the following formula: [ka] (In the formula, R 23 are each independently a hydrogen atom or a monovalent organic group, or two R 23 may be bonded to form a ring, Y is a single bond or a divalent organic group; However, R 23 At least one of Y does not contain a phenyl group. It is a group containing a group represented by the following formula: The present invention provides a compound represented by the formula:

[0183] R F2 is the R described in the above formula (S1) etc. F2 This has the same meaning as:

[0184] Each A preferably independently represents the formula: -R 7 -R 8 -R 9 [In formula: R 7 is an alkylene group, an oxygen atom, -COO-, or -CONR11 - and R 11 is a hydrogen atom or C 1-6 is an alkyl group, R 8 is a single bond or a divalent organic group, R 9 is expressed by the following formula: [ka] (In the formula, R 23 are each independently a hydrogen atom or a monovalent organic group, or two R 23 may be bonded to form a ring, Y is a single bond or a divalent organic group; However, R 23 At least one of Y does not contain a phenyl group. is a group represented by the following formula: It may be a group represented by the formula:

[0185] In one embodiment, R 8 is a single bond.

[0186] In another embodiment, R 8 is a divalent organic group.

[0187] The divalent organic group is preferably represented by the following formula: -(R 51 ) p5 -(R 52 ) q5 - [In formula: R 51 is a single bond, C 1-20 an alkylene group, or an o-, m- or p-phenylene group; R 52 each independently represents -O-, -S-, o-, m- or p-phenylene group, -COO-, -OCO-, -CONR 54 -, -NR 54 CO-, -O-CONR 54 -, -NR 54 CO-O- and -NR54 - is a group selected from the group consisting of R 54 are each independently a hydrogen atom, a phenyl group, or C 1-6 is an alkyl group, p5 is an integer from 0 to 6; q5 is an integer from 0 to 6, wherein at least one of p5 and q5 is 1 or more, and the order of the repeating units enclosed in parentheses with p5 or q5 is arbitrary. It is a divalent organic group represented by the formula:

[0188] In another embodiment, the fluorine-containing compound of the present disclosure can be obtained by introducing a radical-generating group into a compound having functional groups at both ends, for example, a carboxylic acid, a carboxylic acid ester, an alcohol, or an acid halide, for example, an acid chloride, containing a perfluoropolyether group.

[0189] For example, the expression: R 40 CO-R F2 -COR 40 [In formula: R F2 has the same meaning as above, R 40 is a hydrolyzable group, preferably a halogen (preferably chlorine), OR 42 , or OCOR 43 , more preferably halogen; R 42 is C 1-6 is an alkyl group, R 43 is C 1-6 is an alkyl group. and a perfluoropolyether group-containing acid halide represented by the formula: R 41 O-PR 24 2 [In formula: R 41 is C 1-6 an alkyl group, preferably a methyl group; R24 has the same meaning as above.] With a phosphine compound represented by formula (S1), a compound represented by formula (S2) can be obtained.

[0190] The present disclosure provides a curable composition comprising the fluorine-containing compound of the present disclosure.

[0191] The curable composition of the present disclosure comprises: (i) a fluorine-containing compound represented by the above formula (S1), (S2), or (S3), (ii) Fluorine-containing polymerizable monomer Contains:

[0192] Examples of the fluorine-containing polymerizable monomer include a fluorine-containing vinyl monomer, a fluorine-containing acrylic monomer, a fluorine-containing styrene monomer, a hydrogen-containing fluoroolefin, a fluorine-containing norbornene, etc. The fluorine-containing polymerizable monomer may be preferably a fluorine-containing vinyl monomer or a fluorine-containing acrylic monomer, more preferably a fluorine-containing acrylic monomer.

[0193] The above-mentioned fluorine-containing polymerizable monomer preferably has a fluoropolyether group, and more preferably has a fluoropolyether group and a (meth)acrylate group.

[0194] In one embodiment, the fluorine-containing polymerizable monomer is represented by the following formula (M): (CH 2 =CR 71 -O-) m1 -X 7 -R F72 -X 7 -(OCO-CR 71 =CH 2 ) m1 [In formula: R F72 is -Rf 2 p -R F -O q - and Rf 2C may be substituted with one or more fluorine atoms 1-6 is an alkylene group, R F are each independently a divalent fluoropolyether group, p is 0 or 1; Each q is independently 0 or 1; R 71 are each independently a hydrogen atom or C 1-6 is an alkyl group, X 7 are each independently a divalent to pentavalent organic group, Each m1 is independently an integer of 1 to 4. The compound may be represented by the formula:

[0195] Above Rf 2 , R F , p, and q are defined as in formulae (S1), (S2), and (S3) above.

[0196] In one embodiment, R 71 is a hydrogen atom.

[0197] In another embodiment, R 71 are each independently 1-6 It is an alkyl group.

[0198] Above C 1-6 The alkyl group is preferably C 1-3 It is preferably an alkyl group, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. 1-6 The alkyl group may be straight or branched.

[0199] X 7 are each independently a divalent to pentavalent organic group.

[0200] In one embodiment, X 7 is a divalent organic group.

[0201] In another embodiment, X7 is a trivalent to pentavalent organic group.

[0202] In a preferred embodiment, X 7 are each independently a single bond or a group represented by the following formula: -(R 55 ) p7 -(R 56 ) q7 - [In formula: R 55 is a single bond, C 1-20 an alkylene group, or an o-, m- or p-phenylene group; R 56 each independently represents -O-, -S-, o-, m- or p-phenylene group, -COO-, -OCO-, -CONR 57 -, -NR 57 CO-, -O-CONR 57 -, -NR 57 CO-O- and -NR 57 - is a group selected from the group consisting of R 57 are each independently a hydrogen atom, a phenyl group, or C 1-6 is an alkyl group, p7 is an integer from 0 to 6, q7 is an integer from 0 to 6, Here, at least one of p7 and q7 is 1 or more, and the order of the repeating units enclosed in parentheses with p7 or q7 is arbitrary. It is possible for X to be a divalent organic group represented by the following formula: 7 In the case of two or more homogeneous R 56 are not consecutively combined.

[0203] In one embodiment, X 7 is a single bond.

[0204] In another embodiment, X 7 is -(R 55 ) p7 -(R 56 ) q7 - is a group represented by the formula:

[0205] R 55 is preferably C 1-20 An alkylene group, or an o-, m- or p-phenylene group, more preferably C 1-20 It may be an alkylene group. 1-20 The alkylene group is preferably 1-10 Alkylene group, more preferably C 1-6 It may be an alkylene group. Such an alkylene group may be a straight chain or a branched chain.

[0206] R 56 is preferably -O-, -COO-, -OCO-, -CONR 57 -, -NR 57 CO-, -O-CONR 57 -, -NR 57 CO-O- or -NR 57 -, more preferably -COO-, -OCO-, -CONR 57 -, -NR 57 CO-, -O-CONR 57 - or -NR 57 CO-O-, more preferably -CONR 57 --It could be.

[0207] R 57 is preferably a hydrogen atom or C 1-6 It is an alkyl group.

[0208] In one embodiment, R 57 is a hydrogen atom.

[0209] In another embodiment, R 57 is C 1-6 Alkyl groups, preferably C 1-3 It is preferably an alkyl group, more preferably a methyl group. The alkyl group may be linear or branched.

[0210] In one embodiment, p7 is 0.

[0211] In another embodiment, p7 is an integer from 1 to 6, such as an integer from 1 to 3, or 1.

[0212] In one embodiment, q7 is 0.

[0213] In another embodiment, q7 is an integer from 1 to 6, such as an integer from 1 to 3, or 1.

[0214] In the curable composition of the present disclosure, the SP value of the fluorine-containing compound and the fluorine-containing polymerizable monomer of the present disclosure may be preferably 7.4 or less, more preferably 7.0 or less. The SP value of the fluorine-containing compound and the fluorine-containing polymerizable monomer of the present disclosure may be preferably 6.0 or more, more preferably 6.2 or more. The SP value of the fluorine-containing compound and the fluorine-containing polymerizable monomer of the present disclosure may be, for example, 6.0 to 7.4, or 6.2 to 7.0.

[0215] The above SP value can be calculated by Fedors' estimation method.

[0216] In the curable composition of the present disclosure, the fluorine-containing compound of the present disclosure may be preferably 0.1 parts by mass or more, more preferably 0.2 parts by mass or more, even more preferably 0.3 parts by mass or more, even more preferably 0.5 parts by mass or more, for example 1.0 parts by mass or more, relative to 100 parts by mass of the fluorine-containing polymerizable monomer. The fluorine-containing compound of the present disclosure may be preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, for example 15 parts by mass or less, or 10 parts by mass or less, relative to 100 parts by mass of the fluorine-containing polymerizable monomer. The fluorine-containing compound of the present disclosure is preferably contained in an amount of 0.1 to 50 parts by mass, more preferably 0.2 to 30 parts by mass, even more preferably 0.3 to 10.0 parts by mass, for example 0.5 to 10 parts by mass, 0.5 to 5.0 parts by mass, or 0.5 to 1.0 parts by mass, relative to 100 parts by mass of the fluorine-containing polymerizable monomer. Since the fluorine-containing compound of the present disclosure exhibits very high curability as a polymerization initiator, it can cure the fluorine-containing monomer even in a small amount.

[0217] The curable compositions of the present disclosure may include a solvent.

[0218] In a preferred embodiment, the solvent content of the curable composition of the present disclosure may be 20% by weight or less, preferably 15% by weight or less, more preferably 10% by weight or less, even more preferably 5% by weight or less, even more preferably 3% by weight or less, and particularly preferably 1% by weight or less. In a particularly preferred embodiment, the curable composition of the present disclosure is substantially free of solvent.

[0219] The composition described in Patent Document 1 is a diluted solution containing a large amount of solvent. This diluted solution is made into a thin film by spin coating, and cured by light irradiation to form a surface treatment film. The curable composition containing the compound of the present disclosure does not have sufficient curability at the same concentration as that of Patent Document 1. However, by setting the solvent content within the above range, particularly by using no solvent, good compatibility and curability can be achieved.

[0220] The solvent may be, for example, aliphatic hydrocarbons, aromatic hydrocarbons, esters, ketones, glycol ethers, alcohols, glycols, cyclic ethers, amides, ether alcohols, perfluoroaliphatic hydrocarbons having 5 to 12 carbon atoms, polyfluoroaromatic hydrocarbons, polyfluoroaliphatic hydrocarbons, hydrofluorocarbons, hydrochlorofluorocarbons, or hydrofluoroethers. The solvent may be a mixed solvent of two or more of these.

[0221] Examples of the aliphatic hydrocarbons include hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, mineral spirits, and the like.

[0222] Examples of the aromatic hydrocarbons include benzene, toluene, xylene, naphthalene, and solvent naphtha.

[0223] Examples of the esters include methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, isopropyl acetate, isobutyl acetate, cellosolve acetate, propylene glycol methyl ether acetate, carbitol acetate, diethyl oxalate, ethyl pyruvate, ethyl 2-hydroxybutyrate, ethyl acetoacetate, amyl acetate, methyl lactate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 2-hydroxyisobutyrate, and ethyl 2-hydroxyisobutyrate.

[0224] Examples of the ketones include acetone, methyl ethyl ketone, methyl isobutyl ketone, 2-hexanone, cyclohexanone, methylamino ketone, and 2-heptanone.

[0225] Examples of the glycol ethers include ethyl cellosolve, methyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, dipropylene glycol dimethyl ether, and diethylene glycol monoethyl ether acetate.

[0226] Examples of the alcohols include methanol, ethanol, isopropyl alcohol, n-butanol, isobutanol, tert-butanol, sec-butanol, 3-pentanol, octyl alcohol, 3-methyl-3-methoxybutanol, tert-amyl alcohol, etc. The alcohols are preferably methanol, ethanol, or isopropyl alcohol.

[0227] Examples of the glycols include ethylene glycol and propylene glycol.

[0228] Examples of the cyclic ethers include tetrahydrofuran, tetrahydropyran, and dioxane.

[0229] Examples of the amides include N,N-dimethylformamide and N,N-dimethylacetamide.

[0230] Examples of the ether alcohols include methyl cellosolve, cellosolve, isopropyl cellosolve, butyl cellosolve, and diethylene glycol monomethyl ether.

[0231] Examples of the perfluoroaliphatic hydrocarbon having 5 to 12 carbon atoms include perfluorohexane, perfluoromethylcyclohexane, and perfluoro-1,3-dimethylcyclohexane.

[0232] The polyfluoroaromatic hydrocarbons include bis(trifluoromethyl)benzene and the like.

[0233] The polyfluoroaliphatic hydrocarbons include C 6 F 13 CH 2 CH 3 (for example, Asahiklin (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (for example, Zeorora (registered trademark) H manufactured by Zeon Corporation), and the like.

[0234] Hydrofluorocarbons (HFCs) include 1,1,1,3,3-pentafluorobutane (HFC-365mfc) and the like.

[0235] Examples of hydrochlorofluorocarbons (HCFCs) include 1,1,2-trichloro-1,2,2-trifluoroethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, and 1,1-dichloro-1,2,2,3,3-pentafluoropropane (HCFC225) (for example, Asahiklin (registered trademark) AK225).

[0236] The above hydrofluoroethers (HFEs) include perfluoropropyl methyl ether (C 3 F 7 OCH 3 ) (e.g., Novec (trademark) 7000 manufactured by Sumitomo 3M Co., Ltd.), perfluorobutyl methyl ether (C 4 F 9 OCH 3 ) (e.g., Novec (trademark) 7100 manufactured by Sumitomo 3M Co., Ltd.), perfluorobutyl ethyl ether (C 4 F 9 O.C. 2 H 5 ) (e.g., Novec (trademark) 7200 manufactured by Sumitomo 3M Limited), perfluorohexyl methyl ether (C 2 F 5 CF(OCH 3 ) C 3 F 7 ) (e.g., Novec™ 7300 manufactured by Sumitomo 3M Limited) (wherein the perfluoroalkyl group and the alkyl group may be linear or branched), CF 3 CH 2 OCF 2 CHF 2 (For example, Asahiklin (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.)

[0237] The curable composition of the present disclosure may contain other components, such as antioxidants, thickeners, leveling agents, defoamers, antistatic agents, antifogging agents, UV absorbers, pigments, dyes, inorganic fine particles such as silica, fillers such as aluminum paste, talc, glass frit, and metal powder, and polymerization inhibitors such as butylated hydroxytoluene (BHT) and phenothiazine (PTZ).

[0238] The present disclosure provides a cured product obtained by curing the curable composition of the present disclosure.

[0239] The cured product of the present disclosure is mixing a fluorine-containing compound with a fluorine-containing polymerizable monomer to obtain a mixture, i.e., a curable composition; A cured product is obtained by irradiating the mixture with light having a wavelength of 200 to 500 nm. The method can be obtained by a method comprising the steps of:

[0240] In a preferred embodiment, the mixture obtained by mixing the above-mentioned fluorine-containing compound and the fluorine-containing polymerizable monomer has a solvent content of 50% or less by weight, preferably 40% or less, more preferably 35% or less, for example 20% or less, 15% or less, 10% or less, 5% or less, 3% or less, or 1% or less. The mixture may be solvent-free.

[0241] The curable composition can be cured at room temperature.

[0242] The curable composition of the present disclosure can be used, without particular limitation, in the manufacture of rubber materials such as sealants, adhesives, coating agents, potting agents, O-rings, packings, gaskets, diaphragms, valves, and seals. EXAMPLES

[0243] The compound of the present disclosure will be described in more detail through the following examples, but the present disclosure is not limited to these examples.In this embodiment, the order of the repeating units constituting perfluoropolyether is arbitrary.In addition, the chemical formulas shown below all show average composition.

[0244] Synthesis Example 1 As the PFPE compounds, the following compounds were prepared. H 3 COOC-CF 2 -(OC 2 F 4 ) m -(OCF 2 ) n -COOCH 3 (m≒19, n≒28) The above PFPE compound (4.53 g, 1.05 mmol) was dissolved in 1,3-bistrifluoromethylbenzene (25 mL), and the solution was added with 4-RC. 6 H 4 CH 2 NH 2 (In the formula, R is 4,5-diphenyl-1H-imidazol-2-yl.) (1.14 g) in THF solution (40 mL) was added and stirred at room temperature under nitrogen for 20 hours. The solvent was then distilled off, and the remaining solid was washed with methanol and dried to obtain the target compound as a white solid (5.14 g, 94%).

[0245] 1 H NMR (500MHz, Novec® 7200 / MeOH (10 / 1, v / v)) δ 10.27(bs, 2H), 8.47(bs, 4H), 8.02(bs, 8H), 7.91(bs, 4H), 7.81-7.77(m, 12H). 19 F NMR (470 MHz, (1,3-bistrifluoromethylbenzene / MeOH (10 / 1, v / v)) δ -54.23, -55.83, -57.55, -80.51, -82.24, -91.16, -92.82, -128.10, -131.74. Fluorine content: 52.2%, Fluorine content / oxygen content ratio: 3.2

[0246] Example 1 To a solution (66 mL) of the compound (2.57 g) obtained in Synthesis Example 1 in 1,3-bistrifluoromethylbenzene / methanol (v / v, 10 / 1), an aqueous solution (25 mL) in which potassium hydroxide (1.29 g) and potassium ferricyanide (2.72 g) were dissolved was added, and the mixture was stirred for 1 hour under nitrogen in the dark. The organic layer was separated, and the aqueous layer was extracted with Novec (registered trademark) 7200 / methanol (10 / 1, v / v). The obtained organic layer was dried over magnesium sulfate, and the volatile components were distilled off under reduced pressure, followed by drying to obtain initiator 1 (yellow solid, yield 0.25 g, 10%).

[0247] 1H NMR (500MHz, Novec® 7200 / MeOH (10 / 1, v / v)) δ 10.22 (bs, 1H), 9.93 (bs, 1H), 8.03-7.62 (m, 26H), 7.38 (bs, 2H). 19 F NMR (470 MHz, (1,3-bistrifluoromethylbenzene / MeOH (10 / 1, v / v)) δ -54.26, -54.86, -57.58, -80.40, -82.12, -91.20, -92.86, -128.15, -131.79. Fluorine content: 52.2%, Fluorine content / oxygen content ratio: 3.2

[0248] Synthesis Example 2 The PFPE compound (4.32 g) was dissolved in 1,3-bistrifluoromethylbenzene (10 mL), and the solution was added with 4-RC. 6 H 4 CH 2 NH 2 (In the formula, R is 4-methyl-5-phenyl-1H-imidazol-2-yl.) (0.75 g) was added to a THF solution (40 mL) and stirred at room temperature under nitrogen for 21 hours. The solvent was then distilled off, and the remaining solid was washed with methanol at 60°C and dried to obtain the target compound as a yellow solid (4.36 g, 91%).

[0249] 1 H NMR (500MHz, Novec® 7200 / MeOH (10 / 1, v / v)) δ 10.23(bs), 8.42(bs, 2H), 8.13(bs, 2H), 7.92(bs, 4H), 7.77(m, 1H), 2.95(s, 3H). 19 F NMR (470 MHz, (1,3-bistrifluoromethylbenzene / MeOH (10 / 1, v / v)) δ -54.30, -55.90, -57.62, -80.75, -82.52, -91.23, -92.89, -128.18, -131.88. Fluorine content: 53.6%, Fluorine content / oxygen content ratio: 3.2

[0250] Example 2 To a solution (25 mL) of the compound (2.47 g) obtained in Synthesis Example 2 in 1,3-bistrifluoromethylbenzene / methanol (v / v, 10 / 1), an aqueous solution (25 mL) in which potassium hydroxide (1.47 g) and potassium ferricyanide (2.68 g) were dissolved was added, and the mixture was stirred for 1 hour under nitrogen in the dark. The organic layer was separated, and the aqueous layer was extracted with Novec (registered trademark) 7200 / methanol (10 / 1, v / v). The obtained organic layer was dried over sodium sulfate, and the volatile components were distilled off under reduced pressure, followed by drying to obtain initiator 2 (yellow solid, yield 0.44 g, 18% yield).

[0251] 19 F NMR (470 MHz, (1,3-bistrifluoromethylbenzene / MeOH (10 / 1, v / v)) δ -54.25, -55.84, -57.56, -61.31, -76.11, -81.59, -82.21, -83.88, -88.21, -91.20, -92.85, -128.70, -128.93. Fluorine content: 53.6%, Fluorine content / oxygen content ratio: 3.2

[0252] Synthesis Example 3 The PFPE compound (0.43 g) was dissolved in 1,3-bistrifluoromethylbenzene (3 mL), and the solution was added with 4-RC. 6 H 4 CH 2 NH 2 (wherein R is 4-methyl-5-(4-nitrophenyl)-1H-imidazol-2-yl) (78 mg) in THF (5 mL) was added and stirred overnight at room temperature under nitrogen for 21 hours. The solvent was then distilled off, and the remaining solid was washed three times with methanol and once with dichloromethane and dried to obtain the target compound as an orange solid (0.40 g, 82%).

[0253] 1H NMR (500MHz, Novec® 7200 / MeOH (10 / 1, v / v)) δ 10.25(bs), 8.81(bs, 2H), 8.55(bs, 1H), 8.47(bs, 1H), 8.40(bs, 2H), 8.10(bs, 1H), 7.97(bs, 1H), 3.06(s, 3H). 19 F NMR (470 MHz, (1,3-bistrifluoromethylbenzene / MeOH (10 / 1, v / v)) δ -54.20, -55.81, -57.53, -61.31, -81.40, -81.65, -82.25, -87.66, -91.14, -92.79. Fluorine content: 52.5%, Fluorine content / oxygen content ratio: 3.0

[0254] Example 3 To a solution (7 mL) of the compound (0.40 g) obtained in Synthesis Example 3 in 1,3-bistrifluoromethylbenzene / methanol (v / v, 10 / 1), an aqueous solution (3 mL) in which potassium hydroxide (0.13 g) and potassium ferricyanide (0.25 g) were dissolved was added, and the mixture was stirred for 1 hour under nitrogen in the dark. The organic layer was separated, and the aqueous layer was extracted with Novec (registered trademark) 7200 / methanol (10 / 1, v / v). The obtained organic layer was dried over sodium sulfate, and the volatile components were distilled off under reduced pressure, followed by drying to obtain initiator 3 (orange solid), yield 0.224 g, 56% yield).

[0255] 1 H NMR (500MHz, Novec® 7200 / MeOH (10 / 1, v / v)) δ 8.85-7.34(bs, 16H), 3.05-2.87(m, 6H). 19 F NMR (470 MHz, (1,3-bistrifluoromethylbenzene / MeOH (10 / 1, v / v)) δ -54.20, -55.81, -57.53, -61.31, -81.65, -91.13, -92.79. Fluorine content: 52.6%, Fluorine content / oxygen content ratio: 3.0

[0256] Synthesis Example 4 The PFPE compound (12.56 g) was dissolved in 1,3-bistrifluoromethylbenzene (100 mL), and an aqueous solution (100 mL) of sodium hydroxide (6.06 g) was added. After stirring overnight, concentrated hydrochloric acid (20 mL) diluted with water (60 mL) was added and stirred, the aqueous layer was removed, and the organic layer was washed with water and acetone, and then the volatile components were distilled off under reduced pressure to obtain a white powder of dicarboxylic acid type PFPE (12.24 g).

[0257] 19 F NMR (470 MHz, (1,3-bistrifluoromethylbenzene / MeOH (10 / 1, v / v)) δ -55.92, -57.59, -61.31, -76.20, -81.59, -83.94, -88.19, -91.27, -92.96.

[0258] Example 4 The dicarboxylic acid type PFPE (5.08 g) obtained in Synthesis Example 4 was dissolved in 1,3-bistrifluoromethylbenzene (10 mL), thionyl chloride (1 mL) and DMF (40 μL) were added, and the mixture was refluxed for 3 hours. Thionyl chloride (2 mL) was added, and the mixture was refluxed for another 3.5 hours, then cooled, and the volatile components were distilled off under reduced pressure. 1,3-bistrifluoromethylbenzene (5 mL) was added to the reaction mixture, and the mixture was ice-cooled, and methoxydiphenylphosphine (2 mL) was added and stirred overnight. The reaction mixture was washed once with methanol, twice with acetone, and once with water, and the volatile components were distilled off under reduced pressure to obtain initiator 4 (transparent oily compound, 1.71 g).

[0259] 1 H NMR (500MHz, Novec® 7200 / MeOH (10 / 1, v / v)) δ 8.45-8.00(m). 19 F NMR (470 MHz, (1,3-bistrifluoromethylbenzene / MeOH (10 / 1, v / v)) δ -54.23, -55.83, -57.55, -61.31, -81.69, -82.39, -91.16, -92.82. Fluorine content: 55.0%, Fluorine content / oxygen content ratio: 3.1

[0260] Synthesis Example 5 As the PFPE diol compound, the following compound was prepared. HOCH 2 -CF 2 -(OC 2 F 4 ) m -(OCF 2 ) n -CH 2 OH (m≒19, n≒28) PFPE diol compound (4.0 g), sodium hydroxide (0.80 g), and 1,3-bistrifluoromethylbenzene (4 mL) were added and stirred at 65° C. for 4 hours. 4-Bromobenzyl bromide (2.5 g) was added to the resulting suspension and stirred at 65° C. for an additional 6 hours. After returning to room temperature, the suspension was filtered, and the filtrate was washed with water and acetone in that order, and the volatile components were distilled off under reduced pressure to obtain ROCH 2 -CF 2 -(OC 2 F 4 ) m -(OCF 2 ) n -CH 2 OR (wherein R is 4-bromobenzyl) (3.32 g) was obtained.

[0261] 1 H NMR (500 MHz, 1,3-bistrifluoromethylbenzene / CDCl 3 (20 / 1, v / v)) δ 7.49(d, 1H), 7.37(d, 1H), 7.20(d, 1H), 7.08(d, 1H), 4.62(d, 1H), 4.49(d, 1H), 3.81(d, 1H), 3.68(d, 1H). Fluorine content: 55.7%, Fluorine content / oxygen content ratio: 3.2

[0262] Synthesis Example 6 A Novec 7200 solution (10 mL) of the compound (1.5 g) obtained in Synthesis Example 5 was cooled to -40°C, and n-butyllithium (2.3 M, cyclohexane solution, 1 mL) was slowly added dropwise to this solution using a syringe. After stirring at -40°C for 2 hours, the resulting solution was stirred at -40°C for 1 hour while passing carbon dioxide gas through it, and then at room temperature for 1 hour. The resulting solution was washed with methanol / 3 M hydrochloric acid (v / v, 10 / 1) and acetone in that order, and then filtered. The filtrate was concentrated and dried under reduced pressure to give a transparent oily ROCH 2 -CF 2 -(OC 2 F 4 ) m -(OCF 2 ) n -CH 2 OR (PFPE with a terminal carboxylic acid) (1.4 g) was obtained. In the formula, R is the following group and is bonded on the left side. [ka]

[0263] 1 H NMR (500 MHz, 1,3-bistrifluoromethylbenzene / CDCl 3 (20 / 1, v / v)) δ 7.49(m), 7.40(m), 7.19(br), 7.10(br), 4.68-4.45(br), 3.87-3.64(br). Fluorine content: 56.6%, Fluorine content / oxygen content ratio: 3.0

[0264] Example 5 The compound synthesized in Synthesis Example 6 (PFPE with carboxylic acid at both ends) (1.2 g) and thionyl chloride (1 mL) were added and refluxed for 0.5 hours. After cooling, the volatile components were distilled off under reduced pressure, Novec 7200 (5 mL) was added, the mixture was ice-cooled, methoxydiphenylphosphine (0.5 mL) was added, and the mixture was stirred overnight. The reaction mixture was washed with methanol, acetone, and water in that order, and then dried over sodium sulfate. The volatile components were distilled off under reduced pressure and dried to give initiator 5 (ROCH 2 -CF 2 -(OC 2 F4 ) m -(OCF 2 ) n -CH 2 OR, a clear oily compound was obtained, where R is the group below, attached at the left side. [ka]

[0265] 1 H NMR (500MHz, Novec® 7200 / MeOH (10 / 1, v / v)) δ 7.49(d), 7.42(m), 7.36(d), 7.20(br), 7.13(br), 7.07(d), 4.61(s), 4.54(br), 4.48 (s), 3.86-3.59(br). Fluorine content: 52.9%, Fluorine content / oxygen content ratio: 3.1

[0266] [Synthesis of fluorine-containing polymerizable monomers] The polymerizable monomers were synthesized based on WO 2020 / 162332 and WO 2020 / 162323. [ka]

[0267] [Preparation of the composition] The fluorine polymerizable monomer and the initiator were mixed at a given ratio (weight ratio) to prepare a mixed solution, which was then evaluated as follows. The composition of the mixed solution is shown in the table below.

[0268] [Table 1]

[0269] [Compatibility test] The mixture was prepared and allowed to stand at room temperature for 1 hour, after which the compatibility was evaluated according to the following criteria. ◯ (Good): The mixture is clear and homogeneous. × (bad): The mixture separates or a solid precipitates in the liquid.

[0270] [Table 2]

[0271] [Cureability test] The light of each wavelength was irradiated as follows. The 365 nm light was emitted from Asahi Spectroscopy Corporation's 300 W xenon light source MAX-350, which was filtered with Asahi Spectroscopy Corporation's LX0365 filter (HQBP365-UV). The 270 nm light was emitted from Asahi Spectroscopy Co., Ltd.'s 300 W xenon light source MAX-350, filtered by Asahi Spectroscopy Co., Ltd.'s LX0270 filter (HQBP270-UV). The 254 nm light was emitted from Asahi Spectroscopy Corporation's 300 W xenon light source MAX-350, filtered by Asahi Spectroscopy Corporation's LX0254 filter (HQBP254-UV).

[0272] After forming a 200μm film on a glass plate with an applicator, a glass plate was attached to the surface to block air. Then, ultraviolet rays of various wavelengths were irradiated. After that, the curing state of the coating film was evaluated. ○: Hardens and becomes a film. ×: Curing was insufficient and the product remained in a liquid state.

[0273] [Table 3]

[0274] [Table 4] [Industrial Applicability]

[0275] The compounds of the present disclosure can be used in a wide range of applications, such as sealants, adhesives, compatibilizers, water repellent materials, coatings, potting gels, and rubber materials such as O-rings, packings, gaskets, diaphragms, valves, and seals.

Claims

1. Formula (S1), (S2) or (S3): 【Chemistry 1】 [In the formula: R Ｆ１ each independently represents a monovalent organic group containing a fluorine atom, R Ｆ２ each independently represents a divalent organic group containing a fluorine atom, L １ each independently represents a monovalent radical-forming group, L ２ are each independently a group containing a divalent radical-forming group. A fluorine-containing compound represented by the formula: The fluorine content is 50% by mass or more, The fluorine content / oxygen content ratio is 2.0 to 10.0; The minimum bond dissociation energy between atoms is 300 kJ / mol or less. Fluorine-containing compound.

2. L １ are each independently -X １ -L Ｒ１ and X １ is a divalent group having no single bond or no amide bond, L Ｒ１ is a monovalent radical-forming group, The fluorine-containing compound according to claim 1.

3. X １ are each independently Single bond, C １－６ an alkylene group, or -(CH ２ ) ｚ１ -O-(CH ２ ) ｚ２ - [In the formula, z1 is an integer from 0 to 6, z2 is an integer from 0 to 6, Here, at least one of z1 and z2 is 1 or more. The fluorine-containing compound according to claim 2,

4. L １ are each independently -X １ -L Ｒ１ and X １ each independently represents a single bond or the following formula: -(R ５１ ) ｐ５ -(R ５２ ) ｑ５ - [In the formula: R ５１ is a single bond, C １－２０ an alkylene group, or an o-, m- or p-phenylene group; R ５２ each independently represents -O-, -S-, o-, m- or p-phenylene group, -COO-, -OCO-, -CONR ５４ --, --NR ５４ CO-, -O-CONR ５４ --, --NR ５４ CO-O- and -NR ５４ - is a group selected from the group consisting of R ５４ are each independently a hydrogen atom, a phenyl group, or C １－６ is an alkyl group, p5 is an integer from 0 to 6, q5 is an integer from 0 to 6, Here, at least one of p5 and q5 is 1 or more, and the order of the repeating units enclosed in parentheses with p5 or q5 is arbitrary. is a divalent organic group represented by L Ｒ１ is a monovalent radical-forming group, The fluorine-containing compound according to claim 1.

5. X １ are each independently Single bond, C １－６ an alkylene group, or -(CH ２ ) ｚ１ -R ５３ -(CH ２ ) ｚ２ - [In the formula, R ５３ is O, -COO-, -OCO-, -CONR ５４ - or -NR ５４ CO-, R ５４ are each independently a hydrogen atom, a phenyl group, or C １－６ is an alkyl group, z1 is an integer from 0 to 6, z2 is an integer from 0 to 6, Here, at least one of z1 and z2 is 1 or more. The fluorine-containing compound according to claim 4, wherein

6. L ２ is -R ２ -R ４ -L Ｒ２ -R ４ -R ２ - is a group represented by R ２ each independently represents an alkylene group, an oxygen atom, —COO—, —OCO—, or —CONR １１ - or -NR １１ CO-, R １１ is a hydrogen atom or C １－６ is an alkyl group, R ４ are each independently a single bond or a divalent organic group, L Ｒ２ The fluorine-containing compound according to claim 1 , wherein:

7. The monovalent radical generating groups are each independently selected from the following groups: 【Chemistry 2】 [In the formula: Y is a single bond or a divalent organic group; W １ is an oxygen atom, or NR ２５ and W ２ is OR ２５ , or NR ２５ ２ and R ２５ are each independently a hydrogen atom or a hydrocarbon group, R ２０ is a hydrogen atom or a monovalent organic group, R ２２ are each independently a hydrogen atom or a monovalent organic group, R ２３ are each independently a hydrogen atom or a monovalent organic group, R ２４ are each independently a hydrogen atom or a monovalent organic group; １ is an arylene group, Ar ２ is an aryl group, However, R in the formula ２２ and R ２２ , R ２３ and R ２３ , R ２４ and R ２４ , R ２５ and R ２５ , or Ar １ and Ar ２ may be linked via a linker L, L is a single bond or C １－６ -(C ｓ H ２ｓ ) ｘ - (X ３ ) ｙ - (C ｔ H ２ｔ ) ｚ -, phenylene, or naphthylene; X ３ is O, S, or NH, s is an integer from 1 to 6; t is an integer from 1 to 6, x, y, and z are each independently 0 or 1; However, at least one of x, y, and z is 1. The fluorine-containing compound according to claim 1,

8. The divalent radical generating groups are each independently selected from the following groups: 【Chemistry 3】 [In the formula: Y is a single bond or a divalent organic group; W １ is an oxygen atom or NR ２５ and W ２ is OR ２５ , or NR ２５ ２ and R ２２ is a hydrogen atom or a monovalent organic group, R ２３ are each independently a hydrogen atom or a monovalent organic group, or two R ２３ may be bonded to form a ring, R ２４ is a hydrogen atom or a monovalent organic group, R ２５ is a hydrogen atom, an oxygen atom, or a hydrocarbon group, R ２６ is a divalent organic group, Ar １ are each independently an arylene group; However, R in the formula ２３ and R ２３ , R ２５ and R ２５ , or Ar １ and Ar １ may be linked via a linker L, L is a single bond or C １－６ -(C ｓ H ２ｓ ) ｘ - (X ３ ) ｙ - (C ｔ H ２ｔ ) ｚ -, phenylene, or naphthylene; X ３ is O, S, or NH, s is an integer from 1 to 6; t is an integer from 1 to 6, x, y, and z are each independently 0 or 1; However, at least one of x, y, and z is 1. The fluorine-containing compound according to claim 1 , wherein the fluorine-containing compound is a group comprising:

9. The divalent radical generating group is the following group: 【Chemistry 4】 [In the formula: Ar ５ each independently represents a phenyl group which may have a substituent, Ar ６ each independently represents a phenylene group which may have a substituent, R ３１ are each independently １－６ is a hydrocarbon group, R ３２ each independently represents a single bond or C １－６ is an alkylene group. The fluorine-containing compound according to claim 1,

10. 2. The fluorine-containing compound according to claim 1, wherein the monovalent radical-forming group and the divalent radical-forming group are groups that generate radical species when irradiated with light having a wavelength of 200 to 500 nm.

11. R Ｆ１ are each independently R Ｆ３ - (Z １ -R Ｆ４ ) ｋ - and R Ｆ２ are each independently -R Ｆ４ - (Z １ -R Ｆ４ ) ｋ - and R Ｆ３ Each independently represents Rf １ -R Ｆ -O ｑ - and R Ｆ４ Each independently represents -Rf ２ ｐ -R Ｆ -O ｑ - and Rf １ C optionally substituted with one or more fluorine atoms １－１６ is an alkyl group, Rf ２ C optionally substituted with one or more fluorine atoms １－６ is an alkylene group, R Ｆ are each independently a divalent fluoropolyether group, p is 0 or 1; Each q is independently 0 or 1; Z １ are each independently a single bond or a divalent organic group, Each k is independently an integer from 0 to 20. The fluorine-containing compound according to claim 1.

12. Z １ The fluorine-containing compound according to claim 11 , wherein each of the groups independently represents a group containing a divalent radical-forming group.

13. R Ｆ each independently represents the following formula (f1), (f2), (f3), (f4), (f5), or (f6): -(OC ３ F ６ ) ｄ -(OC ２ F ４ ) ｅ - (f1) [In the formula, d is an integer of 1 to 200, and e is 0 or 1.] -(OC ４ F ８ ) ｃ -(OC ３ F ６ ) ｄ -(OC ２ F ４ ) ｅ -(OCF ２ ) ｆ - (f2) [In the formula, c and d each independently represent an integer of 0 to 30; e and f are each independently an integer from 1 to 200; The sum of c, d, e and f is an integer from 10 to 200; The order of occurrence of each repeat unit enclosed in parentheses with the subscript c, d, e, or f is arbitrary in the formula. -(R ６ -R ７ ) ｇ - (f3) [In the formula, R ６ is O.C.F. ２ Or O.C. ２ F ４ and R ７ , O.C. ２ F ４ , O.C. ３ F ６ , O.C. ４ F ８ , O.C. ５ F １０ and O.C. ６ F １２ or a combination of two or three groups selected from these groups; g is an integer from 2 to 100. -(R ６ -R ７ ) ｇ -R ｒ -(R ７’ -R ６’ ) ｇ’ - (f4) [In the formula, R ６ is O.C.F. ２ Or O.C. ２ F ４ and R ７ , O.C. ２ F ４ , O.C. ３ F ６ , O.C. ４ F ８ , O.C. ５ F １０ and O.C. ６ F １２ or a combination of two or three groups independently selected from these groups; R ６’ is O.C.F. ２ Or O.C. ２ F ４ and R ７’ , O.C. ２ F ４ , O.C. ３ F ６ , O.C. ４ F ８ , O.C. ５ F １０ and O.C. ６ F １２ or a combination of two or three groups independently selected from these groups; g is an integer from 2 to 100; g' is an integer from 2 to 100, R ｒ teeth, 【Chemistry 5】 (In the formula, * indicates the bond position.) is.]; -(OC ６ F １２ ) ａ -(OC ５ F １０ ) ｂ -(OC ４ F ８ ) ｃ -(OC ３ F ６ ) ｄ -(OC ２ F ４ ) ｅ -(OCF ２ ) ｆ - (f5) [In the formula, e is an integer of 1 or more and 200 or less, a, b, c, d, and f are each independently an integer of 0 or more and 200 or less, the sum of a, b, c, d, e, and f is at least 1, and the order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula.] -(OC ６ F １２ ) ａ -(OC ５ F １０ ) ｂ -(OC ４ F ８ ) ｃ -(OC ３ F ６ ) ｄ -(OC ２ F ４ ) ｅ -(OCF ２ ) ｆ - (f6) [In the formula, f is an integer of 1 or more and 200 or less, a, b, c, d, and e are each independently an integer of 0 or more and 200 or less, the sum of a, b, c, d, e, and f is at least 1, and the order of the repeating units enclosed in parentheses with a, b, c, d, e, or f is arbitrary in the formula.] The fluorine-containing compound according to claim 11, wherein the fluorine-containing compound is a group represented by the following formula:

14. 2. The fluorine-containing compound according to claim 1, which has a number average molecular weight of 1,000 to 100,000.

15. The fluorine-containing compound according to claim 1 , wherein the lowest bond dissociation energy among bond dissociation energies for each bond in the fluorine-containing compound is 185 kJ / mol or less.

16. (i) a fluorine-containing compound according to any one of claims 1 to 15, and (ii) Fluorine-containing polymerizable monomer 1. A curable composition comprising:

17. The curable composition according to claim 16, wherein the SP values ​​of the fluorine-containing compound and the fluorine-containing polymerizable monomer are in the range of 6.0 to 7.

4.

18. 17. The curable composition of claim 16, having a solvent content of 20% or less by weight.

19. The curable composition according to claim 16, wherein the fluorine-containing polymerizable monomer is a compound having a fluoropolyether group and a (meth)acrylate group.

20. The fluorine-containing polymerizable monomer is represented by the following formula (M): (CH ２ =CR ７１ -O-) ｍ１ -X ７ -R Ｆ７２ -X ７ -(OCO-CR ７１ =CH ２ ) ｍ１ [In the formula: R Ｆ７２ is -Rf ２ ｐ -R Ｆ -O ｑ - and Rf ２ C optionally substituted with one or more fluorine atoms １－６ is an alkylene group, R Ｆ are each independently a divalent fluoropolyether group, p is 0 or 1; Each q is independently 0 or 1; R ７１ are each independently a hydrogen atom or C １－６ is an alkyl group, X ７ are each independently a divalent to pentavalent organic group, Each m1 is independently an integer from 1 to 4. The curable composition according to claim 16, wherein the compound is represented by the formula:

21. The curable composition according to claim 16, wherein the fluorine-containing compound is 0.1 to 50 parts by mass based on 100 parts by mass of the fluorine-containing polymerizable monomer.

22. A cured product obtained by curing the curable composition according to claim 16.

23. Mixing the fluorine-containing compound according to any one of claims 1 to 15 with a fluorine-containing polymerizable monomer to obtain a mixture; The method for producing a cured product includes irradiating the mixture with light having a wavelength of 200 to 500 nm to obtain a cured product.

24. The method for producing a cured product according to claim 23, wherein the mixture has a solvent content of 20% by mass or less.

25. Formula (S3a): A-R Ｆ２ -A [In the formula: R Ｆ２ is a divalent organic group containing a fluorine atom, Each A is independently represented by the following formula: 【Chemistry 6】 (In the formula, R ２３ are each independently a hydrogen atom or a monovalent organic group, or two R ２３ may be bonded to form a ring, Y is a single bond or a divalent organic group; However, R ２３ and at least one of Y does not contain a phenyl group. It is a group containing a group represented by the following formula: A compound represented by the formula:

26. Each A is independently -R ７ -R ８ -R ９ and R ７ represents an alkylene group, an oxygen atom, -COO-, or -CONR １１ - and R １１ is a hydrogen atom or C １－６ is an alkyl group, R ８ is a single bond or a divalent organic group, R ９ is represented by the following formula: 【Chemistry 7】 (In the formula, R ２３ are each independently a hydrogen atom or a monovalent organic group, or two R ２３ may be bonded to form a ring, Y is a single bond or a divalent organic group; However, R ２３ and at least one of Y does not contain a phenyl group. is a group represented by 26. The compound of claim 25.

27. R Ｆ２ are each independently -R Ｆ４ - (Z １ -R Ｆ４ ) ｋ - and R Ｆ４ Each independently represents -Rf ２ ｐ -R Ｆ -O ｑ - and Rf ２ C optionally substituted with one or more fluorine atoms １－６ is an alkylene group, R Ｆ are each independently a divalent fluoropolyether group, p is 0 or 1; Each q is independently 0 or 1; Z １ are each independently a single bond or a divalent organic group, Each k is independently an integer from 0 to 20.

27. A compound according to claim 25 or 26.

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