Fluorine-containing aromatic polymer and method for producing fluorine-containing aromatic polymer

Abstract

Fluorine-containing aromatic polymers, being used in a wide variety of applications, are desired to have various structures. A fluorine-containing aromatic polymer according to the present disclosure is represented by formula (I).

Description

Fluorine-containing aromatic polymer and method for producing the same

[0001] The present disclosure relates to fluorinated aromatic polymers and methods for producing fluorinated aromatic polymers.

[0002] Super engineering plastics such as polyimides and aromatic polymers typified by engineering plastics have excellent properties such as heat resistance, mechanical properties, insulating properties, etc. Patent Document 1 describes, as polyimides, reaction products of acid anhydrides with amines including dimer diamines.

[0003] Japanese Patent Application Laid-Open No. 2020-203981

[0004] Fluorine-containing aromatic polymers are desired to have a variety of structures since they are used in a wide range of applications.

[0005] The present disclosure includes the following aspects: <1> A compound represented by the following formula (I): In formula (I), A each independently represents an aliphatic or aromatic imido-diyl group in each occurrence, and Ar each independently represents a C group optionally having one or more substituents. ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and L, in each occurrence, is independently -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, １ each occurrence independently represents a C which may have one or more substituents １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０represents an aromatic hydrocarbon group or a hydrogen atom, k each independently represents an integer of 0 to 4 in each occurrence, l each independently represents an integer of 1 to 4 in each occurrence, m each independently represents an integer of 0 to 4 in each occurrence, n represents an integer of 1 or more, and in the unit enclosed in parentheses with n, the units enclosed in parentheses with k, l and m may appear in any order, and the following (i) and (ii): (i) k is 0, and in formula (I), one or more C ２－２０ (ii) k is 1 or more and 4 or less, and one or more C １－２０ <2> The fluorine-containing aromatic polymer represented by the formula (I) above satisfies any one of the following conditions: ２－２０ The fluorine-containing organic group is represented by the following formula (1A) and formula (1B): R ３１ -X １ - (R Ｆ１ ) ｒ -CF ２ -* (1A) *-X ３ -CF ２ -* (1B) [In formula (1A) and formula (1B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group, ３１ is a C optionally substituted by one or more halogen atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ each occurrence independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, and the number of carbon atoms contained in formula (1A) or formula (1B) is 2 or more and 20 or less. １－２０ The fluorine-containing organic group is represented by the following formula (2A) and formula (2B): ３２ -X １ - (R Ｆ１ ) ｒ -CF ２ -* (2A) *-X １ -CF ２ -* (2B) [In formula (2A) and formula (2B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３２ is a C optionally substituted by one or more halogen atoms;１－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ each occurrence independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, and the number of carbon atoms contained in formula (2A) or formula (2B) is 1 or more and 20 or less. ２－２０ The fluorine-containing organic group is represented by the following formula (1-a), formula (1-b), formula (1-c) and formula (1B): F-X ３ -CF ２ -* (1-a) R ３１ -X １ -CF ２ -* (1-b) R ３１ -X １ -R Ｆ１ -CF ２ -* (1-c) *-X ３ -CF ２ -* (1B) [In formula (1-a), formula (1-b), and formula (1-c) and formula (1B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑRf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３ is a C optionally substituted by one or more halogen atoms; ３－１６ represents an alkylene group, ３１ is a C optionally substituted by one or more halogen atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom or a bromine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ each occurring independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, the number of carbon atoms contained in formula (1-a) is 2 or more and 20 or less, the number of carbon atoms contained in formula (1-b) is 2 or more and 20 or less, the number of carbon atoms contained in formula (1-c) is 2 or more and 20 or less, and the number of carbon atoms contained in formula (1B) is 2 or more and 20 or less.] １－２０The fluorine-containing organic group is represented by the following formula (2-a), formula (2-b), formula (2-c) and formula (2B): F-X １ -CF ２ -* (2-a) R ３２ -X １ -CF ２ -* (2-b) R ３２ -X １ -R Ｆ１ -CF ２ -* (2-c) *-X １ -CF ２ -* (2B) [in formula (2-a), formula (2-b), formula (2-c) and formula (2B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３２ is a C optionally substituted by one or more halogen atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom or a bromine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ each occurring independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, the number of carbon atoms contained in formula (2-a) is 1 or more and 20 or less, the number of carbon atoms contained in formula (2-b) is 1 or more and 20 or less, the number of carbon atoms contained in formula (2-c) is 1 or more and 20 or less, and the number of carbon atoms contained in formula (2B) is 1 or more and 20 or less. [In formula (I-a), A ａ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ａ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, na represents an integer of 1 or more, and １－２０ <5> The fluorine-containing aromatic polymer according to any one of <1> to <3>, wherein the formula (I) is represented by the following formula (I-b): [In formula (I-b), Ar ｂ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｂ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, １ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, nb represents an integer of 1 or more, and ２－２０ <6> The fluorine-containing aromatic polymer according to any one of <1> to <3>, wherein the formula (I-b) is represented by the following formula (I-b1), (I-b2), (I-b3), (I-b4), (I-b5), (I-b6), or (I-b7): [In formula (I-b1), (I-b2), (I-b3), (I-b4), (I-b5), (I-b6) or (I-b7), Ar ｂ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, nb represents an integer of 1 or more, and in formulae (I-b1), (I-b2), (I-b3), (I-b4), (I-b5), (I-b6) and (I-b7), each of them contains one or more C ２－２０ <7> The fluorine-containing aromatic polymer according to <5>, wherein the formula (I) is represented by the following formula (I-c): [In formula (I-c), Ar ｃ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｃ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｃ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR２ represents one selected from the group consisting of -, ｃ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of Ar ｃ１ and Ar ｃ２ and L ｃ１ and L ｃ２ In at least one combination of R １ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, nc represents an integer of 1 or more, and ２－２０ <8> The fluorine-containing aromatic polymer according to any one of <1> to <3>, wherein the formula (I-c) is represented by the following formula (I-c1), (I-c2), or (I-c3): [In formula (I-c1), (I-c2) or (I-c3), Ar ｃ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｃ２ each occurrence independently represents a C which may have one or more substituents ６－２０represents a divalent group containing an aromatic hydrocarbon group, each occurrence of nc independently represents an integer of 1 or more, and in formulas (I-c1), (I-c2) and (I-c3), each of them contains one or more C ２－２０ <9> The fluorine-containing aromatic polymer according to <7>, wherein the formula (I) is represented by the following formula (I-d): [In formula (I-d), Ar ｄ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｄ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｄ３ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｄ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, ｄ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, ｄ３ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２represents one selected from the group consisting of Ar ｄ１ , Ar ｄ２ and Ar ｄ３ and L ｄ１ , L ｄ２ and L ｄ３ In at least one combination of the above, one group is a group different from at least one of the other two groups, and R １ each occurrence independently represents a C which may have one or more substituents １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, nd represents an integer of 1 or more, and ２－２０ <10> The fluorine-containing aromatic polymer according to any one of <1> to <3>, wherein the formula (I-d) is represented by the following formula (I-d1) or (I-d2): [In formula (I-d1) or (I-d2), Ar ｄ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｄ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｄ３ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, nd independently represents an integer of 1 or more in each occurrence, and in formulas (I-d1) and (I-d2), each of them contains one or more C ２－２０<11> The fluorine-containing aromatic polymer according to <9>, wherein the formula (I) is represented by the following formula (I-e): [In formula (I-e), Ar ｅ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｅ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, ｅ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, ｅ３ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, １ each occurrence independently represents a C which may have one or more substituents １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０represents an aromatic hydrocarbon group or a hydrogen atom, ne represents an integer of 1 or more, and ２－２０ <12> The fluorine-containing aromatic polymer according to any one of <1> to <3>, wherein the formula (I-e) is represented by the following formula (I-e1), (I-e2), or (I-e3): [wherein in formula (I-e1), (I-e2) or (I-e3), Ar ｅ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, R ７ is a C which may have one or more substituents １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ each occurrence of ne independently represents an integer of 1 or more; and in formula (I-e1), (I-e2) or (I-e3), each of C ２－２０ <13> The fluorine-containing aromatic polymer according to <11>, wherein the formula (I) is represented by the following formula (I-g): [In formula (Ig), Ar ｇ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｇ１ is a C which may have one or more substituents ３－１６ represents a divalent group containing an alicyclic hydrocarbon group, mg each independently represents an integer of 0 to 4, ng1 represents an integer of 1 or more, ng2 represents an integer of 1 or more, and ２－２０ <14> The fluorine-containing aromatic polymer according to any one of <1> to <3>, wherein the formula (I) is represented by the following formula (I-h): [In formula (Ih), A ｈrepresents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ｈ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｈ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, １ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, nh represents an integer of 1 or more, and １－２０ <15> The fluorine-containing aromatic polymer according to any one of <1> to <3>, wherein the formula (I-h) is represented by the following formula (I-h1): [In formula (I-h1), A ｈ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ｈ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, each occurrence of nh independently represents an integer of 1 or more, and in formula (I-h1), each occurrence of nh independently represents an integer of 1 or more. １－２０ <16> A is a fluorine-containing aromatic polymer represented by the following formula (A2-I): [In formula (A2-I), A １０ represents a single bond or a divalent organic group, and * represents a bond.] or the following formula (A2-II): <17> A fluorine-containing aromatic polymer according to any one of <1> to <15>, represented by the following formula: [in formula (A2-II), * represents a bond.] １０ is a single bond and formulas (a-1) to (a-7): [In formulas (a-1) to (a-7), R ３ is C optionally substituted by a fluorine atom １－１６ <18> A is one selected from groups represented by the following formulae (A1-1) to (A1-19): [In the formulae (A1-1) to (A1-19), * represents a bond.] <10> The fluorine-containing aromatic polymer according to any one of <1> to <17>, wherein the fluorine-containing aromatic polymer is one selected from groups represented by the following formula (I-1): [In formula (I-1), A １ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar １ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, １ is independently at each occurrence -R １１ -, -O-, -S-, -NR １２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR １２ —CO— and CO—NR １２ represents one selected from the group consisting of -, １１ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, １２each occurrence independently represents an optionally substituted C １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, k1 each independently represents an integer of 0 to 4 in each occurrence, l1 each independently represents an integer of 1 to 4 in each occurrence, m1 each independently represents an integer of 0 to 4 in each occurrence, n1 represents an integer of 1 or more, in the unit enclosed in parentheses with n1, the units enclosed in parentheses with k1, l1, and m1 may appear in any order, and in formula (I-1), one or more C １－２０ The present invention provides a method for producing a fluorine-containing aromatic polymer represented by the following formula (I-2): [In formula (I-2), A ２ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and L, in each occurrence, is independently -R ２１ -, -O-, -S-, -NR ２２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２２ —CO— and CO—NR ２２ represents one selected from the group consisting of -, ２１ each occurrence independently represents a C which may have one or more substituents １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０represents an aromatic hydrocarbon group or a hydrogen atom, k2 each independently represents an integer of 0 to 4 in each occurrence, l2 each independently represents an integer of 1 to 4 in each occurrence, m2 each independently represents an integer of 0 to 4 in each occurrence, n2 represents an integer of 1 or more, and in the unit enclosed in parentheses with n2, the units enclosed in parentheses with k2, l2, and m2 may appear in any order.] and an aromatic polymer represented by the following formula (II): I-R ｆ１ (II) [In formula (II), R ｆ１ is C １－２０ <20> A production method comprising reacting a compound represented by the following formula (I-1): [In formula (I-1), A １ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar １ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, １ is independently at each occurrence -R １１ -, -O-, -S-, -NR １２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR １２ —CO— and CO—NR １２ represents one selected from the group consisting of -, １１ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, １２ each occurrence independently represents an optionally substituted C １－１６ an alkyl group, optionally having one or more substituents; ６－２０represents an aromatic hydrocarbon group or a hydrogen atom, k1, in each occurrence, independently represents an integer of 0 or more and 4 or less, l1, in each occurrence, independently represents an integer of 1 or more and 4 or less, m1, in each occurrence, independently represents an integer of 0 or more and 4 or less, n1 represents an integer of 1 or more, in the unit enclosed in parentheses with n1, the units enclosed in parentheses with k1, l1, and m1 may appear in any order, and in formula (I-1), １－２０ The present invention relates to a method for producing a fluorine-containing aromatic polymer represented by the following formula (II): ｆ１ (II) [In formula (II), R ｆ１ is C １－２０ <21> A production method comprising: reacting a compound represented by formula (III): R with a compound represented by formula (III): ４ -Ar ３ -R ４ (III) [In formula (III), Ar ３ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, R ４ is independently at each occurrence -OH, -NH ２ , and represents a fluorine atom or a chlorine atom.]. <22> The method according to <20> or <21>, comprising reacting the fluorine-containing aromatic monomer with a second monomer to obtain a fluorine-containing aromatic polymer. <23> The method according to <22>, wherein the second monomer is a monomer having two or more groups capable of reacting with an amino group or a hydroxyl group in one molecule. <24> The method according to <25>, wherein the second monomer is a monomer represented by the following formula (IV): R ５ -L １０ -R ５ (IV) [In formula (IV), R ５are each independently in each occurrence the following formulas (r-1) to (r-18): [In formulas (r-1) to (r-18), * represents a bond.], L １０ are expressed by the following formulas (l-1) to (l-11): [In formulas (l-1) to (l-11), R ６ is a C optionally substituted by one or more fluorine atoms; １－１６ an alkylene group or a divalent C group optionally having one or more substituents; ６－２０ <25> The method according to <22> or <23>, wherein the compound is a compound represented by the following formula (III-1): [In formula (III-1), Ar ３１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, R ４１ is independently at each occurrence -OH, -NH ２ , a glycidyloxy group, a fluorine atom, or a chlorine atom; １－２０ The C １－２０ The fluorine-containing organic group is represented by the following formulas (2-1A) and (2B): ３３ -X １ - (R Ｆ１ ) ｒ -CF ２ -* (2-1A) *-X １ -CF ２ -* (2B) [In formulas (2-1A) and (2B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆrepresents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３３ is a C which may have one or more substituents ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ each occurrence independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, the number of carbon atoms contained in formula (2-1A) is 1 or more and 20 or less, and the number of carbon atoms contained in formula (2B) is 1 or more and 20 or less.]. <26> A fluorine-containing aromatic monomer comprising a substrate and a layer formed on a surface of the substrate by a surface treatment agent, wherein the substrate comprises an aromatic polymer, and the surface treatment agent is a fluorine-containing aromatic monomer represented by one or more of the following formulas (II-1A) and (II-1B): R ３２ -X １ - (R Ｆ１ ) ｒ -CF ２ -I (II-1A) I-X １ -CF ２ -I (II-1B) [In formula (II-1A) and formula (II-1B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O)ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３２ is a C optionally substituted by one or more halogen atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ each occurring independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, the number of carbon atoms contained in formula (II-1A) is 1 or more and 20 or less, and the number of carbon atoms contained in formula (II-1B) is 1 or more and 20 or less. ] An article comprising one or more compounds represented by a group selected from the following. <27> A method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising a method for producing an article comprising the ... ３２ -X １ - (R Ｆ１ ) ｒ -CF２ -I (II-1A) I-X １ -CF ２ -I (II-1B) [In formula (II-1A) and (formula II-1B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３２ is a C optionally substituted by one or more halogen atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ each occurring independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, the number of carbon atoms contained in formula (II-1A) is 1 or more and 20 or less, and the number of carbon atoms contained in formula (II-1B) is 1 or more and 20 or less.

[0006] According to the present disclosure, novel fluorine-containing aromatic polymers having various structures can be provided.

[0007] (Fluorine-Containing Aromatic Polymer) The fluorine-containing aromatic polymer of the present disclosure is represented by the following formula (I): In formula (I), A each independently represents an aliphatic or aromatic imido-diyl group in each occurrence, and Ar each independently represents a C group optionally having one or more substituents. ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and L, in each occurrence, is independently -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, １ each occurrence independently represents a C which may have one or more substituents １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, k each independently represents an integer of 0 to 4 in each occurrence, l each independently represents an integer of 1 to 4 in each occurrence, m each independently represents an integer of 0 to 4 in each occurrence, n represents an integer of 1 or more, and in the unit enclosed in parentheses with n, the units enclosed in parentheses with k, l and m may appear in any order, and the following (i) and (ii): (i) k is 0, and in formula (I), one or more C ２－２０ (ii) k is 1 or more and 4 or less, and one or more C １－２０and (iii) the compound satisfies any one of the following conditions.

[0008] According to the present disclosure, novel fluorine-containing aromatic polymers can be provided in which fluorine-containing organic groups are introduced into various aromatic polymers. In particular, since the fluorine-containing aromatic polymers can have various structures, the range of structural options is expanded, and it is expected that new aromatic polymers (particularly super engineering plastics and engineering plastics) can be provided that have improved properties such as flexibility, adhesion (reactivity) and affinity with other materials, low dielectric properties, transparency, water and oil repellency, low tack, antifouling properties, solvent solubility, and high surface hardness.

[0009] A, in each occurrence, independently represents an aliphatic or aromatic imido-diyl group, i.e., A has the formula: In the formula, * represents a bond (hereinafter, also referred to as an "imido-N-yl group").

[0010] A preferably represents an aliphatic or aromatic imido-diyl group containing one or more imido rings, and the aliphatic or aromatic imido-diyl group may have one or more substituents. The imido ring is a ring containing an imido-N-yl group and may be monocyclic or polycyclic, and the number of imido bonds contained in one imido ring may be one or more than two. The number of ring members of such an imido ring may be preferably 5 to 20, more preferably 5 to 15, and even more preferably 5 to 10.

[0011] Examples of the imide ring include a 2,5-dioxopyrrolidine ring, a 1,3-dioxohexahydroisoindoline ring, a 1,2,3,4-cyclobutyltetracarboxylic acid diimide ring, a 1,2,4,5-cyclopentyltetracarboxylic acid diimide ring, a hexahydropyromellitic acid diimide ring, a 1,3-dioxoisoindoline ring, a pyromellitic acid diimide ring, and a 1,4,5,8-naphthalenetetracarboxylic acid diimide ring, and the like, with a 2,5-dioxopyrrolidine ring and a 1,3-dioxoisoindoline ring being preferred.

[0012] The number of imide rings contained in the aliphatic or aromatic imido-diyl group is preferably 1 or 2, and more preferably 2. The substituents that the aliphatic or aromatic imido-diyl group represented by A may have will be described later.

[0013] The above A is preferably represented by the following formula (A1-I): [In formula (A1), A １０ represents a single bond or a divalent organic group, R １０ represents a substituent, n10 represents an integer of 0 to 3, and * represents a bond.] or a group represented by the following formula (A1-II): [In formula (A1), R １０ represents a substituent, n10 represents an integer of 0 to 3, and * represents a bond.

[0014] When A is a group represented by formula (A1-I) or (A1-II), the heat resistance of the fluorine-containing aromatic polymer can be improved.

[0015] A １０ represents a single bond or a divalent organic group. The organic group may be a C １－１６ an alkylene group, optionally having one or more substituents; ６－２０ Divalent groups containing aromatic hydrocarbon groups, -O-, -CO-, -C≡C-, and -SO ２ -, and groups combining these groups.

[0016] The C optionally substituted with a fluorine atom １－１６ "C" in the alkylene group １－１６ The "alkylene group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－１０ alkylene groups, more preferably straight or branched C １－５ alkylene group, and in one embodiment, branched C ２－４ It is preferably an alkylene group, and in another embodiment, it is preferably a methylene group.

[0017] The C optionally substituted with one or more fluorine atoms１－１６ The alkylene group is preferably —CH ２ -, -C(CH ３ ) ２ -, -CF ２ -, C(CF ３ ) ２ - is.

[0018] C which may have one or more of the above-mentioned substituents ６－２０ "C" in a divalent group containing an aromatic hydrocarbon group ６－２０ The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic ring, two or more rings may or may not form a condensed ring. ６－２０ The number of aromatic hydrocarbon groups contained in the divalent group containing an aromatic hydrocarbon group is 1 or more, preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. Such aromatic hydrocarbon groups are preferably C ６－１０ It is an aromatic hydrocarbon group, more preferably a phenylene group, a tolylene group, a xylylene group, or a naphthylene group, and in one embodiment, it is more preferably a phenylene group, a tolylene group, or a xylylene group, and in another embodiment, it may be more preferably a naphthylene group.

[0019] C which may have one or more of the above-mentioned substituents ６－２０ In the divalent group containing an aromatic hydrocarbon group, two or more aromatic hydrocarbon groups may be bonded via a single bond or an organic group. Such an organic group may be a linear or branched C １－４ The above-mentioned A is an alkyl group. １０ C which may have one or more substituents represented by ６－２０ The substituents in the divalent group containing an aromatic hydrocarbon group will be described later. １０ The substituent represented by the formula will be described later.

[0020] In one embodiment, A １０ It is preferable that A has no substituent. That is, A is preferably a group represented by the following formula (A2-I) or (A2-II). １０has the same meaning as above. In formulas (A1) and (A2), A １０ is preferably a single bond and a group represented by the formulas (a-1) to (a-7): [In formulas (a-1) to (a-7), R ３ is C optionally substituted by a fluorine atom １－１６ represents an alkylene group, and * represents a bond.

[0021] R ３ is C optionally substituted by a fluorine atom １－１６ represents an alkylene group, and １－１６ "C" in the alkylene group １－１６ The "alkylene group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－１０ alkylene groups, more preferably straight or branched C １－５ Among these, A is preferably a group represented by formula (a-3) or formula (a-7).

[0022] A is preferably represented by the following formulae (A1-1) to (A1-19): [In the formulae (A1-1) to (A1-19), * represents a bond.]

[0023] Ar, in each occurrence, independently represents a C group which may have one or more substituents. ６－２０ represents a divalent group containing an aromatic hydrocarbon group. C which may have one or more of the above-mentioned substituents ６－２０ "C" in a divalent group containing an aromatic hydrocarbon group ６－２０ The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic ring, two or more rings may or may not form a condensed ring. ６－２０In a divalent group containing an aromatic hydrocarbon group, the number of aromatic hydrocarbon groups is 1 or more, preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. Such an aromatic hydrocarbon group is preferably C ６－１０ It is an aromatic hydrocarbon group, more preferably a phenylene group, a tolylene group, a xylylene group or a naphthylene group, and even more preferably a phenylene group, a tolylene group or a xylylene group.

[0024] C which may have one or more such substituents ６－２０ In the divalent group containing an aromatic hydrocarbon group, two or more aromatic hydrocarbon groups may be bonded via a single bond or a divalent organic group. Such an organic group may be a linear or branched C １－４ Examples of suitable alkyl groups include:

[0025] Ar preferably has the following formula (Ar1): [In formula (Ar1), Ar １１ is a divalent C which may have one or more substituents. ６－１０ represents an aromatic hydrocarbon group, １２ each occurrence independently represents a divalent C which may have one or more substituents. ６－１０ represents an aromatic hydrocarbon group, １０ represents a single bond, —O—, —CO—, or —SO ２ - or C １－４ represents an alkylene group, n11 represents an integer of 0 or more and 3 or less, * represents a bond, and the total number of carbon atoms in formula (Ar1) is 6 or more and 20 or less.

[0026] Ar １１ is a divalent C which may have one or more substituents. ６－１０ represents an aromatic hydrocarbon group. ６－２０ "Divalent C" in aromatic hydrocarbon group ６－２０The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic group, two or more rings may not form a condensed ring or may form a condensed ring. ６－２０ "Divalent C" in aromatic hydrocarbon group ６－２０ The aromatic hydrocarbon group is preferably a divalent C ６－１５ An aromatic hydrocarbon group, more preferably a divalent C ６－１０ Ar is an aromatic hydrocarbon group, more preferably a phenylene group, a tolylene group, a xylylene group, or a naphthylene group, and even more preferably a phenylene group, a tolylene group, or a xylylene group. １１ Divalent C represented by ６－１０ The substituents that the aromatic hydrocarbon group may have will be described later.

[0027] Ar １２ each occurrence independently represents a divalent C which may have one or more substituents. ６－１０ represents an aromatic hydrocarbon group. ６－２０ "Divalent C" in aromatic hydrocarbon group ６－２０ The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic group, two or more rings may not form a condensed ring or may form a condensed ring. ６－２０ "Divalent C" in aromatic hydrocarbon group ６－２０ The aromatic hydrocarbon group is preferably a divalent C ６－１５ An aromatic hydrocarbon group, more preferably a divalent C ６－１０ Ar is an aromatic hydrocarbon group, more preferably a phenylene group, a tolylene group, a xylylene group, or a naphthylene group, and even more preferably a phenylene group, a tolylene group, or a xylylene group. １２ Divalent C represented by ６－１０ The substituents that the aromatic hydrocarbon group may have will be described later.

[0028] X １０ represents a single bond, —O—, —CO—, or —SO ２ - or C １－４It represents an alkylene group. １－４ The alkylene group may be a straight or branched chain, and is preferably a straight or branched C １－３ Alkylene groups, specifically —CH ２ -, -C(CH ３ ) ２ -. C represented by Ar ６－２０ The substituents that the divalent group containing an aromatic hydrocarbon group may have will be described later.

[0029] Ar is preferably a phenylene group, a tolylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a biphenylene group, a 3,3'-dimethylbiphenylene group, a 2,2'-dimethylbiphenylene group, a 2,2'-dimethoxybiphenylene group, a 3,3',5,5'-tetramethylbiphenylene group, a 3,3',5,5'-tetraethylbiphenylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone group, phenylene-4,4'-diyl group, diphenylsulfone-4,4'-diyl group, or oxybisphenyl-4,4'-diyl group, and more preferably a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, benzophenone-4,4'-diyl group, diphenylsulfone-4,4'-diyl group, or oxybisphenyl-4,4'-diyl group.

[0030] L is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ - represents one kind selected from the group consisting of

[0031] R １ each occurrence independently represents a C which may have one or more substituents １－１６ an alkylene group and a C group optionally having one or more substituents;３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group.

[0032] C which may have one or more of the above-mentioned substituents １－１６ "C" in the alkylene group １－１６ The "alkylene group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－１０ alkylene groups, more preferably straight or branched C １－５ In one embodiment, the C １－３ Alkylene groups, specifically, —CH ２ -, -CH ２ CH ２ -, -CH ２ CH ２ CH ２ -It can be.

[0033] C which may have one or more of the above-mentioned substituents １－１６ The alkylene group may be substituted with one or more fluorine atoms. １ is preferably a C substituted by one or more fluorine atoms １－１６ is a fluoroalkylene group, more preferably C １－１６ A perfluoroalkylene group, more preferably C １－６ perfluoroalkylene groups, more preferably C １－３ It is a perfluoroalkylene group.

[0034] Above C １－１６ The perfluoroalkylene group may be a straight chain or a branched chain, and preferably is a straight chain or branched chain C １－６ perfluoroalkylene groups, more preferably straight-chain or branched-chain C １－３ Perfluoroalkylene groups, specifically —CF ２ -, -CF ２ CF ２ -, -CF ２ CF ２ CF ２ -, -CF ２ CF (CF ３ ) -, -C(CF３ ) ２ - is. R １ C represented by １－１６ Other substituents that the alkylene group may have will be described later.

[0035] C which may have one or more of the above-mentioned substituents ３－１６ "C" in a divalent group containing an alicyclic hydrocarbon group ３－１６ The "alicyclic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic group, two or more rings may or may not form bridged rings. ３－１６ In the divalent group containing an alicyclic hydrocarbon group, the number of alicyclic hydrocarbon groups is 1 or more, preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. Such a divalent group containing an alicyclic hydrocarbon group, preferably a divalent C ３－１６ is an alicyclic hydrocarbon group, more preferably a divalent C ６－１２ Alicyclic hydrocarbon groups are more preferably cyclohexanediyl groups, decahydronaphthyl groups, isobornyl groups, tricyclo[5.2.1.0] groups, 2,6 ] may be a decanediyl group or an adamantyl group.

[0036] C which may have one or more of the above-mentioned substituents ３－１６ In a divalent group containing an alicyclic hydrocarbon group, two or more alicyclic hydrocarbon groups may be bonded via a single bond or a divalent organic group. Such an organic group may be a linear or branched C １－４ Examples of suitable alkyl groups include:

[0037] The above R １ C represented by ３－１６ In one embodiment, the divalent group containing an alicyclic hydrocarbon group is a C ３－１６ In another embodiment, a C ３－１６ R is a divalent group containing an alicyclic hydrocarbon group. １ C represented by ３－１６ The substituents that the divalent group containing an alicyclic hydrocarbon group may have will be described later.

[0038] In one embodiment, the R １ is a C having no substituents １－１６ In another embodiment, the R １ is a C having a substituent １－１６ In yet another embodiment, the R １ is a divalent C having no substituents １－１６ It may be an alicyclic hydrocarbon group.

[0039] R ２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom. C which may have one or more of the above-mentioned substituents １－１６ "C" in the 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 １－１０ alkyl group, more preferably a straight or branched C １－５ is an alkyl group, and in one embodiment is a straight or branched C １－４ It is an alkyl group, specifically, —CH ３ , -CH ２ CH ３ , -CH ２ CH ２ CH ３ , -CH(CH ３ ) ２ , -CH ２ CH ２ CH ２ CH ３ , -CH ２ CH (CH ３ ) ２ , -CH(CH ３ ) ３ It could be.

[0040] In one embodiment, R ２ is a C having no substituents １－１６ In another embodiment, R ２ is a C having a substituent １－１６ It may be an alkyl group.

[0041] C optionally having one or more substituents １－１６ The alkyl group may be substituted with one or more fluorine atoms. ２ is preferably a C substituted by one or more fluorine atoms １－１６ fluoroalkyl group, more preferably C １－１６ is a perfluoroalkyl group, more preferably C １－６ perfluoroalkyl groups, more preferably C １－４ A perfluoroalkyl group, specifically, —CF ３ , -CF ２ CF ３ , -CF ２ CF ２ CF ３ , -CF(CF ３ ) ２ , -CF ２ CF ２ CF ２ CF ３ , -CF ２ CF (CF ３ ) ２ , -CF(CF ３ ) ３ It can be. R ２ C represented by １－１６ Other substituents that the alkyl group may have will be described later.

[0042] C optionally having one or more substituents ６－２０ "C" in the aromatic hydrocarbon group ６－２０ The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic ring, two or more rings may or may not form a condensed ring. ６－２０ The aromatic hydrocarbon group is preferably C ６－１０ It is an aromatic hydrocarbon group, more preferably a phenylene group, a tolylene group, a xylylene group, or a naphthylene group, and in one embodiment, it is more preferably a phenylene group, a tolylene group, or a xylylene group, and in another embodiment, it may be more preferably a naphthylene group.

[0043] C ６－２０ The substituent that the aromatic hydrocarbon group may have includes a hydroxyl group.

[0044] L is preferably —O—, —S—, —CO—, —O—CO—O—, or —SO ２ -, -NR ２ —CO— and CO—NR ２ - is one selected from the group consisting of

[0045] an aliphatic or aromatic imido-diyl group represented by A, C represented by Ar ６－２０ A divalent group containing an aromatic hydrocarbon group, A １０ C represented by ６－２０ A divalent group containing an aromatic hydrocarbon group, Ar １１ C represented by ６－１０ Aromatic hydrocarbon group, Ar １２ C represented by ６－１０ Aromatic hydrocarbon group, R １ C represented by １－１６ Alkylene group, R ２ C represented by １－１６ The alkyl group may have a substituent. ６－２０ A divalent group containing an aromatic hydrocarbon group, A １０ C represented by ６－２０ A divalent group containing an aromatic hydrocarbon group, Ar １１ C represented by ６－１０ Aromatic hydrocarbon groups and Ar １２ C represented by ６－１０ Substituents that the aromatic hydrocarbon group may have; and R １０ Examples of the substituent represented by the formula: １－２０ Fluorine-containing organic group or C ２－２０ Fluorine-containing organic group; C optionally substituted with one or more fluorine atoms １－１６ an alkyl group; a C group optionally substituted with one or more fluorine atoms; ６－２０ Aromatic hydrocarbon group; C １－１６ Alkoxy group; C １－１６ Examples of R include one or more selected from a hydroxyalkyl group, a hydroxyl group, a carboxy group, a glycidyl group, and a fluorine atom.１ C represented by １－１６ Alkylene group, R １ C represented by ３－１６ A divalent group containing an alicyclic hydrocarbon group and R ２ C represented by １－１６ The substituents that the alkyl group may have include C １－２０ Fluorine-containing organic group or C ２－２０ Fluorine-containing organic group; C ６－２０ The C represented by Ar may be one or more selected from the group consisting of an aromatic hydrocarbon group, a hydroxyl group, and a fluorine atom. ６－２０ A divalent group containing an aromatic hydrocarbon group, Ar １１ C represented by ６－１０ Aromatic hydrocarbon groups and Ar １２ C represented by ６－１０ The aromatic hydrocarbon group may be modified with oil such as cashew oil, linseed oil, castor oil, or linseed oil.

[0046] Above C １－２０ Fluorine-containing organic group or C ２－２０ The fluorine-containing organic group is an organic group containing fluorine atoms, and may contain hydrogen atoms or oxygen atoms in addition to fluorine atoms and carbon atoms.

[0047] Above C ２－２０ The fluorine-containing organic group is preferably represented by the following formula (1A) or formula (1B): ３１ -X １ - (R Ｆ１ ) ｒ -CF ２ -* (1A) *-X ３ -CF ２ -* (1B) [In formula (1A) and formula (1B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group, R ３１ is a C optionally substituted by one or more halogen atoms; １－１６an alkyl group, optionally having one or more substituents; ６－２０ Aromatic hydrocarbon group, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group, ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ each occurrence independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, and the number of carbon atoms contained in formula (1A) or formula (1B) is 2 or more and 20 or less. １－２０ The fluorine-containing organic group is preferably represented by the following formula (2A) and formula (2B): R ３２ -X １ - (R Ｆ１ ) ｒ -CF ２ -* (2A) *-X １ -CF ２ -* (2B) [In formula (2A) and formula (2B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group, R ３２ is a C optionally substituted by one or more halogen atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０ Aromatic hydrocarbon group, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ each occurring independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, and the number of carbon atoms contained in formula (2A) or formula (2B) is 1 or more and 20 or less.

[0048] Above C ２－２０ Fluorine-containing organic group or the above C １－２０ When the fluorine-containing organic group is a divalent group, that is, a group represented by formula (1B) or formula (2B), the two bonds of such a group can typically be bonded to different carbon atoms. ２－２０ Fluorine-containing organic group or the above C １－２０ The fluorine-containing organic group is Ar, A １０ , Ar １１ or Ar １２When the group represented by formula (1B) or (2B) is bonded to an aromatic hydrocarbon group represented by the formula (1B) or (2B), the group may form a ring together with the aromatic hydrocarbon group.

[0049] When the fluorine-containing organic group has the above structure, it is possible to provide a fluorine-containing aromatic polymer excellent in various properties such as flexibility, adhesion (reactivity) and affinity with other materials, low dielectric properties, transparency, water and oil repellency, low adhesion, antifouling properties, solvent solubility, high surface hardness, etc. In particular, when the fluorine-containing organic group has a structure represented by formula (2B), it is possible to provide a fluorine-containing aromatic polymer excellent in various properties such as rigidity, low thermal expansion coefficient, low dielectric properties, transparency, water and oil repellency, low adhesion, antifouling properties, solvent solubility, high surface hardness, etc.

[0050] R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Represents -.

[0051] Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms. １－１６ Represents an alkylene group.

[0052] The C optionally substituted with one or more fluorine atoms １－１６ "C" in the alkylene group １－１６ The "alkylene group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－６ alkylene groups, more preferably linear C １－３ It is an alkylene group.

[0053] The Rf is preferably a C substituted with one or more fluorine atoms. １－１６ is a fluoroalkylene group, more preferably C １－１６ A perfluoroalkylene group, more preferably C １－６ perfluoroalkylene groups, more preferably C １－３ It is a perfluoroalkylene group.

[0054] Above C １－１６The perfluoroalkylene group may be a straight chain or a branched chain, and preferably is a straight chain or branched chain C １－６ perfluoroalkylene groups, more preferably straight-chain or branched-chain C １－３ Perfluoroalkylene groups, specifically, —CF ２ -, -CF ２ CF ２ -, CF ２ CF ２ CF ２ -, CF ２ CF (CF ３ )-.

[0055] R Ｆ represents a divalent fluoro(poly)ether group. In the present disclosure, the fluoro(poly)ether group means a fluoroether group and / or a fluoropolyether group. The fluorine-containing polymer of the present disclosure is Ｆ By including the above, the properties of the fluoro(poly)ether group can be imparted, and the flexibility, heat resistance, friction characteristics, stain resistance, and water and oil repellency can be improved.

[0056] R Ｆ is preferably represented by the formula: -(OC ４ F ８ ) ｃ - (OC ３ R Ｆａ ６ ) ｄ - (OC ２ F ４ ) ｅ -(OCF ２ ) ｆ - [In the formula: R Ｆａ are each independently a hydrogen atom, a fluorine atom, or a chlorine atom in each occurrence, and c, d, e, and f are each independently an integer of 0 to 200, and the sum of c, d, e, and f is 1 or more. The order of occurrence of each repeating unit enclosed in parentheses with c, d, e, or f is arbitrary in the formula. However, all R Ｆａ is a hydrogen atom or a chlorine atom, then at least one of c, e and f is 1 or more.] (hereinafter also referred to as a group represented by "PFPE").

[0057] R Ｆａis preferably a hydrogen atom or a fluorine atom, and more preferably a fluorine atom. Ｆａ is a hydrogen atom or a chlorine atom, at least one of c, e and f is 1 or more.

[0058] Preferably, c, d, e and f are each independently an integer of 0 to 100, or an integer of 0 to 20.

[0059] 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. The sum of c, d, e, and f is preferably 200 or less, more preferably 100 or less, even more preferably 60 or less, and may be, for example, 50 or less, 30 or less, or even 20 or less.

[0060] These repeating units may be linear or branched. For example, -(OC ４ F ８ )- is -(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 ))-. ３ F ６ ) - (i.e., in the above formula, RＦａ is a fluorine atom) is -(OCF ２ CF ２ CF ２ )-,-(OCF(CF ３ )CF ２ )-and-(OCF ２ CF (CF ３ ))-, and -(OCF(CF ３ )CF ２ )-and-(OCF ２ CF (CF ３ ))-. ２ F ４ )- is -(OCF ２ CF ２ )-and-(OCF(CF ３ ))-.

[0061] In one embodiment, R Ｆ is independently in each occurrence a group represented by the following formula (f1): ３ F ６ ) ｄ -(OCF ２ ) ｆ (f1) [wherein d is an integer from 0 to 200, and f is an integer from 1 to 200];

[0062] OC in the above formula (f1) ３ F ６ is preferably (OCF ２ CF ２ CF ２ ), (OCF(CF ３ )CF ２ ) or (OCF ２ CF (CF ３ )), more preferably (OCF ２ CF (CF ３)). In the above formula (f1), d is preferably an integer of 0 to 100, more preferably 0 to 50, and even more preferably 0 to 10. In one embodiment, d is 0. In another embodiment, d is preferably 1 to 100, more preferably 2 to 50, and even more preferably 3 to 10. In the above formula (f1), f is preferably 1 to 100, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3. In one embodiment, f is 1.

[0063] p is 0 or 1. In one embodiment, p is 0. In another embodiment, p is 1. q is 0 or 1. In one embodiment, q is 0. In another embodiment, q is 1. r is 0 or 1. In one embodiment, r is 0. In another embodiment, r is 1.

[0064] X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond. C which may be substituted with one or more halogen atoms １－１６ "C" in the alkylene group １－１６ The "alkylene group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－１０ alkylene groups, more preferably straight or branched C １－５ alkylene group, and in one embodiment, branched C ２－４ In another embodiment, it is a linear C ２－５ An alkylene group is preferred.

[0065] C optionally substituted by one or more halogen atoms １－１６ Examples of the halogen atom in the alkylene group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and preferred are a fluorine atom and an iodine atom.

[0066] C optionally substituted by one or more halogen atoms １－１６ The alkylene group is preferably —CF ２ -, -CF ２CF ２ -, -CF(CF ３ ) -, -CF ２ CF ２ CF ２ -, -CF ２ CF (CF ３ ) -, -CF ２ CF ２ CF ２ CF ２ -, -CF ２ CF ２ CF ２ CF ２ CF ２ - or CHI-CH ２ -CF ２ CF ２ CF ２ -, more preferably -CF ２ CF ２ -, -CF(CF ３ ) -, -CF ２ CF (CF ３ ) -, -CF ２ CF ２ CF ２ CF ２ CF ２ - or CHI-CH ２ -CF ２ CF ２ CF ２ - is.

[0067] X １ is preferably a straight or branched chain C １－１０ A straight-chain or branched-chain C alkylene group or a single bond, which may be substituted with one or more atoms selected from fluorine atoms and iodine atoms, is more preferably １－５ It is an alkylene group or a single bond.

[0068] X ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond. C which may be substituted with one or more halogen atoms １－１６ "C" in the alkylene group １－１６ The "alkylene group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C１－１０ alkylene groups, more preferably straight or branched C １－５ alkylene group, and in one embodiment, branched C ２－４ In another embodiment, it is a linear C ２－５ An alkylene group is preferred.

[0069] C optionally substituted by one or more halogen atoms １－１６ Examples of the halogen atom in the alkylene group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and preferred are a fluorine atom and an iodine atom.

[0070] C optionally substituted by one or more halogen atoms １－１６ The alkylene group is preferably —CF ２ -, -CF ２ CF ２ -, -CF(CF ３ ) -, -CF ２ CF ２ CF ２ -, -CF ２ CF (CF ３ ) -, -CF ２ CF ２ CF ２ CF ２ -, -CF ２ CF ２ CF ２ CF ２ CF ２ - or CHI-CH ２ -CF ２ CF ２ CF ２ -, more preferably -CF ２ CF ２ -, -CF(CF ３ ) -, -CF ２ CF (CF ３ ) -, -CF ２ CF ２ CF ２ CF ２ CF ２ - or CHI-CH ２ -CF ２ CF ２ CF ２ - is.

[0071] X ３ is preferably a straight or branched chain C １－１０ It is an alkylene group, more preferably a straight-chain or branched-chain C alkylene group optionally substituted with one or more atoms selected from fluorine atoms and iodine atoms. １－５ It is an alkylene group.

[0072] R ３１ is a C optionally substituted by one or more halogen atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ３２ is a C optionally substituted by one or more halogen atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom.

[0073] The above R ３１ , R ３２ C optionally substituted with one or more halogen atoms represented by １－１６ "C" in the 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 １－１０ alkyl group, more preferably a straight or branched C １－６is an alkyl group, and in one embodiment is a straight or branched C １－４ It is an alkyl group, specifically, —CH ３ , -CH ２ CH ３ , -CH ２ CH ２ CH ３ , -CH(CH ３ ) ２ , -CH ２ CH ２ CH ２ CH ３ , -CH ２ CH (CH ３ ) ２ , -CH(CH ３ ) ３ It could be.

[0074] C optionally substituted by one or more halogen atoms １－１６ Examples of the halogen atom in the alkyl group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and preferred examples include a fluorine atom and an iodine atom.

[0075] In one embodiment, the C optionally substituted by one or more halogen atoms １－１６ The alkyl group is a C １－１６ In another embodiment, the C alkyl group optionally substituted with one or more halogen atoms is １－１６ The alkyl group is preferably a C substituted with one or more fluorine atoms. １－１６ fluoroalkyl group, more preferably C １－１６ is a perfluoroalkyl group, more preferably C １－６ It is a perfluoroalkyl group.

[0076] Above C １－１６ The perfluoroalkyl group may be a straight or branched chain, and is preferably a straight or branched C １－１０ perfluoroalkyl groups, more preferably straight-chain or branched-chain C １－６ A perfluoroalkyl group, specifically, —CF ３ , -CF ２ CF３ , -CF ２ CF ２ CF ３ , -CF(CF ３ ) ２ , -CF ２ CF ２ CF ２ CF ３ , -CF ２ CF (CF ３ ) ２ , -CF(CF ３ ) ３ It could be.

[0077] The above R ３１ , R ３２ C which may have one or more substituents represented by ６－２０ "C" in the aromatic hydrocarbon group ６－２０ The aromatic hydrocarbon group may be monocyclic or polycyclic, and in the case of a polycyclic group, two or more rings may not form a condensed ring or may form a condensed ring. ６－２０ "C" in the aromatic hydrocarbon group ６－２０ The aromatic hydrocarbon group is preferably C ６－１５ An aromatic hydrocarbon group, more preferably C ６－１０ It is an aromatic hydrocarbon group, and more preferably a phenyl group.

[0078] C which may have one or more of the above-mentioned substituents ６－２０ Substituents in the aromatic hydrocarbon group include halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms; １－４ Alkyl group; C １－４ Alkoxy group; R ２０ -O-CO- (where R ２０ is C １－４ R is an alkyl group, preferably a halogen atom, and particularly preferably a fluorine atom. ２０ may be linear or branched, preferably linear or branched C １－３ It is an alkyl group, specifically, —CH ３ , -CH ２ CH ３ is preferred.

[0079] The above R ３１ , R ３２ C represented by ６－２０ The aromatic hydrocarbon group is preferably a C ６－１０ An aromatic hydrocarbon group, more preferably a C ６－１０ In one embodiment, the R ３１ , R ３２ C represented by ６－２０ The aromatic hydrocarbon group preferably has a substituent. In another embodiment, the R ３１ , R ３２ C represented by ６－２０ The aromatic hydrocarbon group preferably has no substituent.

[0080] The above R ３１ , R ３２ The "silsesquioxane residue" in the silsesquioxane residue which may have one or more substituents represented by the following formula is a monovalent group in which one substituent on Si in the silsesquioxane has been eliminated, and may have any of a cage structure, a ladder structure, or a random structure.

[0081] The substituent in the silsesquioxane residue which may have one or more substituents is preferably a C which may be substituted with one or more halogen atoms. １－１０ an alkyl group; a phenyl group, more preferably a C group optionally substituted with one or more halogen atoms; １－６ The alkyl group is a phenyl group.

[0082] C optionally substituted with one or more halogen atoms as a substituent of the silsesquioxane residue １－１０ "C" in the alkyl group １－１０ The "alkyl group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－８ alkyl group, more preferably a straight-chain C １－６ It is an alkyl group.

[0083] C optionally substituted with one or more halogen atoms as a substituent of the silsesquioxane residue １－１０ Examples of the halogen atom in the alkyl group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and preferred examples include a fluorine atom and an iodine atom.

[0084] C optionally substituted with one or more halogen atoms as a substituent of the silsesquioxane residue １－１０ The alkyl group is preferably -CHI-CH ２ -CF ２ CF ２ CF ２ -I.

[0085] As the substituent in the silsesquioxane residue which may have one or more substituents, a phenyl group or an isobutyl group is preferred.

[0086] R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, and preferably represents a C １－１６ represents an alkyl group.

[0087] The C optionally substituted with one or more fluorine atoms １－１６ "C" in the 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 １－１０ alkyl group, more preferably a straight or branched C １－５ alkyl group, and particularly preferably C １－２ It is an alkyl group.

[0088] The C optionally substituted with one or more fluorine atoms １－１６ The alkyl group is preferably a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group.

[0089] R ｆ３ is a C optionally substituted by one or more halogen atoms;１－１６ C which may be substituted with one or more halogen atoms. １－１６ "C" in the 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 １－１０ alkyl group, more preferably a straight or branched C １－５ alkyl group, and particularly preferably C １－２ It is an alkyl group.

[0090] C optionally substituted by one or more halogen atoms １－１６ Examples of the halogen atom in the alkyl group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferred.

[0091] The C optionally substituted with one or more fluorine atoms １－１６ The alkyl group is preferably a methyl group, an ethyl group, a trifluoromethyl group, or a pentafluoroethyl group.

[0092] R ｆ３ is preferably C optionally substituted by one or more halogen atoms. １－５ It is an alkyl group, a phenyl group, an alkoxy group, a hydroxy group, ONa, OK, a chlorine atom or a fluorine atom, and more preferably a fluorine atom.

[0093] R ｆ４ represents independently at each occurrence a hydrogen atom or a fluorine atom. ｆ４ is a hydrogen atom, and in another embodiment, R ｆ４ is a fluorine atom.

[0094] R ３１ , R ３２ is an iodine atom, in the unit represented by formula (I), R ３１ , R ３２ is replaced with a bond, and the R ３１ , R ３２ X bonded to １ is other aromatic ring (the above R ３１ , R ３２But, -X １ - (R Ｆ１ ) ｒ -CF ２ R is an aromatic ring other than a group bonded via -, for example, an aromatic ring contained in another unit represented by formula (I). Although the present disclosure should not be interpreted as being limited to a particular theory, the above structure is thought to be as follows. That is, in the method for producing a fluoropolymer of the present disclosure, it is thought that an iodine atom of the compound represented by formula (II) is abstracted to become a reaction site, which bonds to the aromatic ring of the unit represented by formula (I-1), thereby obtaining the structure represented by formula (I). R ３１ , R ３２ is an iodine atom, R ３１ , R ３２ It is believed that the iodine atom corresponding to R can be similarly abstracted and bonded to another aromatic ring. ３１ , R ３２ The same applies when an I atom is contained in the substituent of the group represented by the formula: and the group bonded to such an I atom may be bonded to another aromatic ring.

[0095] R ３１ is preferably C optionally substituted by one or more halogen atoms. １－１６ an alkyl group, optionally having one or more substituents; ６－２０ Aromatic hydrocarbon group, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom.

[0096] R ３２ is preferably C optionally substituted by one or more halogen atoms. １－１６ an alkyl group, optionally having one or more substituents; ６－２０ Aromatic hydrocarbon group, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４２ , a fluorine atom, a bromine atom, or an iodine atom. * represents a bond.

[0097] The total number of carbon atoms in formula (1A) may be 2 or more and 20 or less, preferably 3 or more and 15 or less, and more preferably 4 or more and 15 or less. It is believed that the fewer the number of carbon atoms, the more easily the properties of the aromatic polymer are maintained, and the greater the number of carbon atoms, the more easily the properties of the fluorine-containing organic group are exhibited. The total number of carbon atoms in formula (1B) may be 2 or more and 20 or less, preferably 3 or more and 10 or less, and more preferably 3 or more and 5 or less. It is believed that the fewer the number of carbon atoms, the more easily the properties of the aromatic polymer are maintained, and the greater the number of carbon atoms, the more easily the properties of the fluorine-containing organic group are exhibited. The total number of carbon atoms in formula (2A) may be 1 or more and 20 or less, and preferably 1 or more and 15 or less. It is believed that the fewer the number of carbon atoms, the more easily the properties of the aromatic polymer are maintained, and the greater the number of carbon atoms, the more easily the properties of the fluorine-containing organic group are exhibited. The total number of carbon atoms in formula (2B) may be 1 or more and 20 or less, preferably 3 or more and 10 or less, and more preferably 3 or more and 5 or less. It is believed that the fewer the number of carbon atoms, the more likely it is that the properties of the aromatic polymer are maintained, and the greater the number of carbon atoms, the more likely it is that the properties of the fluorine-containing organic group are exhibited.

[0098] C represented by the above formula (1A) ２－２０ The fluorine-containing organic group is C ４－２０ Fluoroalkyl groups, C having functional groups ２－２０ Fluorine-containing organic group, or C ４－２０ Specifically, the above formula (1A) and formula (1B) can be expressed by the following formulas (1-a), (1-b), (1-c), and (1B): F-X ３ -CF ２ -* (1-a) R ３１ -X １ -CF ２ -* (1-b) R ３１ -X １ -R Ｆ１ -CF ２-* (1-c) *-X ３ -CF ２ -* (1B) [in formula (1-a), formula (1-b), formula (1-c) and formula (1B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ２ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group; ３ is a C optionally substituted by one or more halogen atoms; ３－１６ represents an alkylene group, ３１ is a C optionally substituted by one or more fluorine atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom or a bromine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４are each independently in each occurrence a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, the number of carbon atoms contained in formula (1-a) is 2 or more and 20 or less, the number of carbon atoms contained in formula (1-b) is 2 or more and 20 or less, the number of carbon atoms contained in formula (1-c) is 2 or more and 20 or less, and the number of carbon atoms contained in formula (1B) is 2 or more and 20 or less.

[0099] C represented by the above formula (1A) ４－２０ When the fluorine-containing organic group is a group represented by formula (1-a), the fluorine-containing aromatic polymer can be given properties derived from a fluoroalkyl group, and C represented by the above formula (1A) ４－２０ When the fluorine-containing organic group is a group represented by formula (1-b), the fluorine-containing aromatic polymer can be given properties derived from a specific functional group, and C represented by the above formula (1A) can be ４－２０ When the fluorine-containing organic group is a group represented by formula (1-c), the fluorine-containing aromatic polymer can be endowed with properties derived from the fluoro(poly)ether group.

[0100] C represented by the above formula (2A) and formula (2B) １－２０ The fluorine-containing organic group is C １－２０ Fluoroalkyl groups, C having functional groups １－２０ Fluorine-containing organic group, or C １－２０ Specifically, the above formulas (2A) and (2B) can be expressed by the following formulas (2-a), (2-b), (2-c), and (2B): F-X １ -CF ２ -* (2-a) R ３２ -X １ -CF ２ -* (2-b) R ３２ -X １ -R Ｆ１ -CF ２ -* (2-c) *-X １ -CF ２ -* (2B) [in formula (2-a), formula (2-b), formula (2-c) and formula (2B), RＦ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３２ is a C optionally substituted by one or more fluorine atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom or a bromine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ are each independently in each occurrence a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, the number of carbon atoms contained in formula (2-a) is 1 or more and 20 or less, the number of carbon atoms contained in formula (2-b) is 1 or more and 20 or less, the number of carbon atoms contained in formula (2-c) is 1 or more and 20 or less, and the number of carbon atoms contained in formula (2B) is 1 or more and 20 or less.

[0101] C represented by the above formula (2A) ４－２０When the fluorine-containing organic group is a group represented by formula (2-a), the fluorine-containing aromatic polymer can be given properties derived from a fluoroalkyl group, and C represented by the above formula (2A) ４－２０ When the fluorine-containing organic group is a group represented by formula (2-b), the fluorine-containing aromatic polymer can be given properties derived from a specific functional group, and C represented by the above formula (2A) can be ４－２０ When the fluorine-containing organic group is a group represented by formula (2-c), the fluorine-containing aromatic polymer can be endowed with properties derived from the fluoro(poly)ether group.

[0102] X ３ is as defined above, and is preferably a straight-chain or branched-chain C ３－１０ It is an alkylene group, more preferably a straight-chain or branched-chain C alkylene group optionally substituted with one or more atoms selected from fluorine atoms and iodine atoms. ３－５ It is an alkylene group.

[0103] The aliphatic or aromatic imido-diyl group represented by A, C represented by Ar ６－２０ A divalent group containing an aromatic hydrocarbon group, A １０ C represented by ６－２０ A divalent group containing an aromatic hydrocarbon group, Ar １１ C represented by ６－１０ Aromatic hydrocarbon groups and Ar １２ C represented by ６－１０ Substituents that the aromatic hydrocarbon group may have; and R １０ C optionally substituted with one or more fluorine atoms as a substituent represented by １－１６ C in alkyl group １－１６ The alkyl group may be straight-chain or branched-chain, and is preferably a straight-chain or branched-chain C １－１０ alkyl group, more preferably a straight or branched C １－５ is an alkyl group, and in one embodiment is a straight or branched C １－４ It is an alkyl group, specifically, —CH ３ , -CH ２ CH ３ , -CH ２ CH ２ CH３ , -CH(CH ３ ) ２ , -CH ２ CH ２ CH ２ CH ３ , -CH ２ CH (CH ３ ) ２ , -CH(CH ３ ) ３ It could be.

[0104] C substituted with one or more fluorine atoms １－１６ The alkyl group is preferably C １－１６ fluoroalkyl group, more preferably C １－１６ perfluoroalkyl groups, more preferably straight-chain or branched-chain C １－１９ perfluoroalkyl groups, more preferably straight or branched C １－５ A perfluoroalkyl group, specifically, for example, —CF ３ , -CF ２ CF ３ , -CF ２ CF ２ CF ３ , -CF(CF ３ ) ２ , -CF ２ CF ２ CF ２ CF ３ , -CF ２ CF (CF ３ ) ２ , -C(CF ３ ) ３ It could be.

[0105] The C optionally substituted with one or more fluorine atoms １－１６ In one embodiment, the alkyl group is a C １－１６ is an alkyl group, and in another embodiment, C １－１６ It may be a fluoroalkyl group.

[0106] The aliphatic or aromatic imido-diyl group represented by A, C represented by Ar ６－２０ A divalent group containing an aromatic hydrocarbon group, A １０ C represented by６－２０ A divalent group containing an aromatic hydrocarbon group, Ar １１ C represented by ６－１０ Aromatic hydrocarbon groups and Ar １２ C represented by ６－１０ Substituents that the aromatic hydrocarbon group may have; and R １０ C which may have one or more of the above-mentioned substituents as the substituent represented by ６－２０ "C" in the aromatic hydrocarbon group ６－２０ The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic ring, two or more rings may or may not form a condensed ring. ６－２０ The aromatic hydrocarbon group is preferably C ６－１０ It is an aromatic hydrocarbon group, more preferably a phenylene group, a tolylene group, a xylylene group, or a naphthylene group, and in one embodiment, it is more preferably a phenylene group, a tolylene group, or a xylylene group, and in another embodiment, it may be more preferably a naphthylene group.

[0107] Above C ６－２０ Examples of the substituent that the aromatic hydrocarbon group may have include a hydroxyl group and a fluorine-containing organic group. Such a fluorine-containing organic group is preferably a group represented by the above formula (1A), formula (1B), formula (2A), or formula (2B), and more preferably a group represented by any of the above formulas (1-a), (1-b), (1-c), (1B), (2-a), (2-b), and (2-c) and (2B). In one aspect, the fluorine-containing organic group is preferably a group represented by the above formula (1A) or formula (2A), and more preferably a group represented by any of the above formulas (1-a), (1-b), (1-c), (2-a), (2-b), and (2-c).

[0108] The aliphatic or aromatic imido-diyl group represented by A, C represented by Ar ６－２０ A divalent group containing an aromatic hydrocarbon group, A １０ C represented by ６－２０ A divalent group containing an aromatic hydrocarbon group, Ar １１ C represented by ６－１０Aromatic hydrocarbon groups and Ar １２ C represented by ６－１０ Substituents that the aromatic hydrocarbon group may have; and R １０ C as a substituent represented by １－１６ The alkoxy group may be linear or branched, and is preferably a linear or branched C １－１０ is an alkoxy group, more preferably a straight or branched C １－５ In one embodiment, the C １－４ Alkoxy groups, specifically, —O—CH ３ , —O—CH ２ CH ３ , —O—CH ２ CH ２ CH ３ , —O—CH(CH ３ ) ２ , —O—CH ２ CH ２ CH ２ CH ３ , —O—CH ２ CH (CH ３ ) ２ , —O—CH(CH ３ ) ３ It could be.

[0109] The aliphatic or aromatic imido-diyl group represented by A, C represented by Ar ６－２０ A divalent group containing an aromatic hydrocarbon group, A １０ C represented by ６－２０ A divalent group containing an aromatic hydrocarbon group, Ar １１ C represented by ６－１０ Aromatic hydrocarbon groups and Ar １２ C represented by ６－１０ Substituents that the aromatic hydrocarbon group may have; and R １０ C as a substituent represented by １－１６ The hydroxyalkyl group may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－１０ hydroxyalkyl groups, more preferably straight or branched C １－５ hydroxyalkyl groups, and in one embodiment, straight or branched C １－４Hydroxyalkyl groups, specifically, —CH ２ —OH, —CH ２ CH ２ —OH, —CH ２ CH ２ CH ２ —OH, —CH ２ CH(OH)CH ２ CH ３ , -CH ２ CH ２ CH ２ CH ２ It can be —OH.

[0110] C as the above substituent ６－２０ The aromatic hydrocarbon group may be monocyclic or polycyclic. ６－２０ When the aromatic hydrocarbon group is polycyclic, two or more rings may or may not form a condensed ring. ６－２０ The aromatic hydrocarbon group is preferably C ６－１０ It is an aromatic hydrocarbon group, and more preferably, it may be a phenyl group, a tolyl group, a xylyl group, or a naphthyl group.

[0111] an aliphatic or aromatic imido-diyl group represented by A and A １０ C represented by ６－２０ a substituent that the divalent group containing an aromatic hydrocarbon group may have; and R １０ Examples of the substituent represented by the formula: １－１６ Alkyl group; C １－１６ Fluoroalkyl group; C １－１６ an alkoxy group; and a fluorine atom; １－５ Alkyl group; C １－５ More preferred is at least one selected from a fluoroalkyl group and a fluorine atom.

[0112] C represented by Ar ６－２０ A divalent group containing an aromatic hydrocarbon group, Ar １１ C represented by ６－１０ Aromatic hydrocarbon groups and Ar １２ C represented by ６－１０ The substituents that the aromatic hydrocarbon group may have include C １－２０ Fluorine-containing organic group or C ２－２０Fluorine-containing organic group; C １－１６ Alkoxy group; C １－１６ Preferably, the group is at least one selected from a hydroxyalkyl group, a hydroxyl group, a carboxyl group, a glycidyl group, and a fluorine atom.

[0113] R １ C represented by １－１６ an alkylene group, and R １ C represented by ３－１６ The substituent that the divalent group containing an alicyclic hydrocarbon group may have is a C ６－２０ Preferably, the group is at least one selected from an aromatic hydrocarbon group, a hydroxyl group, and a fluorine atom.

[0114] R ２ C represented by １－１６ The substituent that the alkyl group may have is preferably a fluorine atom.

[0115] Each occurrence of k independently represents an integer of 0 to 4, preferably an integer of 0 to 1. Each occurrence of l independently represents an integer of 1 to 4, preferably an integer of 1 to 3. Each occurrence of m independently represents an integer of 0 to 4, preferably an integer of 0 to 3.

[0116] The fluorine-containing aromatic polymer represented by formula (I) is a polymer having the following (i) and (ii): (i) k is 0, and one or more C ２－２０ (ii) k is 1 or more and 4 or less, and one or more C １－２０ and (ii) having a fluorine-containing organic group. However, in the case of (i) above, the fluorine-containing aromatic polymer is １ Fluorine-containing organic groups, especially —CF ３ may have

[0117] The fluorine-containing aromatic polymer of the present disclosure is ２－２０ Fluorine-containing organic group or C １－２０The presence of a fluorine-containing organic group directly bonded to an aromatic ring can impart the properties of the fluorine-containing organic group, and it is expected that the heat resistance of an aromatic polymer can be further improved or maintained at a high level, while the polymer will have excellent properties in various aspects, such as flexibility, stain resistance, friction characteristics, stain resistance, water and oil repellency, low adhesion, stain resistance, solvent solubility, and high surface hardness.

[0118] In the fluorine-containing aromatic polymer of the present disclosure, the number of fluorine-containing organic groups contained in the unit enclosed in parentheses with n attached thereto may be preferably 1 or more, more preferably 1 to 6, and even more preferably 1 to 4 per unit. ２－２０ The number of fluorine-containing organic groups per unit is preferably 1 or more, more preferably 1 to 2. １ Fluorine-containing organic groups (especially -CF ３ The number of ) per unit may be preferably 2 to 6, more preferably 2 to 4, and even more preferably 3 to 4.

[0119] That is, a fluorine-containing organic group can be introduced into an aromatic polymer via a hydrocarbon group, an oxygen atom, etc., but bonds via a hydrocarbon group, an oxygen atom, etc. are vulnerable to heat, light, acid, base, etc., and the introduced fluorine-containing organic group can easily be eliminated. In the fluorine-containing aromatic polymer of the present disclosure, the fluorine-containing organic group is directly bonded to an aromatic ring, making it difficult for the fluorine-containing organic group to be eliminated, and it is thought that the polymer can simultaneously achieve high levels of heat resistance, flexibility, stain resistance, friction properties, and water and oil repellency.

[0120] n represents an integer of 1 or more, and may be preferably 3 or more and 2,000 or less, more preferably 5 or more and 1,000 or less, and even more preferably 10 or more and 1,000 or less.

[0121] The number average molecular weight of the fluorine-containing aromatic polymer represented by formula (I) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0122] In the present disclosure, the number average molecular weight can be measured by gel permeation chromatography, and the converted value using polystyrene as a standard sample can be used as the number average molecular weight.

[0123] The above formula (I) is preferably the following formula (I-a): [In formula (I-a), A ａ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ａ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, na represents an integer of 1 or more, and １－２０ It has a fluorine-containing organic group.

[0124] The fluorine-containing aromatic polymer represented by formula (I-a) contains an imide-N-yl group in the repeating unit and may be a polyimide, polyetherimide or polyamideimide, and is expected to have various excellent properties such as flexibility, adhesion (reactivity) and affinity with other materials, low dielectric properties, transparency, water and oil repellency, low tack, antifouling properties, solvent solubility and high surface hardness while maintaining the properties of these resins.

[0125] A ａ represents, independently in each occurrence, an aliphatic or aromatic imido-diyl group, and examples of such aliphatic or aromatic imido-diyl groups include the same groups as the aliphatic or aromatic imido-diyl groups represented by A.

[0126] A ａ As the group represented by the formula (A1), an aliphatic or aromatic imido-diyl group containing one or more imide rings and optionally having one or more substituents is preferable, a group represented by the formula (A1) is more preferable, a group represented by the formula (A2) is even more preferable, and a group represented by the formulas (A1-1) to (A1-19) is even more preferable.

[0127] Ar ａ each occurrence independently represents a C which may have one or more substituents ６－２０represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0128] Ar ａ is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0129] Above C １－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from the above formula (2A) and formula (2B), and is preferably a group represented by the above formula (2A).

[0130] na represents an integer of 1 or more, and may be preferably 3 or more and 2,000 or less, more preferably 5 or more and 1,000 or less, and even more preferably 10 or more and 1,000 or less.

[0131] The number average molecular weight of the fluorine-containing aromatic polymer represented by formula (Ia) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0132] The above formula (I) is preferably the following formula (I-b): [In formula (I-b), Ar ｂ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｂ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, １ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents an optionally substituted C １－１６ represents an alkyl group or a hydrogen atom, nb represents an integer of 1 or more, and ２－２０ It has a fluorine-containing organic group.

[0133] The fluorine-containing aromatic polymer represented by formula (I-b) may be, for example, polycarbonate, polyphenylene sulfide, polyphenylene ether, etc., and is expected to have various excellent properties such as flexibility, adhesion (reactivity) and affinity with other materials, low dielectric properties, transparency, water and oil repellency, low tack, antifouling properties, solvent solubility, and high surface hardness while maintaining the properties of these resins.

[0134] Ar ｂ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0135] Ar ｂ is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0136] L ｂ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -. １ and R ２ has the same meaning as above. ｂ As the alkyl group, —O—CO—O—, —S—, and —O— are preferred.

[0137] Above C ２－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from the above formula (1A) and the above formula (1B), and more preferably a group represented by the above formula (1A).

[0138] nb represents an integer of 1 or more, and may be preferably 3 or more and 2,000 or less, more preferably 5 or more and 1,000 or less, and even more preferably 10 or more and 1,000 or less.

[0139] The number average molecular weight of the fluorine-containing aromatic polymer represented by formula (Ib) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0140] The above formula (I-b) is preferably the following formula (I-b1), (I-b2), (I-b3), (I-b4), (I-b5), (I-b6) or (I-b7): [In formula (I-b1), (I-b2), (I-b3), (I-b4), (I-b5), (I-b6) or (I-b7), Ar ｂ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, nb represents an integer of 1 or more, and in formula (I-b1), (I-b2), (I-b3), (I-b4), (I-b5), (I-b6) or (I-b7), each of them contains one or more C２－２０ It has a fluorine-containing organic group.

[0141] Above C ２－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more groups selected from the above formula (1A) and formula (1B), and more preferably a group represented by the above formula (1A).

[0142] The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-b1) may be preferably 1,000 to 1,000,000, more preferably 2,000 to 500,000, and even more preferably 2,000 to 200,000. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-b2) may be preferably 1,000 to 1,000,000, more preferably 2,000 to 500,000, and even more preferably 2,000 to 200,000. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-b3) may be preferably 1,000 to 1,000,000, more preferably 2,000 to 500,000, and even more preferably 2,000 to 200,000. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-b4) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-b5) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-b6) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-b7) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0143] The above formula (I) is preferably the following formula (I-c): [In formula (I-c), Ar ｃ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｃ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｃ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, ｃ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of Ar ｃ１ and Ar ｃ２ and L ｃ１ and L ｃ２ In at least one combination of R １ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents an optionally substituted C １－１６ represents an alkyl group or a hydrogen atom, nc represents an integer of 1 or more, and ２－２０ It has a fluorine-containing organic group.]

[0144] The fluorine-containing aromatic polymer represented by formula (I-c) may be, for example, polysulfone, polyamide, etc., and is expected to have various excellent properties such as flexibility, adhesion (reactivity) and affinity with other materials, low dielectric properties, transparency, water and oil repellency, low tack, antifouling properties, solvent solubility, and high surface hardness while maintaining the properties of these resins.

[0145] Ar ｃ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0146] Ar ｃ１ is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0147] Ar ｃ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0148] Ar ｃ２is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0149] L ｃ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -. １ and R ２ has the same meaning as above. ｃ１ As the ２ -, -NR ２ -CO- is preferred.

[0150] L ｃ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -. １ and R ２ has the same meaning as above. ｃ２ Examples of the group include —O—, —CO—NR ２ - is preferred.

[0151] Above C ２－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from the above formula (1A) and formula (1B), and more preferably a group represented by the above formula (1A).

[0152] In formula (I-c), Arｃ１ and Ar ｃ２ and L ｃ１ and L ｃ２ In at least one combination of L ｃ１ and L ｃ２ In the combination of one group is a different group from the other group.

[0153] nc represents an integer of 1 or more, and may be preferably 3 or more and 2,000 or less, more preferably 5 or more and 1,000 or less, and even more preferably 10 or more and 1,000 or less.

[0154] The number average molecular weight of the fluorine-containing aromatic polymer represented by formula (Ic) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0155] The above formula (I-c) is preferably the following formula (I-c1), (I-c2) or (I-c3): [In formula (I-c1), (I-c2) or (I-c3), Ar ｃ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｃ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, each occurrence of nc independently represents an integer of 1 or more, and in formula (I-c1), (I-c2) or (I-c3), each of C ２－２０ It has a fluorine-containing organic group.

[0156] The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-c1) may be preferably 1,000 to 1,000,000, more preferably 2,000 to 500,000, and even more preferably 2,000 to 200,000. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-c2) may be preferably 1,000 to 1,000,000, more preferably 2,000 to 500,000, and even more preferably 2,000 to 200,000. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-c3) may be preferably 1,000 to 1,000,000, more preferably 2,000 to 500,000, and even more preferably 2,000 to 200,000.

[0157] The above (I) is preferably represented by the following formula (I-d): [In formula (I-d), Ar ｄ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｄ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｄ３ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｄ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, ｄ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２—CO— and CO—NR ２ represents one selected from the group consisting of -, ｄ３ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of Ar ｄ１ , Ar ｄ２ and Ar ｄ３ A combination of, and L ｄ１ , L ｄ２ and L ｄ３ In at least one combination of the above, one group is a group different from at least one of the other two groups, and R １ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents an optionally substituted C １－１６ represents an alkyl group or a hydrogen atom, nd represents an integer of 1 or more, and ２－２０ It has a fluorine-containing organic group.

[0158] The fluorine-containing aromatic polymer represented by formula (I-d) may be, for example, polyether ether ketone, polyethersulfone, etc., and is expected to have various excellent properties such as flexibility, adhesion (reactivity) and affinity with other materials, low dielectric properties, transparency, water and oil repellency, low tack, antifouling properties, solvent solubility, and high surface hardness while maintaining the properties of these resins.

[0159] Ar ｄ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0160] Ar ｄ１ is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0161] Ar ｄ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0162] Ar ｄ２ is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0163] Ar ｄ３ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0164] Ar ｄ３is preferably a group represented by formula (Ar1), and more preferably one selected from a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group.

[0165] L ｄ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -. １ and R ２ has the same meaning as above. ｄ１ Examples include -CO-, -SO ２ - is preferably one selected from the group consisting of

[0166] L ｄ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -. １ and R ２ has the same meaning as above. ｄ２ As the group, —O— is preferred.

[0167] L ｄ３ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -. １ and R２ has the same meaning as above. ｄ３ As the group, —O— is preferred.

[0168] Above C ２－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from the above formula (1A) and formula (1B), and more preferably a group represented by the above formula (1A).

[0169] In formula (I-d), Ar ｄ１ , Ar ｄ２ and Ar ｄ３ and L ｄ１ , L ｄ２ and L ｄ３ In at least one combination of the above, one group is a group different from at least one of the other two groups, and preferably, L ｃ１ , L ｃ２ and L ｃ３ In the combination of one group is a group that is different from at least one of the other two groups.

[0170] nd represents an integer of 1 or more, and may be preferably 3 or more and 2,000 or less, more preferably 5 or more and 1,000 or less, and even more preferably 10 or more and 1,000 or less.

[0171] The number average molecular weight of the fluorine-containing aromatic polymer represented by formula (Id) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0172] The above formula (I-d) is preferably the following formula (I-d1) or (I-d2): [In formula (I-d1) or (I-d2), Ar ｄ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｄ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group,ｄ３ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, nd independently represents an integer of 1 or more in each occurrence, and in formulas (I-d1) and (I-d2), each of them contains one or more C ２－２０ It has a fluorine-containing organic group.

[0173] The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-d1) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-d2) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0174] The above (I) is preferably represented by the following formula (I-e): [In formula (I-e), Ar ｅ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｅ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, ｅ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, ｅ３ is independently at each occurrence -R１ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, １ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents an optionally substituted C １－１６ represents an alkyl group or a hydrogen atom, ne represents an integer of 1 or more, and ２－２０ It has a fluorine-containing organic group.

[0175] The fluorine-containing aromatic polymer represented by formula (I-e) may be a polyether, polyester, or polyamide, and is expected to have various excellent properties such as flexibility, adhesion (reactivity) and affinity with other materials, low dielectric properties, transparency, water and oil repellency, low tack, antifouling properties, solvent solubility, and high surface hardness while maintaining the properties of these resins.

[0176] Ar ｅ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0177] Ar ｅ１is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0178] L ｅ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -. １ and R ２ has the same meaning as above. ｅ１ is preferably one selected from the group consisting of —CO—O—, —O— and CO—NH—.

[0179] L ｅ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -. １ and R ２ has the same meaning as above. ｅ２ As for -R １ - is preferred.

[0180] L ｅ３ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２represents one selected from the group consisting of -. １ and R ２ has the same meaning as above. ｅ３ is preferably one selected from the group consisting of —O—CO—, —O— and NH—CO—.

[0181] Above C ２－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from the above formula (1A) and formula (1B), and more preferably a group represented by the above formula (1A).

[0182] ne represents an integer of 1 or more, and may be preferably 3 or more and 2,000 or less, more preferably 5 or more and 1,000 or less, and even more preferably 10 or more and 1,000 or less.

[0183] The number average molecular weight of the fluorine-containing aromatic polymer represented by formula (Ie) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0184] The above formula (I-e) is preferably the following formula (I-e1), (I-e2) or (I-e3): [wherein in formula (I-e1), (I-e2) or (I-e3), Ar ｅ１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, R ７ is a C which may have one or more substituents １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ each occurrence of ne independently represents an integer of 1 or more; and in formula (I-e1), (I-e2) or (I-e3), each of C ２－２０ It has a fluorine-containing organic group.

[0185] The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-e1) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-e2) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-e3) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0186] The formula (I) is preferably the following formula (I-g): [In formula (Ig), Ar ｇ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, mg each independently represents an integer of 1 or more and 4 or less in each occurrence, ng1 represents an integer of 1 or more, ng2 represents an integer of 1 or more, and ２－２０ It has a fluorine-containing organic group.

[0187] The fluorine-containing aromatic polymer represented by formula (I-g) may be a copolymer of an aromatic polymer and a polymer containing an aliphatic or alicyclic group, and is expected to have various excellent properties such as flexibility, adhesion (reactivity) and affinity with other materials, low dielectric properties, transparency, water and oil repellency, low tack, antifouling properties, solvent solubility, and high surface hardness while maintaining the properties of these resins.

[0188] Ar ｇ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0189] Ar ｇ is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0190] L ｇ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -. １ and R ２ has the same meaning as above. ｇ１ As for -R １ - is preferred, and C optionally having one or more substituents is preferred. ３－１６ C is more preferably a divalent group containing an alicyclic hydrocarbon group, and may have one or more substituents. ３－１６ An alicyclic hydrocarbon group is more preferred.

[0191] mg represents an integer of 1 or more and 4 or less, and is preferably 1.

[0192] Above C ２－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from the above formula (1A) and formula (1B), and more preferably a group represented by the above formula (1A).

[0193] In the fluorine-containing aromatic polymer represented by formula (I-g), the order in which the unit enclosed in parentheses with ng1 and the unit enclosed in parentheses with ng2 are present is not particularly limited. The fluorine-containing aromatic polymer represented by formula (I-g) may be a random copolymer in which the unit enclosed in parentheses with ng1 and the unit enclosed in parentheses with ng2 are randomly arranged, or may be a block copolymer containing a block consisting of units enclosed in parentheses with ng1 and a block consisting of units enclosed in parentheses with ng2.

[0194] The above (I) is preferably represented by the following formula (Ih): [In formula (Ih), A ｈ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ｈ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ｈ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, １ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, nh represents an integer of 1 or more, and １－２０ It has a fluorine-containing organic group.

[0195] The fluorine-containing aromatic polymer represented by formula (I-h) may be a polyamideimide containing an imide-N-yl group as a repeating unit, and is expected to have various excellent properties such as flexibility, adhesion (reactivity) and affinity with other materials, low dielectric properties, transparency, water and oil repellency, low tack, antifouling properties, solvent solubility, and high surface hardness while maintaining the properties of these resins.

[0196] A ｈ represents, independently in each occurrence, an aliphatic or aromatic imido-diyl group, and examples of such aliphatic or aromatic imido-diyl groups include the same groups as the aliphatic or aromatic imido-diyl groups represented by A.

[0197] A ｈ As the alkyl group, an aliphatic or aromatic imido-diyl group containing one or more imide rings and optionally having one or more substituents is preferable, a group represented by formula (A1-II) is more preferable, and a group represented by formula (A2-II) is even more preferable.

[0198] Ar ｈ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0199] Ar ｈ is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a hydroxyphenylene group, a hydroxyxylylene group, a naphthylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0200] L ｈ is independently at each occurrence -R １ -, -O-, -S-, -NR ２-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -. １ and R ２ has the same meaning as above. ｈ As the alkyl group, —NH—CO— is preferred.

[0201] Above C １－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from the group consisting of formula (2A) and formula (2B), and more preferably a group represented by formula (2A).

[0202] nh represents an integer of 1 or more, and may be preferably 3 or more and 2,000 or less, more preferably 5 or more and 1,000 or less, and even more preferably 10 or more and 1,000 or less.

[0203] The number average molecular weight of the fluorine-containing aromatic polymer represented by formula (Ih) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0204] The above formula (Ih) is preferably the following formula (I-h1): [In formula (I-h1), A ｈ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ｈ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, each occurrence of nh independently represents an integer of 1 or more, and in formula (I-h1), each occurrence of nh independently represents an integer of 1 or more. １－２０ It has a fluorine-containing organic group.

[0205] The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-h1) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0206] (Method for producing fluorine-containing aromatic polymer) The fluorine-containing aromatic polymer of the present disclosure can be produced by a production method comprising introducing a fluorine-containing organic group into an aromatic polymer to obtain a fluorine-containing aromatic polymer (Production method 1). Alternatively, the fluorine-containing aromatic polymer of the present disclosure can be produced by a production method comprising introducing a fluorine-containing group into an aromatic monomer to obtain a fluorine-containing aromatic monomer, and using the fluorine-containing aromatic monomer as a monomer to obtain a fluorine-containing aromatic polymer (Production method 2).

[0207] In the production method of the present disclosure, a compound represented by formula (II) described below is used as a compound for introducing a fluorine-containing organic group, and a variety of fluorine-containing organic groups can be introduced. Furthermore, in the production method of the present disclosure, by using such a compound represented by formula (II), a fluorine-containing organic group can be introduced into both a monomer and a polymer, and the distribution of the fluorine-containing organic group in the fluorine-containing aromatic polymer can also be controlled.

[0208] (Production Method 1) That is, the present disclosure provides a compound represented by the following formula (I-1): [In formula (I-1), A １ each occurrence independently represents a divalent organic group containing one or more imide rings and optionally having one or more substituents; １ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, １ is independently at each occurrence -R １１ -, -O-, -S-, -NR １２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR １２ —CO— and CO—NR １２represents one selected from the group consisting of -, １１ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, １２ each occurrence independently represents an optionally substituted C １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, k1 each independently represents an integer of 0 to 4 in each occurrence, l1 each independently represents an integer of 1 to 4 in each occurrence, m1 each independently represents an integer of 0 to 4 in each occurrence, n1 represents an integer of 1 or more, in the unit enclosed in parentheses with n1, the units enclosed in parentheses with k1, l1, and m1 may appear in any order, and in formula (I-1), one or more C １－２０ It has a fluorine-containing organic group.]

[0209] A method for producing a fluorinated aromatic polymer represented by the following formula (I-2): [In formula (I-2), A ２ each occurrence independently represents a divalent organic group containing one or more imide rings and optionally having one or more substituents; ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２ —CO— and CO—NR ２ represents one selected from the group consisting of -, １ each occurrence independently represents an optionally substituted C １－１６an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ２ each occurrence independently represents an optionally substituted C １－１６ represents an alkyl group or a hydrogen atom, k2, in each occurrence, independently represents an integer of 0 to 4, l2, in each occurrence, independently represents an integer of 1 to 4, m2, in each occurrence, independently represents an integer of 0 to 4, n2, in each occurrence, independently represents an integer of 1 or more, and n represents an integer of 1 or more, and in the unit enclosed in parentheses with n, the units enclosed in parentheses with k2, l2, and m2 may appear in any order.] and an aromatic polymer represented by the following formula (II): I-R ｆ１ (II) [In formula (II), R ｆ１ is C １－２０ represents a fluorine-containing organic group.] (hereinafter also referred to as "fluorine-containing organic group introduction reaction" into the aromatic polymer) is also included (Production Method 1).

[0210] According to the above-mentioned production method 1, since the fluorine-containing organic groups are introduced after the production of an aromatic polymer, it is possible to easily select the polymer structure and number-average molecular weight from a wide range. Furthermore, for the same reason, widely available aromatic polymers can be used as raw materials, making it possible to easily produce fluorine-containing aromatic polymers. Furthermore, the raw material aromatic polymer is not limited to powder or pellet-like non-molded bodies, and easily available molded products such as plates, films, and various parts can also be used. In this case, it is possible to introduce fluorine-containing organic groups only onto the surface of the molded product without changing its shape. Furthermore, this production method tends to easily introduce fluorine-containing organic groups into multiple positions on the aromatic ring, and polymers with a composition similar to that of a random copolymer can be produced in terms of their structure. Such random copolymer-like polymers, due to their low order, are an effective molecular design for exhibiting flexibility, represented by a low Tg and a high thermal expansion coefficient (CTE). Furthermore, in general, a substituent effect is observed when introducing fluorine-containing organic groups into such aromatic rings, and electron-withdrawing substituents deactivate the aromatic ring. However, according to the above-mentioned production method 1, a fluorine-containing organic group can be effectively introduced even into an inactive aromatic ring having an electron-withdrawing substituent.

[0211] A １ represents, independently in each occurrence, an aliphatic or aromatic imido-diyl group, and examples of such aliphatic or aromatic imido-diyl groups include the same groups as the aliphatic or aromatic imido-diyl groups represented by A.

[0212] A １ As the group represented by the formula (A1), an aliphatic or aromatic imido-diyl group containing one or more imide rings and optionally having one or more substituents is preferable, a group represented by the formula (A1) is more preferable, a group represented by the formula (A2) is even more preferable, and a group represented by the formulas (A1-1) to (A1-19) is even more preferable.

[0213] A １ The aliphatic or aromatic imido-diyl group represented by the formula (I) may have a substituent. Examples of such a substituent include C １－２０ Fluorine-containing organic group; C １－１６Alkyl group; C １－１６ an alkoxy group; and a fluorine atom; １－１６ Alkyl group; C １－１６ and a fluorine atom. １－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from the above formula (2A) and formula (2B), and more preferably a group represented by the above formula (2-a), formula (2-b), formula (2-c), or formula (2B). １－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by the above formula (2A), and more preferably a group represented by the above formula (2-a), formula (2-b), or formula (2-c).

[0214] A ２ represents, independently in each occurrence, an aliphatic or aromatic imido-diyl group, and examples of such aliphatic or aromatic imido-diyl groups include the same groups as the aliphatic or aromatic imido-diyl groups represented by A.

[0215] A ２ As the group represented by the formula (A1), an aliphatic or aromatic imido-diyl group containing one or more imide rings and optionally having one or more substituents is preferable, a group represented by the formula (A1) is more preferable, a group represented by the formula (A2) is even more preferable, and a group represented by the formulas (A1-1) to (A1-19) is even more preferable.

[0216] A ２ The aliphatic or aromatic imido-diyl group represented by the formula (I) may have a substituent. Examples of such a substituent include C １－１６ Alkyl group; C １－１６ alkoxy groups; and fluorine atoms.

[0217] Ar １ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0218] Ar １ is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0219] Ar １ C represented by ６－２０ The divalent group containing an aromatic hydrocarbon group may have a substituent. Such a substituent includes C represented by Ar. ６－２０ The substituents may be the same as those that may be contained in the divalent group containing an aromatic hydrocarbon group. １－２０ Fluorine-containing organic group; C １－１６ Alkyl group; C １－１６ an alkoxy group; and a fluorine atom; １－２０ Fluorine-containing organic group; C １－１６ An alkoxy group; and a fluorine atom are preferred. ６－２０ The two or more substituents that the aromatic hydrocarbon group may have may be bonded to each other to form the above C ６－２０ They may be combined with the aromatic hydrocarbon group to form a ring.

[0220] Ar ２ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, and such a group is a C ６－２０ Examples include the same groups as the divalent groups containing aromatic hydrocarbon groups.

[0221] Ar ２is preferably a group represented by formula (Ar1), more preferably one selected from a phenylene group, a xylylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and still more preferably a phenylene group.

[0222] Ar ２ C represented by ６－２０ The divalent group containing an aromatic hydrocarbon group may have a substituent. Such a substituent includes C represented by Ar. ６－２０ Examples of the substituent include the same groups as those that may be possessed by the divalent group containing an aromatic hydrocarbon group, and C １－１６ Alkyl group; C １－１６ an alkoxy group; and a fluorine atom; １－１６ An alkoxy group; and a fluorine atom are preferred. ６－２０ The two or more substituents that the divalent group containing an aromatic hydrocarbon group may have are bonded to each other to form the above C ６－２０ They may be combined with the aromatic hydrocarbon group to form a ring.

[0223] L １ is independently at each occurrence -R １１ -, -O-, -S-, -NR １２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR １２ —CO— and CO—NR １２ - represents one kind selected from the group consisting of

[0224] R １１ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group.

[0225] C which may have one or more of the above-mentioned substituents １－１６ "C" in the alkylene group １－１６The "alkylene group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－１０ alkylene groups, more preferably straight or branched C １－５ In one embodiment, the C １－３ Alkylene groups, specifically, —CH ２ -, -CH ２ CH ２ -, -CH ２ CH ２ CH ２ -It can be.

[0226] In one embodiment, the R １１ is a C having no substituents １－１６ In another embodiment, the R １１ is a C having a substituent １－１６ It may be an alkylene group.

[0227] C which may have one or more of the above-mentioned substituents １－１６ The alkylene group may be substituted with one or more fluorine atoms. １１ is preferably a C substituted by one or more fluorine atoms １－１６ is a fluoroalkylene group, more preferably C １－１６ A perfluoroalkylene group, more preferably C １－６ perfluoroalkylene groups, more preferably C １－３ It is a perfluoroalkylene group.

[0228] Above C １－１６ The perfluoroalkylene group may be a straight chain or a branched chain, and preferably is a straight chain or branched chain C １－６ perfluoroalkylene groups, more preferably straight-chain or branched C １－３ Perfluoroalkylene groups, specifically, —CF ２ -, -CF ２ CF ２ -, CF ２ CF ２ CF ２ -, CF ２ CF (CF３ )-.

[0229] R １１ C represented by １－１６ Other substituents that the alkylene group may have include C １－２０ Fluorine-containing organic groups are exemplified. １－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from formula (2A) and formula (2B), and more preferably a group represented by formula (2A).

[0230] C which may have one or more of the above-mentioned substituents ３－１６ "C" in a divalent group containing an alicyclic hydrocarbon group ３－１６ The "alicyclic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic group, two or more rings may or may not form bridged rings. ３－１６ In the divalent group containing an alicyclic hydrocarbon group, the number of alicyclic hydrocarbon groups is 1 or more, preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. Such a divalent group containing an alicyclic hydrocarbon group, preferably a divalent C ３－１６ is an alicyclic hydrocarbon group, more preferably a divalent C ６－１２ Alicyclic hydrocarbon groups are more preferably cyclohexanediyl groups, decahydronaphthyl groups, isobornyl groups, tricyclo[5.2.1.0] groups, 2,6 ] may be a decanediyl group or an adamantyl group.

[0231] C which may have one or more of the above-mentioned substituents ３－１６ In a divalent group containing an alicyclic hydrocarbon group, two or more alicyclic hydrocarbon groups may be bonded via a single bond or a divalent organic group. Such an organic group may be a linear or branched C １－４ Examples of suitable alkyl groups include:

[0232] R １１In one embodiment, the divalent alicyclic hydrocarbon group represented by R is a divalent alicyclic hydrocarbon group having a substituent, and in another embodiment, it is a divalent alicyclic hydrocarbon group having no substituent. １１ C represented by ３－１６ The substituent that the divalent group containing an alicyclic hydrocarbon group may have is, for example, C １－２０ Examples include a fluorine-containing organic group and a fluorine atom, and a fluorine atom is preferred. １－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from formula (2A) and formula (2B), and more preferably a group represented by formula (2A).

[0233] In one embodiment, R １１ Divalent C represented by ３－１６ The alicyclic hydrocarbon group is preferably a divalent C ３－１６ An alicyclic hydrocarbon group, more preferably a divalent C ６－１２ It may be an alicyclic hydrocarbon group.

[0234] In one embodiment, the R １１ is a C having no substituents １－１６ In another embodiment, the R １１ is a C having a substituent １－１６ In yet another embodiment, the R １１ is a divalent C having no substituents １－１６ It may be an alicyclic hydrocarbon group.

[0235] R １２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom.

[0236] C which may have one or more of the above-mentioned substituents １－１６ "C" in the 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 １－１０alkyl group, more preferably a straight or branched C １－５ is an alkyl group, and in one embodiment is a straight or branched C １－４ It is an alkyl group, specifically, —CH ３ , -CH ２ CH ３ , -CH ２ CH ２ CH ３ , -CH(CH ３ ) ２ , -CH ２ CH ２ CH ２ CH ３ , -CH ２ CH (CH ３ ) ２ , -CH(CH ３ ) ３ It could be.

[0237] In one embodiment, the R １２ is a C having no substituents １－１６ In another embodiment, the R １２ is a C having a substituent １－１６ It may be an alkyl group.

[0238] C which may have one or more of the above-mentioned substituents １－１６ The alkyl group may be substituted with one or more fluorine atoms. １２ is preferably a C substituted by one or more fluorine atoms １－１６ fluoroalkyl group, more preferably C １－１６ is a perfluoroalkyl group, more preferably C １－６ perfluoroalkyl groups, more preferably C １－４ A perfluoroalkyl group, specifically, —CF ３ , -CF ２ CF ３ , -CF ２ CF ２ CF ３ , -CF(CF ３ ) ２ , -CF ２ CF ２ CF ２ CF３ , -CF ２ CF (CF ３ ) ２ , -CF(CF ３ ) ３ It could be.

[0239] C which may have one or more of the above-mentioned substituents ６－２０ "C" in the aromatic hydrocarbon group ６－２０ The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic ring, two or more rings may or may not form a condensed ring. ６－２０ The aromatic hydrocarbon group is preferably C ６－１０ It is an aromatic hydrocarbon group, more preferably a phenylene group, a tolylene group, a xylylene group, or a naphthylene group, and in one embodiment, it is more preferably a phenylene group, a tolylene group, or a xylylene group, and in another embodiment, it may be more preferably a naphthylene group.

[0240] Above C ６－２０ The substituent that the aromatic hydrocarbon group may have includes a hydroxyl group.

[0241] L １ is preferably —O—, —S—, —CO—, —O—CO—O—, or —SO ２ -, -NR １２ —CO— and CO—NR １２ - is one selected from the group consisting of

[0242] L ２ is independently at each occurrence -R ２１ -, -O-, -S-, -NR ２２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR ２２ —CO— and CO—NR ２２ - represents one kind selected from the group consisting of

[0243] R ２１ each occurrence independently represents an optionally substituted C １－１６an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group.

[0244] C which may have one or more of the above-mentioned substituents １－１６ "C" in the alkylene group １－１６ The "alkylene group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－１０ alkylene groups, more preferably straight or branched C １－５ In one embodiment, the C １－３ Alkylene groups, specifically, —CH ２ -, -CH ２ CH ２ -, -CH ２ CH ２ CH ２ -It can be.

[0245] In one embodiment, the R ２１ The alkylene group represented by the formula １－１６ In another embodiment, the R ２１ The alkylene group represented by the formula １－１６ It may be an alkylene group.

[0246] C which may have one or more of the above-mentioned substituents １－１６ The alkylene group may be substituted with one or more fluorine atoms. １１ is preferably a C substituted by one or more fluorine atoms １－１６ is a fluoroalkylene group, more preferably C １－１６ A perfluoroalkylene group, more preferably C １－６ perfluoroalkylene groups, more preferably C １－３ It is a perfluoroalkylene group.

[0247] Above C １－１６ The perfluoroalkylene group may be a straight chain or a branched chain, and preferably is a straight chain or branched chain C １－６perfluoroalkylene groups, more preferably straight-chain or branched C １－３ Perfluoroalkylene groups, specifically, —CF ２ -, -CF ２ CF ２ -, CF ２ CF ２ CF ２ -, CF ２ CF (CF ３ )-.

[0248] R ２１ C represented by １－１６ Other substituents that the alkylene group may have include C １－２０ Fluorine-containing organic groups are exemplified. １－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from formula (2A) and formula (2B), and more preferably a group represented by formula (2A).

[0249] C which may have one or more of the above-mentioned substituents ３－１６ "C" in a divalent group containing an alicyclic hydrocarbon group ３－１６ The "alicyclic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic group, two or more rings may or may not form bridged rings. ３－１６ In the divalent group containing an alicyclic hydrocarbon group, the number of alicyclic hydrocarbon groups is 1 or more, preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. Such a divalent group containing an alicyclic hydrocarbon group, preferably a divalent C ３－１６ is an alicyclic hydrocarbon group, more preferably a divalent C ６－１２ Alicyclic hydrocarbon groups are more preferably cyclohexanediyl groups, decahydronaphthyl groups, isobornyl groups, tricyclo[5.2.1.0] groups, 2,6 ] may be a decanediyl group or an adamantyl group.

[0250] C which may have one or more of the above-mentioned substituents ３－１６In a divalent group containing an alicyclic hydrocarbon group, two or more alicyclic hydrocarbon groups may be bonded via a single bond or a divalent organic group. Such an organic group may be a linear or branched C １－４ Examples of suitable alkyl groups include:

[0251] R ２１ In one embodiment, the divalent alicyclic hydrocarbon group represented by R is a divalent alicyclic hydrocarbon group having a substituent, and in another embodiment, it is a divalent alicyclic hydrocarbon group having no substituent. １１ C represented by ３－１６ The substituent that the divalent group containing an alicyclic hydrocarbon group may have is, for example, C １－２０ Examples include a fluorine-containing organic group and a fluorine atom, and a fluorine atom is preferred. １－２０ The fluorine-containing organic group is an organic group containing a fluorine atom, and is preferably a group represented by one or more selected from formula (2A) and formula (2B), and more preferably a group represented by formula (2A).

[0252] In one embodiment, R ２１ Divalent C represented by ３－１６ The alicyclic hydrocarbon group is preferably a divalent C ３－１６ An alicyclic hydrocarbon group, more preferably a divalent C ６－１２ It may be an alicyclic hydrocarbon group.

[0253] In one embodiment, the R ２１ is a C having no substituents １－１６ In another embodiment, the R ２１ is a C having a substituent １－１６ In yet another embodiment, the R ２１ is a divalent C having no substituents １－１６ It may be an alicyclic hydrocarbon group.

[0254] R ２２ each occurrence independently represents a C which may have one or more substituents １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom.

[0255] C which may have one or more of the above-mentioned substituents １－１６ "C" in the 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 １－１０ alkyl group, more preferably a straight or branched C １－５ is an alkyl group, and in one embodiment is a straight or branched C １－４ It is an alkyl group, specifically, —CH ３ , -CH ２ CH ３ , -CH ２ CH ２ CH ３ , -CH(CH ３ ) ２ , -CH ２ CH ２ CH ２ CH ３ , -CH ２ CH (CH ３ ) ２ , -CH(CH ３ ) ３ It could be.

[0256] In one embodiment, the R ２２ is a C having no substituents １－１６ In another embodiment, the R ２２ is a C having a substituent １－１６ It may be an alkyl group.

[0257] C which may have one or more of the above-mentioned substituents １－１６ The alkyl group may be substituted with one or more fluorine atoms. ２２ is preferably a C substituted by one or more fluorine atoms １－１６ fluoroalkyl group, more preferably C １－１６ is a perfluoroalkyl group, more preferably C １－６ perfluoroalkyl groups, more preferably C １－４ A perfluoroalkyl group, specifically, —CF ３ , -CF ２ CF ３, -CF ２ CF ２ CF ３ , -CF(CF ３ ) ２ , -CF ２ CF ２ CF ２ CF ３ , -CF ２ CF (CF ３ ) ２ , -CF(CF ３ ) ３ It could be.

[0258] C which may have one or more of the above-mentioned substituents ６－２０ "C" in the aromatic hydrocarbon group ６－２０ The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic ring, two or more rings may or may not form a condensed ring. ６－２０ The aromatic hydrocarbon group is preferably C ６－１０ It is an aromatic hydrocarbon group, more preferably a phenylene group, a tolylene group, a xylylene group, or a naphthylene group, and in one embodiment, it is more preferably a phenylene group, a tolylene group, or a xylylene group, and in another embodiment, it may be more preferably a naphthylene group.

[0259] Above C ６－２０ The substituent that the aromatic hydrocarbon group may have includes a hydroxyl group.

[0260] L ２ is preferably —O—, —S—, —CO—, —O—CO—O—, or —SO ２ -, -NR ２２ —CO— and CO—NR ２２ - is one selected from the group consisting of

[0261] k1, in each occurrence, independently represents an integer of 0 to 4, preferably an integer of 0 to 1. l1, in each occurrence, independently represents an integer of 1 to 4, preferably an integer of 1 to 3. m1, in each occurrence, independently represents an integer of 0 to 4, preferably an integer of 0 to 3. k2, in each occurrence, independently represents an integer of 0 to 4, preferably an integer of 0 to 1. l2, in each occurrence, independently represents an integer of 1 to 4, preferably an integer of 1 to 3. m2, in each occurrence, independently represents an integer of 0 to 4, preferably an integer of 0 to 3.

[0262] n1 represents an integer of 1 or more, and may be preferably 5 or more and 2,000 or less, and more preferably 10 or more and 1,000 or less. n2 represents an integer of 1 or more, and may be preferably 5 or more and 2,000 or less, and more preferably 10 or more and 1,000 or less.

[0263] The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-1) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less. The number average molecular weight of the fluorinated aromatic polymer represented by formula (I-2) may be preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 500,000 or less, and even more preferably 2,000 or more and 200,000 or less.

[0264] R ｆ１ is C １－２０ It represents a fluorine-containing organic group. １－２０ The fluorine-containing organic group is a C １－２０ It is an organic group, preferably a group represented by one or more selected from formula (2A) and formula (2B), more preferably a group represented by formula (2-a), formula (2-b), formula (2-c) and formula (2B). １－２０ The fluorine-containing organic group is a C １－２０It is an organic group, preferably a group represented by formula (2A), more preferably a group represented by formula (2-a), formula (2-b) or formula (2-c).

[0265] The ratio of the amount of substance of the compound represented by formula (II) to the amount of substance of all aromatic rings contained in the aromatic polymer (the value obtained by dividing the amount of substance of the compound represented by formula (II) by the amount of substance of all aromatic rings) may be preferably 0.01 or more, more preferably 0.02 or more and 10 or less, even more preferably 0.05 or more and 5 or less, and even more preferably 0.05 or more and 3 or less.

[0266] (Production Method 1: Reaction for Introducing Fluorine-Containing Organic Groups into Aromatic Polymer) The above reaction may be carried out under light irradiation. Such light irradiation is preferably ultraviolet light irradiation, and can be carried out by irradiating light having a wavelength of 300 to 400 nm, for example, 350 to 380 nm.

[0267] The light source used for such light irradiation is not particularly limited, but examples include LED, mercury lamp, xenon lamp, UV lamp, halogen lamp, fluorescent lamp, sunlight, and indoor light, and preferably LED is used.

[0268] The above reaction can be preferably carried out using a basic compound, a catalyst, a one-electron reducing agent or a radical generator.

[0269] Examples of the basic compound include Cs ２ CO ３ , K. ２ CO ３ , Na ２ CO ３ , Li ２ CO ３ , CsF, CsHCO ３ , KHCO ３ , NaHCO ３ , LiHCO ３inorganic bases such as triethylamine, tributylamine, diisopropylethylamine, N,N,N',N'-tetramethylenediamine, N,N,N',N'-tetraethylenediamine, pyrrolidine, pyridine, collidine, ammonia, dimethylamine, DBU and other amine compounds; tributylphosphine, triphenylphosphine, triarylphosphines, disubstituted phosphines and the like are exemplified, and preferably Cs ２ CO ３ is used.

[0270] The catalyst includes a transition metal complex, an organic dye compound, and an enamine compound.

[0271] Examples of the central metal species contained in the transition metal complex include cobalt, ruthenium, rhodium, rhenium, iridium, zinc, nickel, palladium, osmium, and platinum.

[0272] Examples of the organic dye compounds include rose bengal, erythrosine, eosin (e.g., eosin B, eosin Y), acriflavine, lipoflavin, thionine, phenoxazine, and phenothiazine.

[0273] The enamine compound The structure is represented by the formula: [In the formula, R ５１ is a phenyl group or a benzyl group, and R ５２ is a hydrogen atom, a methyl group, or a phenyl group.] and pyrrolidines [In the formula, R ５３ is a hydrogen atom or a bis(3,4-dimethoxyphenyl)methoxymethyl group. A pre-synthesized enamine compound may be added, or an aldehyde and a pyrrole may be added directly to generate a catalyst in the reaction system.

[0274] Examples of the aldehydes include 3-phenyl-2-methylpropanal, 2-phenylpropanal, diphenylacetaldehyde, and phenylacetaldehyde.

[0275] Examples of the pyrrolidines include pyrrolidine, (S)-2-[3,4-bis(dimethoxyphenyl)methoxymethyl]pyrrolidine, and the like.

[0276] Examples of the one-electron reducing agent include sodium thiosulfate, lithium dithionite, sodium dithionite, potassium dithionite, cesium dithionite, copper(I) iodide, copper(I) bromide, copper(I) chloride, triethylamine, tributylamine, tetrabutylammonium iodide, tetrabutylphosphonium iodide, ascorbic acid, ascorbate salts, zinc powder, indium powder, and magnesium powder. Preferred are sodium thiosulfate, sodium dithionite, copper(I) iodide, or copper(I) bromide, and particularly preferred are sodium thiosulfate or sodium dithionite.

[0277] Examples of the radical generator include organic peroxides, inorganic peroxides, and organic azo compounds, and organic peroxides are preferred. Examples of the organic peroxide include, but are not limited to, benzoyl peroxide, potassium persulfite, and azobisisobutyronitrile (AIBN).

[0278] The above reaction is preferably carried out in a solvent. Examples of such solvents include, but are not limited to, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, dichloropentafluoropropane (HCFC-225), perfluoroaliphatic hydrocarbons having 5 to 12 carbon atoms (e.g., perfluorohexane, perfluoromethylcyclohexane, and perfluoro-1,3-dimethylcyclohexane); polyfluoroaromatic hydrocarbons (e.g., bis(trifluoromethyl)benzene); polyfluoroaliphatic hydrocarbons (e.g., C ６ F １３ CH ２ CH ３(e.g., Asahiklin (registered trademark) AC-6000 manufactured by Asahi Glass Co., Ltd.), 1,1,2,2,3,3,4-heptafluorocyclopentane (e.g., Zeorora (registered trademark) H manufactured by Zeon Corporation); hydrofluoroethers (HFEs) (e.g., perfluoropropyl methyl ether (C ３ F ７ OCH ３ ) (e.g., Novec (trademark) 7000 manufactured by Sumitomo 3M Limited), perfluorobutyl methyl ether (C ４ F ９ OCH ３ ) (e.g., Novec (trademark) 7100 manufactured by Sumitomo 3M Limited), 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) (the perfluoroalkyl group and the alkyl group may be linear or branched), or CF ３ CH ２ OCF ２ CHF ２Examples of suitable solvents include aromatic hydrocarbons (e.g., benzene, toluene, xylene, mesitylene) (e.g., Asahiklin (registered trademark) AE-3000 manufactured by Asahi Glass Co., Ltd.); sulfone-based solvents (e.g., dimethyl sulfone, sulfolane); ether-based solvents (e.g., tetrahydrofuran, 1,4-dioxane, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, monoglyme, diglyme, triglyme, tetraglyme); acetonitrile; nitromethane; amide-based solvents (N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylpropyleneurea, 1,3-dimethyl-2-imidazolidinone); ester-based solvents (e.g., ethyl acetate, butyl acetate); and ketone-based solvents (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone).

[0279] The reaction temperature in the above reaction may be preferably 0 to 60° C., more preferably 10 to 40° C., for example, room temperature. The reaction time in the above reaction may be, for example, 1 to 72 hours, preferably 12 to 48 hours.

[0280] (Production Method 1: Production of Aromatic Polymer) The aromatic polymer represented by the above formula (I-2) can be produced by polymerizing aromatic monomers, and commercially available products may be used.

[0281] The aromatic monomer includes a compound having an aromatic ring and two or more groups having an active hydrogen atom, and preferably a compound represented by the following formula (III): ４ -Ar ３ -R ４ (III) [In formula (III), Ar ３ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, R ４ is independently at each occurrence -OH, -NH ２ , and a fluorine atom or a chlorine atom.]

[0282] Ar ３each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group.

[0283] C which may have one or more of the above-mentioned substituents ６－２０ "C" in a divalent group containing an aromatic hydrocarbon group ６－２０ The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic ring, two or more rings may or may not form a condensed ring. ６－２０ The number of aromatic hydrocarbon groups contained in the divalent group containing an aromatic hydrocarbon group is 1 or more, preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. ６－２０ In the divalent group containing an aromatic hydrocarbon group, two or more rings may be bonded via a single bond or a divalent organic group. ６－２０ The two or more substituents that the divalent group containing an aromatic hydrocarbon group may have are bonded to each other to form the above C ６－２０ They may be combined with the aromatic hydrocarbon group to form a ring.

[0284] Ar ３is preferably a group represented by the above formula (Ar1), and more preferably a phenylene group, a xylylene group, a naphthylene group, a biphenylene group, a 3,3'-dimethylbiphenylene group, a 2,2'-dimethylbiphenylene group, a 2,2'-dimethoxybiphenylene group, a 3,3',5,5'-tetramethylbiphenylene group, a 3,3',5,5'-tetraethylbiphenylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 2,2-diphenylpropane-4,4'-diyl group, a 1, It is a 1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and more preferably a phenylene group, a xylylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group.

[0285] R ４ is independently at each occurrence -OH, -NH ２ , a fluorine atom or a chlorine atom, preferably —OH or NH ２ In one embodiment, two R ４ are different from each other, for example, one R ４ is —OH, and one R ４ can be a fluorine atom. In another embodiment, two R ４ may be the same group.

[0286] The aromatic polymer represented by the above formula (I-2) may be produced by reacting an aromatic monomer with a second monomer.

[0287] Examples of such second monomers include monomers that can react with the aromatic monomer represented by formula (III), and preferred are monomers having two or more groups that can react with an amino group or a hydroxyl group in one molecule. Examples of such monomers include, for example, monomers represented by the following formula (IV): ５ -L １０ -R ５ (IV) [In formula (IV), R ５are each independently in each occurrence the following formulas (r-1) to (r-18): [In formulas (r-1) to (r-18), * represents a bond.], L １０ are expressed by the following formulas (l-1) to (l-11): [In formulas (l-1) to (l-11), R ６ is a C optionally substituted by one or more fluorine atoms; １－１６ an alkylene group or a C group optionally having one or more substituents; ６－２０ In formula (IV), R represents a divalent group containing an aromatic hydrocarbon group, and * represents a bond. ５ is a divalent group, L １０ can be a tetravalent group, for example, a group represented by the following formula: (*-) ２ R ６０ (-*) ２ (1-12) (R ６０ is a C optionally substituted by one or more fluorine atoms; １－１６ an alkanetetrayl group or a tetravalent C group optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group).

[0288] R ６ is a C optionally substituted by one or more fluorine atoms; １－１６ an alkylene group or a C group optionally having one or more substituents; ６－２０ represents a divalent group containing an aromatic hydrocarbon group.

[0289] The C optionally substituted with one or more fluorine atoms １－１６ "C" in the alkylene group １－１６ The "alkylene group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－１０ alkylene groups, more preferably straight or branched C １－５ In one embodiment, the C １－３Alkylene groups, specifically, —CH ２ -, -CH ２ CH ２ -, -CH ２ CH ２ CH ２ -It can be.

[0290] C which may have one or more of the above-mentioned substituents １－１６ The alkylene group may be substituted with one or more fluorine atoms. ６ is preferably a C substituted by one or more fluorine atoms １－１６ is a fluoroalkylene group, more preferably C １－１６ A perfluoroalkylene group, more preferably C １－６ perfluoroalkylene groups, more preferably C １－３ In another embodiment, the R ６ is a C that is not substituted by a fluorine atom １－１６ It may be an alkylene group.

[0291] Above C １－１６ The perfluoroalkylene group may be a straight chain or a branched chain, and preferably is a straight chain or branched chain C １－６ perfluoroalkylene groups, more preferably straight-chain or branched C １－３ Perfluoroalkylene groups, specifically, —CF ２ -, -CF ２ CF ２ -, -CF ２ CF ２ CF ２ -, -CF ２ CF (CF ３ )-.

[0292] C which may have one or more of the above-mentioned substituents ６－２０ "C" in a divalent group containing an aromatic hydrocarbon group ６－２０ The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic ring, two or more rings may or may not form a condensed ring.６－２０ The number of aromatic hydrocarbon groups contained in the divalent group containing an aromatic hydrocarbon group is 1 or more, preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. Such aromatic hydrocarbon groups are preferably C ６－１０ It is an aromatic hydrocarbon group, more preferably a phenylene group, a tolylene group, a xylylene group or a naphthylene group, and even more preferably a phenylene group, a tolylene group or a xylylene group.

[0293] C which may have one or more of the above-mentioned substituents ６－２０ In the divalent group containing an aromatic hydrocarbon group, two or more aromatic hydrocarbon groups may be bonded via a single bond or an organic group. Such an organic group may be a linear or branched C １－４ Examples of suitable alkyl groups include:

[0294] The above R ６ The divalent group containing an aromatic hydrocarbon group represented by the formula (Ar1) is preferably a group represented by the formula (Ar1) above, and more preferably a phenylene group, a tolylene group, a xylylene group, a naphthylene group, a biphenylene group, a 3,3'-dimethylbiphenylene group, a 2,2'-dimethylbiphenylene group, a 2,2'-dimethoxybiphenylene group, a 3,3',5,5'-tetramethylbiphenylene group, a 3,3',5,5'-tetraethylbiphenylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1, It is preferably a 1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and more preferably a phenylene group, a xylylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group.

[0295] Examples of the compound represented by the formula (IV) include R ５ is a group represented by any one of formulas (r-1), (r-2) and (r-9), and L １０ is a group represented by formula (l-3);５ is a group represented by either formula (r-3) or (r-10), and L １０ is a group represented by any one of formulas (l-1), (l-4), (l-7), (l-8) and (l-9); ５ is a group represented by any one of formulas (r-3), (r-5), (r-6), (r-7), (r-8), (r-10), (r-11), (r-12), (r-13) and (r-14), and L １０ is a group represented by any one of formulas (l-1), (l-4), (l-7), (l-8), (l-9) and (l-10); ５ is a group represented by formula (r-4), and L １０ is a group represented by any one of formulas (l-1) to (l-7); ５ is a group represented by formula (r-15), and L １０ is a compound represented by formula (l-12); R ５ is a group represented by formula (r-17), and L １０ is a compound represented by formula (l-9); R ５ is a group represented by formula (r-18), and L １０ is preferably a compound represented by formula (l-3), (l-5), (l-8) or (l-10).

[0296] The second monomer may be preferably 0.1 mol or more and 10 mol or less, more preferably 0.2 mol or more and 5 mol or less, and even more preferably 0.5 mol or more and 2 mol or less, per 1 mol of the aromatic monomer.

[0297] The reaction using the aromatic monomer as a monomer and the reaction between the aromatic monomer and the second monomer can be carried out by known methods.

[0298] (Production Method 2) The present disclosure also provides a compound represented by the following formula (I-1): [In formula (I-1), A １ each occurrence independently represents a divalent organic group containing one or more imide rings and optionally having one or more substituents; １ each occurrence independently represents a C which may have one or more substituents６－２０ represents a divalent group containing an aromatic hydrocarbon group, １ is independently at each occurrence -R １１ -, -O-, -S-, -NR １２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ -, -NR １２ —CO— and CO—NR １２ represents one selected from the group consisting of -, １１ each occurrence independently represents an optionally substituted C １－１６ an alkylene group and a C group optionally having one or more substituents; ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, １２ each occurrence independently represents an optionally substituted C １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, k1, in each occurrence, independently represents an integer of 0 or more and 4 or less, l1, in each occurrence, independently represents an integer of 1 or more and 4 or less, m1, in each occurrence, independently represents an integer of 0 or more and 4 or less, n1 represents an integer of 1 or more, in the unit enclosed in parentheses with n1, the units enclosed in parentheses with k1, l1, and m1 may appear in any order, and in formula (I-1), １－２０ a fluorine-containing aromatic polymer represented by the following formula (II): I-R ｆ１ (II) [In formula (II), R ｆ１ is C １－２０ represents a fluorine-containing organic group. ] to obtain a fluorine-containing aromatic monomer (hereinafter also referred to as a "fluorine-containing organic group introduction reaction into an aromatic monomer"), and using the fluorine-containing aromatic monomer as a monomer to obtain a fluorine-containing aromatic polymer (hereinafter also referred to as a "fluorine-containing aromatic polymer polymerization reaction") (Production Method 2).

[0299] According to the above-mentioned production method 2, since the fluorine-containing organic group is introduced at the monomer stage, the bonding position of the fluorine-containing organic group in the obtained fluorine-containing aromatic polymer is clear, and it is possible to design a more ordered main chain structure. This can be an effective production method for enhancing the properties of, for example, crystallinity, high Tg, and low CTE. Furthermore, it can be easy to obtain a fluorine-containing aromatic polymer having a high distribution density of the fluorine-containing organic group and in which the properties of the fluorine-containing organic group are more fully reflected. On the other hand, it is also possible to reduce and / or control the distribution density of the fluorine-containing organic group to a desired range by copolymerizing a fluorine-free monomer as necessary.

[0300] A １ , Ar １ , L １ ,k1,l1,m1,R １１ , R １２ and R ｆ１ has the same meaning as above.

[0301] The aromatic monomer includes a compound that contains an aromatic ring and has two or more groups having active hydrogen atoms, and more preferably a compound that contains an aromatic ring and has a hydroxyl group (—OH) and an amino group (—NH ２ ) and more preferably, an aromatic monomer represented by the above formula (III).

[0302] When the above-mentioned fluorine-containing aromatic monomer is used as a monomer to obtain a fluorine-containing aromatic polymer, the above-mentioned fluorine-containing aromatic monomer may be reacted with a second monomer. Such a second monomer may be a monomer capable of reacting with the aromatic monomer represented by formula (III), and preferably a monomer having two or more groups capable of reacting with an amino group or a hydroxyl group in one molecule. Such a monomer may be a compound represented by formula (IV).

[0303] The second monomer may be preferably 0.1 mol or more and 10 mol or less, more preferably 0.2 mol or more and 5 mol or less, and even more preferably 0.5 mol or more and 2 mol or less, per 1 mol of the fluorine-containing aromatic monomer.

[0304] (Production Method 2: Reaction for Introducing a Fluorine-Containing Organic Group into an Aromatic Monomer) In the reaction between an aromatic monomer and a compound represented by formula (II), the amount of the compound represented by formula (II) may be preferably 0.01 mol or more, more preferably 0.02 mol or more and 10 mol or less, and even more preferably 0.05 mol or more and 5 mol or less, per 1 mol of the aromatic monomer.

[0305] The reaction of the aromatic monomer with the compound represented by formula (II) may be carried out under irradiation with light, preferably ultraviolet light, having a wavelength of 300 to 400 nm, for example, 350 to 380 nm.

[0306] The light source used for such light irradiation is not particularly limited, but examples thereof include an LED, a mercury lamp, a xenon lamp, a UV lamp, and a halogen lamp, with an LED being preferred.

[0307] The reaction can be preferably carried out using a basic compound, a catalyst, a one-electron reducing agent, or a radical generator, any of the compounds described above in Production Method 1.

[0308] The above reaction is preferably carried out in a solvent, and any of the solvents mentioned above in Production Method 1 can be used as the solvent.

[0309] The reaction temperature in the above reaction may be preferably 0 to 60° C., more preferably 10 to 40° C., for example, room temperature. The reaction time in the above reaction may be, for example, 1 to 72 hours, preferably 12 to 48 hours.

[0310] (Production Method 2: Polymerization Reaction of Aromatic Polymer) The reaction using the fluorine-containing aromatic monomer as a monomer can be carried out by a known method for carrying out a reaction using an aromatic monomer as a monomer. The reaction between the fluorine-containing aromatic monomer and the second monomer can be carried out by a known method for carrying out a reaction between the aromatic monomer and the second monomer.

[0311] In this reaction, the reaction solvent that can be used is the same as that described in Production Method 1. The type and amount of the solvent may be appropriately determined depending on the fluorine-containing aromatic monomer and second monomer used.

[0312] (Fluorine-containing aromatic monomer) The present disclosure provides a fluorine-containing aromatic monomer represented by the following formula (III-1): ４１ -A ３１ -R ４１ (III-1) [In formula (III-1), Ar ３１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group, R ４１ is independently at each occurrence -OH, -NH ２ , a glycidyloxy group, a fluorine atom, or a chlorine atom; １－２０ The C １－２０ The fluorine-containing organic group is represented by the following formula (2-1A) and formula (2B): ３３ -X １ - (R Ｆ１ ) ｒ -CF ２ -* (2-1A) *-X １ -CF ２ -* (2B) [In formula (2-1A) and formula (2B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３３ is a C which may have one or more substituents ６－２０an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ each occurring independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, and the number of carbon atoms contained in formula (2-1A) or formula (2B) is 1 or more and 20 or less.

[0313] Using such a fluorine-containing aromatic monomer, a fluorine-containing aromatic polymer can be produced. By using such a fluorine-containing aromatic monomer, the bonding positions of the fluorine-containing organic groups in the resulting fluorine-containing aromatic polymer can be clarified, making it possible to design a more ordered main chain structure. This can be an effective production method for enhancing properties such as crystallinity, high Tg, and low CTE. Furthermore, by using such a fluorine-containing aromatic monomer, it can be easy to obtain a fluorine-containing aromatic polymer having a high distribution density of the fluorine-containing organic groups and in which the properties of the fluorine-containing organic groups are more fully reflected. On the other hand, it is also possible to reduce and control the distribution density of the fluorine-containing organic groups to a desired range by copolymerizing a fluorine-free monomer as necessary.

[0314] X １ , R Ｆ１ , R ｆ２ , R ｆ３ , p, q and r are as defined above.

[0315] Ar ３１ each occurrence independently represents a C which may have one or more substituents ６－２０ represents a divalent group containing an aromatic hydrocarbon group.

[0316] C which may have one or more of the above-mentioned substituents ６－２０ "C" in a divalent group containing an aromatic hydrocarbon group ６－２０ The "aromatic hydrocarbon group" may be monocyclic or polycyclic, and in the case of a polycyclic ring, two or more rings may or may not form a condensed ring. ６－２０ The number of aromatic hydrocarbon groups contained in the divalent group containing an aromatic hydrocarbon group is 1 or more, preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. ６－２０ In a divalent group containing an aromatic hydrocarbon group, two or more rings may be bonded via a single bond or a divalent organic group.

[0317] Ar ３１ is preferably a group represented by the above formula (Ar1), more preferably a phenylene group, a xylylene group, a naphthylene group, a biphenylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group, and more preferably a phenylene group, a xylylene group, a 2,2-diphenylpropane-4,4'-diyl group, a 1,1-diphenylmethane-4,4'-diyl group, a benzophenone-4,4'-diyl group, a diphenylsulfone-4,4'-diyl group, or an oxybisphenyl-4,4'-diyl group.

[0318] R ４１ is independently at each occurrence -OH, -NH ２ , a glycidyloxy group, a fluorine atom or a chlorine atom, preferably —OH or NH ２ In one embodiment, two R ４１are different from each other, for example, one R ４１ is —OH, and one R ４１ can be a fluorine atom. In another embodiment, two R ４１ may be the same group.

[0319] R ３３ is a C which may have one or more substituents ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom.

[0320] C which may have one or more of the above-mentioned substituents ６－２０ Substituents in the aromatic hydrocarbon group include halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms; １－４ Alkyl group; C １－４ Alkoxy group; R ２０ -O-CO- (where R ２０ is C １－４ R is an alkyl group, preferably a halogen atom, and particularly preferably a fluorine atom. ２０ may be linear or branched, preferably linear or branched C １－３ It is an alkyl group, specifically, —CH ３ , -CH ２ CH ３ is preferred.

[0321] The above R ３３ C represented by ６－２０ The aromatic hydrocarbon group is preferably a C ６－１０ An aromatic hydrocarbon group, more preferably a C ６－１０ In one embodiment, the R ３３ C represented by ６－２０The aromatic hydrocarbon group preferably has a substituent. In another embodiment, the R ３３ C represented by ６－２０ The aromatic hydrocarbon group preferably has no substituent.

[0322] The above R ３３ The "silsesquioxane residue" in the silsesquioxane residue which may have one or more substituents represented by the following formula is a monovalent group in which one substituent on Si in the silsesquioxane has been eliminated, and may have any of a cage structure, a ladder structure, or a random structure.

[0323] The substituent in the silsesquioxane residue which may have one or more substituents is preferably a C which may be substituted with one or more halogen atoms. １－１０ an alkyl group; a phenyl group, more preferably a C group optionally substituted with one or more halogen atoms; １－６ The alkyl group is a phenyl group.

[0324] C optionally substituted with one or more halogen atoms as a substituent of the silsesquioxane residue １－１０ "C" in the alkyl group １－１０ The "alkyl group" may be a straight chain or a branched chain, and is preferably a straight chain or branched chain C １－８ alkyl group, more preferably a straight-chain C １－６ It is an alkyl group.

[0325] C optionally substituted with one or more halogen atoms as a substituent of the silsesquioxane residue １－１０ Examples of the halogen atom in the alkyl group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and preferred examples include a fluorine atom and an iodine atom.

[0326] C optionally substituted with one or more halogen atoms as a substituent of the silsesquioxane residue １－１０ The alkyl group is preferably -CHI-CH ２ -CF ２ CF ２ CF２ -I.

[0327] As the substituent in the silsesquioxane residue which may have one or more substituents, a phenyl group or an isobutyl group is preferred.

[0328] R ３３ is an iodine atom, in the unit represented by formula (2-1A), R ３３ is replaced with a bond, and the R ３３ X bonded to １ may be bonded to an aromatic ring of another fluorine-containing aromatic monomer. Although the present disclosure should not be interpreted as being limited to a particular theory, the above structure is thought to be as follows. That is, when producing the fluorine-containing aromatic monomer of the present disclosure, it is thought that the iodine atom of a compound in which an iodine atom is bonded to a unit represented by formula (2-1A) is abstracted to become a reaction site, and is bonded to the aromatic ring of the aromatic monomer, thereby obtaining the fluorine-containing aromatic monomer represented by formula (III-1). R ３３ is an iodine atom, R ３３ It is believed that the iodine atom corresponding to R can be similarly abstracted and bonded to another aromatic ring. ３３ The same applies when an I atom is contained in the substituent of the group represented by the formula: and the group bonded to such an I atom may be bonded to another aromatic ring.

[0329] R ３３ is preferably a C which may have one or more substituents ６－２０ Aromatic hydrocarbon group, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom. * represents a bond.

[0330] The total number of carbon atoms in formula (2-1A) may be 1 or more and 20 or less, and preferably 1 or more and 15 or less. The total number of carbon atoms in formula (2B) may be 1 or more and 20 or less, and preferably 1 or more and 15 or less.

[0331] C represented by the above formula (2-1A) and formula (2B) １－２０ The fluorine-containing organic group is C １－２０ Fluoroalkyl groups, C having functional groups １－２０ Fluorine-containing organic group, or C １－２０ Specifically, the above formulas (2-1A) and (2B) can be expressed by the following formulas (2-1a), (2-1b), (2-1c), and (2B): F-X １ -CF ２ -* (2-1a) R ３３ -X １ -CF ２ -* (2-1b) R ３３ -X １ -R Ｆ１ -CF ２ -* (2-1c) *-X １ -CF ２ -* (2B) [in formula (2-1a), formula (2-1b), formula (2-1c) and formula (2B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３３ is a C which may have one or more substituents ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom or a bromine atom; R ｆ２each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４ are each independently in each occurrence a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, the number of carbon atoms contained in formula (2-1a) is 1 or more and 20 or less, the number of carbon atoms contained in formula (2-1b) is 1 or more and 20 or less, the number of carbon atoms contained in formula (2-1c) is 1 or more and 20 or less, and the number of carbon atoms contained in formula (2B) is 1 or more and 20 or less.

[0332] The number of fluorine-containing organic groups contained in the fluorine-containing aromatic monomer is 1 or more, preferably 1 to 8, more preferably 1 to 4, and even more preferably 1 to 3. The number of fluorine-containing organic groups contained in the fluorine-containing aromatic monomer is preferably 1 to 4, more preferably 1 to 2, per aromatic ring contained in the fluorine-containing aromatic monomer. In one embodiment, the fluorine-containing organic group is C １ Fluorine-containing organic groups (especially -CF ３ ), the number of the fluorine-containing organic groups per unit is preferably 2 to 6, more preferably 2 to 4, and even more preferably 3 to 4. In addition, in such an aromatic ring, the substitution positions of the fluorine-containing organic groups are ４１ Preferably, it is in the ortho position relative to

[0333] (Article) An article comprising a substrate and a layer formed on the surface of the substrate from a surface treatment agent, wherein the substrate comprises an aromatic polymer, and the surface treatment agent is represented by the following formula (II-1A) and formula (II-1B): R ３２ -X １ - (R Ｆ１ ) ｒ -CF ２-I (II-1A) I-X １ -CF ２ -I (II-1B) [In formula (II-1A) and formula (II-1B), R Ｆ１ is -(Rf) ｐ -R Ｆ -(O) ｑ Rf, at each occurrence, independently represents a C group optionally substituted by one or more fluorine atoms; １－１６ represents an alkylene group, Ｆ represents a divalent fluoro(poly)ether group; X １ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkylene group or a single bond, ３２ is a C optionally substituted by one or more halogen atoms; １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, —COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C optionally substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, ｆ３ is a C optionally substituted by one or more halogen atoms; １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom; ｆ４each occurring independently represents a hydrogen atom or a fluorine atom, p is 0 or 1, q is 0 or 1, r is 0 or 1, * represents a bond, the number of carbon atoms contained in formula (II-1A) is 1 or more and 20 or less, and the number of carbon atoms contained in formula (II-1B) is 1 or more and 20 or less.] Also included within the technical scope of the present disclosure is an article containing a compound represented by one or more selected from the following.

[0334] The article of the present disclosure has a substrate containing an aromatic polymer to which a fluorine-containing organic group is attached, and is therefore expected to further improve the heat resistance of the aromatic polymer while also providing flexibility, stain resistance, friction properties, stain resistance, and water and oil repellency.

[0335] The substrate may be any one containing an aromatic polymer, such as a polyimide resin, a polyetherimide resin, a polyamideimide resin, a polysulfone resin, an aromatic polyamide resin, a polyetheretherketone resin, a polyethersulfone resin, an aromatic polyester resin, a phenol resin, a cresol resin, an epoxy resin, or a polyamic acid resin containing an aromatic ring.

[0336] The substrate may be composed solely of an aromatic polymer, or may be a combination of an aromatic polymer and other materials, such as glass, other resins, metals (simple metals such as aluminum, copper, and iron, or alloys containing such simple metals), ceramics, semiconductors (silicon, germanium, and the like), fur, leather, wood, paper, ceramics, stone, and fabrics.

[0337] The substrate may be in the form of a powder, a membrane, a plate, a film, a pellet, a molded body (various parts, etc.), a fiber (yarn, woven fabric, nonwoven fabric), etc. The surface region of the substrate on which a layer is to be formed with the surface treatment agent may be at least a part of the substrate surface, and can be appropriately determined depending on the use and specific specifications of the article to be manufactured. For example, it is possible to introduce a fluorine-containing organic group only into a part of the surface of a molded body.

[0338] The surface treatment agent contains one or more compounds selected from formula (II-1A) and formula (II-1B), and preferably contains the compound represented by formula (II-1A). In one embodiment, the surface treatment agent may further contain, in addition to one or more compounds selected from formula (II-1A) and formula (II-1B), a basic compound, a catalyst, a one-electron reducing agent, a radical generator, a solvent, etc. As such basic compound, catalyst, one-electron reducing agent, radical generator, and solvent, the same compounds as those described in Production Method 1 can be used.

[0339] (Method for Producing an Article) The method for producing an article of the present disclosure includes reacting the substrate with the surface treatment agent to form a layer on the surface of the substrate, wherein the substrate includes an aromatic polymer, and the surface treatment agent includes one or more compounds selected from formula (II-1A) and formula (II-1B) above, and preferably includes the compound represented by formula (II-1A) above.

[0340] According to the method for producing an article of the present disclosure, a fluorine-containing organic group is imparted to a substrate containing an aromatic polymer, and therefore it is expected that the heat resistance of the aromatic polymer can be further improved or maintained while additionally imparting flexibility, stain resistance, friction properties, stain resistance, and water and oil repellency.

[0341] The reaction may be carried out under light irradiation. Such light irradiation is preferably ultraviolet light irradiation, and can be carried out by irradiating with light having a wavelength of 300 to 400 nm, for example, 350 to 380 nm. The light source used for such light irradiation can be the light source described in Production Method 1.

[0342] The reaction temperature in the above reaction is preferably 0 to 60° C., more preferably 10 to 40° C., for example, room temperature. The reaction time in the above reaction is, for example, 1 to 72 hours, preferably 12 to 48 hours.

[0343] The method for producing the article may further include removing unreacted surface treatment agent and / or by-products after forming the layer on the surface of the substrate. The removal of unreacted surface treatment agent and / or by-products can be carried out by one or more methods selected from washing and drying. Articles from which the unreacted surface treatment agent and / or by-products have been removed are also included in the technical scope of the article of the present disclosure.

[0344] The present invention will be explained in more detail with reference to the following examples, but the present invention is not limited to these examples.

[0345] Example 1: To a dichloromethane solution of 3,3',5,5'-tetramethylbenzidine (1) (0.3 mmol), perfluorohexyl iodide (5 equivalents), 5 equivalents of aqueous sodium thiosulfate solution (2 mL of water), and 3 equivalents of cesium carbonate were added, and the mixture was irradiated with light from a 365 nm LED for 48 hours. After completion of the reaction, the mixture was separated and then purified by column chromatography, resulting in the isolation of the target diamine compound (2) in a 32% yield. Spectrum of Compound 2 1 H NMR (400 MHz, CDCl3) δ 6.82 (s, 1H), 6.75 (s, 2H), 3.75 (s, 2H), 3.54 (s, 2H), 2.27 (s, 3H), 2.19 (s, 3H), 2.17 (s, 6H) 19 F NMR (376 MHz, CDCl3) δ -81.29 (s, 3F), -95.18 (s, 2F), -118.13 (s, 2F), -122.34 (s, 2F), -123.20 (s, 2F), -126.65 (s, 2F)

[0346] Example 2 One equivalent of 4,4'-oxydiphthalic anhydride (3) was added to a dimethylacetamide solution (0.23 mL) of diamine monomer (2) (58.9 mg, 0.11 mmol), and the mixture was stirred at room temperature for 1 hour. As a result, a viscous solution was obtained, and NMR and GPC measurements showed a number average molecular weight of 1.3 × 10 ３ It was found that polyamic acid (4) having a molecular weight distribution of 1.2 was obtained. Spectrum of compound 4 1H NMR (400 MHz, CDCl3) δ 8.09 - 7.57 (6H, m), 7.18 (1H, s), 7.08 (2H, s), 2.33 (3H, s), 2.20 (3H, s), 2.18 (6H, s). 19 F NMR (376 MHz, CDCl3) δ -81.1 (3F, s), -96.1 (2F, s), -117.9 (2F, s), -122.2 (2F, s), -123.0 (2F, s), -126.4(2F, s).

[0347] Example 3: To a dichloromethane solution (2.5 mL) of 3,3',5,5'-tetramethylbenzidine (1) (0.3 mmol), perfluoropropyl iodide (5 equivalents), 5 equivalents of aqueous sodium thiosulfate solution (2 mL of water), and 3 equivalents of cesium carbonate were added, and the mixture was irradiated with light from a 365 nm LED for 48 hours. After completion of the reaction, the mixture was separated and then purified by column chromatography, yielding the target diamine compound (5) in an isolated yield of 35%. Spectrum of compound 5 1 H NMR (400 MHz, CDCl3) δ 6.82 (s, 1H), 6.75 (s, 2H), 3.75 (s, 2H), 3.56 (s, 2H), 2.26 (s, 3H), 2.19 (s, 3H), 2.17 (s, 6H) 19 F NMR (376 MHz, CDCl3) δ -80.67 (s, 3F), -95.73 (s, 2F), -122.34 (s, 2F)

[0348] Example 4: To a dichloromethane solution (2.5 mL) of 3,3',5,5'-tetramethylbenzidine (1) (0.3 mmol), perfluoropropyl iodide (5 equivalents), 5 equivalents of aqueous sodium thiosulfate solution (2 mL of water), and 3 equivalents of cesium carbonate were added, and the mixture was irradiated with light from a 365 nm LED for 48 hours. After completion of the reaction, the mixture was separated and then purified by column chromatography. As a result, the target diamine compound (6) and compound (7) were obtained in isolation yields of 39% and 7%, respectively. Spectrum of compound 61 H NMR (400 MHz, CDCl3) δ 6.85 (1H, s), 6.83 (2H, s), 3.69 (4H, br s), 2.30 (3H, s), 2.30 (3H, s), 2.19 (6H, s). 19 F NMR (376 MHz, CDCl3) δ = -51.2 (3F, s). Spectrum of compound 7 1 H NMR (400 MHz, CDCl3) δ 6.68 (2H, s), 3.69 (4H, br s), 2.29 (6H, s), 2.18 (6H, s). 19 F NMR (376 MHz, CDCl3) δ -52.9 (6F, s).

[0349] Example 5: 5 equivalents of 1,4-diiodoperfluorobutane, 5 equivalents of aqueous sodium thiosulfate solution (2 mL of water), and 3 equivalents of cesium carbonate were added to a dichloromethane solution (2.5 mL) of 3,3',5,5'-tetramethylbenzidine (1) (0.3 mmol), and the mixture was irradiated with 365 nm LED light for 48 hours. After completion of the reaction, the mixture was separated and then purified by column chromatography, resulting in the target diamine compound (8) in an isolated yield of 13%. Spectrum of compound 8 1 H NMR (400 MHz, CDCl3) δ 6.81 (1H, s), 6.74 (2H, s), 3.74 (2H, br s), 3.54 (2H, br s), 2.26 (3H, s), 2.18 (3H, s), 2.20 (6H, s). 19 F NMR (376 MHz, CDCl3) δ -58.1 (2F, s), -95.1 (2F, s), -113.1 (2F, s), -117.1 (2F, s).

[0350] Example 6: 5 equivalents of 1,6-diiodoperfluorohexane, 5 equivalents of aqueous sodium thiosulfate solution (2 mL of water), and 3 equivalents of cesium carbonate were added to a dichloromethane solution (2.5 mL) of 3,3',5,5'-tetramethylbenzidine (1) (0.3 mmol), and the mixture was irradiated with 365 nm LED light for 48 hours. After completion of the reaction, the mixture was separated and then purified by column chromatography, resulting in the isolation of the target diamine compound (9) in a 14% yield. Spectrum of compound 9 1 H NMR (400 MHz, CDCl3) δ 6.82 (1H, s), 6.75 (2H, s), 3.75 (2H, br s), 3.54 (2H, br s), 2.27 (3H, s), 2.19 (3H, s), 2.17 (6H, s). 19 F NMR (376 MHz, CDCl3) δ -59.1 (2F, s), -95.1 (2F, s), -113.5 (2F, s), -118.0 (2F, s), -121.3 (2F, s), -123.9 (2F, s).

[0351] Example 7: To a dichloromethane solution (2 mL) of 3,3'-tetramethylbenzidine (10), 1 equivalent of perfluorohexyl iodide, 5 equivalents of aqueous sodium thiosulfate solution (2 mL), and 3 equivalents of cesium carbonate were added, and the mixture was irradiated with 365 nm LED light for 24 hours. As a result, the target diamine compound (11) was obtained in an isolated yield of 12%. Spectrum of compound 11 1 H NMR (400 MHz, CDCl3) δ 7.52 - 6.62 (5H, m), 4.20 (2H, br s), 3.48 (2H, br s), 2.32 (3H, s), 2.17 (3H, s). 19 F NMR (376 MHz, CDCl3) δ -81.17 (3F, s), -108.27 (2F, s), -122.0 (4F, s), -123.1 (2F, s), -126.5 (2F, s).

[0352] Example 8: To a solution of 4,4'-dihydroxybiphenyl (12) (0.2 mmol) in acetonitrile (5 mL) / water (1 mL), 6 equivalents of perfluorohexyl iodide, phloxine B (20 mol%), ascorbic acid (4 equivalents), and cesium carbonate (3.5 equivalents) were added, and the mixture was irradiated with white LED light for 24 hours under an argon atmosphere. NMR analysis revealed that the target dihydroxy monomer (13) and (14) were produced in yields of 67% and 14%, respectively.

[0353] Example 9: 4,4'-Diaminodiphenylphenyl ether (15) (0.6 mmol) was mixed with 5 equivalents of perfluorohexyl iodide, 5 equivalents (4 mL) of aqueous sodium thiosulfate solution, and 3 equivalents of cesium carbonate, and the mixture was irradiated with light at 365 nm for 24 hours. The resulting reaction mixture was purified by column chromatography, yielding compound (16) with one perfluorohexyl group introduced in 4%, compound (17) with two perfluorohexyl groups introduced in 30%, and compound (18) with three perfluorohexyl groups introduced in 22% isolated yield. Spectrum of compound 17 1 H NMR (400 MHz, CDCl3) δ 6.99 (dd, 2H, J = 8.9, 3.0 Hz), 6.92 (d, 2H, J = 2.8 Hz), 6.71 (d, 2H, J = 9.2 Hz), 4.10 (s, 4H) 19 F NMR (376 MHz, CDCl3) δ -81.32 (s, 6F), -109.38 (s, 4F), -122.22 (s, 4F), -122.34 (s, 4F), -123.27 (s, 4F), -126.68 (s, 4F) 1 H NMR (400 MHz, CDCl3) δ 7.21 (s, 2H), 7.00 (dd, 1H, J = 8.9, 2.8 Hz), 6.93 (d, 1H, J = 3.2 Hz), 6.72 (d, 1H, J = 8.7 Hz), 4.75 (s, 2H), 4.15 (s, 2H) 19F NMR (376 MHz, CDCl3) δ -80.92 (s, 9F), -107.68 (s, 4F), -108.94 (s, 2F), -121.27 (s, 6F), -121.54 (s, 6F), -122.59 (s, 6F), -126.09 (s, 6F)

[0354] Example 10: 4,4'-diaminodiphenylphenyl ether (15) (0.6 mmol) was mixed with 2 equivalents of perfluorohexyl iodide, 5 equivalents (4 mL) of aqueous sodium thiosulfate solution, and 3 equivalents of cesium carbonate, and the mixture was irradiated with light at 365 nm for 24 hours. NMR analysis of the resulting reaction mixture confirmed that compound (18) with one perfluoropropyl group introduced was produced in 24% yield, and compound (19) with two perfluoropropyl groups introduced was produced in 4% yield. Spectrum of compound 18 1 H NMR (400 MHz, CDCl3) δ 6.97 (dd, 2H, J = 8.9, 3.0 Hz), 6.93 (d, 2H, J = 2.8 Hz), 6.70 (d, 2H, J = 9.2 Hz), 4.10 (s, 4H) 19 F NMR (376 MHz, CDCl3) δ -80.70 (s, 6F), -110.36 (s, 4F), -126.92 (s, 4F)

[0355] Example 11: To a mixed solution of 4,4'-dihydroxydiphenyl ether (20) in acetonitrile (5 mL) / water (1 mL), 1 equivalent of perfluorohexyl iodide, phloxine B (20 mol%), ascorbic acid (4 equivalents), and cesium carbonate (2.5 equivalents) were added, and the mixture was irradiated with white LED light for 24 hours under an argon atmosphere. NMR analysis revealed that the target dihydroxy monomer (21) was synthesized in a 21% yield. Spectrum of compound 21 1H NMR (400 MHz, CH3CN) δ 7.81 (s,1H), 7.54-7.53 (m,2H), 7.33-7.32 (m, 2H), 7.20-7.18 (m,1H), 7.14 (s, 1H), 3.96 (s,1H), 3.91 (s, 1H) 19 F NMR (376 MHz, CH3CN) δ -79.8 (s, 3F), -106.2 (s, 2F), -120.0 (s, 2F), -120.6 (s, 2F), -121.6 (s, 2F), -125.0 (s, 2F)

[0356] Example 12: To a solution of 4,4'-methylenediphenol (22) in acetonitrile (5 mL) / water (1 mL), 1 equivalent of perfluorohexyl iodide, phloxine B (20 mol%), ascorbic acid (4 equivalents), and cesium carbonate (2.5 equivalents) were added, and the mixture was irradiated with white LED light for 24 hours under an argon atmosphere. NMR analysis revealed that the target dihydroxy monomer (23) was synthesized in a 12% yield. Spectrum of compound 23 1 H NMR (400 MHz, CH3CN) δ 7.73 (m, 1H), 7.24-7.23 (m, 2H), 7.01-6.99 (m, 1H), 6.92-6.90 (m, 2H), 6.71-6.70 (m, 1H), 3.87 (s, 1H), 3.81 (s, 1H),2.05-2.04 (m, 2H) 19 F NMR (376 MHz, CH3CN) δ -79.4 (s, 3F), -106.3 (s, 2F), -119.8 (s, 2F), -120.2 (s, 2F), -124.5 (s, 2F)

[0357] (Example 13) Polyetherimide (24) (total amount of aromatic rings: 0.5 mmol) (M ｎ = 1.2 x 10 ４ , M ｎ / M ｎTo a dichloromethane solution (5 mL) of 1,2-dimethyl-2,4-dichloro ... ６ F １３ The target polymer (25) (M ｎ = 1.4 x 10 ４ , M ｗ / M ｎ = 2.90) was obtained in an isolated yield of 78%. In the following formula, the units enclosed in parentheses with X, Y and z may be present in any order. Spectrum of compound 26 1 H NMR (400MHz, CDCl3): δ= 8.24 (br), 7.91 (br), 7.64 (br), 7.51 (br), 7.43 (br), 7.34 (br), 7.07 (br), 1.75 (br) 19 F NMR (471MHz, CDCl3) :δ= -81.3 (3F, br), -108.6 (2F, br), -120.4 (2F, br), -121.1 (2F, br), -122.2 (2F, br), -123.2 (2F, br), -126.6 (2F, br)

[0358] (Example 14) Polyetherimide (24) (total amount of aromatic rings: 0.5 mmol) (M ｎ = 1.2 x 10 ４ , M ｎ / M ｎTo a dichloromethane solution (5 mL) of 1.64 (C = 1.64), 3 equivalents of perfluoropropyl iodide, 5 equivalents (1 mL) of aqueous sodium thiosulfate solution, and 3 equivalents (1 mL) of aqueous cesium carbonate solution were added, and the mixture was irradiated with light from a 365 nm LED at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was dissolved in a solvent and filtered again. The resulting filtrate was concentrated and purified again by reprecipitation. As a result, 18 mol% of all benzene rings contained C. ３ F ７ The target polymer (26) (M ｎ = 1.7 x 10 ４ , M ｗ / M ｎ = 2.36) was obtained in an isolated yield of 70%. In the following formula, the units enclosed in parentheses with X, Y, and z may be present in any order. While the raw polymer (24) was completely insoluble in acetone and acetonitrile, the produced polymer (26) was partially soluble in acetone and acetonitrile, confirming that the introduction of perfluoropropyl groups improved the solvent solubility. Spectrum of compound 26 1 H NMR (400MHz, CDCl3): δ= 8.20 (br), 7.87 (br), 7.64 (br), 7.63 (br), 7.50 (br), 7.42 (br), 7.26 (br), 7.02 (br), 1.75 (br) 19 F NMR (471MHz, CDCl3) :δ= -80.4 (3F, br), -80.6 (3F, br), -109.5 (2F, br), -124.6 (2F, br), -125.6 (2F, br), -126.3 (2F, br)

[0359] (Example 15) Polycarbonate (27) (total amount of aromatic rings: 0.5 mmol) (M ｎ = 2.3 x 10 ４ , M ｎ / M ｎTo a dichloromethane solution (5 mL) of 1,2-dimethyl-2,4-trifluoromethyl-2,4-di ... ３ F ７ The target polymer (28) (M ｎ = 3.1 x 10 ４ , M ｗ / M ｎ It was confirmed that the obtained value was 3.16. Spectrum of compound 28 1 H NMR (400MHz, CDCl3): δ= 7.26 (br), 7.18 (br), 1.70 (br) 19 F NMR (471MHz, CDCl3) :δ= -80.5 (3F, br), -110.0 (2F, br), -126.5 (2F, br)

[0360] (Example 16) Polyethylene terephthalate (29) (total amount of aromatic rings: 0.5 mmol) (M ｎ = 2.0 × 10 ４ , M ｎ / M ｎ To a dichloromethane solution (5 mL) of 1,2-dimethyl-2,4-dichloro ... ３ F ７ The target polymer (30) (M ｎ = 1.8 x 10 ４ , M ｗ / M ｎ It was confirmed that the compound (C10) was obtained in an isolated yield of 72%. Spectrum of compound 30 1 H NMR (400MHz, CDCl3): δ= 8.28 (br), 8.10 (br), 4.69 (br), 1.93 (br), 1.67 (br), 1.18 (br) 19 F NMR (471MHz, CDCl3) :δ= -80.5 (3F, br), -106.4 (3F, br), -124.3 (2F, br)

[0361] Example 17: Water (0.5 mL) and perfluorohexyl iodide (0.5 mL) were added to a petri dish to form two liquid layers. A polycarbonate sheet (manufactured by AS ONE Corporation: 63-508476, 2 cm square, 1 mm thick) was then suspended between the two layers, and irradiated with a 365 nm LED from above, allowing the surface reaction to proceed for 30 minutes. After the photoreaction was complete, the film was removed and washed with methanol. The water contact angle of the film surface (the upper surface closest to the LED light source) after washing had significantly improved from 44° to 102°. This result confirmed that perfluorohexyl groups had been introduced, imparting water repellency derived from their skeleton to the film surface.

[0362] Example 18: To a solution of 4,4'-dihydroxybiphenyl (12) (0.2 mmol) in acetonitrile (5 mL) / water (1 mL), 6 equivalents of perfluoropropyl iodide, phloxine B (20 mol%), ascorbic acid (4 equivalents), and cesium carbonate (2.5 equivalents) were added, and the mixture was irradiated with white LED light for 24 hours under an argon atmosphere. NMR analysis revealed that the target dihydroxy monomer (31) and (32) were synthesized in 30% and 3% yields, respectively. Spectrum of compound 31 1 H NMR (400 MHz, CH3CN) δ 7.27 (s, 1H), 7.43-7.42 (m, 1H), 7.20 (m, 1H), 7.05-7.04 (m, 2H), 7.03 (s, 1H), 6.88-6.86 (m, 1H), 4.61 (s, 1H), 4.54 (s, 1H) 19F NMR (376 MHz, CH3CN) δ -79.0 (s, 3F), -107.2 (s, 2F), -124.2 (s, 2F) spectrum of compound 32 19 F NMR (376 MHz, CH3CN) δ -79.0 (s, 3F), -106.4 (s, 2F), -120.4 (s, 2F)

[0363] Example 19 One equivalent of 4,4'-oxydiphthalic anhydride (3) was added to a dimethylacetamide solution (20 wt%) of diamine monomer (2) (0.26 mmol), and the mixture was heated and stirred at 50°C for 50 hours, then heated to 80°C for 14 hours, then heated to 110°C for 24 hours, and then heated to 140°C for 24 hours. Purification by reprecipitation revealed a number-average molecular weight of 5.5 x 10 ３ Polyimide (33) having a molecular weight distribution of 1.7 was obtained in an isolated yield of 69%. Spectrum of Compound 33 (polyimide) 1 H NMR (400 MHz, CDCl3) δ= 8.09 - 7.57 (6H, m), 7.18 (1H, s), 7.08 (2H, s), 2.33 (3H, s), 2.20 (3H, s) ,2.18 (6H, s). 19 F NMR (376 MHz, CDCl3) δ= -81.1 (3F, s), -96.1 (2F, s), -117.9 (2F, s), -122.2 (2F, s), -123.0 (2F, s), -126.4(2F, s).

[0364] Example 20: To a solution of 4-fluorophenol (34) (0.2 mmol) in acetonitrile (5 mL) / water (1 mL), 6 equivalents of perfluorohexyl iodide, phloxine B (20 mol%), ascorbic acid (4 equivalents), and cesium carbonate (2.5 equivalents) were added, and the mixture was irradiated with white LED light for 24 hours under an argon atmosphere. NMR analysis revealed that the desired AB-type monomer (35) and (36) were produced in yields of 30% and 8%, respectively.

[0365] Example 21 Under an argon atmosphere, 4,4'-oxydianiline (15, 0.3 mmol) was dissolved in CH ３ CN / H ２ To a 5 mL / 1 mL solution of 1H2O, 2 equivalents of heptafluoropropyl iodide, 10 mol% Eosin Y-2Na, 4 equivalents of ascorbic acid, and 2.5 equivalents of cesium carbonate were added, and the mixture was degassed by freezing. The mixture was then irradiated with white LED light and stirred at room temperature for 24 hours. The resulting reaction mixture was purified by column chromatography to give the mono-substituted product (18) in 32% yield and the di-substituted product (19) in 8% yield.

[0366] Example 22 Under an argon atmosphere, 4,4′-oxydianiline (15) (0.2 mmol) was dissolved in CH ３ CN / H ２ To a mixed solution of 1H 2 O (5 mL / 1 mL), 6 equivalents of perfluorohexyl iodide, 10 mol% EY, 4 equivalents of ascorbic acid, and 1.5 equivalents of cesium carbonate were added, and the mixture was irradiated with light from a white LED and stirred for 24 hours. NMR analysis confirmed that the monosubstituted product (37) and the disubstituted product (38) were produced in yields of 14% and 10%, respectively.

[0367] (Example 23) Compound (39) (0.6 mmol) was dissolved in CH ２ Cl ２ / H ２ 6 equivalents of perfluoropropyl iodide and Na ２ S ２ O ３ 5 equivalents of methylcellulose and 3 equivalents of cesium carbonate were added, and the mixture was irradiated with white LED and stirred for 24 hours. NMR analysis confirmed that compound (40) was produced in a 44% yield. Spectrum of compound 40 1 H NMR (400 MHz, CDCl3) δ 7.01 (s, 2H), 6.86 (s, 1H), 6.62 (s, 1H), 6.58 (s, 1H), 4.54 (s, 4H), 1.99 (s, 3H), 1.96 (s, 3H) 19F NMR (376 MHz, CDCl3) δ -80.61 (s, 3F), -102.25 (s, 2F), -126.95 (s, 2F)

[0368] (Example 24) Compound (41) (0.6 mmol) was dissolved in CH ２ Cl ２ / H ２ 6 equivalents of perfluoropropyl iodide and Na ２ S ２ O ３ Five equivalents of 4-methyl-2-propanol and three equivalents of cesium carbonate were added, and the mixture was irradiated with a white LED and stirred for 24 hours. The reaction mixture was purified by recycle preparative size exclusion chromatography to give compound (42) in an isolated yield of 12% and compound (43) in an isolated yield of 5%. Spectrum of compound 42 1 H NMR (400 MHz, CDCl3) δ 7.07 (s, 2H), 6.96 (dd, 1H, J = 8.0, 1.6 Hz), 6.93 (d, 1H, J = 1.8 Hz), 6.77 (d, 1H, J = 8.2 Hz), 3.94 (s, 3H), 3.92 (s, 3H) 19 F NMR (376 MHz, CDCl3) δ -80.58 (s, 3F), -109.71 (s, 2F), -126.80 (s, 2F)

[0369] (Example 25) Compound (44) (0.6 mmol) was dissolved in CH ２ Cl ２ / H ２ 6 equivalents of perfluoropropyl iodide and Na ２ S ２ O ３ 5 equivalents of methylcellulose and 3 equivalents of cesium carbonate were added, and the mixture was irradiated with white LED and stirred for 24 hours. NMR analysis confirmed that compound (45) was produced in a 7% yield. Spectrum of compound 45 1H NMR (400 MHz, CDCl3) δ 7.14 (s, 1H), 6.81 (s, 2H), 3.79 (s, 2H), 3.53 (s, 4H), 2.49 (s, 8H), 1.23 (s, 12H) 19 F NMR (376 MHz, CDCl3) δ -80.46 (s, 3F), -110.54 (s, 2F), -126.803 (s, 2F)

[0370] (Example 26) Compound (46) (5 equivalents) was dissolved in CH under an argon atmosphere. ２ Cl ２ / H ２ 0.3mmol of 1,4-diiodoperfluorobutane and Na ２ S ２ O ３ The mixture was irradiated with a white LED and stirred for 24 hours. NMR analysis confirmed that 20% of compound (47) and 9% of compound (48) were produced. Spectrum of Compound 47 (iodine-containing form) 1 H NMR (400 MHz, CDCl3): δ= 6.65 (s, 3H), δ= 3.82 (4H, br) 19 F NMR (376 MHz, CDCl): δ = −58.7 (2F, s), −109.0 (2F, s), −113.1 (2F, s), −121.2 (2F, s) Spectrum of compound 48 (cyclized product) 1 H NMR (400 MHz, CDCl3): δ= 6.72 (2H, d, J = 2.3 Hz), 4.07 (4H, br) 19 F NMR (376 MHz, CDCl3): δ= -108.0 (2F, s), -110.2 (2F, s), -135.3 (2F, s), -136.1 (2F, s)

[0371] Example 27: Compound (49) (5 equivalents) was dissolved in CH under an argon atmosphere. ２ Cl ２ / H ２0.3mmol of 1,4-diiodoperfluorobutane and Na ２ S ２ O ３ The mixture was irradiated with a white LED and stirred for 24 hours. Purification by column chromatography afforded compound (50) in an isolated yield of 20% and compound (51) in an isolated yield of 3%. Spectrum of Compound 50 (iodine-containing form) 1 H NMR (400 MHz, CDCl3): δ= 6.93 (4H, d, J = 8.7 Hz), 6.58 (1H, d, J = 7.8 Hz), 4.12 (4H, br), 2.21 (6H, s) 19 F NMR (376 MHz, CDCl): δ = −58.6 (2F, s), −108.4 (2F, s), −113.1 (2F, s), −121.1 (2F, s) Spectrum of compound 51 (cyclized form) 1 H NMR (400 MHz, CDCl3): δ= 7.39 (3H, d, J = 8.7 Hz), 6.65 (1H, d, J = 7.8 Hz), 4.54 (4H, br), 2.16 (3H, s), 2.15 (3H, s) 19 F NMR (376 MHz, CDCl3): δ= -107.6 (2F, s), -108.4 (2F, s), -134.5 (2F, s), -136.3 (2F, s)

[0372] Example 28: Under an argon atmosphere, 5 equivalents of compound (15) were dissolved in CH ２ Cl ２ / H ２ 0.3mmol of 1,4-diiodoperfluorobutane and Na ２ S ２ O ３ The mixture was irradiated with a white LED and stirred for 24 hours. Purification by column chromatography gave compound (52) in an isolated yield of 22%. Spectrum of compound 521 H NMR δ 6.71-6.73 (3H, m), 6.56-6.59 (4H, m), 5.25 (4H, s) 19 F NMR δ -73.6 (2F, s), -114.1 (2F, s), -119.7 (2F, s), -126.9 (2F, s)

[0373] Example 29: Polyimide was synthesized using the monosubstituted 4,4'-oxydianiline (18). Under an argon atmosphere, one equivalent of 6FDA was added to a DMF (50 wt%) solution of the monosubstituted 4,4'-oxydianiline (18, 0.5 mmol), and the mixture was stirred at 180°C for 2.5 hours. DMF was then added to the reaction solution to dissolve the product, which was then reprecipitated using water / methanol (50 mL / 50 mL) as a poor solvent. The resulting solid was collected by filtration, dried, and then subjected to NMR and GPC analysis (Scheme 8). Polyimide (53) with a number-average molecular weight of 3,900 and a molecular weight distribution of 2.83 was obtained in 96% isolated yield. The resulting polyimide 53 was soluble in tetrahydrofuran, DMF, and chloroform. Spectrum of compound 53 1 H NMR (400 MHz, CDCl3) δ = 8.09-8.04 (2H, m), 8.00-7.90 (4H, m), 7.52-7.50 (2H, m), 7.34-7.32 (2H, m), 7.27-7.26 (3H, m) 19 F NMR (376 MHz, CDCl3) δ = -63.71 (6F, s), -80.34 (3F, s), -109.74 (2F, s), -125.57 (2F, s)

[0374] (Example 30) Polycarbonate (27) (total amount of aromatic rings: 0.5 mmol) (M ｎ = 2.3 x 10 ４ , M ｎ / M ｎ = 3.26) CH ２ Cl ２ / H ２To a 5 mL / 2 mL solution of 1,4-diiodoperfluorobutane (0.3 equivalents), 5.0 equivalents of aqueous sodium thiosulfate solution, and 1.5 equivalents of aqueous cesium carbonate solution were added, and the mixture was irradiated with light from a 365 nm LED at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was dissolved in a solvent and filtered again. The resulting filtrate was concentrated and purified again by reprecipitation. As a result, -C accounted for 4 mol% of all benzene rings. ４ F ８ -group was introduced to obtain the target polymer (54) (M ｎ = 1.5 x 10 ４ , M ｗ / M ｎ = 3.9) was obtained in an isolated yield of 80%. Spectrum of compound 54 1 H NMR (400 MHz, CDCl3) δ 7.26-7.15 (m), 1.68 (s) 19 F NMR (376 MHz, CDCl3) δ -103.07 (br), 134.73 (br)

[0375] Example 31 Diamine compound (55) (0.4 mmol) was dissolved in CH ３ CN / H ２ To a mixed solution of 10 mL / 2 mL of iodine, 6 equivalents of perfluoropropyl iodide (2), 10 mol% eosin Y, 4 equivalents of ascorbic acid, and 2.5 equivalents of cesium carbonate were added, and the mixture was irradiated with a white LED and stirred for 24 hours. The resulting reaction mixture was purified by column chromatography to give mono-substituted 56, di-substituted 57, and tri-substituted 58 in isolated yields of 16%, 18%, and 5%, respectively. 1 H NMR (400 MHz, CDCl3) δ 7.11 (s, 1H), 7.08 (d, 1H, J = 8.24 Hz), 6.93 (d, 2H, J = 8.7 Hz), 6.64-6.61 (m, 3H), 3.78 (s, 2H) 19 F NMR (376 MHz, CDCl3) δ -80.61 (s, 3F), -109.87 (s, 2F), -126.86 (s, 2F) 1 H NMR (400 MHz, CDCl3) δ 7.08 (s, 2H), 7.06 (d, 2H, J = 8.2 Hz), 6.65 (d, 2H, 8.4 Hz), 4.13 (s, 4H), 3.79 (s, 2H) 19 F NMR (376 MHz, CDCl3) δ -80.70 (s, 3F), -110.02 (s, 2F), -126.98 (s, 2F) 1 H NMR (400 MHz, CDCl3) δ 7.28 (s, 2H), 7.06-7.04 (m, 2H), 6.67 (d, 1H, J = 8.7 Hz), 4.80 (s, 2H), 4.17 (s, 2H), 3.82 (s, 2H) 19 F NMR (376 MHz, CDCl3) δ -80.73 (s, 6F), -80.80 (s, 3F), -109.13 (s, 4F), -110.17 (s, 2F), -126.61 (s, 4F), -127.14 (s, 2F)

[0376] Example 32 Diamine compound (59) (0.2 mmol) was dissolved in CH ３ To CN (3 mL), 3 equivalents of perfluoropropyl iodide, 3 equivalents of 1,8-diazabicyclo[5.4.0]7-undecene (DBU), and 1.5 equivalents of potassium phosphate were added, and the mixture was irradiated with a white LED and stirred for 24 hours. The resulting reaction mixture was purified by column chromatography to give compound (60) in an isolated yield of 31%. Spectrum of Compound 60 1 H NMR (400 MHz, CDCl3) δ 6.74 (dd, 1H, J = 8.7, 2.8 Hz), 6.68 (d, 1H, J = 2.3 Hz), 6.61 (d, 1H, J = 8.7 Hz), 3.55 (s, 4H) 19 F NMR (376 MHz, CDCl3) δ -80.64 (s, 3F), -109.90 (s, 2F), -126.74 (s, 2F)

[0377] Example 33: Under an argon atmosphere, p-dihydroxybenzene (61) (0.2 mmol) was dissolved in CH ３ CN / H ２ To a 7.5 mL / 1.5 mL mixed solvent, 4.5 equivalents of perfluorohexyl iodide, 10 mol% of phloxine B, 2 equivalents of sodium ascorbate, and 1 equivalent of cesium carbonate were added, and the mixture was irradiated with a white LED and stirred for 24 hours. The resulting reaction mixture was purified by column chromatography to give compound (62) in an isolated yield of 47%. Spectra of compound 62a: 1H NMR (400 MHz, CDCl3): δ = 6.96 (dd, 1H, J = 9.16), 6.88 (m, 2H), 5.34 (t, 1H), 4.87 (s, 1H). 19F NMR (376 MHz, CDCl3): δ = δ -81.2 (s, 3F), -109.0 (s, 2F), -122.3 (s, 4F), -123.2 (s, 2F), -126.2. Spectra of compound 62b: 1H NMR (400 MHz, CDCl3): δ = δ 7.17 (s, 2H), 5.85 (t, 1H), 5.33 (s, 1H). 19F NMR (376 MHz, CDCl3): δ = δ -81.3 (s, 3F), -108.5 (s, 2F), -122.9 (s, 2F), -122.3 (s, 2F), -123.2 (s, 2F), -126.6 (s, 2F)

[0378] (Example 34) Polysulfone (63) (total repeating unit amount: 0.5 mmol) (M ｎ = 1.9 x 10 ４ , M ｎ / M ｎTo a dichloromethane solution (5 mL) of 1 equivalent of perfluoropropyl iodide, 3 equivalents (1 mL) of aqueous sodium thiosulfate solution, and 1.5 equivalents (1 mL) of aqueous cesium carbonate solution were added, and the mixture was irradiated with 365 nm LED light and stirred at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was dissolved in a solvent and filtered again. The resulting filtrate was concentrated and purified again by reprecipitation. As a result, 56 mol% of all repeating units contained C. ３ F ７ The target polymer (64) (M ｎ = 2.7 x 10 ４ , M ｗ / M ｎ = 3.11) was obtained in an isolated yield of 99%. Spectrum of compound 64 1 H NMR (400MHz, CDCl3): δ= 8.16 (br), 7.90 - 6.93 (br), 1.75 - 1.67 (br). 19 F NMR (471MHz, CDCl3) :δ= -80.6 - -80.9 (3F, br), -109.5 - -109.7 (2F, br), -125.7 - -126.4 (2F, br).

[0379] (Example 35) Polysulfone (63) (total repeating unit amount: 0.5 mmol) (M ｎ = 1.9 x 10 ４ , M ｎ / M ｎ To a dichloromethane solution (5 mL) of 1,2-dimethyl-2,4-trimethyl-1,4-trimethyl ... ６ F １３ The target polymer (65) (M ｎ= 2.3 x 10 ４ , M ｗ / M ｎ The resulting polymer was subjected to an evaluation of its water and oil repellency, revealing a water contact angle of 101° and an oil contact angle (using dodecane as the oil) of 32°. Spectrum of compound 65 1 H NMR (400MHz, CDCl3): δ= 8.19 (br), 7.93 - 7.85 (br), 7.29 - 7.22 (br), 7.04 - 6.94 (br), 1.72 - 1.70 (br). 19 F NMR (471MHz, CDCl3) :δ= -81.2 (3F, br), -108.6 - -108.8 (2F, br), -121.3 - -121.8 (2F, br), -122.2 (2F, br), -123.2 (2F, br), -126.6 (2F, br).

[0380] (Comparative Example 1) Polysulfone (63) (total repeating unit amount: 0.5 mmol) (M ｎ = 1.9 x 10 ４ , M ｎ / M ｎ To a dichloromethane solution (5 mL) of CF4 (HCO3 = 3.96), 20 equivalents of trifluoromethyl iodide, 3 equivalents (1 mL) of aqueous sodium thiosulfate solution, and 1.5 equivalents (1 mL) of aqueous cesium carbonate solution were added, and the mixture was irradiated with 365 nm LED light and stirred at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid fraction obtained by filtration was dissolved in a solvent and filtered again. The resulting filtrate was concentrated and purified again by reprecipitation. As a result, CF4 accounted for 11 mol% of all repeating units. ３ The target polymer (66) (M ｎ = 1.7 x 10 ４ , M ｗ / M ｎ = 4.01) was obtained in an isolated yield of 62%. The resulting polymer was then evaluated for water and oil repellency, revealing a water-resistant contact angle of 91° and an oil-resistant contact angle (using dodecane as the oil) of 7°.

[0381] (Example 36) Polyethersulfone (67) (total repeating unit amount: 0.5 mmol) (M ｎ = 5.6 x 10 ４ , M ｎ / M ｎ To a dichloromethane solution (5 mL) of 1,2-dimethyl-3-(2-methyl-2-propanol) (C = 2.20), 1 equivalent of perfluoropropyl iodide, 3 equivalents (1 mL) of aqueous sodium thiosulfate solution, and 1.5 equivalents (1 mL) of aqueous cesium carbonate solution were added, and the mixture was irradiated with light from a 365 nm LED at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was dissolved in a solvent and filtered again. The resulting filtrate was concentrated and then purified again by reprecipitation. As a result, 15 mol % of all repeating units contained C. ３ F ７ The target polymer (68) (M ｎ = 5.8 x 10 ４ , M ｗ / M ｎ = 1.58) was obtained in an isolated yield of 77%. Spectrum of compound 68 1 H NMR (400MHz, CDCl3): δ= 8.08 - 7.97 (br), 7.38 - 7.25 (br). 19 F NMR (471MHz, CDCl3) :δ= -79.3 (3F, br), -108.0 (2F, br), -124.7 (2F, br).

[0382] (Example 37) Epoxy resin (69) (total amount of repeating units: 1.0 mmol) (M ｎ = 3.6 x 10 ２ , M ｎ / M ｎTo a dichloromethane solution (5 mL) of 1,2-dimethyl-2,4-dichloro ... ３ F ７ The target polymer (70) (M ｎ = 7.5 x 10 ３ , M ｗ / M ｎ = 3.89) was obtained in an isolated yield of 10%. Spectrum of compound 70 1 H NMR (400MHz, CDCl3): δ= 7.04 - 6.75 (br), 4.17 - 1.63 (br) 19 F NMR (471MHz, CDCl3) :δ= -80.5 (3F, br), -80.8 (3F, br), -98.6 (2F, br), -124.3 (2F, br).

[0383] (Example 38) In the atmosphere, epoxy resin (71) (total amount of repeating units: 1.0 mmol) (M ｎ = 5.7 x 10 ２ , M ｎ / M ｎ To a dichloromethane solution (5 mL) of 12.7 (C = 12.7), 1 equivalent of perfluoropropyl iodide, 3 equivalents (1 mL) of aqueous sodium thiosulfate solution, and 1.5 equivalents (1 mL) of aqueous cesium carbonate solution were added, and the mixture was irradiated with light from a 365 nm LED at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was dissolved in the solution and filtered again. The resulting filtrate was concentrated and purified again by reprecipitation. As a result, 198 mol% of all repeating units contained C. ３ F ７ The target polymer (72) (M ｎ = 3.1 x 10 ２ , Mｗ / M ｎ = 147) was obtained in 50% isolated yield. Spectrum of compound 72 1 H NMR (400MHz, CDCl3): δ= 7.99 (br), 7.37 - 6.69 (br), 4.64 (br), 4.34 (br), 4.16 (br), 4.12 (br), 3.95 (br), 3.45 (br), 3.40 (br), 3.32 (br), 3.24 (br) 2.97 (br), 2.91 (br), 2.85 (br), 2.74 (br), 2.66 (br), 2.57 (br), 2.33 - 2.06 (br), 1.63 (br), 1.47 (br). 19 F NMR (471MHz, CDCl3) :δ= -80.8 (3F, br), -83.3 (3F, br), -109.0 (2F, br), -121.0 (2F, br), -126.4 (2F, br).

[0384] (Example 39) Under an argon atmosphere, 4.5 equivalents of perfluorohexyl iodide, 10 mol% Phloxine B, 2 equivalents of sodium ascorbate, and 1 equivalent of cesium carbonate were added to a dichloromethane solution (5 mL) of an acetonitrile / water (7.5 mL / 1.5 mL) mixed solvent of epoxy monomer (73), and the mixture was irradiated with white LED light at room temperature for 24 hours. The resulting reaction mixture was purified by column chromatography to obtain the target compound (74) in an isolated yield of 25%. Spectrum of compound 74 1 H NMR (400MHz, CDCl3): δ= 7.38 (s, 1H), 7.29 (dd, 1H, J = 8.47, 2.52), 7.12-7.07 (m, 2H), 6.91 (d, 1H, J = 8.70), 6.84-6.81 (m, 2H), 4.20 (tt, 1H), 4.09-4.04 (m, 1H), 3.98-3.93 (m, 2H), 3.36-3.30 (m, 2H), 2.91-2.88 (m, 2H), 2.78-2.74 (m, 2H) 19F NMR (471MHz, CDCl3) :δ= δ -81.3 (s, 3F), -108.2 (s, 2F), -121.7 (s, 2F), -122.3 (s, 2F), -123.2 (s, 2F), -126.6 (s, 2F)

[0385] (Example 40) In the atmosphere, 1 equivalent of perfluoropropyl iodide, 3 equivalents (1 mL) of aqueous sodium thiosulfate, and 1.5 equivalents (1 mL) of aqueous cesium carbonate were added to a dichloromethane solution (5 mL) of polyphenylene ether (75) (total amount of repeating units: 0.5 mmol), and the mixture was irradiated with light from a 365 nm LED at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was dissolved in a solvent and filtered again. The resulting filtrate was concentrated and purified again by reprecipitation. As a result, 8 mol% of all repeating units contained C. ３ F ７ The target polymer (76) (M ｎ = 2.4 x 10 ４ , M ｗ / M ｎ The resulting polymer (76) was readily soluble in tetrahydrofuran, whereas the starting polymer (71) was poorly soluble in tetrahydrofuran. This confirmed that the introduction of perfluoropropyl groups improved the solvent solubility. Spectrum of compound 76 1 H NMR (400MHz, CDCl3): δ= 6.49 (br), 2.13 (br), 0.88 - 0.79 (br). 19 F NMR (471MHz, CDCl3) : δ= -80.6 - -81.7 (3F, br), -102.2 - -102.6 (2F, br), -113.3 (2F, br), -125.0 - -125.2 (2F, br), -128.0 (2F, br).

[0386] (Example 41) Polymer (77) having a phenol skeleton (total amount of aromatic rings: 0.5 mmol) (M ｎ = 1.4 x 10 ２ , Mｎ / M ｎ To a dichloromethane solution (5 mL) of 1 equivalent of perfluoropropyl iodide, 3 equivalents (1 mL) of aqueous sodium thiosulfate solution, and 1.5 equivalents (1 mL) of aqueous cesium carbonate solution were added, and the mixture was irradiated with light from a 365 nm LED at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was dissolved in a solvent and filtered again. The resulting filtrate was concentrated and then purified again by reprecipitation. As a result, 26 mol% of all repeating units contained C. ３ F ７ The target polymer (78) (M ｎ = 2.4 x 10 ２ , M ｗ / M ｎ = 10.9) was obtained in an isolated yield of 99%. Spectrum of compound 78 1 H NMR (400MHz, CDCl3): δ= 6.99 (br), 6.92 (br), 6.88 (br), 4.85 (br), 4.69 (br), 3.40 (br), 2.95 (br), 2.90 (br), 2.77 (br), 2.66 (br), 2.31 (br), 2.20 (br), 1.82 (br), 1.79 (br), 1.61 (br), 1.44 (br), 1.28 (br), 0.76 (br). 19 F NMR (471MHz, CDCl3) : δ= -75.8 (3F, br), -80.9 (3F, br), -107.5 (2F, br), -108.9 (2F, br), -111.0 (2F, br), -115.0 (2F, br), -118.7 (2F, br), -121.2 (2F, br), -124.6 (2F, br), -125.9 (2F, br), -127.7 (2F, br).

[0387] (Example 42) Polyamideimide (79) (total repeating unit amount: 0.2 mmol) (M ｎ = 3.6 x 10 ４ , M ｎ / M ｎTo a DMF / dichloromethane / water (3 mL / 2 mL / 2 mL) mixed solution of 1.46 (C = 1.46), 5 equivalents of perfluoropropyl iodide, 3 equivalents (1 mL) of aqueous sodium thiosulfate solution, and 1.5 equivalents (1 mL) of aqueous cesium carbonate solution were added, and the mixture was irradiated with light from a 365 nm LED at room temperature for 72 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was filtered again. The resulting filtrate was concentrated and then purified again by reprecipitation. As a result, 13 mol % of all repeating units contained C. ３ F ７ The target polymer (80) (M ｎ = 3.1 x 10 ４ , M ｗ / M ｎ = 1.59) was obtained in an isolated yield of 43%.

[0388] Spectrum of compound 80 1 H NMR (400MHz, CDCl3): δ= 10.59 - 10.58 (br), 10.44 - 10.39 (br), 8.51 (br), 8.44 - 8.42 (br), 8.10 - 8.08 (br), 7.77 - 7.58 (br), 7.45 - 7.39 (br), 7.30 - 7.23 (br), 4.09 - 3.91 (br), 19 F NMR (471MHz, CDCl3) : δ= -79.1 - -81.72 (3F, br), -106.0 (2F, br), -110.9 (2F, br), -123.6 - -125.1 (2F, br).

[0389] (Example 43) Polyetherimide (24) (total repeating unit amount: 0.5 mmol) (M ｎ = 1.2 x 10 ４ , M ｎ / M ｎTo a dichloromethane solution (5 mL) of 1,2-difluoroisopropyl iodide, 3 equivalents (1 mL) of aqueous sodium thiosulfate, and 1.5 equivalents (1 mL) of aqueous cesium carbonate were added, and the mixture was irradiated with 365 nm LED light and stirred at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was dissolved in a solvent and filtered again. The resulting filtrate was concentrated and purified again by reprecipitation. As a result, 1 mol % of the total repeating units was ｉ C ３ F ７ The target polymer (81) (M ｎ = 1.8 x 10 ４ , M ｗ / M ｎ = 2.17) was obtained in an isolated yield of 90%. In the following formula, the units enclosed in parentheses with X, Y, and z may be present in any order. Polymer (82) was readily soluble in tetrahydrofuran and chloroform. Spectrum of compound 81 1 H NMR (400MHz, CDCl3): δ= 7.89 - 7.00 (br), 3.81 (br), 1.90 - 1.72 (br). 19 F NMR (471MHz, CDCl3) :δ= -74.1 - -74.9 (6F, br).

[0390] (Example 44) Polyetherimide (24) (total repeating unit amount: 0.5 mmol) (M ｎ = 1.2 x 10 ４ , M ｎ / M ｎ To a dichloromethane solution (5 mL) of 1-bromo-2-iodotetrafluoroethane (HCOOH = 1.64), 1 equivalent of 1-bromo-2-iodotetrafluoroethane, 3 equivalents (1 mL) of aqueous sodium thiosulfate solution, and 1.5 equivalents (1 mL) of aqueous cesium carbonate solution were added, and the mixture was irradiated with light from a 365 nm LED at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was dissolved in a solvent and filtered again. The resulting filtrate was concentrated and purified again by reprecipitation. As a result, 3 mol % of all repeating units contained BrC ２ F ４The target polymer (82) (M ｎ = 1.9 x 10 ４ , M ｗ / M ｎ = 2.11) was obtained in an isolated yield of 81%. In the following formula, the units enclosed in parentheses with X, Y, and z may be present in any order. Polymer (82) was readily soluble in tetrahydrofuran and chloroform. Spectrum of compound 82 1 H NMR (400MHz, CDCl3): δ= 7.89 - 7.02 (br), 3.82 (br), 1.75 - 1.73 (br). 19 F NMR (471MHz, CDCl3) :δ= -64.3 - -64.6 (2F, br), -105.1 - -105.6 (2F, br).

[0391] (Example 45) Polyetherimide (24) (total repeating unit amount: 0.5 mmol) (M ｎ = 1.2 x 10 ４ , M ｎ / M ｎ To a dichloromethane solution (5 mL) of (EtO(O)CF3) ... ２ The target polymer (83) (M ｎ = 2.0 × 10 ４ , M ｗ / M ｎ = 2.10) was obtained in an isolated yield of 92%. In the following formula, the units enclosed in parentheses with X, Y, and z may be present in any order. Polymer (83) was readily soluble in tetrahydrofuran and chloroform. Spectrum of compound 83 1H NMR (400MHz, CDCl3): δ= 7.89 - 7.00 (br), 4.33 - 4.19 (br), 3.82 (br), 1.75 - 1.73 (br), 1.28 - 1.25 (br). 19 F NMR (471MHz, CDCl3) :δ= -55.9 (2F, br), -96.1 (2F, br), -101.9 (2F, br), -103.4 (2F, br).

[0392] (Example 46) Polyetherimide (24) (total repeating unit amount: 0.5 mmol) (M ｎ = 1.2 x 10 ４ , M ｎ / M ｎ To a dichloromethane solution (5 mL) of iodine compound (M = 1.64), 1 equivalent of iodine compound, 3 equivalents (1 mL) of aqueous sodium thiosulfate solution, and 1.5 equivalents (1 mL) of aqueous cesium carbonate solution were added, and the mixture was irradiated with light from a 365 nm LED at room temperature for 24 hours. The resulting reaction mixture was reprecipitated, and the solid obtained by filtration was dissolved in a solvent and filtered again. The resulting filtrate was concentrated and purified again by reprecipitation. As a result, the target polymer (84) (M ｎ = 1.7 x 10 ４ , M ｗ / M ｎ = 2.09) was obtained in an isolated yield of 88%. In the following formula, the units enclosed in parentheses with X, Y, and z may be present in any order. Polymer (84) was readily soluble in tetrahydrofuran and chloroform. Spectrum of compound 84 1 H NMR (400MHz, CDCl3): δ= 7.89 - 7.02 (br), 3.83 (br), 1.75 - 1.73 (br). 19 F NMR (471MHz, CDCl3) :δ= -80.4 (3F, br), -83.5 (4F, br), -87.1 (3F, br), -89.0 (2F, br).

[0393] (Example 47) Polyetherimide (24) (total repeating unit amount: 0.5 mmol) (M ｎ = 1.2 x 10 ４ , M ｎ / M ｎ To a dichloromethane solution (5 mL) of 1,2-dimethyl-3,4-trimethyl-2,4-trimethyl-1 ... ｎ = 9.8 x 10 ３ , M ｗ / M ｎ = 3.92) was obtained in an isolated yield of 10%. In the following formula, the units enclosed in parentheses with X, Y, and z may be present in any order. Polymer (85) was readily soluble in tetrahydrofuran and chloroform. Spectrum of compound 85 1 H NMR (400MHz, CDCl3): δ= 7.90-7.01 (br), 7.42-7.32(br), 6.47(s), 2.09(s), 1.75(br), 1.25 (br) 19 F NMR (471MHz, CDCl3) :δ= -108.5 (2F, br), -111.1 (2F, br), -121.8 (4F, br), -122.2 (4F, br)

[0394] Comparative Example 2 Polyimide was synthesized using 4,4'-oxydianiline 15, which does not have a perfluoroalkyl group on the aromatic ring. Under an argon atmosphere, 1 equivalent of 6FDA was added to a DMF (50 wt%) solution of 4,4'-oxydianiline (15, 0.5 mmol), and the mixture was stirred at 180°C for 2.5 hours. After the reaction was completed, the resulting polyimide 86 was poorly soluble in DMF and precipitated. Polyimide 86 was also poorly soluble in tetrahydrofuran.

Claims

1. The following formula (I): 【Chemistry 1】 [In formula (I), A independently at each occurrence represents an aliphatic or aromatic imido-diyl group; Ar independently at each occurrence has the following formula (Ar1): 【Chemistry 2】 [In formula (Ar1), Ar 11 represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; Ar 12 independently in each occurrence represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; X 10 represents a single bond, —O—, —CO—, —SO 2 — or a branched C 2-4 alkylene group; n11 represents an integer of 0 to 3, * represents a bond, The total number of carbon atoms in formula (Ar1) is 6 or more and 20 or less. represents a group represented by L is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of R １ C, which may have one or more substituents, independently at each occurrence, １－１６ An alkylene group and a C group which may have one or more substituents ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, R ２ C, which may have one or more substituents, independently at each occurrence, １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, k independently in each occurrence represents an integer from 0 to 4, l independently in each occurrence represents an integer of 1 to 4; m independently in each occurrence represents an integer of 0 to 4; n represents an integer of 1 or more; In the unit enclosed in parentheses with n, the units enclosed in parentheses with k, l, and m may appear in any order; The following (i) and (ii): (i) k is 0 and in formula (I) there is one or more C ２－２０ Having a fluorine-containing organic group; (ii) k is 1 or more and 4 or less, and one or more C １－２０ Having a fluorine-containing organic group; Either of the following is satisfied.] The fluorine-containing aromatic polymer is represented by the formula:

2. Said C ２－２０ The fluorine-containing organic group is represented by the following formula (1A) and formula (1B): R ３１ -X １ -(R Ｆ１ ) ｒ -CF ２ -* (1A) *-X ３ -CF ２ -* (1B) [In formula (1A) and formula (1B), R Ｆ１ is -(Rf) ｐ -R Ｆ - (O) ｑ - represents Rf, at each occurrence, is independently a C optionally substituted by one or more fluorine atoms. １－１６ represents an alkylene group, R Ｆ represents a divalent fluoro(poly)ether group, X １ C which may be substituted by one or more halogen atoms １－１６ represents an alkylene group or a single bond, X ３ C which may be substituted by one or more halogen atoms １－１６ represents an alkylene group, R ３１ C which may be substituted by one or more halogen atoms １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C which may be substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, R ｆ３ C which may be substituted by one or more halogen atoms １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom, R ｆ４ represents, independently at each occurrence, a hydrogen atom or a fluorine atom; p is 0 or 1, q is 0 or 1, and r is 0 or 1; * represents a bond, The number of carbon atoms contained in formula (1A) or formula (1B) is 2 or more and 20 or less. is one or more groups selected from Said C １－２０ The fluorine-containing organic group is represented by the following formula (2A) and formula (2B): R ３２ -X １ -(R Ｆ１ ) ｒ -CF ２ -* (2A) *-X １ -CF ２ -* (2B) [In formula (2A) and formula (2B), R Ｆ１ is -(Rf) ｐ -R Ｆ - (O) ｑ - represents Rf, at each occurrence, is independently a C optionally substituted by one or more fluorine atoms. １－１６ represents an alkylene group, R Ｆ represents a divalent fluoro(poly)ether group, X １ C which may be substituted by one or more halogen atoms １－１６ represents an alkylene group or a single bond, R ３２ C which may be substituted by one or more halogen atoms １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C which may be substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, R ｆ３ C which may be substituted by one or more halogen atoms １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom, R ｆ４ represents, independently at each occurrence, a hydrogen atom or a fluorine atom; p is 0 or 1, q is 0 or 1, and r is 0 or 1; * represents a bond, The number of carbon atoms contained in formula (2A) or formula (2B) is 1 or more and 20 or less. The fluorine-containing aromatic polymer according to claim 1 , wherein the fluorine-containing aromatic polymer is a group represented by the formula:

3. Said C ２－２０ The fluorine-containing organic group is represented by the following formula (1-a), formula (1-b), formula (1-c), and formula (1B): F-X ３ -CF ２ -* (1-a) R ３１ -X １ -CF ２ -* (1-b) R ３１ -X １ -R Ｆ１ -CF ２ -* (1-c) *-X ３ -CF ２ -* (1B) [In the formula (1-a), the formula (1-b), the formula (1-c) and the formula (1B), R Ｆ１ is -(Rf) ｐ -R Ｆ - (O) ｑ - represents Rf, at each occurrence, is independently a C optionally substituted by one or more fluorine atoms. １－１６ represents an alkylene group, R Ｆ represents a divalent fluoro(poly)ether group, X １ C which may be substituted by one or more halogen atoms １－１６ represents an alkylene group or a single bond, X ３ C which may be substituted by one or more halogen atoms ３－１６ represents an alkylene group, R ３１ C which may be substituted by one or more halogen atoms １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom or a bromine atom; R ｆ２ each occurrence independently represents a C which may be substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, R ｆ３ C which may be substituted by one or more halogen atoms １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom, R ｆ４ represents, independently at each occurrence, a hydrogen atom or a fluorine atom; p is 0 or 1, q is 0 or 1, and r is 0 or 1; * represents a bond, The number of carbon atoms contained in formula (1-a) is 2 or more and 20 or less, The number of carbon atoms contained in formula (1-b) is 2 or more and 20 or less, The number of carbon atoms contained in formula (1-c) is 2 or more and 20 or less, The number of carbon atoms contained in formula (1B) is 2 or more and 20 or less. is a group selected from Said C １－２０ The fluorine-containing organic group is represented by the following formula (2-a), formula (2-b), formula (2-c), and formula (2B): F-X １ -CF ２ -* (2-a) R ３２ -X １ -CF ２ -* (2-b) R ３２ -X １ -R Ｆ１ -CF ２ -* (2-c) *-X １ -CF ２ -* (2B) [In formula (2-a), formula (2-b), formula (2-c) and formula (2B), R Ｆ１ is -(Rf) ｐ -R Ｆ - (O) ｑ - represents Rf, at each occurrence, is independently a C optionally substituted by one or more fluorine atoms. １－１６ represents an alkylene group, R Ｆ represents a divalent fluoro(poly)ether group, X １ C which may be substituted by one or more halogen atoms １－１６ represents an alkylene group or a single bond, R ３２ C which may be substituted by one or more halogen atoms １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom or a bromine atom; R ｆ２ each occurrence independently represents a C which may be substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, R ｆ３ C which may be substituted by one or more halogen atoms １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom, R ｆ４ represents, independently at each occurrence, a hydrogen atom or a fluorine atom; p is 0 or 1, q is 0 or 1, and r is 0 or 1; * represents a bond, The number of carbon atoms contained in formula (2-a) is 1 or more and 20 or less, The number of carbon atoms contained in formula (2-b) is 1 or more and 20 or less, The number of carbon atoms contained in formula (2-c) is 1 or more and 20 or less, The number of carbon atoms contained in formula (2B) is 1 or more and 20 or less. The fluorine-containing aromatic polymer according to claim 1 , wherein the fluorine-containing aromatic polymer is a group selected from the group consisting of

4. The formula (I) is represented by the following formula (I-a): 【Chemistry 3】 [In formula (I-a), A ａ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ａ each occurrence independently represents a group represented by formula (Ar1); n a represents an integer of 1 or more; In the formula (I-a), one or more C １－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 1 , wherein

5. The above formula (I) is represented by the following formula (I-b): 【Chemistry 4】 [In formula (I-b), Ar ｂ each occurrence independently represents a group represented by formula (Ar1); L ｂ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of R １ each occurrence independently represents an optionally substituted C １－１６ An alkylene group and a C group which may have one or more substituents ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, R ２ C, which may have one or more substituents, independently at each occurrence, １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, nb represents an integer of 1 or more; In formula (I-b), one or more C ２－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 1 , wherein

6. The formula (I-b) is the following formula (I-b1), (I-b2), (I-b3), (I-b4), (I-b5), (I-b6) or (I-b7): 【Chemistry 5】 [In the formula (I-b1), (I-b2), (I-b3), (I-b4), (I-b5), (I-b6) or (I-b7), Ar ｂ each occurrence independently represents a group represented by formula (Ar1); nb represents an integer of 1 or more; In the formulae (I-b1), (I-b2), (I-b3), (I-b4), (I-b5), (I-b6) and (I-b7), each of them contains one or more C ２－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 5 , represented by the formula:

7. The above formula (I) is represented by the following formula (I-c): 【Chemistry 6】 [In formula (I-c), Ar ｃ１ each occurrence independently represents a group represented by formula (Ar1); Ar ｃ２ each occurrence independently represents a group represented by formula (Ar1); L ｃ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of L ｃ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of Ar ｃ１ and Ar ｃ２ and L ｃ１ and L ｃ２ In at least one of the combinations, one group is different from the other group, R １ each occurrence independently represents an optionally substituted C １－１６ An alkylene group and a C group which may have one or more substituents ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, R ２ C, which may have one or more substituents, independently at each occurrence, １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, n c represents an integer of 1 or more; In formula (I-c), one or more C ２－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 1 , wherein

8. The formula (I-c) is represented by the following formula (I-c1), (I-c2) or (I-c3): 【Chemistry 7】 [In formula (I-c1), (I-c2) or (I-c3), Ar ｃ１ each occurrence independently represents a group represented by formula (Ar1); Ar ｃ２ each occurrence independently represents a group represented by formula (Ar1); n c independently in each occurrence is an integer of 1 or greater; In the formulas (I-c1), (I-c2) and (I-c3), each of them contains one or more C ２－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 7 , represented by the formula:

9. The above formula (I) can be represented by the following formula (I-d): 【Chemistry 8】 [In formula (I-d), Ar ｄ１ each occurrence independently represents a group represented by formula (Ar1); Ar ｄ２ each occurrence independently represents a group represented by formula (Ar1); Ar ｄ３ each occurrence independently represents a group represented by formula (Ar1); L ｄ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of L ｄ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of L ｄ３ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of Ar ｄ１ , Ar ｄ２ and Ar ｄ３ and L ｄ１ , L ｄ２ and L ｄ３ In at least one of the combinations, one group is a group different from at least one of the other two groups, R １ C, which may have one or more substituents, independently at each occurrence, １－１６ An alkylene group and a C group which may have one or more substituents ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, R ２ C, which may have one or more substituents, independently at each occurrence, １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, nd represents an integer of 1 or more; In formula (I-d), one or more C ２－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 1 , wherein

10. The formula (I-d) is represented by the following formula (I-d1) or (I-d2): 【Chemistry 9】 [In formula (I-d1) or (I-d2), Ar ｄ１ each occurrence independently represents a group represented by formula (Ar1); Ar ｄ２ each occurrence independently represents a group represented by formula (Ar1); Ar ｄ３ each occurrence independently represents a group represented by formula (Ar1); nd independently in each occurrence represents an integer of 1 or greater; In the formulas (I-d1) and (I-d2), each of them contains one or more C ２－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 9 , represented by the formula:

11. The above formula (I) can be represented by the following formula (I-e): 【Chemistry 10】 [In formula (Ie), Ar ｅ１ each occurrence independently represents a group represented by formula (Ar1); L ｅ１ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of L ｅ２ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of L ｅ３ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of R １ C, which may have one or more substituents, independently at each occurrence, １－１６ An alkylene group and a C group which may have one or more substituents ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, R ２ C, which may have one or more substituents, independently at each occurrence, １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, ne represents an integer of 1 or more; In formula (I-e), one or more C ２－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 1 , wherein

12. The formula (I-e) is represented by the following formula (I-e1), (I-e2) or (I-e3): 【Chemistry 11】 [In formula (I-e1), (I-e2) or (I-e3), Ar ｅ１ each occurrence independently represents a group represented by formula (Ar1); R ７ C which may have one or more substituents １－１６ An alkylene group and a C group which may have one or more substituents ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, ne independently in each occurrence represents an integer of 1 or greater; In the formula (I-e1), (I-e2) or (I-e3), one or more C ２－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 11, represented by the formula:

13. The above formula (I) represents the following formula (I-g): 【Chemistry 12】 [In formula (Ig), Ar ｇ each occurrence independently represents a group represented by formula (Ar1); L ｇ１ C which may have one or more substituents ３－１６ represents a divalent group containing an alicyclic hydrocarbon group, mg, in each occurrence, independently represents an integer of 0 to 4; ng1 represents an integer of 1 or more; ng2 represents an integer of 1 or more; In the formula (I-g), one or more C ２－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 1 , wherein

14. The above formula (I) can be represented by the following formula (I-h): 【Chemistry 13】 [In formula (Ih), A ｈ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ｈ each occurrence independently represents a group represented by formula (Ar1); L ｈ is independently at each occurrence -R １ -, -O-, -S-, -NR ２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２ -CO- and CO-NR ２ - represents one selected from the group consisting of R １ each occurrence independently represents an optionally substituted C １－１６ An alkylene group and a C group which may have one or more substituents ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, R ２ C, which may have one or more substituents, independently at each occurrence, １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, nh represents an integer of 1 or more; In formula (I-h), one or more C １－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 1 , wherein

15. The above formula (I-h) can be represented by the following formula (I-h1): 【Chemistry 14】 [In formula (I-h1), A ｈ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ｈ each occurrence independently represents a group represented by formula (Ar1); nh independently in each occurrence represents an integer of 1 or greater; In the formula (I-h1), each of them has one or more C １－２０ It has a fluorine-containing organic group.] The fluorine-containing aromatic polymer according to claim 14 , wherein

16. A is represented by the following formula (A2-I): 【Chemistry 15】 [In formula (A2-I), A １０ represents a single bond or a divalent organic group, * represents a bond. Or the following formula (A2-II) 【Chemistry 16】 [In formula (A2-II), * represents a bond.] The fluorine-containing aromatic polymer according to claim 1 , wherein

17. A １０ is a single bond and formulas (a-1) to (a-7): 【Chemistry 17】 [In formulas (a-1) to (a-7), R ３ is C optionally substituted by a fluorine atom １－１６ represents an alkylene group, * represents a bond. The fluorine-containing aromatic polymer according to claim 16 , wherein the fluorine-containing aromatic polymer is one selected from groups represented by the following formula:

18. A is represented by the following formulas (A1-1) to (A1-19): 【Chemistry 18】 【Chemistry 19】 [In the formulas (A1-1) to (A1-19), * represents a bond.] The fluorine-containing aromatic polymer according to claim 14 , wherein the fluorine-containing aromatic polymer is one selected from groups represented by the following formula:

19. The following formula (I-1): 【Chemistry 20】 [In formula (I-1), A １ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar １ represents, independently at each occurrence, the following formula (Ar1): 【Chemistry 23】 [In formula (Ar1), Ar 11 represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; Ar 12 independently in each occurrence represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; X 10 represents a single bond, —O—, —CO—, —SO 2 — or a branched C 2-4 alkylene group; n11 represents an integer of 0 to 3, * represents a bond, The total number of carbon atoms in formula (Ar1) is 6 or more and 20 or less. represents a group represented by L １ is independently at each occurrence -R １１ -, -O-, -S-, -NR １２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR １２ -CO- and CO-NR １２ - represents one selected from the group consisting of R １１ each occurrence independently represents an optionally substituted C １－１６ An alkylene group and a C group which may have one or more substituents ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, R １２ each occurrence independently represents an optionally substituted C １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, k1, in each occurrence, independently represents an integer of 0 to 4; l1, in each occurrence, independently represents an integer of 1 to 4; m1, in each occurrence, independently represents an integer of 0 to 4; n1 represents an integer of 1 or more; In the unit enclosed in parentheses with n1, the units enclosed in parentheses with k1, l1, and m1 may appear in any order; In formula (I-1), one or more C １－２０ It has a fluorine-containing organic group.] A method for producing a fluorine-containing aromatic polymer represented by the formula: The following formula (I-2): 【Chemistry 21】 [In formula (I-2), A ２ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar ２ each occurrence independently represents a group represented by formula (Ar1); L is independently at each occurrence -R ２１ -, -O-, -S-, -NR ２２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR ２２ -CO- and CO-NR ２２ - represents one selected from the group consisting of R ２１ C, which may have one or more substituents, independently at each occurrence, １－１６ An alkylene group and a C group which may have one or more substituents ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, R ２２ C, which may have one or more substituents, independently at each occurrence, １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, k2, in each occurrence, independently represents an integer of 0 to 4; l2, in each occurrence, independently represents an integer of 1 to 4; m2, in each occurrence, independently represents an integer of 0 to 4; n2 represents an integer of 1 or more; In the unit enclosed in parentheses with n2, the units enclosed in parentheses with k2, l2 and m2 may appear in any order.] and an aromatic polymer represented by the following formula (II): I-R ｆ１ (II) [In formula (II), R ｆ１ is C １－２０ represents a fluorine-containing organic group. With a compound represented by the formula:

20. The following formula (I-1): 【Chemical 22】 [In formula (I-1), A １ represents, independently at each occurrence, an aliphatic or aromatic imido-diyl group; Ar １ represents, independently at each occurrence, the following formula (Ar1): 【Chemistry 23】 [In formula (Ar1), Ar 11 represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; Ar 12 independently in each occurrence represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; X 10 represents a single bond, —O—, —CO—, —SO 2 — or a branched C 2-4 alkylene group; n11 represents an integer of 0 to 3, * represents a bond, The total number of carbon atoms in formula (Ar1) is 6 or more and 20 or less. represents a group represented by L １ is independently at each occurrence -R １１ -, -O-, -S-, -NR １２ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO ２ --, --NR １２ -CO- and CO-NR １２ - represents one selected from the group consisting of R １１ each occurrence independently represents an optionally substituted C １－１６ An alkylene group and a C group which may have one or more substituents ３－１６ represents one kind selected from divalent groups containing an alicyclic hydrocarbon group, R １２ each occurrence independently represents an optionally substituted C １－１６ an alkyl group, optionally having one or more substituents; ６－２０ represents an aromatic hydrocarbon group or a hydrogen atom, k1, in each occurrence, independently represents an integer of 0 to 4; l1, in each occurrence, independently represents an integer of 1 to 4; m1, in each occurrence, independently represents an integer of 0 to 4; n1 represents an integer of 1 or more; In the unit enclosed in parentheses with n1, the units enclosed in parentheses with k1, l1, and m1 may appear in any order; and In the formula (I-1), one or more C １－２０ It has a fluorine-containing organic group.] A method for producing a fluorine-containing aromatic polymer represented by the formula: an aromatic monomer and a compound of the following formula (II): I-R ｆ１ (II) [In formula (II), R ｆ１ is C １－２０ represents a fluorine-containing organic group. to obtain a fluorine-containing aromatic monomer; and A production method comprising obtaining a fluorinated aromatic polymer by using the fluorinated aromatic monomer as a monomer.

21. The aromatic monomer has the formula (III): ( ４ ___ ３  ４ (_=) [In formula (III), Ar ３ each occurrence independently represents a group represented by formula (Ar1); R ４ is independently at each occurrence -OH, -NH ２ , a fluorine atom or a chlorine atom. The method according to claim 20 , wherein the formula is

22. The method according to claim 20, comprising reacting the fluorinated aromatic monomer with a second monomer to obtain a fluorinated aromatic polymer.

23. The method according to claim 22, wherein the second monomer is a monomer having, in one molecule, two or more groups capable of reacting with an amino group or a hydroxyl group.

24. The second monomer has the following formula (IV): R ５ -L １０ -R ５ (IV) [In formula (IV), R ５ each independently at each occurrence represent the following formulae (r-1) to (r-18): 【Chemistry 24】 【Chemistry 25】 [In formulas (r-1) to (r-18), * represents a bond.] represents one type selected from L １０ is represented by the following formulas (l-1) to (l-11): 【Chemistry 26】 【Chemical 27】 [In formulas (l-1) to (l-11), R ６ is a single bond, C optionally substituted by one or more fluorine atoms １－１６ An alkylene group or a divalent C group which may have one or more substituents. ６－２０ represents an aromatic hydrocarbon group, * represents a bond. represents one type selected from the following. The method according to claim 22, wherein the compound is represented by the formula:

25. The following formula (III-1): ( ４１ ___ ３１  ４１ (_). [In formula (III-1), Ar ３１ represents, independently at each occurrence, the following formula (Ar1): 【Chemistry 28】 [In formula (Ar1), Ar 11 represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; Ar 12 independently in each occurrence represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; X 10 represents a single bond, —O—, —CO—, —SO 2 — or a branched C 2-4 alkylene group; n11 represents an integer of 0 to 3, * represents a bond, The total number of carbon atoms in formula (Ar1) is 6 or more and 20 or less. R ４１ is independently at each occurrence -OH, -NH ２ , a glycidyloxy group, a fluorine atom or a chlorine atom, In the formula (III-1), one or more C １－２０ It has a fluorine-containing organic group.] It is expressed as Said C １－２０ The fluorine-containing organic group is represented by the following formula (2-1A) and formula (2B): R ３３ -X １ -(R Ｆ１ ) ｒ -CF ２ -* (2-1A) *-X １ -CF ２ -* (2B) [In formula (2-1A) and formula (2B), R Ｆ１ is -(Rf) ｐ -R Ｆ - (O) ｑ - represents Rf, at each occurrence, is independently a C optionally substituted by one or more fluorine atoms. １－１６ represents an alkylene group, R Ｆ represents a divalent fluoro(poly)ether group, X １ C which may be substituted by one or more halogen atoms １－１６ represents an alkylene group or a single bond, R ３３ C which may have one or more substituents ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ５ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C which may be substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, R ｆ３ C which may be substituted by one or more halogen atoms １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom, R ｆ４ represents, independently at each occurrence, a hydrogen atom or a fluorine atom; p is 0 or 1, q is 0 or 1, and r is 0 or 1; * represents a bond, The number of carbon atoms contained in formula (2-1A) is 1 or more and 20 or less, The number of carbon atoms contained in formula (2B) is 1 or more and 20 or less. Fluorine-containing aromatic monomers represented by one or more of the following:

26. The present invention includes a substrate and a layer formed on a surface of the substrate using a surface treatment agent, the substrate comprises an aromatic polymer; The surface treatment agent is represented by the following formula (II-1A) and formula (II-1B): R ３２ -X １ -(R Ｆ１ ) ｒ -CF ２ -I (II-1A) I-X １ -CF ２ -I (II-1B) [In formula (II-1A) and formula (II-1B), R Ｆ１ is -(Rf) ｐ -R Ｆ - (O) ｑ - represents Rf, at each occurrence, is independently a C optionally substituted by one or more fluorine atoms. １－１６ represents an alkylene group, R Ｆ represents a divalent fluoro(poly)ether group, X １ C which may be substituted by one or more halogen atoms １－１６ represents an alkylene group or a single bond, R ３２ C which may be substituted by one or more halogen atoms １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C which may be substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, R ｆ３ C which may be substituted by one or more halogen atoms １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom, R ｆ４ represents, independently at each occurrence, a hydrogen atom or a fluorine atom; p is 0 or 1, q is 0 or 1, and r is 0 or 1; * represents a bond, The number of carbon atoms contained in formula (II-1A) is 1 or more and 20 or less, The number of carbon atoms contained in formula (II-1B) is 1 or more and 20 or less.] The compound includes one or more compounds selected from the group consisting of The aromatic polymer has the following formula (I-2): 【Chemical 29】 [In formula (I-2), A 2 independently represents a divalent organic group which contains one or more imide rings and may have one or more substituents, Ar 2 is represented by the following formula (Ar1): 【Chemistry 30】 [In formula (Ar1), Ar 11 represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; Ar 12 independently in each occurrence represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; X 10 represents a single bond, —O—, —CO—, —SO 2 — or a branched C 2-4 alkylene group; n11 represents an integer of 0 to 3, * represents a bond, The total number of carbon atoms in formula (Ar1) is 6 or more and 20 or less. represents a group represented by L 2 in each occurrence independently represents one member selected from the group consisting of -R 1 -, -O-, -S-, -NR 2 -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO 2 -, -NR 2 -CO- and CO-NR 2 -; R 1 , in each occurrence, independently represents one member selected from a divalent group containing a C 1-16 alkylene group which may have a substituent, and a C 3-16 alicyclic hydrocarbon group which may have one or more substituents; R 2 independently represents an optionally substituted C 1-16 alkyl group or a hydrogen atom in each occurrence; k2, in each occurrence, independently represents an integer of 0 to 4; l2, in each occurrence, independently represents an integer of 1 to 4; m2, in each occurrence, independently represents an integer of 0 to 4; n2 represents an integer of 1 or more; In the unit enclosed in parentheses with n, the units enclosed in parentheses with k2, l2, and m2 may appear in any order. An item, represented by

27. reacting the substrate with a surface treatment agent to form a layer on the surface of the substrate; the substrate comprises an aromatic polymer; The surface treatment agent is represented by the following formula (II-1A) and formula (II-1B): R ３２ -X １ -(R Ｆ１ ) ｒ -CF ２ -I (II-1A) I-X １ -CF ２ -I (II-1B) [In formula (II-1A) and formula (II-1B), R Ｆ１ is -(Rf) ｐ -R Ｆ - (O) ｑ - represents Rf, at each occurrence, is independently a C optionally substituted by one or more fluorine atoms. １－１６ represents an alkylene group, R Ｆ represents a divalent fluoro(poly)ether group, X １ C which may be substituted by one or more halogen atoms １－１６ represents an alkylene group or a single bond, R ３２ C which may be substituted by one or more halogen atoms １－１６ an alkyl group, optionally having one or more substituents; ６－２０ an aromatic hydrocarbon group, a silsesquioxane residue which may have one or more substituents, -COOR ｆ２ , -OR ｆ２ , -SO ２ R ｆ３ , -CR ｆ４ =CR ｆ４ ２ , a fluorine atom, a bromine atom, or an iodine atom; R ｆ２ each occurrence independently represents a C which may be substituted by one or more fluorine atoms; １－１６ represents an alkyl group or a hydrogen atom, R ｆ３ C which may be substituted by one or more halogen atoms １－１６ represents an alkyl group, a fluorine atom, or a hydrogen atom, R ｆ４ represents, independently at each occurrence, a hydrogen atom or a fluorine atom; p is 0 or 1, q is 0 or 1, and r is 0 or 1; * represents a bond, The number of carbon atoms contained in formula (II-1A) is 1 or more and 20 or less, The number of carbon atoms contained in formula (II-1B) is 1 or more and 20 or less.] The compound includes one or more compounds selected from the group consisting of fruit, The aromatic polymer has the following formula (I-2): 【Chemistry 31】 [In formula (I-2), A 2 independently represents a divalent organic group which contains one or more imide rings and may have one or more substituents, Ar 2 is represented by the following formula (Ar1): 【Chemistry 32】 [In formula (Ar1), Ar 11 represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; Ar 12 independently in each occurrence represents a divalent C 6-10 aromatic hydrocarbon group which may have one or more substituents; X 10 represents a single bond, —O—, —CO—, —SO 2 — or a branched C 2-4 alkylene group; n11 represents an integer of 0 to 3, * represents a bond, The total number of carbon atoms in formula (Ar1) is 6 or more and 20 or less. represents a group represented by L 2 in each occurrence independently represents one member selected from the group consisting of -R 1 -, -O-, -S-, -NR 2 -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -SO 2 -, -NR 2 -CO- and CO-NR 2 -; R 1 , in each occurrence, independently represents one member selected from a divalent group containing a C 1-16 alkylene group which may have a substituent, and a C 3-16 alicyclic hydrocarbon group which may have one or more substituents; R 2 independently represents an optionally substituted C 1-16 alkyl group or a hydrogen atom in each occurrence; k2, in each occurrence, independently represents an integer of 0 to 4; l2, in each occurrence, independently represents an integer of 1 to 4; m2, in each occurrence, independently represents an integer of 0 to 4; n2 represents an integer of 1 or more; In the unit enclosed in parentheses with n, the units enclosed in parentheses with k2, l2, and m2 may appear in any order. A method for manufacturing an article, represented by the formula:

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