Compound, conductive film, photoelectronic device, and method for producing conductive film

Abstract

A compound has a molecular weight of 500 to 5,000 and is composed of a hydrogen atom, a carbon atom, and a hetero atom. The hetero atom is at least one selected from an oxygen atom, a sulfur atom, a fluorine atom, and a silicon atom, and has one or more alicyclic structures, one or more aromatic ring structures directly bonded to the alicyclic structures, and one or more monovalent substituents Ms directly bonded to the aromatic ring structures. The monovalent substituent Ms is at least one substituent selected from a group containing a monovalent fluorine-containing aliphatic group, a group containing a monovalent sulfur fluoride-containing group, a group containing a monovalent siloxanyl group, and a group containing a monovalent saturated hydrocarbon group.

Description

Compound, conductive film, photoelectron device, and method for producing conductive film

[0001] This disclosure relates to a compound, a conductive film, a photoelectron device, and a method for manufacturing a conductive film. This application claims priority to Japanese Patent Application No. 2023-220240, filed on December 27, 2023, the contents of which are incorporated herein by reference.

[0002] Conventionally, a conductive film having two regions with different light transmittances has been known as a conductive film included in an optoelectronic device such as an organic electroluminescence device (hereinafter also referred to as an "organic EL device"). In the following description, the region with the relatively low light transmittance may be referred to as a "first region" and the region with the relatively high light transmittance may be referred to as a "second region."

[0003] In recent years, a method using an organic material with metal-repellent properties (hereinafter also referred to as "metal patterning material") has become known as a method for manufacturing such conductive films. In this method, a pattern film is formed on a substrate using a metal patterning material, and then a metal is vapor-deposited on top of the pattern film. At this time, in the region where the pattern film is formed, no metal is deposited or only a small amount of metal is deposited, forming a second region with high light transmittance. On the other hand, in the region where the pattern film is not formed, a large amount of metal is deposited, forming a first region with relatively low light transmittance.

[0004] Patent Document 1 discloses, as a vapor-depositable metal patterning material, a compound having a specific aromatic ring and / or heteroaromatic ring, a fluorine atom, and at least one tertiary amine in the molecule, not having a fused aromatic ring having 16 or more carbon atoms, having a molecular weight of 500 to 3,000, and having a glass transition temperature of 60°C or higher.

[0005] International Publication No. 2022 / 034907

[0006] However, the compound described in Patent Document 1 may not have sufficient silver (Ag) repellency. For example, when Ag is vapor-deposited onto a pattern film formed from the compound described in Patent Document 1, Ag may adhere to the surface of the pattern film, and even if the second region appears transparent, the visible light transmittance, particularly the blue light transmittance, may become lower than before the Ag vapor deposition.

[0007] The present disclosure provides a compound having excellent Ag repellency, a conductive film using the same, a photoelectron device, and a method for producing the conductive film.

[0008] The present disclosure provides a compound, a conductive film, a photoelectron device, and a method for producing a conductive film, each having the following structures [1] to

[12] . [1] A compound having a molecular weight of 500 to 5,000, and consisting of hydrogen atoms, carbon atoms, and heteroatoms, wherein the heteroatoms are at least one selected from oxygen atoms, sulfur atoms, fluorine atoms, and silicon atoms, and having one or more alicyclic structures, one or more aromatic ring structures directly bonded to the alicyclic structures, and one or more monovalent substituents Ms directly bonded to the aromatic ring structures, wherein the monovalent substituents Ms are at least one selected from a group containing a monovalent fluorinated aliphatic group, a group containing a monovalent sulfur-containing fluorinated group, a group containing a monovalent siloxanyl group, and a group containing a monovalent saturated hydrocarbon group. [2] The compound of [1] above, wherein the number of the alicyclic structures is two or more. [3] The compound of [1] or [2] above, wherein the alicyclic structure is monocyclic. [4] The compound according to any one of [1] to [3] above, wherein the group containing the monovalent fluorine-containing aliphatic group is represented by the following formula f1: １ - (OR １ ) ｎ -F Formula f1 where R １ is an alkylene group or a fluoroalkylene group, n is an integer of 1 or more, and n R １ may be the same or different, Z １ is a single bond or a divalent linking group not containing an aromatic ring structure. [5] The compound according to any one of [1] to [3] above, wherein the group containing the monovalent fluorine-containing aliphatic group is at least one selected from the groups represented by the following formulae f5 and f6: ２ (-X １ -Rf １ )n1 Formula f5 -Z ３ (-X ２ -Rf ２ -R ２ ) ｎ２　　　　　　 Formula f6 where Rf １ is -CF ３ , -CF２ H or -CFH ２ and Rf ２ Ha-CF ２ - or -CFH-, and R ２ is an alkyl group, and X １ is —O— or —S—, and Z ２ and Z ３ is a single bond or an (n1+1)-valent or (n2+1)-valent linking group not containing an aromatic ring structure, and n1 and n2 are integers of 1 to 9. [6] The compound according to any one of [1] to [3] above, wherein the group containing the monovalent fluorinated sulfur group is at least one selected from groups represented by the following formulae fs1 and fs2: ４ -SF ５ Formula fs1 -Z ５ -SF ４ -R ３ Formula fs2 where R ３ is a hydrocarbon group, and Z ４ and Z ５ is a single bond or a divalent linking group not containing an aromatic ring structure. [7] The compound according to any one of [1] to [3] above, wherein the group containing a monovalent siloxanyl group is at least one selected from groups represented by the following formulae sx1 and sx2: However, R ４ are each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms, and Z ６ represents a single bond or a divalent linking group that does not contain an aromatic ring structure, and a, b, c, and d are each independently an integer of 0 to 20, and satisfy a+b+c+d>0. However, R ５ are each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms, and Z ７ is a divalent linking group that does not contain a single bond or an aromatic ring structure, e is an integer of 1 to 20, f is an integer of 0 to 20, and e+f>1 is satisfied. [8] The compound according to any one of the above [1] to [3], wherein the group containing a monovalent saturated hydrocarbon group is represented by the following formula sh1: -Z ８ -R ６　　　　　　　 Formula sh1 where R ６is a saturated hydrocarbon group having 4 to 24 carbon atoms, and Z ８ is a single bond, a divalent linking group not containing an aromatic ring structure, an oxygen atom, or a sulfur atom. [9] The compound according to any one of [1] to [8] above, which is represented by the following formula 1: wherein m is an integer of 1 to 8, A is an m-valent group containing one or more of the alicyclic structures, and Y １ ~Y ５ are each independently the monovalent substituent Ms, a hydrogen atom, a fluorine atom, or a monovalent aliphatic group not having a fluorine atom (excluding groups containing the monovalent saturated hydrocarbon group), and Y １ and Y ２ , Y ２ and Y ３ , Y ３ and Y ４ , Y ４ and Y ５ One or two of the combinations of may be bonded to each other to form a ring together with the carbon atoms to which they are bonded, and Y １ ~Y ５ At least one of the groups represented by Y is the monovalent substituent Ms. １ ~Y ５

[11] The compound according to

[10] or

[11] , wherein m in formula 1 is 2 and A is a group represented by the following formula A-1, or m in formula 1 is 3 and A is a group represented by the following formula A-2, or m in formula 1 is 4 and A is a group represented by the following formula A-3. However, Z ９is a single bond or a divalent linking group not containing an aromatic ring structure. *- represents a bond.

[12] A conductive film having a first region and a second region exhibiting higher light transmittance than the first region, the conductive film comprising: a first film containing a conductive material; and a second film containing a compound of any one of [1] to

[11] , wherein the first film is disposed so as to overlap at least the first region of the first region and the second region, and the second film is disposed so as to overlap the second region.

[13] The conductive film according to

[12] , wherein the conductive material contains silver.

[14] An optoelectronic device having the conductive film of

[12] or

[13] .

[15] The optoelectronic device according to

[14] , comprising: a substrate; an anode provided on the substrate; a cathode provided on the substrate; and an active layer disposed between the anode and the cathode, wherein the cathode is the conductive film.

[16] A method for producing a conductive film, comprising: depositing a compound of any one of [1] to

[11] on a substrate through a mask to form a second film containing the compound; and depositing a conductive material on the second film.

[17] The method for producing a conductive film according to

[16] , wherein the conductive material contains silver.

[0009] The compound of the present disclosure has excellent Ag repellency.

[0010] FIG. 1 is a plan view of a conductive film 1 according to an embodiment; FIG. 2 is a cross-sectional view taken along line II-II in FIG. 1; FIG. 3 is a schematic diagram showing a method for manufacturing a conductive film 1; FIG. 4 is a schematic diagram showing a method for manufacturing a conductive film 1; FIG. 5 is a schematic diagram showing a method for manufacturing a conductive film 1; FIG. 6 is a schematic diagram showing a conductive film 2 according to an embodiment; FIG. 7 is a schematic diagram showing a conductive film 3 according to an embodiment; FIG. 8 is a cross-sectional schematic diagram showing an optoelectronic device (organic EL device) according to an embodiment; FIG. 9 is a transmittance spectrum at wavelengths of 300 to 800 nm in Example 1; FIG. 10 is a transmittance spectrum at wavelengths of 300 to 800 nm in Example 2; FIG. 11 is a transmittance spectrum at wavelengths of 300 to 800 nm in Example 3; FIG. 12 is a transmittance spectrum at wavelengths of 300 to 800 nm in Example 4; FIG. 13 is a transmittance spectrum at wavelengths of 300 to 800 nm in Example 21; FIG. 14 is a transmittance spectrum at wavelengths of 300 to 800 nm in Example 22; FIG. 15 is a transmittance spectrum at wavelengths of 300 to 800 nm in Example 23; FIG. 16 is a transmittance spectrum at wavelengths of 300 to 800 nm in Example 24. 10 is a transmittance spectrum in Example 25 at wavelengths of 300 to 800 nm.

[0011] The meanings and definitions of terms used in this specification are as follows. An "alkylene group" refers to a divalent saturated hydrocarbon group. A "fluoroalkylene group" refers to a group in which one or more hydrogen atoms of an alkylene group have been substituted with a fluorine atom. A "polyfluoroalkylene group" refers to a group in which two or more hydrogen atoms of an alkylene group have been substituted with a fluorine atom. A "perfluoroalkylene group" refers to a group in which all hydrogen atoms of an alkylene group have been substituted with a fluorine atom. An "alkyl group" refers to a monovalent saturated hydrocarbon group. An "ethereal oxygen atom" refers to an oxygen atom that forms an ether bond (-O-) between carbon and carbon atoms. In this specification, compounds or groups represented by chemical formulas will also be referred to as compounds or groups with the number of the formula. For example, a compound represented by Formula 1 will also be referred to as Compound 1, and a group represented by Formula f1 will also be referred to as Group f1. In this specification, the symbol "to" indicating a range of values ​​means that the values ​​before and after it are included as the lower and upper limits. In addition, in FIGS. 1 to 8, the dimensions and proportions of each component are appropriately changed to make the drawings easier to understand.

[0012] [Compound] The compound of the present disclosure has a molecular weight of 500 to 5,000 and is composed of hydrogen atoms, carbon atoms, and heteroatoms. The heteroatom is at least one selected from oxygen atoms, sulfur atoms, fluorine atoms, and silicon atoms. Furthermore, the compound of the present disclosure has one or more alicyclic structures, one or more aromatic ring structures directly bonded to the alicyclic structures, and one or more monovalent substituents Ms directly bonded to the aromatic ring structures. The monovalent substituents Ms are at least one selected from a group containing a monovalent fluorinated aliphatic group, a group containing a monovalent fluorinated sulfur group, a group containing a monovalent siloxanyl group, and a group containing a monovalent saturated hydrocarbon group. The heteroatom is contained in at least one or more selected from the group consisting of the alicyclic structure, the aromatic ring structure, and the substituent Ms. Preferably, the heteroatom is contained in at least the substituent Ms, and more preferably, the heteroatom is contained only in the substituent Ms.

[0013] The alicyclic structure may be bonded with a substituent other than an aromatic ring structure. The substituent other than the aromatic ring structure may be any one that does not contain atoms other than hydrogen atoms, carbon atoms, and the heteroatoms, and examples thereof include a monovalent fluorine-containing aliphatic group, a monovalent aliphatic group that does not have a fluorine atom (hereinafter also referred to as a "non-fluorine aliphatic group"), and a fluorine atom. The alicyclic structure, the monovalent fluorine-containing aliphatic group, and the monovalent non-fluorine aliphatic group will be described in detail later.

[0014] The aromatic ring structure may be bonded with a substituent other than the alicyclic structure and the monovalent substituent Ms. The substituent other than the alicyclic structure and the substituent Ms may be any one that does not contain atoms other than hydrogen atoms, carbon atoms, and the heteroatoms, and examples thereof include a monovalent non-fluorine-containing aliphatic group and a fluorine atom. The aromatic ring structure and the monovalent substituent Ms will be described in detail later.

[0015] (Molecular Weight) The molecular weight of the compound is 500 to 5,000, preferably 600 to 3,000, more preferably 600 to 2,000, and particularly preferably 1,000 to 2,000. When the molecular weight of the compound is the upper limit value or less, deposition is possible at a temperature equal to or lower than the thermal decomposition temperature. When the molecular weight of the compound is the lower limit value or more, excellent film formability is obtained during deposition. The molecular weight of the compound is１ H-NMR and / or １９ It is calculated by determining the structure of the compound by F-NMR.

[0016] (95% mass reduction temperature) Compound 1 x 10 －３ When the temperature is increased from 50°C to 500°C at a rate of 2°C per minute in a vacuum of 100 Pa or less, the temperature at which the thermal mass reduction rate reaches 95% (hereinafter also referred to as "95% mass reduction temperature") is preferably in the range of 150 to 300°C. If the 95% mass reduction temperature is within the above range, the vapor deposition property is excellent. Details of the method for measuring the thermal mass reduction rate are as described in the examples below.

[0017] The compound preferably has a visible light transmittance of 85% or more, more preferably 90% or more, of an organic film-coated substrate formed by vapor-depositing the compound onto the surface of a quartz substrate to a film thickness of 50 nm. When the visible light transmittance is equal to or greater than the lower limit, the second region of the conductive film has excellent light transmittance even when a thin film of the compound is formed in the second region. Details of the method for measuring the visible light transmittance of the organic film-coated substrate are as described in the Examples below.

[0018] The compound is preferably a solid at 25° C. If the compound is a solid at 25° C., the shape stability of the vapor-deposited film is excellent.

[0019] (Alicyclic structure) An alicyclic structure is a ring structure that does not contain an aromatic ring. The alicyclic structure may be a carbon ring whose ring skeleton is composed only of carbon atoms, or a hetero ring whose ring skeleton contains atoms other than carbon atoms. However, since the compound is composed of hydrogen atoms, carbon atoms, and the hetero atoms, the alicyclic structure does not contain atoms other than hydrogen atoms, carbon atoms, and the hetero atoms. Therefore, examples of hetero rings include those whose ring skeleton is composed of carbon atoms and oxygen atoms or sulfur atoms.

[0020] The alicyclic structure may be monocyclic or fused cyclic. The number of members in a monocyclic alicyclic structure is preferably 3 to 11, more preferably 4 to 10, and particularly preferably 5 to 8. The number of rings constituting a fused cyclic alicyclic structure is preferably 2 to 6, and more preferably 2 to 4. The number of members in these rings is preferably 3 to 11, more preferably 4 to 10, and particularly preferably 5 to 8. The alicyclic structure may be saturated or unsaturated. A saturated alicyclic structure is preferred in terms of superior heat resistance.

[0021] Examples of the alicyclic structure include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclononane ring, a cyclodecane ring, a cyclopropene ring, a cyclobutene ring, a cyclohexene ring, a cycloheptene ring, a cyclooctene ring, a norbornane ring, an adamantane ring, a bicycloundecane ring, a decahydronaphthalene ring, a cubane ring, a spiropentadiene ring, a decalin ring, a bicyclo[3.3.0]octane ring, and a bicyclo[2.2.2]octane ring. Among these, a cyclohexane ring, an adamantane ring, and a bicyclo[3.3.0]octane ring are preferred, and a cyclohexane ring is more preferred.

[0022] (Aromatic ring structure) The aromatic ring structure is a ring structure containing an aromatic ring. The aromatic ring structure may be a carbon ring whose ring skeleton is composed only of carbon atoms, or a hetero ring whose ring skeleton contains atoms other than carbon atoms. However, since the compound is composed of hydrogen atoms, carbon atoms, and the hetero atoms, the aromatic ring structure does not contain atoms other than hydrogen atoms, carbon atoms, and the hetero atoms. Therefore, examples of hetero rings include those whose ring skeleton is composed of carbon atoms and oxygen atoms or sulfur atoms.

[0023] The aromatic ring structure may be either monocyclic or fused ring. Monocyclic structures are preferred in terms of superior visible light transmittance. The number of members in the monocyclic aromatic ring structure is preferably 5 to 10, more preferably 5 to 6. The fused ring aromatic ring structure may be one in which two or more aromatic rings are fused, or one in which one or more aromatic rings are fused with one or more alicyclic rings. However, the monovalent fluorine-containing aliphatic group is bonded to at least the aromatic ring. The number of rings constituting the fused ring aromatic ring structure is preferably 2 to 4, more preferably 2 to 3. The number of members in these rings is preferably 5 to 10, more preferably 5 to 6.

[0024] Examples of the aromatic ring structure include a benzene ring, a naphthalene ring, an anthracene ring, an azulene ring, a furan ring, a thiophene ring, a thienothiophene ring, a benzofuran ring, and a benzothiophene ring. Among these, a benzene ring and a thiophene ring are preferred, and a benzene ring is more preferred.

[0025] (Monovalent Substituent Ms) <Group Containing a Monovalent Fluorine-Containing Aliphatic Group> The fluorine-containing aliphatic group is an aliphatic group having a fluorine atom. The aliphatic group is an organic group not having an aromatic ring structure. However, since the compound is composed of hydrogen atoms, carbon atoms, and the heteroatom, the group containing the monovalent fluorine-containing aliphatic group does not contain atoms other than hydrogen atoms, carbon atoms, and the heteroatom. The group containing the monovalent fluorine-containing aliphatic group may be linear, cyclic, or a combination thereof. In terms of superior Ag repellency, a linear group is preferred. The linear fluorine-containing aliphatic group may be linear or branched, with a linear group being preferred. Furthermore, the group containing the monovalent fluorine-containing aliphatic group preferably has 1 to 20 carbon atoms as a whole, more preferably 1 to 10, and even more preferably 2 to 6.

[0026] Examples of groups containing a monovalent fluorine-containing aliphatic group include a fluoroalkyl ether group, a fluoroalkyl thioether group, and a fluoroalkyl group. Examples of the fluoroalkyl ether group include the following groups f1, f2, and f3. Examples of the fluoroalkyl group include the following group f4. Among these, the fluoroalkyl ether group is preferred, and group f1 is more preferred, in terms of superior Ag repellency.

[0027] -Z １ - (OR １ ) ｎ -F Formula f1 where R １ is an alkylene group or a fluoroalkylene group, n is an integer of 1 or more, and n R １ may be the same or different, Z １ is a divalent linking group that does not contain a single bond or an aromatic ring structure.

[0028] -Z 1a -OR- ｆ -R 1a -F Formula f2 where R 1a is a single bond, an alkylene group, or a fluoroalkylene group, and R ｆ is a chain alkylene group or a fluoroalkylene group, Z 1a is a divalent linking group that does not contain a single bond or an aromatic ring structure.

[0029] However, X ３ is a hydrogen atom or a fluorine atom, and R 1b represents an alkylene group or a fluoroalkylene group which may have an etheric oxygen atom at the terminal, or a group which has an etheric oxygen atom between carbon atoms in an alkylene group or a fluoroalkylene group which has two or more carbon atoms and may have an etheric oxygen atom at the terminal, and Z 1b is a divalent linking group that does not contain a single bond or an aromatic ring structure.

[0030] -R １ｃ -F Formula f4 where R １ｃ is an alkylene group or a fluoroalkylene group.

[0031] In formula f1, R １ The alkylene group and the fluoroalkylene group in formula f1 may each be linear, cyclic, or a combination thereof. In terms of superior Ag repellency, a linear (straight-chain or branched) chain is preferred, and a straight-chain chain is more preferred. The number of carbon atoms in each of the alkylene group and the fluoroalkylene group is preferably 4 or less, more preferably 2 or less, and may be 1. A polyfluoroalkylene group is preferred as the fluoroalkylene group. When n R １ may be the same or different. In terms of superior Ag repellency, n R １ Among them, the R adjacent to the terminal F １ is preferably a polyfluoroalkylene group, more preferably a perfluoroalkylene group.

[0032] In formula f1, n is an integer of 1 or more, and may be an integer of 2 or more. In terms of excellent vapor deposition properties on a substrate, n is preferably 4 or less, more preferably 3 or less, and particularly preferably 2.

[0033] In the formula f1, Z １ is a divalent linking group that does not contain a single bond or an aromatic ring structure. The divalent linking group may be any group that does not contain an aromatic ring structure and does not contain atoms other than hydrogen atoms, carbon atoms, and the heteroatoms, and examples thereof include an alkylene group and a fluoroalkylene group. The alkylene group and the fluoroalkylene group are each represented by R １ The alkylene group and the fluoroalkylene group in Z are exemplified. １ As the group, a single bond is preferred in that it has better Ag repellency.

[0034] As the group f1, the group f1-1 is preferred. １ -O-CF ２ CFX ３ａ -(O-R １ｄ ) ｎ－１ -F Formula f1-1 where R １ｄ is an alkylene group or a fluoroalkylene group, and X ３ａ is a hydrogen atom or a fluorine atom. １ is as described above.

[0035] R １ｄ As for R １ The same as above can be mentioned. １ｄ As the alkylene group, a perfluoroalkylene group is preferred in terms of superior Ag repellency, and a linear perfluoroalkylene group having 1 to 4 carbon atoms is particularly preferred.

[0036] Examples of the group f1-1 include the following: —O—CF ２ CF ２ -O-CF ２ -F, -O-CF ２ CHF-O-CF ２ -F, -O-CF ２ CF ２ -O-(CF ２ ) ３ -F, -O-CF ２ CHF-O-(CF ２ ) ３ -F.

[0037] In formula f2, R １a The alkylene group and fluoroalkylene group in R １ The alkylene group and the fluoroalkylene group in R ｆ The chain alkylene group and fluoroalkylene group in R may be linear or branched, and is preferably linear. ｆ The number of carbon atoms in R is preferably 1 to 4. ｆ As Z, a chain polyfluoroalkylene group is preferred. 1a As for Z, １ The same can be mentioned.

[0038] As the group f2, the group f2-1 is preferred. １a -O-CF ２ CFX ３ｂ -R １a -F Formula f2-1 where X ３ｂ is a hydrogen atom or a fluorine atom. １a and Z １a is as described above.

[0039] In formula f3, R １ｂThe alkylene group and fluoroalkylene group in R １ In the alkylene group or fluoroalkylene group having two or more carbon atoms and having an etheric oxygen atom between carbon atoms, the number of etheric oxygen atoms between carbon atoms is, for example, 1 to 2. １ｂ As for Z, １ The same can be mentioned.

[0040] In formula f4, R １ｃ As for R １ The same can be mentioned.

[0041] The group containing the monovalent fluorine-containing aliphatic group may be, for example, group f5 or group f6 shown below. ２ (-X １ -Rf １ )n1 Formula f5 -Z ３ (-X ２ -Rf ２ -R ２ ) ｎ２ Formula f6 where Rf １ is -CF ３ , -CF ２ H or -CFH ２ and Rf ２ Ha-CF ２ - or -CFH-, and R ２ is an alkyl group, and X １ and X ２ is —O— or —S—, and Z ２ and Z ３ is a (n1+1)-valent or (n2+1)-valent linking group that does not contain a single bond or an aromatic ring structure, and n1 and n2 are integers from 1 to 9. The (n1+1)-valent or (n2+1)-valent linking group may be any group that does not contain an aromatic ring structure and does not contain atoms other than hydrogen atoms, carbon atoms, and the heteroatoms, and examples thereof include an alkylene group, an alkylene ether group, a fluoroalkylene group, and a fluoroalkylene ether group. These groups may be chain-like (straight-chain or branched-chain) or cyclic, or may be a combination thereof. The alkylene group and the fluoroalkylene group are each represented by R１ In the alkylene ether group and the fluoroalkylene ether group, the etheric oxygen atom may be located at the bonding terminal to the aromatic ring. ２ The alkyl group as Z may be linear, cyclic, or a combination thereof. A linear (straight or branched) alkyl group is preferred in terms of superior Ag repellency. The number of carbon atoms in the alkyl group is preferably 10 or less, more preferably 4 or less, and may be 1. n1 and n2 are preferably 2 to 9 in terms of superior Ag repellency, and are preferably 1 to 3 in terms of ease of production. Z ２ and Z ３ As the linking group, a divalent to nonavalent linking group not containing an aromatic ring structure is preferred, and a tetravalent to nonavalent linking group is more preferred, in terms of superior Ag repellency, and a single bond or a divalent linking group not containing an aromatic ring structure is preferred, and a single bond or a divalent linking group is more preferred, in terms of ease of production.

[0042] Examples of the group f5 include the following: ３ , -SCF ３ , —O—CH ２ -OCF ３ , —O—CH ２ CH ２ -OCF ３ , —O—CH ２ CH ２ CH ２ -OCF ３ , —O—CH ２ -SCF ３ , —O—CH ２ CH ２ -SCF ３ , —O—CH ２ CH ２ CH ２ -SCF ３ , -CH ２ -OCF ３ , -CH ２ CH ２ -OCF ３ , -CH ２ CH ２ CH ２ -OCF ３ and the groups shown below:

[0043]

[0044] Examples of the group f6 include the following: ２ H, -SCF ２ H, —O—CH ２ -OCF ２ H, —O—CH ２ CH ２ -OCF ２ H, —O—CH ２ CH ２ CH ２ -OCF ２ H, —O—CH ２ -SCF ２ H, —O—CH ２ CH ２ -SCF ２ H, —O—CH ２ CH ２ CH ２ -SCF ２ H, —CH ２ -OCF ２ H, —CH ２ CH ２ -OCF ２ H, —CH ２ CH ２ CH ２ -OCF ２ H, and the groups shown below:

[0045]

[0046] <Group Containing Monovalent Fluorinated Sulfur Group> Examples of the group containing the monovalent fluorinated sulfur group include groups represented by the following formulae fs1 and fs2: -Z ４ -SF ５ Formula fs1 -Z ５ -SF ４ -R ３ Formula fs2 where R ３ is a hydrocarbon group, and Z ４ and Z ５ is a divalent linking group that does not contain a single bond or an aromatic ring structure.

[0047] Z ４ and Z ５The divalent linking group as R may be any group as long as it does not contain an aromatic ring structure and does not contain atoms other than hydrogen atoms, carbon atoms, and the heteroatoms, and examples thereof include alkylene groups, alkylene ether groups, fluoroalkylene groups, and fluoroalkylene ether groups. These groups may be chain-like (straight chain or branched chain) or cyclic, or may be a combination thereof. The alkylene group and the fluoroalkylene group are each represented by R １ In the alkylene ether group and the fluoroalkylene ether group, the etheric oxygen atom may be located at the bonding terminal to the aromatic ring. ４ and Z ５ As the carbon number, a single bond is preferable because it has better Ag repellency. Furthermore, the group containing a monovalent fluorinated sulfur group preferably has 0 to 10 carbon atoms, more preferably 0 to 6 carbon atoms, and even more preferably 0 to 3 carbon atoms.

[0048] <Group Containing a Monovalent Siloxanyl Group> In this specification, the term "siloxanyl group" refers to a group having at least one Si—O—Si bond. Examples of the group containing a monovalent siloxanyl group include groups represented by the following formulae sx1 and sx2. However, R ４ are each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms, and Z ６ represents a single bond or a divalent linking group that does not contain an aromatic ring structure, and a, b, c, and d are each independently an integer of 0 to 20, and satisfy a+b+c+d>0.

[0049] However, R ５ are each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms, and Z ７ is a divalent linking group that does not contain a single bond or an aromatic ring structure, e is an integer of 1 to 20, f is an integer of 0 to 20, and e+f>1 is satisfied.

[0050] Specific examples of alkyl groups having 1 to 10 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, hexyl, cyclohexyl, 2-ethylhexyl, and octyl groups. Specific examples of aryl groups having 6 to 12 carbon atoms include phenyl and naphthyl groups. Of these, the most preferred is a methyl group.

[0051] Z ６ and Z ７ The divalent linking group as R may be any group as long as it does not contain an aromatic ring structure and does not contain atoms other than hydrogen atoms, carbon atoms, and the heteroatoms, and examples thereof include alkylene groups, alkylene ether groups, fluoroalkylene groups, and fluoroalkylene ether groups. These groups may be chain-like (straight chain or branched chain) or cyclic, or may be a combination thereof. The alkylene group and the fluoroalkylene group are each represented by R １ In the alkylene ether group and the fluoroalkylene ether group, the etheric oxygen atom may be located at the bond terminal. ６ As the group sx1, an ethylene group, a trimethylene group, an oxyethylene group, an oxytrimethylene group, etc. are preferred in terms of superior Ag repellency. In addition, in the formulas sx1 and sx2, a+b+c+d and e+f are preferably 1 to 20, more preferably 2 to 10, and further preferably 2 to 4.

[0052] Examples of the group sx1 include the following.

[0053]

[0054] Examples of the group sx2 include the following.

[0055]

[0056] <Group containing a monovalent saturated hydrocarbon group> Examples of the group containing a monovalent saturated hydrocarbon group include a group represented by the following formula sh1: -Z ８ -R ６　　　　　　　Formula sh1 where R ６ is a saturated hydrocarbon group having 4 to 24 carbon atoms, and Z ８ Z is a single bond, a divalent linking group not containing an aromatic ring structure, an oxygen atom, or a sulfur atom. ８ As for Z, １ Examples include the same as above. ６ The saturated hydrocarbon group as is preferably a chain alkyl group having 12 to 24 carbon atoms, and more preferably a chain alkyl group having 16 to 22 carbon atoms.

[0057] (Group Containing a Monovalent Non-Fluorine-Containing Aliphatic Group) Examples of the group containing a monovalent non-fluorine-containing aliphatic group include groups in which a fluorine atom in the group containing the monovalent fluorine-containing aliphatic group described above is substituted with a hydrogen atom, and examples include alkyl ether groups and alkyl groups. The molecular weight, boiling point, and glass transition temperature can be adjusted by the group containing a monovalent non-fluorine-containing aliphatic group. As the monovalent non-fluorine-containing aliphatic group, an alkyl group is preferred. The alkyl group may be linear, cyclic, or a combination thereof. From the viewpoint of improving the molecular weight, boiling point, and glass transition temperature, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, and a cyclohexyl group are preferred, a methyl group, a tert-butyl group, and a cyclohexyl group are more preferred, and a methyl group and a tert-butyl group are particularly preferred. The number of monovalent non-fluorine-containing aliphatic groups substituted on the aromatic ring is preferably 0 to 2, and more preferably 0 to 1.

[0058] (Structure of Compound) The number of alicyclic structures in the compound may be one or two or more. It can be appropriately set within a range in which the molecular weight of the compound is 500 to 5,000. From the viewpoint of superior film-forming properties during vapor deposition, 2 to 6 alicyclic structures are preferred, and 2 to 4 are more preferred.

[0059] In the compound, the number of aromatic ring structures directly bonded to one alicyclic structure may be 1 or 2 or more, but from the viewpoint of superior film-forming properties during vapor deposition, 2 to 4 is preferred.

[0060] When a compound has two or more alicyclic structures and two or more aromatic ring structures directly bonded to the alicyclic structures, the aromatic ring structures may be bonded to the same alicyclic structure or different alicyclic structures.

[0061] When two or more aromatic ring structures are bonded to the same alicyclic structure, all of the aromatic ring structures may be bonded to different carbon atoms among the carbon atoms constituting the ring skeleton of the alicyclic structure, or at least some of the aromatic ring structures may be bonded to the same carbon atom among the carbon atoms constituting the ring skeleton of the alicyclic structure. Note that the number of aromatic ring structures bonded to one carbon atom is up to two.

[0062] In the compound, the number of monovalent substituents Ms directly bonded to one aromatic ring structure may be 1 or 2 or more. From the viewpoint of superior vapor deposition properties, 3 or less is preferable, and 1 is particularly preferable.

[0063] The bonding position of the monovalent substituent Ms in the aromatic ring structure is not particularly limited and can be appropriately selected in consideration of the availability of raw materials, etc. When the aromatic ring structure is a benzene ring, the bonding position of the monovalent substituent Ms in the aromatic ring structure is preferably the para position with respect to the bonding position to the alicyclic structure.

[0064] A preferred example of the compound of the present disclosure is Compound 1.

[0065] where m is an integer of 1 to 8, A is an m-valent group containing one or more alicyclic structures, and Y １ ~Y ５ are each independently the monovalent substituent Ms, a hydrogen atom, a fluorine atom, or a monovalent non-fluorinated aliphatic group (excluding groups containing the monovalent saturated hydrocarbon group), and Y １ and Y ２ , Y ２ and Y ３ , Y ３ and Y ４ , Y ４ and Y ５ One or two of the combinations of may be bonded to each other to form a ring together with the carbon atoms to which they are bonded, and Y １ ~Y ５At least one of Y is the monovalent substituent Ms. １ ~Y ５ At least one of the groups is preferably a group containing the monovalent fluorine-containing aliphatic group.

[0066] m is preferably 2 to 6, more preferably 2 to 4, and particularly preferably 4, in view of excellent film-forming properties during vapor deposition.

[0067] The preferred range of the number of alicyclic structures contained in A is the same as the preferred range of the number of alicyclic structures in the compound. Examples of A include a group consisting of one alicyclic structure and a group in which two or more alicyclic structures are bonded directly or via a linking group. Examples of the group in which two or more alicyclic structures are bonded via a linking group include a group in which two alicyclic structures are bonded via one divalent linking group, a group in which a (a is an integer of 3 or more) alicyclic structures are bonded in series via a-1 divalent linking groups, and a group in which a alicyclic structures are bonded via one a-valent linking group.

[0068] Examples of divalent linking groups include divalent hydrocarbon groups which may have a substituent. The divalent hydrocarbon group may be linear, cyclic, or a combination thereof. The divalent linear hydrocarbon group may be saturated or unsaturated. The divalent linear hydrocarbon group may have, for example, 1 to 6 carbon atoms. The divalent linear hydrocarbon group is preferably a methylene group which may have a substituent. The divalent cyclic hydrocarbon group may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated. The divalent cyclic hydrocarbon group may be monocyclic or fused ring. The divalent cyclic hydrocarbon group may have, for example, 4 to 10 carbon atoms.

[0069] The substituent that the divalent hydrocarbon group may have may be any substituent that does not contain atoms other than hydrogen atoms, carbon atoms, oxygen atoms, and fluorine atoms, and examples thereof include fluorine atoms and monovalent hydrocarbon groups that may have a substituent. The monovalent hydrocarbon group may be linear, cyclic, or a combination thereof. The monovalent linear hydrocarbon group may be saturated or unsaturated. The monovalent linear hydrocarbon group may have, for example, 1 to 6 carbon atoms. The monovalent cyclic hydrocarbon group may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated. The monovalent cyclic hydrocarbon group may be monocyclic or fused cyclic. The monovalent cyclic hydrocarbon group may have, for example, 4 to 10 carbon atoms. Examples of the substituent that the monovalent hydrocarbon group may have include the same substituents that the divalent hydrocarbon group may have.

[0070] Examples of the a-valent linking group include groups in which a-2 hydrogen atoms have been removed from the above-mentioned optionally substituted divalent hydrocarbon groups.

[0071] Examples of A when m is 2 include groups A-1a, A-1b, A-1c, and A-1d. Examples of A when m is 3 include groups A-2a, A-2b, A-2c, and A-2d. Examples of A when m is 4 include groups A-3a, A-3b, A-3c, and A-3d. Among these, groups A-3a, A-3b, A-3c, and A-3d are preferred, and group A-3a is more preferred.

[0072] However, Z ９ is a single bond or a divalent linking group. *- indicates a bond.

[0073] In Formula A-3a, the two bonds in each of the two cyclohexane rings may be from the same carbon atom or different carbon atoms among the carbon atoms constituting the cyclohexane ring. That is, among the carbon atoms constituting the ring skeleton of the cyclohexane ring, two aromatic ring structures may be bonded to one carbon atom, or one aromatic ring structure may be bonded to each of the two carbon atoms. In terms of excellent vapor deposition properties, it is preferable that two aromatic ring structures are bonded to one carbon atom. The same applies to one of the cyclohexane rings in Formula A-2a. Furthermore, the same applies to the two bonds extending from a single ring structure in Formulas A-1b, A-1d, A-2b, A-2c, A-2d, A-3b, A-3c, and A-3d.

[0074] As the group A-3a, the group A-3a-1 is preferred.

[0075]

[0076] As the group A-3b, the group A-3b-1 is preferred.

[0077]

[0078] As the group A-3c, the group A-3c-1 is preferred.

[0079]

[0080] As the group A-3d, the group A-3d-1 is preferred.

[0081]

[0082] Examples of the group A-3a-1 include a group A-3a-11 and a group A-3a-12.

[0083] However, B １ and B ２ are each independently a hydrogen atom, a fluorine atom, or a monovalent hydrocarbon group which may have a substituent. Cy is a divalent cyclic hydrocarbon group which may have a substituent.

[0084] In formula A-3a-11, B １ and B ２Examples of the monovalent hydrocarbon group in formula A-3a-12 include the same as the monovalent hydrocarbon groups as the substituent described above. In formula A-3a-12, examples of Cy include the same as the divalent cyclic hydrocarbon groups in the divalent linking group described above. Note that the two cyclohexane rings in the formula are bonded to one of the carbon atoms constituting the ring skeleton of Cy.

[0085] In formula 1, Y １ ~Y ５ The monovalent substituent Ms and the monovalent non-fluorinated aliphatic group in Y are the same as those described above. １ ~Y ５ At least one of the groups is a monovalent substituent Ms. In terms of excellent vapor deposition properties, Y １ ~Y ５ Preferably, only one of Y is a monovalent substituent Ms; ３ It is more preferred that only Ms is the monovalent substituent.

[0086] Y １ ~Y ５ Examples of combinations of Y include the following: Combination 1: Y ３ is a group containing a monovalent fluorine-containing aliphatic group, Y １ , Y ２ , Y ４ and Y ５ is a hydrogen atom. Combination 2: Y ３ is a group containing a monovalent fluorine-containing aliphatic group, Y ２ is a monovalent non-fluorinated aliphatic group, Y １ , Y ４ and Y ５ is a hydrogen atom. Combination 3: Y ３ is a group containing a monovalent fluorine-containing aliphatic group, Y ２ and Y ４ is a monovalent non-fluorinated aliphatic group, Y １ and Y ５ is a hydrogen atom.

[0087] Specific examples of Compound 1 include the compounds shown below, in addition to Compounds 1-1 to 1-18 obtained in the Examples described below.

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] A preferred example of the compound of the present disclosure is Compound 2.

[0102] where X is an oxygen atom or a sulfur atom, m is an integer of 1 to 8, A is an m-valent group containing one or more alicyclic structures, and Y ６ ~Y ８ are each independently the monovalent substituent Ms, a hydrogen atom, a fluorine atom, or a monovalent non-fluorinated aliphatic group (excluding groups containing the monovalent saturated hydrocarbon group), and Y ６ and Y ７ , Y ７ and Y ８ One or two of the combinations of may be bonded to each other to form a ring together with the carbon atoms to which they are bonded, and Y ６ ~Y ８ At least one of Y is the monovalent substituent Ms. ６ ~Y ８ At least one of Y is preferably a group containing the monovalent fluorine-containing aliphatic group. ９ ~Y １１are each independently the monovalent substituent Ms, a hydrogen atom, a fluorine atom, or a monovalent non-fluorinated aliphatic group (excluding groups containing the monovalent saturated hydrocarbon group), and Y １０ and Y １１ may be bonded to each other to form a ring together with the carbon atoms to which they are attached, and Y ９ ~Y １１ At least one of Y is the monovalent substituent Ms. ９ ~Y １１ At least one of the groups is preferably a group containing the monovalent fluorine-containing aliphatic group.

[0103] m is preferably 2 to 6, more preferably 2 to 4, and particularly preferably 4, in view of excellent film-forming properties during vapor deposition.

[0104] The preferred range of the number of alicyclic structures contained in A is the same as the preferred range of the number of alicyclic structures in the compound. Examples of A include a group consisting of one alicyclic structure and a group in which two or more alicyclic structures are bonded directly or via a linking group. Examples of the group in which two or more alicyclic structures are bonded via a linking group include a group in which two alicyclic structures are bonded via one divalent linking group, a group in which a (a is an integer of 3 or more) alicyclic structures are bonded in series via a-1 divalent linking groups, and a group in which a alicyclic structures are bonded via one a-valent linking group.

[0105] Examples of divalent linking groups include divalent hydrocarbon groups which may have a substituent. The divalent hydrocarbon group may be linear, cyclic, or a combination thereof. The divalent linear hydrocarbon group may be saturated or unsaturated. The divalent linear hydrocarbon group may have, for example, 1 to 6 carbon atoms. The divalent linear hydrocarbon group is preferably a methylene group which may have a substituent. The divalent cyclic hydrocarbon group may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated. The divalent cyclic hydrocarbon group may be monocyclic or fused ring. The divalent cyclic hydrocarbon group may have, for example, 4 to 10 carbon atoms.

[0106] The substituent that the divalent hydrocarbon group may have may be any substituent that does not contain atoms other than hydrogen atoms, carbon atoms, oxygen atoms, and fluorine atoms, and examples thereof include fluorine atoms and monovalent hydrocarbon groups that may have a substituent. The monovalent hydrocarbon group may be linear, cyclic, or a combination thereof. The monovalent linear hydrocarbon group may be saturated or unsaturated. The monovalent linear hydrocarbon group may have, for example, 1 to 6 carbon atoms. The monovalent cyclic hydrocarbon group may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated. The monovalent cyclic hydrocarbon group may be monocyclic or fused cyclic. The monovalent cyclic hydrocarbon group may have, for example, 4 to 10 carbon atoms. Examples of the substituent that the monovalent hydrocarbon group may have include the same substituents that the divalent hydrocarbon group may have.

[0107] Examples of the a-valent linking group include groups in which a-2 hydrogen atoms have been removed from the above-mentioned optionally substituted divalent hydrocarbon groups.

[0108] Examples of A include the same as those in the case of Compound 1.

[0109] In formula 2-1 and formula 2-2, Y ６ ~Y １１ The monovalent substituent Ms and the monovalent non-fluorinated aliphatic group in Y are the same as those described above. ６ ~Y ８ At least one of the groups is a monovalent substituent Ms. In terms of excellent vapor deposition properties, Y ６ ~Y ８ Preferably, only one of Y is a monovalent substituent Ms; ６ It is more preferred that only Y is the monovalent substituent Ms. ９ ~Y １１ At least one of the groups is a monovalent substituent Ms. In terms of excellent vapor deposition properties, Y ９ ~Y １１ Preferably, only one of Y is a monovalent substituent Ms; １１ It is more preferred that only Ms is the monovalent substituent.

[0110] Y ６ ~Y ９Examples of combinations of Y include the following: Combination 1: Y ６ is a group containing a monovalent fluorine-containing aliphatic group, Y ７ and Y ８ is a hydrogen atom. Combination 2: Y ６ is a group containing a monovalent fluorine-containing aliphatic group, Y ７ is a monovalent non-fluorinated aliphatic group, Y ８ is a hydrogen atom. Combination 3: Y ６ is a group containing a monovalent fluorine-containing aliphatic group, Y ７ and Y ８ is a monovalent non-fluorinated aliphatic group.

[0111] Specific examples of Compound 2 include Compound 2-3 obtained in the Examples below, as well as the following compounds.

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] A preferred example of the compound of the present disclosure is Compound 3.

[0118] where m is an integer of 1 to 8, B is an m-valent linking group that does not contain an alicyclic structure, and Y １２ ~Y １６ are each independently the monovalent substituent Ms, a hydrogen atom, a fluorine atom, a monovalent non-fluorinated aliphatic group (excluding groups containing the monovalent saturated hydrocarbon group), or a monovalent group containing one or more alicyclic structures, and Y １２ and Y １３ , Y １３ and Y １４ , Y １４ and Y １５ , Y １５ and Y １６ One or two of the combinations of may be bonded to each other to form a ring together with the carbon atoms to which they are bonded, and Y １２ ~Y１６ At least one of the groups represented by Y is the monovalent substituent Ms; １２ ~Y １６ At least one of Y is a monovalent group containing one or more alicyclic structures. １２ ~Y １６ At least one of the groups is preferably a group containing the monovalent fluorine-containing aliphatic group.

[0119] m is preferably 2 to 6, more preferably 2 to 4, and particularly preferably 4, in view of excellent film-forming properties during vapor deposition.

[0120] Y １２ ~Y １６ The number of alicyclic structures contained in the formula (I) is preferably in the range of 1 to 2, more preferably 1.

[0121] A specific example of Compound 3 is Compound 3-1 obtained in the Examples described below.

[0122] (Method for Producing Compound) The compound of the present disclosure can be produced by appropriately combining known methods. For example, compound p1 can be reacted with compound p2 to produce compound 1 having group f1-1 as a group containing a monovalent fluorinated aliphatic group.

[0123] where m and A are as defined above. ６ ~Y １０ are each independently -Z 1b -OH, a hydrogen atom, a fluorine atom, or a monovalent aliphatic group not containing a fluorine atom, ６ and Y ７ , Y ７ and Y ８ , Y ８ and Y ９ , Y ９ and Y １０ One or two of the combinations of may be bonded to each other to form a ring together with the carbon atoms to which they are bonded, and Y ６ ~Y １０ At least one of them is -Z １ｂ -OH. Z 1b is as described above.

[0124] CF ２ = CFX２ -(O-R １ｄ ) ｎ－１ -F Formula p2 where n, R １ｄ and X ２ is as described above.

[0125] When compound p1 reacts with compound p2, -Z of compound p1 1b -OH is converted to group f1-1. Compound p1 and compound p2 are both commercially available products. An example of a method for reacting compound p1 and compound p2 is a method in which compound p1, compound p2, a solvent, and potassium carbonate are mixed and stirred. The reaction temperature is, for example, 20 to 80°C. The reaction time is, for example, 1 to 24 hours. After the reaction, purification, removal of the liquid medium, and the like can be carried out as necessary.

[0126] [Conductive Film] The conductive film of the present disclosure has a first region and a second region exhibiting a higher light transmittance than the first region. The conductive film of the present disclosure also has a first film containing a conductive material and a second film containing a compound of the present disclosure, the first film being disposed so as to overlap at least the first region of the first and second regions, and the second film being disposed so as to overlap the second region.

[0127] Hereinafter, a conductive film and a method for manufacturing the same according to one embodiment will be described with reference to FIGS.

[0128] 1 and 2 are explanatory diagrams showing a conductive film 1 of this embodiment. FIG. 1 is a plan view of the conductive film 1, and FIG. 2 is a cross-sectional view taken along line II-II in FIG. 1. As shown in FIGS. 1 and 2, the conductive film 1 has a first film 10, a second film 15, and a third film 20. The conductive film 1 is provided on a substrate 50. The substrate 50 is an object on which the conductive film 1 is formed. The substrate 50 is optically transparent. The third film 20 is provided on the substrate 50, and the first film 10 is provided on the third film 20. The second film 15 is provided between the first film 10 and the third film 20.

[0129] The conductive film 1 has a first region 10A and a second region 10B having a higher light transmittance than the first region 10A. In the conductive film 1 of this embodiment, the first film 10 is located in the first region 10A. The first film 10 is not present in the second region 10B. The lower surface 11a of the first film 10 is in contact with the third film 20. In addition, the side surface 11b of the first film 10 is in contact with the second film 15.

[0130] 1, in the conductive film 1, a plurality of second regions 10B are arranged in a matrix, and the remaining portion has a lattice-shaped first region 10A, i.e., a lattice-shaped first film 10. In Fig. 1, the second region 10B has a rectangular shape in a plan view, but is not limited to this and various shapes in a plan view can be adopted depending on the design.

[0131] (First Film) The first film 10 is a film containing a conductive material. The conductive material of the first film 10 is not particularly limited as long as it is a conductive material, but preferably contains silver (Ag), gold (Au), copper (Cu), aluminum (Al), magnesium (Mg), zinc (Zn), indium (In), tin (Sn), ytterbium (Yb), or the like. Specific examples include metals such as Ag, Au, Cu, Al, Mg, magnesium silver (MgAg), and ytterbium silver (YbAg), and conductive metal oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), and zinc oxide (ZnO). Because the compound of the present disclosure has excellent Ag repellency, the conductive material of the first film 10 preferably contains Ag.

[0132] The first film 10 is preferably formed to a thickness that ensures the conductivity of the entire conductive film 1. The first film 10 may or may not be optically transparent as long as it can ensure the required conductivity. The film thickness of the first film 10 is, for example, 10 to 1,000 nm. The first film 10 that is formed to a thickness of 50 nm or less is optically transparent.

[0133] The first film 10 may be composed of a thick film portion (corresponding to the first film 10 in FIGS. 1 and 2) located in the first region 10A and a thin film portion located in the second region 10B. The lower surface of the thin film portion is in contact with the second film 15.

[0134] The thin film portion is thinner than the thick film portion and is formed to a thickness that ensures light transmittance. The thickness of the thin film portion is, for example, 0 to 50 nm. In terms of excellent transparency of the second region 10B of the conductive film 1, it is preferable that there be no thin film portion.

[0135] (Second Film) The second film 15 is a film containing the compound of the present disclosure. The second film 15 is disposed so as to overlap the second region 10B. The second film 15 is used to form the first film 10 by vapor deposition, as will be described later in the method for manufacturing a conductive film.

[0136] The compound of the present disclosure has the advantage of transmitting light in the visible light wavelength range and repelling conductive metals when they are formed by vapor deposition, making it difficult for conductive materials to form a film on the compound. Therefore, even when second film 15 overlaps second region 10B, which has optical transparency, the optical transparency of second region 10B is not impaired.

[0137] The second film 15 is typically formed to a thickness equal to or thinner than the maximum thickness of the first film 10. The thickness of the second film 15 is preferably 10 to 500 nm, and more preferably 10 to 100 nm. If the thickness of the second film 15 is equal to or greater than the above-mentioned lower limit, the second film 15 has excellent repellency against metals, which are conductive materials, and if the thickness is equal to or less than the above-mentioned upper limit, the second film 15 has excellent transmittance to light in the visible wavelength region.

[0138] (Third Film) In the first embodiment, the third film 20 is provided on the surface 50a of the base material 50. The third film 20 is a film containing a conductive material. Examples of the conductive material of the third film 20 include the same conductive material as that of the first film 10. The conductive material of the first film 10 and the conductive material of the third film 20 may be the same or different.

[0139] The third film 20 is optically transparent. The third film 20 has a higher optical transmittance than the first film 10. The film thickness of the third film 20 is, for example, 0 to 50 nm. Note that, when the first film 10 has a thin film portion, the third film 20 overlaps the thin film portion in plan view. Therefore, the film thickness of the third film 20 and the total film thickness of the thin film portion may be appropriately adjusted so that the third film 20 is optically transparent in the second region 10B.

[0140] It is also possible to use only the third film 20 as a transparent electrode used in various optoelectronic elements such as light-emitting elements and light-receiving elements. On the other hand, a third film 20 formed thin enough to be optically transparent has high wiring resistance. In contrast, the conductive film 1 of this embodiment is formed by stacking the third film 20 and the first film 10. Therefore, the first film 10 and the third film 20 are stacked to form a thick film at the position overlapping the first region 10A. This allows the conductive film 1 to have a low resistance as a whole while ensuring optical transparency at the position overlapping the second region 10B.

[0141] 3 to 5 are schematic diagrams showing a method for manufacturing the conductive film 1 described above. First, as shown in FIG. 3, a conductive material is formed on the surface of a substrate 50 to obtain a third film 20 (step a). Next, as shown in FIG. 4, a compound P of the present disclosure is vapor-deposited on the surface 20a of the third film 20 on the substrate 50 via a mask M to form a second film 15 (step b). Next, as shown in FIG. 5, a conductive material 10X is vapor-deposited on the second film 15 to form a first film 10 (step c).

[0142] <Step a> The third film 20 can be formed by a dry coating method such as evaporation, sputtering, CVD (chemical vapor deposition), or ALD (atomic layer deposition).

[0143] <Step b> The mask M has openings M2 arranged in a matrix and shielding portions M1 arranged in a grid pattern. The compound P is vapor-deposited under reduced pressure at a concentration of, for example, 1×10 －３ The compound P is heated under a pressure of 100 Pa or less. The heating temperature is, for example, 150 to 300°C.

[0144] When the compound P is vapor-deposited through the mask M, the compound P passes through the openings M2 of the mask M and reaches the surface 20a of the third film 20, but is blocked by the blocking portions M1 of the mask M. This forms the second film 15 containing the compound P of the present disclosure. The second film 15 is arranged in a matrix on the surface 20a. Furthermore, in areas where the second film 15 is not formed, the third film 20 is exposed in a lattice pattern.

[0145] <Step c> Conductive material 10X is vapor-deposited from above second film 15. Conductive material 10X does not easily adhere to the surface of second film 15 containing the compound of the present disclosure, but easily adheres to the surface of third film 20 (or substrate 50). Therefore, by vapor-depositing conductive material 10X over the entire surface of substrate 50 from above without using a mask, a relatively thick film of conductive material 10X is formed on the surface of third film 20, and a relatively thin film of conductive material 10X is formed on the surface of second film 15, or no conductive material 10X is formed at all. This forms first film 10. This results in conductive film 1.

[0146] The conductive film having the above-described structure is a novel conductive film having two regions with different light transmittances. Furthermore, the above-described method for manufacturing a conductive film makes it possible to easily manufacture such a conductive film.

[0147] In this embodiment, the second film 15 is present in the second region 10B of the conductive film 1, but a step of removing the second film 15 may be included after the step c shown in Fig. 5. When the thin film portion of the first film 10 is present in the second region 10B, removing the second film 15 allows the second film 15 and the thin film portion to be removed simultaneously.

[0148] 6 is a schematic diagram showing the conductive film 2 obtained by removing the second film 15, and corresponds to FIG. 2 . As shown in FIG. 6 , the conductive film 2 has a first film 13 and a third film 20. In the first region 13A of the conductive film 2, the lattice-shaped first film 10 and the third film 20 overlap. In addition, the third film 20 is present in the second region 13B of the conductive film 2. In the conductive film 2 configured in this manner, the light transmittance of the second region 13B is higher than the light transmittance of the second region 10B of the conductive film 1 described above, and the contrast between the first region 13A and the second region 13B is increased.

[0149] Methods for removing the second film 15 include, for example, a method of dissolving or peeling off the second film 15 using a solvent, or a method of removing it by dry etching. It is preferable to use a solvent that dissolves the second film 15 but does not substantially dissolve other materials that constitute the substrate on which the conductive film 1 is formed. This allows the compound to be removed without impairing the quality of the optoelectronic device. Examples of solvents that can be used to remove the second film 15 include acetone, methyl ethyl ketone, chloroform, dichloromethane, and carbon tetrachloride.

[0150] Furthermore, in this embodiment, the third film 20 is provided, but the third film 20 may be omitted.

[0151] Fig. 7 is an explanatory diagram of a modified example of this embodiment, and corresponds to Fig. 2. The conductive film 3 shown in Fig. 7 has a first film 10 and a second film 15. The first film 10 is provided on a substrate 50. The second film 15 is provided between the first film 10 and the substrate 50.

[0152] The lower surface 11 a of the first film 10 is in contact with the substrate 50 . The side surface 11 b of the first film 10 is in contact with the second film 15 .

[0153] Such a conductive film 3 can be produced in the same manner as the above-described method for producing a conductive film, except that the step (step a) shown in Fig. 3 is not included and the compound P of the present disclosure is vapor-deposited directly onto the surface 50a of the substrate 50. Furthermore, after the conductive film 3 is produced by the step (step c) shown in Fig. 5, a step of removing the second film 15 described above may be included.

[0154] [Optoelectronic Device] The optoelectronic device of the present disclosure includes the conductive film of the present disclosure. Such an optoelectronic device is preferably an organic EL device including a substrate, an anode provided on the substrate, a cathode provided on the substrate, and an active layer disposed between the anode and the cathode, wherein the cathode is the conductive film of the present disclosure.

[0155] 8 is a cross-sectional schematic diagram showing an organic EL element 100 (an optoelectronic element according to this embodiment). The organic EL element 100 has a structure in which a substrate 110, an anode 111, a partition wall 112, a functional layer 113, and a cathode 115 are laminated. The functional layer 113 includes a light-emitting layer. The organic EL element 100 of this embodiment employs a top emission system in which light generated in the functional layer 113 is emitted to the outside through the cathode 115.

[0156] (Substrate) The substrate 110 may or may not be optically transparent. Materials that can be used to form the substrate 110 include inorganic materials such as glass, quartz glass, and silicon nitride, and organic polymers (resins) such as polyimide resin, acrylic resin, and polycarbonate resin. Furthermore, as long as surface insulation is ensured, a metal material can also be used to form the substrate 110. The substrate 110 also includes various wiring and driving elements (not shown) that are electrically connected to the organic EL elements.

[0157] (Anode) The anode 111 is formed on the substrate 110 and supplies holes to the functional layer 113. The anode 111 also has light reflectivity that reflects light emitted from the light-emitting layer included in the functional layer 113.

[0158] The anode 111 includes a conductive material. Examples of the conductive material that can be used include conductive metal oxides such as ITO and IZO. In addition, in order to impart light reflectivity to the anode 111, a reflective film containing metal may be provided on the substrate 110 side of the anode 111 or the functional layer 113 side of the anode 111. In other words, the anode 111 may have a stacked structure of a layer containing a conductive metal oxide and a reflective film containing metal. The anode 111 may be formed of a metal such as silver.

[0159] The thickness of the anode 111 is not particularly limited, but is preferably 30 to 300 nm, for example, 100 nm.

[0160] (Partition Wall) The partition wall 112 overlaps the peripheral edge of the anode 111 and is formed, for example, in a lattice pattern. A functional layer 113 is formed in the opening of the partition wall 112 to partition the organic EL element 100. The partition wall 112 is made of a resin such as polyimide.

[0161] (Functional Layer) The functional layer 113 is formed to overlap the anode 111. The functional layer 113 has a light-emitting layer. In the light-emitting layer, holes injected from the anode 111 and electrons injected from the cathode 115 recombine to emit photons and emit light. The emission wavelength at this time is determined by the material forming the light-emitting layer. The light-emitting layer corresponds to the "active layer" in this disclosure.

[0162] The light-emitting layer can be formed using a material known as a material for light-emitting layers of organic EL elements. The material for forming the light-emitting layer may be used alone or in combination of two or more, and is appropriately selected depending on the desired emission wavelength.

[0163] The functional layer 113 may have a hole injection layer and a hole transport layer between the light-emitting layer and the anode 111. The hole injection layer has a function of facilitating the injection of holes from the anode to the hole transport layer. The hole transport layer has a function of efficiently transporting holes injected from the anode 111 toward the light-emitting layer.

[0164] The functional layer 113 may have an electron transport layer and an electron injection layer between the light-emitting layer and the cathode 115. The electron transport layer has a function of efficiently transporting electrons injected from the cathode 115 toward the light-emitting layer. The electron injection layer has a function of facilitating injection of electrons from the cathode 115 into the electron transport layer.

[0165] (Cathode) The cathode 115 is formed on the entire surface to cover the partition wall 112 and the functional layer 113. The cathode 115 has a function of injecting electrons into the functional layer.

[0166] In the optoelectronic device of this embodiment, the conductive film of the present disclosure is used as the cathode 115. The cathode 115 has a first film 116, a second film 117, and a third film 118.

[0167] The third film 118 is formed to cover the partition walls 112 and the functional layer 113. The configuration and material of the third film 118 can be the same as those shown for the third film 20 of the first embodiment.

[0168] The second film 117 overlaps the functional layer 113 in plan view and is formed on an upper surface 118a of the third film 118. The configuration and material of the second film 117 can be the same as those shown for the second film 15 of the first embodiment.

[0169] The first film 116 is formed to overlap the partition wall 112 in plan view. The configuration and material of the first film 116 can be the same as those shown for the first film 10 of the first embodiment.

[0170] That is, the first region of the cathode 115 overlaps the partition wall 112, and the second region of the cathode 115 overlaps the functional layer 113 including the light-emitting layer.

[0171] (Microcavity Structure) In the organic EL element 100 of this embodiment, the anode 111 and the cathode 115 form an optically resonant structure (microcavity) that resonates light between the anode 111 and the cathode 115, i.e., between the upper surface of the reflective film of the anode 111 and the lower surface of the third film 118. Between the anode 111 and the cathode 115, light generated in the light-emitting layer is repeatedly reflected, and light with a wavelength that matches the optical path length between the anode 111 and the cathode 115 resonates and is amplified. On the other hand, light with a wavelength that does not match the optical path length between the anode 111 and the cathode 115 is attenuated. The "optical path length" here is calculated using the wavelength of the desired light to be emitted outside the element and the refractive index of each layer at the desired wavelength of light.

[0172] The optical path length between the anode 111 and the cathode 115 is set to, for example, an integer multiple of the central wavelength of the light L generated in the light-emitting layer included in the functional layer 113. In this case, the light L emitted from the light-emitting layer is amplified as it approaches the central wavelength and is attenuated as it deviates from the central wavelength, before being emitted to the outside of the organic EL element 100. In this way, the light L emitted from the organic EL element 100 has a narrow half-width of the emission spectrum and improved color purity.

[0173] In the organic EL element 100 having such a configuration, the conductive film of the present disclosure is used as the cathode 115, and therefore the wiring resistance of the cathode 115 can be reduced while maintaining high light extraction efficiency in the second region, thereby achieving good driving.

[0174] In the above-described embodiment, an organic EL element has been exemplified as an optoelectronic element, but the optoelectronic element to which the conductive film of the present disclosure is applied is not limited to an organic EL element.

[0175] The optoelectronic device of the present disclosure may be, for example, a semiconductor laser. A known configuration can be adopted for the semiconductor laser. By using the conductive film described above for the cathode of the semiconductor laser, the resistance of the cathode is reduced, resulting in a semiconductor laser with improved output.

[0176] The optoelectronic device of the present disclosure may be, for example, a light-receiving element such as a photosensor or a solar cell. The photosensor and solar cell may employ a known configuration in which holes and electrons generated in an active layer (light-receiving layer) according to the intensity of light received by the active layer are transferred to a cathode and an anode via a semiconductor layer. By employing the above-described conductive film in the electrodes (anode, cathode) of the photosensor and solar cell, the photosensor has improved detection performance, and the solar cell has improved power generation efficiency.

[0177] The conductive film and optoelectronic device of the present disclosure have high transmittance as a whole device, and are therefore useful in applications such as transparent displays. Furthermore, in under-display cameras, under-display sensors, and the like, it is necessary to increase the transmittance of the display above the camera or sensor, and the conductive film of the present disclosure is extremely useful.

[0178] In addition to optoelectronic devices, the conductive films of the present disclosure can also be used as patterned electrodes and wiring.

[0179] While the preferred embodiments of the present disclosure have been described above, the present disclosure is not limited to these examples. The shapes and combinations of the components shown in the above examples are merely examples, and various modifications can be made based on design requirements and the like without departing from the spirit of the present disclosure.

[0180]

[0023] Note that one preferred aspect of the present disclosure described above includes the following embodiment. [1A] A compound having a molecular weight of 500 to 5,000, composed of hydrogen atoms, carbon atoms, oxygen atoms, and fluorine atoms, and having one or more alicyclic structures, one or more aromatic ring structures directly bonded to the alicyclic structures, and one or more monovalent fluorine-containing aliphatic groups directly bonded to the aromatic ring structures. [2A] The compound of [1A] above, in which the number of the alicyclic structures is two or more. [3A] The compound of [1A] or [2A] above, in which the alicyclic structure is monocyclic. [4A] The compound of any of [1A] to [3A] above, in which the monovalent fluorine-containing aliphatic group is represented by the following formula f1: -Z １ - (OR １ ) ｎ -F Formula f1 where R １ is an alkylene group or a fluoroalkylene group, n is an integer of 2 or more, and n R １ may be the same or different, Z １ is a single bond or a divalent linking group not containing an aromatic ring structure. [5A] A compound according to any one of [1A] to [4A] above, which is represented by the following formula 1: wherein m is an integer of 1 to 8, A is an m-valent group containing one or more of the alicyclic structures, and Y １ ~Y ５ are each independently the monovalent fluorine-containing aliphatic group, a hydrogen atom, a fluorine atom or a monovalent aliphatic group not containing a fluorine atom, and Y １ and Y ２ , Y ２ and Y ３ , Y ３ and Y ４ , Y ４ and Y ５ One or two of the combinations of may be bonded to each other to form a ring together with the carbon atoms to which they are bonded, and Y １ ~Y ５[6A] The compound of [5A] above, wherein m in formula 1 is 2 and A is a group represented by the following formula A-1a, or m in formula 1 is 3 and A is a group represented by the following formula A-2a, or m in formula 1 is 4 and A is a group represented by the following formula A-3a. However, Z ９ is a single bond or a divalent linking group not containing an aromatic ring structure. *- represents a bond. [7A] A conductive film having a first region and a second region exhibiting higher light transmittance than the first region, the conductive film comprising: a first film containing a conductive material; and a second film containing a compound according to any one of [1A] to [6A], wherein the first film is disposed so as to overlap at least the first region of the first and second regions, and the second film is disposed so as to overlap the second region. [8A] The conductive film according to [7A], wherein the conductive material contains silver. [9A] An optoelectronic device having the conductive film according to [7A] or [8A]. [10A] The optoelectronic device according to [9], comprising: a substrate; an anode provided on the substrate; a cathode provided on the substrate; and an active layer disposed between the anode and the cathode, wherein the cathode is the conductive film. [11A] A method for producing a conductive film, comprising depositing a compound of any one of [1A] to [6A] on a substrate through a mask to form a second film containing the compound, and depositing a conductive material on the second film. [12A] The method for producing a conductive film according to [11A], wherein the conductive material contains silver.

[0181] The present disclosure will be described in more detail below with reference to examples and comparative examples, but the present disclosure is not limited to the following examples as long as it does not deviate from the gist of the disclosure. Examples 1 to 20 are examples, and Examples 21 to 25 are comparative examples.

[0182] [Synthesis of Compounds] (Example 1) Compound 1-1 was produced by the following procedure.

[0183]

[0184] 1.03 g (1.63 mmol) of 4,4',4",4'''-[(1-Methylethylidene)di-4-cyclohexanyl-1-ylidene]tetrakis[2-ethylphenol] (manufactured by Honshu Chemical Industry Co., Ltd., hereinafter also referred to as "tekOC-4HBPA") was weighed into a 50 mL two-neck round-bottom flask and dissolved in a mixed solvent of 7 mL of N,N-dimethylformamide (hereinafter also referred to as "DMF") and 2 mL of 2-propanol. 1.1 g (8 mmol) of potassium carbonate was added, and the mixture was suspended by stirring. 2.7 mL (16 mmol) of perfluoropropoxyethylene was added, and the mixture was stirred at 25°C for 12 hours. After separation with water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 2.15 g of Compound 1-1 as a colorless glassy solid (yield 78%). The identification data of Compound 1-1 are shown below. １ H-NMR (acetone-D6): δ7.5-6.9 (m, 16H), 2.8 (m, 4H), 2.3 (s, 6H), 2.2 (s, 6H), 1.9 (m, 4H), 1.7 (m, 4H), 1.5 (m, 2H), 1.2 (m, 4H), 0.5 (s, 6H) １９ F-NMR (acetone-D6): δ-82 (s, 12F), -86 (m, 16F), -131 (s, 8F), -146 (m, 4F)

[0185] Example 2 Compound 1-2 was prepared according to the following procedure.

[0186]

[0187] 1.05 g (1.66 mmol) of tekOC-4HBPA was weighed into a 50 mL two-neck round-bottom flask and dissolved in a mixed solvent of 7 mL of DMF and 2 mL of 2-propanol. 1.1 g (8 mmol) of potassium carbonate was added and the mixture was suspended by stirring. The neck of the flask was sealed with a septum, and perfluoromethyl vinyl ether, which had been placed in a 3 L Tedlar bag, was connected via a syringe and stirred at 25°C for 12 hours. After separation with water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 1.51 g of compound 1-2 as a colorless glassy solid (yield 70%). The identification data for compound 1-2 are shown below. １ H-NMR (acetone-D6): δ7.5-7.1 (m, 12H), 6.9-6.7 (m, 4H), 2.8 (m, 4H), 2.3 (s , 6H), 2.2 (s, 6H), 1.9 (m, 4H), 1.7 (m, 4H), 1.5 (m, 2H), 1.2 (m, 4H), 0.5 (s, 6H) １９ F-NMR (acetone-D6): δ-60 (s, 12F), -86 (m, 8F), -146 (m, 4F)

[0188] Example 3 Compound 1-3 was prepared according to the following procedure.

[0189]

[0190] 2.00 g (3.5 mmol) of 4,4',4",4'''-[(1-Methylethylidene)di-4-cyclohexanyl-1-ylidene]tetrakisphenol (manufactured by Honshu Chemical Industry Co., Ltd., hereinafter also referred to as "tekP-4HBPA") was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 14 mL of DMF and 4 mL of 2-propanol. 2.4 g (17 mmol) of potassium carbonate was added, and the mixture was stirred to form a suspension. 7.1 mL (42 mmol) of perfluoropropoxyethylene was added, and the mixture was stirred at 25°C for 12 hours. After separation with water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 4.27 g of Compound 1-3 as a colorless glassy solid (yield 75%). The identification data for Compound 1-3 are shown below. １ H-NMR (acetone-D6): δ7.6 (m, 4H), 7.4 (m, 4H), 7.3 (m, 4H), 7.2 (m, 4H), 7.0 to 6.8 (m, 4H), 2.8 (m, 4H), 1.9 (m, 4H), 1.7 (m, 4H), 1.5 (m, 2H), 1.2 (m, 4H), 0.5 (s, 6H) １９ F-NMR (acetone-D6): δ-82 (s, 12F), -86 (m, 16F), -130 (s, 8F), -146 (m, 4F)

[0191] Example 4 Compound 1-4 was prepared according to the following procedure.

[0192]

[0193] 2.00 g (3.5 mmol) of tekP-4HBPA was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 14 mL of DMF and 3.5 mL of 2-propanol. 2.4 g (17 mmol) of potassium carbonate was added and the mixture was stirred to form a suspension. The neck of the flask was sealed with a septum, and perfluoromethyl vinyl ether, which had been placed in a 5 L Tedlar bag, was connected via a syringe and stirred at 25°C for 12 hours. After a separation operation using water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 2.80 g of compound 1-4 as a colorless glassy solid (yield 65%). The identification data for compound 1-4 are shown below. １ H-NMR (acetone-D6): δ7.6 (m, 4H), 7.4 (m, 4H), 7.3 (m, 4H), 7.2 (m, 4H), 6.8 to 6.6 (m, 4H), 2.8 (m, 4H), 1.9 (m, 4H), 1.7 (m, 4H), 1.5 (m, 2H), 1.2 (m, 4H), 0.5 (s, 6H) １９ F-NMR (acetone-D6): δ-60 (s, 12F), -86 (m, 8F), -146 (m, 4F)

[0194] Example 5 Compound 1-5 was prepared according to the procedure shown below.

[0195]

[0196] 2.80 g (3.5 mmol) of 4,4',4'',4''-(propane-2,2-diylbis(cyclohexane-4,1,1-triyl))tetrakis(2-(tert-butyl)phenol) (manufactured by Honshu Chemical Industry Co., Ltd., hereinafter also referred to as "tekOTBP-4HBPA") was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 14 mL of DMF and 3.5 mL of 2-propanol. 2.4 g (17 mmol) of potassium carbonate was added and the mixture was stirred to form a suspension. The neck of the flask was sealed with a septum, and perfluoromethyl vinyl ether, which had been placed in a 5 L Tedlar bag, was added via a syringe. The mixture was stirred at 25°C for 12 hours. After separation with water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 3.08 g of Compound 1-5 as a colorless glassy solid (yield 60%). The identification data of Compound 1-5 are shown below. １ H-NMR (CDCl ３ ): δ7.5 to 6.9 (m, 12H), 6.1 to 5.8 (m, 4H), 2.6 (m, 4H), 1.9 (m, 4H), 1.6 (m, 4H), 1.5 to 1.1 (m, 42H), 0.5 (s, 6H) １９ F-NMR (CDCl ３ ): δ-57 (s, 12F), -82 (m, 8F), -142 (m, 4F)

[0197] Example 6 Compound 1-6 was prepared according to the following procedure.

[0198]

[0199] 2.80 g (3.5 mmol) of tekOTBP-4HBPA was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 14 mL of DMF and 4 mL of 2-propanol. 2.4 g (17 mmol) of potassium carbonate was added and the mixture was suspended by stirring. 7.1 mL (42 mmol) of perfluoropropoxyethylene was added and the mixture was stirred at 25°C for 12 hours. After a separation operation using water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 3.59 g of compound 1-6 as a colorless glassy solid (yield 70%). The identification data for compound 1-6 are shown below. １ H-NMR (CDCl ３ ): δ7.5 to 6.9 (m, 12H), 6.1 to 5.8 (m, 4H), 2.6 (m, 4H), 1.9 (m, 4H), 1.6 (m, 4H), 1.5 to 1.1 (m, 42H), 0.5 (s, 6H) １９ F-NMR (CDCl ３ ): δ-79 (m, 12F), -81 to -85 (m, 16F), -127 (s, 8F), -140 (m, 4F)

[0200] Example 7 Compound 1-7 was prepared according to the following procedure.

[0201]

[0202] A nitrogen-purged two-neck flask was charged with 2.5 g (63 mmol) of sodium hydride (60% by mass in oil) and 40 mL of dioxane, followed by the slow addition of a dioxane solution of 5.0 g (7.9 mmol) of tekOC-4HBPA. The mixture was then cooled to 0°C, and 6.2 g (47 mmol) of chlorodifluoroacetic acid was slowly added. The mixture was then heated to 100°C and stirred for 24 hours. After cooling to 25°C, the reaction solution was added dropwise to a saturated aqueous ammonium chloride solution to terminate the reaction. The pH was adjusted to 1 by adding hydrochloric acid, and the pH was adjusted to 8 by adding sodium bicarbonate. After washing with dichloromethane, the pH was adjusted to 1 by adding hydrochloric acid, and the mixture was extracted with dichloromethane. The mixture was dried over magnesium sulfate and then concentrated under reduced pressure to obtain 8.5 g of crude compound 7a. The crude product was used in the next step. A nitrogen-purged two-neck flask was charged with 22.4 g (63 mmol) of Selectfluor, 1.6 g (6.3 mmol) of silver trifluoromethanesulfonate, 8.5 g of the crude product of Compound 7a, 36 mL of dichloromethane, 4 mL of water, and 14 g (126 mmol) of trifluoroacetic acid, and the mixture was heated and stirred at 55°C for 8 hours. After completion of the reaction, the mixture was allowed to cool to 25°C, and water was added for liquid separation. The resulting organic layer was washed sequentially with water and saturated brine. The mixture was dried over magnesium sulfate, then evaporated under reduced pressure, and purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), yielding 1.1 g of Compound 1-7 (yield 15%). Identification data for Compound 1-7 are shown below. １ H-NMR (CDCl ３ ): δ7.2 to 6.8 (m, 12H), 2.7 to 2.5 (m, 4H), 2.2 (s, 6H), 2.1 (s, 6H), 1.9 to 1.7 (m, 4H), 1.6 to 1.5 (m, 4H), 1.4 to 1.3 (m, 2H), 1.3 to 1.1 (m, 4H), 0.5 (s, 6H) 　１９ F-NMR (CDCl ３ ): δ-41 (s, 6F), -42 (s, 6F)

[0203] Example 8 Compound 1-8 was prepared according to the following procedure.

[0204]

[0205] 1.0 g (1.6 mmol) of tekOC-4HBPA was weighed into a 50 mL two-neck round-bottom flask and dissolved in 8 mL of DMF. 6.3 g (19 mmol) of cesium carbonate and 3.7 g (19 mmol) of 1-bromo-3-(trifluoromethoxy)propane were added, and the mixture was stirred at 70°C for 12 hours. After a water / ethyl acetate separation operation, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 0.61 g of compound 1-8 (yield 35%). Identification data for compound 1-8 are shown below. １ H-NMR (CDCl ３ ): δ7.2-6.4 (m, 12H), 4.4-4.1 (m, 8H), 4.0-3.7 (m, 8H), 2.7-2.5 (m, 4H), 2.2 (s, 6H), 2. 1 (s, 6H), 1.9-1.7 (m, 4H), 1.6-1.5 (m, 4H), 1.4-1.3 (m, 2H), 1.3-1.1 (m, 4H), 0.5 (s, 6H) １９ F-NMR (CDCl ３ ): δ-59 (s, 6F), -60 (s, 6F)

[0206] Example 9 Compound 1-9 was prepared according to the following procedure.

[0207]

[0208] <Synthesis of Compounds 9a, 9b, and 9c> Compounds 9c, 9d, and 9e were synthesized by the method described in Tetrahedron 2007, 63, 3982-3988.

[0209] <Synthesis of Compound 9d> In a glove box under a nitrogen atmosphere, 1.0 g (4.4 mmol) of compound 9c, 17 g (66 mmol) of silver trifluoromethanesulfonate, 9.4 g (27 mmol) of SelectFluor (registered trademark), 12 g (80 mmol) of cesium fluoride, 8.4 g (27 mmol) of N-fluorobenzenesulfonimide, and 90 g (972 mmol) of toluene were added to a 300 mL recovery flask and stirred. 6.4 g (66 mmol) of 2-fluoropyridine and 9.4 g (66 mmol) of trifluoromethyltrimethylsilane were added to this mixture and stirred for 16 hours. After completion of the reaction, the reaction solution was passed through 30 g of silica gel and eluted with ethyl acetate. The resulting solution was concentrated under reduced pressure and then purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain compound 9d (1.4 g, 74% yield). Identification data for compound 9d are shown below. １ H-NMR (CDCl ３ ) δ7.4-7.2 (m, 5H), 4.5 (s, 2H), 4.1 (s, 6H), 3.5 (2, 2H) 　１９ F-NMR (CDCl ３ ): δ-59(s, 9F)

[0210] <Synthesis of Compound 9e> 1.4 g (3.3 mmol) of compound 9d and 20 mL of methanol were added to a 100 mL recovery flask, and 1.4 g of Pd / C (palladium carbon with a palladium content of 5% by mass) (hydrated) was added under a nitrogen atmosphere. The atmosphere in the flask was then replaced with hydrogen three times, and the mixture was stirred at 25°C for 16 hours. The Pd / C was then removed by filtration through Celite, the filtrate was evaporated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1.0 g of compound 9e (yield 90%). Identification data for compound 9e are shown below. １ H-NMR (CDCl ３ ): δ4.1 (s, 6H), 3.8 (d, 2H), 1.6 (t, 1H) 　１９ F-NMR (CDCl ３ ): δ-59(s, 9F)

[0211] <Synthesis of Compound 1-9> 1.0 g (1.6 mmol) of tekOC-4HBPA, 2.5 g (9.6 mmol) of triphenylphosphine, 6 mL of tetrahydrofuran (THF), 1 g of molecular sieves 4 Å, and 3.3 g (9.6 mmol) of compound 9d were added to a 25 mL vial and stirred at 0°C. 4.4 mL of diethyl azodicarboxylate (DEAD) (2.2 M toluene solution) was added thereto and sealed, followed by heating and stirring at 45°C for 24 hours. After cooling to 25°C, THF was added, the mixture was filtered, and concentrated under reduced pressure to obtain a crude product. This was purified by silica gel column chromatography (hexane) to obtain 1.1 g of compound 1-9 (yield 35%). Identification data for compound 1-9 are shown below. １ H-NMR (CDCl ３ ): δ7.2-6.4 (m, 12H), 4.2-4.0 (m, 8H), 3.8-3.5 (m, 24H), 2.7-2.5 (m, 4H), 2.2 (s, 6H), 2. 1 (s, 6H), 1.9-1.7 (m, 4H), 1.6-1.5 (m, 4H), 1.4-1.3 (m, 2H), 1.3-1.1 (m, 4H), 0.5 (s, 6H) １９ F-NMR (CDCl ３ ): δ-59 (s, 18F), -60 (s, 18F)

[0212] Example 10 Compound 1-10 was prepared according to the following procedure.

[0213]

[0214] 1.0 g (1.6 mmol) of tekOC-4HBPA was weighed into a 50 mL two-neck round-bottom flask and dissolved in 8 mL of DMF. 6.3 g (19 mmol) of cesium carbonate and 2.3 g (9.6 mmol) of 2-bromoethylsulfur pentafluoride were added, and the mixture was stirred at 70°C for 12 hours. After a water / ethyl acetate separation, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 0.60 g of compound 1-10 (yield 30%). The identification data for compound 1-10 are shown below. １ H-NMR (CDCl ３): δ7.2-6.4 (m, 12H), 4.3-4.0 (m, 8H), 3.7-3.1 (m, 8H), 2.7-2.5 (m, 4H), 2.2 (s, 6H), 2. 1 (s, 6H), 1.9-1.7 (m, 4H), 1.6-1.5 (m, 4H), 1.4-1.3 (m, 2H), 1.3-1.1 (m, 4H), 0.5 (s, 6H) １９ F-NMR (CDCl ３ ): δ88-83 (m, 4F), 70-68 (m, 16F)

[0215] Example 11 Compound 1-11 was prepared according to the following procedure.

[0216]

[0217] <Synthesis of Compound 11a> 10.0 g (15.8 mmol) of tekOC-4HBPA was weighed into a 500 mL two-neck round-bottom flask and dissolved in 300 mL of acetone. 21.6 g (157 mmol) of potassium carbonate was added and the mixture was stirred to form a suspension. 11.5 mL (126 mmol) of allyl iodide was added and the mixture was stirred at 80°C for 12 hours. After filtering off the solid, the filtrate was concentrated and subjected to a liquid separation operation with water / ethyl acetate. After purification by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), 9.89 g of compound 11a was obtained as a white solid (yield 79%). Identification data for compound 11a are shown below. １ H-NMR (CDCl ３ ): δ7.2-6.6 (m, 12H), 6.2-5.9 (m, 4H), 5.5-5.1 (m, 8H), 4.6-4.4 (m, 8H), 2.6 (m, 4H) , 2.2 (s, 6H), 2.1 (s, 6H), 1.8 (m, 4H), 1.6 (m, 4H), 1.4 (m, 2H), 1.2 (m, 4H), 0.5 (s, 6H)

[0218] <Synthesis of Compound 1-11> 2.0 g (2.5 mmol) of compound 11a was weighed into a three-neck flask and dissolved in 5 mL of dichloromethane. 2 mg (0.03 mmol) of aniline and 6.7 g (30 mmol) of 1,1,1,3,3,5,5-heptamethyltrisiloxane were added and stirred. Then, 0.3 g (0.03 mmol) of a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass) was added and stirred at 25°C for 24 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 99 / 1), yielding 1.6 g of compound 1-11 (yield: 40%). Identification data for compound 1-11 are shown below. １ H-NMR (CDCl ３ ): δ7.2 to 6.5 (m, 12H), 4.0 to 3.8 (m, 8H), 2.7 to 2.5 (m, 4H), 2.2 (s, 6H), 2.1 (s, 6H), 1.9 to 1.7 (m, 12H) , 1.6-1.5 (m, 4H), 1.4-1.3 (m, 2H), 1.3-1.1 (m, 4H), 1.0-0.8 (m, 8H), 0.5 (s, 6H), 0.2-0.0 (m, 84H)

[0219] Example 12 Compound 1-12 was prepared according to the following procedure.

[0220]

[0221] 5.0 g (6.3 mmol) of compound 11a was weighed into a three-neck flask and dissolved in 10 mL of dichloromethane. 6 mg (0.06 mmol) of aniline and 23 g (75 mmol) of tris(trimethylsilyloxy)silane were added and stirred. Then, 0.80 g (0.06 mmol) of a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass) was added and stirred at 25°C for 24 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 99 / 1). The solvent was then removed under reduced pressure to obtain 5.4 g of compound 1-12 (yield: 43%). Identification data for compound 1-12 are shown below. １ H-NMR (CDCl３ ): δ7.2 to 6.5 (m, 12H), 4.0 to 3.8 (m, 8H), 2.7 to 2.5 (m, 4H), 2.2 (s, 6H), 2.1 (s, 6H), 1.9 to 1.7 (m, 12H), 1.6 to 1.5 (m, 4H), 1.4-1.3 (m, 2H), 1.3-1.1 (m, 4H), 0.7-0.5 (m, 8H), 0.5 (s, 6H), 0.10 (s, 54H), 0.09 (s, 54H)

[0222] Example 13 Compound 1-13 was prepared according to the following procedure.

[0223]

[0224] 2.0 g (2.5 mmol) of compound 11a was weighed into a three-neck flask and dissolved in 5 mL of dichloromethane. 2 mg (0.03 mmol) of aniline and 8.5 g (30 mmol) of heptamethylcyclotetrasiloxane were added and stirred. Then, 0.3 g (0.03 mmol) of a toluene solution of platinum / 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (platinum content: 3% by mass) was added and stirred at 25°C for 24 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 99 / 1). The solvent was then removed under reduced pressure to obtain 2.3 g of compound 1-13 (yield: 48%). Identification data for compound 1-13 are shown below. １ H-NMR (CDCl ３ ): δ7.2 to 6.5 (m, 12H), 4.0 to 3.8 (m, 8H), 2.7 to 2.5 (m, 4H), 2.2 (s, 6H), 2.1 (s, 6H), 1.9 to 1.7 (m, 12H) , 1.6-1.5 (m, 4H), 1.4-1.3 (m, 2H), 1.3-1.1 (m, 4H), 1.0-0.8 (m, 8H), 0.5 (s, 6H), 0.2-0.0 (m, 84H)

[0225] Example 14 Compound 1-14 was prepared according to the following procedure.

[0226]

[0227] 5.0 g (7.9 mmol) of tekOC-4HBPA, 14.6 g (63 mmol) of potassium carbonate, 15.8 g (47 mmol) of 1-bromooctane, and 40 mL of N,N-dimethylformamide were mixed in a three-neck flask and stirred at 80°C under a nitrogen atmosphere for 6 hours. The solid was separated by filtration, and then the mixture was separated with water / ethyl acetate. The mixture was then purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 99 / 1) to obtain 5.2 g of compound 1-14 (yield 40%). The identification data for compound 1-14 are shown below. １ H-NMR (CDCl3): δ7.2-6.5 (m, 12H), 4.0-3.8 (m, 8H), 2.7-2.5 (m, 4H), 2.2 ( s, 6H), 2.1 (s, 6H), 1.9 to 1.7 (m, 12H), 1.6 to 1.1 (m, 130H), 0.8 to 0.5 (m, 18H)

[0228] Example 15 Compound 1-15 was prepared according to the following procedure.

[0229]

[0230] <Synthesis of Compound 15a> 128.6 g (856 mmol) of 2-tert-butylphenol, 8.0 g (71.3 mmol) of cyclohexanone, and 1.9 g (9.4 mmol) of 1-octanethiol were added to a three-neck flask, the temperature was raised to 50°C, and hydrogen chloride gas was bubbled in for 2 hours. After the bubbling of hydrogen chloride gas was completed, the mixture was stirred at 50°C for 12 hours. After the reaction was completed, nitrogen gas was bubbled in to remove the hydrogen chloride gas from the reactor, and excess 2-tert-butylphenol was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane / ethyl acetate), yielding 40 g of compound 15a (yield 83%). Identification data for compound 15a are shown below. １ H-NMR (Acetone-d6): δ7.2-6.6 (m, 12H), 4.5 (br, 4H), 2.2 (s, 8H), 1.4 (s, 36H)

[0231] <Synthesis of Compound 1-15> 2.4 g (3.5 mmol) of compound 15a was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 14 mL of DMF and 3.5 mL of 2-propanol. 2.4 g (17 mmol) of potassium carbonate was added and the mixture was stirred to form a suspension. The neck of the flask was sealed with a septum, and perfluoromethyl vinyl ether, which had been placed in a 5 L Tedlar bag, was connected via a syringe and stirred at 25°C for 12 hours. After a separation operation using water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 3.1 g of compound 1-15 (yield 65%). Identification data for compound 1-15 are shown below. １ H-NMR (CDCl ３ ): δ7.2 to 6.6 (m, 12H), 6.1 to 5.8 (m, 4H), 2.2 (s, 8H), 1.4 (s, 36H) １９ F-NMR (CDCl ３ ): δ-57 (s, 12F), -82 (m, 8F), -142 (m, 4F)

[0232] Example 16 Compound 1-16 was prepared according to the following procedure.

[0233]

[0234] <Synthesis of Compound 16a> 42.9 g (285 mmol) of 2-tert-butylphenol, 3.3 g (23.8 mmol) of tetrahydropentalene-2,5-dione, and 0.63 g (3.1 mmol) of 1-octanethiol were placed in a three-neck flask, heated to 50°C, and hydrogen chloride gas was bubbled in for 2 hours. After the bubbling of hydrogen chloride gas was completed, the mixture was stirred at 50°C for 12 hours. After the reaction was completed, nitrogen gas was bubbled in to remove the hydrogen chloride gas from the reactor, and excess 2-tert-butylphenol was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain 13 g of compound 16a (yield 79%). Identification data for compound 16a are shown below. １H-NMR (Acetone-d6): δ7.2 to 6.7 (m, 12H), 4.5 (br, 4H), 2.4 to 1.7 (m, 10H), 1.4 (s, 36H)

[0235] <Synthesis of Compound 1-16> 2.5 g (3.5 mmol) of compound 16a was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 14 mL of DMF and 3.5 mL of 2-propanol. 2.4 g (17 mmol) of potassium carbonate was added and the mixture was stirred to form a suspension. The neck of the flask was sealed with a septum, and perfluoromethyl vinyl ether, which had been placed in a 5 L Tedlar bag, was connected via a syringe and stirred at 25°C for 12 hours. After a separation operation using water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 3.2 g of compound 1-16 (yield 67%). Identification data for compound 1-16 are shown below. １ H-NMR (CDCl ３ ): δ7.2-6.7 (m, 12H), 6.1-5.8 (m, 4H), 2.4-1.7 (m, 10H), 1.4 (s, 36H) １９ F-NMR (CDCl ３ ): δ-57 (s, 12F), -82 (m, 8F), -142 (m, 4F)

[0236] Example 17 Compound 1-17 was prepared according to the following procedure.

[0237]

[0238] <Synthesis of Compound 17a> 3.8 g (20 mmol) of 2-cyclohexyl-5-methylphenol, 2.5 g (15 mmol) of 1,3-adamandiol, and 1.0 g (10 mmol) of concentrated sulfuric acid were placed in a three-neck flask and stirred at 90°C for 3 hours. After completion of the reaction, the mixture was allowed to cool to 25°C, 40 g of acetone was added, and an aqueous sodium hydroxide solution was added at 0°C to adjust the pH to 7, followed by stirring for 1 hour. After a separation operation with water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), yielding 5.0 g of Compound 17a (yield 65%). Identification data for Compound 17a are shown below. １H-NMR (Acetone-d6): δ7.1 (s, 2H), 7.0 (s, 2H), 4.5 (br, 2H), 2.9 (m, 2H), 2.6 (s, 2H), 2.3 (m, 7H), 2.2 to 1.4 (m, 31H)

[0239] <Synthesis of Compound 1-17> 1.8 g (3.5 mmol) of compound 17a was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 14 mL of DMF and 3.5 mL of 2-propanol. 2.4 g (17 mmol) of potassium carbonate was added and the mixture was stirred to form a suspension. 7.1 mL (42 mmol) of perfluoropropoxyethylene was added and stirred at 25°C for 12 hours. After a separation operation using water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 1.8 g of compound 1-17 (yield 60%). Identification data for compound 1-17 are shown below. １ H-NMR (CDCl ３ ): δ7.1 (s, 2H), 7.0 (s, 2H), 6.1 to 5.8 (m, 2H), 2.9 (m, 2H), 2.6 (s, 2H), 2.3 (m, 7H), 2.2 to 1.4 (m, 31H) １９ F-NMR (CDCl ３ ): δ-79 (m, 6F), -81 to -85 (m, 8F), -127 (s, 4F), -140 (m, 2F)

[0240] Example 18 Compound 3-1 was prepared according to the following procedure.

[0241]

[0242] 1.2 g (1.7 mmol) of 4,4',4",4'"-(1,2-Ethanediylidene)tetrakis[2-cyclohexylphenol] was weighed into a 50 mL two-necked round-bottom flask and dissolved in a mixed solvent of 7 mL of DMF and 2 mL of 2-propanol. 1.1 g (8 mmol) of potassium carbonate was added and the mixture was suspended by stirring. The neck of the flask was sealed with a septum, and perfluoromethyl vinyl ether, which had been placed in a 3 L Tedlar bag, was added via a syringe. The mixture was stirred at 25°C for 12 hours. After separation with water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5). The solvent was removed under reduced pressure to obtain 1.5 g of compound 3-1 as a colorless glassy solid (yield 65%). The identification data for compound 3-1 are shown below. １ H-NMR (CDCl ３ ): δ7.1 to 6.8 (m, 12H), 6.1 to 5.8 (m, 4H), 4.5 (s, 2H), 2.7 (m, 4H), 1.7 to 1.2 (m, 40H) １９ F-NMR (CDCl ３ ): δ-57 (s, 12F), -82 (m, 8F), -142 (m, 4F)

[0243] Example 19 Compound 2-3 was prepared according to the following procedure.

[0244]

[0245] A three-neck flask was charged with 4.3 g (43 mmol) of 2-hydroxythiophene, 0.40 g (3.6 mmol) of cyclohexanone, and 0.1 g (0.5 mmol) of 1-octanethiol. The mixture was heated to 50°C and hydrogen chloride gas was bubbled in for 2 hours. After the hydrogen chloride gas bubbling was completed, the mixture was stirred at 50°C for 12 hours. After the reaction was completed, nitrogen gas was bubbled in to remove the hydrogen chloride gas from the reactor, and excess 2-hydroxythiophene was distilled off under reduced pressure to obtain 1.8 g of crude compound 19a. This crude product was used in the next step. 1.8 g of crude compound 19a was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 14 mL of DMF and 3.5 mL of 2-propanol. 2.4 g (17 mmol) of potassium carbonate was added, and the mixture was suspended by stirring. The neck of the flask was sealed with a septum, and perfluoromethyl vinyl ether, which had been dispensed into a 5 L Tedlar bag, was connected via a syringe and stirred at 25°C for 12 hours. After a separation operation using water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 1.4 g of compound 1-19 (yield 35%). The identification data for compound 1-19 are shown below. １ H-NMR (CDCl ３ ): δ6.5-6.4 (m, 8H), 6.0-5.7 (m, 4H), 2.2 (s, 8H) １９ F-NMR (CDCl ３ ): δ-59 (s, 12F), -84 (m, 8F), -144 (m, 4F)

[0246] Example 20 Compound 1-18 was prepared according to the following procedure.

[0247]

[0248] <Synthesis of Compound 18a> 43 g (400 mmol) of 2-methylphenol, 5.6 g (50 mmol) of cyclohexanone, and 1.0 g (5 mmol) of 1-octanethiol were added to a three-neck flask, the temperature was raised to 50°C, and hydrogen chloride gas was bubbled in for 2 hours. After the bubbling of hydrogen chloride gas was completed, the mixture was stirred at 50°C for 12 hours. After the reaction was completed, nitrogen gas was bubbled in to remove the hydrogen chloride gas from the reactor, and excess 2-methylphenol was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane / ethyl acetate) to obtain 22 g of compound 18a (yield 85%). Identification data for compound 18a are shown below. １ H-NMR (Acetone-d6): δ7.2 to 6.6 (m, 12H), 4.5 (br, 4H), 2.2 (s, 8H), 2.1 (s, 12H)

[0249] <Synthesis of Compound 1-18> 0.82 g (1.6 mmol) of compound 18a was weighed into a 50 mL two-neck round-bottom flask and dissolved in 8 mL of DMF. 6.3 g (19 mmol) of cesium carbonate and 3.7 g (19 mmol) of 1-bromo-3-(trifluoromethoxy)propane were added, and the mixture was stirred at 70°C for 12 hours. After a separation operation using water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure, yielding 0.61 g of compound 1-18 (yield 40%). Identification data for compound 1-18 are shown below. １ H-NMR (CDCl3): δ7.2-6.6 (m, 12H), 4.4-4.1 (m, 8H), 4.0-3.7 (m, 8H), 2.2 (s, 8H), 2.1 (s, 12H) １９ F-NMR (CDCl3): δ-59 (s, 12F)

[0250] Example 21 Compound 4 was prepared according to the following procedure.

[0251]

[0252] 3.0 g (3.5 mmol) of α,α,α',α'-tetrakis(4-hydroxyphenyl)-4,4'-diethylbiphenyl (Honshu Chemical Industry Co., Ltd., product name tekOC-DABP) was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 14 mL of DMF and 4.0 mL of 2-propanol. 2.6 g (19 mmol) of potassium carbonate was added and the mixture was suspended by stirring. The neck of the flask was sealed with a septum, and perfluoromethyl vinyl ether, which had been placed in a 5 L Tedlar bag, was added via a syringe and stirred at 25°C for 12 hours. After a liquid separation operation with water / ethyl acetate, the residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate=95 / 5), and the solvent was removed under reduced pressure to obtain 4.10 g of compound 4 as a colorless glassy solid (yield 89%).

[0253] Example 22 Compound 5 was prepared according to the following procedure.

[0254]

[0255] 2.0 g (4.0 mmol) of α,α,α',α'-tetrakis(4-hydroxyphenyl)-1,4-diethylbenzene (Honshu Chemical Industry Co., Ltd., product name tekP-DAB) was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 16 mL of DMF and 4.0 mL of 2-propanol. 2.9 g (21 mmol) of potassium carbonate was added and the mixture was stirred to form a suspension. The neck of the flask was sealed with a septum, and perfluoromethyl vinyl ether, which had been separated into a 5 L Tedlar bag, was added via a syringe. The mixture was stirred at 25°C for 12 hours. After a water / ethyl acetate separation, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 95 / 5), and the solvent was removed under reduced pressure to obtain 4.60 g of compound 5 as a colorless glassy solid (yield 98%).

[0256] Example 23 Compound 6 was prepared according to the following procedure.

[0257]

[0258] 1.00 g (2.85 mmol) of 9,9-Bis(4-hydroxyphenyl)fluorene (Tokyo Chemical Industry Co., Ltd.) was weighed into a 100 mL two-neck round-bottom flask and dissolved in a mixed solvent of 12 mL of DMF and 3 mL of 2-propanol. 0.99 g (7.16 mmol) of potassium carbonate was added and the mixture was stirred to form a suspension. 2.5 mL (15 mmol) of perfluoropropoxyethylene was added and stirred at 25°C for 12 hours. After a separation operation with water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 9 / 1), and the solvent was removed under reduced pressure to obtain 1.76 g of compound 6 as a white solid (yield 70%).

[0259] Example 24 Compound 7 was prepared according to the procedure shown below.

[0260]

[0261] 0.7 g (1.73 mmol) of 4,4',4",4'''-Methanetetrayltetraphenol (Tokyo Chemical Industry Co., Ltd.) was weighed into a 50 mL two-neck round-bottom flask and dissolved in a mixed solvent of 7 mL of DMF and 2.0 mL of 2-propanol. 1.19 g (8.6 mmol) of potassium carbonate was added and the mixture was stirred to form a suspension. The neck of the flask was sealed with a septum, and perfluoromethyl vinyl ether, which had been placed in a 3 L Tedlar bag, was added via a syringe. The mixture was stirred at 25°C for 12 hours. After a separation with water / ethyl acetate, the mixture was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate = 9 / 1). The solvent was removed under reduced pressure to obtain 1.51 g of compound 7 as a colorless glassy solid (yield 79%).

[0262] Example 25 Compound 8 was prepared according to the procedure described in Example 1 of WO 2022 / 034907.

[0263]

[0264] [Evaluation] The compounds of the examples were evaluated as follows.

[0265] (Evaluation of Vapor Deposition Properties) The thermal mass loss rate of the compound under vacuum was measured using a vacuum differential thermobalance (VPE-9000 manufactured by Advance Riko Co., Ltd.). Specifically, 50 mg of the compound was placed in a cell with an inner diameter of 7 mm, and 1×10 －３ The mass loss rate of the compound was evaluated when the temperature was raised from 50°C to 500°C at a rate of 2°C per minute at a vacuum of 100 Pa or less. Compounds that showed a mass loss of 95% or more in the range of 150°C to 300°C were classified as "vapor-depositable," while compounds that did not meet this condition were classified as "vapor-not vapor-depositable." As a result, all of the compounds in Examples 1 to 25 were "vapor-depositable."

[0266] (Preparation of substrate with organic film) Using a vapor deposition apparatus, a compound was vapor-deposited onto the surface of a 25 mm x 25 mm x 0.525 mm quartz substrate through a metal mask with a 25 mm x 12 mm opening, to prepare a quartz substrate with an organic film containing the compound (hereinafter also referred to as "substrate with organic film"). The compound was vapor-deposited at a vapor deposition rate of 0.1 nm / sec. The compound was vapor-deposited until the film thickness measured by a film thickness meter attached to the vapor deposition apparatus reached 50 nm.

[0267] (Evaluation of film formability: measurement of total light transmittance and haze) For the above organic film-coated substrates, the total light transmittance and haze of the portions where the organic film was deposited were measured using a haze meter (manufactured by Suga Test Instruments, model number: HZ-V3, measuring light: D65 light). The results are shown in Tables 1 to 3. In Examples 1 to 20, the total light transmittance of the portions where the organic film was deposited was 93% or more, and the haze was 1.0 or less. These results confirmed that the deposited films formed from the compounds of Examples 1 to 20 were colorless, transparent, and uniform films. On the other hand, in Examples 23 and 24, the haze of the portions where the organic film was deposited exceeded 1.0, confirming that the deposited films were non-uniform films.

[0268] (Ag Vapor Deposition) Using a vapor deposition system, Ag was vapor-deposited onto the entire surface of the organic film-coated substrate without using a mask. The Ag vapor deposition was carried out at a vapor deposition rate of 0.05 nm / sec. The Ag vapor deposition was continued until the thickness reached 70 nm as measured by a film thickness meter attached to the vapor deposition system.

[0269] (Evaluation of Ag Repellency: Transmittance Measurement) For the organic film-coated substrates before and after Ag deposition, the transmittance of the organic film-deposited portion at wavelengths of 300 to 800 nm was measured using a spectrophotometer (Shimadzu Corporation, Model No. UV-3600 Plus) with a quartz substrate as a reference. Tables 1 to 3 show the transmittance at a wavelength of 436 nm for each example. Figures 9 to 17 show the transmittance spectra at wavelengths of 300 to 800 nm for Examples 1 to 4 and 21 to 25, respectively. In Examples 1 to 20, even after Ag deposition, the transmittance at a wavelength of 436 nm of the organic film-deposited portion was 55% or higher, indicating excellent blue light transmittance. Examples 1 to 6, 9, 15 to 17, and 19 had transmittances of 65% or higher, indicating even better blue light transmittance. Examples 1 to 4 and 6 had transmittances of 80% or higher, indicating even better blue light transmittance. These results confirmed that the vapor-deposited films formed from the compounds of Examples 1 to 20 had excellent Ag repellency. It was also confirmed that the vapor-deposited films formed from the compounds of Examples 1 to 6, 9, 15 to 17, and 19 had even better Ag repellency. It was also confirmed that the vapor-deposited films formed from the compounds of Examples 1 to 4 and 6 had even better Ag repellency. On the other hand, in Examples 21 to 25, after Ag deposition, the transmittance at a wavelength of 436 nm in the portion where the organic film was deposited was less than 55%.

[0270]

[0271]

[0272]

[0273] 1, 2, 3...conductive film, 10, 13, 116...first film, 10A, 13A...first region, 10B, 13B...second region, 10X...conductive material, 15, 117...second film, 20, 118...third film, 20a, 50a...surface, 50...base material, 110...substrate, 111...anode, 115...cathode, P...compound, M...mask

Claims

1. A compound having a molecular weight of 500 to 5,000, composed of hydrogen atoms, carbon atoms, and heteroatoms, wherein the heteroatom is at least one selected from oxygen atoms, sulfur atoms, fluorine atoms, and silicon atoms, having one or more alicyclic structures, one or more aromatic ring structures directly bonded to the alicyclic structure, and one or more monovalent substituents Ms directly bonded to the aromatic ring structure, and the monovalent substituent Ms is at least one selected from a group containing a monovalent fluorine-containing aliphatic group, a group containing a monovalent sulfur fluoride-containing group, a group containing a monovalent siloxanyl group, and a group containing a monovalent saturated hydrocarbon group.

2. The compound according to claim 1, wherein the number of the alicyclic structures is two or more.

3. The compound according to claim 1, wherein the alicyclic structure is monocyclic.

4. The compound according to claim 1, wherein the group containing the monovalent fluorine-containing aliphatic group is represented by the following formula f1. -Z １ -(O-R １ ) ｎ -F Formula f1 However, R １ is an alkylene group or a fluoroalkylene group, n is an integer of 12 or more, and n R １ may be the same as or different from each other, and Z １ is a single bond or a divalent linking group not containing an aromatic ring structure.

5. The compound according to claim 1, wherein the group containing the monovalent fluorine-containing aliphatic group is at least one selected from the groups represented by the following formulas f5 and f6. -Z ２ (-X １ -Rf １ )n1 Formula f5 -Z ３ (-X ２ -Rf ２ -R ２ ) ｎ２ Formula f6 However, Rf １ is -CF ３ , -CF ２ H or -CFH ２ , Rf ２ is -CF ２ - or -CFH-, R ２ is an alkyl group, X １ and X ２ are -O- or -S-, Z ２ and Z ３ are a single bond or a (n1 + 1)-valent or (n2 + 1)-valent linking group containing no aromatic ring structure, and n1 and n2 are integers from 1 to 9.

6. The compound according to claim 1, wherein the monovalent group containing a sulfur fluoride group is at least one selected from the groups represented by the following formulas fs1 and fs2. -Z ４ -SF ５ Formula fs1 -Z ５ -SF ４ -R ３ Formula fs2 However, R ３ is a hydrocarbon group, and Z ４ and Z ５ are a single bond or a divalent linking group not containing an aromatic ring structure.

7. The compound according to claim 1, wherein the group containing the monovalent siloxanyl group is at least one selected from the groups represented by the following formulas sx1 and sx2. However, R ４ are each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms, and Z ６ is a single bond or a divalent linking group not containing an aromatic ring structure, and a, b, c, and d are each independently an integer of 0 to 20, satisfying a + b + c + d > 0. However, R ５ are each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms, and Z ７ is a single bond or a divalent linking group not containing an aromatic ring structure, e is an integer of 1 to 20, f is an integer of 0 to 20, satisfying e + f > 1.

8. The compound according to claim 1, wherein the group containing the monovalent saturated hydrocarbon group is represented by the following formula sh1: -Z ８ -R ６　　　　　　　 Formula sh1 However, R ６ is a saturated hydrocarbon group having 4 to 24 carbon atoms, and Z ８ is a single bond, a divalent linking group not containing an aromatic ring structure, an oxygen atom, or a sulfur atom.

9. The compound according to claim 1, represented by the following formula 1. However, m is an integer from 1 to 8, A is an m-valent group containing one or more of the said alicyclic structures, and Y １ ~Y ５ are each independently the monovalent substituent Ms, a hydrogen atom, a fluorine atom, or an aliphatic group having no monovalent fluorine atom (however, excluding the group containing the monovalent saturated hydrocarbon group), and one or two of the combinations of Y １ and Y ２ , Y ２ and Y ３ , Y ３ and Y ４ , Y ４ and Y ５ may be bonded to each other to form a ring together with the carbon atoms to which they are bonded, and at least one of Y １ ~Y ５ is the monovalent substituent Ms.

10. Y １ to Y ５ The compound according to claim 9, wherein at least one of them is a group containing the monovalent fluorine-containing aliphatic group.

11. The compound according to claim 9, wherein m in the formula 1 is 2 and A is a group represented by the following formula A-1a, or m in the formula 1 is 3 and A is a group represented by the following formula A-2a, or m in the formula 1 is 4 and A is a group represented by the following formula A-3a. However, Z ９ is a single bond or a divalent linking group. *- represents a bond.

12. A conductive film having a first region and a second region having a higher light transmittance than the first region, comprising a first film containing a conductive material and a second film containing the compound according to any one of claims 1 to 11, wherein the first film is disposed so as to overlap at least the first region of the first region and the second region, and the second film is disposed so as to overlap the second region.

13. The conductive film according to claim 12, wherein the conductive material contains silver.

14. An optoelectronic device having the conductive film according to claim 12.

15. An optoelectronic device comprising a substrate, an anode provided on the substrate, a cathode provided on the substrate, and an active layer disposed between the anode and the cathode, wherein the cathode is the conductive film according to claim 14.

16. A method for manufacturing a conductive film, comprising depositing the compound according to any one of claims 1 to 11 through a mask on a substrate to form a second film containing the compound, and depositing a conductive material from above the second film.

17. The method for manufacturing a conductive film according to claim 16, wherein the conductive material contains silver.

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