Charged material, material for electret, charged membrane, electret membrane

Abstract

To provide a material for electrets excellent in light stability, a charged material, and an electret membrane.SOLUTION: Charged materials include compounds that have at least one type selected from aromatic rings and heteroaromatic rings within a molecule, where the ring is substituted with at least one type selected from structures represented by a fluorine atom and formula (A1). A ratio of the number of fluorine atoms to the total number of carbon atoms in the molecule is 30% or more, a molecular weight is between 500 and 4000, and the glass transition temperature is 50°C or higher. In the formula, L1 represents a linear, branched, or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted with O, S, or fluorine atoms, or may represent a vinyl group that can also form a ring and may be substituted with fluorine atoms. In the formula, an independently represents an integer from 0 to 4. In the formula, b independently represents an integer from 1 to 4. In the formula, Rf independently represents a substituent containing three or more fluorine atoms, which is a 1 to 2-valent group with one or more carbon atoms.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to a charged material, an electret material, a charged film, and an electret film.

Background Art

[0002] As a vibration power generation element that converts vibration into electric power, an electrostatic vibration power generation element is known. The electrostatic vibration power generation element is a power generation element configured to change the relative position between an electret (electrified stone) and an electrode by vibration and sequentially induce electrostatic induction in the electrode, and has an advantage that electric power can be efficiently extracted from low-frequency vibration with a small acceleration such as environmental vibration. Regarding the electret of the vibration power generation element, conventionally, research and development have been mainly carried out on polymer-based ones in which charges are implanted into a polymer film. However, since large-scale equipment such as a high-voltage power supply is required in manufacturing and the process is also complicated, there has been a problem that productivity is low and cost is high. Therefore, recently, a vibration power generation element that utilizes the surface potential spontaneously generated in an organic thin film during the film formation process has attracted attention, and research and development of electret materials used for such elements have been actively carried out. As an electret material, Patent Document 1 exemplifies Alq 3 etc. According to Patent Document 1, since a charged film in which a surface potential is spontaneously induced can be formed by laminating on an electrode by a film formation method such as a vapor deposition method or a coating method, it is said that the manufacturing efficiency of the vibration power generation element can be improved and the cost can be reduced.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] However, Alq according to Patent Document 13 The surface potential of the charged film is low in light stability and loses its function due to light irradiation. Therefore, one aspect of the present disclosure is directed to providing a charging material, an electret material, and an electret film capable of forming a charged film excellent in light stability.

Means for Solving the Problems

[0005] According to one aspect of the present disclosure, it has at least one selected from the group consisting of an aromatic ring and a heteroaromatic ring in the molecule, the ring is substituted with at least one selected from the group consisting of a fluorine atom and a structure represented by the following formula (A1), the ratio of the number of fluorine atoms to the number of carbon atoms in the whole molecule is 10% or more, the molecular weight is 500 or more and 4000 or less, and a charging material containing a compound having a glass transition temperature of 50°C or more is provided.

Effects of the Invention

[0006] According to one aspect of the present disclosure, a charging material, an electret material, and an electret film capable of forming a charged film excellent in light stability can be provided.

Brief Description of the Drawings

[0007]

Figure 1

Figure 2

Modes for Carrying Out the Invention

[0008] Hereinafter, the charging material, the electret material, and the electret film according to one aspect of the present disclosure will be described in detail.

[0009] [Charging Material] The charging material according to one aspect of the present disclosure is It has at least one selected from the group consisting of an aromatic ring and a heteroaromatic ring in the molecule, the ring is substituted with at least one selected from the group consisting of a fluorine atom and a structure represented by the following formula (A1), the ratio of the number of fluorine atoms to the number of carbon atoms in the whole molecule is 30% or more, the molecular weight is 500 or more and 4000 or less, and it contains a compound having a glass transition temperature of 50°C or more. Hereinafter, in this specification, the charge-generating material according to the above aspect may be referred to as "charge-generating material A" in some cases.

Chemical formula

[0010] The compound has at least one selected from the group consisting of an aromatic ring and a heteroaromatic ring in the molecule, and the ring is substituted with at least one selected from the group consisting of a fluorine atom and a structure represented by the above formula (A1).

[0011] The aromatic ring is preferably at least one selected from the group consisting of monocyclic, linked-ring, or condensed-ring aromatic hydrocarbon groups having 6 to 26 carbon atoms.

[0012] Examples of the aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned groups.

[0013] The heteroaromatic ring is preferably at least one selected from the group consisting of monocyclic, linked, or condensed heteroaromatic groups having 3 to 26 carbon atoms.

[0014] Examples of the heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned groups.

[0015] In the compound, the ratio of the number of fluorine atoms to the number of carbon atoms in the whole molecule is 30% or more. The ratio is preferably 32% or more, more preferably 35% or more, still more preferably 38% or more, and even more preferably 40% or more.

[0016] It is preferable that, among the number of carbon atoms forming the aromatic ring and the number of carbon atoms forming the heteroaromatic ring, the ratio of the number of carbon atoms directly bonded to a fluorine atom is 10% or more. More preferably, the ratio is 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, and 40% or more in order.

[0017] Since the compound can maintain a stable thin film even under high-temperature conditions, the glass transition temperature is 50°C or higher. Preferably, the glass transition temperature is 55°C or higher, more preferably 60°C or higher, and even more preferably 65°C or higher.

[0018] Since the compound can lower the heating temperature during vapor deposition and suppress the thermal decomposition of the material in the vapor deposition process for forming its thin film, the molecular weight is 4000 or less. Preferably, the molecular weight is 3800 or less, more preferably 3600 or less, and even more preferably 3400 or less. Also, the compound has a molecular weight of 500 or more.

[0019] [Regarding formula (A1)] In the above formula (A1), L 1 is a linear, branched, or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted with O, S, or a fluorine atom, or represents a vinylene group which may be substituted with a fluorine atom and may form a ring. In formula (A1), each a independently represents an integer of 0 to 4. In formula (A1), each b independently represents an integer of 1 to 4. In formula (A1), each Rf independently represents a monovalent to divalent substituent having 1 or more carbon atoms containing 3 or more fluorine atoms.

[0020] Among the carbon atoms forming the above Rf, the proportion of the carbon atoms directly bonded to fluorine atoms is preferably 30% or more. More preferably, the proportion is 40% or more, still more preferably 50% or more, even more preferably 60% or more, and particularly preferably 70% or more.

[0021] The molecular structure represented by the above Rf is not particularly limited and may be linear, branched, or cyclic. Rf may be an aromatic compound or an aliphatic compound, and may contain O or S, or these may be combined.

[0022] The above Rf preferably contains, as a partial structure regardless of the presence or absence of fluorine atoms, a linear, branched, or cyclic alkyl group, a linear, branched, or cyclic alkoxy group, a linear, branched, or cyclic alkenyl group, or a linear, branched, or cyclic alkenyloxy group. The cyclic alkyl group, cyclic alkoxy group, cyclic alkenyl group, or cyclic alkenyloxy group includes those in which the ring carbon atoms are substituted with an alkyl group or an alkenyl group, and the number of carbon atoms of the alkyl group or alkenyl group bonded to the ring carbon atoms is preferably 1 or more and 6 or less.

[0023] The cyclic alkyl group, cyclic alkoxy group, cyclic alkenyl group, or cyclic alkenyloxy group, as a partial structure of the above Rf regardless of the presence or absence of fluorine atoms, may be, for example, a monovalent group formed when one hydrogen atom is removed from the ring carbon atom, or a monovalent group formed when one hydrogen atom is removed from the alkyl group or alkenyl group bonded to the ring carbon atom (i.e., a cycloalkylalkyl group, a cycloalkylalkenyl group, a cycloalkenylalkyl group, or a cycloalkenylalkenyl group). As the linear, branched, or cyclic alkyl group as the partial structure of the above Rf, regardless of the presence or absence of fluorine atoms, for example, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, alkyl groups having a structural isomeric relationship with these alkyl groups, cyclopropyl group, cyclobutyl group, cyclopentyl group, 1-methylcyclopentyl group, cyclopentylmethyl group, cyclohexyl group, adamantyl group, etc. are preferably included. Among these groups, in terms of excellent metal patterning performance, it is more preferable to include, as the partial structure, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, alkyl groups having a structural isomeric relationship with these alkyl groups, and a cyclohexyl group.

[0024] As the linear, branched, or cyclic alkoxy group as the partial structure of the above Rf, regardless of the presence or absence of fluorine atoms, it is preferable that the linear, branched, or cyclic alkyl group as the partial structure of the above-mentioned Rf, regardless of the presence or absence of fluorine atoms, includes an alkoxy group bonded to an oxygen atom. Among these groups, in terms of excellent metal patterning performance, it is more preferable to include, as the partial structure, an alkoxy group in which a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, or an alkyl group having a structural isomeric relationship with these alkyl groups is bonded to an oxygen atom.

[0025] As the linear, branched, or cyclic alkenyl group as the partial structure of the above Rf, excluding the presence or absence of fluorine atoms, vinyl group, 1-propenyl group, 1-butenyl group, 1-pentenyl group, 1-hexenyl group, alkenyl groups having a structural isomeric relationship with these alkenyl groups, 1-cyclopropenyl group, 1-cyclobutenyl group, 1-cyclopentenyl group, 1-cyclohexenyl group, cycloalkenyl groups having a structural isomeric relationship with these cycloalkenyl groups, etc. are preferably included. Among these groups, in terms of excellent metal patterning performance, it is more preferable to include, as the partial structure, vinyl group, 1-propenyl group, 1-butenyl group, 1-pentenyl group, 1-hexenyl group, alkenyl groups having a structural isomeric relationship with these alkenyl groups, 1-cyclopentenyl group, 1-cyclohexenyl group.

[0026] As the linear, branched, or cyclic alkenyloxy as the partial structure of the above Rf, excluding the presence or absence of fluorine atoms, it preferably includes an alkenyloxy group in which the linear, branched, or cyclic alkenyl group as the partial structure of the above Rf, excluding the presence or absence of fluorine atoms, is bonded to an oxygen atom. Among these groups, in terms of excellent metal patterning performance, it is more preferable to include, as the partial structure, an alkenyloxy group in which vinyl group, 1-propenyl group, 1-butenyl group, 1-pentenyl group, 1-hexenyl group, alkenyl groups having a structural isomeric relationship with these alkenyl groups, 1-cyclopentenyl group, 1-cyclohexyl group are bonded to an oxygen atom.

[0027] Each of the above Rf is more preferably independently included as the partial structure a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an alkyl group having a structural isomeric relationship with these alkyl groups, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 1-methylcyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, or an adamantyl group, each containing three or more fluorine atoms.

[0028] The above Rf preferably has a structure represented by the following formula (001). [Chemical formula] In formula (001), Rf 001 each independently represents a linear, branched, or cyclic monovalent or divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms and containing three or more fluorine atoms, or represents a vinylene group which may form a ring and contains three or more fluorine atoms. L 001 each independently represents a linear, branched, or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted with O, S, or a fluorine atom, or represents a vinylene group which may be substituted with a fluorine atom and may form a ring. a 001 each independently represents an integer from 0 to 4. a 002 each independently represents an integer from 1 to 4.

[0029] Rf 001 each independently preferably has a ratio of the number of carbon atoms directly bonded to fluorine atoms among the carbon atoms forming the structure of 30% or more, more preferably 40% or more, still more preferably 50% or more, even more preferably 60% or more, and particularly preferably 70% or more.

[0030] Rf 001 each independently is more preferably a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, an alkyl group having a structural isomeric relationship with these alkyl groups, cyclopropyl group, cyclobutyl group, cyclopentyl group, 1-methylcyclopentyl group, cyclopentylmethyl group, cyclohexyl group, or adamantyl group, each containing three or more fluorine atoms.

[0031] L 001Since it can suppress the formation of a metal film on the membrane surface, each is independently more preferably a methylene group, ethylene group, n-propylene group, n-butylene group, n-pentylene group, n-hexylene group, n-heptylene group, n-octylene group, an alkylene group having a structural isomeric relationship with these alkylene groups, a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a 1-methylpentylene group, a cyclopentylmethyl group, a cyclohexylene group, an adamantandiyl group, or a vinylene group which may form a ring, and which may be substituted with an O, S, or fluorine atom.

[0032] a 001 Each is independently preferably an integer of 0 to 3, and more preferably an integer of 0 to 2. a 002 Each is independently preferably an integer of 1 to 3, and more preferably an integer of 1 to 2.

[0033] The number of carbon atoms in the structure represented by formula (001) is preferably 1 or more and 36 or less, more preferably 1 or more and 30 or less, still more preferably 1 or more and 24 or less, even more preferably 1 or more and 20 or less, particularly preferably 1 or more and 16 or less. Particularly more preferably 2 or more and 16 or less.

[0034] (Specific examples of formula (A1)) Regarding formula (A1), for example, it can have the structures shown in the following (AAA1) to (AAA126). Note that the mark "*" used in the following structures represents the bonding site.

[0035]

Chemical formula

[0036]

Chemical formula

[0037]

Chemical formula

[0038]

Chem.

[0039]

Chem.

[0040]

Chem.

[0041]

Chem.

[0042] As the charging material according to one aspect of the present disclosure, it is preferable that the compound contained in the aforementioned charging material A is a compound represented by the following formula (1).

Chem.

[0043] [Regarding R] In the above formula (1), each R independently is A monocyclic, linked ring, or condensed ring monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, A monocyclic, linked ring, or condensed ring monovalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, A linear, branched, or cyclic monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted, A cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, or represents the structure represented by the above formula (A1).

[0044] As R, each independently, A monovalent aromatic hydrocarbon group of a monocyclic, linked ring, or condensed ring having 6 to 26 carbon atoms, which may be substituted, A monovalent heteroaromatic group of a monocyclic, linked ring, or condensed ring having 3 to 26 carbon atoms, which may be substituted, A cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, A cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, or The structure represented by the above formula (A1) is preferable.

[0045] As R, each independently, A monovalent aromatic hydrocarbon group of a monocyclic, linked ring, or condensed ring having 6 to 26 carbon atoms, which may be substituted, A monovalent heteroaromatic group of a monocyclic, linked ring, or condensed ring having 3 to 26 carbon atoms, which may be substituted, A cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, A cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, is more preferable.

[0046] As the above-mentioned monovalent aromatic hydrocarbon group of a monocyclic, linked ring, or condensed ring, phenyl or a structure in which a plurality of benzene rings are linked or condensed is preferable. As the above-mentioned monovalent heteroaromatic group of a monocyclic, linked ring, or condensed ring, the heteroatom is N, O, or S, and a 5-membered ring, 6-membered ring, or a structure in which they are condensed is preferable As the above-mentioned cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, the heteroatom is N, O, or S, and a 5-membered ring, 6-membered ring, 7-membered ring, or a structure in which they are condensed is preferable.

[0047] Examples of the compound that provides the monocyclic, linked-ring, or condensed-ring monovalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned group, and the like.

[0048] Examples of the compound that provides the monocyclic, linked-ring, or condensed-ring monovalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which benzene or naphthalene is condensed with the above-mentioned group, and the like are preferable.

[0049] Examples of the compound that provides the monocyclic, linked-ring, or condensed-ring monovalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, benzochrysene, triphenylene, and the like are more preferable.

[0050] Examples of the compound that provides the monocyclic, linked-ring, or condensed-ring monovalent heteroaromatic group described above include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the group described above, and the like.

[0051] Examples of the compound that provides the monocyclic, linked-ring, or condensed-ring monovalent heteroaromatic group described above include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which benzene or naphthalene is condensed with the group described above, and the like are preferable.

[0052] Examples of the compound that provides the above-described monocyclic, linked ring, or condensed ring monovalent heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and the like are more preferable.

[0053] Examples of the compound that provides the above-described cyclic monovalent heteroaliphatic hydrocarbon group include morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, and the like.

[0054] Examples of the compound that provides the above-described cyclic monovalent heteroaliphatic hydrocarbon group include piperazine, homopiperazine, hexahydro-1,3,5-triazine, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane, and the like are preferable.

[0055] Examples of the compound that provides the above-described cyclic monovalent aliphatic hydrocarbon group include adamantane, diamantane, cyclohexane, and the like.

[0056] In the above formula (1), when R is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), or preferably substituted with at least one group selected from the group consisting of groups in which the above-described groups are combined.

[0057] Examples of the substituent of R include a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined.

[0058] More preferably, the substituent of R is, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), or at least one group selected from the group consisting of groups in which the above-described groups are combined.

[0059] More preferably, each of the substituents of R is independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, a thiazolyl group, a structure represented by the above formula (A1), or at least one group selected from the group consisting of groups in which the above-described groups are combined.

[0060] As the substituent of R, each independently, a trifluoromethyl group, a trifluoromethoxy group, a structure represented by the formula (A1), and a fluorine atom are most preferred.

[0061] In the above formula (1), n each independently represents an integer of 1 to 6, an integer of 1 to 5 is preferred, an integer of 1 to 4 is more preferred, an integer of 1 to 3 is even more preferred, an integer of 1 to 2 is even more preferred, and 1 is most preferred.

[0062] [Specific Examples of R] As R, for example, it can take the structures shown in the above (AAA1) to (AAA126) and the structures shown in the following (AAC1) to (AAC450). Note that the mark "*" used in the following structures represents the bonding site. F represents a fluorine atom, Rf represents the structure represented by the above formula (A1), v represents an integer of 0 to 5, w represents an integer of 0 to 4, x represents an integer of 0 to 3, y represents an integer of 0 to 2, and z represents an integer of 0 to 1.

[0063] [Chemical Structure]

[0064] [Chemical Structure]

[0065] [Chemical Structure]

[0066] [Chemical Structure]

[0067] [Chemical Structure]

[0068] [Chemistry]

[0069] [Chemistry]

[0070] [Chemistry]

[0071] [Chemistry]

[0072] [Chemistry]

[0073] [Chemistry]

[0074] [Chemistry]

[0075] [Chemistry]

[0076] [Chemistry]

[0077] [Chemistry]

[0078] [Chemistry]

[0079] [Chemistry]

[0080] [Chemistry]

[0081] [Chemistry]

[0082] [Chemistry]

[0083] [Chemistry]

[0084] [Chemistry]

[0085] [Chemistry]

[0086] [Chemistry]

[0087] [Chemistry]

[0088] [Regarding X] In formula (1), X is, independently of each other, a monocyclic, linked-ring, or condensed-ring 2- to 6-valent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, A monocyclic, linked-ring, or fused-ring divalent to hexavalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, A linear, branched, or cyclic divalent to hexavalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted, A cyclic divalent to hexavalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, Represents O, S, Si, N, or N(R). R is the same as the definition described above.

[0089] As the above-described X, each independently, A monocyclic, linked-ring, or fused-ring divalent to hexavalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, A monocyclic, linked-ring, or fused-ring divalent to hexavalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, A linear, branched, or cyclic divalent to hexavalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted, A cyclic divalent to hexavalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, O, S, or N is preferred.

[0090] As the above-described X, each independently, A monocyclic, linked-ring, or fused-ring divalent to hexavalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, A monocyclic, linked-ring, or fused-ring divalent to hexavalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, A linear, branched, or cyclic divalent to hexavalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted, A cyclic divalent to hexavalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, Or N is more preferred.

[0091] As the above-described monocyclic, linked-ring, or fused-ring divalent to hexavalent aromatic hydrocarbon group, phenyl, or a structure in which a plurality of benzene rings are linked or fused is preferred.

[0092] As the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to hexavalent heteroaromatic group, heteroatoms are N, O, or S, and a 5-membered ring, 6-membered ring, or a structure in which they are condensed is preferable.

[0093] As the above-mentioned cyclic divalent to hexavalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, heteroatoms are N, O, or S, and a 5-membered ring, 6-membered ring, 7-membered ring, or a structure in which they are condensed is preferable.

[0094] Examples of the compound that provides the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to hexavalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned group.

[0095] Examples of the compound that provides the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to hexavalent heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned group.

[0096] Examples of the compound that provides the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to hexavalent heteroaromatic group include, for example, pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which benzene or naphthalene is condensed with the above-mentioned group, etc. are preferable.

[0097] Examples of the compound that provides the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to hexavalent heteroaromatic group include, for example, pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, etc. are more preferable.

[0098] Examples of the compound that provides the above-mentioned cyclic divalent to hexavalent heteroaliphatic hydrocarbon group include, independently of each other, morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0099] Examples of the compound that provides the above-mentioned cyclic divalent to hexavalent heteroaliphatic hydrocarbon group include morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxane, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, and the like.

[0100] Examples of the compound that provides the above-mentioned cyclic divalent to hexavalent heteroaliphatic hydrocarbon group include piperazine, homopiperazine, hexahydro-1,3,5-triazine, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, and the like are more preferable. Examples of the compound that provides the above-mentioned monocyclic, linked ring, or condensed ring divalent to tetravalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which benzene or naphthalene is condensed to the above-mentioned group.

[0101] Examples of the compound that provides the above-mentioned monocyclic, linked ring, or condensed ring divalent to tetravalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, benzochrysene, triphenylene, and the like are preferable.

[0102] Examples of the compound that provides the above-mentioned cyclic divalent to hexavalent aliphatic hydrocarbon group include methane, adamantane, diamantane, cyclohexane, and the like.

[0103] In the above formula (1), when X is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), or it is preferably substituted with at least one group selected from the group consisting of the above-described groups combined.

[0104] Examples of the substituent of X include a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of the above-described groups combined.

[0105] More preferably, the substituent of X is, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), or at least one group selected from the group consisting of the above-described groups combined.

[0106] Examples of the substituent for X include, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, a thiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined. It is even more preferable.

[0107] As the substituent for X, each independently, a trifluoromethyl group, a trifluoromethoxy group, a structure represented by the formula (A1), and a fluorine atom are most preferable.

[0108] In the formula (1), each l independently represents an integer of 1 to 3, preferably an integer of 1 to 2, and more preferably 1. In the formula (1), each X independently is a group having a valence of 1 to 6, preferably having a valence of 1 to 5, and more preferably having a valence of 1 to 4.

[0109] [Specific Examples of X] As X, for example, it can have the structures shown in the following (AAB1) to (AAB563), (AAB801) to (AAB803). Note that the mark "*" used in the following structures represents a bonding site. F represents a fluorine atom, Rf represents a structure represented by the above formula (A1), v represents an integer of 0 to 5, w represents an integer of 0 to 4, x represents an integer of 0 to 3, y represents an integer of 0 to 2, and z represents an integer of 0 to 1.

[0110] [Chemical Formula]

[0111] [Chemical Formula]

[0112] [Chemical Formula]

[0113] [Chemical]

[0114] [Chemical]

[0115] [Chemical]

[0116] [Chemical]

[0117] [Chemical]

[0118] [Chemical]

[0119] [Chemical]

[0120] [Chemical]

[0121] [Chemical]

[0122] [Chemical]

[0123] [Chemical]

[0124]

Chem.

[0125]

Chem.

[0126]

Chem.

[0127]

Chem.

[0128]

Chem.

[0129]

Chem.

[0130]

Chem.

[0131]

Chem.

[0132]

Chem.

[0133] [Regarding L] In the above formula (1), L is, independently of each other, a monocyclic, linked-ring, or condensed-ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, A monocyclic, fused-ring, or bridged-ring divalent to tetravalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, A linear, branched, or cyclic divalent to tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted, A cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, Represents O, S, Si, N, or N(R). R is the same as defined above.

[0134] As the above-described L, each independently, A monocyclic, fused-ring, or bridged-ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, A monocyclic, fused-ring, or bridged-ring divalent to tetravalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, A linear, branched, or cyclic divalent to tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted, A cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, O, S, Si, or N is preferable.

[0135] As the above-described L, each independently, A monocyclic, fused-ring, or bridged-ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, A monocyclic, fused-ring, or bridged-ring divalent to tetravalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, A cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, A cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, O, S, or N is more preferable.

[0136] As the above-described L, each independently, A monocyclic, fused-ring, or bridged-ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, A monocyclic, fused-ring, or bridged-ring divalent to tetravalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, A cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted, A cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted, Or N is more preferable.

[0137] As the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to tetravalent aromatic hydrocarbon group, phenyl or a structure in which a plurality of benzene rings are linked or condensed is preferable.

[0138] As the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to tetravalent heteroaromatic group, the hetero atom is N, O, or S, and a 5-membered ring, 6-membered ring, or a structure in which they are condensed is preferable.

[0139] As the above-mentioned cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, the hetero atom is N, O, or S, and a 5-membered ring, 6-membered ring, 7-membered ring, or a structure in which they are condensed is preferable.

[0140] Examples of the compound that provides the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to tetravalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned group.

[0141] Examples of the compound that provides the monocyclic, linked-ring, or condensed-ring divalent to tetravalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which benzene or naphthalene is condensed to the above-described group, etc. are preferable.

[0142] Examples of the compound that provides the monocyclic, linked-ring, or condensed-ring divalent to tetravalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, benzochrysene, triphenylene, etc. are more preferable.

[0143] Examples of the compound that provides the monocyclic, linked-ring, or condensed-ring divalent to tetravalent heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed to the above-described group, etc.

[0144] Examples of the compound that provides the above-mentioned monocyclic, linked ring, or condensed ring divalent to tetravalent heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which benzene or naphthalene is condensed to the above-mentioned group, etc. are preferable.

[0145] Examples of the compound that provides the above-mentioned monocyclic, linked ring, or condensed ring divalent to tetravalent heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, etc. are more preferable.

[0146] Examples of the compound that provides the above-mentioned cyclic divalent to tetravalent heteroaliphatic hydrocarbon group include morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0147] Examples of the compound that provides the above-mentioned cyclic divalent to tetravalent heteroaliphatic hydrocarbon group include morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxane, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0148] Examples of the compound that provides the above-mentioned cyclic divalent to tetravalent heteroaliphatic hydrocarbon group include piperazine, homopiperazine, hexahydro-1,3,5-triazine, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc. are more preferable.

[0149] Examples of the compound that provides the above-mentioned cyclic divalent to tetravalent aliphatic hydrocarbon group include adamantane, diamantane, cyclohexane, etc.

[0150] In the above formula (1), when L is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), or It is preferably substituted with at least one group selected from the group consisting of the above-mentioned groups combined.

[0151] Examples of the substituent of L include, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined, etc.

[0152] Examples of the substituent of L include, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined. It is preferably such a group.

[0153] Examples of the substituent of L include, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, a thiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined. It is more preferably such a group.

[0154] As the substituent of L, independently of each other, a trifluoromethyl group, a trifluoromethoxy group, a structure represented by the formula (A1), and a fluorine atom are most preferred.

[0155] In the above formula (1), m each independently represents an integer of 0 to 12, preferably an integer of 0 to 10, more preferably an integer of 0 to 8, and even more preferably an integer of 0 to 6.

[0156] [Specific examples of L] As L, for example, it can have the structures shown in the above (AAB1) to (AAB563), (AAB801) to (AAB803).

[0157] As the charging material according to one aspect of the present disclosure, it is preferable that the compound contained in the aforementioned charging material A is a compound represented by the following formula (2) or (3).

[0158] [Chemical formula] [Chemical formula] In formula (2), Y is each independently An optionally substituted monocyclic, linked ring, or condensed ring divalent to hexavalent aromatic hydrocarbon group having 6 to 26 carbon atoms, An optionally substituted monocyclic, linked ring, or condensed ring divalent to hexavalent heteroaromatic group having 3 to 26 carbon atoms, An optionally substituted linear, branched, or cyclic divalent to hexavalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, An optionally substituted cyclic divalent to hexavalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, Represents O, S, or Si. In formula (2) and formula (3), L 1 Is each independently An optionally substituted monocyclic, linked ring, or condensed ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, An optionally substituted monocyclic, linked ring, or condensed ring divalent to tetravalent heteroaromatic group having 3 to 26 carbon atoms, An optionally substituted linear, branched, or cyclic divalent to tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, An optionally substituted cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, Represents N or N(R). R is the same as defined above. In formula (2) and formula (3), R 1are each independently a monocyclic, fused-ring, or bridged monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, a monocyclic, fused-ring, or bridged monovalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, a linear, branched, or cyclic monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted, a cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, or represents the structure represented by the above formula (A1). In formula (2) and formula (3), q each independently represents an integer of 0 to 12. In formula (2) and formula (3), r each independently represents an integer of 0 to 4. In formula (2) and formula (3), t each independently represents an integer of 0 to 4. In formula (2) and formula (3), at least one R 1 has at least one selected from the group consisting of an aromatic ring and a heteroaromatic ring in the molecule, and the ring is substituted with at least one selected from the group consisting of a fluorine atom and the structure represented by the above formula (A1).

[0159] [Regarding Y] Y are each independently a divalent to hexavalent aromatic hydrocarbon group of a monocyclic, fused-ring, or bridged having 6 to 26 carbon atoms, which may be substituted, a divalent to hexavalent heteroaromatic group of a monocyclic, fused-ring, or bridged having 3 to 26 carbon atoms, which may be substituted, a divalent to hexavalent aliphatic hydrocarbon group of a linear, branched, or cyclic having 1 to 18 carbon atoms, which may be substituted, a divalent to hexavalent cyclic heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, represents O, S, or Si.

[0160] As Y, each independently a divalent to hexavalent aromatic hydrocarbon group of a monocyclic, fused-ring, or bridged having 6 to 26 carbon atoms, which may be substituted, A monocyclic, linked-ring, or fused-ring divalent to hexavalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, A linear, branched, or cyclic divalent to hexavalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted, or A cyclic divalent to hexavalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, is preferable.

[0161] As the above-mentioned monocyclic, linked-ring, or fused-ring divalent to hexavalent aromatic hydrocarbon group, phenyl or a structure in which a plurality of benzene rings are linked or fused is preferable.

[0162] As the above-mentioned monocyclic, linked-ring, or fused-ring divalent to hexavalent heteroaromatic group, the heteroatom is N, O, or S, and a 5-membered ring, 6-membered ring, or a structure in which they are condensed is preferable. As the above-mentioned cyclic divalent to hexavalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, the heteroatom is N, O, or S, and a 5-membered ring, 6-membered ring, 7-membered ring, or a structure in which they are fused is preferable.

[0163] Examples of the compound that provides the above-mentioned monocyclic, linked-ring, or fused-ring divalent to hexavalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is fused to the above-mentioned group.

[0164] Examples of the compound that provides the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to hexavalent heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned group, and the like.

[0165] Examples of the compound that provides the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to hexavalent heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which benzene or naphthalene is condensed with the above-mentioned group, and the like are preferable.

[0166] Examples of the compound that provides the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to hexavalent heteroaromatic group include, for example, pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, etc., which are more preferable.

[0167] Examples of the compound that provides the above-mentioned cyclic divalent to hexavalent heteroaliphatic hydrocarbon group include, for example, morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0168] Examples of the compound that provides the above-mentioned cyclic divalent to hexavalent heteroaliphatic hydrocarbon group include, for example, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc., which are more preferable.

[0169] Examples of the compound that provides the above-mentioned monocyclic, linked-ring, or condensed-ring divalent to tetravalent aromatic hydrocarbon group include, for example, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, those in which benzene or naphthalene is condensed to the above-mentioned group, etc.

[0170] Examples of the compound that provides the above-mentioned monocyclic, linked ring, or condensed ring divalent to tetravalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, benzochrysene, triphenylene, etc.

[0171] Examples of the substituent of Y described above include a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined.

[0172] Examples of the substituent of Y described above include a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined, which is preferable.

[0173] Examples of the substituent of Y described above include a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, a thiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined, which is more preferable.

[0174] As the substituents of Y described above, each independently, a trifluoromethyl group, a trifluoromethoxy group, a structure represented by the above formula (A1), and a fluorine atom are most preferable.

[0175] [Specific examples of Y] For Y, for example, it can take the structures shown in the above (AAB1) to (AAB563), (AAB801) to (AAB803).

[0176] [L 1 Regarding] In formula (2) and formula (3), L 1 is each independently an optionally substituted monocyclic, linked-ring, or condensed-ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, linked-ring, or condensed-ring divalent to tetravalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted linear, branched, or cyclic divalent to tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, an optionally substituted cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, represents N or N(R). R is the same as defined above.

[0177] As the above-described L 1 each independently is an optionally substituted monocyclic, linked-ring, or condensed-ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, is an optionally substituted monocyclic, linked-ring, or condensed-ring divalent to tetravalent heteroaromatic group having 3 to 26 carbon atoms, is an optionally substituted cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, group of hydrocarbons is an optionally substituted cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, N or N(R) is preferable. R is the same as defined above.

[0178] The above-described L1 Each independently, A monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, A monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, A cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, A cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, Or N(R) is more preferable. R is the same as the definition described above.

[0179] As the above-mentioned monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group, phenyl or a structure in which a plurality of benzene rings are linked or fused is preferable.

[0180] As the above-mentioned monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group, the hetero atom is N, O, or S, and a 5-membered ring, 6-membered ring, or a structure in which they are condensed is preferable.

[0181] As the above-mentioned cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, the hetero atom is N, O, or S, and a 5-membered ring, 6-membered ring, 7-membered ring, or a structure in which they are condensed is preferable.

[0182] Examples of the compound that gives the above-mentioned monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed to the above-mentioned group.

[0183] Examples of the compound that provides the above-mentioned monocyclic, linked ring, or condensed ring divalent to tetravalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which benzene or naphthalene is condensed to the above-mentioned group, etc. are preferable.

[0184] Examples of the compound that provides the above-mentioned monocyclic, linked ring, or condensed ring divalent to tetravalent aromatic hydrocarbon group include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, benzochrysene, triphenylene, etc. are more preferable.

[0185] Examples of the compound that provides the above-mentioned monocyclic, linked ring, or condensed ring divalent to tetravalent heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed to the above-mentioned group, etc.

[0186] Examples of the compound that provides the above-mentioned monocyclic, linked ring, or condensed ring divalent to tetravalent heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which benzene or naphthalene is condensed to the above-mentioned group, etc. are preferable.

[0187] Examples of the compound that provides the above-mentioned monocyclic, linked ring, or condensed ring divalent to tetravalent heteroaromatic group include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, etc. are more preferable.

[0188] Examples of the compound that provides the above-mentioned cyclic divalent to tetravalent heteroaliphatic hydrocarbon group include morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0189] Examples of the compound that provides the above-described cyclic divalent to tetravalent heteroaliphatic hydrocarbon group include piperazine, homopiperazine, hexahydro-1,3,5-triazine, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc., which are preferable.

[0190] Examples of the compound that provides the above-described cyclic divalent to tetravalent aliphatic hydrocarbon group include adamantane, diamantane, cyclohexane, etc.

[0191] In the above formulas (2) and (3), when L 1 is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), or it is preferably substituted with at least one group selected from the group consisting of a group in which the above-described groups are combined.

[0192] Examples of the substituent of the above-described L 1 include, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), at least one group selected from the group consisting of a group in which the above-described groups are combined, etc.

[0193] The above-mentioned L 1 As the substituent of, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), at least one group selected from the group consisting of a group in which the above-mentioned groups are combined is preferable.

[0194] The above-mentioned L 1 As the substituent of, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, a thiazolyl group, a structure represented by the above formula (A1), at least one group selected from the group consisting of a group in which the above-mentioned groups are combined is even more preferable.

[0195] The above-mentioned L 1 As the substituent of, each independently, a trifluoromethyl group, a trifluoromethoxy group, a structure represented by the above formula (A1), and a fluorine atom are most preferable.

[0196] In the above formula (2) and formula (3), q each independently represents an integer of 0 to 12, preferably an integer of 0 to 10, more preferably an integer of 0 to 8, and even more preferably an integer of 0 to 6.

[0197] [L 1 [Specific examples thereof] As X in the above-mentioned L 1 For example, it can have the structures shown in the above (AAB1) to (AAB563), (AAB801) to (AAB803).

[0198] [R 1 [Regarding] In formula (2) and formula (3), R 1are each independently a monocyclic, linked-ring, or condensed-ring monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, a monocyclic, linked-ring, or condensed-ring monovalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, a linear, branched, or cyclic monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted, a cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, or represents the structure represented by the above formula (A1)

[0199] the above-mentioned R 1 as each independently a monocyclic, linked-ring, or condensed-ring monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, a monocyclic, linked-ring, or condensed-ring monovalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, a cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, a cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, or the structure represented by the above formula (A1) is preferred.

[0200] the above-mentioned R 1 as each independently a monocyclic, linked-ring, or condensed-ring monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms, which may be substituted, a monocyclic, linked-ring, or condensed-ring monovalent heteroaromatic group having 3 to 26 carbon atoms, which may be substituted, a cyclic monovalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, or a cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, which may be substituted, is more preferred.

[0201] As the above-mentioned monocyclic, linked-ring, or condensed-ring monovalent aromatic hydrocarbon group, phenyl or a structure in which a plurality of benzene rings are linked or condensed is preferred.

[0202] As the monovalent heteroaromatic group of the above-mentioned monocyclic, linked ring, or condensed ring, the heteroatom is N, O, or S, and a 5-membered ring, 6-membered ring, or a structure in which they are condensed is preferable.

[0203] As the cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms described above, the heteroatom is N, O, or S, and a 5-membered ring, 6-membered ring, 7-membered ring, or a structure in which they are condensed is preferable.

[0204] Examples of the compound that gives the above-mentioned monovalent aromatic hydrocarbon group of a monocyclic, linked ring, or condensed ring include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned group.

[0205] Examples of the compound that gives the above-mentioned monovalent aromatic hydrocarbon group of a monocyclic, linked ring, or condensed ring include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which benzene or naphthalene is condensed with the above-mentioned group are preferable.

[0206] Examples of the compound that gives the above-mentioned monovalent aromatic hydrocarbon group of a monocyclic, linked ring, or condensed ring include benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, benzochrysene, triphenylene, etc. are more preferable.

[0207] Examples of the compound that provides the monocyclic, linked-ring, or condensed-ring monovalent heteroaromatic group described above include, for example, pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-described group, and the like.

[0208] Examples of the compound that provides the monocyclic, linked-ring, or condensed-ring monovalent heteroaromatic group described above include, for example, pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which benzene or naphthalene is condensed with the above-described group, and the like are preferable.

[0209] Examples of the compound that provides the monovalent heteroaromatic group of the above-mentioned monocyclic, linked ring, or condensed ring include, for example, pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxine, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, dibenzo-1,4-dioxine, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, etc. are more preferable.

[0210] Examples of the compound that provides the cyclic monovalent heteroaliphatic hydrocarbon group include, for example, morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0211] Examples of the compound that provides the cyclic monovalent heteroaliphatic hydrocarbon group include, for example, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc. are preferable.

[0212] Examples of the compound that provides the cyclic monovalent aliphatic hydrocarbon group include, for example, adamantane, diamantane, cyclohexane, etc.

[0213] In the above formulas (2) and (3), when R 1 is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, A linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), or at least one group selected from the group consisting of groups in which the above-described groups are combined.

[0214] Examples of the substituent of the above-described R 1 include, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined.

[0215] Examples of the substituent of the above-described R 1 include, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined.

[0216] Examples of the substituent of the above-described R 1Examples of the substituent include, for example, a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazolyl group, a thiazolyl group, a structure represented by the above formula (A1), and at least one group selected from the group consisting of groups in which the above-described groups are combined, which is more preferable.

[0217] The above-described R 1 As the substituent, each independently, a trifluoromethyl group, a trifluoromethoxy group, a structure represented by the above formula (A1), and a fluorine atom are most preferable.

[0218] In the above formulas (2) and (3), r each independently represents an integer of 1 to 6, preferably an integer of 1 to 5, more preferably an integer of 1 to 4, still more preferably an integer of 1 to 3, still more preferably an integer of 1 to 2, and most preferably 1.

[0219] [Specific examples of R 1 The above-described R 1 For example, it can take the structures shown in the above (AAA1) to (AAA126) and the structures shown in the above (AAC1) to (AAC450).

[0220] [Specific examples of the charging material] Regarding the charging material according to one aspect of the present disclosure, the compounds of (A1) to (A979) are exemplified below, but the present disclosure is not limited to these compounds.

[0221]

Chemical formula

[0222]

Chemical formula

[0223]

Chemical formula

[0224]

Chem.

[0225]

Chem.

[0226]

Chem.

[0227]

Chem.

[0228]

Chem.

[0229]

Chem.

[0230]

Chem.

[0231]

Chem.

[0232]

Chem.

[0233]

Chem.

[0234] [Chemistry]

[0235] [Chemistry]

[0236] [Chemistry]

[0237] [Chemistry]

[0238] [Chemistry]

[0239] [Chemistry]

[0240] [Chemistry]

[0241] [Chemistry]

[0242] [Chemistry]

[0243] [Chemistry]

[0244] [Chemistry]

[0245]

Chem.

[0246]

Chem.

[0247]

Chem.

[0248]

Chem.

[0249]

Chem.

[0250]

Chem.

[0251]

Chem.

[0252]

Chem.

[0253]

Chem.

[0254]

Chem.

[0255]

Chem.

[0256]

Chem.

[0257]

Chem.

[0258]

Chem.

[0259]

Chem.

[0260]

Chem.

[0261]

Chem.

[0262]

Chem.

[0263]

Chem.

[0264]

Chem.

[0265]

Chem.

[0266] [Chemistry]

[0267] [Chemistry]

[0268] [Chemistry]

[0269] [Chemistry]

[0270] [Chemistry]

[0271] [Chemistry]

[0272] [Chemistry]

[0273] [Chemistry]

[0274] [Chemistry]

[0275] [Chemistry]

[0276] [Chemistry]

[0277]

Chem.

[0278]

Chem.

[0279]

Chem.

[0280]

Chem.

[0281]

Chem.

[0282]

Chem.

[0283]

Chem.

[0284]

Chem.

[0285]

Chem.

[0286]

Chem.

[0287] [Chemistry]

[0288] [Charged film]

[0289] The charging material can form a charged film with excellent light stability.

[0290] The method for forming a charged film (film-forming method) according to one aspect of the present disclosure is not particularly limited, and known methods such as vacuum evaporation method, spin coating method, casting method, dip coating method, die coating method, bar coating method, offset method, spray coating method, inkjet method, screen method, offset method, flexo method, gravure method, microcontact method, etc. can be applied. From the viewpoint of forming a uniform amorphous film, the vacuum evaporation method is preferred as the film-forming method. Also, the film may be annealed in a temperature environment higher than room temperature after film formation. There is no particular limitation on the film thickness of the charging material.

[0291] In addition, other organic molecular materials, polymers, etc. may be arbitrarily added to the charging material within the range where the stable potential of the film can be maintained.

[0292] The substrate for forming the charged film may be metal or non-metal. For example, organic films, metal films, oxide films, inorganic films, etc. can be mentioned, and there is no particular limitation. Also, the material of the substrate is not particularly limited, and glass, plastic, metal, ceramic, and any other material can be used.

[0293] The charged film using the charging material according to one aspect of the present disclosure exhibits a positive or negative surface potential on its surface. The film of the present invention preferably exhibits a film thickness dependence (giant surface potential) in which the surface potential changes depending on the film thickness.

[0294] Here, regarding the degree of the giant surface potential, the slope of the approximate line in the plot diagram with the surface potential of the film on the vertical axis and the film thickness on the horizontal axis can be used as an index. In the following description, this slope is referred to as the "slope of the giant surface potential", and the sign (+ or -) of the slope is referred to as the "polarity of the giant surface potential".

[0295] The polarity of the large surface potential may be positive or negative. When the film exhibits a positive large surface potential, the slope of the large surface potential is preferably 10 mV / nm or more, more preferably 20 mV / nm or more, still more preferably 30 mV / nm or more, and even more preferably 40 mV / nm or less. When the film exhibits a negative large surface potential, the slope of the large surface potential is preferably -10 mV / nm or less, more preferably -20 mV / nm or less, still more preferably -30 mV / nm or less, and even more preferably -40 mV / nm or less.

[0296] The charged film using the charge material according to one aspect of the present disclosure can be stably maintained with almost no attenuation of the absolute value of its large surface potential against light irradiation.

[0297] Here, the stability of the large surface potential against light irradiation is referred to as the "maintenance rate of the surface potential", and is defined as the value obtained by dividing the absolute value of the large surface potential after light irradiation by the absolute value of the large surface potential before light irradiation.

[0298] [Maintenance rate of surface potential]

[0299] The maintenance rate of the surface potential is not particularly limited, but a maintenance rate of 0.7 or more is preferable. As the maintenance rate, 0.75 or more is more preferable, 0.8 or more is still more preferable, 0.85 or more is even more preferable, and 0.9 or more is most preferable.

[0300] The maintenance rate of the surface potential is not particularly limited, but when the wavelength of the irradiated light is longer than 350 nm, the irradiance of the irradiated light is 0.3 mW / cm at 365 nm 2 or more, and the light irradiation time is 50 seconds, a maintenance rate of 0.7 or more is preferable.

[0301] Although there is no particular limitation on the wavelength of light as long as it can stably maintain a large surface potential, it is preferably stable with respect to a wavelength range longer than 350 nm. As the stable wavelength range of the film, a wavelength longer than 320 nm is more preferable, a wavelength longer than 300 nm is further preferable, a wavelength longer than 280 nm is even more preferable, and a wavelength longer than 250 nm is most preferable.

[0302] Although there is no particular limitation on the irradiance of light as long as it can stably maintain a large surface potential, the irradiance of the irradiated light is preferably 0.3 mW / cm 2 or more at 365 nm. The irradiance of the irradiated light is more preferably 0.5 mW / cm 2 or more at 365 nm, even more preferably 0.6 mW / cm 2 or more at 365 nm, even more preferably 0.8 mW / cm 2 or more at 254 nm, even more preferably 0.9 mW / cm 2 or more at 254 nm.

[0303] Although there is no particular limitation on the irradiation time of light as long as it can stably maintain a large surface potential, light irradiation for 50 seconds or more is preferable. 80 seconds or more is preferable, 100 seconds or more is more preferable, and 120 seconds or more is even more preferable.

[0304] [Maintenance rate of surface potential during long-term storage under light irradiation]

[0305] The charged film using the charge material according to one aspect of the present disclosure can stably maintain the absolute value of its large surface potential with almost no attenuation during long-term storage under light irradiation.

[0306] Although not particularly limited, the maintenance rate of the surface potential during long-term storage under light irradiation is preferably 0.7 or more. As the maintenance rate, 0.75 or more is more preferable, 0.8 or more is even more preferable, 0.85 or more is even more preferable, and 0.9 or more is most preferable.

[0307] Although not particularly limited, the retention rate of the surface potential under long-term light irradiation is preferably 0.7 or more when stored for 100 hours in a room maintained at an average illuminance of 200 lux or more using an LED light.

[0308] Although not particularly limited, the wavelength range of light in a room using an LED light is preferably in the wavelength range of 400 nm to 800 nm, more preferably in the wavelength range of 380 nm to 900 nm, still more preferably in the wavelength range of 350 nm or more, even more preferably in the wavelength range of 320 nm or more, and particularly preferably in the wavelength range of 280 nm or more.

[0309] In long-term storage under light irradiation, the average illuminance for stably maintaining a large surface potential is preferably 200 lux or more, more preferably 300 lux or more, still more preferably 400 lux or more, even more preferably 500 lux or more, and most preferably 600 lux or more.

[0310] In long-term storage under light irradiation, the time for stably maintaining a large surface potential is preferably 100 hours or more, more preferably 200 hours or more, still more preferably 300 hours or more, even more preferably 500 hours or more, and most preferably 1000 hours or more.

[0311] The storage conditions are not particularly limited, such as under a nitrogen atmosphere, under vacuum, or under the atmosphere.

[0312] From the viewpoint of light stability, the thin film of the charged material preferably has a high electrical resistivity. The electrical resistivity is preferably 5×10 10 Ωm or more, and the electrical resistivity is 6×10 10 Ωm or more, 8×10 10 Ωm or more, 1×10 11 Ωm or more, 2×10 11 Ωm or more, 4×10 11 Ωm or more, 6×10 11 Ωm or more, 8×10 11 Ωm or more, 1×10 12 Ωm or more, 2×10 12 Ωm or more, 4×1012 Above Ωm, 6×10 12 Above Ωm, 8×10 12 Above Ωm, 1×10 13 It is preferably above Ωm.

[0313] [Material for electret] Since the surface potential is developed on the film surface of the charging material according to one aspect of the present disclosure, it can be used as a material for an electret. In addition, since the surface potential developed by the charging film according to one aspect of the present disclosure can be stably maintained, by using the charging material according to one aspect of the present disclosure as an electret material, it is possible to contribute to the stability of various elements using an electret.

[0314] [Electret film] The charging film according to one aspect of the present disclosure using a material for an electret may have a positive surface potential or a negative surface potential. An electret has, for example, a substrate and an electret film provided on this substrate, and the electret film is composed of a charging film according to one aspect of the present disclosure. In addition, the electret may have members other than the substrate and the electret film. For example, an electrode made of a conductive material may be provided between the substrate and the electret film. The surface potential of the electret film varies depending on the use of the electret, but when it is a positive surface potential, it is preferably 100 V or more, may be 300 V or more, or may be 500 V or more. When it is a negative surface potential, it is preferably -100 V or less, may be -300 V or less, or may be -500 V or less.

[0315] [Vibration power generation element] The charging material, charging film, electret material, and electret film according to one aspect of the present disclosure can be used for a vibration power generation element. It may be a film with a positive surface potential, a film with a negative surface potential, or both a film with a positive surface potential and a film with a negative surface potential.

[0316] Examples of the vibration power generation element include, for example, a vibration power generator, a vibration sensor, a fluid device, and the like. The vibration power generator is configured to, for example, vibrate at least one of the charged film and the counter electrode according to an aspect of the present disclosure to induce charges in the counter electrode and extract the charges as an electric current. The vibration sensor is configured to, for example, when the vibration detection target vibrates, at least one of the film and the counter electrode vibrates in conjunction with the vibration, and the vibration of the vibration detection target is detected using, as a detection signal, the current due to the charges induced in the counter electrode by this vibration.

Example

[0317] Hereinafter, an aspect of the present disclosure will be described in more detail based on examples, but the present invention is not construed as being limited to these examples in any way. The analytical instruments used in this example are listed below.

[0318] [Measurement of glass transition temperature] Measuring device: DSC7020 manufactured by Hitachi High-Tech Science Corporation, Measurement method: A 5 mg sample was placed in an aluminum sample pan and measured under heating conditions of 10 °C / min. [Measurement of giant surface potential] Measuring device: Kasuga Electric KSD-3000, Measurement method: The measuring device was grounded, and the charged film and the measurement probe were placed in an electrostatic shield for measurement. A distance of 10 mm was maintained between the charged film and the measurement probe, and the measurement range was 20 mm × 20 mm. [Measurement of electrical resistivity] Measuring device: Keithley6487 manufactured by Tektronix, Measurement method: The current when the applied voltage was 1 V was measured, and the electrical resistivity was calculated.

[0319] Example 1 Synthesis of Compound (A177)

Chemical formula

[0320] Under a nitrogen atmosphere, 4,4'-diaminooctafluorobiphenyl (1.64 g, 5.0 mmol), perfluorotoluene (14 ml, 100 mmol), and potassium carbonate (3.46 g, 25 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100 °C for 12 hours. After cooling to room temperature, water (100 ml), toluene (20 ml), and methanol (30 ml) were added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration to obtain the target compound (A177) as a white solid (yield 5.12 g, yield 86%). The glass transition temperature of compound (A177) was 102 °C. 19 F-NMR (376.4 MHz, CDCl 3 ) δ (ppm): -57.3 (t, J = 17.3 Hz, 12F), -136.6 (s, 4F), -139.5 (s, 8F), -148.1 (d, J = 17.3 Hz, 8F), -148.5 (s, 4F).

[0321] Example 1A Evaluation of Compound (A177): Giant Surface Potential A 25 mm × 25 mm glass substrate was subjected to boiling cleaning with isopropyl alcohol and further ultraviolet ozone cleaning, and then placed in a vacuum evaporation apparatus and evacuated with a vacuum pump until the pressure reached 1.0 × 10 -4 Pa or less. Films with the following eight film thicknesses (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm) of compound (A177) were formed on the glass substrate with a metal mask having an opening of 25 mm × 25 mm at a deposition rate of 0.2 nm / second. Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -11 mV / nm.

[0322] Example 1B Evaluation of Compound (A177): Surface Potential Retention Rate A 25 mm × 25 mm glass substrate was subjected to boiling cleaning with isopropyl alcohol and further ultraviolet ozone cleaning, and then placed in a vacuum evaporation apparatus and evacuated with a vacuum pump until the pressure reached 1.0 × 10 -4Exhausted with a vacuum pump until the pressure reached below Pa. Compound (A177) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 1000 nm on a glass substrate on which a metal mask with an opening of 25 mm × 25 mm was placed. The film was irradiated with light (wavelength range: 250 nm or more, irradiance: 0.9 mW / cm 2 @254 nm, irradiation time: 200 s) in the atmosphere. The retention rate of the surface potential was 0.97, and the large surface potential of A177 was stable against light. Further, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The retention rate of the surface potential was 0.94, and the large surface potential of A177 was stable against long-term storage under light irradiation. In addition, under the above light irradiation conditions, "wavelength range: 250 nm or more, irradiance: 0.9 mW / cm 2 @254 nm" means that when light with a wavelength of 250 nm or more is applied, the radiation intensity at 254 nm is 0.9 mW / cm 2 . In the light irradiation conditions described below, when the numerical values of the wavelength range or the irradiance are different, the light irradiation conditions described below mean those in which the numerical values in the above definition are replaced with the numerical values in the light irradiation conditions described below.

[0323] Example 1C Evaluation of Compound (A177): Electrical Resistivity A 25 mm × 25 mm glass substrate was subjected to boiling cleaning with isopropyl alcohol and further ultraviolet ozone cleaning, and then installed in a vacuum deposition apparatus. 1.0 × 10 -4Exhausted with a vacuum pump until the pressure reached below Pa. A metal mask with an opening of 4.0 mm × 2.0 mm was placed at a position 1 mm shifted to the left from the center of the glass substrate, and copper was deposited at a deposition rate of 0.1 nm / second to form a 100-nm film to create the lower electrode. Next, a metal mask with an opening of 2.0 mm × 2.0 mm was placed at the center of the glass substrate, and compound (A177) was deposited at a deposition rate of 0.1 nm / second to form a 2000-nm film. Finally, a metal mask with an opening of 4.0 mm × 2.0 mm was placed at a position 1 mm shifted to the right from the center of the glass substrate, and copper was deposited at a deposition rate of 0.1 nm / second to form a 100-nm film to create the upper electrode. With the lower electrode as the cathode and the upper electrode as the anode, the electrical resistivity of compound (A177) was measured. The electrical resistivity of compound (A177) was 1×10 13 Ωm.

[0324] Example 2 Synthesis of Compound (A512)

Chemical formula

[0325] Under a nitrogen atmosphere, 1,3-diaminoadamantane (1.30 g, 7.8 mmol), perfluorotoluene (14.8 g, 62.5 mmol), 18-crown-6 ether (103 mg, 0.40 mmol), and tripotassium phosphate (16.6 g, 78.2 mmol) were suspended in dimethyl sulfoxide (40 ml) and stirred at 100 °C for 24 hours. After cooling to room temperature, water (50 ml) and methanol (50 ml) were added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration to obtain the target compound (A512) as a white solid (yield 6.90 g, yield 86%). The glass transition temperature of compound (A512) was 70 °C. 1 H-NMR (400 MHz, CDCl 3 ); 2.34 (s, 2H), 2.01 (s, 2H), 1.91 (d, J = 12.0, 4H), 1.72 (d, J = 12.0, 4H), 1.58 (s, 2H) 19 F-NMR (376.4 MHz, CDCl 3)δ(ppm): -57.5 to -57.7 (m, 12F), -138.1 (s, 8F), -141.3 (d, J = 23.7Hz, 8F).

[0326] Example 2A Evaluation of Compound (A512): Giant Surface Potential Using the same method as in Example 1A, films of eight film thicknesses of compound (A512) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -66 mV / nm.

[0327] Example 2B Evaluation of Compound (A512): Surface Potential Retention Rate Using the same method as in Example 1B, a film of compound (A512) was prepared. The film was irradiated with light under air (wavelength range: 250 nm or more, irradiance: 0.9 mW / cm 2 @254 nm, irradiation time: 200 s). The surface potential retention rate was 0.99, and the giant surface potential of A512 was stable against light. The results are shown in Figure 1. Furthermore, a new film with a film thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation under air. The surface potential retention rate was 0.98, and the giant surface potential of A512 was stable against long-term storage under light irradiation.

[0328] Example 2C Evaluation of Compound (A512): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A512) was measured. The electrical resistivity of compound (A512) was 1×10 13 Ωm.

[0329] Example 3 Synthesis of Compound (A774)

Chemical Structure

[0330] Under a nitrogen atmosphere, perfluorobiphenyl (5.0 mmol), 4,5-bis(nonafluorobutyl)catechol (11.0 mmol), and potassium carbonate (3.46 g, 40 mmol) were suspended in dimethylformamide (50 mL) and stirred at 100 °C for 12 hours. After cooling to room temperature, water (200 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration, washed with methanol (200 mL), and purified by sublimation to obtain the target compound (A774) as a white solid (yield 50%). The compound was identified by FDMS measurement. FDMS: 1346

[0331] Example 3A Evaluation of Compound (A774): Giant Surface Potential Using the same method as in Example 1A, films of eight thicknesses of compound (A774) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -64 mV / nm.

[0332] Example 3B Evaluation of Compound (A774): Surface Potential Retention Rate Using the same method as in Example 1B, a film of compound (A774) was prepared. The film was irradiated with light (wavelength range: 250 nm or more, irradiance: 0.3 mW / cm 2 @254 nm, irradiation time: 50 s). The surface potential retention rate was 0.91, and the giant surface potential of A774 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed and stored under indoor light irradiation in air for 1000 hours. The surface potential retention rate was 0.92, and the giant surface potential of A774 was stable against long-term storage under light irradiation.

[0333] Example 3C Evaluation of Compound (A774): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A774) was measured. The electrical resistivity of compound (A774) was 3×10 13 Ωm.

[0334] Example 4 Synthesis of Compound (A581)

Chem.

[0335] Under a nitrogen atmosphere, adamantane-1,3-diamine, N 1 ,N 3 -bis[2,3,5,6-tetrafluoro-4-[bis(perfluorotolyl)amino]phenyl]-(4.07 g, 3.0 mmol), perfluorobenzene (2.12 g, 9.0 mmol), 18-crown-6 ether (39.6 mg, 0.15 mmol), tripotassium phosphate (3.18 g, 15.0 mmol) were suspended in dimethyl sulfoxide (40 mL) and stirred at 100 °C for 24 h. After cooling to room temperature, water (40 ml) and methanol (40 ml) were added to the reaction solution and stirred at room temperature for 30 min. The desired compound (A581) as a white solid was obtained by filtering the precipitated solid (yield 3.85 g, yield 72%). The glass transition temperature of compound (A581) was 127 °C. 1 H-NMR (400 MHz, THF-d 8 ); 2.21 (s, 2H), 1.93 (s, 2H), 1.81~1.68 (m, 8H), 1.45 (s, 2H) 19 F-NMR (376.4 MHz, THF-d 8 ) δ (ppm): -55.6~-55.9 (m, 18F), -136.8~-137.0 (m, 4F), -137.4~-137.6 (m, 4F), -139.3~-139.6 (m, 8F), -141.2~-141.4 (m, 4F), -146.9~-147.0 (m, 8F), -148.8~-149.0 (m, 4F).

[0336] Example 4A Evaluation of Compound (A581): Giant Surface Potential Using the same method as in Example 1A, films of eight thicknesses of compound (A581) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -71 mV / nm.

[0337] Example 4B Evaluation of Compound (A581): Retention Rate of Surface Potential A film of compound (A581) was prepared using the same method as in Example 1B. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The retention rate of the surface potential was 0.99, and the giant surface potential of A581 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The retention rate of the surface potential was 0.96, and the giant surface potential of A581 was stable against long-term storage under light irradiation.

[0338] Example 4C Evaluation of Compound (A581): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A581) was measured. The electrical resistivity of compound (A581) was 2×10 13 Ωm.

[0339] Example 5 Synthesis of Compound (A584) [Chemical formula]

[0340] Under a nitrogen atmosphere, 2,2-bis(4-aminophenyl)hexafluoropropane (2.00 g, 6.0 mmol), perfluorotoluene (11.4 g, 48.0 mmol), tripotassium phosphate (12.8 g, 60.0 mmol), and 18-crown-6 ether (103 mg, 0.40 mmol) were suspended in dimethyl sulfoxide (60 mL) and stirred at 100 °C for 24 hours. After cooling to room temperature, water (120 ml) and methanol (50 ml) were added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration to obtain the target compound (A584) as a white solid (yield 4.06 g, yield 57%). The glass transition temperature of compound (A584) was 88 °C. 1 H-NMR(400MHz,CDCl 3 );7.36(d,J=4.00,4H),6.92(d,J=4.00,4H) 19 F-NMR(376.4MHz,CDCl 3 )δ(ppm):-57.3(t,J=22.6Hz,12F),-65.2(s,6F),-139.9~-140.1(m,8F),-144.9~-145.0(m,8F).

[0341] Example 5A Evaluation of Compound (A584): Giant Surface Potential Using the same method as in Example 1A, films of eight thicknesses of compound (A584) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -52 mV / nm.

[0342] Example 5B Evaluation of Compound (A584): Surface Potential Retention Rate Using the same method as in Example 1B, a film of compound (A584) was prepared. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2(@365 nm, irradiation time: 50 s). The surface potential retention rate was 0.95, and the large surface potential of A584 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The surface potential retention rate was 0.91, and the large surface potential of A584 was stable against long-term storage under light irradiation.

[0343] Example 5C Evaluation of Compound (A584): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A584) was measured. The electrical resistivity of compound (A584) was 1×10 13 Ωm.

[0344] Example 6 Synthesis of Compound (A589)

Chemical Structure

[0345] Under a nitrogen atmosphere, 1,4-adamantanediamine, 2,3,5,6-tetrafluoro-N 4 -phenyl-N 1 -[2,3,5,6-tetrafluoro-4-(adamantylamino)phenyl]-N 1 -[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-(2.07 g, 2.5 mmol), perfluorotoluene (1.77 g, 7.5 mmol), 18-crown-6 ether (33.0 mg, 0.13 mmol), tripotassium phosphate (2.65 g, 12.5 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100 °C for 24 hours. After cooling to room temperature, water (50 ml) and methanol (50 ml) were added to the reaction solution and stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration to obtain the target compound (A589) as a white solid (yield 2.46 g, yield 78%). The glass transition temperature of compound (A526) was 138 °C. 1 H-NMR (400 MHz, CDCl 3 ); 2.15 (s, 6H), 1.87 (s, 12H), 1.69~1.60 (m, 12H) 19 F-NMR (376.4 MHz, CDCl 3 ) δ (ppm): -57.2 to -57.5 (m, 9F), -138.0 to -138.2 (m, 4F), -138.7 to -138.8 (m, 4F), -140.3 to -140.4 (m, 2F), -142.1 to -142.4 (m, 4F), -148.5 to -148.6 (m, 2F), -150.6 to -150.7 (m, 4F).

[0346] Example 6A Evaluation of Compound (A589): Giant Surface Potential Using the same method as in Example 1A, films of eight film thicknesses of Compound (A589) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -48 mV / nm.

[0347] Example 6B Evaluation of Compound (A589): Surface Potential Retention Rate Using the same method as in Example 1B, a film of Compound (A589) was prepared. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The surface potential retention rate was 0.90, and the giant surface potential of A589 was stable against light. Furthermore, a new film with a film thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The surface potential retention rate was 0.90, and the giant surface potential of A589 was stable against long-term storage under light irradiation.

[0348] Example 6C Evaluation of Compound (A589): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of Compound (A589) was measured. The electrical resistivity of Compound (A589) was 1×10 13 Ωm.

[0349] Example 7 Synthesis of Compound (A591)

Chemical Structure

[0350] Under a nitrogen atmosphere, adamantane-1,3-diamine, N 1 ,N 3 -bis(2,2’,3,3’,4’,5,5’,6,6’-nonafluoro[1,1’-biphenyl]-4-yl)-(2.38 g, 3.0 mmol), perfluorotoluene (2.12 g, 9.0 mmol), 18-crown-6 ether (793 mg, 3.0 mmol), and tripotassium phosphate (3.18 g, 15.0 mmol) were suspended in dimethyl sulfoxide (30 mL) and stirred at 100 °C for 24 hours. After cooling to room temperature, water (30 mL) and methanol (30 mL) were added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration to obtain the target compound (A591) as a white solid (yield 3.02 g, 82%). The glass transition temperature of compound (A591) was 93 °C. 1 H-NMR (400 MHz, THF-d 8 ); 2.36 (s, 2H), 2.18 (s, 2H), 2.01~1.86 (m, 8H), 1.62 (s, 2H) 19 F-NMR (376.4 MHz, THF-d 8 ) δ (ppm): -57.8 (t, J = 22.6 Hz, 6F), -136.6~-136.7 (m, 4F), -137.3~-137.5 (m, 4F), -138.0~-138.1 (m, 4F), -138.6~-138.7 (m, 4F), -141.3~-141.5 (m, 4F), -150.8~-150.9 (m, 2F), -161.2~-161.3 (m, 4F).

[0351] Example 7A Evaluation of Compound (A591): Giant Surface Potential Using the same method as in Example 1A, films of eight thicknesses of compound (A591) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -32 mV / nm.

[0352] Example 7B Evaluation of Compound (A591): Maintenance Rate of Surface Potential A film of compound (A591) was prepared using the same method as in Example 1B. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The maintenance rate of the surface potential was 0.94, and the large surface potential of A591 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The maintenance rate of the surface potential was 0.93, and the large surface potential of A591 was stable against long-term storage under light irradiation.

[0353] Example 7C Evaluation of Compound (A591): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A591) was measured. The electrical resistivity of compound (A591) was 2×10 13 Ωm.

[0354] Example 8 Synthesis of Compound (A600) [Chemical formula]

[0355] Under a nitrogen atmosphere, 1,4-benzenediamine, N 4 -2-dibenzofuranyl-2,3,5,6-tetrafluoro-N 1 ,N 1 -bis[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-(3.11 g, 4.0 mmol), perfluorotoluene (2.83 g, 12 mmol), and tripotassium phosphate (4.25 g, 20 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100 °C for 24 hours. After cooling to room temperature, water (50 ml) and methanol (50 ml) were added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration to obtain the target compound (A600) as a white solid (yield 2.57 g, yield 65%). The identification of the compound was performed by FDMS measurement. FDMS:994

[0356] Example 8A Evaluation of Compound (A600): Giant Surface Potential Using the same method as in Example 1A, films of eight thicknesses of Compound (A600) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -43 mV / nm.

[0357] Example 8B Evaluation of Compound (A600): Surface Potential Retention Rate Using the same method as in Example 1B, a film of Compound (A600) was prepared. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The surface potential retention rate was 0.89, and the giant surface potential of A600 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed and stored for 1000 hours under indoor light irradiation in the air. The surface potential retention rate was 0.90, and the giant surface potential of A600 was stable against long-term storage under light irradiation.

[0358] Example 8C Evaluation of Compound (A600): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of Compound (A600) was measured. The electrical resistivity of Compound (A600) was 9×10 12 Ωm.

[0359] Example 9 Synthesis of Compound (A663) [Chemical formula]

[0360] Under a nitrogen atmosphere, 1,4-benzenediamine, N 4 -1-naphthyl-2,3,5,6-tetrafluoro-N 1 ,N 1-Bis[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-(2.95 g, 4.0 mmol), perfluorotoluene (2.83 g, 12 mmol), and tripotassium phosphate (4.25 g, 20 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100 °C for 24 hours. After cooling to room temperature, the mixture was separated with pure water and chloroform, and the organic layer was further washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A663) as a white solid (yield 3.25 g, yield 85%). The identification of the compound was carried out by FDMS measurement. FDMS: 954

[0361] Example 9A Evaluation of Compound (A663): Giant Surface Potential Using the same method as in Example 1A, films of eight film thicknesses of compound (A663) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -49 mV / nm.

[0362] Example 9B Evaluation of Compound (A663): Surface Potential Retention Rate Using the same method as in Example 1B, a film of compound (A663) was prepared. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The surface potential retention rate was 0.86, and the giant surface potential of A663 was stable against light. Furthermore, a new film with a film thickness of 1000 nm was formed and stored under indoor light irradiation in air for 1000 hours. The surface potential retention rate was 0.86, and the giant surface potential of A663 was stable against long-term storage under light irradiation.

[0363] Example 9C Evaluation of Compound (A663): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A663) was measured. The electrical resistivity of compound (A663) was 8×10 12 Ωm.

[0364] Example 10 Synthesis of Compound (A602) [Chemical formula]

[0365] Under a nitrogen atmosphere, 1,4-benzenediamine, N 4 -2-dibenzothienyl-2,3,5,6-tetrafluoro-N 1 ,N 1 -bis[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-(3.18 g, 4.0 mmol), perfluorotoluene (2.83 g, 12 mmol), and tripotassium phosphate (4.25 g, 20 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100 °C for 24 hours. After allowing to cool to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was further washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A602) as a white solid (yield 2.69 g, yield 67%). The identification of the compound was performed by FDMS measurement. FDMS: 1010

[0366] Example 10A Evaluation of Compound (A602): Giant Surface Potential Using the same method as in Example 1A, films of eight film thicknesses of compound (A602) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -51 mV / nm.

[0367] Example 10B Evaluation of Compound (A602): Surface Potential Retention Rate A film of compound (A602) was prepared using the same method as in Example 1B. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The retention rate of the surface potential was 0.91, and the large surface potential of A602 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The retention rate of the surface potential was 0.90, and the large surface potential of A602 was stable against long-term storage under light irradiation.

[0368] Example 10C Evaluation of compound (A602): Electrical resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A602) was measured. The electrical resistivity of compound (A602) was 1×10 13 Ωm.

[0369] Example 11 Synthesis of compound (A699)

Chemical formula

[0370] Under a nitrogen atmosphere, [1,1'-biphenyl]-4-amine, 2,2',3,3',4,5,5',6,6'-nonafluoro-N-(2,3,5,6-tetrafluoro-4-adamantyl-1-phenyl)-(2.45 g, 4.0 mmol), perfluorotoluene (2.83 g, 12 mmol), and tripotassium phosphate (4.25 g, 20 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100 °C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was further washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A699) as a white solid (yield 2.51 g, yield 76%). The identification of the compound was performed by FDMS measurement. FDMS: 829

[0371] Example 11A Evaluation of Compound (A699): Giant Surface Potential Using the same method as in Example 1A, films of eight thicknesses of compound (A699) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -58 mV / nm.

[0372] Example 11B Evaluation of Compound (A699): Maintenance Rate of Surface Potential Using the same method as in Example 1B, a film of compound (A699) was prepared. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The maintenance rate of the surface potential was 0.98, and the giant surface potential of A699 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The maintenance rate of the surface potential was 0.98, and the giant surface potential of A699 was stable against long-term storage under light irradiation.

[0373] Example 11C Evaluation of Compound (A699): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A699) was measured. The electrical resistivity of compound (A699) was 2×10 13 Ωm.

[0374] Example 12 Synthesis of Compound (A710)

Chemical Structure

[0375] Under a nitrogen atmosphere, 2,8-diaminodibenzofuran (0.991 g, 5.0 mmol), perfluorotoluene (9.44 g, 40 mmol), and tripotassium phosphate (10.6 g, 50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 100 °C for 24 hours. After cooling to room temperature, water (50 mL) and methanol (50 mL) were added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration to obtain the target compound (A710) as a white solid (yield 4.15 g, yield 78%). The identification of the compound was performed by FDMS measurement. FDMS: 1062

[0376] Example 12A Evaluation of Compound (A710): Giant Surface Potential Using the same method as in Example 1A, films of eight thicknesses of compound (A710) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was +31 mV / nm.

[0377] Example 12B Evaluation of Compound (A710): Surface Potential Retention Rate Using the same method as in Example 1B, a film of compound (A710) was prepared. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The surface potential retention rate was 0.84, and the giant surface potential of A710 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed and stored in air under indoor light irradiation for 1000 hours. The surface potential retention rate was 0.84, and the giant surface potential of A710 was stable against long-term storage under light irradiation.

[0378] Example 12C Evaluation of Compound (A710): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A710) was measured. The electrical resistivity of compound (A710) was 8×10 12 Ωm.

[0379] Example 13 Synthesis of Compound (A800) [Chemical formula]

[0380] Under a nitrogen atmosphere, 1,4-bis(4,6-dichloro-1,3,5-triazin-2-yl)piperidine (5.0 mmol), tripotassium phosphate (25.0 mmol), and 1H,1H,7H-dodecafluoro-1-heptanol (22.0 mmol) were suspended in tetrahydrofuran (60 ml) and stirred at 70 °C for 30 hours. After cooling to room temperature, water (100 ml) was added to the reaction solution, and the precipitated solid was collected by filtration to obtain the white target compound (A800) (yield 66.2%). The compound was identified by FDMS measurement. FDMS: 1564

[0381] Example 13A Evaluation of Compound (A800): Giant Surface Potential Using the same method as in Example 1A, films of eight thicknesses of compound (A800) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -5 mV / nm.

[0382] Example 13B Evaluation of Compound (A800): Surface Potential Retention Rate Using the same method as in Example 1B, a film of compound (A800) was prepared. The film was irradiated with light (wavelength range: 250 nm or more, irradiance: 0.3 mW / cm 2 @254 nm, irradiation time: 50 s). The surface potential retention rate was 0.91, and the giant surface potential of A800 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed and stored for 1000 hours under indoor light irradiation in the atmosphere. The surface potential retention rate was 0.90, and the giant surface potential of A800 was stable against long-term storage under light irradiation.

[0383] Example 13C Evaluation of Compound (A800): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of Compound (A800) was measured. The electrical resistivity of Compound (A800) was 3×10 13 Ωm.

[0384] Example 14 Synthesis of Compound (A862) [Chemical Structure]

[0385] Under a nitrogen atmosphere, [1,1'-biphenyl]-4,4'-diamine, 2,2,3,3,5,5,6,6-octafluoro-N 4 ,N 4’ -bis(2,3,5,6-tetrafluoro-4-pyridyl)-(5.0 mmol), perfluorobenzene (100 mmol), and cesium carbonate (50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 80 °C for 24 hours. After allowing to cool to room temperature, liquid separation was carried out using pure water and chloroform, and the organic layer was further washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target compound (A862) as a white solid (yield 33%). The identification of the compound was carried out by FDMS measurement. FDMS: 958

[0386] Example 14A Evaluation of Compound (A862) Using the same method as in Example 1A, films of 8 types of film thicknesses of Compound (A862) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -29 mV / nm.

[0387] Example 14B Evaluation of Compound (A862): Maintenance Rate of Surface Potential A film of compound (A862) was prepared using the same method as in Example 1B. The film was irradiated with light (wavelength range: 250 nm or more, irradiance: 0.3 mW / cm 2 @254 nm, irradiation time: 50 s). The maintenance rate of the surface potential was 0.98, and the large surface potential of A862 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The maintenance rate of the surface potential was 0.98, and the large surface potential of A862 was stable against long-term storage under light irradiation.

[0388] Example 14C Evaluation of compound (A862): Electrical resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A862) was measured. The electrical resistivity of compound (A862) was 2×10 13 Ωm.

[0389] Example 15 Synthesis of compound (A867) [Chemical formula]

[0390] Under a nitrogen atmosphere, 1,3-benzenediamine, 2,4,5,6-N 1 ,N 3 -bis(2,3,5,6-tetrafluoro-4-pyridyl)-(5.0 mmol), perfluorobiphenyl (100 mmol), and cesium carbonate (50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 80 °C for 24 hours. After allowing to cool to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was further washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A867) as a white solid (yield 18%). The identification of the compound was performed by FDMS measurement. FDMS: 1106

[0391] Example 15A Evaluation of compound (A867): Maintenance rate of surface potential Using the same method as in Example 1A, films of eight thicknesses of compound (A867) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -35 mV / nm.

[0392] Example 15B Evaluation of Compound (A867): Electrical Resistivity A film of compound (A867) was prepared using the same method as in Example 1B. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The maintenance rate of the surface potential was 0.97, and the giant surface potential of A867 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The maintenance rate of the surface potential was 0.96, and the giant surface potential of A867 was stable against long-term storage under light irradiation.

[0393] Example 15C Evaluation of Compound (A867): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A867) was measured. The electrical resistivity of compound (A867) was 1×10 13 Ωm.

[0394] Example 16 Synthesis of Compound (A873)

Chemical Structure

[0395] Under a nitrogen atmosphere, 9-phenyl-3,6-diaminocarbazole (5.0 mmol), perfluorobenzene (15.0 mmol), and cesium carbonate (50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 80 °C for 6 hours. Subsequently, perfluoropyridine (50.0 mmol) was added and the mixture was stirred at 80 °C for 24 hours. After allowing to cool to room temperature, the mixture was separated with pure water and chloroform, and the organic layer was further washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A873) as a white solid (yield 31%). The identification of the compound was performed by FDMS measurement. FDMS: 903

[0396] Example 16A Evaluation of Compound (A873): Giant Surface Potential Using the same method as in Example 1A, films of eight film thicknesses of compound (A873) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured and the slope of the giant surface potential was determined. The slope of the giant surface potential was -46 mV / nm.

[0397] Example 16B Evaluation of Compound (A873): Surface Potential Retention Rate Using the same method as in Example 1B, a film of compound (A873) was prepared. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The surface potential retention rate was 0.86, and the giant surface potential of A873 was stable against light. Furthermore, a new film with a film thickness of 1000 nm was formed and stored for 1000 hours under indoor light irradiation in the atmosphere. The surface potential retention rate was 0.85, and the giant surface potential of A873 was stable against long-term storage under light irradiation.

[0398] Example 16C Evaluation of Compound (A873): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A873) was measured. The electrical resistivity of compound (A873) was 8×10 12 Ωm.

[0399] Example 17A Evaluation of Compound (A951): Giant Surface Potential [Chemical formula]

[0400] Using the same method as in Example 1A, films of eight thicknesses of compound (A951) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -15 mV / nm.

[0401] Example 17B Evaluation of Compound (A951): Surface Potential Retention Rate Using the same method as in Example 1B, a film of compound (A951) was prepared. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The surface potential retention rate was 0.91, and the giant surface potential of A951 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The surface potential retention rate was 0.90, and the giant surface potential of A951 was stable against long-term storage under light irradiation.

[0402] Example 17C Evaluation of Compound (A951): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A951) was measured. The electrical resistivity of compound (A951) was 1×10 13 Ωm.

[0403] Example 18 Synthesis of Compound (A962) [Chemical formula]

[0404] Under a nitrogen atmosphere, [1,1'-biphenyl]-4,4'-diamine, 2,2',3,3',5,5',6,6'-octafluoro-N 4 ,N 4’ -bis(2,3,5,6-tetrafluoro-4-adamantylphenyl)-(5.0 mmol), perfluoropyridine (100 mmol), and cesium carbonate (50 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 80 °C for 24 hours. After allowing to cool to room temperature, the mixture was separated with pure water and chloroform, and the organic layer was further washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (A962) as a white solid (yield 43%). The identification of the compound was performed by FDMS measurement. FDMS: 1190

[0405] Example 18A Evaluation of Compound (A962): Giant Surface Potential Using the same method as in Example 1A, films of eight film thicknesses of compound (A962) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -19 mV / nm.

[0406] Example 18B Evaluation of Compound (A962): Surface Potential Retention Rate Using the same method as in Example 1B, a film of compound (A962) was prepared. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2 @365 nm, irradiation time: 50 s). The surface potential retention rate was 0.90, and the giant surface potential of A962 was stable against light. Furthermore, a film with a new film thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The surface potential retention rate was 0.90, and the giant surface potential of A962 was stable against long-term storage under light irradiation.

[0407] Example 18C: Evaluation of Compound (A962) - Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of Compound (A962) was measured. The electrical resistivity of Compound (A962) was 1×10 13 Ωm.

[0408] Example 19: Synthesis of Compound (A960) [Chemical formula]

[0409] Under a nitrogen atmosphere, N1,N4-bis(adamantan-1-yl)-1,4-benzenediamine (3.0 mmol), perfluorobenzene (9.0 mmol), 18-crown-6 ether (0.15 mmol), and tripotassium phosphate (15.0 mmol) were suspended in dimethyl sulfoxide (40 mL) and stirred at 100 °C for 24 hours. After cooling to room temperature, water (40 ml) and methanol (40 ml) were added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration to obtain the target compound (A960) as a white solid (yield 72%). The compound was identified by FDMS measurement. FDMS: 808

[0410] Example 19A: Evaluation of Compound (A960) - Giant Surface Potential Using the same method as in Example 1A, films of eight thicknesses of Compound (A960) were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -24 mV / nm.

[0411] Example 19B: Evaluation of Compound (A960) - Surface Potential Retention Rate Using the same method as in Example 1B, a film of Compound (A960) was prepared. The film was irradiated with light (wavelength range: 350 nm or more, irradiance: 0.3 mW / cm 2(@365 nm, irradiation time: 50 s). The maintenance rate of the surface potential was 0.85, and the large surface potential of A960 was stable against light. Furthermore, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The maintenance rate of the surface potential was 0.82, and the large surface potential of A960 was stable against long-term storage under light irradiation.

[0412] Example 19C Evaluation of Compound (A960): Electrical Resistivity Using the same method as in Example 1C, the electrical resistivity of compound (A960) was measured. The electrical resistivity of compound (A960) was 1×10 13 Ωm.

[0413] Comparative Example 1A Evaluation of Tris(8-quinolinolato)aluminum (hereinafter referred to as "X1"): Large Surface Potential

Chemical formula

[0414] Manufacturer: Purchased from Tokyo Chemical Industry Product Name: Alq 3 (purified by sublimation)

[0415] Using the same method as in Example 1, films with 8 types of thicknesses of X1 were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the large surface potential was determined. The slope of the large surface potential was +48 mV / nm.

[0416] Comparative Example 1B Evaluation of X1: Maintenance Rate of Surface Potential Using the same method as in Example 1B, a film of X1 was prepared. The film was irradiated with light (wavelength range: 250 nm or more, irradiance: 0.3 mW / cm 2(At 254 nm, irradiation time: 20 s). The maintenance rate of the surface potential was 0.13, and the large surface potential of X1 was not stable against light. The results are shown in Fig. 2. Further, a film with a new film thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The maintenance rate of the surface potential was 0.10, and the large surface potential of X1 was not stable against long-term storage under light irradiation.

[0417] Comparative Example 1C Evaluation of X1: Electrical Resistivity Using the same method as in Example 1A, the electrical resistivity of X1 was measured. The electrical resistivity of X1 was 1×10 9 Ωm. The electrical resistivity of X1 was a small value.

[0418] Comparative Example 2A Evaluation of 2,2’,2”-(1,3,5-benzenetriyl)-tris(1-phenyl-1-H-benzimidazole) (hereinafter referred to as “X2”): Large Surface Potential

Chemical formula

[0419] Manufacturer: Purchased from Tokyo Chemical Industry Product Name: TPBi

[0420] Using the same method as in Example 1, films of 8 types of film thicknesses of X2 were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the large surface potential was determined. The slope of the large surface potential was +66 mV / nm.

[0421] Comparative Example 2B Evaluation of X2: Maintenance Rate of Surface Potential Using the same method as in Example 1B, a film of X2 was prepared. Light was irradiated on the film (wavelength range: 250 nm or more, irradiance: 0.3 mW / cm 2(At 254 nm, irradiation time: 20 s). The maintenance rate of the surface potential was 0.15, and the large surface potential of X2 was not stable against light. Furthermore, a new film with a thickness of 1000 nm was formed, and the film was stored for 1000 hours under indoor light irradiation in the atmosphere. The maintenance rate of the surface potential was 0.13, and the large surface potential of X2 was not stable against long-term storage under light irradiation.

[0422] Comparative Example 2C Evaluation of X2: Electrical Resistivity Using the same method as in Example 1A, the electrical resistivity of X2 was measured. The electrical resistivity of X2 was 1×10 9 Ωm. The electrical resistivity of X2 was a small value.

[0423] Comparative Example 3A Evaluation of N,N,N’,N’-tetrakis(p-tolyl)benzidine (hereinafter referred to as "X3"): Large Surface Potential [Chemical formula]

[0424] Manufacturer: Purchased from Tokyo Chemical Industry Product Name: N,N,N’,N’-tetrakis(p-tolyl)benzidine (sublimation purified product)

[0425] Using the same method as in Example 1, films of 8 types of thicknesses of X3 were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the large surface potential was determined. The slope of the large surface potential was +9.0 mV / nm.

[0426] Comparative Example 3B Evaluation of X3: Maintenance Rate of Surface Potential Using the same method as in Example 1B, a film of X3 was prepared. Light was irradiated on the film (wavelength range: 250 nm or more, irradiance: 0.3 mW / cm 2(At 254 nm, irradiation time: 20 s). The maintenance rate of the surface potential was 0.18, and the large surface potential of X3 was not stable against light. Further, a film with a thickness of 1000 nm was newly formed and stored for 100 hours under indoor light irradiation in the atmosphere. The maintenance rate of the surface potential was 0.15, and the large surface potential of X3 was not stable against long-term storage under light irradiation.

[0427] Comparative Example 3C Evaluation of X3: Electrical Resistivity Using the same method as in Example 1, the electrical resistivity of X3 was measured. The electrical resistivity of X3 was 4×10 9 Ωm. The electrical resistivity of X3 was a small value.

[0428] Comparative Example 4 Synthesis of [1,1'-biphenyl]-4,4'-diamine, N 4’ -(4-trifluoromethyl-2,3,5,6-fluorophenyl)-N 4’ -[1,1'-biphenyl]-4-yl-N 4 ,N 4 -biphenyl- (hereinafter referred to as "X4")

Chemical Formula

[0429] Under a nitrogen atmosphere, [1,1'-biphenyl]-4,4'-diamine, N 4’ -[1,1'-biphenyl]-4-yl-N 4 ,N 4 -biphenyl- (7.8 mmol), perfluorotoluene (39 mmol), 18-crown-6 ether (0.40 mmol), and tripotassium phosphate (78.2 mmol) were suspended in dimethyl sulfoxide (40 ml) and stirred at 100 °C for 24 hours. After cooling to room temperature, water (50 ml) and methanol (50 ml) were added to the reaction solution and stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration to obtain the target compound (X4), a white solid (yield 56%). The identification of the compound was performed by FDMS measurement. FDMS: 704

[0430] Evaluation of Comparative Example 4A X4: Giant Surface Potential In the same manner as in Example 1, films of eight film thicknesses of X4 were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -34 mV / nm.

[0431] Evaluation of Comparative Example 4B X4: Maintenance Rate of Surface Potential A film of X4 was prepared using the same method as in Example 1B. The film was irradiated with light (wavelength range: 250 nm or more, irradiance: 0.3 mW / cm 2 @254 nm, irradiation time: 20 s). The maintenance rate of the surface potential was 0.23, and the giant surface potential of X4 was not stable against light. Furthermore, a film with a new film thickness of 1000 nm was formed and stored for 100 hours under indoor light irradiation in the atmosphere. The maintenance rate of the surface potential was 0.20, and the giant surface potential of X4 was not stable against long-term storage under light irradiation.

[0432] Evaluation of Comparative Example 4C X4: Electrical Resistivity Using the same method as in Example 1, the electrical resistivity of X4 was measured. The electrical resistivity of X4 was 2×10 10 Ωm. The electrical resistivity of X4 was a small value.

[0433] Evaluation of Comparative Example 5A 1,2,4,5-Tetrakis(3’,4’,5’-trifluoro-1,1’-biphenyl)benzene (hereinafter referred to as X5): Giant Surface Potential

Chemical formula

[0434] In the same manner as in Example 1, films of eight film thicknesses of X5 were prepared (100 nm, 200 nm, 300 nm, 500 nm, 1000 nm, 2000 nm, 4000 nm, 5000 nm). Subsequently, the surface potential of all the films was measured, and the slope of the giant surface potential was determined. The slope of the giant surface potential was -12 mV / nm.

[0435] Evaluation of Comparative Example 5B X5: Retention rate of surface potential A film of X5 was prepared using the same method as in Example 1B. The film was irradiated with light (wavelength range: 250 nm or more, irradiance: 0.3 mW / cm 2 @254 nm, irradiation time: 20 s). The retention rate of the surface potential was 0.25, and the large surface potential of X5 was not stable against light. Further, a new film with a thickness of 1000 nm was formed and stored for 100 hours under indoor light irradiation in the atmosphere. The retention rate of the surface potential was 0.21, and the large surface potential of X5 was not stable against long-term storage under light irradiation.

[0436] Evaluation of Comparative Example 5C X5: Electrical resistivity Using the same method as in Example 1, the electrical resistivity of X5 was measured. The electrical resistivity of X5 was 4×10 10 Ωm. The electrical resistivity of X5 was a small value.

[0437] Table 1 shows the results of the above-described Examples and Comparative Examples and the ratio of the number of fluorine atoms to the total number of carbon atoms in the whole molecule of each compound (described as "fluorine ratio" in the table).

[0438] [Table 1]

[0439] This disclosure includes the following embodiments. [1] A chargeable material containing a compound having at least one selected from the group consisting of an aromatic ring and a heteroaromatic ring in the molecule, wherein the ring is substituted with at least one selected from the group consisting of a fluorine atom and a structure represented by the following formula (A1), the ratio of the number of fluorine atoms to the total number of carbon atoms in the whole molecule is 30% or more, the molecular weight is 500 or more and 4000 or less, and the glass transition temperature is 50°C or more. [Chemical formula] In formula (A1), L 1 represents a linear, branched, or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted with O, S, or a fluorine atom, or a vinylene group which may be substituted with a fluorine atom and may form a ring. In formula (A1), each a independently represents an integer of 0 to 4. In formula (A1), each b independently represents an integer of 1 to 4. In formula (A1), each Rf independently represents a monovalent to divalent substituent having 1 or more carbon atoms and containing 3 or more fluorine atoms. [2] The charging material according to [1] above, wherein the maintenance rate of the surface potential during film formation is 0.7 or more. [3] The charging material according to [1] above, wherein Rf has a structure represented by the following formula (001). [Chemical formula] In formula (001), Rf 001 each independently represents a linear, branched, or cyclic monovalent to divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms and containing 3 or more fluorine atoms, or a vinylene group which may form a ring and contains 3 or more fluorine atoms. L 001 each independently represents a linear, branched, or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted with O, S, or a fluorine atom, or a vinylene group which may be substituted with a fluorine atom and may form a ring. a 001 each independently represents an integer of 0 to 4. a 002 each independently represents an integer of 1 to 4. [4] The charging material according to [1] above, wherein the compound according to [1] above is a compound represented by the following formula (1). [Chemical formula] In formula (1), each R independently represents an optionally substituted monocyclic, fused-ring, or condensed-ring monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, fused-ring, or condensed-ring monovalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted linear, branched, or cyclic monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, an optionally substituted cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or represents a structure represented by the above formula (A1). In formula (1), each X independently represents an optionally substituted monocyclic, fused-ring, or condensed-ring divalent to hexavalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, fused-ring, or condensed-ring divalent to hexavalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted linear, branched, or cyclic divalent to hexavalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, an optionally substituted cyclic divalent to hexavalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, represents O, S, Si, N, or N(R). In formula (1), each L independently represents an optionally substituted monocyclic, fused-ring, or condensed-ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, fused-ring, or condensed-ring divalent to tetravalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted linear, branched, or cyclic divalent to tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, an optionally substituted cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, represents O, S, Si, N, or N(R). In formula (1), each l independently represents an integer of 1 to 3. In formula (1), each m independently represents an integer of 0 to 12. In formula (1), each n independently represents an integer of 1 to 6. In formula (1), each p independently represents an integer from 2 to 6. In formula (1), at least one R has at least one selected from the group consisting of an aromatic ring and a heteroaromatic ring in the molecule, and the ring is substituted with at least one selected from the group consisting of a fluorine atom and the structure represented by the above formula (A1). [5] When X in the above formula (1) is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, the structure represented by the above formula (A1), or substituted with at least one group selected from the group consisting of the above-described groups combined, the charging material according to the above [3]. [6] When L in the above formula (1) is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, the structure represented by the above formula (A1), or substituted with at least one group selected from the group consisting of the above-described groups combined, the charging material according to the above [3] or [4]. [7] When R in the above formula (1) is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups are each independently A linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, A linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, An aromatic hydrocarbon group having 6 to 20 carbon atoms, A heteroaromatic group having 3 to 20 carbon atoms, A cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), Or a charging material according to any one of the above [3] to [5], which is substituted with at least one group selected from the group consisting of groups in which the above-described groups are combined. [8] In the above formula (1), a compound that gives a monocyclic, linked ring, or condensed ring divalent to hexavalent aromatic hydrocarbon group represented by X is, independently of each other, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and at least one selected from the group consisting of those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-described group, A compound that gives a monocyclic, linked ring, or condensed ring divalent to hexavalent heteroaromatic group represented by X is pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and at least one selected from the group consisting of those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-described group, The compound that provides a linear, branched, or cyclic aliphatic hydrocarbon group having 2 to 6 valences represented by X is at least one selected from the group consisting of methane, ethane, adamantane, diamantane, and cyclohexane. The compound that provides a cyclic heteroaliphatic hydrocarbon group having 2 to 6 valences represented by X is at least one selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxane, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane, and the charge-generating material according to any one of [3] to [6] above. [9] In the above formula (1), the compound that provides a monocyclic, linked-ring, or condensed-ring aromatic hydrocarbon group having 2 to 4 valences represented by L is at least one selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-described group. The compound that provides a monocyclic, linked-ring, or condensed-ring heteroaromatic group having 2 to 4 valences represented by L is at least one selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxane, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-described group. The compound that provides a linear, branched, or cyclic divalent to tetravalent aliphatic hydrocarbon group represented by L is at least one selected from the group consisting of methane, ethane, adamantane, diamantane, and cyclohexane. The compound that provides a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by L is at least one selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane. The charge-carrying material according to any one of [3] to [7] above.

[10] In the above formula (1), the compound that provides a monocyclic, linked-ring, or condensed-ring monovalent aromatic hydrocarbon group represented by R is at least one selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned groups. The compound that provides a monocyclic, linked-ring, or condensed-ring monovalent heteroaromatic group represented by R is at least one selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned groups. The compound that provides a linear, branched, or cyclic monovalent aliphatic hydrocarbon group represented by R is at least one selected from the group consisting of methane, ethane, adamantane, diamantane, and cyclohexane. The compound that provides a cyclic monovalent heteroaliphatic hydrocarbon group represented by R is at least one selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxane, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane, and the charge-generating material according to any one of [3] to [8] above.

[11] The charge-generating material according to [1] above, wherein the compound according to [1] above is a compound represented by the following formula (2) or (3).

Chemical formula

Chemical formula

[12] In the above formulas (2) and (3), L 1 When is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups are each independently A linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, A linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, An aromatic hydrocarbon group having 6 to 20 carbon atoms, A heteroaromatic group having 3 to 20 carbon atoms, A cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), or The electrocharging material according to the above

[10] , which is substituted with at least one group selected from the group consisting of a group in which the above-described groups are combined.

[13] In the above formulas (2) and (3), R 1 When is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups are each independently A linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, A linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, An aromatic hydrocarbon group having 6 to 20 carbon atoms, A heteroaromatic group having 3 to 20 carbon atoms, A cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), Or the electrocharging material according to the above

[10] or

[11] , which is substituted with at least one group selected from the group consisting of a group in which the above-described groups are combined.

[14] In the above formulas (2) and (3), L 1A compound that provides a monocyclic, linked ring, or condensed ring divalent to tetravalent aromatic hydrocarbon group represented by is at least one selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned groups. L 1 A compound that provides a monocyclic, linked ring, or condensed ring divalent to tetravalent heteroaromatic group represented by is at least one selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and those in which at least one selected from the group consisting of benzene, naphthalene, and phenanthrene is condensed with the above-mentioned groups. L 1 A compound that provides a linear, branched, or cyclic divalent to tetravalent aliphatic hydrocarbon group represented by is at least one selected from the group consisting of methane, ethane, adamantane, diamantane, and cyclohexane. L 1A compound that provides a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by is at least one selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane, and is the charging material according to any one of the above

[10] to

[12] .

[15] In the above formulas (2) and (3), R 1 A compound that provides a monocyclic, linked ring, or condensed ring monovalent aromatic hydrocarbon group represented by is at least one selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triphenylene, dibenzochrysene, and at least one selected from the group consisting of benzene, naphthalene, and phenanthrene condensed with the above-mentioned groups, and R 1 A compound that provides a monocyclic, linked ring, or condensed ring monovalent heteroaromatic group represented by is at least one selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, and at least one selected from the group consisting of benzene, naphthalene, and phenanthrene condensed with the above-mentioned groups, and R 1A compound that provides a linear, branched, or cyclic monovalent aliphatic hydrocarbon group represented by is at least one selected from the group consisting of methane, ethane, adamantane, diamantane, and cyclohexane, R 1 A compound that provides a cyclic monovalent heteroaliphatic hydrocarbon group represented by is at least one selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane, and the charge-carrying material according to any one of

[10] to

[13] above.

[16] An electret material containing the charge-carrying material according to any one of [1] to

[14] above.

[17] An electret film containing the charge-carrying material according to any one of [1] to

[14] above.

Claims

1. The compound has at least one ring selected from the group consisting of an aromatic ring and a heteroaromatic ring in the molecule, The ring is substituted with at least one selected from the group consisting of a fluorine atom and a structure represented by the following formula (A1): The ratio of the number of fluorine atoms to the number of carbon atoms in the entire molecule is 30% or more, The molecular weight is 500 or more and 4000 or less, and An electrostatically charged material comprising a compound having a glass transition temperature of 50° C. or higher. 【Chemistry 1】 In formula (A1), L １ teeth, a linear, branched or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted with an O, S or fluorine atom, or It represents a divalent vinylene group which may be substituted with a fluorine atom and which may form a ring. In formula (A1), each a independently represents an integer of 0 to 4. In formula (A1), each b independently represents an integer of 1 to 4. In formula (A1), each Rf independently represents a mono- or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms.

2. 2. The electrostatically charged material according to claim 1, wherein the surface potential retention rate during thin film formation is 0.7 or more.

3. The electrostatically charged material according to claim 1 , wherein Rf is a structure represented by the following formula (001): 【Chemistry 2】 In formula (001), Rf ００１ each independently represents a linear, branched or cyclic monovalent or divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms and containing 3 or more fluorine atoms, or It represents a vinylene group which contains three or more fluorine atoms and which may form a ring. L ００１ are each independently a linear, branched or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted with an O, S or fluorine atom, or It represents a divalent vinylene group which may be substituted with a fluorine atom and which may form a ring. a ００１ each independently represents an integer of 0 to 4. a ００２ each independently represents an integer of 1 to 4.

4. 2. The electrostatically charged material according to claim 1, wherein the compound according to claim 1 is a compound represented by the following formula (1): 【Chemistry 3】 In formula (1), each R is independently an optionally substituted monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms and which is a single ring, a linked ring, or a condensed ring; an optionally substituted monovalent heteroaromatic group having 3 to 26 carbon atoms and which is a monocyclic, linked, or condensed ring; an optionally substituted linear, branched or cyclic monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms; an optionally substituted cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a structure represented by the above formula (A1). In formula (1), each X is independently an optionally substituted di- to hexavalent aromatic hydrocarbon group having 6 to 26 carbon atoms and being a monocyclic, linked or fused ring; an optionally substituted di- to hexavalent monocyclic, linked or fused ring heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted linear, branched or cyclic divalent to hexavalent aliphatic hydrocarbon group having 1 to 18 carbon atoms; an optionally substituted cyclic divalent to hexavalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms; represents O, S, Si, N or N(R). In formula (1), each L is independently an optionally substituted di-, tri- or tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms and being a monocyclic, linked or fused ring; an optionally substituted di- to tetravalent monocyclic, linked or fused ring heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted linear, branched or cyclic di- to tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms; an optionally substituted cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms; represents O, S, Si, N or N(R). In formula (1), each 1 independently represents an integer of 1 to 3. In formula (1), each m independently represents an integer of 0 to 12. In formula (1), each n is independently an integer of 1 to 6. In formula (1), each p is independently an integer of 2 to 6. In formula (1), at least one R has at least one ring selected from the group consisting of an aromatic ring and a heteroaromatic ring in the molecule, and the ring is substituted with at least one ring selected from the group consisting of a fluorine atom and a structure represented by formula (A1) above.

5. In the above formula (1), when X is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups each independently represent a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms; a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), or 4. The electrostatically charged material according to claim 3, which is substituted with at least one group selected from the group consisting of combinations of the above groups.

6. In the above formula (1), when L is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups each independently represent a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms; a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), or 5. The electrostatically charged material according to claim 4, which is substituted with at least one group selected from the group consisting of combinations of the above groups.

7. In the above formula (1), when R is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, these groups each independently represent a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms; a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), 5. The electrostatically charged material according to claim 4, which is substituted with at least one group selected from the group consisting of the above groups or a combination of the above groups.

8. In formula (1), the compounds which provide the monocyclic, linked or fused divalent to hexavalent aromatic hydrocarbon group represented by X are each independently at least one selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and the above groups fused with at least one selected from the group consisting of benzene, naphthalene, and phenanthrene; the compound giving the monocyclic, linked or fused divalent to hexavalent heteroaromatic group represented by X is at least one selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and the above groups fused with at least one selected from the group consisting of benzene, naphthalene, and phenanthrene; the compound which gives a linear, branched or cyclic divalent to hexavalent aliphatic hydrocarbon group represented by X is at least one selected from the group consisting of methane, ethane, adamantane, diamantane and cyclohexane; The electrostatically charged material according to claim 4, wherein the compound providing the cyclic divalent to hexavalent heteroaliphatic hydrocarbon group represented by X is at least one selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

9. In the above formula (1), the compound which gives the monocyclic, linked or fused divalent to tetravalent aromatic hydrocarbon group represented by L is at least one selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and the above groups fused with at least one selected from the group consisting of benzene, naphthalene, and phenanthrene, the compound giving the monocyclic, linked, or fused divalent to tetravalent heteroaromatic group represented by L is at least one selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and the above groups fused with at least one selected from the group consisting of benzene, naphthalene, and phenanthrene; the compound which gives a linear, branched or cyclic divalent to tetravalent aliphatic hydrocarbon group represented by L is at least one selected from the group consisting of methane, ethane, adamantane, diamantane and cyclohexane; The electrostatically charged material according to claim 4, wherein the compound providing the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by L is at least one selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

10. In the above formula (1), the compound which provides the monovalent aromatic hydrocarbon group of a single ring, a linked ring, or a condensed ring represented by R is at least one selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and the above groups condensed with at least one selected from the group consisting of benzene, naphthalene, and phenanthrene, the compound providing the monovalent heteroaromatic group of a single ring, a linked ring, or a condensed ring represented by R is at least one selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, and any of the above groups condensed with at least one selected from the group consisting of benzene, naphthalene, and phenanthrene; the compound which provides a linear, branched or cyclic monovalent aliphatic hydrocarbon group represented by R is at least one selected from the group consisting of methane, ethane, adamantane, diamantane and cyclohexane; The electrostatically charged material according to claim 4, wherein the compound providing the cyclic monovalent heteroaliphatic hydrocarbon group represented by R is at least one selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

11. 2. The electrostatically charged material according to claim 1, wherein the compound according to claim 1 is a compound represented by the following formula (2) or (3): 【Chemistry 4】 【Chemistry 5】 In formula (2), each Y is independently an optionally substituted di- to hexavalent aromatic hydrocarbon group having 6 to 26 carbon atoms and being a monocyclic, linked or fused ring; an optionally substituted di- to hexavalent monocyclic, linked or fused ring heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted linear, branched or cyclic divalent to hexavalent aliphatic hydrocarbon group having 1 to 18 carbon atoms; an optionally substituted cyclic divalent to hexavalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms; Represents O, S, or Si. In formula (2) and formula (3), L １ are each independently an optionally substituted di-, tri- or tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms and being a monocyclic, linked or fused ring; an optionally substituted di- to tetravalent monocyclic, linked or fused ring heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted linear, branched or cyclic di- to tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms; an optionally substituted cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms; Represents N or N(R). Each R is independently an optionally substituted monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms and which is a single ring, a linked ring, or a condensed ring; an optionally substituted monovalent heteroaromatic group having 3 to 26 carbon atoms and which is a monocyclic, linked, or condensed ring; an optionally substituted linear, branched or cyclic monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms; an optionally substituted cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a structure represented by the above formula (A1). In formula (2) and formula (3), R １ are each independently an optionally substituted monovalent aromatic hydrocarbon group having 6 to 26 carbon atoms and which is a single ring, a linked ring, or a condensed ring; an optionally substituted monovalent heteroaromatic group having 3 to 26 carbon atoms and which is a monocyclic, linked, or condensed ring; an optionally substituted linear, branched or cyclic monovalent aliphatic hydrocarbon group having 1 to 18 carbon atoms; an optionally substituted cyclic monovalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a structure represented by the above formula (A1). In formula (2) and formula (3), each q independently represents an integer of 0 to 12. In formula (2) and formula (3), each r is independently an integer of 0 to 4. In formula (2) and formula (3), each t is independently an integer of 0 to 4. In formula (2) and formula (3), at least one R １ has at least one ring selected from the group consisting of an aromatic ring and a heteroaromatic ring in the molecule, and the ring is substituted with at least one ring selected from the group consisting of a fluorine atom and a structure represented by the above formula (A1).

12. In the above formulas (2) and (3), L １ is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, each of these groups independently represents a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms; a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), or 12. The electrostatically charged material according to claim 11, which is substituted with at least one group selected from the group consisting of combinations of the above groups.

13. In the above formulas (2) and (3), R １ is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, each of these groups independently represents a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms; a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (A1), The electrostatically charged material according to claim 11, which is substituted with at least one group selected from the group consisting of a combination of the above groups.

14. In the above formulas (2) and (3), L １ is at least one selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and the above groups fused with at least one selected from the group consisting of benzene, naphthalene, and phenanthrene; L １ is at least one selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and the above groups fused with at least one selected from the group consisting of benzene, naphthalene, and phenanthrene, L １ is at least one selected from the group consisting of methane, ethane, adamantane, diamantane, and cyclohexane, L １ The electrostatically charged material according to claim 11, wherein the compound which provides the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I) is at least one selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

15. In the above formulas (2) and (3), R １ is at least one selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and the above groups fused with at least one selected from the group consisting of benzene, naphthalene, and phenanthrene; R １ is at least one selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, and the above groups fused with at least one selected from the group consisting of benzene, naphthalene, and phenanthrene, R １ is at least one compound selected from the group consisting of methane, ethane, adamantane, diamantane, and cyclohexane, R １ The electrostatically charged material according to claim 11, wherein the compound which provides the cyclic monovalent heteroaliphatic hydrocarbon group represented by the formula (I) is at least one selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

16. An electret material comprising the electrically charged material according to claim 1 , claim 4 , or claim 11 .

17. An electret film comprising the electrically charged material according to claim 1 , claim 4 , or claim 11 .

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