Dibenzophosphole oxide derivatives and their preparation method

Abstract

The purpose of the present invention is to provide a novel organophosphorus compound. Provided is a dibenzophosphole oxide derivative represented by the following formula (where R1's are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group). A monomer of a dibenzophosphole oxide derivative containing a polymerizable group is produced, and a polymer thereof is prepared. The polymer has been found to have excellent electrical characteristics.

Description

[Technical field]

[0001] The present disclosure relates to dibenzophosphole oxide derivatives and methods for their preparation. [Background technology]

[0002] Phosphorus compounds are used in a variety of applications due to their properties. Summary of the Invention [Means for solving the problem]

[0003] The present inventors have discovered a novel substance, sodium 5H-benzo[b]phosphindol-5-olate (also referred to as dibenzophosphoroxysodium in this specification). [ka] This compound was found to be useful for preparing a variety of dibenzophosphole oxide derivatives.

[0004] The present inventors have succeeded in preparing a dibenzophosphole oxide derivative monomer containing a polymerizable group and preparing a polymer thereof, which has excellent electrical properties.

[0005] The present disclosure also provides the following: (Item 1) The following formula: [ka] (Here, each R 1are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. A compound represented by the formula: (Item 2) The following formula: [ka] A compound represented by the formula: (Item 3) The following formula: [ka] A method for producing a compound represented by the following formula: [ka] with phenylsodium, Here, each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; method. (Item 4) Each R 1 The method of any one of the preceding items, wherein is hydrogen. (Item 5) The following formula: [ka] A method for preparing a compound having the formula: [ka] and a compound represented by R a X, [ka] , R c -C(=O)-R c with benzoquinone, an inorganic acid or an organic acid, Where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R Z is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkylcarbonyl groups, substituted or unsubstituted alkenylcarbonyl groups, substituted or unsubstituted alkynylcarbonyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; R a is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkylcarbonyl groups, substituted or unsubstituted alkenylcarbonyl groups, substituted or unsubstituted alkynylcarbonyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; X is a halogen; R bis selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; Each R c are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; method. (Item 6) R Z is a substituted or unsubstituted alkenyl group, R a The method of any one of the preceding items, wherein is a substituted or unsubstituted alkenyl group. (Item 7) R Z is a substituted or unsubstituted alkyl group, R b The method of any one of the preceding claims, wherein is a substituted or unsubstituted alkyl group. (Item 8) R Z is a substituted or unsubstituted alkyl group, R c The method of any one of the preceding claims, wherein is hydrogen or a substituted or unsubstituted alkyl group. (Item 9) R Z is hydrogen and the reacting comprises reacting with an inorganic or organic acid. (Item 10) Each R 1 The method of any one of the preceding items, wherein is hydrogen. (Item 11) The following formula: [ka] A method for preparing a compound having the formula: [ka] and a compound represented by the formula: [ka] By reacting with [ka] The method includes the steps of obtaining Where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. (Item 12) Each R 1 The method of any one of the preceding items, wherein is hydrogen. (Item 13) The following formula: [ka] A method for preparing a compound having the formula: [ka] and a compound represented by the formula: [ka] By reacting with [ka] and [ka] is reacted with a base, [ka] obtaining Inclusive of Where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. (Item 14) Each R 1 The method of any one of the preceding items, wherein is hydrogen. (Item 15) The method of any one of the preceding claims, wherein the base is selected from the group consisting of sodium hydroxide, sodium alkoxides, sodium aryloxides, potassium hydroxide, potassium alkoxides, and potassium aryloxides. (Item 16) The following formula: [ka] A method for preparing a compound having the formula: [ka] and a compound represented by R c -C(=O)-R c By reacting with [ka] and [ka] of [ka] React with [ka] obtaining Inclusive of Where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; X is a halogen; Each R c are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R 2 is hydrogen or methyl; method. (Item 17) Each R 1 The method of any one of the preceding items, wherein is hydrogen. (Item 18) The following formula: [ka] A method for preparing a compound having the formula: [ka] and reacting a compound represented by the formula: [ka] and [ka] , R 4 By reacting with -C≡CH, [ka] obtaining Inclusive of Where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R 4 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; method. (Item 19) Each R 1 The method of any one of the preceding items, wherein is hydrogen. (Item 20) The following formula: [ka] (where: Each R 1are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R Z is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkenylcarbonyl group, a substituted or unsubstituted alkynylcarbonyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. A compound having the formula: (Item 21) R Z is a polymerizable group. (Item 22) R Z is a radically polymerizable group. (Item 23) R Z is an allyl group, a substituted allyl group, a styrene group, a substituted styrene group, an acrylic group, a substituted acrylic group, a methacrylic group, or a substituted methacrylic group. (Item 24) The following formula: [ka] A compound selected from the group consisting of: (Item 25) The following formula: [ka] (Here, each R 1are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. A compound. (Item 26) The following formula: [ka] A compound. (Item 27) The following formula: [ka] (Here, each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. A compound. (Item 28) The following formula: [ka] A compound. (Item 29) The following formula: [ka] (Here, each R 1 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; R 2 is hydrogen or methyl) A compound. (Item 30) The following formula: [ka] and R 2 is hydrogen or methyl. (Item 31) The following formula: [ka] (Here, each R 1 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; R 4 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. (Item 32) The following formula: [ka] A compound. (Item 33) The following formula: [ka] (where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R care each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R 2 is hydrogen or methyl) A polymer obtained by polymerizing a monomer having the formula: (Item 34) The following formula: [ka] and a monomer having the formula: [ka] A polymer obtained by copolymerizing Where: Each R 1 , R 1’ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R c , R c’ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R 2 , R 2’ are each independently hydrogen or methyl; polymer. (Item 35) The following formula: [ka] and a compound having a radical polymerizable group A copolymer obtained by copolymerizing Where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R c are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R 2 are each independently hydrogen or methyl; Copolymer. (Item 36) The copolymer according to any one of the preceding items, wherein the compound having a radically polymerizable group is (meth)acrylic acid, a (meth)acrylic acid ester, a (meth)acrylic acid halide, a (meth)acrylic acid salt, styrene or acrylonitrile. (Item 37) An anti-fog agent, a flame retardant, an electric / electronic part, an office automation part, an automobile part, a train part, an aircraft part, a fiber, a sheet, a film, an acrylic glass, a polymerization additive, or a phosphorus providing agent, comprising the compound according to any one of the preceding items, or the polymer or copolymer according to any one of the preceding items. (Item 38) Use of the compound according to any one of the preceding items, or the polymer or copolymer according to any one of the preceding items, as an anti-fog agent, a flame retardant, an electrical / electronic part, an office automation part, an automobile part, an electric train part, an aircraft part, a fiber, a sheet, a film, an acrylic glass, a polymerization additive, or a phosphorus providing agent. (Item 39) A method for producing an anti-fog agent, a flame retardant, an electric / electronic part, an office automation part, an automobile part, a train part, an aircraft part, a fiber, a sheet, a film, an acrylic glass, a polymerization additive, or a phosphorus providing agent by mixing a compound according to any one of the preceding items, or a polymer or copolymer according to any one of the preceding items, with a suitable additive. (Item 40) A method for preventing fogging, a method for making it difficult to burn, a method for use in electrical / electronic parts, a method for use in office automation parts, a method for use in automotive parts, a method for use in railcar parts, a method for use in aircraft parts, a method for use in fibers, a method for use in sheets, a method for use in films, a method for use in acrylic glass, a method for polymerization, or a method for providing phosphorus, comprising a step of using a compound according to any one of the preceding items or a composition comprising a polymer or copolymer according to any one of the preceding items as an anti-fog agent, a flame retardant, an electrical / electronic part, an office automation part, an automobile part, a train part, an aircraft part, a fiber, a sheet, a film, an acrylic glass, a polymerization additive, or a phosphorus providing agent.

[0006] It is contemplated in the present disclosure that one or more of the above features may be provided in combinations in addition to those explicitly stated. Still further embodiments and advantages of the present disclosure will be recognized by those skilled in the art upon reading and understanding the following detailed description, if necessary. Effect of the Invention

[0007] The present invention provides a novel compound that is a dibenzophosphole derivative. This novel compound can be used to prepare various dibenzophosphole oxide derivatives. A monomer of the dibenzophosphole oxide derivative containing a polymerizable group can be prepared, and a polymer can be prepared. This polymer can have unique electrical properties. [Brief description of the drawings]

[0008] [Figure 1] FIG. 1 is a GC-MS spectrum of the product of Example 2. [Diagram 2] FIG. 2 is a GC-MS spectrum of the product of Example 3. [Diagram 3] FIG. 3 is a GC-MS spectrum of the product of Example 4. [Figure 4] FIG. 4 is a GC-MS spectrum of the product of Example 5. [Diagram 5] FIG. 5 is a GC-MS spectrum of the product of Example 6. [Figure 6] FIG. 6 is a GC-MS spectrum of the product of Example 7. [Figure 7] FIG. 7 is a GC-MS spectrum of the product of Example 8. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0009] The present disclosure will be described below while showing the best mode. Throughout this specification, the expression of the singular form should be understood to include the concept of the plural form, unless otherwise specified. Therefore, the singular article (for example, in the case of English, "a", "an", "the", etc.) should be understood to include the concept of the plural form, unless otherwise specified. In addition, it should be understood that the terms used in this specification are used in the sense commonly used in the field, unless otherwise specified. Therefore, unless otherwise defined, all technical terms and scientific and technical terms used in this specification have the same meaning as commonly understood by those skilled in the art to which this invention belongs. In case of conflict, this specification (including definitions) will take precedence.

[0010] (Definition of terms) The terms used in this specification are explained below.

[0011] As used herein, the term "substitution" refers to the replacement of a specific hydrogen atom of an organic compound with another atom or atomic group.

[0012] As used herein, the term "substituent" refers to an atom or functional group that replaces another in a chemical structure.

[0013] In this specification, unless otherwise specified, substitution refers to replacing one or more hydrogen atoms in an organic compound or substituent with another atom or atomic group, or forming a double or triple bond. It is also possible to remove one hydrogen atom and replace it with a monovalent substituent or combine it with a single bond to form a double bond, and it is also possible to remove two hydrogen atoms and replace it with a divalent substituent or combine it with a single bond to form a triple bond.

[0014] In the present disclosure, examples of the substituent include hydrogen, a halogen group, an alkyl group, an alkoxy group, an -OH group, an -NO2 group, an -NH2 group, a -C(=O)H group, an alkylcarbonyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, an alkylcarbonyloxy group, an alkenylcarbonyloxy group, an alkynylcarbonyloxy group, an alkoxycarbonyl group, and an epoxy group. [ka] The substituents may be further substituted, if substitutable.

[0015] In this specification, C1, C2, ..., Cn represent the number of carbon atoms (where n represents any positive integer). Thus, C1 is used to represent a substituent having one carbon atom.

[0016] As used herein, the term "alkyl (group)" refers to a monovalent group formed by removing one hydrogen atom from an aliphatic hydrocarbon (alkane) such as methane, ethane, or propane, and generally has a C n H 2n+1- (where n is a positive integer). The alkyl may be linear or branched. In the present specification, "substituted alkyl (group)" refers to an alkyl in which H of the alkyl is substituted by a substituent as defined above. Specific examples thereof may be C1-C2 alkyl, C1-C3 alkyl, C1-C4 alkyl, C1-C5 alkyl, C1-C6 alkyl, C1-C7 alkyl, C1-C8 alkyl, C1-C9 alkyl, C1-C10 alkyl, C1-C11 alkyl, or C1-C20 alkyl, C1-C2 substituted alkyl, C1-C3 substituted alkyl, C1-C4 substituted alkyl, C1-C5 substituted alkyl, C1-C6 substituted alkyl, C1-C7 substituted alkyl, C1-C8 substituted alkyl, C1-C9 substituted alkyl, C1-C10 substituted alkyl, C1-C11 substituted alkyl, or C1-C20 substituted alkyl. Here, for example, C1-C10 alkyl means a straight-chain or branched alkyl having 1 to 10 carbon atoms, and includes methyl (CH3-), ethyl (C2H5-), n-propyl (CH3CH2CH2-), isopropyl ((CH3)2CH-), n-butyl (CH3CH2CH2CH2-), n-pentyl (CH3CH2CH2CH2CH2-), n-hexyl (CH3CH2CH2CH2CH2CH2-), Examples include n-heptyl (CH3CH2CH2CH2CH2CH2CH2CH2-), n-octyl (CH3CH2CH2CH2CH2CH2CH2CH2CH2-), n-nonyl (CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2-), n-decyl (CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-), -C(CH3)2CH2CH2CH(CH3)2, -CH2CH(CH3)2, etc. Furthermore, for example, C1-C10 substituted alkyl refers to C1-C10 alkyl in which one or more hydrogen atoms are substituted with a substituent.

[0017] An "alkenyl group" means a straight-chain or branched-chain unsaturated hydrocarbon group containing one or more carbon-carbon double bonds, and may have from 2 to 6 carbon atoms. Specific examples of "alkenyl groups" include, but are not limited to, vinyl groups, 1-propylenyl groups, 2-propylenyl groups, 1-butenyl groups, 2-butenyl groups, 3-butenyl groups, 2-methyl-1-propylenyl groups, 2-methyl-2-propylenyl groups, and the like.

[0018] The term "alkynyl group" refers to a straight-chain or branched unsaturated aliphatic hydrocarbon group having one or more triple bonds, and may have 2 to 6 carbon atoms. Specific examples include, but are not limited to, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 1-methyl-2-propynyl group, a 3-butynyl group, a 1-pentynyl group, and a 1-hexynyl group.

[0019] In the present specification, "alicyclic (group)" means a monocyclic or bicyclic non-aromatic hydrocarbon ring, including those having a partially unsaturated bond, a partially bridged structure, a partially spiro-formed structure, and one or two carbonyl structures. The number of carbon atoms may be 3 to 20. "Alicyclic group" includes cycloalkyl groups, cycloalkenyl groups, and cycloalkynyl groups. Specific examples of "alicyclic group" include, but are not limited to, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, cyclohexadinyl groups, cycloheptadinyl groups, cyclooctaadinyl groups, adamantyl groups, norbornyl groups, and the like.

[0020] In this specification, the term "alkoxy (group)" refers to a monovalent group generated by removing a hydrogen atom from a hydroxyl group of an alcohol, and generally represents a C n H 2n+1O- (where n is an integer of 1 or more). The term "substituted alkoxy (group)" refers to an alkoxy in which the H of the alkoxy is substituted with a substituent as defined above. Specific examples may be C1-C2 alkoxy, C1-C3 alkoxy, C1-C4 alkoxy, C1-C5 alkoxy, C1-C6 alkoxy, C1-C7 alkoxy, C1-C8 alkoxy, C1-C9 alkoxy, C1-C10 alkoxy, C1-C11 alkoxy, C1-C20 alkoxy, C1-C2 substituted alkoxy, C1-C3 substituted alkoxy, C1-C4 substituted alkoxy, C1-C5 substituted alkoxy, C1-C6 substituted alkoxy, C1-C7 substituted alkoxy, C1-C8 substituted alkoxy, C1-C9 substituted alkoxy, C1-C10 substituted alkoxy, C1-C11 substituted alkoxy, or C1-C20 substituted alkoxy. Here, for example, C1-C10 alkoxy means straight-chain or branched alkoxy containing 1 to 10 carbon atoms, and examples thereof include methoxy (CH3O-), ethoxy (C2H5O-), and n-propoxy (CH3CH2CH2O-).

[0021] As used herein, an "alkoxycarbonyl (group)" refers to an (alkoxy)C(=O)- group, where alkoxy is as defined above for "alkoxy (group)".

[0022] In this specification, the term "aryl (group)" refers to a group generated by removing one hydrogen atom bonded to an aromatic hydrocarbon ring. Examples of groups that can be obtained include a phenyl group (C6H5-) from benzene, a tolyl group (CH3C6H4-) from toluene, a xylyl group ((CH3)2C6H3-) from xylene, and a naphthyl group (C 10 H8-) is derived. The number of carbon atoms may range from 6 to 12.

[0023] As used herein, the term "heteroaryl (group)" refers to a monocyclic or multicyclic aromatic heterocyclic group containing 1 to 4 identical or different heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur atoms, and may contain 5 to 10 atoms.

[0024] As used herein, the term "non-aryl heterocyclic ring (group)" refers to a monocyclic or bicyclic non-aromatic heterocyclic group containing one or two identical or different heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur atoms, including those having partially unsaturated bonds, those having partially bridged structures and those having partially spiro-bonded structures. It may be composed of 4 to 20 atoms. The non-aryl heterocyclic group may form a condensed ring with an aryl or heteroaryl. For example, C 6-10 The heterocycle also includes the case where the heterocycle is fused with an aryl or a 5- or 6-membered heteroaryl. The non-aryl heterocyclic group may contain one or two carbonyls, thiocarbonyls, sulfinyls, or sulfonyls, and the non-aryl heterocyclic group also includes cyclic groups such as lactams, thiolactams, lactones, thiolactones, cyclic imides, cyclic carbamates, and cyclic thiocarbamates. Specific examples of the "non-aryl heterocyclic group" include, but are not limited to, azetidine, pyrrolidine, piperidine, piperazine, morpholine, homopiperidine, oxetane, tetrahydrofuran, and tetrahydropyran.

[0025] As used herein, the term "halogen (group)" refers to a monovalent group of an element in Group 17 of the periodic table (now referred to as Group 17 in more recent definitions), such as chlorine (Cl), bromine (Br), or iodine (I).

[0026] In this specification, "alkylcarbonyl (group)" refers to a monovalent group formed by removing OH from a carboxylic acid. Representative examples of alkylcarbonyl groups include acetyl (CH3CO-) and C2H5CO-. The number of carbon atoms in the alkyl portion can be 1 to 6, etc. "Substituted alkylcarbonyl (group)" refers to a group in which the hydrogen of an acyl is replaced with a substituent as defined above. "Alkenylcarbonyl (group)" refers to a group in which the alkyl portion of an "alkylcarbonyl (group)" is alkenyl, and "alkynylcarbonyl (group)" refers to a group in which the alkyl portion of an "alkylcarbonyl (group)" is alkynyl.

[0027] In this specification, the term "arylcarbonyl (group)" refers to a monovalent group formed by removing OH from a carboxylic acid. Representative examples of arylcarbonyl groups include phenylcarbonyl (PhCO-) and the like. The term "substituted arylcarbonyl (group)" refers to an aryl group in which the hydrogen atom is replaced with a substituent as defined above.

[0028] In this specification, the term "polymerizable group" refers to any group capable of polymerization, and examples thereof include groups capable of polymerization such as radical polymerization, cationic polymerization, anionic polymerization, coordination polymerization, polycondensation, polyaddition, and addition condensation. In one embodiment, examples of the group capable of radical polymerization (radical polymerizable group) include alkenes having an electron donating group, such as vinyl groups, cyclic ether groups (groups based on epoxide, oxetane, tetrahydrofuran, etc.), cyclic acetals (groups based on 1,3-dioxolane, etc.), and lactones (groups based on β-propiolactone, etc.). Examples of the group capable of anion polymerization (anion polymerizable group) include alkenes having an electron withdrawing group, such as groups based on styrene, acrylonitrile, nitroethylene, and cyanoacrylate. Groups capable of coordination polymerization (coordination polymerizable groups) are groups that can be polymerized by coordinating to a catalyst such as a Ziegler-Natta catalyst, and include groups based on ethylene, propylene, butadiene, isoprene, acetylene, etc. Groups capable of polycondensation (polycondensable groups) include groups that give polyamides, polyesters, and polycarbonates. Groups capable of polyaddition (polyaddition capable groups) include groups that give polyurethanes and epoxy resins. Groups capable of addition condensation (addition condensable groups) include groups that give phenolic resins, urea resins, and melamine resins.

[0029] In this specification, the term "radical polymerizable group" refers to any group that polymerizes by a radical reaction. Representative examples include, but are not limited to, groups having an unsaturated double bond at the end of a substituent. Examples of such radical polymerizable groups include, but are not limited to, allyl groups, substituted allyl groups, styrene groups, substituted styrene groups, acrylic groups, substituted acrylic groups, methacrylic groups, and substituted methacrylic groups.

[0030] As used herein, the term "styrene group" refers to a monovalent group resulting from the loss of a hydrogen atom from styrene, and the hydrogen atom lost may be on the phenyl ring or in the ethylene moiety.

[0031] As used herein, an "acrylic group" refers to a CH2=CH2-C(O)-O- group.

[0032] As used herein, a "methacrylic group" refers to a CH2=CH(CH3)-C(O)-O- group.

[0033] In this specification, the term "polymer" is also referred to as a polymer, and is a substance that is made up of molecules in which one or several types of atoms or atomic groups are structural units, and these are repeatedly linked together in large numbers, and the number of repetitions of the structural units of the molecule is very large, so that a certain physical property of the substance does not change with an increase or decrease in one or several structural units. Examples of polymers include homopolymers and copolymers.

[0034] In this specification, the term "monomer" refers to a compound that can become a structural unit of the basic structure of a polymer through a polymerization reaction. In some cases, one type of monomer can produce multiple types of structural units. In addition, the monomer of the present disclosure can be bonded to other substances through radical polymerization.

[0035] As used herein, the term "homopolymer" is also referred to as a single polymer, and refers to a polymer obtained by polymerization using a single monomer.

[0036] In this specification, the term "copolymer" is also referred to as a copolymer, and refers to a polymer obtained by polymerization using a plurality of monomers. In a representative embodiment of the present disclosure, the polymer may be formed by copolymerization with a monomer different from the monomer of the present disclosure. The monomer different from the monomer of the present disclosure may include (meth)acrylic acid, (meth)acrylic acid esters (e.g., methyl (meth)acrylate), (meth)acrylic acid halides, (meth)acrylic acid salts, styrene, or acrylonitrile.

[0037] As used herein, the term "polymerization" refers to a reaction in which a high molecular compound (polymer) is produced from a low molecular compound (monomer).

[0038] As used herein, "(meth)acrylic acid" refers to acrylic acid and / or methacrylic acid.

[0039] In this specification, the term "acid halide" refers to a compound in which the OH group in the carboxyl group of a carboxylic acid is replaced with a halogen. Depending on the type of halogen, there are four types: acid fluoride, acid chloride, acid bromide, and acid iodide.

[0040] As used herein, the term "base" refers to a substance that accepts protons according to the Bronsted-Lowry definition. Examples of bases include sodium hydroxide, sodium alkoxides, sodium aryloxides, potassium hydroxide, potassium alkoxides, and potassium aryloxides.

[0041] As used herein, "alkali metal" refers to lithium, sodium, potassium, rubidium, cesium and francium.

[0042] As used herein, "(meth)acrylic acid" refers to acrylic acid, methacrylic acid, or both.

[0043] As used herein, the term "additive" refers to a substance that is added to any substance.

[0044] As used herein, "anti-fog agent" refers to a substance that preserves the transparency of a material (eg, polyacrylic acid), typically by making the surface of the material more hydrophobic.

[0045] In this specification, the term "phosphorus imparting agent" refers to a substance that imparts a phosphorus component to a certain substance, and is typically achieved by bonding a group containing phosphorus to a certain substance. A phosphorus imparting agent having a (meth)acrylic group can bond a group containing phosphorus to a compound having a radically polymerizable group by radical polymerization. The phosphorus imparting agent can be used, for example, in the manufacture of fertilizers, agricultural chemicals, medicines, insecticides, explosives, electronic materials, catalysts, flame retardants, metal surface treatment agents, detergents, antifreeze solutions, surfactants, defoamers, and lubricants.

[0046] The compounds of the present disclosure include salts. For example, salts with alkali metals (such as lithium, sodium or potassium), alkaline earth metals (such as calcium), magnesium, transition metals (such as zinc and iron), ammonium, organic bases and amino acids, or salts with inorganic acids (such as hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, phosphoric acid or hydroiodic acid), and organic acids (such as acetic acid, trifluoroacetic acid, citric acid, lactic acid, tartaric acid, oxalic acid, maleic acid, fumaric acid, mandelic acid, glutaric acid, malic acid, benzoic acid, phthalic acid, benzenesulfonic acid, p-toluenesulfonic acid, methanesulfonic acid or ethanesulfonic acid). These salts can be formed by conventional methods.

[0047] The compounds of the present disclosure are not limited to any particular isomer, but include all possible isomers (such as keto-enol isomers, imine-enamine isomers, diastereoisomers, optical isomers and rotamers) and racemates.

[0048] One or more hydrogen, carbon or other atoms of the compounds of the present disclosure may be replaced with an isotope of the hydrogen, carbon or other atom. The compounds of the present disclosure include all radiolabeled forms of the compounds of the present disclosure. Examples of isotopes that may be incorporated into the compounds of the present disclosure include, but are not limited to,2 H, 3 H, 11 C. 13 C. 14 C. 15 N, 18 O. 17 O. 31 P, 32 P, 35 S, 18 F, 123 I and 36 Like Cl, it includes hydrogen, carbon, nitrogen, oxygen, phosphorus, sulfur, fluorine, iodine and chlorine.

[0049] Description of the Preferred Embodiments The preferred embodiments of the present disclosure are described below. The embodiments provided below are provided for a better understanding of the present disclosure, and it is understood that the scope of the present disclosure should not be limited to the following description. Therefore, it is clear that a person skilled in the art can make appropriate modifications within the scope of the present disclosure in light of the description in this specification. It is also understood that the following embodiments of the present disclosure can be used alone or in combination.

[0050] In the present disclosure, [ka] (Here, each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. The compound is provided:

[0051] In the present disclosure, [ka] The compound is provided:

[0052] In the present disclosure, [ka] A method for producing a compound represented by the following formula: [ka] with phenylsodium, Here, each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0053] In the above method, each R 1 is hydrogen.

[0054] In the above method, examples of the solvent include chloroform, dichloromethane, 1,2-dichloroethane (EDC), acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, dimethylacetamide, and ethyl acetate.

[0055] In the present disclosure, [ka] A method for preparing a compound having the formula: [ka] and a compound represented by R a X, [ka] , R c -C(=O)-R c with benzoquinone, an inorganic acid or an organic acid, Where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R Z is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkylcarbonyl groups, substituted or unsubstituted alkenylcarbonyl groups, substituted or unsubstituted alkynylcarbonyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; R a is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkylcarbonyl groups, substituted or unsubstituted alkenylcarbonyl groups, substituted or unsubstituted alkynylcarbonyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; X is a halogen; R b is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; Each R care each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0056] In the above method, R Z is a substituted or unsubstituted alkyl group, R a is a substituted or unsubstituted alkyl group. For example, R a is n-butyl.

[0057] In the above method, R Z is a substituted or unsubstituted alkenyl group, R a is a substituted or unsubstituted alkenyl group. For example, R a is an allyl.

[0058] In the above method, R Z is a substituted or unsubstituted alkyl group, R b is a substituted or unsubstituted alkyl group. For example, R b is propylene oxide.

[0059] In the above method, R Z is a substituted or unsubstituted alkyl group, R c is hydrogen or a substituted or unsubstituted alkyl group. For example, R c is hydrogen, -Cl, or methyl. c is hydrogen, R c -C(=O)-R c is formaldehyde, which is paraformaldehyde (CHO) n (n is any integer).

[0060] In the above method, R Z is hydrogen and the reaction includes reacting with an inorganic or organic acid.

[0061] In the above method, each R 1 is hydrogen.

[0062] In the above method, examples of the solvent include chloroform, dichloromethane, 1,2-dichloroethane (EDC), acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, dimethylacetamide, and ethyl acetate.

[0063] In the above process, the reaction temperature is room temperature.

[0064] In the present disclosure, [ka] A method for preparing a compound having the formula: [ka] and a compound represented by the formula: [ka] By reacting with [ka] The method includes the steps of obtaining Where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0065] In the above method, each R 1is hydrogen.

[0066] In the present disclosure, [ka] A method for preparing a compound having the formula: [ka] and a compound represented by the formula: [ka] By reacting with [ka] and [ka] is reacted with a base, [ka] obtaining Inclusive of Where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0067] In the above method, each R 1 is hydrogen.

[0068] In the above process, the base is selected from the group consisting of sodium hydroxide, sodium alkoxide, sodium aryloxide, potassium hydroxide, potassium alkoxide, and potassium aryloxide.

[0069] In the present disclosure, [ka] A method for preparing a compound having the formula: [ka] and a compound represented by R c -C(=O)-R c By reacting with [ka] and [ka] of [ka] React with [ka] obtaining Inclusive of Where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; X is a halogen; Each R c are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R 2 is hydrogen or methyl.

[0070] In the above method, each R 1 is hydrogen.

[0071] In the present disclosure, [ka] A method for preparing a compound having the formula: [ka] and reacting a compound represented by the formula: [ka] and [ka] , R 4 By reacting with -C≡CH, [ka] obtaining Inclusive of Where: Each R 1are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R 4 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0072] In the above method, each R 1 is hydrogen.

[0073] In the present disclosure, [ka] (where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R Z is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted alkenylcarbonyl group, a substituted or unsubstituted alkynylcarbonyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. Compounds having the formula:

[0074] In the above formula, R Z is a polymerizable moiety.

[0075] In the above formula, R Zis a radically polymerizable group.

[0076] In the above formula, R Z is an allyl group, a substituted allyl group, a styrene group, a substituted styrene group, an acrylic group, a substituted acrylic group, a methacrylic group, or a substituted methacrylic group.

[0077] In the present disclosure, [ka] A compound is provided, the compound being selected from the group consisting of:

[0078] In the present disclosure, [ka] (Here, each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. The compound is provided,

[0079] In the present disclosure, [ka] The compound is provided,

[0080] In the present disclosure, [ka] (Here, each R 1are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. The compound is provided,

[0081] In the present disclosure, [ka] The compound is provided,

[0082] In the present disclosure, [ka] (Here, each R 1 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; R 2 is hydrogen or methyl) The compound is provided,

[0083] In the present disclosure, [ka] and R 2 is hydrogen or methyl.

[0084] In the present disclosure, [ka] (Here, each R 1are each independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; R 4 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

[0085] In the present disclosure, [ka] The compound is provided,

[0086] In the present disclosure, [ka] (where: Each R 1 are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R c are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R 2 is hydrogen or methyl) The polymer is obtained by polymerizing a monomer having the formula:

[0087] In the present disclosure, [ka] and a monomer having the formula: [ka] A polymer obtained by copolymerizing Where: Each R 1 , R 1’ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R c , R c’ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R 2 , R 2’ are each independently hydrogen or methyl; A polymer is provided.

[0088] In the present disclosure, [ka] and a compound having a radical polymerizable group A copolymer obtained by copolymerizing Where: Each R 1are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R c are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R 2 are each independently hydrogen or methyl.

[0089] In the above copolymer, the compound having a radically polymerizable group is (meth)acrylic acid, a (meth)acrylic acid ester, a (meth)acrylic acid halide, a (meth)acrylate, styrene or acrylonitrile.

[0090] The copolymers of the present disclosure may have unique dielectric constants. By including the monomers of the present disclosure, it is possible to adjust the dielectric constant of the corresponding diphenyl homopolymer. In one embodiment, the dielectric constant may be reduced (insulating properties improved) compared to the corresponding diphenyl homopolymer.

[0091] In the present disclosure, there is provided an anti-fogging agent, a flame retardant, an electric / electronic part, an office automation part, an automobile part, an electric train part, an aircraft part, a fiber, a sheet, a film, an acrylic glass, a polymerization additive, or a phosphorus providing agent, which comprises the above polymer.

[0092] (Preparation of five-membered ring intermediate) The present disclosure provides a method for producing a five-membered ring intermediate dibenzophospholeoxysodium derivative from a triphenylphosphine oxide derivative. [ka] (R 1 is as described in the specification). 1 ) 5 groups removed, 2 R 1 It is believed that elimination of a group and bonding of the two phenyl groups occurs to produce a five-membered ring intermediate dibenzophosphoroxysodium derivative.

[0093] (Reaction with various electrophiles) The five-membered ring intermediate dibenzophospholeoxy sodium derivatives of the present disclosure react with a variety of electrophiles to give a variety of dibenzophosphole oxide derivatives. [ka] (Nu is an electrophile, R 1 , R Z are as described in the specification.)

[0094] For example, the following compound can be synthesized by reaction with butyl bromide, acetyl chloride, propylene oxide, and paraformaldehyde: [ka]

[0095] (Synthesis of Monomer) The present disclosure provides a method for preparing monomers having various five-membered ring intermediate structures using the five-membered ring intermediate dibenzophosphoroxy sodium derivatives of the present disclosure. For example, the monomers can be synthesized as follows: [ka] [ka]

[0096] (Preparation of Polymer) The present disclosure can prepare a polymer from the above monomer. The polymerization can be homopolymerization or copolymerization. The polymerization can be carried out by radical polymerization. As the polymerization initiator, azo compound-based thermal polymerization initiators include azoisobutyronitrile (AIBN), azobisdimethylvaleronitrile (ADVN), azobismethylbutyronitrile (AMBN), etc., and organic peroxide-based thermal polymerization initiators include benzoyl peroxide (dibenzoyl peroxide) (BPO), t-butyl hydroperoxide (TBHP), cumene hydroperoxide, di-t-butyl hydroperoxide, etc.

[0097] (Properties of polymer) Because the polymers of the present disclosure contain phosphorus and aromatic rings, they may have unique electrical properties and glass transition temperatures.

[0098] (Application) The organic phosphorus compounds of the present disclosure are useful as raw materials for making other organic phosphorus compounds. The organic phosphorus compounds of the present disclosure are also useful as raw materials for forming metal complexes. The organic phosphorus compounds of the present disclosure can also be used as anti-fog agents, flame retardants, electrical / electronic parts, OA-related parts, automobile parts, train parts, aircraft parts, or fibers, sheets, films, or acrylic glass, polymerization additives, surface modifiers, etc. Furthermore, they can also be used as materials for lithium-ion secondary batteries, metal extractants, wastewater treatment agents, etc.

[0099] The compound, homopolymer or copolymer of the present disclosure contains phosphorus and can be useful as a flame retardant.When the compound or its salt of the present disclosure is solid (e.g., powder), it is easy to handle and can be used in appropriate amounts.It can be less wasteful than when it is liquid.

[0100] The homopolymers or copolymers of the present disclosure are flame retardant and are useful in electrical / electronic parts, office automation parts, automobile parts, train parts, aircraft parts, fibers, and the like.

[0101] The compound having a polymerizable group of the present disclosure can be polymerized, and can be used as a polymerization additive to change the properties of the polymer produced.When the compound or its salt of the present disclosure is solid (e.g., powder), it is easy to handle and can be used in an appropriate amount.It can be less wasteful than when it is liquid.

[0102] The compound of the present disclosure can be bonded to the surface of an object, and can change the properties of the surface as a surface modifier.When the compound of the present disclosure is solid (e.g., powder), it is easy to handle and can be used in an appropriate amount.It can be less wasteful than when it is liquid.

[0103] In one aspect, the present disclosure provides a phosphorus donor comprising the compound of the present disclosure.The phosphorus donor of the present disclosure can be used in the manufacture of fertilizer, pesticide, medicine, insecticide, explosives, electronic materials, catalyst, flame retardant, metal surface treatment agent, detergent, antifreeze, surfactant, defoamer, lubricant, etc.When the compound of the present disclosure is solid (e.g., powder), it is easy to handle and can be easily used in an appropriate amount.It can be less wasteful than when it is liquid.

[0104] The compound of the present disclosure that includes a (meth)acrylic acid moiety that can easily undergo radical polymerization can easily add phosphorus to other substances. The object to which phosphorus is added may be anything that can react with the radical generated in the (meth)acrylic acid moiety. When the compound of the present disclosure or its salt is a solid (e.g., powder), it is easy to handle and can be used in an appropriate amount. It can be less wasteful than when it is a liquid.

[0105] In one aspect, the present disclosure provides a surface treatment method using the compound of the present disclosure. This surface treatment method can reduce the water absorption of the surface. The method can include polymerizing the compound of the present disclosure on the surface. The surface can be resin or glass. When the compound of the present disclosure is solid (e.g., powder), it is easy to handle and can be easily used in an appropriate amount. It can be less wasteful than when it is liquid.

[0106] All references cited herein, including scientific literature, patents, patent applications, and the like, are hereby incorporated by reference in their entirety to the same extent as if each was specifically set forth.

[0107] The present invention has been described above by showing preferred embodiments for ease of understanding. The present invention will be described below based on examples, but the above description and the following examples are provided for illustrative purposes only and are not provided for the purpose of limiting the present invention. Therefore, the scope of the present invention is not limited to the embodiments or examples specifically described in this specification, but is limited only by the scope of the claims. EXAMPLES

[0108] The present invention will be described in more detail with reference to the following examples and comparative examples. However, the present invention is not limited to these examples. Examples obtained by appropriately combining the technical means disclosed in each example are also included in the scope of the present invention.

[0109] Furthermore, the abbreviations used in this specification have the following meanings. GC-MS: Gas chromatograph mass spectrometer NMR: nuclear magnetic resonance Ph: Phenyl group rt: room temperature (for example, 15°C to 25°C) THF: tetrahydrofuran

[0110] The compounds of the present disclosure and their synthesis are further illustrated by the following examples. In certain instances, common names are used and it is understood that these common names will be recognized by those of skill in the art.

[0111] measuring equipment The GC, GC-MS, and NMR used in the following experiments were all performed using the following equipment. Varian 220-MS Column used: Agilent Technologies DB-5 NMR JEOL JNM-ECX FT NMR or JEOL JNM-ECS FT NMR

[0112] Reagents used Triphenylphosphine oxide Triphenylphosphine oxide manufactured by Hokko Chemical Co., Ltd. was used. Epichlorohydrin The product used was manufactured by Osaka Soda Co., Ltd. MC-4 MC-4 manufactured by Katayama Chemical Industry Co., Ltd. was used. Other general-purpose reagents and solvents used were those manufactured by Sigma-Aldrich Japan.

[0113] (Example 1) Preparation of Five-Membered Ring Intermediate A [ka] Triphenylphosphine oxide (5.0 mmol in THF) was added to phenylsodium (6.2 mmol), and the mixture was stirred at room temperature for 20 hours. 31 The production of the target product (intermediate A) was confirmed by P NMR. 31 P NMR(NONE, 161 MHz)=δ101.8.

[0114] Reactions with various electrophiles Example 2 Butyl bromide Butyl bromide (2 mmol) was placed in a 20 mL Schlenk flask and intermediate A (1 After stirring at room temperature for 1 hour, the mixture was quenched with saturated aqueous ammonium chloride solution (3 mL). Ethyl acetate (4 mL) was added to extract the organic matter, and the results were analyzed by GC-MS. 31 P NMR measurements were carried out.

[0115] [ka] GC-MS:257[M+1], 214, 199, 165, 152, 126, 86, 47 31 P NMR (NONE, 161 MHz) = δ 39.4. The GC-MS spectrum is shown in Figure 1.

[0116] (Example 3) Acetyl chloride Acetyl chloride (2 mmol) was placed in a 20 mL Schlenk flask and cooled on ice, and intermediate A (1 mmol) was added under a nitrogen stream. After warming to room temperature and stirring for 1 hour, the mixture was quenched with a saturated aqueous ammonium chloride solution (3 mL). Ethyl acetate (4 mL) was added to extract the organic matter, and GC-MS measurements were performed.

[0117] [ka] GC-MS: 242[M], 200, 199, 152, 43. The GC-MS spectrum is shown in Figure 2.

[0118] (Example 4) Propylene oxide Propylene oxide (2 mmol) was placed in a 20 mL Schlenk flask, and intermediate A (1 mmol) was added under a nitrogen stream. After stirring at room temperature for 1 hour, the mixture was quenched with a saturated aqueous ammonium chloride solution (3 mL). Ethyl acetate (4 mL) was added to extract the organic matter, and the mixture was analyzed by GC-MS. 31 P NMR measurements were performed.

[0119] [ka] 31 P NMR (NONE, 161MHz) = δ 41.7 GC-MS: 259[M+1], 241, 214, 199, 152, 107, 47. The GC-MS spectrum is shown in Figure 3.

[0120] (Example 5) Formaldehyde Paraformaldehyde (2 mmol) was placed in a 20 mL Schlenk flask, and intermediate A (1 mmol) was added under a nitrogen stream. After stirring at room temperature for 1 hour, the mixture was quenched with a saturated aqueous ammonium chloride solution (3 mL). Ethyl acetate (4 mL) was added to extract the organic matter, and GC-MS measurements were performed.

[0121] [ka] GC-MS: 230[M], 211, 168, 136, 97, 56. The GC-MS spectrum is shown in Figure 4.

[0122] Monomer synthesis (Example 6) Allyl group Allyl bromide (2 mmol) was placed in a 20 mL Schlenk flask, and intermediate A (1 mmol) was added under a nitrogen stream. After stirring at room temperature for 1 hour, the mixture was quenched with a saturated aqueous ammonium chloride solution (3 mL). Ethyl acetate (4 mL) was added to extract the organic matter, and GC-MS measurements were performed.

[0123] [ka] GC-MS: 240[M], 199, 152, 98, 47. The GC-MS spectrum is shown in Figure 5.

[0124] (Example 7) Epoxy group Epichlorohydrin (10 mmol) was placed in a 20 mL Schlenk flask, and intermediate A (1 mmol) was added under a nitrogen stream. After stirring at room temperature for 1 hour, the mixture was quenched with water (3 mL). Toluene (4 mL) was added to extract the organic matter. The suspended toluene layer was removed, and acetone was added to homogenize it, followed by GC-MS measurement.

[0125] [ka] GC-MS: 256[M], 227, 200, 199, 152, 77, 47. The GC-MS spectrum is shown in Figure 6.

[0126] (Example 8) Methacrylic group 50 mg of the reaction mixture obtained in Example 5 was dissolved in toluene (3 mL). Triethylamine (1 mL) and methacrylic acid chloride (1 mL) were added to the solution, and the mixture was stirred at room temperature for 1 hour. The reaction solution was separated into ethyl acetate / aqueous sodium hydroxide solution (1M), and the organic layer was concentrated. The product was dissolved in ethyl acetate and subjected to GC-MS measurement, and it was confirmed that the target methacrylic compound (MC-6) was produced.

[0127] [ka] GC-MS: 298[M], 268, 240, 200, 199, 153, 152, 87, 69, 41. The GC-MS spectrum is shown in Figure 7. In this reaction, the diphenyl form (MC-4) was contained as a by-product.

[0128] [ka]

[0129] The following polymers were prepared:

[0130] (Comparative Example 1) MC-4 Polymer 20.0 g of MC-4 was weighed into a 200 mL separable flask, and 4 times the weight of 2-butanone was added and thoroughly stirred. After degassing and nitrogen replacement, the mixture was heated to 40°C. After adding 0.22 g of benzoyl peroxide, the temperature inside the reaction vessel was raised to 80°C and reacted for 20 hours. After the reaction was completed, the reaction solution was dropped into hexane to precipitate the produced polymer. The precipitated polymer was washed with ion-exchanged water. The polymer was dried in a vacuum dryer. The weight average molecular weight and dielectric constant of the obtained polymer were measured. [ka]

[0131] (Example 9) Copolymer of new monomer (MC-6) + MC-4 A mixture (20.0 g) of the new monomer (MC-6) and MC-4 obtained by the method of Example 8 was weighed into a 200 mL separable flask, and 4 times the weight of 2-butanone was added and thoroughly stirred. Here, the ratio of MC-6 to MC-4 in this mixture was determined by GC and 31 From the P NMR measurement, it was 50% each. After degassing and nitrogen replacement, it was heated to 40°C. After adding 0.22g of benzoyl peroxide, the temperature in the reaction vessel was raised to 80°C and reacted for 20 hours. After the reaction was completed, the reaction solution was dropped into hexane to precipitate the produced polymer. The precipitated polymer was washed with ion-exchanged water. The polymer was dried in a vacuum dryer. The weight average molecular weight and dielectric constant of the obtained polymer were measured. [ka]

[0132] The polymer evaluation results are summarized below. [Table 1] The equipment used is as follows: GPC Tosoh HLC-8320GPC column: TSK gel Super AW2500 6.0×150 Dielectric constant Toyo Corporation Dielectric constant measurement system WKR6510P Measurement frequency: 1MHz Measurement temperature: 25°C

[0133] It has been shown that when the monomer (MC-6) of the present disclosure is included, the dielectric constant is lower (insulating properties are improved) than the corresponding diphenyl homopolymer.

[0134] As described above, the present invention has been illustrated using preferred embodiments of the present invention, but it is understood that the scope of the present invention should be interpreted only by the claims. This application claims priority to Japanese Patent Application No. 2019-141226 (filed July 31, 2019), the contents of which are incorporated herein by reference in their entirety. It is understood that the patents, patent applications and other documents cited in this specification should be incorporated by reference to this specification in the same manner as if the contents themselves were specifically described herein. It is understood that the patents, patent applications and other documents cited in this specification should be incorporated by reference to this specification in the same manner as if the contents themselves were specifically described herein. [Industrial Applicability]

[0135] To provide a novel organophosphorus compound. To provide a novel organophosphorus compound containing a polymerizable group, and to provide novel homopolymers and copolymers. To provide homopolymers and copolymers having excellent electrical properties.

Claims

1. The following formula: 【Chemistry 1】 (Here, each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. A compound represented by the formula:

2. The following formula: 【Chemistry 2】 A compound represented by the formula:

3. The following formula: 【Chemistry 3】 A method for producing a compound represented by the following formula: 【Chemistry 4】 with phenylsodium, Here, each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; method.

4. Each R １ The method of claim 3 , wherein is hydrogen.

5. The following formula: 【Chemistry 5】 A method for preparing a compound having the formula: 【Chemistry 6】 and a compound represented by R ａ X, 【Chemistry 7】 , R ｃ -C(=O)-R ｃ with benzoquinone, an inorganic acid or an organic acid, Where: Each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R Ｚ is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkylcarbonyl groups, substituted or unsubstituted alkenylcarbonyl groups, substituted or unsubstituted alkynylcarbonyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; R ａ is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alkylcarbonyl groups, substituted or unsubstituted alkenylcarbonyl groups, substituted or unsubstituted alkynylcarbonyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; X is a halogen; R ｂ is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted alicyclic groups, substituted or unsubstituted non-aryl heterocyclic groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups; Each R ｃ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; method.

6. R Ｚ is a substituted or unsubstituted alkenyl group, R ａ The method of claim 5 , wherein is a substituted or unsubstituted alkenyl group.

7. R Ｚ is a substituted or unsubstituted alkyl group, R ｂ The method of claim 5 , wherein is a substituted or unsubstituted alkyl group.

8. R Ｚ is a substituted or unsubstituted alkyl group, R ｃ The method of claim 5 , wherein is hydrogen or a substituted or unsubstituted alkyl group.

9. R Ｚ The method of claim 5 , wherein is hydrogen and the reacting comprises reacting with an inorganic or organic acid.

10. Each R １ The method of any one of claims 5 to 9, wherein is hydrogen.

11. The following formula: 【Chemistry 8】 A method for preparing a compound having the formula: 【Chemistry 9】 and a compound represented by the formula: 【Chemistry 10】 By reacting with 【Chemistry 11】 The method includes the steps of obtaining Where: Each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

12. Each R １ The method of claim 11 , wherein is hydrogen.

13. The following formula: 【Chemistry 12】 A method for preparing a compound having the formula: 【Chemistry 13】 and a compound represented by the formula: 【Chemistry 14】 By reacting with 【Chemistry 15】 and 【Chemistry 16】 is reacted with a base, 【Chemistry 17】 obtaining Inclusive of Where: Each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

14. Each R １ The method of claim 13 , wherein is hydrogen.

15. 15. The method of claim 13 or 14, wherein the base is selected from the group consisting of sodium hydroxide, sodium alkoxides, sodium aryloxides, potassium hydroxide, potassium alkoxides, and potassium aryloxides.

16. The following formula: 【Chemistry 18】 A method for preparing a compound having the formula: 【Chemistry 19】 and a compound represented by R ｃ -C(=O)-R ｃ By reacting with 【Chemistry 20】 and 【Chemistry 21】 of 【Chemical 22】 React with 【Chemistry 23】 obtaining Inclusive of Where: Each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; X is a halogen; Each R ｃ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R ２ is hydrogen or methyl; method.

17. Each R １ The method of claim 16 , wherein is hydrogen.

18. The following formula: 【Chemistry 24】 A method for preparing a compound having the formula: 【Chemistry 25】 and reacting a compound represented by the formula: 【Chemistry 26】 and 【Chemical 27】 , R ４ By reacting with -C≡CH, 【Chemistry 28】 obtaining Inclusive of Where: Each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R ４ is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; method.

19. Each R １ The method of claim 18 , wherein is hydrogen.

20. The following formula: 【Chemistry 30】 A compound selected from the group consisting of:

21. The following formula: 【Chemical 33】 (Here, each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. A compound.

22. The following formula: 【Chemical 34】 A compound.

23. The following formula: 【Chemistry 35】 (Here, each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R ２ is hydrogen or methyl, and each R C is independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group. A compound.

24. The following formula: 【Chemical 36】 and R ２ is hydrogen or methyl.

25. The following formula: 【Chemical 37】 (wherein R 1 is hydrogen and R ４ is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

26. The following formula: 【Chemical 38】 A compound.

27. The following formula: 【Chemical 39】 (where: Each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R ｃ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R ２ is hydrogen or methyl) A polymer obtained by polymerizing a monomer having the formula:

28. The following formula: 【Chemistry 40】 and a monomer having the formula: 【Chemistry 41】 A polymer obtained by copolymerizing Where: Each R １ , R １’ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R ｃ , R ｃ’ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; R ２ , R ２’ are each independently hydrogen or methyl; polymer.

29. The following formula: 【Chemistry 42】 and a compound having a radical polymerizable group A copolymer obtained by copolymerizing Where: Each R １ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R ｃ are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic group, a substituted or unsubstituted non-aryl heterocyclic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group; Each R ２ are each independently hydrogen or methyl; Copolymer.

30. 30. The copolymer of claim 29, wherein the compound having a radically polymerizable group is (meth)acrylic acid, a (meth)acrylic acid ester, a (meth)acrylic acid halide, a (meth)acrylate, styrene or acrylonitrile.

31. An anti-fog agent, a flame retardant, an electric / electronic part, an office automation part, an automobile part, a train part, an aircraft part, a fiber, a sheet, a film, an acrylic glass, a polymerization additive, or a phosphorus providing agent, comprising the compound according to any one of claims 20 to 26, or the polymer according to claim 27 or 28.

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