Diarylphosphine oxide derivative

Abstract

The present invention provides a novel phosphorus compound, specifically a phosphine oxide compound represented by the general formula Ra-P(=O)R1R2 or a salt of the phosphine oxide compound. In the formula, R1 and R2 are the same or different and each independently represent a substituted aryl group, and Ra is a group having an unsaturated double bond, an epoxidized group, a hydroxylated group, or a phosphorus-containing group. The aryl groups of R1 and R2 each have one to three substituents.

Description

Technical Field

[0001] The present disclosure relates to diarylphosphine oxide derivatives.

Background Art

[0002] Phosphorus compounds are used in various applications due to their properties. It is meaningful to provide novel phosphorus-containing compounds.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Summary of the Invention

Means for Solving the Problems

[0004] As a result of intensive studies, the inventors have synthesized a novel compound of a diarylphosphine oxide derivative considered to be highly useful and provided the present disclosure.

[0005] The present disclosure provides a method for synthesizing a diarylphosphine oxide derivative, which has been considered particularly difficult in the past.

[0006] The present disclosure also provides the following items. (Item 1) The following general formula R a -P(=O)R 1 R 2 represents a phosphine oxide compound or a salt thereof, wherein, R 1 and R 2 are different or the same and are each independently an aryl group having a substituent, Ra is a group having an unsaturated double bond, a group having an epoxy group, a group containing a hydroxy group, or a group containing phosphorus, a phosphine oxide compound or a salt thereof. (Item 2) R 1 and R 2 The phosphine oxide compound or a salt thereof according to Item 1, wherein the aryl groups in are each independently have one, two or three substituents. (Item 3) R 1 and R 2 The phosphine oxide compound or a salt thereof according to Item 1, wherein the aryl groups in each have one substituent. (Item 4) R 1 and R 2 The phosphine oxide compound or a salt thereof according to Item 1, wherein the aryl groups in each have two substituents. (Item 5) R 1 and R 2 The phosphine oxide compound or a salt thereof according to Item 1, wherein the aryl groups in each have three substituents. (Item 6) The said R 1 and R 2 The compound or a salt thereof according to any one of Items 1 to 5, wherein the substituents on the aryl groups in are selected from the group consisting of halogen, alkyl, -O alkyl, -OH, -NO2, -NH2, -C(=O)H, -C(=O) alkyl, and -C(=O)O alkyl, and the alkyl is substituted or unsubstituted. (Item 7) The said R 1 and R 2 The compound or a salt thereof according to any one of Items 1 to 6, wherein the substituents on the aryl groups in are selected from the group consisting of halogen, -C1 to C4 alkyl, -OC1 to C4 alkyl, -OH, -NO2, -NH2, -C(=O)H, -C(=O)C1 to C4 alkyl, and -C(=O)OC1 to C4 alkyl, and the alkyl is substituted or unsubstituted. (Item 8) R 1 and R 2 wherein the substituents are each independently a -C1 to C4 alkyl group, the phosphine oxide compound or a salt thereof according to any one of Items 1 to 7. (Item 9) R 1 and R 2 wherein the aryl group having the substituent is a monocyclic, bicyclic or tricyclic group having a substituent, the phosphine oxide compound or a salt thereof according to any one of Items 1 to 8. (Item 10) R 1 and R 2 wherein the aryl group having the substituent is a phenyl group having a substituent, the phosphine oxide compound or a salt thereof according to any one of Items 1 to 9. (Item 11) R 1 and R 2 are

[0007] [Chemical formula]

[0008] where * indicates the bonding point, the phosphine oxide compound or a salt thereof according to any one of Items 1 to 10. (Item 12) R a is a group having an unsaturated double bond at the terminal, a group having an epoxy group at the terminal, an aryl group having two or more hydroxyls, or a group containing a phosphine oxide, the phosphine oxide compound or a salt thereof according to any one of Items 1 to 11. (Item 13) R a is

[0009] [Chemical formula]

[0010] ,

[0011]

Chem.

[0012] or a dihydroxy-substituted aryl group, and R 3 and R 4 are each independently hydrogen or a substituted or unsubstituted alkyl group, n is 1 or 2, where when n is 2, each R 3 may be the same or different, and each R 4 may be the same or different, R 5 is hydrogen or a substituted or unsubstituted alkyl group, R 6 R 7 R 8 and R 9 are each independently hydrogen or a substituted or unsubstituted alkyl group, n1 and n2 are each independently 1 to 3, where when n1 is 2 or 3, each R 6 may be the same or different, and each R 7 may be the same or different, where when n2 is 2 or 3, each R 8 may be the same or different, and each R 9 may be the same or different, * indicates the bonding point, The phosphine oxide compound or a salt thereof according to any one of Items 1 to 12. (Item 14) R a is an acryloyloxymethyl group, a methacryloyloxymethyl group, an epoxy methyloxypropyl group or a 2,5-dihydroxyphenyl group, and the phosphine oxide compound or a salt thereof according to any one of Items 1 to 13. (Item 15) The phosphine oxide compound is represented by the following general formula (I)

[0013] [Chemical formula]

[0014] (I) wherein R 1 , R 2 are as described in Item 1, and R 3 , R 4 , n and R 5 are as described in Item 13, the compound described in Item 13 or a salt thereof. (Item 16) R 1 and R 2 in which the aryl groups each independently have one, two or three substituents, the phosphine oxide compound described in Item 15 or a salt thereof. (Item 17) The substituents on the aryl group in the above R 1 and R 2 are substituted or unsubstituted alkyl, the phosphine oxide compound described in Item 16 or a salt thereof. (Item 18) The phosphine oxide compound is represented by the following general formula (II)

[0015] [Chemical formula]

[0016] (II) wherein R 1 , R 2 are as described in Item 1, and R 6 , R 7 , R 8 , R 9 , n1, and n2 are as described in Item 13, the compound described in Item 13 or a salt thereof. (Item 19) R 1and R 2 The phosphine oxide compound or a salt thereof according to item 18, wherein the aryl group in 2 has, independently of each other, one, two or three substituents. (Item 20) Said R 1 and R 2 The phosphine oxide compound or a salt thereof according to item 19, wherein the substituent on the aryl group in 1 and 2 is a substituted or unsubstituted alkyl. (Item 21) The phosphine oxide compound is represented by the following general formula (III)

[0017]

Chemical formula

[0018] (III) and is represented by the formula: R 1 , R 2 are as defined in item 1. The compound or a salt thereof according to item 13. (Item 22) R 1 and R 2 The phosphine oxide compound or a salt thereof according to item 21, wherein the aryl group in 1 and 2 has, independently of each other, two or three substituents. (Item 23) Said R 1 and R 2 The phosphine oxide compound or a salt thereof according to item 22, wherein the substituent on the aryl group in 1 and 2 is a substituted or unsubstituted alkyl. (Item 24) The phosphine oxide compound is represented by the following general formula (IV) (R 1 )(R 2 )P(=O)-(linker)-P(=O)(R 1 )(R 2 ) (IV) and is represented by the formula: R 1 and R 2The compound or a salt thereof according to item 1, as described in item 1. (Item 25) The linker is -(C(R 10 )(R 11 )) n3 -(Ar) n5 -(C(R 12 )(R 13 )) n4 - and R 10 R 11 R 12 and R 13 are each independently selected from the group consisting of hydrogen, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, and a substituted or unsubstituted aminocarbonyl group. Ar is a substituted or unsubstituted arylene group or heteroarylene group. n3, n4 and n5 are each independently 0 to 3. The compound or a salt thereof according to item 24. (Item 26) R 1 and R 2 wherein the aryl groups in are each independently having three substituents, n3 and n4 are 0, n5 is 1 to 3, and the Ar is an unsubstituted arylene group or heteroarylene group, the compound or a salt thereof according to item 25. (Item 27) The 1 R 2 and the substituent on the aryl group in R is a substituted or unsubstituted alkyl, the phosphine oxide compound or a salt thereof according to item 26. (Item 28) R 1 and R2 The compound or a salt thereof according to item 27, wherein the aryl groups each independently have a substituted or unsubstituted alkyl group, and n3, n4 and n5 are each independently 1 to 3. (Item 29) The linker is

[0019] [Chemical formula]

[0020] The compound or a salt thereof according to item 28, which is (Item 30) The phosphine oxide compound is represented by the following general formula (IVa)

[0021] [Chemical formula]

[0022] (IVa) represented by R 1 and R 2 are as described in item 1, R 10 and R 11 are each independently selected from the group consisting of hydrogen, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group and a substituted or unsubstituted aminocarbonyl group, The compound or a salt thereof according to item 24. (Item 31) R 1 and R 2 The phosphine oxide compound or a salt thereof according to item 30, wherein the aryl groups each independently have three substituents. (Item 32) Said R 1 and R 2 The phosphine oxide compound or a salt thereof according to Item 31, wherein the substituent on the aryl group in is a substituted or unsubstituted alkyl group. (Item 33) The following general formula (V)

[0023] [Chemical formula]

[0024] (V) (In the formula, R 1 and R 2 are each independently a substituted or unsubstituted aryl group, R 3 and R 4 are each independently hydrogen or a substituted or unsubstituted alkyl group, n is 1 or 2, here, when n is 2, each R 3 may be the same or different from each other, and each R 4 may be the same or different from each other, R 5 is hydrogen or a substituted or unsubstituted alkyl group) A homopolymer or copolymer containing as a constituent. (Item 34) The copolymer according to Item 33, which is a copolymer with (meth) acrylic acid, (meth) acrylic acid ester, (meth) acrylic acid halide, (meth) acrylate, styrene or acrylonitrile. (Item 35) The following general formula (VI)

[0025] [Chemical formula]

[0026] (VI) (In the formula, R 1 and R 2 are each independently a substituted or unsubstituted aryl group, R 6 , R 7 , R 8 , and R 9 are each independently hydrogen, or a substituted or unsubstituted alkyl group, n1 and n2 are each independently 1 or 2, wherein when n1 is 2, each R 6 may be the same or different, and each R 7 may be the same or different, wherein when n2 is 2, each R 8 may be the same or different, and each R 9 may be the same or different) and a homopolymer or copolymer containing the same as a constituent. (Item 36) The copolymer according to Item 35, which is a copolymer with an epoxy compound. (Item 37) An additive containing the compound or salt according to any one of Items 1 to 32, or the homopolymer or copolymer according to any one of Items 33 to 36. (Item 38) An anti-fogging agent containing the compound or salt according to any one of Items 1 to 32, or the homopolymer or copolymer according to any one of Items 33 to 36. (Item 39) A flame retardant containing the compound or salt according to any one of Items 1 to 32, or the homopolymer or copolymer according to any one of Items 33 to 36. (Item 40) Parts for electric / electronic applications, parts for OA-related applications, parts for automobiles, parts for trains, parts for aircraft, or fibers containing the compound or salt according to any one of Items 1 to 32, or the homopolymer or copolymer according to any one of Items 33 to 36. (Item 41) A sheet, film, or acrylic glass containing the compound or salt according to any one of items 1 to 32, or the homopolymer or copolymer according to any one of items 33 to 36. (Item 42) A polymerization additive containing the compound or salt according to any one of items 1 to 32, or the homopolymer or copolymer according to any one of items 33 to 36. (Item 43) A surface modifier containing the compound or salt according to any one of items 1 to 32, or the homopolymer or copolymer according to any one of items 33 to 36. (Item 44) A phosphorus-imparting agent containing the compound or salt according to any one of items 1 to 32, or the homopolymer or copolymer according to any one of items 33 to 36. (Item 45) Use of the compound or salt according to any one of items 1 to 32, or the homopolymer or copolymer according to any one of items 33 to 36 in electrical / electronic-related parts, OA-related parts, automotive parts, railway parts, aircraft parts, fibers, sheets, films, or acrylic glass, or use of the compound or salt according to any one of items 1 to 32, or the homopolymer or copolymer according to any one of items 33 to 36 as an additive, anti-fogging agent, flame retardant, polymerization additive, surface modifier, or phosphorus-imparting agent. (Item 46) A method of using the compound or salt according to any one of items 1 to 32, or the homopolymer or copolymer according to any one of items 33 to 36 in electrical / electronic-related parts, OA-related parts, automotive parts, railway parts, aircraft parts, fibers, sheets, films, or acrylic glass, or using it as an additive, anti-fogging agent, flame retardant, polymerization additive, surface modifier, or phosphorus-imparting agent, the method comprising the step of applying the compound or salt, or the homopolymer or copolymer, to an object in need thereof.

[0027] In the present disclosure, it is intended that one or more of the above features may be provided in combination in addition to the explicitly stated combinations. 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 as needed.

Advantages of the Invention

[0028] The present disclosure provides a novel compound that is a diarylphosphine oxide derivative. Materials using this novel compound have low water absorption and can be used for various applications. The diarylphosphine oxide derivative of the present disclosure suppresses the sway of the aryl group by introducing a steric hindrance substituent such as a methyl group into the aryl group, reducing loss, and can obtain a resin with lower dielectric constant (Dk) and dielectric tangent (Df) and high insulation.

Brief Description of the Drawings

[0029]

Figure 1

Figure 2

Modes for Carrying Out the Invention

[0030] Hereinafter, the present disclosure will be described while showing the best mode. Throughout this specification, it should be understood that singular expressions include the concepts of their plurals unless otherwise specified. Therefore, singular articles (e.g., "a", "an", "the" in English, etc.) should be understood to include the concepts of their plurals unless otherwise specified. Also, the terms used in this specification should be understood to be used in the meanings commonly used in the art unless otherwise specified. Therefore, unless otherwise defined, all technical and scientific terms used in this specification have the same meaning as commonly understood by those skilled in the art to which the present disclosure pertains. In case of contradiction, this specification (including the definitions) shall prevail.

[0031] (Definition of Terms) The terms used in this specification are explained below.

[0032] In this specification, "substitution" means replacing a specific hydrogen atom of an organic compound with another atom or atomic group.

[0033] In this specification, "substituent" means an atom or functional group that substitutes another in a chemical structure.

[0034] In this specification, unless otherwise specified, substitution means replacing one or more hydrogen atoms in an organic compound or substituent with another atom or atomic group, or forming a double bond or triple bond. It is also possible to remove one hydrogen atom to substitute with a monovalent substituent or to form a double bond together with a single bond, and it is also possible to remove two hydrogen atoms to substitute with a divalent substituent or to form a triple bond together with a single bond.

[0035] Examples of substituents in the present disclosure include, but are not limited to, hydrogen, halogen group, alkyl group, alkoxy group, -OH group, -NO2 group, -NH2 group, -C(=O)H group, alkylcarbonyl group, and alkoxycarbonyl group. Preferred groups of substituents in the present disclosure include halogen, alkyl, -Oalkyl, -OH, -NO2, -NH2, -C(=O)H, -C(=O)alkyl, and -C(=O)Oalkyl. Even more preferred groups of substituents in the present disclosure include halogen, -C1-C4 alkyl (e.g., -CH3), -OC1-C4 alkyl (e.g., -OCH3), -OH, -NO2, -NH2, -C(=O)H, -C(=O)C1-C4 alkyl (e.g., -C(=O)CH3), and -C(=O)OC1-C4 alkyl. All substituents may have substituents other than hydrogen.

[0036] In this specification, C1, C2,..., Cn represent the number of carbon atoms (where n represents any positive integer). Therefore, C1 is used to represent a substituent having 1 carbon atom.

[0037] As used herein, "alkyl" refers to a monovalent group formed by the loss of one hydrogen atom from an aliphatic hydrocarbon (alkane) such as methane, ethane, or propane, and is generally represented by C n H 2n+1 - (where n is a positive integer). Alkyl can be straight-chain or branched-chain. As used herein, "substituted alkyl" refers to an alkyl in which one or more hydrogens of the alkyl are substituted by the substituents defined above. Specific examples thereof can 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 examples include methyl (CH3-), ethyl (C2H5-), n-propyl (CH3CH2CH2-), isopropyl ((CH3)2CH-), n-butyl (CH3CH2CH2CH2-), n-pentyl (CH3CH2CH2CH2CH2-), n-hexyl (CH3CH2CH2CH2CH2CH2-), n-heptyl (CH3CH2CH2CH2CH2CH2CH2-), n-octyl (CH3CH2CH2CH2CH2CH2CH2CH2-), n-nonyl (CH3CH2CH2CH2CH2CH2CH2CH2CH2-), n-decyl (CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2-), -C(CH3)2CH2CH2CH(CH3)2, -CH2CH(CH3)2, and the like. Further, for example, C1-C10 substituted alkyl refers to a C1-C10 alkyl in which one or more hydrogen atoms thereof are substituted by substituents.

[0038] As used herein, the term "cycloalkyl group" refers to an alkyl having a cyclic structure. Specific examples include C3-C4 cycloalkyl, C3-C5 cycloalkyl, C3-C6 cycloalkyl, C3-C7 cycloalkyl, C3-C8 cycloalkyl, C3-C9 cycloalkyl, C3-C10 cycloalkyl, C3-C11 cycloalkyl, C3-C20 cycloalkyl, C3-C4 substituted cycloalkyl, C3-C5 substituted cycloalkyl, C3-C6 substituted cycloalkyl, C3-C7 substituted cycloalkyl, C3-C8 substituted cycloalkyl, C3-C9 substituted cycloalkyl, C3-C10 substituted cycloalkyl, C3-C11 substituted cycloalkyl, or C3-C20 substituted cycloalkyl. For example, cycloalkyl groups include cyclopropyl, cyclohexyl, and the like. The term "substituted cycloalkyl group" refers to a cycloalkyl in which the hydrogen of the cycloalkyl is substituted.

[0039] As used herein, the term "alkoxy group" refers to a monovalent group formed by the loss of a hydrogen atom of the hydroxy group of an alcohol, and is generally represented by C n H 2n+1 O- (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 by the substituents defined above. Specific examples include 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 a linear or branched alkoxy containing 1 to 10 carbon atoms, and examples include methoxy (CH3O-), ethoxy (C2H5O-), n-propoxy (CH3CH2CH2O-), and the like.

[0040] As used herein, "alkoxycarbonyl" refers to an (alkoxy)C(=O)- group, and alkoxy is as defined above for "alkoxy".

[0041] As used herein, "heterocyclic group" refers to a group having a cyclic structure containing carbon and heteroatoms. Here, the heteroatoms are selected from the group consisting of O, S, and N, may be the same or different, and may include one or two or more. The heterocyclic group may be aromatic or non-aromatic, and may be monocyclic or polycyclic. The heterocyclic group may be substituted. "Substituted heterocyclic group" refers to a group in which the hydrogen of the heterocyclic group is substituted.

[0042] As used herein, "aryl group" refers to a group formed by the removal of one hydrogen atom bonded to the ring of an aromatic hydrocarbon. From benzene, a phenyl group (C6H5-), from toluene, a tolyl group (CH3C6H4-), from xylene, a xylyl group ((CH3)2C6H3-), and from naphthalene, a naphthyl group (C 10 H8-) is derived. The number of carbon atoms includes those having 6 to 12 carbon atoms. The aryl group includes a monocyclic (phenyl group), bicyclic (naphthyl group), and tricyclic (anthracenyl group, etc.).

[0043] As used herein, "heteroaryl group" refers to a group in which one or more of the carbon atoms constituting the ring of an aromatic hydrocarbon are substituted with heteroatoms. For example, but not limited to, pyridine, pyrrole, thiophene, furan, imidazole, oxazole, thiazole, indole, quinoline, isoquinoline, quinoxaline, pyrazine, benzimidazole.

[0044] As used herein, "aryloxy group" refers to a monovalent group formed by the loss of the hydrogen atom of the hydroxy group of an aryl group substituted by a hydroxy group. For example, but not limited to, C6H5O-, CH3C6H4O-, (CH3)2C6H3O-, C 10 H8O-.

[0045] As used herein, the "thioalkoxy group" is a group in which the oxygen atom of the "alkoxy group" is replaced by a sulfur atom, and is generally represented by -SR (where R is an alkyl group).

[0046] As used herein, the "alkoxycarbonyl group" refers to a group represented by -C(O)OR (where R is an alkyl group). The "substituted alkoxycarbonyl group" refers to a group in which the hydrogen of the alkoxycarbonyl group is substituted.

[0047] As used herein, the "halogen (group)" refers to a monovalent group of an element such as chlorine (Cl), bromine (Br), iodine (I), etc., belonging to Group 17 of the periodic table (in the most recent definition, it is called Group 17).

[0048] As used herein, the "alkylcarbonyl group" refers to a monovalent group formed by removing OH from a carboxylic acid. Representative examples of the alkylcarbonyl group include acetyl (CH3CO-), C2H5CO-, etc. The number of carbon atoms in the alkyl part can be 1 to 6, etc. The "substituted alkylcarbonyl group" refers to a group in which the hydrogen of the acyl is substituted with the substituent defined above.

[0049] As used herein, the "aminocarbonyl group" is a group in which the hydrogen of ammonia or an amine is substituted with an acid group (acyl group). The "substituted aminocarbonyl group" refers to a group in which the hydrogen on nitrogen is substituted. The aminocarbonyl group is also referred to as an amide.

[0050] As used herein, the "arylene group" refers to a group formed by the removal of two hydrogen atoms bonded to the ring of an aromatic hydrocarbon. From benzene, a phenylene group (-C6H4-), from toluene, a methylphenylene group (-CH3C6H3-), from xylene, a dimethylphenylene group (-(CH3)2C6H3-), and from naphthalene, a naphthylene group (-C 10 H7-) is derived. The number of carbon atoms can be 6 to 12.

[0051] As used herein, the term "heteroarylene group" refers to a group in which one or more carbon atoms constituting the ring of an aromatic hydrocarbon are substituted with heteroatoms and which has two bonding points. For example, but not limited to, pyridinediyl, pyrrolediyl, thiophenediyl, furandiyl, imidazolediyl, oxazolediyl, thiazolediyl, indolediyl, quinolinediyl, isoquinolinediyl, quinoxalinediyl, pyrazinediyl, benzimidazolediyl.

[0052] As used herein, the term "group having an unsaturated double bond" refers to a group containing a carbon-carbon double bond such as an alkene, and examples thereof include groups composed only of carbon such as ethylene and propylene, and groups containing a carboxylate group such as acrylic and methacrylic.

[0053] As used herein, the term "group having an epoxy group" refers to a group having an oxacyclopropane (oxirane), which is a three-membered ring ether, in its structural formula. Examples thereof include an epoxy group, an epoxy methyl group, an epoxy ethyl group, an epoxy propyl group, an epoxy methyloxy group, an epoxy ethyloxy group, an epoxy propyloxy group, an epoxy methyloxymethyl group, an epoxy methyloxyethyl group, an epoxy methyloxypropyl group, an epoxy ethyloxymethyl group, an epoxy ethyloxyethyl group, an epoxy ethyloxypropyl group, an epoxy propyloxymethyl group, an epoxy propyloxyethyl group, an epoxy propyloxypropyl group.

[0054] As used herein, the term "epoxy compound" refers to a compound containing an epoxy group. It may contain a group as listed in the "group having an epoxy group".

[0055] As used herein, the term "group containing a hydroxy group" refers to any group containing a hydroxy group as a functional group. It also includes groups containing an OH group in an aromatic such as phenol. Examples thereof include a hydroxyphenyl group, a dihydroxyphenyl group, a trihydroxyphenyl group.

[0056] As used herein, the term "phosphorus-containing group" refers to any group containing phosphorus. Phosphorus may be phosphine oxide, phosphine dioxide (hypophosphorous acid), phosphine trioxide (phosphorous acid), or phosphine tetraoxide (phosphoric acid).

[0057] As used herein, the term "linker" refers to a group that connects two or more groups. The linker may be a group that does not react in the intended use.

[0058] As used herein, the term "polymer" also referred to as a macromolecule, is a substance composed of molecules in which one or several kinds of atoms or atomic groups are used as structural units and are repeatedly linked to each other in large numbers, and the number of repetitions of the structural units of the molecule is very large and certain physical properties of the substance do not change with the increase or decrease of one or several structural units. Examples of polymers include homopolymers and copolymers.

[0059] As used herein, the term "monomer" also referred to as a monomeric unit, 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 may form multiple types of structural units. The monomers of the present disclosure can also bind to other substances via radical polymerization.

[0060] As used herein, the term "homopolymer" also referred to as a homopolymeric unit, refers to a polymer obtained by polymerization using a single monomer.

[0061] As used herein, the term "copolymer" also referred to as a copolymeric unit, refers to a polymer obtained by polymerization using multiple monomers. In a representative embodiment of the present disclosure, it may be formed by copolymerization with a monomer different from the monomers of the present disclosure. Examples of monomers different from the monomers of the present disclosure include (meth)acrylic acid, (meth)acrylic acid esters (e.g., methyl (meth)acrylate), (meth)acrylic acid halides, (meth)acrylates, styrene, or acrylonitrile.

[0062] As used herein, "polymerization" refers to a reaction in which a high molecular weight compound (polymer) is formed from a low molecular weight compound (monomer).

[0063] As used herein, "(meth)acrylic acid" refers to acrylic acid and / or methacrylic acid.

[0064] As used herein, "acid halide" is also referred to as acid halide, and refers to a compound in which the OH group contained in the carboxyl group of a carboxylic acid is substituted with a halogen. Depending on the type of halogen, there are four types: acid fluoride, acid chloride, acid bromide, and acid iodide.

[0065] As used herein, "base" refers to that according to the definition of Bronsted-Lowry, and refers to a substance that accepts a proton. Examples of "base" include salts of weak acids and alkali metals. Alkali metal carbonates (e.g., K2CO3) are included.

[0066] As used herein, "alkali metal" refers to lithium, sodium, potassium, rubidium, cesium, and francium.

[0067] As used herein, "(meth)acrylic acid" indicates acrylic acid, methacrylic acid, or both.

[0068] As used herein, "additive" refers to a substance added to any substance.

[0069] As used herein, "anti-fogging agent" refers to a substance that maintains the transparency of a certain material (e.g., polyacrylic acid), and the maintenance of transparency is typically achieved by making the surface of the substance more hydrophobic.

[0070] As used herein, the "phosphorus-imparting agent" refers to a substance that imparts a phosphorus component to a certain substance, and is typically achieved by bonding a phosphorus-containing group to a certain substance. A phosphorus-imparting agent having a (meth)acrylic group can bond a phosphorus-containing group to a compound having a radically polymerizable group by radical polymerization. Phosphorus-imparting agents can be used, for example, in the production of fertilizers, agricultural chemicals, pharmaceuticals, insecticides, gunpowders, electronic materials, catalysts, flame retardants, metal surface treatment agents, detergents, antifreeze liquids, surfactants, defoaming agents, and lubricants.

[0071] As used herein, the "radically 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 terminal in a substituent. Such radically polymerizable groups include, but are not limited to, allyl, substituted allyl, styrene, substituted styrene, acrylic, substituted acrylic, methacrylic, substituted methacrylic, etc.

[0072] 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, iron), ammonium, organic bases and amino acids, or 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) can be mentioned. Particularly, hydrochloric acid, phosphoric acid, tartaric acid or methanesulfonic acid, etc. can be mentioned. These salts can be formed by commonly practiced methods.

[0073] The compounds of the present disclosure are not limited to specific isomers, but include all possible isomers (such as keto-enol isomers, imine-enamine isomers, diastereoisomers, optical isomers and rotational isomers, etc.) and racemates.

[0074] One or more hydrogens, carbons or other atoms of the compounds of the present disclosure may be substituted with isotopes of hydrogen, carbon or other atoms. The compounds of the present disclosure include all radiolabeled forms of the compounds of the present disclosure. Examples of isotopes that can be incorporated into the compounds of the present disclosure include, respectively 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 Cl, including hydrogen, carbon, nitrogen, oxygen, phosphorus, sulfur, fluorine, iodine and chlorine.

[0075] (Description of Preferred Embodiments) 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 those skilled in the art can make appropriate modifications within the scope of the present disclosure by referring to the descriptions in this specification. It is also understood that the following embodiments of the present disclosure can be used alone or in combination.

[0076] In one aspect, the present disclosure provides a phosphine oxide compound represented by the following general formula R a -P(=O)R 1 R 2 or a salt thereof, wherein In the formula, R 1 and R 2 are different or the same and are each independently an aryl group having a substituent, R a is a group having an unsaturated double bond, a group having an epoxy group, a group containing a hydroxy group, or a group containing phosphorus. Provided is a phosphine oxide compound or a salt thereof.

[0077] Products of various compounds derived from the diarylphosphine oxide derivatives having substituents on the aryl groups of the present disclosure have less electrical loss (dielectric tangent, Df) and can be products with higher insulation properties with lower dielectric constant (Dk) and lower dielectric tangent (Df) compared to the phosphine oxide forms of aryl groups without corresponding substituents. Without wishing to be bound by theory, the introduction of sterically hindering substituents suppresses the sway of the aryl group, resulting in less loss, lower dielectric constant (Dk) and lower dielectric tangent (Df), and higher insulation properties.

[0078] In one embodiment, R 1 and R 2 the aryl groups in each have, independently of each other, one, two or three substituents. By adjusting the number of substituents, products with desired electrical properties can be obtained.

[0079] In one embodiment, R 1 and R 2 the aryl groups in each have one substituent.

[0080] In one embodiment, R 1 and R 2 the aryl groups in each have two substituents.

[0081] In one embodiment, R 1 and R 2 the aryl groups in each have three substituents.

[0082] In one embodiment, the R 1 and R 2The substituent on the aryl group in [the compound] is selected from the group consisting of halogen, alkyl, -O alkyl, -OH, -NO2, -NH2, -C(=O)H, -C(=O) alkyl, and -C(=O)O alkyl, and the alkyl is substituted or unsubstituted. Without wishing to be bound by theory, the introduction of polar groups can adjust the conductivity and prepare desirable products.

[0083] In one embodiment, the R 1 and R 2 The substituent on the aryl group in [the compound] is selected from the group consisting of halogen, -C1-C4 alkyl, -OC1-C4 alkyl, -OH, -NO2, -NH2, -C(=O)H, -C(=O)C1-C4 alkyl, and -C(=O)OC1-C4 alkyl, and the alkyl is substituted or unsubstituted.

[0084] In one embodiment, R 1 and R 2 In [the compound], the substituents are each independently a -C1-C4 alkyl group.

[0085] In one embodiment, R 1 and R 2 In [the compound], the aryl group having the substituent is a monocyclic, bicyclic or tricyclic group having a substituent. Without wishing to be bound by theory, the dielectric tangent (Df) can be adjusted by the size of the ring of the aryl group, and desirable products can be prepared.

[0086] In one embodiment, R 1 and R 2 In [the compound], the aryl group having the substituent is a phenyl group having a substituent.

[0087] In one embodiment, R 1 and R 2 are

[0088]

Chemical formula

[0089] where * indicates a junction point.

[0090] In one embodiment, R a is a group having an unsaturated double bond at the terminal, a group having an epoxy group at the terminal, an aryl group having two or more hydroxyls, or a group containing a phosphine oxide. By adjusting R a , it can be used for various applications.

[0091] In one embodiment, R a is

[0092]

Chemical formula

[0093] ,

[0094]

Chemical formula

[0095] , or a dihydroxy-substituted aryl group, and R 3 and R 4 are each independently hydrogen or a substituted or unsubstituted alkyl group, n is 1 or 2, where, when n is 2, each R 3 can be the same or different, and each R 4 can be the same or different, R 5 is hydrogen or a substituted or unsubstituted alkyl group, R 6 , R 7 , R 8 , and R 9 are each independently hydrogen or a substituted or unsubstituted alkyl group, n1 and n2 are each independently 1 to 3, Here, when n1 is 2 or 3, each R 6 may be the same or different, and each R 7 may be the same or different, Here, when n2 is 2 or 3, each R 8 may be the same or different, and each R 9 may be the same or different, * indicates a bonding point.

[0096] In one embodiment, R a is an acryloyloxymethyl group, a methacryloyloxymethyl group, an epoxy methyloxypropyl group or a 2,5-dihydroxyphenyl group.

[0097] In one embodiment, the phosphine oxide compound has the following general formula (I)

[0098]

Chemical formula

[0099] (I) represented by, R 1 , R 2 is as described above, and R 3 , R 4 , n and R 5 are as described above.

[0100] In one embodiment, the phosphine oxide compound has the following general formula (II)

[0101]

Chemical formula

[0102] (II) represented by, R 1 , R 2 is as described above, and R 6 , R 7 , R8 、R 9 、n1, and n2 are as described above.

[0103] In one embodiment, the phosphine oxide compound has the following general formula (III)

[0104]

Chemical formula

[0105] (III) as shown, where R 1 、R 2 are as described above. The above compound can be kneaded with a resin.

[0106] In one embodiment, the phosphine oxide compound has the following general formula (IV) (R 1 )(R 2 )P(=O)-(linker)-P(=O)(R 1 )(R 2 ) (IV) as shown, R 1 and R 2 are as described above. The linker can be a group that is not reactive in the intended application. By adjusting the linker, phosphine oxide compounds with various properties can be obtained.

[0107] In one embodiment, the linker is -(C(R 10 )(R 11 )) n3 -(Ar) n5 -(C(R 12 )(R 13 )) n4 - where R 10 、R 11 、R 12 、and R 13are each independently selected from the group consisting of hydrogen, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, and a substituted or unsubstituted aminocarbonyl group, Ar is a substituted or unsubstituted arylene group or heteroarylene group, n3, n4 and n5 are each independently 0 to 3.

[0108] In one embodiment, the linker is

[0109]

Chemical formula

[0110] as follows.

[0111] In one embodiment, the phosphine oxide compound is represented by the following general formula (IVa)

[0112]

Chemical formula

[0113] (IVa) as shown below, R 1 and R 2 are as described above, R 10 and R 11Each is independently selected from the group consisting of hydrogen, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, and a substituted or unsubstituted aminocarbonyl group.

[0114] In one aspect, the present disclosure provides a homopolymer or copolymer comprising, as a constituent, the following general formula (V)

[0115] [Chemical formula]

[0116] (V) (wherein R 1 and R 2 are each independently a substituted or unsubstituted aryl group, R 3 and R 4 are each independently hydrogen or a substituted or unsubstituted alkyl group, n is 1 or 2, wherein when n is 2, each R 3 may be the same or different, and each R 4 may be the same or different, R 5 is hydrogen or a substituted or unsubstituted alkyl group).

[0117] In one embodiment, it is a copolymer with (meth)acrylic acid, (meth)acrylate, (meth)acrylic acid halide, (meth)acrylate salt, styrene, or acrylonitrile.

[0118] In one embodiment, the following general formula (VI)

[0119] [Chemical formula]

[0120] (VI) (wherein R 1 and R 2 are each independently a substituted or unsubstituted aryl group, R 6 R 7 R 8 and R 9 are each independently hydrogen or a substituted or unsubstituted alkyl group, n1 and n2 are each independently 1 or 2, here, when n1 is 2, each R 6 may be the same or different, and each R 7 may be the same or different, here, when n2 is 2, each R 8 may be the same or different, and each R 9 may be the same or different) is a homopolymer or copolymer containing as a constituent.

[0121] In one embodiment, it is a copolymer with an epoxy compound. With the phosphine oxide of the present disclosure, various epoxy compounds can be modified.

[0122] In one aspect, an additive is provided that includes the above compound or salt, or homopolymer or copolymer.

[0123] In one aspect, an anti-fogging agent is provided that includes the above compound or salt, or homopolymer or copolymer.

[0124] In one aspect, a flame retardant is provided that includes the above compound or salt, or homopolymer or copolymer.

[0125] In one aspect, there is provided a component for electrical / electronic applications, an OA-related component, an automotive component, a railway component, an aircraft component, or a fiber, which contains the above compound or salt, or a homopolymer or copolymer.

[0126] In one aspect, there is provided a sheet, a film, or an acrylic glass, which contains the above compound or salt, or a homopolymer or copolymer.

[0127] In one aspect, there is provided a polymerization additive, which contains the above compound or salt, or a homopolymer or copolymer.

[0128] In one aspect, there is provided a surface modifier, which contains the above compound or salt, or a homopolymer or copolymer.

[0129] In one aspect, there is provided a phosphorus donor, which contains the above compound or salt, or a homopolymer or copolymer.

[0130] In one aspect, there is provided the use of the compound or salt of the present disclosure, or the homopolymer or copolymer of the present disclosure, in an additive, an anti-fogging agent, a flame retardant, a component for electrical / electronic applications, an OA-related component, an automotive component, a railway component, an aircraft component, a fiber, a sheet, a film, an acrylic glass, a polymerization additive, a surface modifier, or a phosphorus donor. These uses also include the use of the compound or salt of the present disclosure, or the homopolymer or copolymer of the present disclosure, for satisfying two or more, three or more, etc. a large number of uses simultaneously among an additive, an anti-fogging agent, a flame retardant, a component for electrical / electronic applications, an OA-related component, an automotive component, a railway component, an aircraft component, a fiber, a sheet, a film, an acrylic glass, a polymerization additive, a surface modifier, or a phosphorus donor.

[0131] In one aspect, the present disclosure provides a method of using a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, in electrical / electronic related components, OA related components, automotive components, train components, aircraft components, fibers, sheets, films or acrylic glass, or as an additive, anti-fogging agent, flame retardant, polymerization additive, surface modifier or phosphorus-imparting agent, the method comprising applying the compound or salt, or the homopolymer or copolymer, to an object in need thereof.

[0132] In a more specific embodiment, the method of the present disclosure comprises adding a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, to an object (for example, including polyester resin, aromatic polyester resin, polyurethane resin, polyvinyl chloride resin, polyamide resin, polyimide resin, polycarbonate resin, ABS resin, AS resin, BT resin, polyethylene resin, polypropylene resin, polystyrene resin, poly(meth)acrylic resin, polyacetal resin, polyvinyl acetate resin, epoxy resin, phenol resin, melamine resin, benzoxazine resin as a main component).

[0133] In another embodiment, the method of the present disclosure comprises adding a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, to an object (for example, a material intended for anti-fogging, such as poly(meth)acrylic resin, polycarbonate resin, polyester resin, polystyrene resin), and optionally a step of completing the product.

[0134] In another embodiment, the method of the present disclosure includes a step of adding a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, to an object (for example, a material intended to be flame-retardant, such as a polyester resin, an aromatic polyester resin, a polyurethane resin, a polyvinyl chloride resin, a polyamide resin, a polyimide resin, a polycarbonate resin, an ABS resin, an AS resin, a BT resin, a polyethylene resin, a polypropylene resin, a polystyrene resin, a poly(meth)acrylic resin, a polyacetal resin, a polyvinyl acetate resin, an epoxy resin, a phenol resin, a melamine resin, a benzoxazine resin), and a step of completing the product as necessary.

[0135] In another embodiment, the method of the present disclosure includes a step of adding a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, to an object (for example, parts for electric / electronic applications, parts for OA-related applications, parts for automobiles, parts for trains, parts for aircraft, for example, mainly composed of a polyester resin, an aromatic polyester resin, a polyurethane resin, a polyvinyl chloride resin, a polyamide resin, a polyimide resin, a polycarbonate resin, an ABS resin, an AS resin, a BT resin, a polyethylene resin, a polypropylene resin, a polystyrene resin, a poly(meth)acrylic resin, a polyacetal resin, a polyvinyl acetate resin, an epoxy resin, a phenol resin, a melamine resin, a benzoxazine resin), and a step of completing the product as necessary.

[0136] In another embodiment, the method of the present disclosure includes the steps of adding a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, to an object (e.g., a fiber, sheet, film, e.g., mainly composed of a polyester resin, aromatic polyester resin, polyurethane resin, polyvinyl chloride resin, polyamide resin, polyimide resin, polycarbonate resin, ABS resin, AS resin, BT resin, polyethylene resin, polypropylene resin, polystyrene resin, poly(meth)acrylic resin, polyacetal resin, polyvinyl acetate resin, epoxy resin, phenol resin, melamine resin, benzoxazine resin), and, if necessary, the step of completing the product.

[0137] In another embodiment, the method of the present disclosure includes the steps of adding or applying a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, to an object (e.g., acrylic glass, e.g., poly(meth)acrylic resin), and, if necessary, the step of completing the product.

[0138] In another embodiment, the method of the present disclosure includes the steps of adding or applying a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, as a polymerization additive, surface modifier or phosphorus-imparting agent, to an object (e.g., a material intended for polymerization, surface modification or phosphorus imparting, e.g., a polyester resin, aromatic polyester resin, polyurethane resin, polyvinyl chloride resin, polyamide resin, polyimide resin, polycarbonate resin, ABS resin, AS resin, BT resin, polyethylene resin, polypropylene resin, polystyrene resin, poly(meth)acrylic resin, polyacetal resin, polyvinyl acetate resin, epoxy resin, phenol resin, melamine resin, benzoxazine resin), and, if necessary, the step of completing the product.

[0139] In one embodiment, when the polymer of the present disclosure is a copolymer, it can be a copolymer copolymerized with a radically polymerizable monomer. The radically polymerizable monomer can include, but is not limited to, styrene and acrylic esters (e.g., alkyl acrylates such as methyl acrylate and ethyl acrylate, alkyl styrenes such as methyl styrene and ethyl styrene, etc.).More specifically, examples of radical polymerization monomers that can be used to produce the polymers of the present disclosure include, for example, such radical polymerization monomers as styrene, 2-methoxystyrene, 3-methoxystyrene, 4-methoxystyrene, 2-t-butoxystyrene, 3-t-butoxystyrene, 4-t-butoxystyrene, 2-chloromethylstyrene, 3-chloromethylstyrene, 4-chloromethylstyrene, 2-chlorostyrene, 3-chlorostyrene, 4-chlorostyrene, 2-bromostyrene, 3-bromostyrene, 4-bromostyrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 4-t-butylstyrene; ethylene, butadiene, propylene; vinyl chloride, vinylidene chloride; vinyl acetate; acrylonitrile; N-vinylpyrrolidone; acrylic acid, methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, t-butyl acrylate, hexyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, nonyl acrylate, benzyl acrylate, lauryl acrylate, n-octyl acrylate, 2-methoxyethyl acrylate, butoxyethyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-(diethylamino)ethyl acrylate, furfuryl acrylate, glycidyl acrylate; acrylamide, N,N-dimethylacrylamide; methacrylic acid, methyl methacrylate, ethyl methacrylate, allyl methacrylate, propyl methacrylate, n-butyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, nonyl methacrylate, benzyl methacrylate, cyclohexyl methacrylate, lauryl methacrylate, n-octyl methacrylate, 2-methoxyethyl methacrylate, butoxyethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-(diethylamino)ethyl methacrylate, furfuryl methacrylate, glycidyl methacrylate; methacrylamide; and the like, but are not limited thereto. The copolymer may be a copolymer with (meth)acrylic acid, (meth)acrylic acid ester or (meth)acrylate.

[0140] The present disclosure provides a method for manufacturing a monomer. Examples of the manufacturing method are listed below, but are not limited thereto.

[0141] (Method for manufacturing the compound of the present disclosure) (Method 1) A phosphorus-containing compound having one P-H bond (R 1 R 2 P(=O)H) is reacted with an aldehyde or a ketone (R 3 C(=O)R 4 ) to obtain an intermediate compound of R 1 R 2 P(=O)-CR 3 R 4 -OH.

[0142]

Chemical formula

[0143] Here, R 1 and R 2 are each independently aryl, and R 3 and R 4 are each independently hydrogen or a substituted or unsubstituted alkyl group.

[0144] This reaction can be carried out by heating a diarylphosphine oxide and an aldehyde or a ketone in a solvent.

[0145] Examples of the aldehyde that can be used in this reaction include formaldehyde (methanal), acetaldehyde (ethanal), propionaldehyde (propanal), butanal, pentanal, hexanal, heptanal, octanal, nonanal, decanal, etc. Paraformaldehyde can be used as the formaldehyde.

[0146] Examples of the ketone that can be used in this reaction include acetone, methyl ethyl ketone, diethyl ketone, methyl propyl ketone, methyl isobutyl ketone, methyl amyl ketone, etc.

[0147] Examples of the solvent used in this reaction include methanol, ethanol, acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, dimethylacetamide, and the like.

[0148] When the above intermediate compound is reacted with (meth)acrylic acid chloride in a solvent in the presence of a base, a phosphorus-containing (meth)acrylic acid ester derivative can be obtained.

[0149] [Chemical formula]

[0150] Examples of the solvent used in this reaction include ethyl acetate, butyl acetate, diethyl ether, tetrahydrofuran, dioxane, dichloromethane, dimethylformamide, dimethylacetamide, and the like. Acrylic acid chloride and methacrylic acid chloride, etc. can be used. Examples of the base that can be used include potassium carbonate, sodium carbonate, sodium hydrogen carbonate, cesium carbonate, trimethylamine, triethylamine, and the like.

[0151] Even when the above intermediate compound is reacted with (meth)acrylic acid in a solvent, a phosphorus-containing (meth)acrylic acid ester derivative can be obtained.

[0152] [Chemical formula]

[0153] Examples of the solvent used in this reaction include chloroform, dichloromethane, 1,2-dichloroethane (EDC), diethyl ether, THF, dioxane, and the like. Acrylic acid and methacrylic acid, etc. can be used.

[0154] (Method 2) A phosphorus-containing compound having one P-H bond (R1 R 2 Reacting P(=O)H) with an epoxide (oxirane)

[0155]

Chemical formula

[0156] results in the formation of an intermediate compound of R 1 R 2 P(=O)-CH2-CHR 3 -OH.

[0157]

Chemical formula

[0158] Here, R 1 and R 2 are each independently aryl, and R 3 is hydrogen, or a substituted or unsubstituted alkyl group.

[0159] Reacting this intermediate compound with (meth)acrylic acid chloride in the presence of a base gives a phosphorus-containing (meth)acrylate derivative

[0160]

Chemical formula

[0161] is obtained.

[0162] Reacting the above intermediate compound with (meth)acrylic acid in a solvent also gives a phosphorus-containing (meth)acrylate derivative.

[0163]

Chemical formula

[0164] Examples of the solvent used in this reaction include chloroform, dichloromethane, 1,2-dichloroethane (EDC), diethyl ether, THF, dioxane, etc. Acrylic acid, methacrylic acid, etc. can be used.

[0165] (Synthesis of a diarylphosphine oxide derivative containing a group having an epoxy group) A diarylphosphine oxide derivative containing a group having an epoxy group can be produced by mixing a diarylphosphine oxide and a compound having an epoxy group with an unsaturated double bond in a solvent, adding a radical initiator, and heating.

[0166] [Chemical formula]

[0167] (where n2' = n2 - 2) Examples of the radical initiator can be the same as those used in the method for producing a polymer. Examples of the polymerization initiator include azo compound-based thermal polymerization initiators such as azoisobutyronitrile (AIBN), azobisdimethylvaleronitrile (ADVN), azobis(methylbutyronitrile) (AMBN), etc., and organic peroxide-based thermal polymerization initiators such as dibenzoyl peroxide (BPO), t-butyl hydroperoxide (TBHP), cumene hydroperoxide, di-t-butyl hydroperoxide, etc.

[0168] Examples of the reaction solvent include methanol, ethanol, acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, dimethylacetamide, ethyl acetate, butyl acetate, etc.

[0169] (Synthesis of a diarylphosphine oxide derivative containing a dihydroxy-substituted aryl group) A diarylphosphine oxide derivative containing a dihydroxy-substituted aryl group can be produced by dissolving diarylphosphine oxide in a solvent, dropping a benzoquinone derivative dissolved in the solvent, and heating and aging the mixture.

[0170]

Chemical formula

[0171] (In the formula, R x and R y are each an arbitrary substituent or can form a ring together) Examples of the reaction solvent include methanol, ethanol, acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, dimethylacetamide, ethyl acetate, butyl acetate, etc.

[0172] (Synthesis of diphosphine compound) It can be produced by dissolving a diarylphosphine oxide derivative in a solvent, adding a base and stirring, and dropping a dihalo compound.

[0173]

Chemical formula

[0174] (In the formula, X is a halogen) Examples of the usable base include alkali metals (lithium, sodium, potassium), alkyl metals (alkyl lithium, alkyl sodium, alkyl potassium), alkoxy alkali metals (lithium alkoxide, sodium alkoxide, potassium alkoxide), alkali metal hydroxides (lithium hydroxide, sodium hydroxide, potassium hydroxide), alkali metal hydrides (lithium hydride, sodium hydride, potassium hydride), etc.

[0175] Examples of the reaction solvent include methanol, ethanol, acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, dimethylacetamide, ethyl acetate, butyl acetate and the like.

[0176] Examples of the dihalo compound include dichloroethane, dibromoethane, diiodoethane, α,α'-dichloro-para-xylene, α,α'-dibromo-para-xylene, α,α'-diiodo-para-xylene.

[0177] (Method for producing polymer) The polymers of the present disclosure can be obtained by polymerizing the compounds of the present disclosure. The polymerization may be homopolymerization or copolymerization. The polymerization of compounds having an acrylic group or a methacrylic group can be carried out by radical polymerization. Examples of the polymerization initiator include azo compound-based thermal polymerization initiators such as azoisobutyronitrile (AIBN), azobisdimethylvaleronitrile (ADVN), azobis(methylbutyronitrile) (AMBN), etc., and organic peroxide-based thermal polymerization initiators such as dibenzoyl peroxide (BPO), t-butyl hydroperoxide (TBHP), cumene hydroperoxide, di-t-butyl hydroperoxide, etc. The polymerization of compounds having an epoxy group can be carried out by anionic polymerization or cationic polymerization. Examples of the initiator for anionic polymerization include various alkyl metal compounds (e.g., methyl lithium, n-butyl lithium, t-butyl lithium, methyl magnesium chloride, methyl magnesium bromide, butyl magnesium chloride, butyl magnesium bromide), various alkoxy metal compounds (e.g., sodium methoxide, sodium ethoxide, potassium t-butoxide), various aryl metal compounds (e.g., phenyl lithium, phenyl sodium, phenyl magnesium chloride, phenyl magnesium bromide), various amine-based curing agents (e.g., aliphatic amines such as diethylenetetramine, triethylenetetramine, m-xylenediamine, aromatic amines such as diaminophenylmethane, m-phenylenediamine, trimethylenebis(4-aminobenzoate)), various phenol-based curing agents (e.g., bisphenol A, bisphenol F, 4,4-dihydroxydiphenylmethane), various thiol-based curing agents (e.g., 1,4-butanedithiol, 1,6-hexanedithiol), etc.Examples of cationic polymerization initiators include various Bronsted acids (e.g., sulfuric acid, perchloric acid, trifluoromethanesulfonic acid), Lewis acids (e.g., aluminum trichloride, boron trifluoride, titanium tetrachloride, tin tetrachloride), and thermal cationic polymerization initiators such as sulfonium salts (e.g., (2-ethoxy-1-methyl-2-oxoethyl)methyl-2-naphthylsulfonium hexafluoroantimonate, 4-(methoxycarbonyloxy)phenylbenzylmethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium hexafluoroantimonate), phosphonium salts (ethyltriphenylphosphonium hexafluoroantimonate, tetrabutylphosphonium hexafluoroantimonate), etc.

[0178] In the present disclosure, a polymer containing the following derived from an acrylate compound as a constituent can be produced.

[0179] [Chemical formula]

[0180] (A) The present disclosure also provides a copolymer of an acrylate compound and methyl acrylate, methyl methacrylate, styrene, and acrylonitrile.

[0181] In the present disclosure, a polymer containing the following derived from a compound having an epoxy group as a constituent can be produced.

[0182] [Chemical formula]

[0183] The present disclosure also provides a copolymer with an epoxy compound.

[0184] (Use) In one aspect, the present disclosure provides an additive comprising the compound of the present disclosure or a salt thereof, or a homopolymer or copolymer of the present disclosure. The uses of the additive include any of those described herein.

[0185] The present disclosure provides an article comprising the compound of the present disclosure or a salt thereof, or a homopolymer or copolymer of the present disclosure. Such articles include anti-fogging agents, flame retardants, electrical / electronic related parts, OA related parts, automotive parts, train parts, aircraft parts or fibers, sheets, films, or acrylic glass, polymerization additives, surface modifiers.

[0186] The homopolymer or copolymer of the present disclosure has low water absorption and is useful as an anti-fogging agent. The compound of the present disclosure or a salt thereof can also be used as an anti-fogging agent. When the compound of the present disclosure or a salt thereof is a solid (preferably a powder), it is easy to handle and can be easily used in an appropriate amount. It can reduce waste more than when it is a liquid.

[0187] The compound of the present disclosure or a salt thereof, or the homopolymer or copolymer of the present disclosure contains phosphorus and may be useful as a flame retardant. When the compound of the present disclosure or a salt thereof is a solid (preferably a powder), it is easy to handle and can be easily used in an appropriate amount. It can reduce waste more than when it is a liquid.

[0188] The homopolymer or copolymer of the present disclosure is flame retardant and is useful in electrical / electronic related parts, OA related parts, automotive parts, train parts, aircraft parts or fibers, etc.

[0189] The homopolymer or copolymer of the present disclosure is easy to mold and has transparency, so it can be used as a sheet, film, or acrylic glass.

[0190] The compounds of the present disclosure or salts thereof are polymerizable and can change the properties of the polymers produced as polymerization additives. When the compounds of the present disclosure or salts thereof are solids (preferably powders), they are easy to handle and can be easily used in appropriate amounts. Less waste can be generated compared to when they are liquids.

[0191] The compounds of the present disclosure or salts thereof can bind to the surface of an object and can change the properties of the surface as a surface modifier. When the compounds of the present disclosure or salts thereof are solids (preferably powders), they are easy to handle and can be easily used in appropriate amounts. Less waste can be generated compared to when they are liquids.

[0192] In one aspect, the present disclosure provides a phosphorus-imparting agent containing the compounds of the present disclosure or salts thereof. The phosphorus-imparting agent of the present disclosure can be used in the production of fertilizers, agricultural chemicals, pharmaceuticals, insecticides, gunpowders, electronic materials, catalysts, flame retardants, metal surface treatment agents, detergents, antifreeze liquids, surfactants, defoaming agents, and lubricants. When the compounds of the present disclosure or salts thereof are solids (preferably powders), they are easy to handle and can be easily used in appropriate amounts. Less waste can be generated compared to when they are liquids.

[0193] The compounds of the present disclosure or salts thereof contain a (meth)acrylic acid moiety that can easily undergo radical polymerization and can easily impart phosphorus to other substances. The target to which phosphorus is imparted may be any one that can react with the radicals generated in the (meth)acrylic acid moiety. The compounds of the present disclosure or salts thereof have the effect of reducing the water absorption rate and also help to produce compounds with low water absorption. When the compounds of the present disclosure or salts thereof are solids (preferably powders), they are easy to handle and can be easily used in appropriate amounts. Less waste can be generated compared to when they are liquids.

[0194] In one aspect, the present disclosure provides a surface treatment method using the compounds or salts thereof of the present disclosure. This surface treatment method can reduce the water absorption of the surface. The method may include a step of polymerizing the compound or salt represented by the general formula (I) on the surface. The surface may be resin or glass. When the compound or salt thereof of the present disclosure is solid (preferably powder), it is easy to handle and can be easily used in an appropriate amount. It can reduce waste more than when it is liquid.

[0195] References such as scientific literature, patents, patent applications, etc., cited in this specification are hereby incorporated by reference in this specification to the same extent as if each were specifically set forth herein.

[0196] As described above, the present disclosure has been described with reference to preferred embodiments for ease of understanding. Hereinafter, the present disclosure will be described based on examples. However, the above description and the following examples are provided for illustrative purposes only and are not provided for the purpose of limiting the present disclosure. Therefore, the scope of the present disclosure is not limited to the embodiments or examples specifically described herein, but is limited only by the claims.

Examples

[0197] The present disclosure will be described more specifically according to the following examples and comparative examples. However, the present disclosure is not construed as being limited thereto, and examples obtained by appropriately combining the technical means disclosed in each example are also included in the scope of the present disclosure.

[0198] Also, the abbreviations used in this specification have the following meanings. AN: Acrylonitrile GC-MS: Gas Chromatograph-Mass Spectrometer MA: Methyl Acrylate Mes: 2,4,6-Trimethylphenyl MMA: Methyl Methacrylate NMR: Nuclear Magnetic Resonance PMA: Poly(methyl acrylate) Ph: Phenyl rt: Room temperature (e.g., 15°C to 25°C) St: Styrene THF: Tetrahydrofuran The compounds of the present disclosure and their synthesis are further described by the following examples. The following examples are provided to further define the present disclosure, but the present disclosure is not limited to the features of these examples. In certain examples, common names are used, and it is understood that these common names are recognized by those skilled in the art.

[0199] Proton nuclear magnetic resonance ( 1 H NMR) spectra were recorded using deuterated chloroform as the measurement solvent on a JEOL JNM-ECX FT NMR system or a JEOL JNM-ECS FT NMR system (400 MHz). Phosphorus nuclear magnetic resonance ( 31 P NMR) spectra were recorded using deuterated chloroform, deuterated dimethyl sulfoxide, deuterated methanol, and deuterated trifluoroacetic acid as the measurement solvents on a JEOL JNM-ECX FT NMR system or a JEOL JNM-ECS FT NMR system (162 MHz). Chemical shifts were indicated in parts per million (ppm), and the residual solvent signal was used as the reference. The following abbreviations for NMR were used: s = singlet, d = doublet, dd = double doublet, m = multiplet.

[0200] GC spectra and GC-MS spectra were obtained using a Varian 220-MS with an initial temperature of 50°C, a hold time of 2 minutes, a heating rate of 20°C / min, a final temperature of 250°C, a hold time of 10 minutes, column flow pressure control (22.3 psi), and a column from Agilent Technologies, DB-5 (length 30 m, inner diameter 0.25 mm, film thickness 0.25 μm). Measurements were performed by the EI method.

[0201] Gel permeation chromatography (GPC) was performed using a Tosoh HLC-8320GPC with a column: TSK gel Super AW2500 6.0×150.

[0202] The dielectric constant was measured using the Toyo Technica Dielectric Constant Measurement System WKR6510P at a measurement frequency of 1 MHz and a measurement temperature of 25 °C.

[0203] For the solvent, other general solvents were of first grade manufactured by Sigma-Aldrich Japan.

[0204] (Example 1)

[0205] [Chemical formula]

[0206] 46.1 g of di-o-tolylphosphine oxide, 7.2 g of paraformaldehyde, and 230.2 g of toluene were added to a 500 mL four-necked flask and heated and stirred at 60 o °C for 3 hours. After allowing the reaction solution to cool to room temperature, the precipitate obtained was collected by filtration and dried to obtain 43.7 g of white crystals. 39.0 g of the white crystals obtained, 156.2 g of toluene, and 16.7 g of triethylamine were added to a 500 mL four-necked flask and heated to 40 o °C. 11.5 g of methacrylic acid chloride was added dropwise over 20 minutes and reacted at 50 o °C for 3 hours. After cooling the reaction solution to room temperature, 100 mL of 1N aqueous sodium hydroxide solution was added and stirred for about 10 minutes. The organic layer was transferred to a separatory funnel and washed with 100 mL of purified water, and the organic layer was dried over magnesium sulfate. The magnesium sulfate was filtered off, and the organic layer was concentrated to obtain 32.2 g of a light brown solid (Figure 1). GC-MS: 329 [M+H], 298, 229, 91 31 P NMR (NONE, 161 MHz) = δ28.3 (Example 2)

[0207] [Chemical formula]

[0208] 57.3 g of dimethylphenylphosphine oxide, 7.2 g of paraformaldehyde, and 286 g of toluene were added to a 500 mL four-necked flask and heated with stirring at 60 o °C for 3 hours. After allowing the reaction solution to cool to room temperature, the precipitate obtained was collected by filtration and dried to obtain 54.0 g of white crystals. 47.4 g of the white crystals obtained, 190.0 g of toluene, and 16.7 g of triethylamine were added to a 500 mL four-necked flask and heated to 40 o °C. 11.5 g of methacrylic acid chloride was added dropwise over 20 minutes, and the mixture was reacted at 50 o °C for 3 hours. After cooling the reaction solution to room temperature, 100 mL of 1N aqueous sodium hydroxide solution was added and stirred for about 10 minutes. The organic layer was transferred to a separatory funnel, washed with 100 mL of purified water, and the organic layer was dried over magnesium sulfate. The magnesium sulfate was filtered off, and the organic layer was concentrated to obtain 40.4 g of a light brown solid (Figure 2). GC-MS: 385 [M+H], 370, 283 31 P NMR (NONE, 161 MHz) = δ 31.8 (Example 3)

[0209]

Chemical formula

[0210] 1.43 g of dimethylphenylphosphine oxide, 0.57 g of allyl glycidyl ether, and 13.0 g of toluene were added to a 100 mL three-necked flask. 1.64 g of azoisobutyronitrile (AIBN) was added and heated with stirring at 80 o °C for 3 hours. After allowing the reaction solution to cool to room temperature, it was concentrated and dried under vacuum to obtain 2.03 g of a colorless transparent viscous liquid. 31 P NMR (NONE, 161 MHz) = δ 29.3 (Example 4)

[0211]

Chemical formula

[0212] 28.6 g of dimesitylphosphine oxide and 57.3 g of toluene were added to a 300 mL four-necked flask and stirred at room temperature until completely dissolved. 10.8 g of p-benzoquinone and 108.1 g of toluene were added to a 300 mL beaker to completely dissolve p-benzoquinone. The toluene solution of p-benzoquinone was added to the 300 mL four-necked flask and stirred at 60 o C for 1 hour. After allowing the reaction solution to cool to room temperature, the precipitate obtained was collected by filtration and dried to obtain 32.1 g of a white powder. 31 P NMR (DMSO-d6, 161 MHz) = δ 35.3 (Example 5)

[0213] [Chemical formula]

[0214] 28.6 g of dimesitylphosphine oxide and 114.5 g of toluene were added to a 300 mL four-necked flask and stirred at room temperature until completely dissolved. 4.4 g of sodium hydroxide was added and stirred at room temperature for 1 hour. 4.95 g of dichloroethane (DCE) was added and stirred at 60 o C for 3 hours. After allowing the reaction solution to cool to room temperature, the precipitate obtained was collected by filtration and dried to obtain 18.3 g of a pale yellow powder. 31 P NMR (NONE, 161 MHz) = δ 26.5 (Example 6)

[0215] [Chemical formula]

[0216] 28.6 g of dimesitylphosphine oxide and 143.2 g of toluene were added to a 300 mL four-necked flask and stirred at room temperature until completely dissolved. 4.4 g of sodium hydroxide was added and stirred at room temperature for 1 hour. 8.8 g of α,α'-dichlorop-xylene was added and stirred at 60 oIt was stirred in C for 3 hours. After allowing the reaction solution to cool to room temperature, the precipitate obtained was collected by filtration and dried to obtain 25.3 g of a pale yellow powder. 31 P NMR (NONE, 161 MHz) = δ 68.4 (Example 7) 20.0 g of the light brown solid obtained in Example 2 was weighed into a 200 mL separable flask, 4 times the weight of 2-butanone was added, and it was stirred well. After degassing and nitrogen substitution, it was heated to 40 °C. After adding 0.20 g of benzoyl peroxide, the temperature inside the reaction vessel was raised to 80 °C and reacted for 20 hours. After completion of the reaction, the reaction solution was dropped into hexane to precipitate the produced polymer. The precipitated polymer was washed with ion-exchanged water and dried in a vacuum dryer to obtain 14.5 g of a white powder. The weight average molecular weight and dielectric constant of the obtained polymer were measured.

[0217] (Comparative Example 1) 20.0 g of Comparative Compound 1 was weighed into a 200 mL separable flask, 4 times the weight of 2-butanone was added, and it was stirred well. After degassing and nitrogen substitution, it 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 completion of the reaction, the reaction solution was dropped into hexane to precipitate the produced polymer. The precipitated polymer was washed with ion-exchanged water and dried in a vacuum dryer to obtain 16.3 g of a white powder. The weight average molecular weight and dielectric constant of the obtained polymer were measured.

[0218]

Chemical Structure

[0219] Comparative Compound 1

[0220]

Table 1

[0221] The polymer obtained from the compound of the present invention having a substituent on the aryl group has been shown to have a significantly lower dielectric constant (Dk) and dielectric tangent (Df) compared to the polymer obtained from the compound of Comparative Example 1 having no substituent on the aryl group.

[0222] As described above, the present disclosure has been illustrated using preferred embodiments of the present disclosure. However, it is understood that the scope of the present disclosure should be construed only by the claims. This application claims priority to Japanese Patent Application No. 2020-130769 (filed on July 31, 2020), the entire content of which is incorporated herein by reference in its entirety. It is understood that patents, patent applications, and other documents cited herein should be incorporated by reference in their entirety as if the content thereof were specifically set forth herein. It is understood that patents, patent applications, and other documents cited herein should be incorporated by reference in their entirety as if the content thereof were specifically set forth herein.

Industrial Applicability

[0223] The novel phosphorus compound can be used in various applications. For example, it can be used in anti-fogging agents, flame retardants, parts for electric / electronic applications, parts for OA-related applications, parts for automobiles, parts for trains, parts for aircraft, or fibers, sheets, films, or acrylic glass, polymerization additives, etc. It can also be used as a phosphorus-imparting agent.

Claims

1. A phosphine oxide compound represented by the following general formula (I) or a salt thereof, [Chemical Formula 4] wherein, in the formula, R １ and R ２ are different or the same and are each independently an aryl group having a substituent, and the aryl groups in R １ and R ２ each independently have one, two or three substituents, R ３ and R ４ are each independently hydrogen, a substituted or unsubstituted alkyl group, n is 1 or 2, Here, when n is 2, each R ３ may be the same or different from each other, and each R ４ may be the same or different from each other, R ５ is hydrogen, or a substituted or unsubstituted alkyl group, a phosphine oxide compound or a salt thereof.

2. R １ and R ２ The phosphine oxide compound or a salt thereof according to claim 1, wherein the aryl group in R and R each has one substituent.

3. R １ and R ２ The phosphine oxide compound or a salt thereof according to claim 1, wherein the aryl group in

4. R １ and R ２ The phosphine oxide compound or a salt thereof according to claim 1, wherein the aryl group in R and R each has three substituents.

5. R １ and R ２ wherein the substituent on the aryl group is halogen, alkyl, —Oalkyl, —OH, —NO ２ , -NH ２ 5. The compound or salt thereof according to any one of claims 1 to 4, wherein the alkyl is selected from the group consisting of -C(=O)H, -C(=O)alkyl, and -C(=O)Oalkyl, wherein the alkyl is substituted or unsubstituted.

6. R １ and R ２ wherein the substituent on the aryl group in R is selected from the group consisting of halogen, -C1-C4 alkyl, -OC1-C4 alkyl, -OH, -NO ２ , -NH ２ , -C(=O)H, -C(=O)C1-C4 alkyl, and -C(=O)OC1-C4 alkyl, and the alkyl is substituted or unsubstituted, the compound or a salt thereof according to any one of claims 1 to 5.

7. R １ and R ２ In R and R, the phosphine oxide compound or a salt thereof according to any one of claims 1 to 6, wherein the substituents are each independently a C1 to C4 alkyl group.

8. R １ and R ２ In R and R, the aryl group having the substituent is a monocyclic, bicyclic or tricyclic group having a substituent, the phosphine oxide compound or a salt thereof according to any one of claims 1 to 7.

9. R １ and R ２ In R and R, the phosphine oxide compound or a salt thereof according to any one of claims 1 to 8, wherein the aryl group having the substituent is a phenyl group having a substituent.

10. R １ and R ２ are 【Chemical 1】 where * indicates a bonding point, a phosphine oxide compound or a salt thereof according to any one of Claims 1 to 9, here, when the aryl groups in R1 and R2 each have one substituent, R1 and R2 are, 【Chemical 1A】 wherein, when the aryl groups in R1 and R2 each have two substituents, R1 and R2 are, 【Chemical Formula 1B】 wherein, when the aryl groups in R1 and R2 each have three substituents, R1 and R2 are, 【Chemical Formula 1C】 wherein, a phosphine oxide compound or a salt thereof.

11. R １ and R ２ The phosphine oxide compound or a salt thereof according to claim 1, wherein the substituent on the aryl group in R and R is a substituted or unsubstituted alkyl group.

12. A phosphine oxide compound represented by the following general formula (II) or a salt thereof, [Chemical Formula 5] wherein, R １ and R ２ are different or the same and each independently is an aryl group having a substituent, R ６ 、R ７ 、R ８ 、and R ９ is, independently of one another, hydrogen or a substituted or unsubstituted alkyl group, n １ and n ２ are each independently 1 to 3, Here, n １ is 2 or 3, each R ６ may be the same or different from each other, and each R ７ may be the same or different from each other, Here, n ２ is 2 or 3, each R ８ may be the same or different from each other, and each R ９ may be the same or different from each other. a phosphine oxide compound or a salt thereof.

13. R １ and R ２ The phosphine oxide compound or a salt thereof according to claim 12, wherein the aryl group in R and R each independently has one, two or three substituents.

14. R １ and R ２ The phosphine oxide compound or a salt thereof according to claim 13, wherein the substituent on the aryl group in R and R is a substituted or unsubstituted alkyl group.

15. The following general formula (III) [Chemical Formula 6] A phosphine oxide compound represented by the formula or a salt thereof, wherein R １ and R ２ are different or the same and each independently is an aryl group having a substituent, and the aryl groups in R １ and R ２ each independently have two or three substituents, a phosphine oxide compound or a salt thereof.

16. R １ and R ２ The phosphine oxide compound or a salt thereof according to claim 15, wherein the substituent on the aryl group in R

17. The following general formula (IV) (R １ )(R ２ )P(=O)-(Linker)-P(=O)(R １ )(R ２ ) (IV) A phosphine oxide compound represented by the formula or a salt thereof, R １ and R ２ are different or the same and each independently is an aryl group having three substituents, （１） wherein the linker is, -(Ar) ｎ５ - is n5 is 1 to 3, Ar is an unsubstituted arylene group or heteroarylene group, or （２） wherein the linker is, -(C(R10)(R11))n3-(Ar)n5-(C(R12)(R13))n4-, R10, R11, R12, and R13 are each independently selected from the group consisting of hydrogen, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted thioalkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted alkylcarbonyl group, and a substituted or unsubstituted aminocarbonyl group, Ar is a substituted or unsubstituted arylene group or heteroarylene group, n3, n4 and n5 are each independently 1 to 3, A phosphine oxide compound or a salt thereof.

18. R １ and R ２ The phosphine oxide compound or a salt thereof according to claim 17, wherein the substituent on the aryl group in R

19. The linker is 【Chemical Formula 7】 The compound or salt thereof according to claim 17, wherein the linker is

20. The following general formula (VI) 【Chemical formula 10】 (wherein, R １ and R ２ are each independently a substituted or unsubstituted aryl group, R ６ 、 R ７ 、 R ８ 、 and R ９ is, independently of one another, hydrogen or a substituted or unsubstituted alkyl group, n １ and n ２ is each independently 1 or 2, Here, n １ When it is 2, each R ６ may be the same or different from each other, and each R ７ may be the same or different from each other, Here, n ２ is 2, each R ８ may be the same or different from each other, and each R ９ may be the same or different from each other) is a homopolymer or copolymer containing as a constituent.

21. The copolymer according to claim 20, which is a copolymer with an epoxy compound.

22. An additive comprising the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21.

23. An anti-fogging agent comprising the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21.

24. A flame retardant comprising the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21.

25. Parts for electric / electronic applications, parts for OA-related applications, parts for automobiles, parts for trains, parts for aircraft or fibers, comprising the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21.

26. A sheet, film, or acrylic glass comprising the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21.

27. A polymerization additive comprising the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21.

28. A surface modifier comprising the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21.

29. A phosphorus-imparting agent comprising the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21.

30. Use of the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21, in parts related to electric / electronic, OA-related, automotive, railway, aircraft, fiber, sheet, film, or acrylic glass, or use of the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21 as an additive, anti-fogging agent, flame retardant, polymerization additive, surface modifier or phosphorus-imparting agent.

31. A method of using the compound or salt according to any one of claims 1 to 19, or the homopolymer or copolymer according to claim 20 or 21, in parts related to electric / electronic, OA-related, automotive, railway, aircraft, fiber, sheet, film, or acrylic glass, or as an additive, anti-fogging agent, flame retardant, polymerization additive, surface modifier or phosphorus-imparting agent, the method comprising the step of applying the compound or salt, or the homopolymer or copolymer, to an object in need thereof.

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