JP7714236B2 - Diarylphosphine oxide derivatives - Google Patents

Description

The present disclosure relates to diarylphosphine oxide derivatives.

Phosphorus compounds are used in a variety of applications due to their properties. It would be beneficial to provide novel phosphorus-containing compounds.

International Publication No. 2018/124205 JP 2017-132731 A

After extensive research, the inventors have synthesized novel diarylphosphine oxide derivative compounds that are believed to be highly useful, and provide the present disclosure.

The present disclosure provides a method for synthesizing diarylphosphine oxide derivatives, which have previously been considered difficult.

The present disclosure also provides the following:
(Item 1)
The following general formula R _a -P(═O)R ¹ R ²
or a salt thereof,
During the ceremony,
R ¹ and R ² are different or the same and each independently represent a substituted aryl group;
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;
A phosphine oxide compound or a salt thereof.
(Item 2)
Item 2. The phosphine oxide compound or a salt thereof according to item 1, wherein the aryl groups in R ¹ and R ² each independently have one, two or three substituents.
(Item 3)
Item 2. The phosphine oxide compound or a salt thereof according to item 1, wherein the aryl groups in R ¹ and R ² each have one substituent.
(Item 4)
Item 2. The phosphine oxide compound or a salt thereof according to item 1, wherein the aryl group in R ¹ and R ² each has two substituents.
(Item 5)
Item 2. The phosphine oxide compound or a salt thereof according to item 1, wherein the aryl group in R ¹ and R ² each has three substituents.
(Item 6)
6. The compound or salt thereof according to any one of items 1 to 5, wherein the substituents on the aryl group in R ¹ and R ² are selected from the group consisting of halogen, alkyl, —Oalkyl, —OH, —NO ₂ , —NH ₂ , —C(═O)H, —C(═O)alkyl, and —C(═O)Oalkyl, and the alkyl is substituted or unsubstituted.
(Item 7)
7. The compound or salt thereof according to any one of items 1 to 6, wherein the substituents on the aryl group in R ¹ and R ² are 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, wherein the alkyl is substituted or unsubstituted.
(Item 8)
8. The phosphine oxide compound or a salt thereof according to any one of items 1 to 7, wherein in R ¹ and R ² , the substituents are each independently a —C1 to C4 alkyl group.
(Item 9)
9. The phosphine oxide compound or a salt thereof according to any one of items 1 to 8, wherein in R ¹ and R ² , the aryl group having a substituent is a monocyclic, bicyclic, or tricyclic ring having a substituent.
(Item 10)
Item 10. The phosphine oxide compound or a salt thereof according to any one of items 1 to 9, wherein in R ¹ and R ² , the aryl group having a substituent is a phenyl group having a substituent.
(Item 11)
^R1 and ^R2 are

11. The phosphine oxide compound or a salt thereof according to any one of items 1 to 10, wherein * indicates a point of attachment.
(Item 12)
12. The phosphine oxide compound or salt thereof according to any one of items 1 to 11, wherein R ^a is a group having an unsaturated double bond at a terminal, a group having an epoxy group at a terminal, an aryl group having two or more hydroxyl groups, or a group containing a phosphine oxide.
(Item 13)
R _a is

,

or a dihydroxy-substituted aryl group;
^R3 and ^R4 are each independently hydrogen or a substituted or unsubstituted alkyl group;
n is 1 or 2;
wherein when n is 2, each ^R3 may be the same or different, and each ^R4 may be the same or different;
^R5 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 each independently represent 1 to 3;
wherein when _n1 is 2 or 3, each ^R6 may be the same or different, and each ^R7 may be the same or different;
wherein when _n2 is 2 or 3, each ^R8 may be the same or different, and each ^R9 may be the same or different;
* indicates the point of attachment
13. The phosphine oxide compound or a salt thereof according to any one of items 1 to 12.
(Item 14)
Item 14. The phosphine oxide compound or a salt thereof according to any one of items 1 to 13, wherein R _a is an acryloyloxymethyl group, a methacryloyloxymethyl group, an epoxymethyloxypropyl group, or a 2,5-dihydroxyphenyl group.
(Item 15)
The phosphine oxide compound is represented by the following general formula (I):

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

(II)
wherein R ¹ and R ² are as defined in item 1, and R ⁶ , R ⁷ , R ⁸ , R ⁹ , n ₁ and n ₂ are as defined in item 13, or a salt thereof.
(Item 19)
Item 19. The phosphine oxide compound or a salt thereof according to item 18, wherein the aryl groups in R ¹ and R ² each independently have one, two or three substituents.
(Item 20)
Item 20. The phosphine oxide compound or salt thereof according to Item 19, wherein the substituents on the aryl group in R ¹ and R ² are substituted or unsubstituted alkyl.
(Item 21)
The phosphine oxide compound is represented by the following general formula (III):

(III)
and R ¹ and R ² are as defined in item 1, or a salt thereof.
(Item 22)
22. The phosphine oxide compound or a salt thereof according to item 21, wherein the aryl groups in R ¹ and R ² each independently have two or three substituents.
(Item 23)
Item 23. The phosphine oxide compound or salt thereof according to Item 22, wherein the substituents on the aryl group in R ¹ and R ² are 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)
is shown by
Item 2. The compound or salt thereof according to item 1, wherein R ¹ and R ² are as defined 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 or heteroarylene group;
n ₃ , n ₄ and n ₅ each independently represent an integer of 0 to 3;
25. The compound or salt thereof according to item 24.
(Item 26)
26. The compound or salt thereof according to item 25, wherein the aryl groups in ^R1 and ^R2 each independently have three substituents, _n3 and _n4 are 0, _n5 is 1 to 3, and Ar is an unsubstituted arylene group or heteroarylene group.
(Item 27)
27. The phosphine oxide compound or salt thereof according to item 26, wherein the substituents on the aryl group in R ¹ and R ² are substituted or unsubstituted alkyl.
(Item 28)
28. The compound or salt thereof according to item 27, wherein the aryl group in R ¹ and R ² each independently has a substituted or unsubstituted alkyl group, and n ₃ , n ₄ and n ₅ each independently represent 1 to 3.
(Item 29)
The linker is

29. The compound according to item 28, or a salt thereof, wherein
(Item 30)
The phosphine oxide compound is represented by the following general formula (IVa):

(IVa)
is shown 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;
25. The compound or salt thereof according to item 24.
(Item 31)
Item 31. The phosphine oxide compound or a salt thereof according to Item 30, wherein the aryl groups in R ¹ and R ² each independently have three substituents.
(Item 32)
Item 32. The phosphine oxide compound or salt thereof according to Item 31, wherein the substituents on the aryl group in R ¹ and R ² are substituted or unsubstituted alkyl.
(Item 33)
The following general formula (V)

(V)
(In the formula,
R ¹ and R ² are each independently a substituted or unsubstituted aryl group;
^R3 and ^R4 are each independently hydrogen or a substituted or unsubstituted alkyl group;
n is 1 or 2;
wherein when n is 2, each ^R3 may be the same or different, and each ^R4 may be the same or different;
^R5 is hydrogen or a substituted or unsubstituted alkyl group).
(Item 34)
34. The copolymer according to claim 33, which is a copolymer with (meth)acrylic acid, a (meth)acrylic acid ester, a (meth)acrylic acid halide, a (meth)acrylate, styrene or acrylonitrile.
(Item 35)
The following general formula (VI)

(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;
where _n1 is 2, each ^R6 may be the same or different, and each ^R7 may be the same or different;
wherein when _n2 is 2, each ^R8 may be the same or different, and each ^R9 may be the same or different) as a constituent.
(Item 36)
36. The copolymer according to item 35, which is a copolymer with an epoxy compound.
(Item 37)
An additive comprising 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 comprising 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 comprising 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)
An electric/electronic part, an office automation part, an automobile part, a train part, an aircraft part, or a fiber, comprising 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)
37. A sheet, film, or acrylic glass comprising 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 comprising 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 comprising 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-donating agent comprising 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 parts, office automation parts, automobile parts, train 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-providing agent.
(Item 46)
A method for 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 an electric/electronic part, an office automation part, an automobile part, a train part, an aircraft part, a fiber, a sheet, a film, or acrylic glass, or for using it as an additive, an anti-fogging agent, a flame retardant, a polymerization additive, a surface modifier, or a phosphorus-providing agent, the method comprising the step of applying the compound or salt, or the homopolymer or copolymer to an object in need thereof.

It is contemplated that one or more of the features described above may be provided in combinations other than 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.

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 in a variety of applications. By introducing a sterically hindering substituent, such as a methyl group, into the aryl group of the diarylphosphine oxide derivative disclosed herein, the swinging of the aryl group is suppressed, reducing loss and resulting in a resin with lower dielectric constant (Dk) and dielectric dissipation factor (Df) and high insulation properties.

FIG. 1 shows the GC-MS results of the product of Example 1. FIG. 2 shows the GC-MS results of the product of Example 2.

The present disclosure will now be described, illustrating the best mode thereof. Throughout this specification, singular terms should be understood to include the plural, unless otherwise specified. Thus, singular articles (e.g., "a," "an," "the," etc. in English) should be understood to include the plural, unless otherwise specified. Additionally, terms used in this specification should be understood to have the meaning commonly used in the art, unless otherwise specified. Therefore, unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. In the case of conflict, the present specification (including definitions) will control.

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

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

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

Unless otherwise specified, in this specification, 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. Removing one hydrogen atom can result in a monovalent substituent or combining it with a single bond to form a double bond, and removing two hydrogen atoms can result in a divalent substituent or combining it with a single bond to form a triple bond.

Substituents in the present disclosure include, but are not limited to, hydrogen, halogen, alkyl, alkoxy, —OH, —NO ₂ , —NH ₂ , —C(═O)H, alkylcarbonyl, and alkoxycarbonyl groups. Preferred groups of substituents in the present disclosure include halogen, alkyl, —Oalkyl, —OH, —NO ₂ , —NH ₂ , —C(═O)H, —C(═O)alkyl, and —C(═O)Oalkyl. Further preferred groups of substituents in the present disclosure include halogen, —C1-C4 alkyl (e.g., —CH ₃ ), —OC1-C4 alkyl (e.g., —OCH ₃ ), —OH, —NO ₂ , —NH ₂ , —C(═O)H, —C(═O)C1-C4 alkyl (e.g., —C(═O)CH ₃ ), and —C(═O)OC1-C4 alkyl. All of the substituents may have substituents other than hydrogen.

In this specification, C1, C2, ..., Cn represent the number of carbon atoms (where n is any positive integer). Therefore, C1 is used to represent a substituent with one carbon atom.

As used herein, "alkyl" refers to a monovalent group formed by the loss of a 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). An alkyl may be linear or branched. As used herein, "substituted alkyl" refers to an alkyl in which the H of the alkyl is replaced by a substituent as defined above. Specific examples of these 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 (CH ₃ —), ethyl (C ₂ H ₅ —), n-propyl (CH ₃ CH ₂ CH ₂ —), isopropyl ((CH ₃ ) ₂ CH—), n-butyl (CH ₃ CH ₂ CH ₂ CH ₂ —), n-pentyl (CH ₃ CH ₂ CH ₂ CH ₂ CH ₂ —), n-hexyl (CH ₃ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ —), n-heptyl (CH ₃ CH ₂ CH ₂ CH 2 CH ₂ CH ₂ CH _{2 —} ), n-octyl (CH ₃ CH _{2 CH 2} CH ₂ CH ₂ CH ₂ CH ₂ CH _{2 —} ), n-nonyl (CH _{Examples include 3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-} ) _, n-decyl ( _{CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2-), -C(CH3) 2CH2CH2CH2CH ( CH3 ) 2 , and -CH2CH(CH3)2 . Furthermore , for example , C1 - C10 substituted alkyl} refers to _a C1-C10 alkyl in which one _{or more} hydrogen atoms have been substituted with _a substituent.

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, and C3-C20 substituted cycloalkyl. Examples of cycloalkyl include cyclopropyl and cyclohexyl. A "substituted cycloalkyl group" refers to a cycloalkyl in which a hydrogen atom has been replaced.

As used herein, the term "alkoxy group" refers to a monovalent group formed by the loss of a hydrogen atom from a hydroxy group of an alcohol, and is generally represented by C _n H _2n+1 O- (where n is an integer of 1 or greater). The term "substituted alkoxy group" refers to an alkoxy in which the H of the alkoxy has been substituted with a substituent as defined above. Specific examples include C1 to C2 alkoxy, C1 to C3 alkoxy, C1 to C4 alkoxy, C1 to C5 alkoxy, C1 to C6 alkoxy, C1 to C7 alkoxy, C1 to C8 alkoxy, C1 to C9 alkoxy, C1 to C10 alkoxy, C1 to C11 alkoxy, C1 to C20 alkoxy, C1 to C2 substituted alkoxy, C1 to C3 substituted alkoxy, C1 to C4 substituted alkoxy, C1 to C5 substituted alkoxy, C1 to C6 substituted alkoxy, C1 to C7 substituted alkoxy, C1 to C8 substituted alkoxy, C1 to C9 substituted alkoxy, C1 to C10 substituted alkoxy, C1 to C11 substituted alkoxy, or C1 to C20 substituted alkoxy. Here, for example, C1-C10 alkoxy means a straight-chain or branched alkoxy containing 1 to 10 carbon atoms, and examples include methoxy (CH ₃ O—), ethoxy (C ₂ H ₅ O—), and n-propoxy (CH ₃ CH ₂ CH ₂ O—).

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

As used herein, the term "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, and may be the same or different, and may contain one or more heteroatoms. Heterocyclic groups may be aromatic or non-aromatic, and may be monocyclic or polycyclic. Heterocyclic groups may be substituted. A "substituted heterocyclic group" refers to a heterocyclic group in which a hydrogen atom has been substituted.

As used herein, the term "aryl group" refers to a group generated by removing one hydrogen atom bonded to an aromatic hydrocarbon ring. A phenyl group (C ₆ H ₅ -) is derived from benzene, a tolyl group (CH ₃ C ₆ H ₄ -) from toluene, a xylyl group ((CH ₃ ) ₂ C ₆ H ₃ -) from xylene, and a naphthyl group (C ₁₀ H ₈ -) from naphthalene. Examples of aryl groups include those having 6 to 12 carbon atoms. Aryl groups include monocyclic (phenyl group), bicyclic (naphthyl group), and tricyclic (anthracenyl group, etc.) rings.

As used herein, the term "heteroaryl group" refers to a group in which one or more carbon atoms constituting an aromatic hydrocarbon ring have been replaced with a heteroatom. Examples include, but are not limited to, pyridine, pyrrole, thiophene, furan, imidazole, oxazole, thiazole, indole, quinoline, isoquinoline, quinoxaline, pyrazine, and benzimidazole.

As used herein, the term "aryloxy group" refers to a monovalent group generated by losing a hydrogen atom from a hydroxy group of an aryl group substituted with a hydroxy group, and examples thereof include, but are not limited to, C ₆ H ₅ O—, CH ₃ C ₆ H ₄ O—, (CH ₃ ) ₂ C ₆ H ₃ O—, and C ₁₀ H ₈ O—.

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

As used herein, an "alkoxycarbonyl group" refers to a group represented by -C(O)OR (where R is an alkyl group). A "substituted alkoxycarbonyl group" refers to an alkoxycarbonyl group in which a hydrogen atom has been substituted.

In this specification, "halogen (group)" refers to a monovalent group of elements such as chlorine (Cl), bromine (Br), and iodine (I) that belong to Group 17 of the periodic table (recent definitions call it Group 17).

As used herein, the term "alkylcarbonyl group" refers to a monovalent group formed by removing OH from a carboxylic acid. Representative examples of alkylcarbonyl groups include acetyl (CH ₃ CO—) and C ₂ H ₅ CO—. The alkyl portion may have 1 to 6 carbon atoms. The term "substituted alkylcarbonyl group" refers to a group in which the hydrogen atom of an acyl group has been substituted with a substituent as defined above.

As used herein, an "aminocarbonyl group" refers to a group in which the hydrogen atom of an ammonia or amine is replaced with an acid group (acyl group). A "substituted aminocarbonyl group" refers to a group in which the hydrogen atom on the nitrogen atom has been replaced. An aminocarbonyl group is also called an amide.

As used herein, the term "arylene group" refers to a group generated by removing two hydrogen atoms bonded to an aromatic hydrocarbon ring. A phenylene group (-C ₆ H ₄ -) is derived from benzene, a methylphenylene group (-CH ₃ C ₆ H ₃ -) from toluene, a dimethylphenylene group (-(CH ₃ ) ₂ C ₆ H ₃ -) from xylene, and a naphthylene group (-C ₁₀ H ₇ -) from naphthalene. Examples of such groups include those having 6 to 12 carbon atoms.

As used herein, the term "heteroarylene group" refers to a group in which one or more carbon atoms constituting an aromatic hydrocarbon ring have been replaced with a heteroatom and which has two attachment points. Examples include, but are not limited to, pyridinediyl, pyrrolediyl, thiophenediyl, furandiyl, imidazolediyl, oxazolediyl, thiazolediyl, indolediyl, quinolinediyl, isoquinolinediyl, quinoxalinediyl, pyrazinediyl, and benzimidazolediyl.

As used herein, a "group having an unsaturated double bond" refers to a group containing a carbon-carbon double bond such as an alkene, and examples include carbon-only groups such as ethylene and propylene, and groups containing a carboxylate group such as acrylic and methacrylic.

As used herein, the term "group having an epoxy group" refers to a group having an oxacyclopropane (oxirane) three-membered ring ether in its structural formula. Examples include epoxy groups, epoxymethyl groups, epoxyethyl groups, epoxypropyl groups, epoxymethyloxy groups, epoxyethyloxy groups, epoxypropyloxy groups, epoxymethyloxymethyl groups, epoxymethyloxyethyl groups, epoxymethyloxypropyl groups, epoxyethyloxymethyl groups, epoxyethyloxyethyl groups, epoxyethyloxypropyl groups, epoxypropyloxymethyl groups, epoxypropyloxyethyl groups, and epoxypropyloxypropyl groups.

As used herein, "epoxy compound" refers to a compound containing an epoxy group. It may contain groups such as those listed as "groups having an epoxy group."

As used herein, the term "hydroxyl-containing group" refers to any group that contains a hydroxyl group as a functional group. This includes groups that contain an OH group in an aromatic ring, such as phenol. Examples include hydroxyphenyl groups, dihydroxyphenyl groups, and trihydroxyphenyl groups.

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

As used herein, the term "linker" refers to a group that links two or more groups. A linker may be a group that does not react in the application in which it is used.

As used herein, the term "polymer" refers to a substance composed of molecules in which one or more types of atoms or atomic groups are structural units, and these units are repeatedly linked together in large numbers. The number of repeating structural units in these molecules is so large that certain physical properties of the substance do not change with the increase or decrease of one or more structural units. Examples of polymers include homopolymers and copolymers.

As used herein, the term "monomer" refers to a compound that can become a structural unit of the basic structure of a polymer through a polymerization reaction. A single type of monomer may produce multiple types of structural units. The monomers disclosed herein can also be bonded to other substances through radical polymerization.

In this specification, the term "homopolymer," also known as a single polymer, refers to a polymer obtained by polymerization using a single monomer.

As used herein, the term "copolymer," also referred to as a copolymer, refers to a polymer obtained by polymerization using multiple monomers. In a typical embodiment of the present disclosure, the copolymer 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)acrylic acid salts, styrene, and acrylonitrile.

In this specification, "polymerization" refers to a reaction in which a high molecular weight compound (polymer) is produced from a low molecular weight compound (monomer).

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

In this specification, "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.

As used herein, the term "base" refers to the Bronsted-Lowry definition, and refers to a substance that accepts a proton. "Base" includes salts of weak acids and alkali metals, such as alkali metal carbonates (e.g., K ₂ CO ₃ ).

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

In this specification, "(meth)acrylic acid" refers to acrylic acid, methacrylic acid, or both.

As used herein, "additive" refers to a substance that is added to any substance.

As used herein, the term "anti-fogging agent" refers to a substance that maintains the transparency of a material (e.g., polyacrylic acid), typically by making the surface of the material more hydrophobic.

As used herein, the term "phosphorus-donating agent" refers to a substance that donates a phosphorus component to a substance. This is typically achieved by attaching a phosphorus-containing group to the substance. A phosphorus-donating agent having a (meth)acrylic group can attach a phosphorus-containing group to a compound having a radically polymerizable group through radical polymerization. Phosphorus-donating agents can be used, for example, in the manufacture of fertilizers, pesticides, pharmaceuticals, insecticides, explosives, electronic materials, catalysts, flame retardants, metal surface treatment agents, detergents, antifreeze, surfactants, antifoaming agents, and lubricants.

As used herein, the term "radically polymerizable group" refers to any group that polymerizes via a radical reaction. Representative examples include, but are not limited to, groups having an unsaturated double bond at the terminal of a substituent. Examples of such radically polymerizable groups include, but are not limited to, allyl, substituted allyl, styrene, substituted styrene, acrylic, substituted acrylic, methacrylic, and substituted methacrylic.

The compounds of the present disclosure include salts. Examples include salts with alkali metals (such as lithium, sodium, or potassium), alkaline earth metals (such as calcium), magnesium, transition metals (such as zinc or 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). In particular, salts with hydrochloric acid, phosphoric acid, tartaric acid, or methanesulfonic acid are included. These salts can be formed by conventional methods.

The compounds disclosed herein are not limited to any particular isomer, but include all possible isomers (keto-enol isomers, imine-enamine isomers, diastereoisomers, optical isomers, and rotational isomers, etc.) and racemates.

One or more hydrogen, carbon or other atoms of the compounds of the present disclosure can be replaced with isotopes of hydrogen, carbon or other atoms.The compounds of the present disclosure include all radiolabeled compounds of the compounds of the present disclosure.Examples of isotopes that can be incorporated into the compounds of the present disclosure include hydrogen, carbon, nitrogen, oxygen, phosphorus, sulfur, fluorine, iodine and chlorine, such as ^2H , ^3H , ^11C , ^13C , ^14C , ^15N , ^18O , ^17O , ^31P , ^32P , ^35S , ^18F , ^123I and ^36Cl .

DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preferred embodiments of the present disclosure will be 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 in light of the description herein. It is also understood that the following embodiments of the present disclosure can be used alone or in combination.

In one aspect, the present disclosure provides a compound of the general formula R _a -P(=O)R ¹ R ²
or a salt thereof,
During the ceremony,
R ¹ and R ² are different or the same and each independently represent a substituted aryl group;
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.

Various compound products derived from the disclosed diarylphosphine oxide derivatives having substituents on the aryl groups can be products with reduced electrical loss (dielectric dissipation factor, Df), lower dielectric constant (Dk) and dielectric dissipation factor (Df), and higher insulating properties compared to the corresponding aryl group phosphine oxide derivatives without substituents. While not wishing to be bound by theory, the introduction of sterically hindering substituents may suppress the aryl group's sway, reducing loss and lowering the dielectric constant (Dk) and dielectric dissipation factor (Df), potentially resulting in higher insulating properties.

In one embodiment, the aryl groups in ^R1 and ^R2 each independently have 1, 2, or 3 substituents. The number of substituents can be adjusted to obtain products with desirable electrical properties.

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

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

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

In one embodiment, the substituents on the aryl groups in ^R1 and ^R2 are selected from the group consisting of halogen, alkyl, -Oalkyl, -OH, _-NO2 , _-NH2 , -C(=O)H, -C(=O)alkyl, and -C(=O)Oalkyl, wherein 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.

In one embodiment, the substituents on the aryl group in R ¹ and R ² are selected from the group consisting of halogen, —C1 to C4 alkyl, —OC1 to C4 alkyl, —OH, —NO ₂ , —NH ₂ , —C(═O)H, —C(═O)C1 to C4 alkyl, and —C(═O)OC1 to C4 alkyl, wherein the alkyl is substituted or unsubstituted.

In one embodiment, in R ¹ and R ² , the substituents are each independently a —C1 to C4 alkyl group.

In one embodiment, the aryl group having the substituent in ^R1 and ^R2 is a monocyclic, bicyclic, or tricyclic ring having a substituent. Without wishing to be bound by theory, the dielectric loss tangent (Df) can be adjusted by the ring size of the aryl group, and desired products can be prepared.

In one embodiment, in R ¹ and R ² , the aryl group having a substituent is a phenyl group having a substituent.

In one embodiment, R ¹ and R ² are

where * indicates the point of attachment.

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 hydroxy groups, or a group containing a phosphine oxide. By adjusting R ^a , it can be used for various purposes.

In one embodiment, R _a is

,

or a dihydroxy-substituted aryl group;
^R3 and ^R4 are each independently hydrogen or a substituted or unsubstituted alkyl group;
n is 1 or 2;
wherein when n is 2, each ^R3 may be the same or different, and each ^R4 may be the same or different;
^R5 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 each independently represent 1 to 3;
wherein when _n1 is 2 or 3, each ^R6 may be the same or different, and each ^R7 may be the same or different;
wherein when _n2 is 2 or 3, each ^R8 may be the same or different, and each ^R9 may be the same or different;
* indicates the point of attachment.

In one embodiment, R _a is an acryloyloxymethyl group, a methacryloyloxymethyl group, an epoxymethyloxypropyl group, or a 2,5-dihydroxyphenyl group.

In one embodiment, the phosphine oxide compound is represented by the following general formula (I):

(I)
wherein R ¹ and R ² are as defined above, and R ³ , R ⁴ , n, and R ⁵ are as defined above.

In one embodiment, the phosphine oxide compound is represented by the following general formula (II):

(II)
wherein R ¹ and R ² are as defined above, and R ⁶ , R ⁷ , R ⁸ , R ⁹ , n ₁ , and n ₂ are as defined above.

In one embodiment, the phosphine oxide compound is represented by the following general formula (III):

(III)
wherein R ¹ and R ² are as defined above. The compound can be kneaded with a resin.

In one embodiment, 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)
is shown by
^R1 and ^R2 are as described above. The linker may be a group that is not reactive in the intended application. By adjusting the linker, phosphine oxide compounds with various properties can be obtained.

In one embodiment, 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 or heteroarylene group;
n ₃ , n ₄ and n ₅ each independently represent an integer of 0 to 3.

In one embodiment, the linker is

It is.

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

(IVa)
is shown by
^R1 and ^R2 are as defined above;
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.

In one aspect, the present disclosure provides a compound represented by the following general formula (V):

(V)
(In the formula,
R ¹ and R ² are each independently a substituted or unsubstituted aryl group;
^R3 and ^R4 are each independently hydrogen or a substituted or unsubstituted alkyl group;
n is 1 or 2;
wherein when n is 2, each ^R3 may be the same or different, and each ^R4 may be the same or different;
^R5 is hydrogen or a substituted or unsubstituted alkyl group).

In one embodiment, it is a copolymer of (meth)acrylic acid, (meth)acrylic acid esters, (meth)acrylic acid halides, (meth)acrylic acid salts, styrene, or acrylonitrile.

In one embodiment, the following general formula (VI)

(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;
where _n1 is 2, each ^R6 may be the same or different, and each ^R7 may be the same or different;
wherein when _n2 is 2, each ^R8 may be the same or different, and each ^R9 may be the same or different) as a constituent.

In one embodiment, it is a copolymer with an epoxy compound. The phosphine oxides of the present disclosure can be used to modify a variety of epoxy compounds.

In one aspect, an additive is provided comprising the above compound or salt, or a homopolymer or copolymer.

In one aspect, an anti-fogging agent is provided comprising the above compound or salt, or homopolymer or copolymer.

In one aspect, a flame retardant is provided comprising the above compound or salt, or a homopolymer or copolymer.

In one aspect, electrical/electronic parts, office automation parts, automobile parts, train parts, aircraft parts, or fibers are provided that contain the above compound or salt, or homopolymer or copolymer.

In one aspect, a sheet, film, or acrylic glass is provided comprising the above compound or salt, or homopolymer or copolymer.

In one aspect, a polymerization additive is provided comprising the above compound or salt, or a homopolymer or copolymer.

In one aspect, a surface modifier is provided comprising the above compound or salt, or a homopolymer or copolymer.

In one aspect, a phosphorus-donating agent is provided that includes the above compound or salt, or a homopolymer or copolymer.

In one aspect, there is provided use of a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, in an additive, anti-fogging agent, flame retardant, electrical/electronic part, office automation part, automobile part, train part, aircraft part, fiber, sheet, film, acrylic glass, polymerization additive, surface modifier, or phosphorus-additive. These uses also include the use of a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, to simultaneously fulfill multiple applications, such as two or more, three or more, of the additive, anti-fogging agent, flame retardant, electrical/electronic part, office automation part, automobile part, train part, aircraft part, fiber, sheet, film, acrylic glass, polymerization additive, surface modifier, or phosphorus-additive.

In one aspect, the present disclosure provides a method for using a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, in an electrical/electronic part, an office automation part, an automobile part, a train part, an aircraft part, a fiber, a sheet, a film, or acrylic glass, or as an additive, an anti-fogging agent, a flame retardant, a polymerization additive, a surface modifier, or a phosphorus-providing agent, the method comprising the step of applying the compound or salt, or the homopolymer or copolymer to an object in need thereof.

In a more specific embodiment, the method of the present disclosure includes adding a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, to a target substance (e.g., a substance containing, as a main component, 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 phenolic resin, a melamine resin, or a benzoxazine resin).

In another embodiment, the method of the present disclosure includes adding a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, to an object (e.g., a material intended to be anti-fogging, such as a poly(meth)acrylic resin, a polycarbonate resin, a polyester resin, or a polystyrene resin), and completing the product as needed.

In another embodiment, the method of the present disclosure includes adding a compound or salt of the present disclosure, or a homopolymer or copolymer of the present disclosure, to a target object (e.g., 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 phenolic resin, a melamine resin, or a benzoxazine resin), and optionally completing the product.

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 (e.g., an electrical/electronic part, an office automation part, an automobile part, a train part, an aircraft part, for example, containing, as a main component, 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, phenolic resin, melamine resin, or benzoxazine resin), and, if necessary, completing the product.

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 a target object (e.g., a fiber, a sheet, or a film, for example, containing, as a main component, 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, phenolic resin, melamine resin, or benzoxazine resin), and, if necessary, completing the product.

In another embodiment, the method of the present disclosure includes 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 completing the product as needed.

In another embodiment, the method of the present disclosure includes 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 to be polymerized, surface-modified, or phosphorus-imparted, 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 phenolic resin, a melamine resin, or a benzoxazine resin), and completing the product as needed.

In one embodiment, when the polymer of the present disclosure is a copolymer, it may be a copolymer copolymerized with a radically polymerizable monomer. Examples of the radically polymerizable monomer include, but are not limited to, styrene and acrylic esters (e.g., alkyl acrylates such as methyl acrylate and ethyl acrylate, alkyl styrenes such as methylstyrene and ethylstyrene, etc.). More specifically, examples of radically polymerizable monomers that can be used to produce the polymer of the present disclosure include 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, methacrylic Examples of the methacrylate copolymer include, but are not limited to, 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; etc. The copolymer may be a copolymer with (meth)acrylic acid, a (meth)acrylic acid ester, or a (meth)acrylic acid salt.

The present disclosure provides methods for producing monomers. Examples of such methods include, but are not limited to, the following:

(Methods for producing compounds of the present disclosure)
(Method 1)
Reaction of a phosphorus-containing compound (R ¹ R ² P(═O)H) having one P—H bond with an aldehyde or ketone (R ³ C(═O)R ⁴ ) provides an intermediate compound of R ¹ R ² P(═O)—CR ³ R ⁴ —OH.

wherein 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.

This reaction can be carried out by heating the diarylphosphine oxide with an aldehyde or ketone in a solvent.

Aldehydes that can be used in this reaction include formaldehyde (methanal), acetaldehyde (ethanal), propionaldehyde (propanal), butanal, pentanal, hexanal, heptanal, octanal, nonanal, and decanal. Paraformaldehyde can be used as the formaldehyde.

Ketones that can be used in this reaction include acetone, methyl ethyl ketone, diethyl ketone, methyl propyl ketone, methyl isobutyl ketone, methyl amyl ketone, etc.

Solvents used in this reaction include methanol, ethanol, acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, dimethylacetamide, etc.

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 is obtained.

Solvents that can be used in this reaction include ethyl acetate, butyl acetate, diethyl ether, tetrahydrofuran, dioxane, dichloromethane, dimethylformamide, and dimethylacetamide. Acryloyl chloride and methacrylic acid chloride can also be used. Bases that can be used include potassium carbonate, sodium carbonate, sodium bicarbonate, cesium carbonate, trimethylamine, and triethylamine.

Phosphorus-containing (meth)acrylic acid ester derivatives can also be obtained by reacting the above intermediate compound with (meth)acrylic acid in a solvent.

Solvents used in this reaction include chloroform, dichloromethane, 1,2-dichloroethane (EDC), diethyl ether, THF, dioxane, etc. Acrylic acid and methacrylic acid, etc. may also be used.

(Method 2)
A phosphorus-containing compound (R ¹ R ² P(═O)H) with one P—H bond is converted into an epoxide (oxirane).

to give the intermediate compound R ¹ R ² P(═O)—CH ₂ —CHR ³ —OH.

wherein R ¹ and R ² are each independently an aryl group, and R ³ is hydrogen or a substituted or unsubstituted alkyl group.

When this intermediate compound is reacted with (meth)acrylic acid chloride in the presence of a base, a phosphorus-containing (meth)acrylic acid ester derivative is obtained.

is obtained.

Phosphorus-containing (meth)acrylic acid ester derivatives can also be obtained by reacting the above intermediate compound with (meth)acrylic acid in a solvent.

Solvents used in this reaction include chloroform, dichloromethane, 1,2-dichloroethane (EDC), diethyl ether, THF, dioxane, etc. Acrylic acid and methacrylic acid, etc. may also be used.

(Synthesis of diarylphosphine oxide derivatives containing epoxy groups)
The 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.

(In the formula, n ₂ '=n ₂ -2)
The radical initiator may be the same as that used in the production method of the polymer. Examples of the polymerization initiator include azo compound-based thermal polymerization initiators such as azoisobutyronitrile (AIBN), azobisdimethylvaleronitrile (ADVN), and azobismethylbutyronitrile (AMBN), and examples of organic peroxide-based thermal polymerization initiators include dibenzoyl peroxide (BPO), t-butyl hydroperoxide (TBHP), cumene hydroperoxide, and di-t-butyl hydroperoxide.

Reaction solvents include methanol, ethanol, acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, dimethylacetamide, ethyl acetate, butyl acetate, etc.

(Synthesis of diarylphosphine oxide derivatives containing dihydroxy-substituted aryl groups)
The diarylphosphine oxide derivative containing a dihydroxy-substituted aryl group can be produced by dissolving the diarylphosphine oxide in a solvent, adding dropwise a benzoquinone derivative dissolved in the solvent, and heating the mixture for aging.

wherein R ^x and R ^y can each be an optional substituent, or can be taken together to form a ring.
Examples of the reaction solvent include methanol, ethanol, acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, dimethylacetamide, ethyl acetate, and butyl acetate.

(Synthesis of diphosphine compounds)
The preparation can be carried out by dissolving the diarylphosphine oxide derivative in a solvent, adding a base and stirring, and then adding the dihalo compound dropwise.

wherein X is a halogen.
Usable bases include alkali metals (lithium, sodium, potassium), alkyl metals (alkyllithium, alkylsodium, alkylpotassium), alkoxyalkali 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), and the like.

Reaction solvents include methanol, ethanol, acetone, methyl ethyl ketone, diethyl ether, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, dimethylacetamide, ethyl acetate, butyl acetate, etc.

Dihalo compounds include dichloroethane, dibromoethane, diiodoethane, α,α'-dichloro-paraxylene, α,α'-dibromo-paraxylene, and α,α'-diiodo-paraxylene.

(Method for producing polymer)
The polymer of the present disclosure can be obtained by polymerizing the compound of the present disclosure. The polymerization may be homopolymerization or copolymerization. Polymerization of compounds having an acrylic group or a methacrylic group 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 dibenzoyl peroxide (BPO), t-butyl hydroperoxide (TBHP), cumene hydroperoxide, di-t-butyl hydroperoxide, etc. 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 diethylene tetramine, triethylene tetramine, and m-xylene diamine, and aromatic amines such as diaminophenylmethane, m-phenylenediamine, and trimethylene bis(4-aminobenzoate)), various phenol-based curing agents (e.g., bisphenol A, bisphenol F, and 4,4-dihydroxydiphenylmethane), and various thiol-based curing agents (e.g., 1,4-butanedithiol and 1,6-hexanedithiol). Examples of the cationic polymerization initiator 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 examples of the thermal cationic polymerization initiator include sulfonium salts (e.g., (2-ethoxy-1-methyl-2-oxoethyl)methyl-2-naphthalenylsulfonium hexafluoroantimonate, 4-(methoxycarbonyloxy)phenylbenzylmethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium hexafluoroantimonate), and phosphonium salts (e.g., ethyltriphenylphosphonium hexafluoroantimonate, tetrabutylphosphonium hexafluoroantimonate).

In the present disclosure, polymers can be produced that contain the following as constituent components derived from acrylate compounds:

(A)
The present disclosure also provides copolymers of acrylate compounds with methyl acrylate, methyl methacrylate, styrene, and acrylonitrile.

In the present disclosure, a polymer can be produced that contains the following as a constituent component derived from a compound having an epoxy group:

The present disclosure also provides copolymers with epoxy compounds.

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

The present disclosure provides articles comprising the disclosed compounds or salts thereof, or the disclosed homopolymers or copolymers. Examples of such articles include anti-fogging agents, flame retardants, electrical/electronic parts, office automation parts, automobile parts, train parts, aircraft parts, fibers, sheets, films, or acrylic glass, polymerization additives, and surface modifiers.

The homopolymers or copolymers of the present disclosure have low water absorption and are useful as anti-fogging agents. The compounds of the present disclosure or salts thereof can also be used as anti-fogging agents. When the compounds of the present disclosure or salts thereof are in solid form (preferably powder form), they are easy to handle and can be used in appropriate amounts. Waste can be reduced compared to when they are in liquid form.

The disclosed compounds or salts thereof, or the disclosed homopolymers or copolymers contain phosphorus and can be useful as flame retardants. When the disclosed compounds or salts thereof are solid (preferably powder), they are easy to handle and can be used in appropriate amounts. This can result in less waste than when they are liquid.

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, etc.

The homopolymers or copolymers of the present disclosure are easy to mold and transparent, so they can be used as sheets, films, or acrylic glass.

The compounds of the present disclosure or their salts are polymerizable and can be used as polymerization additives to modify the properties of the resulting polymer. When the compounds of the present disclosure or their salts are solid (preferably powder), they are easy to handle and can be used in appropriate amounts. This can result in less waste than when they are liquid.

The compounds of the present disclosure or salts thereof can be bound 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 in the form of a solid (preferably a powder), they are easy to handle and can be used in appropriate amounts. This can result in less waste than when they are in the form of a liquid.

In one aspect, the present disclosure provides a phosphorus providing agent comprising the compound of the present disclosure or a salt thereof. The phosphorus providing agent of the present disclosure can be used in the manufacture of fertilizers, agricultural chemicals, pharmaceuticals, insecticides, explosives, electronic materials, catalysts, flame retardants, metal surface treatment agents, detergents, antifreeze solutions, surfactants, antifoaming agents, lubricants, and the like. 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 used in an appropriate amount. Waste can be reduced compared to when it is a liquid.

The compound or salt thereof of the present disclosure contains a (meth)acrylic acid moiety that can easily undergo radical polymerization, making it possible to easily add phosphorus to other substances. The target to which phosphorus is added may be anything with which the radical generated in the (meth)acrylic acid moiety can react. The compound or salt thereof of the present disclosure has the effect of reducing water absorption, and is also useful for producing compounds with low water absorption. When the compound or salt thereof of the present disclosure is in the form of a solid (preferably powder), it is easy to handle and can be used in an appropriate amount. Waste can be reduced compared to when it is in the form of a liquid.

In one aspect, the present disclosure provides a surface treatment method using the compound or salt thereof disclosed herein. This surface treatment method can reduce the water absorption of the surface. The method can include a step of polymerizing the compound or salt represented by general formula (I) on the surface. The surface can be resin or glass. When the compound or salt thereof disclosed herein is in the form of a solid (preferably powder), it is easy to handle and can be used in an appropriate amount. Waste can be reduced compared to when it is in the form of a liquid.

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 were specifically set forth.

The present disclosure has been described above by illustrating preferred embodiments for ease of understanding. Below, 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 intended to limit 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.

This disclosure will be explained in more detail using the following examples and comparative examples, but this disclosure should not be interpreted as being limited to these examples. Examples obtained by appropriately combining the technical means disclosed in each example are also considered to be within the scope of this disclosure.

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: polymethyl acrylate Ph: phenyl rt: room temperature (for example, 15°C to 25°C)
St: styrene THF: tetrahydrofuran The compounds of the present disclosure and their synthesis are further illustrated 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, generic names are used, and it is understood that these generic names will be recognized by those skilled in the art.

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

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

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

Dielectric constant measurements were performed using Toyo Corporation's dielectric constant measurement system WKR6510P at a measurement frequency of 1 MHz and a measurement temperature of 25°C.

As for solvents, other general solvents used were first-class products manufactured by Sigma-Aldrich Japan.

(Example 1)

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

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

A 100 mL three-neck flask was charged with 1.43 g of dimesitylphosphine oxide, 0.57 g of allyl glycidyl ether, and 13.0 g of toluene. 1.64 g of azoisobutyronitrile (AIBN) was added, and the mixture was heated and stirred at 80 ^° C. for 3 hours. The reaction mixture was allowed to cool to room temperature, concentrated, and vacuum-dried to obtain 2.03 g of a colorless, transparent, viscous liquid.
^31P NMR (NONE, 161 MHz) = δ 29.3
Example 4

28.6 g of dimesitylphosphine oxide and 57.3 g of toluene were added to a 300 mL four-neck flask and stirred at room temperature until completely dissolved. 10.8 g of parabenzoquinone and 108.1 g of toluene were added to a 300 mL beaker and the parabenzoquinone was completely dissolved. The toluene solution of parabenzoquinone was added to the 300 mL four-neck flask and stirred at 60 ^° C for 1 hour. The reaction solution was allowed to cool to room temperature, and the resulting precipitate was collected by filtration and dried to yield 32.1 g of a white powder.
^31P NMR (DMSO-d6, 161 MHz) = δ 35.3
Example 5

28.6 g of dimesitylphosphine oxide and 114.5 g of toluene were added to a 300 mL four-neck 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 ^° C for 3 hours. The reaction solution was allowed to cool to room temperature, and the resulting precipitate was collected by filtration and dried to obtain 18.3 g of a pale yellow powder.
^31P NMR (NONE, 161 MHz) = δ 26.5
Example 6

28.6 g of dimesitylphosphine oxide and 143.2 g of toluene were added to a 300 mL four-neck 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'-dichloroparaxylene was added and stirred at 60 ^° C for 3 hours. The reaction solution was allowed to cool to room temperature, and the resulting precipitate was collected by filtration and dried to obtain 25.3 g of a pale yellow powder.
^31P 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, and four times the weight of 2-butanone was added and thoroughly stirred. After degassing and nitrogen substitution, the mixture was heated to 40°C. After 0.20 g of benzoyl peroxide was added, the temperature inside the reaction vessel was raised to 80°C and the reaction was carried out for 20 hours. After completion of the reaction, the reaction solution was added dropwise to hexane to precipitate the produced polymer. The precipitated polymer was washed with ion-exchanged water and dried in a vacuum dryer, yielding 14.5 g of white powder. The weight-average molecular weight and dielectric constant of the obtained polymer were measured.

(Comparative Example 1)
20.0 g of Comparative Compound 1 was weighed into a 200 mL separable flask, and four times the weight of 2-butanone was added and thoroughly stirred. After degassing and nitrogen substitution, the mixture was heated to 40°C. 0.22 g of benzoyl peroxide was added, and 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 added dropwise to hexane to precipitate the produced polymer. The precipitated polymer was washed with ion-exchanged water and dried in a vacuum dryer, yielding 16.3 g of a white powder. The weight-average molecular weight and dielectric constant of the obtained polymer were measured.

Comparative compound 1

Polymers made from the compounds of the present invention, which have substituents on the aryl groups, have been shown to have significantly lower dielectric constants (Dk) and dielectric loss tangents (Df) than polymers made from the compound of Comparative Example 1, which does not have substituents on the aryl groups.

While the present disclosure has been illustrated using preferred embodiments thereof, it is understood that the scope of the present disclosure should be construed solely in accordance with the claims. This application claims priority to Japanese Patent Application No. 2020-130769 (filed July 31, 2020), the contents of which are incorporated herein by reference in their entirety. It is understood that the patents, patent applications, and other documents cited herein are incorporated herein by reference in their entirety as if the contents themselves were specifically set forth herein. It is understood that the patents, patent applications, and other documents cited herein are incorporated herein by reference in their entirety as if the contents themselves were specifically set forth herein.

The novel phosphorus compounds can be used in a variety of applications, including anti-fogging agents, flame retardants, electrical/electronic parts, office automation parts, automobile parts, train parts, aircraft parts, fibers, sheets, films, acrylic glass, and polymerization additives. They can also be used as phosphorus-donating agents.

Claims (31)

The following general formula (I)

or a salt thereof,
During the ceremony,
R ¹ and R ² are different or the same and each independently represent a substituted aryl group, and the aryl group in R ¹ and R ² each independently has one, two, or three substituents;
^R3 and ^R4 are each independently hydrogen or a substituted or unsubstituted alkyl group;
n is 1 or 2;
wherein when n is 2, each ^R3 may be the same or different, and each ^R4 may be the same or different;
^R5 is hydrogen or a substituted or unsubstituted alkyl group;
A phosphine oxide compound or a salt thereof. 2. The phosphine oxide compound or a salt thereof according to claim 1, wherein the aryl groups in ^R1 and ^R2 each have one substituent. 2. The phosphine oxide compound or a salt thereof according to claim 1, wherein the aryl group in ^R1 and ^R2 each has two substituents. 2. The phosphine oxide compound or a salt thereof according to claim 1, wherein the aryl group in ^R1 and ^R2 each has three substituents. The compound or salt thereof according to any one of claims 1 to 4, wherein the substituents on the aryl group in R ¹ and R ² are selected from the group consisting of halogen, alkyl, -Oalkyl, -OH, -NO ₂ , -NH ₂ , -C(=O)H, -C(=O)alkyl, and -C(=O)Oalkyl, wherein the alkyl is substituted or unsubstituted. The compound or salt thereof according to any one of claims 1 to 5, wherein the substituents on the aryl group in R ¹ and R ² are selected from the group consisting of halogen, -C1 to C4 alkyl, -OC1 to C4 alkyl, -OH, -NO ₂ , -NH ₂ , -C(=O)H, -C(=O)C1 to C4 alkyl, and -C(=O)OC1 to C4 alkyl, wherein the alkyl is substituted or unsubstituted. 7. The phosphine oxide compound or a salt thereof according to claim 1, wherein in R ¹ and R ² , the substituents are each independently a —C1 to C4 alkyl group. 8. The phosphine oxide compound or a salt thereof according to claim 1, wherein in ^R1 and ^R2 , the aryl group having a substituent is a monocyclic, bicyclic or tricyclic ring having a substituent. 9. The phosphine oxide compound or a salt thereof according to claim 1, wherein in ^R1 and ^R2 , the aryl group having a substituent is a phenyl group having a substituent. ^R1 and ^R2 are

The phosphine oxide compound or a salt thereof according to any one of claims 1 to 9, wherein * indicates a point of attachment,
Here, when the aryl group in R ¹ and R ² each has one substituent, R ¹ and R ² are each

and
When the aryl group in R ¹ and R ² each has two substituents, R ¹ and R ² each represent

and
When the aryl group in R ¹ and R ² each has three substituents, R ¹ and R ² are each

That is,
A phosphine oxide compound or a salt thereof . 2. The phosphine oxide compound or a salt thereof according to claim 1, wherein the substituents on the aryl group in ^R1 and ^R2 are substituted or unsubstituted alkyl. The following general formula (II)

or a salt thereof,
R ¹ and R ² are different or the same and each independently represent a substituted 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 each independently represent 1 to 3;
wherein when _n1 is 2 or 3, each ^R6 may be the same or different, and each ^R7 may be the same or different;
wherein when _n2 is 2 or 3, each ^R8 may be the same or different, and each ^R9 may be the same or different;
A phosphine oxide compound or a salt thereof. 13. The phosphine oxide compound or a salt thereof according to claim 12, wherein the aryl groups in ^R1 and ^R2 each independently have one, two or three substituents. 14. The phosphine oxide compound or a salt thereof according to claim 13, wherein the substituents on the aryl group in R ¹ and R ² are substituted or unsubstituted alkyl. The following general formula (III)

or a salt thereof, wherein R ¹ and R ² are different from or the same as each other and each independently represent an aryl group having a substituent, and the aryl group in R ¹ and R ² each independently has two or three substituents. 16. The phosphine oxide compound or a salt thereof according to claim 15, wherein the substituents on the aryl group in ^R1 and ^R2 are substituted or unsubstituted alkyl. The following general formula (IV):
(R ¹ )(R ² )P(═O)-(linker)-P(═O)(R ¹ )(R ² )
(IV)
or a salt thereof,
R ¹ and R ² are different or the same and each independently represent an aryl group having three substituents;
(1)
The linker is
-(Ar) _n5 - ,
n5 is 1 to 3, and Ar is _an unsubstituted arylene group or heteroarylene group , or
(2)
The linker is
-(C(R ¹⁰ )(R ¹¹ )) _n3 -(Ar) _n5 -(C(R ¹² )(R ¹³ )) _n4 -;
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 or heteroarylene group;
n ₃ , n ₄ and n ₅ each independently represent 1 to 3 ;
A phosphine oxide compound or a salt thereof. 18. The phosphine oxide compound or a salt thereof according to claim 17, wherein the substituents on the aryl group in ^R1 and ^R2 are substituted or unsubstituted alkyl. The linker is

18. The compound according to claim 17, wherein: The following general formula (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;
where _n1 is 2, each ^R6 may be the same or different, and each ^R7 may be the same or different;
wherein when _n2 is 2, each ^R8 may be the same or different, and each ^R9 may be the same or different) as a constituent. The copolymer according to claim 20, which is a copolymer with an epoxy compound. An additive comprising a compound or salt according to any one of claims 1 to 19, or a homopolymer or copolymer according to claim 20 or 21. An anti-fogging agent comprising a compound or salt according to any one of claims 1 to 19, or a homopolymer or copolymer according to claim 20 or 21. A flame retardant comprising a compound or salt according to any one of claims 1 to 19, or a homopolymer or copolymer according to claim 20 or 21. An electrical/electronic part, an office automation part, an automobile part, a train part, an aircraft part, or a fiber, 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. A sheet, film, or acrylic glass comprising the compound or salt described in any one of claims 1 to 19, or the homopolymer or copolymer described in claim 20 or 21. A polymerization additive comprising a compound or salt according to any one of claims 1 to 19, or a homopolymer or copolymer according to claim 20 or 21. A surface modifier comprising a compound or salt according to any one of claims 1 to 19, or a homopolymer or copolymer according to claim 20 or 21. A phosphorus-donating agent comprising the compound or salt described in any one of claims 1 to 19, or the homopolymer or copolymer described in claim 20 or 21. 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 electrical/electronic parts, office automation parts, automobile parts, train parts, aircraft parts, fibers, sheets, films, 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-providing agent. A method for 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 an electrical/electronic part, an office automation part, an automobile part, a train part, an aircraft part, a fiber, a sheet, a film, or acrylic glass, or for using the compound or salt, or the homopolymer or copolymer as an additive, an anti-fogging agent, a flame retardant, a polymerization additive, a surface modifier, or a phosphorus-providing agent, the method comprising the step of applying the compound or salt, or the homopolymer or copolymer to an object in need thereof.