Modifier for improving dielectric characteristics of thermosetting resin composition

Abstract

The present invention addresses the problem of providing a modifier for a thermosetting resin composition having excellent dielectric characteristics. The present invention provides a dielectric characteristic modifier comprising a monomer compound represented by general formula 1 or a multimer compound represented by general formula 2, which has a structure wherein a phosphorus atom and a nitrogen atom are bonded to each other. Also provided is a compound for use in the modifier. The modifier can be added to thermosetting resins, such as epoxy resins and polyphenylene ether resins having ethylenically unsaturated bonds, as modifiers. Also provided is a thermosetting resin composition that comprises the modifier and a thermosetting resin. The thermosetting resin composition has a low dielectric loss tangent and can achieve excellent dielectric characteristics.

Description

Modifier for improving the dielectric properties of thermosetting resin compositions

[0001] The present invention relates to modifiers for thermosetting resin compositions having excellent dielectric properties, and compounds that can be used as such modifiers. In particular, the present invention relates to modifiers comprising phosphoramidate compounds having a covalent bond between a phosphorus atom and a nitrogen atom (hereinafter referred to herein as a "PN bond"). The present invention also relates to thermosetting resin compositions that can be used in printed circuit boards having excellent dielectric properties. The present invention further relates to printed circuit boards using such thermosetting resin compositions and to methods for manufacturing the same.

[0002] In recent years, high frequencies have become increasingly common in printed circuit boards, and there is a demand for thermosetting resin compositions with excellent dielectric properties that can be used in high-frequency printed circuit boards. In particular, there is a demand for thermosetting resin compositions with low dielectric loss tangent values.

[0003] On the other hand, it is known that phosphoramidate compounds can be used as flame retardants (paragraphs 0030-0031 of Patent Document 1, claim 1 of Patent Document 2). However, it was not known that these phosphoramidate compounds could improve the dielectric properties of thermosetting resin compositions for printed circuit boards.

[0004] Japanese Patent Publication No. 2000-154277, Japanese Patent Publication No. 2001-354836

[0005] The object of the present invention is to provide a thermosetting resin composition having excellent dielectric properties (e.g., a low dielectric loss tangent).

[0006] The inventors of this invention conducted intensive research to solve the above problems and, as a result, discovered that a phosphoramidate compound having a specific structure can solve the above problems, thus completing the present invention.

[0007] Specifically, the present invention provides, for example, the following modifiers, compounds, thermosetting resin compositions, and methods for producing them.

[0008] (Item 1) A modifier for reducing transmission loss in a thermosetting resin composition for a circuit board, comprising a monomeric compound represented by the following general formula 1 or a polymeric compound represented by general formula 2, Here, in general formula 1, L １ is NR １ｂ and R １ａ and R １ｂ are the following structure 1a or structure 1b: (Structure 1a: R １ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms, and R １ｂ is a hydrogen atom or a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms.) (Structure 1b: R １ａ and R １ｂ are each a straight-chain alkyl group and R １ａ and R １ｂ are bonded together, and the nitrogen atom in L １ and R １ａ and R １ｂ together form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, where one CH of the nitrogen-containing aliphatic monocyclic group ２The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl groups may each be independently linear or branched alkyl groups having 1 to 4 carbon atoms. Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) and L ２ is O or NR ２ｂ And L ２ If O, then R ２ａ L is a phenyl group, which may be independently substituted with 1 to 3 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ２ NR ２ｂ If so, R ２ａ and R ２ｂ The following structure 2a or structure 2b: (Structure 2a: R ２ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ２ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 2b: R ２ａ and R ２ｂ Each of them is a linear alkyl group and R ２ａ and R ２ｂ They combine, L２ The nitrogen atom and R inside ２ａ and R ２ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) and L ３ is O or NR ３ｂ And L ３ If O, then R ３ａ L is a phenyl group, which may be independently substituted with 1 to 3 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ３ NR ３ｂ If so, R ３ａ and R ３ｂ The following structure 3a or structure 3b: (Structure 3a: R ３ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ３ｂ(This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 3b: R ３ａ and R ３ｂ Each of them is a linear alkyl group and R ３ａ and R ３ｂ They combine, L ３ The nitrogen atom and R inside ３ａ and R ３ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms.) And here, in general formula 2, the polymer compound has at least two PN bonds, where the PN bond is a covalent bond between one phosphorus atom and one nitrogen atom, R １０ L is a phenylene group, where the phenylene group may be independently substituted with 1 to 3 alkyl groups, and the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms. １１ is O or NR １１ｂ And L １１ If O, then R １１ａL is a phenyl group, which may be independently substituted with 1 to 3 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. １１ NR １１ｂ If so, R １１ａ and R １１ｂ The following structure 4a or structure 4b: (Structure 4a: R １１ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １１ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 4b: R １１ａ and R １１ｂ Each of them is a linear alkyl group and R １１ａ and R １１ｂ They combine, L １１ The nitrogen atom and R inside １１ａ and R １１ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) and L １２ is O or NR １２ｂ And L １２ If O, then R １２ａ L is a phenyl group, which may be substituted with 1 to 3 alkyl groups, where the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. １２ NR １２ｂ If so, R １２ａ and R １２ｂ The following structure 5a or structure 5b: (Structure 5a: R １２ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １２ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 5b: R １２ａ and R １２ｂ Each of them is a linear alkyl group and R １２ａ and R １２ｂ They combine, L１２ The nitrogen atom therein and R １２ａ and R １２ｂ combine together to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, wherein one CH ２ in the nitrogen-containing aliphatic monocyclic group may be replaced by O to form a nitrogen-containing and oxygen-containing aliphatic monocyclic group. Here, a benzene ring may be further condensed with the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing and oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing and oxygen-containing condensed ring group. Here, the nitrogen-containing aliphatic monocyclic group and the nitrogen-containing and oxygen-containing aliphatic monocyclic group having 2 carbon atoms may each independently be substituted with one or two alkyl groups, where the alkyl group is independently a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing aliphatic monocyclic group and the nitrogen-containing and oxygen-containing aliphatic monocyclic group having 3 to 9 carbon atoms may each independently be substituted with one to three alkyl groups, the alkyl group being independently a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms. Here, the nitrogen-containing condensed ring group and the nitrogen-containing and oxygen-containing condensed ring group may each independently be substituted with one to six alkyl groups, the alkyl group being independently a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms.) having, L １３ is O or NR １３ｂ where R １３ｂ is a hydrogen atom or a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms, and L １４ is O or NR １４ｂ where R １４ｂ is a hydrogen atom or a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms, and L １５ is O or NR １５ｂ where L １５ is O, R １５ａ is a phenyl group, which may be substituted with one to three alkyl groups, where the alkyl group is independently a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms, and L １５ is NR １５ｂ where R １５ａ and R １５ｂ are the following Structure 6a or Structure 6b: (Structure 6a: R１５ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １５ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 6b: R １５ａ and R １５ｂ Each of them is a linear alkyl group and R １５ａ and R １５ｂ They combine, L １５ The nitrogen atom and R inside １５ａ and R １５ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) and L １６ is O or NR １６ｂ And L １６ If O, then R １６ａL is a phenyl group, which may be independently substituted with 1 to 3 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. １６ NR １６ｂ If so, R １６ａ and R １６ｂ The following structure 7a or structure 7b: (Structure 7a: R １６ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １６ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 7b: R １６ａ and R １６ｂ Each of them is a linear alkyl group and R １６ａ and R １６ｂ They combine, L １６ The nitrogen atom and R inside １６ａ and R １６ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. １０ These are 1 to 6, and here, in general formula 2, L １１ and L １２ O and L １３ NR １３ is or L １１ and L １３ O and L １２ NR １２ is or L １２ and L １３ O and L １１ NR １１ And L １４ and L １５ O and L １６ NR １６ is or L １４ and L １６ O and L １５ NR １５ is or L １５ and L １６ O and L １４ NR １４ It is a modifier.

[0009] (Item 2) The modifier according to Item 1, wherein each of the rings present in the compound is either a six-membered ring or a fused ring formed by the fusion of a six-membered ring and a benzene ring.

[0010] (Item 3) The modifier according to Item 1 or Item 2, particularly according to Item 1, wherein each nitrogen atom in the compound is bonded to an unsubstituted phenyl group or an unsubstituted cyclohexyl group.

[0011] (Item 4) The modifier according to Item 1 or Item 2, particularly according to Item 1, wherein each nitrogen atom bonded to the phosphorus atom in the compound is one of the six ring atoms forming a six-membered ring, or one of the ring atoms of the six-membered ring portion of a fused ring formed by the condensation of a six-membered ring with a benzene ring.

[0012] (Item 5) The modifier according to any one of the above items 1 to 4, particularly according to item 1, wherein the compound is the monomer type compound.

[0013] (Item 6) The modifier according to any one of the above items 1 to 4, particularly according to item 1, wherein the compound is the polymer type compound.

[0014] (Section 7) R １ａ , R ２ａ and R ３ａ The modifier according to item 5 above, wherein is an unsubstituted phenyl.

[0015] (Section 8) L １３ and L １４ The modifier described in item 6 or item 7 above, particularly the modifier described in item 6 above, which is the same as the modifier described in item 6 above.

[0016] (Section 9) L １３ and L １４ A modifier according to item 6 or item 7 above, particularly according to item 6 above, wherein is O.

[0017] (Item 10) L １１ and L １６ The same, and L １２ and L １５ A modifier according to any one of the above paragraphs 6, 8, and 9, particularly the modifier according to paragraph 9, which is the same as the above.

[0018] (Section 11) R １１ａ , R １２ａ , R １５ａ and R １６ａ A modifier according to any one of items 6 and 8 to 10, particularly according to item 6, wherein is an unsubstituted phenyl.

[0019] (Section 12) L １１ NR １１ｂ And L １２ ~L １５ is O, and L １６ NR １６ｂ The modifier described in any one of the above paragraphs 6 and 8 to 11, particularly the modifier described in paragraph 6.

[0020] (Section 13) R １０ A modifier according to any one of items 6 and 8 to 12, particularly according to item 6, wherein is an unsubstituted metaphenylene or an unsubstituted paraphenylene.

[0021] (Item 14) General formula 2A below: A compound represented by R ２０ R is a phenylene group, where the phenylene group may be independently substituted with 1 to 3 alkyl groups, and the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms. ２１ａ and R ２１ｂ The following structure 8a or structure 8b: (Structure 8a: R ２１ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ２１ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 8b: R ２１ａ and R ２１ｂ Each of them is a linear alkyl group and R ２１ａ and R ２１ｂ The nitrogen atom and R bond together. ２１ａ and R ２１ｂThese combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) and R ２２ａ R is a phenyl group, which may be substituted with 1 to 3 alkyl groups, and the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms. ２５ａ R is a phenyl group, which may be substituted with 1 to 3 alkyl groups, and the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms. ２６ａ and R ２６ｂ The following structure 9a or structure 9b: (Structure 9a: R ２６ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ２６ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 9b: R ２６ａ and R ２６ｂEach of them is a linear alkyl group and R ２６ａ and R ２６ｂ The nitrogen atom and R bond together. ２６ａ and R ２６ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ２０ n is 1 to 6, where n ２０ If R is 1, ２０ is an unsubstituted phenylene group, and two oxygen atoms are bonded to the 1st and 3rd positions of the phenylene group, R ２１ａ is an unsubstituted phenyl group, R ２１ｂ is hydrogen and R ２２ａ and R ２５ａ is a 2,6-dimethylphenyl group and R ２６ａ If is an unsubstituted phenyl group, R ２６ｂ It is not hydrogen, and also n ２０ If R is 1, ２０A phenylene group substituted with two tert-butyl groups, two oxygen atoms are bonded to the 1st and 4th positions of the phenylene group, the two tert-butyl groups are bonded to the 2nd and 5th positions of the phenylene group, R ２１ａ is an unsubstituted phenyl group, R ２１ｂ is hydrogen, and R ２２ａ and R ２５ａ are 2,6-dimethylphenyl groups, and R ２６ａ is an unsubstituted phenyl group, then R ２６ｂ is not hydrogen, and further, n ２０ is 1 or 2, R ２０ is an unsubstituted phenylene group, two oxygen atoms are bonded to the 1st and 3rd positions of the phenylene group, R ２１ａ and R ２１ｂ together with a nitrogen atom form a morpholino group, R ２６ａ and R ２６ｂ together with a nitrogen atom form a morpholino group, and when R ２２ａ is an unsubstituted phenyl group, then R ２５ａ is not an unsubstituted phenyl group, Compound.

[0022] (Item 15) R ２２ａ and R ２５ａ are unsubstituted phenyl groups, the compound according to Item 14 above.

[0023] (Item 16) R ２０ is an unsubstituted metaphenylene group or an unsubstituted paraphenylene group, the compound according to Item 14 above.

[0024] (Item 17) R ２１ａ and R ２６ａ are unsubstituted phenyl groups or unsubstituted cyclohexyl groups, and R ２１ｂ and R ２６ｂ are hydrogen or methyl groups, or R ２１ａ and R ２１ｂ are bonded together with a nitrogen atom to form an unsubstituted piperidine group, an unsubstituted nitrogen-containing oxygen-containing aliphatic 6-membered ring group or an unsubstituted nitrogen-containing condensed ring group formed by condensation of a nitrogen-containing aliphatic 6-membered ring and a benzene ring, R ２６ａ [[ID=２６ｂ which combines with a nitrogen atom to form an unsubstituted piperidine group, an unsubstituted nitrogen-containing oxygen-containing aliphatic 6-membered ring group, or an unsubstituted nitrogen-containing condensed ring group in which a nitrogen-containing aliphatic 6-membered ring and a benzene ring are condensed, the compound according to item 14 above.

[0025] (Item 18) In the structure 8b, CH of the nitrogen-containing aliphatic monocyclic group ２ is not replaced by O, and in the structure 9b, CH of the nitrogen-containing aliphatic monocyclic group ２ is not replaced by O, the compound according to item 14 above.

[0026] (Item 19) R ２０ is an unsubstituted metaphenylene group or an unsubstituted paraphenylene group, R ２２ａ and R ２５ａ are unsubstituted phenyl groups, R ２１ａ and R ２６ａ are an unsubstituted phenyl group or an unsubstituted cyclohexyl group, and R ２１ｂ and R ２６ｂ are hydrogen or a methyl group, or R ２１ａ and R ２１ｂ combine with a nitrogen atom to form an unsubstituted nitrogen-containing aliphatic 6-membered ring, an unsubstituted nitrogen-containing oxygen-containing aliphatic 6-membered ring, an unsubstituted nitrogen-containing condensed ring group, or an unsubstituted nitrogen-containing oxygen-containing condensed ring group, and R ２６ａ and R ２６ｂ combine with a nitrogen atom to form an unsubstituted nitrogen-containing aliphatic 6-membered ring group, an unsubstituted nitrogen-containing oxygen-containing aliphatic 6-membered ring group, or an unsubstituted nitrogen-containing condensed ring group in which a nitrogen-containing aliphatic 6-membered ring and a benzene ring are condensed, the compound according to item 14 above.

[0027] (Item 20) A thermosetting resin composition for a circuit board, comprising a modifier according to any one of items 1 to 13 above or a compound according to any one of items 14 to 19 above and a thermosetting resin.

[0028] (Item 21) The thermosetting resin composition according to item 20 above, wherein the thermosetting resin contains an epoxy resin or a polyphenylene ether resin modified with an ethylenically unsaturated group.

[0029] (Item 22) A thermosetting resin composition according to item 20 or item 21, particularly according to item 20, for manufacturing an insulating layer in a high-frequency printed circuit board.

[0030] (Item 23) A high-frequency printed circuit board comprising a conductive layer and an insulating layer, wherein the insulating layer comprises a thermosetting resin composition as described in any one of items 20 to 22, particularly as described in item 20.

[0031] (Item 24) A method for manufacturing a high-frequency printed circuit board comprising a conductive layer and an insulating layer, comprising the step of curing a thermosetting resin composition described in any one of items 20 to 23, particularly the thermosetting resin composition described in item 20, to form the insulating layer.

[0032] According to the present invention, a thermosetting resin composition having excellent dielectric properties is provided. According to the present invention, a thermosetting resin composition having a low dielectric loss tangent value is provided.

[0033] Figure 1 shows the compound represented by formula 108 obtained in synthesis example 8. １ The 1H-NMR chart is shown. Figure 2 shows the compound represented by formula 109 obtained in synthesis example 9. １ The 1H-NMR chart is shown. Figure 3 shows the compound represented by formula 110 obtained in synthesis example 10. １ The 1H-NMR chart is shown. Figure 4 shows the compound represented by formula 111 obtained in synthesis example 11. １ The 1H-NMR chart is shown. Figure 5 shows the compound represented by formula 112 obtained in synthesis example 12. １ The 1H-NMR chart is shown. Figure 6 shows the compound represented by formula 113 obtained in synthesis example 13. １ The 1H-NMR chart is shown. Figure 7 shows the compound represented by formula 114 obtained in synthesis example 14. １ The 1H-NMR chart is shown. Figure 8 shows the compound represented by formula 115 obtained in synthesis example 15. １ The 1H-NMR chart is shown. Figure 9 shows the compound represented by formula 116 obtained in synthesis example 16. １ The H-NMR chart is shown.

[0034] The present invention provides a modifier comprising a phosphoramide compound having a PN bond. Details thereof are described below.

[0035] <Modifier of the Invention> In one embodiment, the present invention provides a modifier for reducing transmission loss in a thermosetting resin composition for circuit boards. Accordingly, in this specification, "modifier" means an additive for reducing transmission loss in a thermosetting resin composition. In one embodiment, the modifier of the present invention reduces the dielectric loss tangent value in a thermosetting resin composition. In this embodiment, "modifier" means an additive for reducing the dielectric loss tangent value in a thermosetting resin composition.

[0036] The modifier of the present invention is composed of phosphoramidate compounds. Specifically, the modifier is composed of monomeric compounds represented by the following general formula 1 or polymeric compounds represented by general formula 2.

[0037] The modifier may be the monomeric compound or the polymeric compound. Furthermore, the modifier may be a mixture of the monomeric compound and the polymeric compound. In the compound of general formula 2, there are multiple phosphorus atoms, and at least two of these phosphorus atoms each have a covalent bond (PN bond) with one nitrogen atom. That is, L in general formula 2 １１ ~L １３ In one of them, there is a nitrogen atom, and that nitrogen atom forms a PN bond with a phosphorus atom. And L in general formula 2 １４ ~L １６ In one of them, there is a nitrogen atom, and that nitrogen atom forms a PN bond with a phosphorus atom. For example, in the compound of general formula 2, n １０ When n is 1, there are two phosphorus atoms, and each of these two phosphorus atoms forms one PN bond, so there are two PN bonds in the compound. In this specification, the term "multimeric compound" means a compound having multiple phosphorus atoms. Here, the compound of general formula 2 is n １０ It has +1 phosphorus atom. And, n１０ Since the values ​​are 1 to 6, the compounds of general formula 2 have 2 to 7 phosphorus atoms. Compounds having 2 to 7 phosphorus atoms in this manner are referred to as "multimeric compounds" in this specification.

[0038] In this specification, compounds having a phosphorus atom bonded to an oxygen atom by a double bond, such as the compounds of general formula 1 and general formula 2, and in which the phosphorus atom is covalently bonded to one to three nitrogen atoms, are referred to as "phosphoramide compounds."

[0039] The above compound is described below.

[0040] [R １ａ -L １ [Structure of the part] In general formula 1, L １ NR １ｂ That is the case.

[0041] R １ａ and R １ｂ It has the following structure 1a or structure 1b.

[0042] <Structure 1a> R １ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １ｂThis is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom. In the modifier and compounds of the present invention, substituents having a ring structure may be substituted with alkyl groups. Therefore, in this specification, the names of substituents that may be substituted are used to include both unsubstituted and substituted substituents. For example, the term "phenyl group" is used to include phenyl groups substituted with alkyl groups (e.g., dimethylphenyl group). On the other hand, the names of substituents that do not have a ring structure are used to mean unsubstituted substituents unless otherwise stated. For example, the term "methyl group" refers to unsubstituted -CH ３ It means "foundation."

[0043] The above aryl group is preferably a phenyl group.

[0044] The number of carbon atoms in the aryl group is preferably 6 to 8, more preferably 6 or 7, and even more preferably 6. The number of carbon atoms in the cycloalkyl group is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more.

[0045] The number of carbon atoms in the above cycloalkyl group is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. The number of carbon atoms in the above cycloalkyl group is particularly preferably 6.

[0046] The number of carbon atoms constituting the ring of the above cycloalkyl group is preferably 5 to 8, more preferably 6 or 7, and even more preferably 6.

[0047] The number of alkyl groups present as substituents in the above aryl group or cycloalkyl group is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0048] R １ａIf the alkyl group is substituted with an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0049] R １ｂ If the alkyl group is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0050] <Structure 1b> R １ａ and R １ｂ Each of them is a linear alkyl group and R １ａ and R １ｂ They combine, L １ The nitrogen atom and R inside １ａ and R １ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms. The number of carbon atoms is preferably 3 or more, more preferably 4 or more. Furthermore, the number of carbon atoms is preferably 8 or less, more preferably 7 or less. Even more preferably 6 or less. Particularly preferably, the number of carbon atoms is 5.

[0051] Here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ It may be replaced by O to form a nitrogen-containing oxygen-containing aliphatic monocyclic group.

[0052] Here, a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group. In one embodiment, the nitrogen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms. In one embodiment, the nitrogen-containing oxygen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms.

[0053] Here, the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, preferably one alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0054] Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, and more preferably 2 alkyl groups. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0055] Here, the nitrogen-containing condensed ring group and the nitrogen- and oxygen-containing condensed ring group may each independently be substituted with 1 to 6 alkyl groups, preferably 1 to 4 alkyl groups, more preferably 1 or 2 alkyl groups. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and here, the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and still more preferably 1. Here, in the nitrogen-containing condensed ring group, the alkyl group as a substituent may be bonded to the nitrogen-containing aliphatic ring portion or may be bonded to the benzene ring portion. When the nitrogen-containing condensed ring group is substituted with two or more alkyl groups, it may be bonded to both the nitrogen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing aliphatic ring portion, and one or more alkyl groups may be bonded to the benzene ring portion, and the total number of alkyl groups may be two or more. Further, in the nitrogen- and oxygen-containing condensed ring group, the alkyl group as a substituent may be bonded to the nitrogen- and oxygen-containing aliphatic ring portion or may be bonded to the benzene ring portion. When the nitrogen- and oxygen-containing condensed ring group is substituted with two or more alkyl groups, alkyl groups may be bonded to both the nitrogen- and oxygen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen- and oxygen-containing aliphatic ring portion, and one or more alkyl groups may be bonded to the benzene ring portion, and the total number of alkyl groups may be two or more.

[0056] [R ２ａ -L ２ substructure] In General Formula 1, L ２ is O or NR ２ｂ .

[0057] When L ２ is O, R ２ａHere, is a phenyl group, which may be substituted with 1 to 3 alkyl groups, more preferably 1 or 2 alkyl groups, and even more preferably 1 alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0058] L ２ NR ２ｂ If so, R ２ａ and R ２ｂ This is either structure 2a or structure 2b below.

[0059] <Structure 2a> R ２ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ２ｂ This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0060] The above aryl group is preferably a phenyl group.

[0061] The number of carbon atoms in the aryl group is preferably 6 to 8, more preferably 6 or 7, and even more preferably 6. The number of carbon atoms in the cycloalkyl group is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more.

[0062] The number of carbon atoms in the above cycloalkyl group is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. The number of carbon atoms in the above cycloalkyl group is particularly preferably 6.

[0063] The number of carbon atoms constituting the ring of the above cycloalkyl group is preferably 5 to 8, more preferably 6 or 7, and even more preferably 6.

[0064] The number of alkyl groups present as substituents in the above aryl group or cycloalkyl group is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0065] R ２ａ If the alkyl group is substituted with an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0066] R ２ｂ If the alkyl group is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0067] <Structure 2b> R ２ａ and R ２ｂ Each of them is a linear alkyl group and R ２ａ and R ２ｂ They combine, L ２ The nitrogen atom and R inside ２ａ and R ２ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms. The number of carbon atoms is preferably 3 or more, more preferably 4 or more. Furthermore, the number of carbon atoms is preferably 8 or less, more preferably 7 or less. Even more preferably 6 or less. Particularly preferably, the number of carbon atoms is 5.

[0068] Here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ It may be replaced by O to form a nitrogen-containing oxygen-containing aliphatic monocyclic group.

[0069] Here, a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group. In one embodiment, the nitrogen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms. In one embodiment, the nitrogen-containing oxygen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms.

[0070] Here, the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, preferably one alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0071] Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, and more preferably 2 alkyl groups. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0072] Here, the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, preferably 1 to 4 alkyl groups, and more preferably 1 or 2 alkyl groups. Here, the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. Here, in the nitrogen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing condensed ring group is substituted with two or more alkyl groups, they may be bonded to both the nitrogen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing aliphatic ring portion and one or more alkyl groups may be bonded to the benzene ring portion, so that the total number of alkyl groups is two or more. Also, in the nitrogen-containing oxygen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing oxygen-containing condensed ring group is substituted with two or more alkyl groups, alkyl groups may be bonded to both the nitrogen-containing oxygen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion, and one or more alkyl groups may be bonded to the benzene ring portion, resulting in a total of two or more alkyl groups.

[0073] [R ２ａ -L ２ [Relationship between parts] L ２ is, L １ It may be the same as, or it may be different from. ２ａ R １ａ It may be the same as, or it may be different from. ２ａ -L ２ The part is R １ａ -L １ It may be the same as the part, or it may be different.

[0074] [R ３ａ -L ３ [Structure of the part] In general formula 1, L ３ is O or NR３ｂ That is. L ３ is, L １ It may be the same as, or it may be different from. L ３ is, L ２ It may be the same as, or it may be different from.

[0075] R ３ａ R １ａ It may be the same as, or it may be different from. ３ａ R ２ａ It may be the same as, or it may be different from. In one embodiment, R １ａ , R ２ａ and R ３ａ This is an unsubstituted phenyl compound.

[0076] L ３ If O, then R ３ａ Here, is a phenyl group, which may be substituted with 1 to 3 alkyl groups, more preferably 1 or 2 alkyl groups, and even more preferably 1 alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0077] L ３ NR ３ｂ If so, R ３ａ and R ３ｂ It has the following structure 3a or structure 3b.

[0078] <Structure 3a> R ３ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ３ｂ This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0079] The above aryl group is preferably a phenyl group.

[0080] The number of carbon atoms in the aryl group is preferably 6 to 8, more preferably 6 or 7, and even more preferably 6. The number of carbon atoms in the cycloalkyl group is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more.

[0081] The number of carbon atoms in the above cycloalkyl group is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. The number of carbon atoms in the above cycloalkyl group is particularly preferably 6.

[0082] The number of carbon atoms constituting the ring of the above cycloalkyl group is preferably 5 to 8, more preferably 6 or 7, and even more preferably 6.

[0083] The number of alkyl groups present as substituents in the above aryl group or cycloalkyl group is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0084] R ３ａ If the alkyl group is substituted with an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0085] R ３ｂ If the alkyl group is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0086] <Structure 3b> R ３ａ and R ３ｂ Each of them is a linear alkyl group and R ３ａ and R ３ｂ They combine, L ３ The nitrogen atom and R inside ３ａ and R ３ｂThese combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms. The number of carbon atoms is preferably 3 or more, more preferably 4 or more. Furthermore, the number of carbon atoms is preferably 8 or less, more preferably 7 or less. Even more preferably 6 or less. Particularly preferably, the number of carbon atoms is 5.

[0087] Here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ It may be replaced by O to form a nitrogen-containing oxygen-containing aliphatic monocyclic group.

[0088] Here, a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group. In one embodiment, the nitrogen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms. In one embodiment, the nitrogen-containing oxygen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms.

[0089] Here, the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, preferably one alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0090] Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, and more preferably 2 alkyl groups. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0091] Here, the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, preferably 1 to 4 alkyl groups, and more preferably 1 or 2 alkyl groups. Here, the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. Here, in the nitrogen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing condensed ring group is substituted with two or more alkyl groups, they may be bonded to both the nitrogen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing aliphatic ring portion and one or more alkyl groups may be bonded to the benzene ring portion, so that the total number of alkyl groups is two or more. Also, in the nitrogen-containing oxygen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing oxygen-containing condensed ring group is substituted with two or more alkyl groups, alkyl groups may be bonded to both the nitrogen-containing oxygen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion, and one or more alkyl groups may be bonded to the benzene ring portion, resulting in a total of two or more alkyl groups.

[0092] [R ３ａ -L ３ [Relationship between parts] L ３ is, L １ It may be the same as, or it may be different from. L ３ is, L ２ It may be the same as, or it may be different from. ３ａ R １ａ It may be the same as, or it may be different from. ３ａ R ２ａ It may be the same as, or it may be different from. ３ａ -L ３ The part is R １ａ -L １It may be the same as the part, or it may be different. ３ａ -L ３ The part is R ２ａ -L ２ It may be the same as the part, or it may be different.

[0093] [R １０ [Structure] In general formula 2, R １０ R is a phenylene group, where the phenylene group may be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, more preferably 1 alkyl group, where the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 or 2, more preferably 1. Preferably, R １０ R is a metaphenylene group which may be substituted with one to three alkyl groups or a paraphenylene group which may be substituted with one to three alkyl groups. More preferably, １０ This is an unsubstituted metaphenylene group or an unsubstituted paraphenylene group.

[0094] [R １１ａ -L １１ [Partial Structure] L １１ is O or NR １１ｂ That is the case.

[0095] L １１ If O, then R １１ａ Here, is a phenyl group, which may be substituted with 1 to 3 alkyl groups, more preferably 1 or 2 alkyl groups, and even more preferably 1 alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0096] L １１ NR １１ｂ If so, R １１ａ and R １１ｂ It has the following structure 4a or structure 4b.

[0097] <Structure 4a> R １１ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １１ｂ This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0098] The above aryl group is preferably a phenyl group.

[0099] The number of carbon atoms in the aryl group is preferably 6 to 8, more preferably 6 or 7, and even more preferably 6. The number of carbon atoms in the cycloalkyl group is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more.

[0100] The number of carbon atoms in the above cycloalkyl group is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. The number of carbon atoms in the above cycloalkyl group is particularly preferably 6.

[0101] The number of carbon atoms constituting the ring of the above cycloalkyl group is preferably 5 to 8, more preferably 6 or 7, and even more preferably 6.

[0102] The number of alkyl groups present as substituents in the above aryl group or cycloalkyl group is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0103] R １１ａ If the alkyl group is substituted with an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0104] R １１ｂ If the alkyl group is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0105] <Structure 4b> R １１ａ and R １１ｂ Each of them is a linear alkyl group and R １１ａ and R １１ｂ They combine, L １１ The nitrogen atom and R inside １１ａ and R １１ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms. The number of carbon atoms is preferably 3 or more, more preferably 4 or more. Furthermore, the number of carbon atoms is preferably 8 or less, more preferably 7 or less. Even more preferably 6 or less. Particularly preferably, the number of carbon atoms is 5.

[0106] Here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ It may be replaced by O to form a nitrogen-containing oxygen-containing aliphatic monocyclic group.

[0107] Here, a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group. In one embodiment, the nitrogen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms. In one embodiment, the nitrogen-containing oxygen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms.

[0108] Here, the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, preferably one alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0109] Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, and more preferably 2 alkyl groups. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0110] Here, the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, preferably 1 to 4 alkyl groups, and more preferably 1 or 2 alkyl groups. Here, the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. Here, in the nitrogen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing condensed ring group is substituted with two or more alkyl groups, they may be bonded to both the nitrogen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing aliphatic ring portion and one or more alkyl groups may be bonded to the benzene ring portion, so that the total number of alkyl groups is two or more. Also, in the nitrogen-containing oxygen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing oxygen-containing condensed ring group is substituted with two or more alkyl groups, alkyl groups may be bonded to both the nitrogen-containing oxygen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion, and one or more alkyl groups may be bonded to the benzene ring portion, resulting in a total of two or more alkyl groups.

[0111] [R １２ａ -L １２ [Partial Structure] L １２ is O or NR １２ｂ That is the case.

[0112] L １２ If O, then R １２ａ Here, is a phenyl group, which may be substituted with 1 to 3 alkyl groups, more preferably 1 or 2 alkyl groups, and even more preferably 1 alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0113] L １２ NR １２ｂ If so, R １２ａ and R １２ｂ It has the following structure 5a or structure 5b.

[0114] <Structure 5a> R １２ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １２ｂ This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0115] The above aryl group is preferably a phenyl group.

[0116] The number of carbon atoms in the aryl group is preferably 6 to 8, more preferably 6 or 7, and even more preferably 6. The number of carbon atoms in the cycloalkyl group is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more.

[0117] The number of carbon atoms in the above cycloalkyl group is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. The number of carbon atoms in the above cycloalkyl group is particularly preferably 6.

[0118] The number of carbon atoms constituting the ring of the above cycloalkyl group is preferably 5 to 8, more preferably 6 or 7, and even more preferably 6.

[0119] The number of alkyl groups present as substituents in the above aryl group or cycloalkyl group is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0120] R １２ａ If the alkyl group is substituted with an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0121] R １２ｂ If the alkyl group is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0122] <Structure 5b> R １２ａ and R １２ｂ Each of them is a linear alkyl group and R １２ａ and R １２ｂ They combine, L １２ The nitrogen atom and R inside １２ａ and R １２ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms. The number of carbon atoms is preferably 3 or more, more preferably 4 or more. Furthermore, the number of carbon atoms is preferably 8 or less, more preferably 7 or less. Even more preferably 6 or less. Particularly preferably, the number of carbon atoms is 5.

[0123] Here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ It may be replaced by O to form a nitrogen-containing oxygen-containing aliphatic monocyclic group.

[0124] Here, a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group. In one embodiment, the nitrogen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms. In one embodiment, the nitrogen-containing oxygen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms.

[0125] Here, the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, preferably one alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0126] Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, and more preferably 2 alkyl groups. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0127] Here, the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, preferably 1 to 4 alkyl groups, and more preferably 1 or 2 alkyl groups. Here, the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. Here, in the nitrogen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing condensed ring group is substituted with two or more alkyl groups, they may be bonded to both the nitrogen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing aliphatic ring portion and one or more alkyl groups may be bonded to the benzene ring portion, so that the total number of alkyl groups is two or more. Also, in the nitrogen-containing oxygen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing oxygen-containing condensed ring group is substituted with two or more alkyl groups, alkyl groups may be bonded to both the nitrogen-containing oxygen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion, and one or more alkyl groups may be bonded to the benzene ring portion, resulting in a total of two or more alkyl groups.

[0128] [R １２ａ -L １２ [Relationship between parts] L １２ is, L １１ It may be the same as, or it may be different from. １２ａ R １１ａ It may be the same as, or it may be different from. １２ａ -L １２ The part is R １１ａ -L １１ It may be the same as the part, or it may be different.

[0129] [L １３ [Structure] L １３ is O or NR １３ｂIt is. Preferably, it is O. L １３ is, L １１ It may be the same as, or it may be different from. L １３ is, L １２ It may be the same as, or it may be different from.

[0130] R １３ｂ These are hydrogen atoms or linear or branched alkyl groups having 1 to 4 carbon atoms.

[0131] [L １４ [Structure] L １４ is O or NR １４ｂ It is. Preferably, it is O. L １４ is, L １１ It may be the same as, or it may be different from. L １４ is, L １２ It may be the same as, or it may be different from. L １４ is, L １３ It may be the same as, or it may be different. Preferably, L １４ is, L １３ It is the same as L. １３ and L １４ Both are O.

[0132] R １４ｂ These are hydrogen atoms or linear or branched alkyl groups having 1 to 4 carbon atoms.

[0133] [R １５ａ -L １５ [Structure of the parts]

[0134] L １５ is O or NR １５ｂ That is the case.

[0135] L １５ If O, then R １５ａHere, is a phenyl group, which may be substituted with 1 to 3 alkyl groups, more preferably 1 or 2 alkyl groups, and even more preferably 1 alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0136] L １５ NR １５ｂ If so, R １５ａ and R １５ｂ It has the following structure 6a or structure 6b.

[0137] <Structure 6a> R １５ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １５ｂ This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0138] The above aryl group is preferably a phenyl group.

[0139] The number of carbon atoms in the aryl group is preferably 6 to 8, more preferably 6 or 7, and even more preferably 6. The number of carbon atoms in the cycloalkyl group is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more.

[0140] The number of carbon atoms in the above cycloalkyl group is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. The number of carbon atoms in the above cycloalkyl group is particularly preferably 6.

[0141] The number of carbon atoms constituting the ring of the above cycloalkyl group is preferably 5 to 8, more preferably 6 or 7, and even more preferably 6.

[0142] The number of alkyl groups present as substituents in the above aryl group or cycloalkyl group is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0143] R １５ａ If the alkyl group is substituted with an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0144] R １５ｂ If the alkyl group is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0145] <Structure 6b> R １５ａ and R １５ｂ Each of them is a linear alkyl group and R １５ａ and R １５ｂ They combine, L １５ The nitrogen atom and R inside １５ａ and R １５ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms. The number of carbon atoms is preferably 3 or more, more preferably 4 or more. Furthermore, the number of carbon atoms is preferably 8 or less, more preferably 7 or less. Even more preferably 6 or less. Particularly preferably, the number of carbon atoms is 5.

[0146] Here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ It may be replaced by O to form a nitrogen-containing oxygen-containing aliphatic monocyclic group.

[0147] Here, a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group. In one embodiment, the nitrogen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms. In one embodiment, the nitrogen-containing oxygen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms.

[0148] Here, the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, preferably one alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0149] Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, and more preferably 2 alkyl groups. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0150] Here, the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, preferably 1 to 4 alkyl groups, and more preferably 1 or 2 alkyl groups. Here, the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. Here, in the nitrogen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing condensed ring group is substituted with two or more alkyl groups, they may be bonded to both the nitrogen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing aliphatic ring portion and one or more alkyl groups may be bonded to the benzene ring portion, so that the total number of alkyl groups is two or more. Also, in the nitrogen-containing oxygen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing oxygen-containing condensed ring group is substituted with two or more alkyl groups, alkyl groups may be bonded to both the nitrogen-containing oxygen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion, and one or more alkyl groups may be bonded to the benzene ring portion, resulting in a total of two or more alkyl groups.

[0151] [R １５ａ -L １５ [Relationship between parts] L １５ is, L １１ It may be the same as, or it may be different from. L １５ is, L １２ It may be the same as, or it may be different. Preferably, L １５ is, L １２ It is the same as R. １５ａ R １１ａ It may be the same as, or it may be different from. １５ａ R １２ａ It may be the same as, or it may be different from. Preferably, R １５ａ R １２ａIt is the same as R １５ａ -L １５ The part is R １１ａ -L １１ It may be the same as the part, or it may be different. １５ａ -L １５ The part is R １２ａ -L １２ It may be the same as the part, or it may be different. Preferably, R １５ａ -L １５ The part is R １２ａ -L １２ It is the same as the part.

[0152] [R １６ａ -L １６ [Partial Structure] L １６ is O or NR １６ｂ That is the case.

[0153] L １６ If O, then R １６ａ Here, is a phenyl group, which may be substituted with 1 to 3 alkyl groups, more preferably 1 or 2 alkyl groups, and even more preferably 1 alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0154] L １６ NR １６ｂ If so, R １６ａ and R １６ｂ It has the following structure 7a or structure 7b.

[0155] <Structure 7a> R １６ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １６ｂ This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0156] The above aryl group is preferably a phenyl group.

[0157] The number of carbon atoms in the aryl group is preferably 6 to 8, more preferably 6 or 7, and even more preferably 6. The number of carbon atoms in the cycloalkyl group is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more.

[0158] The number of carbon atoms in the above cycloalkyl group is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. The number of carbon atoms in the above cycloalkyl group is particularly preferably 6.

[0159] The number of carbon atoms constituting the ring of the above cycloalkyl group is preferably 5 to 8, more preferably 6 or 7, and even more preferably 6.

[0160] The number of alkyl groups present as substituents in the above aryl group or cycloalkyl group is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0161] R １６ａ If the alkyl group is substituted with an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0162] R １６ｂ If the alkyl group is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0163] <Structure 7b> R １６ａ and R １６ｂ Each of them is a linear alkyl group and R １６ａ and R １６ｂ They combine, L １６ The nitrogen atom and R inside １６ａ and R １６ｂThese combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms. The number of carbon atoms is preferably 3 or more, more preferably 4 or more. Furthermore, the number of carbon atoms is preferably 8 or less, more preferably 7 or less. Even more preferably 6 or less. Particularly preferably, the number of carbon atoms is 5.

[0164] Here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ It may be replaced by O to form a nitrogen-containing oxygen-containing aliphatic monocyclic group.

[0165] Here, a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group. In one embodiment, the nitrogen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms. In one embodiment, the nitrogen-containing oxygen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms.

[0166] Here, the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, preferably one alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0167] Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, and more preferably 2 alkyl groups. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0168] Here, the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, preferably 1 to 4 alkyl groups, and more preferably 1 or 2 alkyl groups. Here, the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. Here, in the nitrogen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing condensed ring group is substituted with two or more alkyl groups, they may be bonded to both the nitrogen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing aliphatic ring portion and one or more alkyl groups may be bonded to the benzene ring portion, so that the total number of alkyl groups is two or more. Also, in the nitrogen-containing oxygen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing oxygen-containing condensed ring group is substituted with two or more alkyl groups, alkyl groups may be bonded to both the nitrogen-containing oxygen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion, and one or more alkyl groups may be bonded to the benzene ring portion, resulting in a total of two or more alkyl groups.

[0169] [R １６ａ -L １６ [Relationship between parts] L １６ is, L １１ It may be the same as, or it may be different. Preferably, L １６ is, L １１ It is the same as L １６ is, L １２ It may be the same as, or it may be different from. L １６ is, L １５ It may be the same as, or it may be different from.

[0170] R １６ａ R １１ａ It may be the same as, or it may be different from. Preferably, R１６ａ R １１ａ It is the same as R １６ａ R １２ａ It may be the same as, or it may be different from. １６ａ R １５ａ It may be the same as, or it may be different from.

[0171] R １６ａ -L １６ The part is R １１ａ -L １１ It may be the same as the part, or it may be different. Preferably, R １６ａ -L １６ The part is R １１ａ -L １１ It is the same as part R １６ａ -L １６ The part is R １２ａ -L １２ It may be the same as the part, or it may be different. １６ａ -L １６ The part is R １５ａ -L １５ It may be the same as the part, or it may be different.

[0172] [Phosphorus-nitrogen single bonds in compounds] In compounds of general formula 1, one phosphorus atom has one phosphorus-nitrogen single bond (a single bond between a phosphorus atom and a nitrogen atom) and two phosphorus-oxygen single bonds (a single bond between a phosphorus atom and an oxygen atom), or two phosphorus-nitrogen single bonds and one phosphorus-oxygen single bond, or three phosphorus-nitrogen single bonds. It is preferable that one phosphorus atom has one phosphorus-nitrogen single bond and two phosphorus-oxygen single bonds.

[0173] In general formula 2, n １０ If is 1, then L １１ ~L １３ Two of them are O, L １１ ~L １３ One of them is a nitrogen-containing group (i.e., L １１ NR １１ L １２ NR １２ is or L １３ NR １３ That is.), and L １４ ~L１６ Two of them are O, L １４ ~L １６ One of them is a nitrogen-containing group (i.e., L １４ NR １４ L １５ NR １５ is or L １６ NR １６ (That is.) In other words, in general formula 2, n １０ When n is 1, each of the two phosphorus atoms has one phosphorus nitrogen single bond and two phosphorus oxygen single bonds. Similarly, n １０ When the number is between 2 and 6, each of the 3 to 7 phosphorus atoms has one phosphorus nitrogen single bond and two phosphorus oxygen single bonds.

[0174] [Preferred Ring Structures] Compounds of general formula 1 have three ring structures. Preferably, each of the three ring structures is either a six-membered ring or a fused ring formed by the fusion of a six-membered ring and a benzene ring. In one embodiment, all three ring structures are six-membered rings. In another embodiment, two of the ring structures are six-membered rings, and one of the ring structures is a fused ring formed by the fusion of a six-membered ring and a benzene ring.

[0175] The compound of general formula 2 has five ring structures. Preferably, each of the five ring structures is either a six-membered ring or a fused ring formed by the fusion of a six-membered ring and a benzene ring. In one embodiment, all five ring structures are six-membered rings. In another embodiment, four of the ring structures are six-membered rings and one of the ring structures is a fused ring formed by the fusion of a six-membered ring and a benzene ring. In yet another embodiment, three of the ring structures are six-membered rings and two of the ring structures are fused rings formed by the fusion of a six-membered ring and a benzene ring.

[0176] In one embodiment, one to three nitrogen atoms in the compound of general formula 1 are each bonded to an unsubstituted phenyl group or an unsubstituted cyclohexyl group, preferably an unsubstituted phenyl group. In another embodiment, two nitrogen atoms in the compound of general formula 2 are each bonded to an unsubstituted phenyl group or an unsubstituted cyclohexyl group, preferably an unsubstituted phenyl group.

[0177] In one embodiment, each of the one to three nitrogen atoms bonded to the phosphorus atom in the compound of general formula 1 is either one of the six ring atoms forming a six-membered ring, or one of the ring atoms in the six-membered ring portion of a fused ring formed by the condensation of a six-membered ring with a benzene ring. Preferably, in the compound of general formula 1, there is one nitrogen atom bonded to the phosphorus atom, which is either one of the six ring atoms forming a six-membered ring, or one of the ring atoms in the six-membered ring portion of a fused ring formed by the condensation of a six-membered ring with a benzene ring, and more preferably, one of the six ring atoms forming a six-membered ring.

[0178] In one embodiment, each of the two nitrogen atoms bonded to the two phosphorus atoms in the compound of general formula 2 is either one of the six ring atoms forming a six-membered ring, or one of the ring atoms of the six-membered ring portion of a fused ring formed by the condensation of a six-membered ring with a benzene ring.

[0179] [Symmetry of the structure of the compound of general formula 2] The structure of the compound of general formula 2 may be bilaterally symmetrical or not. It is preferable to have a structure that is close to bilaterally symmetrical, and more preferable to have a bilaterally symmetrical structure.

[0180] In one embodiment, R １１ａ , R １２ａ , R １５ａ and R １６ａ In one embodiment, where all are identical, R １１ａ , R １２ａ , R １５ａ and R １６ａ This is an unsubstituted phenyl compound.

[0181] In one embodiment, L １３ and L １４ The same, preferably L １３ and L １４ The answer is O.

[0182] In one embodiment, L １１ and L １６ The same, and L １２ and L１５ They are the same. In one embodiment, L １２ ~L １５ They are the same, preferably L １２ ~L １５ The answer is O.

[0183] In one embodiment, L １１ NR １１ｂ And L １６ NR １６ｂ And here, preferably, NR １１ｂ and NR １６ｂ They are identical. More preferably, L １１ and L １６ That is NH.

[0184] In a more preferred embodiment, the structure of the compound of general formula 2 is symmetrical. That is, L １１ and L １６ They are identical, R １１ａ and R １６ａ They are identical, L １２ and L １５ They are identical, R １２ａ and R １５ａ They are identical, and L １３ and L １４ It is preferable that they are the same.

[0185] [Repeating Unit] In General Equation 2, n １０ n is an integer between 1 and 6, preferably between 1 and 4, more preferably between 1 and 2, and particularly preferably 1. １０ = A mixture of multiple compounds selected from 1 to 6 may be used. １０ = One compound selected from 1 to 6 may be used alone.

[0186] [Compound of the present invention] The compound of the present invention is the following general formula 2A: It has a structure represented by the following:

[0187] The compound of general formula 2A corresponds to the compound of general formula 2 described above. R in the compound of general formula 2A ２０ , R ２１ａ , R ２１ｂ , R２２ａ , R ２５ａ , R ２６ａ and R ２６ｂ These are, respectively, the R in the compound of the general formula 2 described above. １０ , R １１ａ , R １１ｂ , R １２ａ , R １５ａ , R １６ａ and R １６ｂ This corresponds to the above. However, in the compound of general formula 2A, some of the substituent options in the compound of general formula 2 have been removed. Therefore, in the compound of general formula 2A, the above explanation for the compound of general formula 2 also applies to the compound of general formula 2A, except that some of the substituent options in general formula 2 have been removed.

[0188] In general formula 2A, R ２０ R is a phenylene group, where the phenylene group may be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, more preferably 1 alkyl group, where the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 or 2, more preferably 1. Preferably, R ２０ R is a metaphenylene group which may be substituted with one to three alkyl groups or a paraphenylene group which may be substituted with one to three alkyl groups. More preferably, ２０ This is an unsubstituted metaphenylene group or an unsubstituted paraphenylene group.

[0189] R ２１ａ and R ２１ｂ It has the following structure 8a or structure 8b.

[0190] <Structure 8a> R ２１ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ２１ｂThis is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0191] The above aryl group is preferably a phenyl group.

[0192] The number of carbon atoms in the aryl group is preferably 6 to 8, more preferably 6 or 7, and even more preferably 6. The number of carbon atoms in the cycloalkyl group is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more.

[0193] The number of carbon atoms in the above cycloalkyl group is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. The number of carbon atoms in the above cycloalkyl group is particularly preferably 6.

[0194] The number of carbon atoms constituting the ring of the above cycloalkyl group is preferably 5 to 8, more preferably 6 or 7, and even more preferably 6.

[0195] The number of alkyl groups present as substituents in the above aryl group or cycloalkyl group is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0196] R ２１ａ If the alkyl group is substituted with an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0197] R ２１ｂ If the alkyl group is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0198] <Structure 8b> R ２１ａ and R ２１ｂ Each of them is a linear alkyl group and R ２１ａ and R ２１ｂ The nitrogen atom and R bond together. ２１ａ and R ２１ｂThese combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms. The number of carbon atoms is preferably 3 or more, more preferably 4 or more. Furthermore, the number of carbon atoms is preferably 8 or less, more preferably 7 or less. Even more preferably 6 or less. Particularly preferably, the number of carbon atoms is 5.

[0199] Here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ It may be replaced by O to form a nitrogen-containing oxygen-containing aliphatic monocyclic group.

[0200] Here, a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group. In one embodiment, the nitrogen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms. In one embodiment, the nitrogen-containing oxygen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms.

[0201] Here, the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, preferably one alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0202] Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, and more preferably 2 alkyl groups. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0203] Here, the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, preferably 1 to 4 alkyl groups, and more preferably 1 or 2 alkyl groups. Here, the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. Here, in the nitrogen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing condensed ring group is substituted with two or more alkyl groups, they may be bonded to both the nitrogen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing aliphatic ring portion and one or more alkyl groups may be bonded to the benzene ring portion, so that the total number of alkyl groups is two or more. Also, in the nitrogen-containing oxygen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing oxygen-containing condensed ring group is substituted with two or more alkyl groups, alkyl groups may be bonded to both the nitrogen-containing oxygen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion, and one or more alkyl groups may be bonded to the benzene ring portion, resulting in a total of two or more alkyl groups.

[0204] [R ２２ａ and R ２５ａ [Structure] R ２２ａ Here, is a phenyl group, which may be substituted with 1 to 3 alkyl groups, more preferably 1 or 2 alkyl groups, and even more preferably 1 alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0205] R ２５ａHere, is a phenyl group, which may be substituted with 1 to 3 alkyl groups, more preferably 1 or 2 alkyl groups, and even more preferably 1 alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0206] [R ２２ａ or R ２５ａ [Relationship with other substituents] R ２２ａ R ２１ａ It may be the same as, or it may be different from.

[0207] R ２５ａ R ２１ａ It may be the same as, or it may be different from. ２５ａ R ２２ａ It may be the same as, or it may be different from. Preferably, R ２５ａ R ２２ａ It's the same.

[0208] [R ２６ａ and R ２６ｂ [Structure] R ２６ａ and R ２６ｂ It has the following structure 9a or structure 9b.

[0209] <Structure 9a> R ２６ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ２６ｂ This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0210] The above aryl group is preferably a phenyl group.

[0211] The number of carbon atoms in the aryl group is preferably 6 to 8, more preferably 6 or 7, and even more preferably 6. The number of carbon atoms in the cycloalkyl group is preferably 4 or more, more preferably 5 or more, and even more preferably 6 or more.

[0212] The number of carbon atoms in the above cycloalkyl group is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. The number of carbon atoms in the above cycloalkyl group is particularly preferably 6.

[0213] The number of carbon atoms constituting the ring of the above cycloalkyl group is preferably 5 to 8, more preferably 6 or 7, and even more preferably 6.

[0214] The number of alkyl groups present as substituents in the above aryl group or cycloalkyl group is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0215] R ２６ａ If the alkyl group is substituted with an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0216] R ２６ｂ If the alkyl group is an alkyl group, the number of carbon atoms in the alkyl group is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0217] <Structure 9b> R ２６ａ and R ２６ｂ Each of them is a linear alkyl group and R ２６ａ and R ２６ｂ The nitrogen atom and R bond together. ２６ａ and R ２６ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms. The number of carbon atoms is preferably 3 or more, more preferably 4 or more. Furthermore, the number of carbon atoms is preferably 8 or less, more preferably 7 or less. Even more preferably 6 or less. Particularly preferably, the number of carbon atoms is 5.

[0218] Here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ It may be replaced by O to form a nitrogen-containing oxygen-containing aliphatic monocyclic group.

[0219] Here, a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group. In one embodiment, the nitrogen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms. In one embodiment, the nitrogen-containing oxygen-containing aliphatic monocyclic group is a six-membered ring and condenses with a benzene ring to form a condensed ring structure in which two six-membered rings share two carbon atoms.

[0220] Here, the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, preferably one alkyl group. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0221] Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, preferably 1 or 2 alkyl groups, and more preferably 2 alkyl groups. Here, the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0222] Here, the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, preferably 1 to 4 alkyl groups, and more preferably 1 or 2 alkyl groups. Here, the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms, where the number of carbon atoms is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. Here, in the nitrogen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing condensed ring group is substituted with two or more alkyl groups, they may be bonded to both the nitrogen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing aliphatic ring portion and one or more alkyl groups may be bonded to the benzene ring portion, so that the total number of alkyl groups is two or more. Also, in the nitrogen-containing oxygen-containing condensed ring group, the substituted alkyl group may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion or to the benzene ring portion. If the nitrogen-containing oxygen-containing condensed ring group is substituted with two or more alkyl groups, alkyl groups may be bonded to both the nitrogen-containing oxygen-containing aliphatic ring portion and the benzene ring portion. That is, one or more alkyl groups may be bonded to the nitrogen-containing oxygen-containing aliphatic ring portion, and one or more alkyl groups may be bonded to the benzene ring portion, resulting in a total of two or more alkyl groups.

[0223] [R ２６ａ or R ２６ｂ [Relationship with other substituents] R ２６ａ R ２１ａ It may be the same as, or it may be different from. Preferably, R ２６ａ R ２１ａ It is the same as R ２６ａ R ２２ａ It may be the same as, or it may be different from. ２６ａ R ２５ａ It may be the same as, or it may be different from.

[0224] R ２６ｂ R ２１ｂ It may be the same as, or it may be different from. Preferably, R２６ｂ R ２１ｂ It is the same as this.

[0225] [Repeating Unit] In general formula 2A, n ２０ n is an integer between 1 and 6, preferably between 1 and 4, more preferably between 1 and 2, and particularly preferably 1. ２０ = A mixture of multiple compounds selected from 1 to 6 may be used. ２０ = One compound selected from 1 to 6 may be used alone.

[0226] [Compounds excluded from general formula 2A] However, in general formula 2A, the following compounds are excluded from the compounds of the present invention: ・n ２０ If R is 1, ２０ is an unsubstituted phenylene group, with two oxygen atoms bonded to the 1st and 3rd positions of the phenylene group (i.e., the first oxygen atom and the second oxygen atom are in the meta position), R ２１ａ is an unsubstituted phenyl group, R ２１ｂ is hydrogen and R ２２ａ and R ２５ａ is a 2,6-dimethylphenyl group, R ２６ａ is an unsubstituted phenyl group, and R ２６ｂ Compounds in which hydrogen is present. ２０ If R is 1, ２０ A phenylene group substituted with two tert-butyl groups, wherein two oxygen atoms are bonded to the 1st and 4th positions of the phenylene group (i.e., the first oxygen atom and the second oxygen atom are in the para position), and the two tert-butyl groups are bonded to the 2nd and 5th positions of the phenylene group (i.e., the first oxygen atom and the first tert-butyl group are in the ortho position, and the first tert-butyl group and the second tert-butyl group are in the para position), R ２１ａ is an unsubstituted phenyl group, R ２１ｂ is hydrogen and R ２２ａ and R ２５ａ is a 2,6-dimethylphenyl group, R ２６ａ is an unsubstituted phenyl group, and R ２６ｂ Compounds in which hydrogen is present.２０ If R is 1 or 2, ２０ is an unsubstituted phenylene group, with two oxygen atoms bonded to the 1st and 3rd positions of the phenylene group (i.e., the first oxygen atom and the second oxygen atom are in the meta position), R ２１ａ and R ２１ｂ It combines with the nitrogen atom to form a morpholino group, R ２６ａ and R ２６ｂ It combines with the nitrogen atom to form a morpholino group, and R ２２ａ is an unsubstituted phenyl group, R ２５ａ is an unsubstituted phenyl group, and R ２６ｂ Compounds in which hydrogen is present. These compounds are included in the compounds of general formula 2 and can be used as modifiers in the present invention.

[0227] [Modifiers using the compounds of the present invention] The compounds of the present invention described above can be used as modifiers as they are.

[0228] (Synthesis Method for Phosphoamide Compounds) Of the compounds used as modifiers in the present invention, known compounds can be synthesized using known methods. Novel compounds can be synthesized by combining known methods.

[0229] <Method for synthesizing monomeric compounds> The monomeric compounds represented by the above general formula 1 can be synthesized by known methods. For example, phosphorus oxyhalogenate and L in general formula 1. １ -R １ａ The cyclic amine compound that serves as the raw material for the part, and L in general formula 1 ２ -R ２ａ A cyclic amine compound or phenol compound that serves as a raw material for the part, and L in general formula 1 ３ -R ３ａ It can be synthesized by reacting a cyclic amine compound or phenol compound, which serves as a raw material for the part, with the compound.

[0230] Specifically, for example, monomeric compounds of general formula 1 are phosphorus oxyhalogenates of general formula 1X: (Here, X is a halogen, preferably chlorine or bromine.) to which: a cyclic amine compound represented by general formula 1-1, a phenol compound or cyclic amine compound represented by general formula 1-2, and a phenol compound or cyclic amine compound represented by general formula 1-3: R １ａ -L １ H (General formula 1-1) R ２ａ -L ２ H (General formula 1-2) R ３ａ -L ３ It can be obtained by reacting with H (general formula 1-3).

[0231] In one embodiment, L ２ or L ３ When is oxygen (when the compound of general formula 1-2 or the compound of general formula 1-3 is a phenol compound), it is preferable to react phosphorus oxyhalogenate with the phenol compound of general formula 1-2 or general formula 1-3 to prepare a phosphorhalidate corresponding to the compound of general formula 1, and then react the obtained phosphorhalidate with a cyclic amine compound (the compound of general formula 1-1 and the compound of general formula 1-2 or the compound of general formula 1-3) to obtain the compound of general formula 1. ２ and L ３ When the compound is oxygen (i.e., when the compounds of general formulas 1-2 and 1-3 are phenol compounds), it is preferable to react phosphorus oxyhalogenate with the phenol compounds of general formulas 1-2 and 1-3 to prepare a phosphorhalidate corresponding to the compound of general formula 1, and then react the obtained phosphorhalidate with a cyclic amine compound (a compound of general formula 1-1) to obtain the compound of general formula 1.

[0232] When reacting the phosphorhalidate with the amine compound, a catalyst (e.g., a pyridine compound such as 4-dimethylaminopyridine), an acidic gas scavenger (e.g., a trialkylamine such as triethylamine), or a solvent (e.g., toluene) may be used as needed.

[0233] <Method for synthesizing polymeric compounds> The polymeric compound represented by the above general formula 2 is, for example, made of phosphorus oxyhalogenate and L １３ -R １０ -L １４ It can be obtained by reacting a starting compound corresponding to R with a phenol compound corresponding to a phenol compound residue in the polymerized compound and an amine compound corresponding to an amine compound residue in the polymerized compound. For example, phosphorus oxyhalogenate and R １１ａ -L １１ , R １２ａ -L １２ , R １５ａ -L １５ and R １６ａ -L １６ The steps of preparing one or two phosphorhalidates by reacting them with a phenol compound corresponding to the phenol substituent among them, and the one or two phosphorhalidates obtained, in the L of general formula 2 １３ -R １０ -L １４ It is reacted with a divalent functional compound that serves as a raw material for the part, P-L １３ -R １０ -L １４ - A step of preparing a compound having a P skeleton, and the obtained P-L １３ -R １０ -L １４ - A compound having a P skeleton, １１ａ -L １１ , R １２ａ -L １２ , R １５ａ -L １５ and R １６ａ -L １６ It can be synthesized by a method that includes a step of reacting it with an amine compound corresponding to one of the amine substituents.

[0234] Specifically, for example, a compound of general formula 2 is a compound of general formula 210: HL １３ -R １０ -L １４ H (general formula 210) is used in compounds of general formula 212: (wherein X is a halogen, preferably chlorine or bromine.) and compounds of general formula 215: (Here, X is a halogen, preferably chlorine or bromine.) is reacted with a compound of general formula 217: (Here, n １０ The steps involve preparing a compound of general formula 217, and adding a compound of general formula 211: R １１ａ -L １１ Compounds of H (general formula 211) and general formula 216: R １６ａ -L １６ It can be prepared by a method that includes a step of reacting a compound of H (general formula 216).

[0235] The polymeric compound represented by the above general formula 2A can be obtained, for example, by reacting phosphorus oxyhalogenate, benzenediol, a phenol compound corresponding to the phenol compound residue in the polymeric compound, and an amine compound corresponding to the amine compound residue in the polymeric compound.

[0236] Compounds of general formula 2A are: Compound 2A20: HO-R ２０ -OH (general formula 2A20) and compounds of general formula 2A22: (Here, X is a halogen, preferably chlorine or bromine.) and compounds of general formula 2A25: (Here, X is a halogen, preferably chlorine or bromine. Also, the compound of general formula 2A22 may be the same as or different from the compound of general formula 2A25) is reacted to form the compound of general formula 2A27: (Here, n ２０ The steps involve preparing a compound of general formula 2A27 and an amine compound of general formula 2A21: and amine compounds of general formula 2A26: It can be prepared by a method that includes a step of reacting the two.

[0237] Furthermore, when a compound of general formula 2A20 is reacted with compounds of general formula 2A22 and general formula 2A25, and then with compounds of general formula 2A21 and general formula 2A26, in general formula 2, n １０ = In addition to compounds 1 to 6, n１０ A mixture containing compounds with = 0 may be obtained. This mixture may be used as a modifier without purification, or it may be purified to n １０ Compounds 1 to 6 (compounds of general formula 2) may be used after increasing their purity. For example, n １０ The compound with a purity of =1 may be used.

[0238] When synthesizing the compound of general formula 2A described above, a catalyst (e.g., a pyridine compound such as 4-dimethylaminopyridine), an acidic gas scavenger (e.g., a trialkylamine such as triethylamine), or a solvent (e.g., toluene) may be used as needed.

[0239] The above-mentioned compound can be used as is as a modifier in the present invention.

[0240] [Thermosetting Resin Composition] According to one embodiment of the present invention, a thermosetting resin composition for a circuit board is provided. This thermosetting resin composition comprises the above-mentioned modifier or compound and a thermosetting resin.

[0241] Preferably, the thermosetting resin includes an epoxy resin or a polyphenylene ether resin modified with ethylenically unsaturated groups.

[0242] The above thermosetting resin composition can be used to manufacture an insulating layer in a high-frequency printed circuit board.

[0243] The modifier is used to improve the dielectric properties of the thermosetting resin composition. The modifier may be a compound of general formula 1, a compound of general formula 2, or a compound of general formula 2A.

[0244] <Thermosetting Resin> Any known thermosetting resin used in the manufacture of circuit boards can be used in the thermosetting resin composition of the present invention. Examples include epoxy resins, modified polyphenylene ether resins, phenolic resins, and thermosetting polyimide resins. Preferably, it is an epoxy resin or a polyphenylene ether resin modified with ethylenically unsaturated groups. The thermosetting resin may be a thermosetting resin having ethylenically unsaturated bonds, or it may be a thermosetting resin without ethylenically unsaturated bonds.

[0245] <Epoxy Resin> In the present invention, any epoxy resin containing at least two epoxy groups in its molecule can be used as the epoxy resin. Examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, novolac type epoxy resin, biphenol type epoxy resin, and resorcinol type epoxy resin. The epoxy resin may also be a halogenated epoxy resin (e.g., a brominated epoxy resin). The epoxy resin used in the present invention is not particularly limited as long as it contains at least two or more epoxy groups in its molecule. Examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, or biphenol type epoxy resin or novolac type epoxy resin. The epoxy resin may also be a halogenated epoxy resin (e.g., a brominated epoxy resin). Any known epoxy resin curing agent can be used as the curing agent for the epoxy resin. For example, organic polyamines, organic acids, amino resins, phenolic resins, etc. Any known catalyst for catalyzing the curing reaction can be used with the epoxy resin.

[0246] In this specification, ethylenically unsaturated bonds refer to aliphatic double or triple bonds that can undergo radical polymerization in the presence of radicals. Well-known substituents that have such unsaturated bonds include acryloyl groups, methacryloyl groups, vinyl groups, allyl groups, and maleimide groups. Resins obtained by bonding these unsaturated groups to a resin become thermosetting resins having ethylenically unsaturated bonds and are therefore suitable for use in the present invention.

[0247] Conventional thermosetting resins having ethylenically unsaturated bonds can be used. For example, polyphenylene ether resins, maleimide resins, and styrene-based resins modified with ethylenically unsaturated groups can be used.

[0248] <Polyphenylene ether resin modified with ethylenically unsaturated groups> In one embodiment, the thermosetting resin is a polyphenylene ether resin modified with ethylenically unsaturated groups. A polyphenylene ether resin modified with ethylenically unsaturated groups is a resin in which ethylenically unsaturated groups are bonded to the ends of a polyphenylene ether resin.

[0249] A polyphenylene ether resin modified with ethylenically unsaturated groups is represented, for example, by the following general formula 3A.

[0250]

[0251] (General formula 3A) In general formula 3A, ethylenically unsaturated groups are bonded to the hydrogen atoms of the hydroxyl groups at both ends of the polyphenylene ether main chain. Here, in formula A, R ３１ ~R ５２ Each of these is independent and is either a hydrogen atom or a substituent. Examples of substituents include linear or branched alkyl groups with 1 to 8 carbon atoms, linear or branched alkenyl groups with 2 to 8 carbon atoms, linear or branched alkynyl groups with 2 to 8 carbon atoms, aryl groups, carboxyl groups, aldehyde groups, hydroxyl groups, and amino groups with 6 to 10 carbon atoms. Each of X, Y, and Z is independently a single bond, a carbonyl group (>C=O), a thiocarbonyl group (>C=S), or a methylene group (-CH₂). ２ -), ethylene group (dimethylene group) (-CH ２ -CH ２ -), isopropenyl group (-C(CH ３ ) ２ -), trimethylene group (-CH ２ -CH ２ -CH ２ -) or tetramethylene group (-CH ２ -CH ２ -CH２ -CH ２ -) etc. １ m is preferably 1 to 100, and more preferably 3 to 20. ２ The value is preferably 1 to 100, and more preferably 3 to 20.

[0252] In one embodiment, R ３６ , R ３７ , R ４０ , R ４１ , R ４２ , R ４３ , R ４６ , and R ４７ is hydrogen. In one embodiment, R ３４ , R ３５ , R ３８ , R ３９ , R ４４ , R ４５ , R ４８ , and R ４９ is alkyl, and in one embodiment, R ３４ , R ３５ , R ３８ , R ３９ , R ４４ , R ４５ , R ４８ , and R ４９ It is methyl.

[0253] In one embodiment, X and Z are carbonyl groups (>C=O) and Y is an isopropenyl group (-C(CH) ３ ) ２ -) Also, in one embodiment, X is a benzylene group (-C ６ H ４ CH ２ -), Y is an isopropenyl group (-C(CH ３ ) ２ -) and Z is a benzylene group (-CH ２ C ６ H ４ -)

[0254] In one embodiment, R ３３ and R ５２ is methyl. In one embodiment, R ３３ and R ５２ That is hydrogen.

[0255] In one embodiment, R ３１ , R ３２ , R ５０ and R ５１ That is hydrogen.

[0256] The molecular weight of the polyphenylene ether resin modified with ethylenically unsaturated groups is not particularly limited. For example, a number average molecular weight of 500 or more is preferred, and 1,000 or more is more preferred. Also, for example, a number average molecular weight of 10,000 or less is preferred, 7,000 or less is more preferred, and in one embodiment it is 5,000 or less. In one embodiment it is 3,000 or less. If the molecular weight is too low, the Tg of the cured product tends to be low, and the heat resistance tends to decrease. If the molecular weight is too high, the fluidity decreases, which may make it difficult to mold the cured product.

[0257] Specific examples of preferred resins include those with the following structures:

[0258]

[0259] A specific example of a resin product with such a structure is Noryl® SA9000 resin, manufactured by SABIC Japan LLC, which is commercially available.

[0260] Furthermore, resins with the following structures can also be used as preferred resins.

[0261]

[0262] A specific example of a resin product with such a structure is MEGTRON®, manufactured by Panasonic Corporation, which is commercially available.

[0263] Furthermore, in one embodiment, polyphenylene ethers described in Japanese Patent Publication No. 2003-515642, Japanese Patent Publication No. 2006-516297, Japanese Patent Application Publication No. 2013-23517, Japanese Patent Application Publication No. 2013-23519, WO2014 / 034103, Japanese Patent Application Publication No. 2019-194312, etc., can also be used in the present invention as thermosetting resins.

[0264] <Maleimide Resin> In one embodiment, a maleimide resin may be used as the thermosetting resin. Any known maleimide resin can be used. Specifically, examples include 4,4'-bismaleimidediphenylmethane, N,N'-p-phenylenebismaleimide, N,N'-m-phenylenebismaleimide, N,N'-m-phenylenebismaleimide, bisphenol A diphenyl ether bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethanebismaleimide, 1,6'-bismaleimide-(2,2,4-trimethyl)hexane, and N,N'-(sulfonyldi-p-phenylene)dimaleimide.

[0265] <Styrene-based resin> In one embodiment, a corresponding styrene-based resin in which allyl groups are bonded to the side chains of polystyrene can also be used as the thermosetting resin. For example, polymers having structural units represented by the following formula in their molecules are known and can be used in the present invention.

[0266]

[0267] Here, Z ａ R indicates an arylene group, ６１ ~R ６３ Each independently represents a hydrogen atom or an alkyl group, R ６４ ~R ６６ Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Specific examples of such styrene-based resins include ODV-XET(X03), ODV-XET(X04), and ODV-XET(X05) manufactured by Nippon Steel Chemical & Material Co., Ltd.

[0268] In the thermosetting resin composition of the present invention, a thermoplastic resin may be used in addition to the thermosetting resin as needed. However, in order to fully exhibit the effects of the present invention, it is preferable to use only a small amount of thermoplastic resin. The amount of thermoplastic resin is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of the thermosetting resin having ethylenically unsaturated bonds. In one embodiment, the thermosetting resin composition of the present invention does not contain a thermoplastic resin.

[0269] <Crosslinking Agent> The thermosetting resin composition of the present invention optionally contains a monomer compound having an ethylenically unsaturated bond as a crosslinking agent. The crosslinking agent having an ethylenically unsaturated bond copolymerizes with the thermosetting resin having an ethylenically unsaturated bond during the thermosetting reaction, providing good physical properties to the resulting cured product.

[0270] As the crosslinking agent, monomers known as crosslinking agents for thermosetting resins having ethylenically unsaturated bonds can be used. For example, triallyl isocyanurate, triallyl cyanurate, diallyl phthalate, and styrene can be used. Monomers having two or more ethylenically unsaturated bonds in one molecule are preferred, and monomers having three or more ethylenically unsaturated bonds in one molecule are more preferred. Furthermore, monomers having four or fewer ethylenically unsaturated bonds in one molecule are preferred. In one embodiment, the crosslinking agent is a monomer having three ethylenically unsaturated bonds in its molecule.

[0271] Examples of the ethylenically unsaturated bond-containing portion of the crosslinking agent include allyl groups, acryloyl groups, and methacryloyl groups. Allyl groups are preferred. The molecular weight of the crosslinking agent is preferably 100 or more, and more preferably 200 or more. The molecular weight of the crosslinking agent is preferably 700 or less, more preferably 500 or less, and even more preferably 300 or less.

[0272] The amount of crosslinking agent used is not particularly limited. Preferably, the amount of crosslinking agent used is 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and particularly preferably 10 parts by mass or more, per 100 parts by mass of the thermosetting resin having ethylenically unsaturated bonds in the thermosetting resin composition. If necessary, it is also possible to use 20 parts by mass or more, and even 30 parts by mass or more, per 100 parts by mass of the thermosetting resin having ethylenically unsaturated bonds.

[0273] The amount of crosslinking agent used is preferably 200 parts by mass or less, more preferably 150 parts by mass or less, and even more preferably 100 parts by mass or less, per 100 parts by mass of the thermosetting resin having ethylenically unsaturated bonds in the thermosetting resin composition. If necessary, it is also possible to use 120 parts by mass or less, or 100 parts by mass or less, per 100 parts by mass of the thermosetting resin having ethylenically unsaturated bonds.

[0274] If the amount of crosslinking agent used is too small, the cured product obtained by curing the thermosetting resin composition may not have sufficient heat resistance. If the amount of crosslinking agent used is too large, the cured product obtained by curing the thermosetting resin composition may not have sufficient tensile strength and impact strength.

[0275] While modifier compounds having ethylenically unsaturated bonds can also function as crosslinking agents, in this invention, modifier compounds having ethylenically unsaturated bonds exhibit a remarkable effect as modifiers. Therefore, in this specification, modifier compounds having ethylenically unsaturated bonds are not included as crosslinking agents.

[0276] <Radical Generator> The thermosetting resin composition of the present invention may optionally contain a radical generator. The radical generator may generate radicals when heated, or it may generate radicals when irradiated with light (for example, visible light or ultraviolet light).

[0277] As a radical generator, any compound known as a radical polymerization initiator for compounds having an ethylenically unsaturated bond can be used. For example, peroxide-based initiators, azo-based initiators, etc., can be used.

[0278] The amount of radical generator used is preferably 0.01 parts by mass or more, more preferably 0.05 parts by mass or more, even more preferably 0.1 parts by mass or more, and particularly preferably 0.5 parts by mass or more, per 100 parts by mass of the total amount of thermosetting resin and crosslinking agent. The amount of radical generator used is preferably 10 parts by mass or less, more preferably 7 parts by mass or less, and even more preferably 5 parts by mass or less, per 100 parts by mass of the total amount of thermosetting resin and crosslinking agent. If the amount of radical generator used is too small, it is likely to be difficult to sufficiently cure the thermosetting resin composition. If the amount of radical generator used is too large, the physical properties of the cured product obtained by curing the thermosetting resin composition may not be sufficient, leading to deterioration of electrical properties.

[0279] <Modifier> The thermosetting resin composition of the present invention uses the above-described phosphoramide compound as a modifier. In this specification, modification means improving the properties of a resin, and modifier means a compound added to a resin to improve the properties of the resin. The modifier of the present invention is effective in improving the properties of thermosetting resins, and in particular is effective in improving the properties of thermosetting resins having ethylenically unsaturated bonds. In one embodiment, the modifier of the present invention can improve the dielectric properties of a thermosetting resin composition. The modifier of the present invention is effective in improving either the dielectric loss tangent or the transmission loss of a thermosetting resin composition, and is also effective in improving both the dielectric loss tangent and the transmission loss. Therefore, the modifier of the present invention can be suitably used in thermosetting resin compositions for printed circuit boards. It can be suitably used in high-frequency printed circuit boards in particular. Furthermore, the modifier of the present invention can maintain the high heat resistance of the thermosetting resin composition.

[0280] The amount of modifier used is not particularly limited. Preferably, the amount of modifier used is 1 part by mass or more per 100 parts by mass of thermosetting resin, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and particularly preferably 10 parts by mass or more. If necessary, it is also possible to use 20 parts by mass or more per 100 parts by mass of thermosetting resin, and also 30 parts by mass or more.

[0281] The amount of modifier used is preferably 50 parts by mass or less, more preferably 40 parts by mass or less, and even more preferably 30 parts by mass or less, per 100 parts by mass of thermosetting resin in the thermosetting resin composition. If necessary, it is also possible to use 20 parts by mass or less, or even 10 parts by mass or less, per 100 parts by mass of thermosetting resin. If the amount of modifier used is too little or too much, sufficient physical properties may not be obtained in the cured product obtained by curing the thermosetting resin composition.

[0282] <Reinforcement Material> The thermosetting resin composition of the present invention may be used with a reinforcement material as needed.

[0283] As a reinforcing material, any known reinforcing material for thermosetting resins can be used. For example, fibrous reinforcing materials conventionally used as reinforcing materials for epoxy resins can be used. Specifically, for example, glass fibers can be used.

[0284] The reinforcing material may or may not be able to be uniformly mixed in the thermosetting resin composition. Examples of reinforcing materials that can be uniformly mixed in the thermosetting resin composition include short glass fibers, while examples of reinforcing materials that cannot be uniformly mixed in the thermosetting resin composition include long glass fibers.

[0285] For example, glass fibers can be formed into a sheet or mat and impregnated with a thermosetting resin composition to be used as a molding material in the form of a so-called prepreg.

[0286] The amount of reinforcing material used is not particularly limited. Specifically, for example, in a thermosetting resin composition, the amount of reinforcing material can be 1 part by mass or more, 10 parts by mass or more, 30 parts by mass or more, or 50 parts by mass or more, per 100 parts by mass of the total amount of thermosetting resin, crosslinking agent and modifier. Alternatively, in a thermosetting resin composition, the amount of reinforcing material can be 300 parts by mass or less, 200 parts by mass or less, 150 parts by mass or less, or 100 parts by mass or less, per 100 parts by mass of the total amount of thermosetting resin, crosslinking agent and modifier.

[0287] <Other Additives> The thermosetting resin composition of the present invention may further contain various additives other than the modifiers and reinforcing materials described above, depending on the desired properties of the resin composition, as long as they do not affect the effects of the present invention. For example, known flame retardants, flame retardant aids, ultraviolet absorbers, antioxidants, light stabilizers, colorants (e.g., dyes or pigments), surface modifiers, antibacterial agents, insecticides, antistatic agents, fillers (e.g., inorganic fillers), etc., can be added.

[0288] There are no particular limitations on the types and amounts of these additives; commonly used additives can be used within the range of normal usage. Specifically, for example, each of these additives can be added in amounts of 0.01 parts by mass or more per 100 parts by mass of thermosetting resin, or 0.1 parts by mass or more, or 1 part by mass or more, or 20 parts by mass or less, or 10 parts by mass or less, or 5 parts by mass or less.

[0289] However, the additives mentioned above, such as colorants, UV absorbers, hydrolysis inhibitors, and fillers, are not necessarily required in the thermosetting resin composition of the present invention. These additives only need to be used in the minimum amount required for the product to be manufactured from the target thermosetting resin.

[0290] <Method for preparing the composition> Mixing and stirring operations during the preparation of the thermosetting resin composition can be carried out using conventional stirring devices, such as various mills, Henschel mixers (FM mixers), etc. The order of addition does not matter as long as the various components can be mixed uniformly. All components may be placed in the stirring device at once and mixed and stirred. For example, it is also possible to mix the materials other than the radical generator first and then mix in the radical generator afterward.

[0291] <Thermosetting Reaction> In the thermosetting resin composition of the present invention, a curing reaction can be carried out by conventionally known methods. For example, if a radical generator is heated or irradiated with light to generate radicals, the generated radicals will cause a polymerization reaction of the ethylenically unsaturated bonds of the thermosetting resin, resulting in a cured resin product. Furthermore, if the thermosetting resin composition contains a crosslinking agent, the ethylenically unsaturated bonds of the thermosetting resin and the ethylenically unsaturated bonds of the crosslinking agent will undergo a polymerization reaction, resulting in a cured resin product. In addition, since the compound and modifier of the present invention also have ethylenically unsaturated groups, a polymerization reaction of the compound and modifier of the present invention will occur due to the radicals.

[0292] The conditions for curing the thermosetting resin composition are appropriately selected depending on the type and amount of radical generator used. For example, if a radical generator that decomposes relatively quickly and generates radicals even at room temperature is used, room temperature may be used. If a radical generator that cannot decompose quickly unless high temperature is used, high temperature is used. Specifically, the temperature for curing the thermosetting resin composition can be, for example, 80°C or higher, or 100°C or higher, or for example, 250°C or lower, or 230°C or lower. The heating time can be, for example, 1 minute or more, or 3 minutes or more, or for example, 120 minutes or less, or 90 minutes or less.

[0293] When a curing reaction is carried out with the thermosetting resin composition of the present invention, it is believed that a copolymer is formed containing residues of the thermosetting resin having ethylenically unsaturated bonds and residues of the compound of the present invention or the modifier of the present invention. Furthermore, when a curing reaction is carried out with the thermosetting resin composition of the present invention including a crosslinking agent, it is believed that a copolymer is formed containing residues of the thermosetting resin having ethylenically unsaturated bonds, residues of the compound of the present invention or the modifier of the present invention, and residues of the crosslinking agent. Because the copolymer thus formed has excellent dielectric properties and heat resistance, it is understood that substrates manufactured using the thermosetting resin composition of the present invention have excellent dielectric properties and heat resistance. Since the cured product obtained by curing the thermosetting resin composition of the present invention has excellent dielectric properties and heat resistance, it can be preferably used as a material for manufacturing printed circuit boards. In this specification, "resin material" refers to a cured product obtained by curing the thermosetting resin composition, which can be used for various applications.

[0294] Furthermore, regarding the chemical structure of the resin in the cured product, it is presumed that radical polymerization reactions occur at the ethylenically unsaturated bond portions of the molecules of each component in the thermosetting resin composition, resulting in a structure in which multiple molecules are bonded together. However, it is difficult to precisely identify this chemical structure. In particular, when there are multiple types of molecules having ethylenically unsaturated bonds, both homopolymerization and copolymerization are possible, making it difficult to precisely identify the chemical structure of the product. Even if it is theoretically possible, it would require a great deal of time and expense, making it impractical. Therefore, the composition of the thermosetting resin composition before the curing reaction is identified, and the cured product obtained by curing that composition is described using the so-called product-by-process expression.

[0295] <Molded Articles> The thermosetting resin composition of the present invention can be molded by any known method for molding thermosetting resins. By using a molding machine and molds appropriate to the desired molded article, the desired molded article can be easily obtained. For example, it is possible to obtain the desired molded article by performing molding and the curing reaction of the thermosetting resin by methods such as heating and pressing. In the thermosetting resin composition, the process of performing the curing reaction and the process of molding into the desired shape may be performed simultaneously or separately. The cured product obtained by performing the curing reaction first may be molded, or the curing reaction may be performed after the molding process.

[0296] The resulting molded product has the advantage of having excellent dielectric properties and minimal reduction in heat resistance due to the addition of modifiers.

[0297] <Printed Circuit Boards> By curing the thermosetting resin composition containing the thermosetting resin and modifier described above, a substrate usable for printed circuit boards can be obtained. Printed circuit boards typically have a conductive layer and an insulating layer. The modifier and thermosetting resin composition of the present invention can be used to form the insulating layer of a printed circuit board. According to one embodiment of the present invention, a high-frequency printed circuit board is provided.

[0298] In this specification, high frequency is not particularly limited, but is preferably 100 MHz or higher, 1 GHz or higher in one embodiment, and 10 GHz or higher in another embodiment. Furthermore, high frequency may be, for example, 100 GHz or lower, or 50 GHz or lower. In this specification, high-frequency printed circuit board means a printed circuit board used for such high frequencies. <Method for Manufacturing a High-Frequency Printed Circuit Board> According to one embodiment of the present invention, a method for manufacturing a high-frequency printed circuit board is provided. This manufacturing method is a method for manufacturing a high-frequency printed circuit board comprising a conductive layer and an insulating layer, and includes the step of curing the thermosetting resin composition to form the insulating layer.

[0299] The present invention will be described more specifically by the following synthesis examples and embodiments, but the present invention is not limited to the following embodiments.

[0300] In the following synthesis examples, examples, and comparative examples, the following compounds were used as raw materials: • Phosphorus oxychloride (manufactured by Tokyo Chemical Industry Co., Ltd.) • Phenyl dichlorophosphate (manufactured by Tokyo Chemical Industry Co., Ltd.) • Diphenyl chlorophosphate (manufactured by Tokyo Chemical Industry Co., Ltd.) • Resorcinol (manufactured by Tokyo Chemical Industry Co., Ltd.) • Aniline (manufactured by Tokyo Chemical Industry Co., Ltd.) • Hydroquinone (manufactured by Tokyo Chemical Industry Co., Ltd.) • 2,6-Dimethylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) • 2,6-Dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) • Cyclohexylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) • Piperidine (manufactured by Tokyo Chemical Industry Co., Ltd.) • Morpholine (manufactured by Tokyo Chemical Industry Co., Ltd.) • N-Methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) • 1,2,3,4-Tetrahydroquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) • 1,3-Diaminobenzene (manufactured by Tokyo Chemical Industry Co., Ltd.) • TPP (Triphenyl phosphate, manufactured by Daihachi Chemical Industry Co., Ltd.) CR-733S (aromatic condensation phosphate ester manufactured by Daihachi Chemical Industry Co., Ltd.).

[0301] [Synthesis Example] (Synthesis Example A1) <Synthesis of 2,6-Xylylphosphorodicloride> A 1 L four-necked flask equipped with a stirrer, thermometer, and hydrochloric acid recovery device (condenser connected to a water scrubber) was filled with 920 g (6.0 mol) of phosphorus oxychloride, 366.5 g (3.0 mol) of 2,6-dimethylphenol, and 0.72 g (0.0075 mol) of magnesium chloride as a catalyst. The resulting mixed solution was gradually heated from 20°C to 120°C over approximately 4 hours while stirring to allow the reaction to proceed, and the generated hydrogen chloride gas was recovered using a water scrubber. The mixture was then cooled to 90°C. Subsequently, the pressure inside the flask was gradually reduced to 20 kPa to remove unreacted phosphorus oxychloride and 2,6-dimethylphenol, as well as by-product hydrogen chloride, yielding 670 g of a reaction product mainly composed of 2,6-xylylphosphorodicloride. The reaction product was purified by vacuum distillation using a vacuum pump to obtain a main fraction of 532 g (yield 74.1%). The chlorine content of the main fraction was 29.9% by mass (theoretical value 29.7% by mass).

[0302] (Synthesis Example 1) <Synthesis of Phenylamidate Diphenyl Phosphate> Diphenylamide diphenylphosphate was synthesized according to Reference Example 8 of Japanese Patent Publication No. 2000-154277.

[0303] (Synthesis Example 2) <Synthesis of Phenyl Phosphate Diphenylamidate> Phenyl phosphate diphenylamidate was synthesized according to paragraph 0071 of Japanese Patent Application Publication No. 2006-322102.

[0304] (Synthesis Example 3) <Synthesis of Triphenylamidate Phosphate> Triphenylamide phosphate was synthesized according to Example 1 of Japanese Patent Publication No. 49-53241.

[0305] (Synthesis Example 4) <Synthesis of N-methylphenylamide diphenyl phosphate> Diphenyl phosphate N-methylphenylamide was synthesized according to Reference Example 1 A) of Japanese Patent Publication No. 63-235363.

[0306] (Synthesis Example 5) <Synthesis of Diphenyl Phosphate Cyclohexylamidate> Diphenyl phosphate cyclohexyl amide was synthesized according to Reference Example 1 of Japanese Patent Application Publication No. 2000-154277.

[0307] (Synthesis Example 6) <Synthesis of Diphenyl Phosphate Piperidylamidate> Diphenyl phosphate piperidylamidate was synthesized according to Example 2 of Japanese Patent Publication No. 49-72346.

[0308] (Synthesis Example 7) <Synthesis of Diphenyl Phosphate Morpholinoamide> Diphenyl phosphate morpholinoamide was synthesized according to Reference Example 3 of Japanese Patent Application Publication No. 2000-154277.

[0309] (Synthesis Example 8) <Synthesis of 2,6-dimethylphenylamide diphenyl phosphate> In a 1 L four-necked flask equipped with a stirrer, thermometer, and cooling condenser, 66.7 g (0.55 mol) of 2,6-dimethylaniline, 50.6 g (0.50 mol) of triethylamine, 3.1 g (0.03 mol) of 4-dimethylaminopyridine, and 400 g of toluene were placed. Under stirring, 134.3 g (0.5 mol) of diphenyl chlorophosphate was added over 1.0 hour. After the addition, the temperature was raised to 70°C and the mixture was stirred for 2 hours. After the reaction was complete, the mixture was cooled to 60°C and 200 g of 2% hydrochloric acid was added. The resulting powder crystals were treated in the same manner as in Synthesis Example 4 to obtain 161.6 g (yield 91.5%) of 2,6-dimethylphenylamide diphenyl phosphate. The obtained white powder product had a melting point of 140°C. The structure was determined by NMR. The NMR chart is shown in Figure 1.

[0310] (Synthesis Example 9) <Synthesis of aniline-based phosphoramide condensates> A 1 L four-necked flask equipped with a stirrer, thermometer, and hydrochloric acid recovery device (condenser connected to a water scrubber) contained 33 g (0.3 mol) of resorcinol, 183.6 g (0.87 mol) of phenyl dichlorophosphate, and 0.43 g (0.005 mol) of anhydrous magnesium chloride. The mixture was heated to 110°C over 1 hour while stirring. The mixture was stirred for 3 hours while recovering the generated hydrochloric acid using the hydrochloric acid recovery device. After the reaction was complete, the excess phenyl dichlorophosphate was recovered by heating to 135°C under reduced pressure (0.1 kPa). After recovery, the mixture was returned to room temperature and atmospheric pressure, and 300 g of toluene was added. Then, 111.8 g (1.2 mol) of aniline was added over 0.5 hours using an additional funnel. The flask was heated to 100°C and stirred for 4 hours. After cooling to 60°C, 300 g of 1% hydrochloric acid was added, and the toluene layer was separated using a separatory funnel. Subsequently, the toluene layer was neutralized with 200 g of water in which soda ash was dissolved, and then washed with 200 g of water twice. After removing the toluene, 163.6 g of glassy solid crystals was obtained. The product was a dimer (n １０９ = 1) was a mixture mainly composed of compound 1). GPC measurement was performed and n of the total amount of the obtained mixture (excluding solvent) １０９The amount of compound with a ratio of 1 was 75.1% by area. The structure of the obtained mixture was determined by NMR measurement. The NMR chart is shown in Figure 2.

[0311] (Synthesis Example 10) <Synthesis of Cyclohexylamine-based Phosphoamide Condensates> A 1 L four-necked flask equipped with a stirrer, thermometer, and hydrochloric acid recovery device (condenser connected to a water scrubber) contained 33 g (0.3 mol) of resorcinol, 183.6 g (0.87 mol) of phenyl dichlorophosphate, and 0.43 g (0.005 mol) of anhydrous magnesium chloride. The mixture was heated to 110°C over 1 hour while stirring. The mixture was stirred for 3 hours while recovering the generated hydrochloric acid using the hydrochloric acid recovery device. After the reaction was complete, the excess phenyl dichlorophosphate was recovered by heating to 135°C under reduced pressure (0.1 kPa). After recovery, the mixture was returned to room temperature and atmospheric pressure, 300 g of toluene was added, and 119 g (1.2 mol) of cyclohexylamine was added over 0.5 hours using an additional funnel. The flask was heated to 100°C and stirred for 4 hours. After cooling to 60°C, 300 g of 1% hydrochloric acid was added, and the toluene layer was separated using a separatory funnel. Subsequently, the toluene layer was neutralized with 200 g of water in which soda ash was dissolved, and then washed with 200 g of water twice. After removing the toluene, 170.4 g of glassy solid crystals was obtained. The product was a dimer (n １１０ = 1) was a mixture mainly composed of compound 1). GPC measurement was performed and n of the total amount of the obtained mixture (excluding solvent) １１０ The amount of compound with a ratio of 1 was 72.3 area %. The structure of the obtained mixture was determined by NMR measurement. The NMR chart is shown in Figure 3.

[0312] (Synthesis Example 11) <Synthesis of Morpholine-based Phosphoamide Condensates> A 1 L four-necked flask equipped with a stirrer, thermometer, and hydrochloric acid recovery device (condenser connected to a water scrubber) contained 33 g (0.3 mol) of resorcinol, 183.6 g (0.87 mol) of phenyl dichlorophosphate, and 0.43 g (0.005 mol) of anhydrous magnesium chloride. The mixture was heated to 110°C over 1 hour while stirring. The mixture was stirred for 3 hours while recovering the generated hydrochloric acid using the hydrochloric acid recovery device. After the reaction was complete, the excess phenyl dichlorophosphate was recovered by heating to 135°C under reduced pressure (0.1 kPa). After recovery, the mixture was returned to room temperature and atmospheric pressure, 300 g of toluene was added, and 104.5 g (1.2 mol) of morpholine was added over 0.5 hours using an additional funnel. The flask was heated to 100°C and stirred for 4 hours. After cooling to 60°C, 300 g of 1% hydrochloric acid was added, and the toluene layer was separated using a separatory funnel. Subsequently, the toluene layer was neutralized with 200 g of water in which soda ash was dissolved, and then washed with 200 g of water twice. After removing the toluene, 156.5 g of a highly viscous liquid compound was obtained. The obtained product was a dimer (n １１１ = 1) was a mixture mainly composed of compound 1). GPC measurement was performed and n of the total amount of the obtained mixture (excluding solvent) １１１ The amount of compound with a ratio of 1 was 69.0 area %. The structure of the obtained mixture was determined by NMR measurement. The NMR chart is shown in Figure 4.

[0313] (Synthesis Example 12) <Synthesis of aniline-based phosphoramidate condensates> A 1 L four-necked flask equipped with a stirrer, thermometer, and hydrochloric acid recovery device (condenser connected to a water scrubber) contained 33 g (0.3 mol) of hydroquinone, 183.6 g (0.87 mol) of phenyl dichlorophosphate, and 0.43 g (0.005 mol) of anhydrous magnesium chloride. The mixture was heated to 110°C over 1 hour while stirring. The mixture was stirred for 3 hours while recovering the generated hydrochloric acid using the hydrochloric acid recovery device. After the reaction was complete, the excess phenyl dichlorophosphate was recovered by heating to 135°C under reduced pressure (0.1 kPa). After recovery, the mixture was returned to room temperature and atmospheric pressure, 300 g of toluene was added, and 112 g (1.2 mol) of aniline was added over 0.5 hours using an additional funnel. The flask was heated to 100°C and stirred for 4 hours. After cooling to 60°C, 300 g of 1% hydrochloric acid was added, and the remaining powder in the flask was filtered under reduced pressure. The obtained filtrate was washed with 300 g of 1% hydrochloric acid, and then washed again with 200 g x 2 times water and 30 g of methanol. Afterward, it was dried under reduced pressure at 100°C for 6 hours to obtain 119.3 g of a white powder product. The product was a dimer (n １１２ = 1) was a mixture mainly composed of compound 1). GPC measurement was performed and n of the total amount of the obtained mixture (excluding solvent) １１２ The amount of compound with a ratio of 1 was 89.1% by area. The structure of the obtained mixture was determined by NMR measurement. The NMR chart is shown in Figure 5.

[0314] (Synthesis Example 13) <Synthesis of piperidine phosphoramidate condensates> A 1 L four-necked flask equipped with a stirrer, thermometer, and hydrochloric acid recovery device (condenser connected to a water scrubber) contained 33 g (0.3 mol) of hydroquinone, 183.6 g (0.87 mol) of phenyl dichlorophosphate, and 0.43 g (0.005 mol) of anhydrous magnesium chloride. The mixture was heated to 110°C over 1 hour while stirring. The mixture was stirred for 3 hours while recovering the generated hydrochloric acid using the hydrochloric acid recovery device. After the reaction was complete, the excess phenyl dichlorophosphate was recovered by heating to 135°C under reduced pressure (0.1 kPa). After recovery, the mixture was returned to room temperature and atmospheric pressure, 300 g of toluene was added, and 102.2 g (1.2 mol) of piperidine was added over 0.5 hours using an additional funnel. The flask was heated to 100°C and stirred for 4 hours. After cooling to 60°C, 300 g of 1% hydrochloric acid was added, and the toluene layer was separated using a separatory funnel. Subsequently, the toluene layer was neutralized with 200 g of water in which soda ash was dissolved, and then washed with 200 g of water twice. After removing the toluene, 155.9 g of a highly viscous liquid was obtained. The product was a dimer (n １１３ = 1) was a mixture mainly composed of compound 1). GPC measurement was performed and n of the total amount of the obtained mixture (excluding solvent) １１３ The amount of compound with a ratio of 1 was 74.1% by area. The structure of the obtained mixture was determined by NMR measurement. The NMR chart is shown in Figure 6.

[0315] (Synthesis Example 14) <Synthesis of Tetrahydroquinoline Phosphoramidate Condensates> A 1 L four-necked flask equipped with a stirrer, thermometer, and hydrochloric acid recovery device (condenser connected to a water scrubber) contained 33 g (0.3 mol) of resorcinol, 183.6 g (0.87 mol) of phenyl dichlorophosphate, and 0.43 g (0.005 mol) of anhydrous magnesium chloride. The mixture was heated to 110°C over 1 hour while stirring. The mixture was stirred for 3 hours while recovering the generated hydrochloric acid using the hydrochloric acid recovery device. After the reaction was complete, the excess phenyl dichlorophosphate was recovered by heating to 135°C under reduced pressure (0.1 kPa). After recovery, the mixture was returned to room temperature and atmospheric pressure, 300 g of toluene was added, and 157.2 g (1.18 mol) of 1,2,3,4-tetrahydroquinoline was added over 1.0 hour using an additional funnel. The flask was heated to 100°C and then stirred for 3 hours. After cooling to 60°C, 300 g of 1% hydrochloric acid was added and the toluene layer was separated using a separatory funnel. The toluene layer was then neutralized with 200 g of water containing dissolved soda ash, and further washed with 200 g of water twice. After removing the toluene, 98.2 g of a highly viscous liquid compound was obtained. The product was a dimer (n １１４ = 1) was a mixture mainly composed of compound 1). GPC measurement was performed and n of the total amount of the obtained mixture (excluding solvent) １１４ The amount of compound with a ratio of 1 was 77.1% by area. The structure of the obtained mixture was determined by NMR measurement. The NMR chart is shown in Figure 7.

[0316] (Synthesis Example 15) <Synthesis of methylaniline-based phosphoramidate condensates> A 1 L four-necked flask equipped with a stirrer, thermometer, and hydrochloric acid recovery device (condenser connected to a water scrubber) contained 33 g (0.3 mol) of hydroquinone, 183.6 g (0.87 mol) of phenyl dichlorophosphate, and 0.43 g (0.005 mol) of anhydrous magnesium chloride. The mixture was heated to 110°C over 1 hour while stirring. The mixture was stirred for 3 hours while recovering the generated hydrochloric acid using the hydrochloric acid recovery device. After the reaction was complete, the excess phenyl dichlorophosphate was recovered by heating to 135°C under reduced pressure (0.1 kPa). After recovery, the mixture was returned to room temperature and atmospheric pressure, 300 g of toluene was added, and 128.6 g (1.2 mol) of N-methylaniline was added over 0.5 hours using an additional funnel. The flask was heated to 100°C and stirred for 3 hours. After cooling to 60°C, 300 g of 1% hydrochloric acid was added, and the toluene layer was separated using a separatory funnel. Subsequently, the toluene layer was neutralized with 200 g of water in which soda ash was dissolved, and then washed with 200 g of water twice. After removing the toluene, 171.0 g of a highly viscous liquid was obtained. The product was a dimer (n １１５ = 1) was a mixture mainly composed of compound 1). GPC measurement was performed and n of the total amount of the obtained mixture (excluding solvent) １１５ The amount of compound with a ratio of 1 was 74.5% by area. The structure of the obtained mixture was determined by NMR measurement. The NMR chart is shown in Figure 8.

[0317] (Synthesis Example 16) <Synthesis of aniline-based phosphoramidate condensates> A 1 L four-necked flask equipped with a stirrer, thermometer, and hydrochloric acid recovery device (condenser connected to a water scrubber) contained 22 g (0.2 mol) of resorcinol, 138.6 g (0.58 mol) of 2,6-xylyl phosphorodichloride, and 0.29 g (0.003 mol) of anhydrous magnesium chloride. The mixture was heated to 125°C over 1 hour while stirring. The mixture was stirred for 3 hours while recovering the generated hydrochloric acid using the hydrochloric acid recovery device. After the reaction was complete, the excess 2,6-xylyl phosphorodichloride was recovered by heating to 165°C under reduced pressure (0.1 kPa). After recovery, the mixture was returned to room temperature and atmospheric pressure, 150 g of toluene was added, and 74.8 g (0.8 mol) of aniline was added over 0.5 hours using an additional funnel. The flask was heated to 100°C and stirred for 3 hours. After cooling to 60°C, the mixture was washed with 150g of water and separated into layers. The toluene layer was then washed with 100g of 2% hydrochloric acid and separated using a separatory funnel. Subsequently, the toluene layer was neutralized with 100g of water containing dissolved soda ash, and washed again with 100g of water once. The toluene layer was transferred to a beaker containing 400g of hexane, and the precipitated crystals were filtered while cooling to 10°C and lightly washed with acetone. After drying under reduced pressure, 60g of a white powder compound was obtained. The obtained product was n １１６ = 1 was the main component of the mixture. GPC measurement was performed and the total amount of the obtained mixture (excluding the solvent) was n １１６ The amount of compound with a ratio of 1 was 76.6 area %. The structure of the obtained mixture was determined by NMR measurement. The NMR chart is shown in Figure 9.

[0318] [Examples 1-16 and Comparative Examples 1-7] <Preparation of epoxy-curable resin cured products> The following materials were used as materials for the epoxy-curable resin composition: ・Bis-A type prepolymer (JER-828 Mitsubishi Chemical: formerly known as Epicote 828) ・Acid anhydride curing agent (Ricacid MH-700 Shin Nippon Rika) ・Amine catalyst (2,4,6-tris(dimethylaminomethyl)phenol Tokyo Chemical).

[0319] The mold was preheated to 100°C. Varnish was prepared by mixing various components in the proportions listed in Tables 1 to 4. The varnish was poured into the mold and heated under curing conditions of 100°C for 2 hours, then 120°C for 2 hours, and then 170°C for 5 hours. After heating was complete, the cured epoxy resin was removed from the mold.

[0320] <Preparation of Methacrylic-Modified PPE Resin Cured Products> The following raw materials were used to prepare the methacrylic-modified PPE resin cured products: • Methacrylic-modified PPE resin (SA-9000, manufactured by SABIC Corporation) • Triallyl isocyanurate (TAIC, manufactured by Tokyo Chemical Industry Co., Ltd.) • Perbutyl P (manufactured by NOF Corporation, organic peroxide).

[0321] Varnish was prepared by mixing the various components in the proportions listed in Table 5. A mixed solvent of THF / toluene = 4 / 1 was used as the solvent. 15 g of varnish was impregnated into 20 g of glass cloth (Unitika E10T), and then air-dried for 10 minutes. After that, it was dried in a hot air circulating oven at 90°C for 15 minutes to obtain a prepreg. Eight of the obtained prepregs were stacked and vacuum-pressed at a temperature of 170°C and a pressure of 3 MPa for 60 minutes to obtain a 0.6 mm thick laminated cured product.

[0322] <Test specimens for electrical property measurement> Cured epoxy resin material and cured modified PPE resin laminate were each cut into rod shapes measuring 80 mm (L) × 1.5 mm (W) × 0.6 mm (t) to obtain test specimens for measurement.

[0323] <Electrical Characteristics Measurement Equipment> The following electrical characteristics measurement equipment was used: • PNA Network Analyzer N5222B (manufactured by Keysight Technologies, Inc.) • Cavity resonator for 1GHz and 10GHz CP531 (manufactured by Kanto Electronics Applied Development Co., Ltd.)

[0324] The dielectric loss tangent was measured using the above-mentioned test specimen. Specifically, in accordance with IEC 62810, the dielectric constant and dielectric loss tangent (tanδ) were determined at frequencies of 1 GHz or 10 GHz using the cavity resonator perturbation method with the above-mentioned PNA network analyzer and cavity resonator.

[0325] The results are shown in Tables 1 to 5 below. In the following tables, the values ​​for the amount of each component are in parts by weight (Phr) based on 100 parts by weight of resin.

[0326] [Tables 1-4: Evaluation of electrical properties of epoxy resins (cast epoxy resins)] (Note) Epoxy resin*: JER-828 Curing agent: Ricacid MH-700 Catalyst: 2,4,6-tris(dimethylaminomethyl)phenol Synthesis Example 1: Compound of formula 101 Synthesis Example 2: Compound of formula 102 Synthesis Example 4: Compound of formula 104 Synthesis Example 5: Compound of formula 105 Synthesis Example 6: Compound of formula 106.

[0327] (Note) Synthesis example 7: Compound of formula 107. Synthesis example 8: Compound of formula 108. Synthesis example 9: Compound of formula 109. Synthesis example 10: Compound of formula 110. Synthesis example 11: Compound of formula 111.

[0328] (Note) Synthesis Example 12: Compound of Formula 112 Synthesis Example 13: Compound of Formula 113 Synthesis Example 14: Compound of Formula 114 Synthesis Example 15: Compound of Formula 115 Synthesis Example 16: Compound of Formula 116

[0329] (Note) Modifier 1: TPP (triphenyl phosphate) Modifier 2: SPB-100 (manufactured by Otsuka Chemical Co., Ltd., cyclic phosphazene-based flame retardant) Modifier 3: HCA (manufactured by Sanko Co., Ltd., 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide)

[0330] [Table 5: Electrical property evaluation of modified PPE resin (methacrylic modified curable resin)] (Note) Modified PPE resin: SA-9000 Crosslinking agent: TAIC Polymerization catalyst: Perbutyl P Synthesis example 1: Compound modifier 1 of formula 101: TPP Modifier 2: SPB-100.

[0331] (Discussion) From the results in Tables 1 to 5, it was confirmed that the modifier of the present invention reduces the dielectric loss tangent value and provides a thermosetting resin composition with excellent dielectric properties.

[0332] [Examples 17-19 and Comparative Example 8] <Measurement of Flame Retardancy> As shown in Examples 17-19 and Comparative Example 8 in the table below, the modifier was added to the samples for measuring flame retardancy so that the phosphorus atom content in the composition was 2.68%. Varnish was prepared by blending various components in the proportions shown in the table below. The varnish was poured into a mold and heated under curing conditions of 100°C for 2 hours, then 120°C for 2 hours, and then 170°C for 5 hours. After heating was complete, the epoxy resin cured product was removed from the mold.

[0333] The combustion behavior of the prepared test specimens was evaluated according to the UL-94 test method. The results are shown in Table 6 below. Samples in which the specimen completely burned were labeled "burn".

[0334] (Note) Epoxy resin: JER-828 Curing agent: Ricacid MH-700 Epoxy curing catalyst (2,4,6-tris(dimethylaminomethyl)phenol) Synthesis example 13: Compound of formula 113 Synthesis example 14: Compound of formula 114 Synthesis example 15: Compound of formula 115.

[0335] (Discussion) As shown in Table 6, in Comparative Example 8 the sample burned, whereas in Examples 17 to 19 flame retardancy of V-1 or V-0 was achieved. From the results in Table 6, it was confirmed that flame retardancy is also improved by the modifier of the present invention.

[0336] The present invention provides a modifier and a compound for a thermosetting resin composition for printed circuit boards having excellent dielectric properties. The present invention provides a modifier and a thermosetting resin composition particularly suitable for high-frequency printed circuit boards corresponding to next-generation communication standards. The modifier and thermosetting resin composition of the present invention provide a printed circuit board with a low dielectric loss tangent and high electrical signal transmission efficiency.

[0337] As described above, the present invention has been illustrated using preferred embodiments, but the present invention should not be construed as being limited to these embodiments. It is understood that the scope of the present invention should be interpreted solely by the claims. Those skilled in the art will understand that, based on the description of the specific preferred embodiments of the present invention and common technical knowledge, an equivalent scope can be practiced. It is understood that the patents, patent applications and documents cited herein should be incorporated as reference to this specification, just as their contents are specifically described herein.

Claims

1. A modifier for reducing transmission loss in a thermosetting resin composition for a circuit board, comprising a monomeric compound represented by the following general formula 1 or a polymeric compound represented by general formula 2, Here, in general formula 1, L １ is NR １ｂ and R １ａ and R １ｂ are the following structure 1a or structure 1b: (Structure 1a: R １ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １ｂ is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 1b: R １ａ and R １ｂ are each a linear alkyl group and R １ａ and R １ｂ are bonded together, and the nitrogen atom in L １ and R １ａ and R １ｂ together form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, where one CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl groups may each be independently linear or branched alkyl groups having 1 to 4 carbon atoms. Furthermore, the nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) and L ２ is O or NR ２ｂ And L ２ If O, then R ２ａ L is a phenyl group, which may be independently substituted with 1 to 3 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ２ NR ２ｂ If so, R ２ａ and R ２ｂ The following structure 2a or structure 2b: (Structure 2a: R ２ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ２ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 2b: R ２ａ and R ２ｂ Each of them is a linear alkyl group and R ２ａ and R ２ｂ They combine, L ２ The nitrogen atom and R inside ２ａ and R ２ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) and L ３ is O or NR ３ｂ And L ３ If O, then R ３ａ L is a phenyl group, which may be independently substituted with 1 to 3 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ３ NR ３ｂ If so, R ３ａ and R ３ｂ The following structure 3a or structure 3b: (Structure 3a: R ３ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ３ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 3b: R ３ａ and R ３ｂ Each of them is a linear alkyl group and R ３ａ and R ３ｂ They combine, L ３ The nitrogen atom and R inside ３ａ and R ３ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms.) And here, in general formula 2, the polymer compound has at least two PN bonds, where the PN bond is a covalent bond between one phosphorus atom and one nitrogen atom, R １０ L is a phenylene group, where the phenylene group may be independently substituted with 1 to 3 alkyl groups, and the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms. １１ is O or NR １１ｂ And L １１ If O, then R １１ａ L is a phenyl group, which may be independently substituted with 1 to 3 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. １１ NR １１ｂ If so, R １１ａ and R １１ｂ The following structure 4a or structure 4b: (Structure 4a: R １１ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １１ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 4b: R １１ａ and R １１ｂ Each of them is a linear alkyl group and R １１ａ and R １１ｂ They combine, L １１ The nitrogen atom and R inside １１ａ and R １１ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) and L １２ is O or NR １２ｂ And L １２ If O, then R １２ａ L is a phenyl group, which may be substituted with 1 to 3 alkyl groups, where the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. １２ NR １２ｂ If so, R １２ａ and R １２ｂ The following structure 5a or structure 5b: (Structure 5a: R １２ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １２ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 5b: R １２ａ and R １２ｂ Each of them is a linear alkyl group and R １２ａ and R １２ｂ They combine, L １２ the nitrogen atom therein and R １２ａ and R １２ｂ combine together to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, wherein one CH ２ in the nitrogen-containing aliphatic monocyclic group may be replaced by O to form a nitrogen-containing and oxygen-containing aliphatic monocyclic group, wherein a benzene ring may be further condensed with the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing and oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing and oxygen-containing condensed ring group, wherein the nitrogen-containing aliphatic monocyclic group and the nitrogen-containing and oxygen-containing aliphatic monocyclic group having 2 carbon atoms may each independently be substituted with one or two alkyl groups, wherein the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing aliphatic monocyclic group and the nitrogen-containing and oxygen-containing aliphatic monocyclic group having 3 to 9 carbon atoms may each independently be substituted with 1 to 3 alkyl groups, the alkyl group being independently a linear or branched alkyl group having 1 to 4 carbon atoms, wherein the nitrogen-containing condensed ring group and the nitrogen-containing and oxygen-containing condensed ring group may each independently be substituted with 1 to 6 alkyl groups, the alkyl group being independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) having, L １３ is O or NR １３ｂ where R １３ｂ is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, L １４ is O or NR １４ｂ where R １４ｂ is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, L １５ is O or NR １５ｂ where L １５ is O, R １５ａ is a phenyl group, which may be substituted with 1 to 3 alkyl groups, wherein the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, L １５ is NR １５ｂ where R １５ａ and R １５ｂ are the following structure 6a or structure 6b: (Structure 6a: R １５ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １５ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 6b: R １５ａ and R １５ｂ Each of them is a linear alkyl group and R １５ａ and R １５ｂ They combine, L １５ The nitrogen atom and R inside １５ａ and R １５ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) and L １６ is O or NR １６ｂ And L １６ If O, then R １６ａ L is a phenyl group, which may be independently substituted with 1 to 3 alkyl groups, where each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. １６ NR １６ｂ If so, R １６ａ and R １６ｂ The following structure 7a or structure 7b: (Structure 7a: R １６ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R １６ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 7b: R １６ａ and R １６ｂ Each of them is a linear alkyl group and R １６ａ and R １６ｂ They combine, L １６ The nitrogen atom and R inside １６ａ and R １６ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. １０ These are 1 to 6, and here, in general formula 2, L １１ and L １２ O and L １３ NR １３ is or L １１ and L １３ O and L １２ NR １２ is or L １２ and L １３ O and L １１ NR １１ And L １４ and L １５ O and L １６ NR １６ is or L １４ and L １６ O and L １５ NR １５ is or L １５ and L １６ O and L １４ NR １４ It is a modifier.

2. The modifier according to claim 1, wherein each of the rings present in the compound is either a six-membered ring or a fused ring formed by the fusion of a six-membered ring and a benzene ring.

3. The modifier according to claim 1, wherein each nitrogen atom in the compound is bonded to an unsubstituted phenyl group or an unsubstituted cyclohexyl group.

4. The modifier according to claim 1, wherein each nitrogen atom bonded to the phosphorus atom in the compound is one of the six ring atoms forming a six-membered ring, or one of the ring atoms of the six-membered ring portion of a fused ring formed by the condensation of a six-membered ring with a benzene ring.

5. The modifier according to claim 1, wherein the compound is the monomeric compound.

6. The modifier according to claim 1, wherein the compound is the polymer compound.

7. R １ａ , R ２ａ and R ３ａ The modifier according to claim 5, wherein is an unsubstituted phenyl.

8. L １３ and L １４ The modifier according to claim 6, wherein the same 9. L １３ and L １４ The modifier according to claim 6, wherein is O.

10. L １１ and L １６ The same, and L １２ and L １５ The modifier according to claim 9, wherein the same 11. R １１ａ , R １２ａ , R １５ａ and R １６ａ The modifier according to claim 6, wherein is an unsubstituted phenyl.

12. L １１ NR １１ｂ And L １２ ~L １５ is O, and L １６ NR １６ｂ The modifier according to claim 6.

13. R １０ The modifier according to claim 6, wherein is unsubstituted metaphenylene or unsubstituted paraphenylene.

14. The following general formula 2A: A compound represented by R ２０ R is a phenylene group, where the phenylene group may be independently substituted with 1 to 3 alkyl groups, and the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms. ２１ａ and R ２１ｂ The following structure 8a or structure 8b: (Structure 8a: R ２１ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ２１ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 8b: R ２１ａ and R ２１ｂ Each of them is a linear alkyl group and R ２１ａ and R ２１ｂ The nitrogen atom and R bond together. ２１ａ and R ２１ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ) and R ２２ａ R is a phenyl group, which may be substituted with 1 to 3 alkyl groups, and the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms. ２５ａ R is a phenyl group, which may be substituted with 1 to 3 alkyl groups, and the alkyl groups are independently linear or branched alkyl groups having 1 to 4 carbon atoms. ２６ａ and R ２６ｂ The following structure 9a or structure 9b: (Structure 9a: R ２６ａ is an aryl group having 6 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, where the aryl group or cycloalkyl group may be independently substituted with 1 to 3 alkyl groups, and the alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and R ２６ｂ (This is a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms.) (Structure 9b: R ２６ａ and R ２６ｂ Each of them is a linear alkyl group and R ２６ａ and R ２６ｂ The nitrogen atom and R bond together. ２６ａ and R ２６ｂ These combine to form a nitrogen-containing aliphatic monocyclic group having 2 to 9 carbon atoms, and here, one of the nitrogen-containing aliphatic monocyclic groups is CH ２ The carbon atoms may be replaced with oxygen to form a nitrogen-containing oxygen-containing aliphatic monocyclic group, and a benzene ring may be further condensed onto the nitrogen-containing aliphatic monocyclic group or the nitrogen-containing oxygen-containing aliphatic monocyclic group to form a nitrogen-containing condensed ring group or a nitrogen-containing oxygen-containing condensed ring group, and the nitrogen-containing aliphatic monocyclic group having 2 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with one or two alkyl groups, and the alkyl group may be independently a linear or branched alkyl group having 1 to 4 carbon atoms. The nitrogen-containing aliphatic monocyclic group having 3 to 9 carbon atoms and the nitrogen-containing oxygen-containing aliphatic monocyclic group may each be independently substituted with 1 to 3 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms, and the nitrogen-containing condensed ring group and the nitrogen-containing oxygen-containing condensed ring group may each be independently substituted with 1 to 6 alkyl groups, and each alkyl group is independently a linear or branched alkyl group having 1 to 4 carbon atoms. ２０ n is 1 to 6, where n ２０ If R is 1, ２０ is an unsubstituted phenylene group, and two oxygen atoms are bonded to the 1st and 3rd positions of the phenylene group, R ２１ａ is an unsubstituted phenyl group, R ２１ｂ is hydrogen and R ２２ａ and R ２５ａ is a 2,6-dimethylphenyl group and R ２６ａ If is an unsubstituted phenyl group, R ２６ｂ It is not hydrogen, and also n ２０ If R is 1, ２０ A phenylene group substituted with two tert-butyl groups, wherein two oxygen atoms are bonded to the 1st and 4th positions of the phenylene group, and the two tert-butyl groups are bonded to the 2nd and 5th positions of the phenylene group, ２１ａ is an unsubstituted phenyl group, R ２１ｂ is hydrogen and R ２２ａ and R ２５ａ is a 2,6-dimethylphenyl group and R ２６ａ If is an unsubstituted phenyl group, R ２６ｂ It is not hydrogen, and furthermore, n ２０ If R is 1 or 2, ２０ is an unsubstituted phenylene group, and two oxygen atoms are bonded to the 1st and 3rd positions of the phenylene group, R ２１ａ and R ２１ｂ It combines with the nitrogen atom to form a morpholino group, R ２６ａ and R ２６ｂ It combines with the nitrogen atom to form a morpholino group, and R ２２ａ If is an unsubstituted phenyl group, R ２５ａ This is a compound that does not contain an unsubstituted phenyl group.

15. R ２２ａ and R ２５ａ The compound according to claim 14, wherein the phenyl group is unsubstituted.

16. R ２０ The compound according to claim 14, wherein the group is an unsubstituted metaphenylene group or an unsubstituted paraphenylene group.

17. R ２１ａ and R ２６ａ However, it is an unsubstituted phenyl group or an unsubstituted cyclohexyl group, and R ２１ｂ and R ２６ｂ However, it is either a hydrogen or a methyl group, or R ２１ａ and R ２１ｂ It bonds with the nitrogen atom to form an unsubstituted piperidine group, an unsubstituted nitrogen-containing oxygen-containing aliphatic six-membered ring group, or an unsubstituted nitrogen-containing condensed ring group formed by the condensation of a nitrogen-containing aliphatic six-membered ring and a benzene ring, R ２６ａ and R ２６ｂ The compound according to claim 14, wherein the group is bonded to a nitrogen atom to form an unsubstituted piperidine group, an unsubstituted nitrogen-containing oxygen-containing aliphatic six-membered ring group, or an unsubstituted nitrogen-containing condensed ring group formed by the condensation of a nitrogen-containing aliphatic six-membered ring and a benzene ring.

18. In the above structure 8b, the nitrogen-containing aliphatic monocyclic group CH ２ It is not replaced by O, and in the above structure 9b, the nitrogen-containing aliphatic monocyclic group CH ２ The compound according to claim 14, wherein O is not replaced.

19. R ２０ However, it is an unsubstituted metaphenylene group or an unsubstituted paraphenylene group, R ２２ａ and R ２５ａ However, it is an unsubstituted phenyl group, R ２１ａ and R ２６ａ However, it is an unsubstituted phenyl group or an unsubstituted cyclohexyl group, and R ２１ｂ and R ２６ｂ However, it is either a hydrogen or a methyl group, or R ２１ａ and R ２１ｂ It bonds with the nitrogen atom to form an unsubstituted nitrogen-containing aliphatic six-membered ring, an unsubstituted nitrogen-containing oxygen-containing aliphatic six-membered ring, an unsubstituted nitrogen-containing condensed ring group, or an unsubstituted nitrogen-containing oxygen-containing condensed ring group, R ２６ａ and R ２６ｂ The compound according to claim 14, wherein the group is bonded to a nitrogen atom to form an unsubstituted nitrogen-containing aliphatic six-membered ring group, an unsubstituted nitrogen-containing oxygen-containing aliphatic six-membered ring group, or an unsubstituted nitrogen-containing condensed ring group formed by the condensation of a nitrogen-containing aliphatic six-membered ring and a benzene ring.

20. A thermosetting resin composition for a circuit board, comprising a modifier according to any one of claims 1 to 13 or a compound according to any one of claims 14 to 19 and a thermosetting resin.

21. The thermosetting resin composition according to claim 20, wherein the thermosetting resin comprises an epoxy resin or a polyphenylene ether resin modified with an ethylenically unsaturated group.

22. The thermosetting resin composition according to claim 20 for manufacturing an insulating layer in a high-frequency printed circuit board.

23. A high-frequency printed circuit board comprising a conductive layer and an insulating layer, wherein the insulating layer comprises the thermosetting resin composition described in claim 20.

24. A method for manufacturing a high-frequency printed circuit board comprising a conductive layer and an insulating layer, the method comprising the step of curing the thermosetting resin composition according to claim 20 to form the insulating layer.

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