JP7079127B2 - Color curable resin composition - Google Patents

Description

The present invention relates to a colored curable resin composition.

The color curable resin composition is used in the manufacture of a color filter used in a display device such as a liquid crystal display device, an electroluminescence display device, and a plasma display. The color-curable resin composition may contain two or more kinds of colorants having different colors in order to obtain a desired color tone or the like.

For example, Japanese Patent Application Laid-Open No. 2016-65115 (Patent Document 1) describes diketopyrrolopyrrole pigments and C.I. I. Pigment Yellow 139-containing coloring compositions, diketopyrrolopyrrole pigments and C.I. I. A coloring composition comprising Pigment Yellow 185 has been described.

Japanese Unexamined Patent Publication No. 2016-65115

It is an object of the present invention to provide a color curable resin composition having a higher contrast than the above-mentioned color curable resin composition known conventionally.

［式（Ｉ）中、
ａは、式（Ｉ）で表される化合物が有する－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-の合計数を表し、
ａ）ａが１～１０のいずれかの整数である場合、
ＸはＣＲ⁸Ｒ⁹を表し、
Ｒ¹は、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基又は水素原子を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。また該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
Ｒ²～Ｒ⁹は、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基、ニトロ基、－ＣＯ₂ ^-又は－Ｓ（Ｏ）₂Ｏ^-を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。また該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
Ｒ²とＲ³、Ｒ³とＲ⁴、Ｒ⁴とＲ⁵、Ｒ⁶とＲ⁷、及び、Ｒ⁸とＲ⁹の少なくとも１組は、各々が結合する炭素原子と一緒になって置換基を有していてもよい環を形成してもよく、該環が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。また、該環は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
Ｒ^naは、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基又は水素原子を表し、該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。Ｒ^naが複数個存在する場合、これらは同一でも異なっていてもよい。
Ｍ^b+は、ヒドロン又はｂ価の金属イオンを表す。Ｍ^b+が複数個存在する場合、これらは同一でも異なっていてもよい。Ｍ^b+がヒドロンのとき、該ヒドロンは前記－ＣＯ₂ ^-又は－Ｓ（Ｏ）₂Ｏ^-と一緒になって－ＣＯ₂Ｈ及びＳ（Ｏ）₂ＯＨとして存在する。
ｂは、１～６のいずれかの整数を表す。
ｍは、Ｍ^b+の個数を表す。
ｎは、ｎ＝ｂ×ｍ／ａの関係を満たす数である。
ｂ）ａが０である場合、
ｎは１を表し、かつｍは０を表す。
Ｒ¹は、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基又は水素原子を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
Ｒ²～Ｒ⁵は、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
Ｒ²とＲ³、Ｒ³とＲ⁴、及び、Ｒ⁴とＲ⁵の少なくとも一組は、各々が結合する炭素原子と一緒になって置換基を有していてもよい環を形成してもよく、該環が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
Ｒ⁶は、－ＣＯ－ＯＲ^nb1、－ＣＯ－ＮＨ₂、－ＣＯ－ＮＨ（Ｒ^nb1）、－ＣＯ－Ｎ（Ｒ^nb1）₂、－ＣＯ－Ｈ、－ＣＯ－Ｒ^nb1又は－Ｓ（Ｏ）₂－Ｒ^nb1を表す。
ただし、Ｒ⁶が－ＣＯ－ＮＨ（Ｒ^nb1）を表す場合、Ｒ²～Ｒ⁵は、（ｉｂ）及び（ｉｉｂ）の少なくとも一方を充足する。
（ｉｂ）Ｒ²～Ｒ⁵の少なくとも一つが、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
（ｉｉｂ）Ｒ²とＲ³、Ｒ³とＲ⁴、及び、Ｒ⁴とＲ⁵からなる群から選ばれる少なくとも一組は、各々が結合する炭素原子と一緒になって結合して置換基を有していてもよい環を形成しており、該環が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。Ｒ²～Ｒ⁵のうち環を形成しないものは、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
Ｒ⁷は、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。またＲ⁷は、Ｒ⁶及びＲ⁷が結合する炭素原子と一緒になって環を形成していてもよい。
Ｘは、式（１ａ）で表される基を表す。

［式（１ａ）中、Ｒ^17b～Ｒ^18bは、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
Ｒ^17bとＲ^18bは、各々が結合する炭素原子と一緒になって置換基を有していてもよい環を形成してもよく、該環が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
＊１は、イソインドリン環との結合手を表す。］
Ｒ^nbは、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基又は水素原子を表す。Ｒ^nbが複数個存在する場合、これらは同一でも異なっていてもよい。
Ｒ^nb1は、置換基を有していてもよい炭素数１～３５の炭化水素基又は置換基を有していてもよい複素環基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb10－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。Ｒ^nb1が複数個存在する場合、これらは同一でも異なっていてもよい。
Ｒ^nb10は、置換基を有していてもよい炭素数１～３５の炭化水素基、置換基を有していてもよい複素環基又は水素原子を表す。Ｒ^nb10が複数個存在する場合、これらは同一でも異なっていてもよい。］
［２］式（１ａ）で表される基が、式（２ａ）で表される基である［１］に記載の着色硬化性樹脂組成物。

［式（２ａ）中、Ｒ^19b～Ｒ^20bは、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基又は水素原子を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
Ｒ^nbは、前記と同じ意味を表す。
＊２は、イソインドリン環との結合手を表す。］
［３］式（Ｉ）で表される化合物が、式（ＩＩ）で表される化合物である［１］に記載の着色硬化性樹脂組成物。

［式（ＩＩ）中、
Ｒ¹¹は、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基又は水素原子を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。また該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
Ｒ¹²～Ｒ¹⁵は、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
Ｒ¹²とＲ¹³、Ｒ¹³とＲ¹⁴、及び、Ｒ¹⁴とＲ¹⁵は、各々が結合する炭素原子と一緒になって置換基を有していてもよい環を形成してもよく、該環が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－、－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。該環は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
Ｒ¹⁶は、－ＣＯ－ＯＲ^na1、－ＣＯ－ＮＨ₂、－ＣＯ－ＮＨ（Ｒ^na1）、－ＣＯ－Ｎ（Ｒ^na1）₂、－ＣＯ－Ｈ、－ＣＯ－Ｒ^na1又は－Ｓ（Ｏ）₂－Ｒ^na1を表す。
ただし、Ｒ¹⁶が－ＣＯ－ＮＨ（Ｒ^na1）を表す場合、Ｒ¹²～Ｒ¹⁵は、（ｉｘ）及び（ｉｉｘ）の少なくとも一方を充足する。
（ｉｘ）Ｒ¹²～Ｒ¹⁵の少なくとも一つが、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。また該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
（ｉｉｘ）Ｒ¹²とＲ¹³、Ｒ¹³とＲ¹⁴、及び、Ｒ¹⁴とＲ¹⁵の少なくとも一組は、各々が結合する炭素原子と一緒になって結合して置換基を有していてもよい環を形成しており、該環が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。また該環は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。Ｒ¹²～Ｒ¹⁵のうち環を形成しないものは、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ及び－Ｓ（Ｏ）₂ＯＨを形成することはない。また該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
Ｘ¹は、式（１ａ－ｘ）で表される基を表す。

［式（１ａ－ｘ）中、Ｒ²¹～Ｒ²²は、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
Ｒ²¹とＲ²²とは、互いに結合して置換基を有していてもよい環を形成してもよく、該環が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。該環は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
＊１は、イソインドリン環との結合手を表す。］
Ｒ^naは、前記と同じ意味を表す。
Ｒ^na1は、置換基を有していてもよい炭素数１～３５の炭化水素基又は置換基を有していてもよい複素環基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na10－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ及び－Ｓ（Ｏ）₂ＯＨを形成することはない。また該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。Ｒ^na1が複数個存在する場合、これらは同一でも異なっていてもよい。
Ｒ^na10は、置換基を有していてもよい炭素数１～３５の炭化水素基又は置換基を有していてもよい複素環基を表し、Ｒ^na10が複数個存在する場合、これらは同一でも異なっていてもよい。
ａｘは、式（ＩＩ）で表される化合物が有する－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-の合計数であり、０～１０のいずれかの整数を表す。
ＭＸ^bx+は、ヒドロン又はｂｘ価の金属イオンを表す。ＭＸ^bx+が複数個存在する場合、これらは同一でも異なっていてもよい。ＭＸ^bx+がヒドロンのとき、該ヒドロンは前記－ＣＯ₂ ^-又は－Ｓ（Ｏ）₂Ｏ^-と一緒になって－ＣＯ₂Ｈ及びＳ（Ｏ）₂ＯＨとして存在する。
ｂｘは、１～６のいずれかの整数を表す。
ａｘが０のときｍｘは０であり；ａｘが０以外のとき、ｍｘは、ＭＸ^b+の個数を表す。
ａｘが０のときｎｘは０であり；ａｘが０以外のとき、ｎｘは、ｎｘ＝ｂｘ×ｍｘ／ａｘの関係を満たす数である。］
［４］式（１ａ－ｘ）で表される基が、式（２ａ－ｘ）で表される基である［３］に記載の着色硬化性樹脂組成物。

［式（２ａ－ｘ）中、Ｒ²³～Ｒ²⁴は、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基又は水素原子を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ及び－Ｓ（Ｏ）₂ＯＨを形成することはない。また該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
Ｒ^naは、前記と同じ意味を表す。
＊２は、イソインドリン環との結合手を表す。］
［５］さらに溶剤を含む［１］～［４］のいずれかに記載の着色硬化性樹脂組成物。
［６］［１］～［５］のいずれかに記載の着色硬化性樹脂組成物から形成されるカラーフィルタ。
［７］［６］記載のカラーフィルタを含む表示装置。 The present invention includes the following inventions.
[1] Containing a colorant, a resin, a polymerizable compound and a polymerization initiator,
A coloring curable resin composition containing a compound represented by the following formula (I) and a red pigment as a coloring agent.

[In formula (I),
a represents the total number of −CO _2- ^{and —S} (O) ₂ O— possessed by the compound represented by the formula (I).
a) When a is an integer of 1 to 10,
X represents CR ⁸ R ⁹
R ¹ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and is contained in the hydrocarbon group-CH. When _2- and the heterocyclic group contain -CH _2- , which does not form a ring, the -CH _2- is replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . May be. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ² to R ⁹ are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, and a cyano. Represents a group, a nitro group, -CO ₂ ^- or-S (O) ₂ O-, and contains -CH ₂ -contained in the hydrocarbon group and -CH ₂ ^- in which the heterocyclic group does not form a ring. The -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
At least one set of R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , and R ⁸ and R ⁹ is a substituent together with the carbon atom to which each is bonded. May form a ring, and when the ring contains -CH _2- , which does not form a ring, the -CH _2- is -O-, -CO-, -S (O). It may be replaced with ₂ -or-NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the ring may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ^na represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and the hydrocarbon group and the heterocyclic group. May have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . When there are a plurality of R ^na , they may be the same or different.
M ^{b +} represents a hydron or b-valent metal ion. When there are a plurality of M ^{b +} , they may be the same or different. When M ^{b +} is a hydron, the hydron exists as -CO ₂ H and S (O) ₂ OH together with the -CO ₂ ^- or ^- S (O) ₂ O-.
b represents an integer of 1 to 6.
m represents the number of M ^{b +} .
n is a number that satisfies the relationship of n = b × m / a.
b) If a is 0,
n represents 1 and m represents 0.
R ¹ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and is contained in the hydrocarbon group-CH. When _2- and the heterocyclic group contain -CH _2- , which does not form a ring, the -CH _2- is replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . May be. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ² to R ⁵ are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, and a cyano. Representing a group or nitro group, -CH _2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
At least one pair of R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ together with the carbon atom to which each bond forms a ring that may have a substituent. Also, when the ring contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . good. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ⁶ is -CO-OR ^nb1 , -CO-NH ₂ , -CO-NH (R ^nb1 ), -CO-N (R ^nb1 ) ₂ , -CO-H, -CO-R ^nb1 or -S (O). ) ₂ -R represents ^nb1 .
However, when R ⁶ represents −CO-NH (R ^nb1 ), R ² to R ⁵ satisfy at least one of (ib) and (iib).
(Ib) At least one of R ² to R ⁵ is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a halogen atom, and a cyano group. Or, when it represents a nitro group and contains —CH ₂ − contained in the hydrocarbon group and —CH _{2 − in which the heterocyclic group does not form a ring, the —CH 2 −} is —O—, —CO—, It may be replaced with -S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
(Iib) At least one set selected from the group consisting of R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ is bonded together with the carbon atom to which each bond to form a substituent. When the ring forms a ring that may be possessed and the ring contains -CH _2- , which does not form a ring, the -CH _2- is -O-, -CO-, -S (O) _2- . Alternatively, it may be replaced with −NR ^nb −. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Of R ² to R ⁵ , those which do not form a ring are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and a heterocyclic group which may have a substituent. Representing a hydrogen atom, a halogen atom, a cyano group or a nitro group, -CH _{2- contained in the hydrocarbon group and -CH 2- when} the heterocyclic group does not form a ring-CH _2- It may be replaced with -O-, -CO-, -S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ⁷ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, a cyano group or a nitro group. When -CH _2- and the heterocyclic group do not form a ring-CH _2- contained in the hydrocarbon group, the -CH _2- is -O-, -CO-, -S (O) ₂ . -Or-may be replaced with -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, R ⁷ may form a ring together with the carbon atom to which R ⁶ and R ⁷ are bonded.
X represents a group represented by the formula (1a).

[In the formula (1a), R ^17b to R ^18b are each independently of a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and a heterocyclic group which may have a substituent. Representing a hydrogen atom, a halogen atom, a cyano group or a nitro group, -CH _{2- contained in the hydrocarbon group and -CH 2- when} the heterocyclic group does not form a ring-CH _2- It may be replaced with -O-, -CO-, -S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^17b and R ^18b may form a ring, each of which may have a substituent, together with the carbon atom to which it is bonded, when the ring contains non-ring-CH _2- . The -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
* 1 represents a bond with an isoindoline ring. ]
R ^nb represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, or a hydrogen atom. When there are a plurality of R ^nbs , they may be the same or different.
R ^nb1 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and is contained in the hydrocarbon group -CH _2- and. When the heterocyclic group contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb10- . .. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. When there are a plurality of R ^nb1 , they may be the same or different.
R ^nb10 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, or a hydrogen atom. When there are a plurality of R ^nb10s , they may be the same or different. ]
[2] The colored curable resin composition according to [1], wherein the group represented by the formula (1a) is the group represented by the formula (2a).

[In the formula (2a), R ^19b to R ^20b are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, or a substituent. Representing a hydrogen atom and containing —CH ₂ − contained in the hydrocarbon group and —CH _{2 − in which the heterocyclic group does not form a ring, the —CH 2 −} is —O—, −CO−, −. It may be replaced with S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^nb has the same meaning as described above.
* 2 represents a bond with the isoindoline ring. ]
[3] The colored curable resin composition according to [1], wherein the compound represented by the formula (I) is a compound represented by the formula (II).

[In formula (II),
R ¹¹ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and is contained in the hydrocarbon group-CH. When _2- and the heterocyclic group contain -CH _2- , which does not form a ring, the -CH _2- is replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . May be. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ¹² to R ¹⁵ are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, and a cyano. Representing a group or a nitro group, -CH 2- when the hydrocarbon group contains -CH _2- and the heterocyclic group does not form a ring-CH _2- , the -CH _2- is -O-, -CO-. , -S (O) _2- or -NR ^na- may be replaced. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. The hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ¹² and R ¹³ , R ¹³ and R ¹⁴ , and R ¹⁴ and R ¹⁵ may each be combined with the carbon atom to which they are bonded to form a ring that may have a substituent. When the ring contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- , -NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. The ring may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ¹⁶ is -CO-OR ^na1 , -CO-NH ₂ , -CO-NH (R ^na1 ), -CO-N (R ^na1 ) ₂ , -CO-H, -CO-R ^na1 or -S (O). ) ₂ -R represents ^na1 .
However, when R ¹⁶ represents −CO-NH (R ^na1 ), R ¹² to R ¹⁵ satisfy at least one of (ix) and (iix).
(Ix) At least one of R ¹² to R ¹⁵ is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a halogen atom, and a cyano group. Or, when it represents a nitro group and contains —CH ₂ − contained in the hydrocarbon group and —CH _{2 − in which the heterocyclic group does not form a ring, the —CH 2 −} is —O—, —CO—, It may be replaced with -S (O) ₂ -or-NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
(Iix) Even if at least one set of R ¹² and R ¹³ , R ¹³ and R ¹⁴ , and R ¹⁴ and R ¹⁵ are bonded together with the carbon atom to which they are bonded and have a substituent. When a good ring is formed and the ring contains -CH _2- , which does not form a ring, the -CH _2- is -O-, -CO-, -S (O) _2- or -NR ^na- . May be replaced with. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the ring may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . Of R ¹² to R ¹⁵ , those which do not form a ring are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and a heterocyclic group which may have a substituent. Representing a hydrogen atom, a halogen atom, a cyano group or a nitro group, -CH _{2- contained in the hydrocarbon group and -CH 2- when} the heterocyclic group does not form a ring-CH _2- It may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
X ¹ represents a group represented by the formula (1a-x).

[In the formula (1a-x), R ²¹ to R ²² are independent of each other and may have a hydrocarbon group having 1 to 40 carbon atoms and a heterocycle which may have a substituent. Representing a group, a hydrogen atom, a halogen atom, a cyano group or a nitro group, and containing -CH _2- contained in the hydrocarbon group and -CH _2- when the heterocyclic group does not form a _ring- . May be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. The hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ²¹ and R ²² may be bonded to each other to form a ring which may have a substituent, and when the ring contains -CH _2- , which does not form a ring, the -CH _2- , -O-, -CO-, -S (O) ₂ -or -NR ^na- may be replaced. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. The ring may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
* 1 represents a bond with an isoindoline ring. ]
R ^na has the same meaning as described above.
R ^na1 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and is contained in the hydrocarbon group -CH _2- and. When the heterocyclic group contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na10- . .. However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . When there are a plurality of R ^na1 , they may be the same or different.
R ^na10 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and when a plurality of R ^na10 are present, they are the same. But it can be different.
ax is the total number of —CO ₂ ⁻ and —S (O) ₂ O ⁻ possessed by the compound represented by the formula (II), and represents an integer of 0 to 10.
MX ^{bx +} represents a hydron or bx-valent metal ion. If there are multiple MX ^{bx +} , they may be the same or different. When MX ^{bx +} is a hydron, the hydron exists as -CO ₂ H and S (O) ₂ OH together with the -CO _2- ^{or -S} (O) ₂ O-.
bx represents an integer of 1 to 6.
When ax is 0, mx is 0; when ax is other than 0, mx represents the number of MX ^{b +} .
When ax is 0, nx is 0; when ax is other than 0, nx is a number that satisfies the relationship nx = bx × mx / ax. ]
[4] The colored curable resin composition according to [3], wherein the group represented by the formula (1ax) is the group represented by the formula (2ax).

[In the formula (2a-x), R ²³ to R ²⁴ are independent of each other and may have a hydrocarbon group having 1 to 40 carbon atoms and a heterocycle which may have a substituent. When a group or a hydrogen atom is contained and the hydrocarbon group contains -CH _2- and the heterocyclic group does not form a ring-CH _2- , the -CH _2- is -O-, -CO-. , -S (O) _2- or -NR ^na- may be replaced. However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ^na has the same meaning as described above.
* 2 represents a bond with the isoindoline ring. ]
[5] The colored curable resin composition according to any one of [1] to [4], which further contains a solvent.
[6] A color filter formed from the colored curable resin composition according to any one of [1] to [5].
[7] A display device including the color filter according to [6].

According to the color curable resin composition of the present invention, a color filter having high contrast can be formed.

The color-curable resin composition of the present invention contains a colorant, a resin, a polymerizable compound and a polymerization initiator.
The colored curable resin composition of the present invention preferably further contains a solvent.
The colored curable resin composition of the present invention may contain a leveling agent.
In the present specification, the compounds exemplified as each component may be used alone or in combination of a plurality of kinds unless otherwise specified.

<Colorant (A)>
The colorant contains a compound represented by the formula (I) and a red pigment.

［式（１ａ）中、Ｒ^17b～Ｒ^18bは、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
Ｒ^17bとＲ^18bは、各々が結合する炭素原子と一緒になって置換基を有していてもよい環を形成してもよく、該環が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
＊１は、イソインドリン環との結合手を表す。］
Ｒ^nbは、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基又は水素原子を表す。Ｒ^nbが複数個存在する場合、これらは同一でも異なっていてもよい。
Ｒ^nb1は、置換基を有していてもよい炭素数１～３５の炭化水素基又は置換基を有していてもよい複素環基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb10－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。Ｒ^nb1が複数個存在する場合、これらは同一でも異なっていてもよい。
Ｒ^nb10は、置換基を有していてもよい炭素数１～３５の炭化水素基、置換基を有していてもよい複素環基又は水素原子を表す。Ｒ^nb10が複数個存在する場合、これらは同一でも異なっていてもよい。］ [In formula (I),
a represents the total number of −CO _2- ^{and —S} (O) ₂ O— possessed by the compound represented by the formula (I).
a) When a is an integer of 1 to 10,
X represents CR ⁸ R ⁹
R ¹ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and is contained in the hydrocarbon group-CH. When _2- and the heterocyclic group contain -CH _2- , which does not form a ring, the -CH _2- is replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . May be. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ² to R ⁹ are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, and a cyano. When it represents a group, a nitro group, -CO ₂ ^- or -S ₍ O) ₂ O-, and contains -CH _2- contained in the hydrocarbon group and -CH ^2- in which the heterocyclic group does not form a ring. The -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
At least one set of R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , and R ⁸ and R ⁹ is a substituent together with the carbon atom to which each is bonded. May form a ring, and when the ring contains -CH _2- , which does not form a ring, the -CH _2- is -O-, -CO-, -S (O). It may be replaced with ₂ -or-NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the ring may have at least one selected from the group consisting of —CO ₂ ⁻ and —S (O) ₂ O ⁻ .
R ^na represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and the hydrocarbon group and the heterocyclic group. May have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . When there are a plurality of R ^na , they may be the same or different.
M ^{b +} represents a hydron or b-valent metal ion. When there are a plurality of M ^{b +} , they may be the same or different. When M ^{b +} is a hydron, the hydron exists as -CO ₂ H and S (O) ₂ OH together with the -CO ₂ ^- or ^- S (O) ₂ O-.
b represents an integer of 1 to 6.
m represents the number of M ^{b +} .
n is a number that satisfies the relationship of n = b × m / a.
b) If a is 0,
n represents 1 and m represents 0.
R ¹ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and is contained in the hydrocarbon group-CH. When _2- and the heterocyclic group contain -CH _2- , which does not form a ring, the -CH _2- is replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . May be. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ² to R ⁵ are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, and a cyano. Representing a group or nitro group, -CH _2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
At least one pair of R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ together with the carbon atom to which each bond forms a ring that may have a substituent. Also, when the ring contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . good. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ⁶ is -CO-OR ^nb1 , -CO-NH ₂ , -CO-NH (R ^nb1 ), -CO-N (R ^nb1 ) ₂ , -CO-H, -CO-R ^nb1 or -S (O). ) ₂ -R represents ^nb1 .
However, when R ⁶ represents −CO-NH (R ^nb1 ), R ² to R ⁵ satisfy at least one of (ib) and (iib).
(Ib) At least one of R ² to R ⁵ is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a halogen atom, and a cyano group. Or, when it represents a nitro group and contains —CH ₂ − contained in the hydrocarbon group and —CH _{2 − in which the heterocyclic group does not form a ring, the —CH 2 −} is —O—, —CO—, It may be replaced with -S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
(Iib) At least one set selected from the group consisting of R ² and R ³ , R ³ and R ⁴ , and R ⁴ and R ⁵ is bonded together with the carbon atom to which each bond to form a substituent. When a ring is formed which may be possessed and the ring contains -CH _2- , which does not form a ring, the -CH _2- is -O-, -CO-, -S (O) _2- . Alternatively, it may be replaced with −NR ^nb −. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Of R ² to R ⁵ , those which do not form a ring are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and a heterocyclic group which may have a substituent. Representing a hydrogen atom, a halogen atom, a cyano group or a nitro group, -CH _{2- contained in the hydrocarbon group and -CH 2- when} the heterocyclic group does not form a ring-CH _2- It may be replaced with -O-, -CO-, -S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ⁷ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, a cyano group or a nitro group. When -CH _2- and the heterocyclic group do not form a ring-CH _2- contained in the hydrocarbon group, the -CH _2- is -O-, -CO-, -S (O) ₂ . -Or-may be replaced with -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, R ⁷ may form a ring together with the carbon atom to which R ⁶ and R ⁷ are bonded.
X represents a group represented by the formula (1a).

[In the formula (1a), R ^17b to R ^18b are each independently of a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and a heterocyclic group which may have a substituent. Representing a hydrogen atom, a halogen atom, a cyano group or a nitro group, -CH _{2- contained in the hydrocarbon group and -CH 2- when} the heterocyclic group does not form a ring-CH _2- It may be replaced with -O-, -CO-, -S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^17b and R ^18b may form a ring, each of which may have a substituent, together with the carbon atom to which it is bonded, when the ring contains non-ring-CH _2- . The -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
* 1 represents a bond with the isoindrin ring. ]
R ^nb represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, or a hydrogen atom. When there are a plurality of R ^nbs , they may be the same or different.
R ^nb1 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and is contained in the hydrocarbon group -CH _2- and. When the heterocyclic group contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb10- . .. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. When there are a plurality of R ^nb1 , they may be the same or different.
R ^nb10 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, or a hydrogen atom. When there are a plurality of R ^nb10s , they may be the same or different. ]

The compound represented by the formula (I) has a (that is, the total number of -CO _2- ^{and -S} (O) ₂ O- possessed by the compound represented by the formula (I)) of any one of 1 to 10. It includes a compound represented by the formula (IA) according to the first aspect, which is an integer, and a compound represented by the formula (IB) according to the second aspect, wherein a is 0.

Aspect 1: A compound represented by the formula (IA).

[In formula (IA),
R ^1a represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and is contained in the hydrocarbon group-CH. When _2- and the heterocyclic group contain -CH _2- , which does not form a ring, the -CH _2- is replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . May be. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ^2a to R ^9a are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, and a cyano. When it represents a group, a nitro group, -CO ₂ ^- or -S ₍ O) ₂ O-, and contains -CH _2- contained in the hydrocarbon group and -CH ^2- in which the heterocyclic group does not form a ring. The -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . At least one set of R ^2a and R ^3a , R ^3a and R ^4a , R ^4a and R ^5a , R ^6a and R ^7a , and R ^8a and R ^9a are substituents together with the carbon atom to which they are bonded. May form a ring, and when the ring contains -CH _2- , which does not form a ring, the -CH _2- is -O-, -CO-, -S (O). It may be replaced with ₂ -or -NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the ring may have at least one selected from the group consisting of —CO ₂ ⁻ and —S (O) ₂ O ⁻ .
R ^na represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and the hydrocarbon group and the heterocyclic group. May have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . When there are a plurality of R ^na , they may be the same or different.
M ^{b +} represents a hydron or b-valent metal ion. When there are a plurality of M ^{b +} , they may be the same or different.
b represents an integer of 1 to 6.
aa represents an integer of 1 to 10.
ma represents the number of M ^{b +} .
na is a number that satisfies the relationship of na = b × ma / aa. ]

Aspect 2: A compound represented by the formula (IB).

[In formula (IB),
R ^1b represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and is contained in the hydrocarbon group-CH. When _2- and the heterocyclic group contain -CH _2- , which does not form a ring, the -CH _2- is replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . May be. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^2b to R ^5b are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, and a cyano. Representing a group or nitro group, -CH _2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. At least one pair of R ^2b and R ^3b , R ^3b and R ^4b , and R ^4b and R ^5b , together with the carbon atoms to which they bind, form a ring that may have a substituent. Also, when the ring contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . good. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^6b is -CO-OR ^nb1 , -CO-NH ₂ , -CO-NH (R ^nb1 ), -CO-N (R ^nb1 ) ₂ , -CO-R ^nb1 or -S (O) ₂ -R ^nb1. Represents.
However, when R ^6b represents -CO-NH (R ^nb1 ), R ^2b to R ^5b satisfy at least one of (ib) and (iib).
(Ib) At least one of R ^2b to R ^5b may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group which may have a substituent, a halogen atom, a cyano group, or the like. Representing a nitro group, when the hydrocarbon group contains -CH _2- and the heterocyclic group does not form a ring-CH _2- , the -CH _2- is -O-, -CO-,-. It may be replaced with S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
(Iib) At least one set selected from the group consisting of R ^2b and R ^3b , R ^3b and R ^4b , and R ^4b and R ^5b is bonded together with the carbon atom to which each is bonded to form a substituent. When a ring is formed which may be possessed and the ring contains -CH _2- , which does not form a ring, the -CH _2- is -O-, -CO-, -S (O) _2- . Alternatively, it may be replaced with −NR ^nb −. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Of R ^2b to R ^5b , those which do not form a ring are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and a heterocyclic group which may have a substituent. Representing a hydrogen atom, a halogen atom, a cyano group or a nitro group, -CH _{2- contained in the hydrocarbon group and -CH 2- when} the heterocyclic group does not form a ring-CH _2- It may be replaced with -O-, -CO-, -S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^7b represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, a cyano group or a nitro group. When the hydrocarbon group contains -CH _2- and the heterocyclic group does not form a ring-CH _2- , the -CH _2- is -O-, -CO-, -S (O) ₂ . -Or-may be replaced with -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, R ^7b may form a ring together with the carbon atom to which R ^6b and R ^7b are bonded.
X ^b represents a group represented by the formula (1a).

[In the formula (1a), R ^17b to R ^18b may have a substituent other than the hydrocarbon group having 1 to 40 carbon atoms, which may have a substituent independently of each other. Representing a group, a hydrogen atom, a halogen atom, a cyano group or a nitro group, the —CH ₂ − when the hydrocarbon group contains —CH ₂ − and the heterocyclic group does not form a ring −CH ₂ −. May be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^17b and R ^18b may form a ring, each of which may have a substituent, together with the carbon atom to which it is bonded, when the ring contains non-ring-CH _2- . The -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
* 1 represents a bond with an isoindoline ring. ]
R ^nb represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, or a hydrogen atom. When there are a plurality of R ^nbs , they may be the same or different.
R ^nb1 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and is contained in the hydrocarbon group -CH _2- and. When the heterocyclic group contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb10- . .. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. When there are a plurality of R ^nb1 , they may be the same or different.
R ^nb10 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, or a hydrogen atom. When there are a plurality of R ^nb10s , they may be the same or different. ]

The total number of —CO ₂ H and —S (O) ₂ OH contained in the compound represented by the formula (IB) is 0. Hereinafter, -CO _2- ^and -S (O) ₂ O- may be referred ^to as "hydron-binding group".

In the second aspect, the group represented by the formula (1a) includes the group represented by the formula (2a).

[In the formula (2a), R ^19b to R ^20b are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, or a substituent. Representing a hydrogen atom and containing —CH ₂ − contained in the hydrocarbon group and —CH _{2 − in which the heterocyclic group does not form a ring, the —CH 2 −} is —O—, −CO−, −. It may be replaced with S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^nb has the same meaning as described above.
* 2 represents a bond with the isoindoline ring. ]

The number of carbon atoms of the group formed by replacing -CH _2- in the hydrocarbon group with -O-, -CO-, -S (O) _2- , -NR ^na- , -NR ^nb- , etc. is It is counted as the number of carbon atoms before being replaced with -O-, -CO-, -S (O) _2- , -NR ^na- , -NR ^nb- , etc.
As used herein, "substituent" does not include -COOH and -S (O) ₂ OH. Further, the "substituent group" does not include a group formed by replacing -CH _2- with -O-, -CO-, -S (O) _2- , -NR ^na- or -NR ^nb- . The group formed by replacing -CH _2- with -O-, -CO- or -S (O) _2- , -NR ^na- may be hereinafter referred to as "group (Z1)". The group formed by replacing -CH _2- with -O-, -CO-, -S (O) _2- or -NR ^nb- may be hereinafter referred to as "group (Z2)".

The compound represented by the formula (I) is preferably a compound represented by the formula (II).

［式（１ａ－ｘ）中、Ｒ²¹～Ｒ²²は、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
Ｒ²¹とＲ²²とは、互いに結合して置換基を有していてもよい環を形成してもよく、該環が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。該環は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。
＊１は、イソインドリン環との結合手を表す。］
Ｒ^naは、前記と同じ意味を表す。
Ｒ^na1は、置換基を有していてもよい炭素数１～３５の炭化水素基又は置換基を有していてもよい複素環基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^na10－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ及び－Ｓ（Ｏ）₂ＯＨを形成することはない。また該炭化水素基及び該複素環基は、－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-からなる群から選ばれる少なくとも一種を有していてもよい。Ｒ^na1が複数個存在する場合、これらは同一でも異なっていてもよい。
Ｒ^na10は、置換基を有していてもよい炭素数１～３５の炭化水素基又は置換基を有していてもよい複素環基を表し、Ｒ^na10が複数個存在する場合、これらは同一でも異なっていてもよい。
ａｘは、式（ＩＩ）で表される化合物が有する－ＣＯ₂ ^-及び－Ｓ（Ｏ）₂Ｏ^-の合計数であり、０～１０のいずれかの整数を表す。
ＭＸ^bx+は、ヒドロン又はｂｘ価の金属イオンを表す。ＭＸ^bx+が複数個存在する場合、これらは同一でも異なっていてもよい。ＭＸ^bx+がヒドロンのとき、該ヒドロンは前記－ＣＯ₂ ^-又は－Ｓ（Ｏ）₂Ｏ^-と一緒になって－ＣＯ₂Ｈ及びＳ（Ｏ）₂ＯＨとして存在する。
ｂｘは、１～６のいずれかの整数を表す。
ａｘが０のときｍｘは０であり；ａｘが０以外のとき、ｍｘは、ＭＸ^b+の個数を表す。
ａｘが０のときｎｘは０であり；ａｘが０以外のとき、ｎｘは、ｎｘ＝ｂｘ×ｍｘ／ａｘの関係を満たす数である。］ [In formula (II),
R ¹¹ represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and is contained in the hydrocarbon group-CH. When _2- and the heterocyclic group contain -CH _2- , which does not form a ring, the -CH _2- is replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . May be. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ¹² to R ¹⁵ are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, and a cyano. Representing a group or a nitro group, -CH 2- when the hydrocarbon group contains -CH _2- and the heterocyclic group does not form a ring-CH _2- , the -CH _2- is -O-, -CO-. , -S (O) _2- or -NR ^na- may be replaced. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. The hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ¹² and R ¹³ , R ¹³ and R ¹⁴ , and R ¹⁴ and R ¹⁵ may each be combined with the carbon atom to which they are bonded to form a ring that may have a substituent. When the ring contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- , -NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. The ring may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ¹⁶ is -CO-OR ^na1 , -CO-NH ₂ , -CO-NH (R ^na1 ), -CO-N (R ^na1 ) ₂ , -CO-H, -CO-R ^na1 or -S (O). ) ₂ -R represents ^na1 .
However, when R ¹⁶ represents −CO-NH (R ^na1 ), R ¹² to R ¹⁵ satisfy at least one of (ix) and (iix).
(Ix) At least one of R ¹² to R ¹⁵ is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a halogen atom, and a cyano group. Or, when it represents a nitro group and contains —CH ₂ − contained in the hydrocarbon group and —CH _{2 − in which the heterocyclic group does not form a ring, the —CH 2 −} is —O—, —CO—, It may be replaced with -S (O) ₂ -or-NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
(Iix) Even if at least one set of R ¹² and R ¹³ , R ¹³ and R ¹⁴ , and R ¹⁴ and R ¹⁵ are bonded together with the carbon atom to which they are bonded and have a substituent. When a good ring is formed and the ring contains -CH _2- , which does not form a ring, the -CH _2- is -O-, -CO-, -S (O) _2- or -NR ^na- . May be replaced with. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the ring may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . Of R ¹² to R ¹⁵ , those which do not form a ring are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and a heterocyclic group which may have a substituent. Representing a hydrogen atom, a halogen atom, a cyano group or a nitro group, -CH _{2- contained in the hydrocarbon group and -CH 2- when} the heterocyclic group does not form a ring-CH _2- It may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
X ¹ represents a group represented by the formula (1a-x).

[In the formula (1a-x), R ²¹ to R ²² are independent of each other and may have a hydrocarbon group having 1 to 40 carbon atoms and a heterocycle which may have a substituent. Representing a group, a hydrogen atom, a halogen atom, a cyano group or a nitro group, the —CH ₂ − when the hydrocarbon group contains —CH ₂ − and the heterocyclic group does not form a ring −CH ₂ −. May be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. The hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ²¹ and R ²² may be bonded to each other to form a ring which may have a substituent, and when the ring contains -CH _2- , which does not form a ring, the -CH _2- , -O-, -CO-, -S (O) ₂ -or -NR ^na- may be replaced. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. The ring may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
* 1 represents a bond with an isoindoline ring. ]
R ^na has the same meaning as described above.
R ^na1 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and is contained in the hydrocarbon group -CH _2- and. When the heterocyclic group contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na10- . .. However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . When there are a plurality of R ^na1 , they may be the same or different.
R ^na10 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and when a plurality of R ^na10 are present, they are the same. But it can be different.
ax is the total number of —CO ₂ ⁻ and —S (O) ₂ O ⁻ possessed by the compound represented by the formula (II), and represents an integer of 0 to 10.
MX ^{bx +} represents a hydron or bx-valent metal ion. If there are multiple MX ^{bx +} , they may be the same or different. When MX ^{bx +} is a hydron, the hydron exists as -CO ₂ H and S (O) ₂ OH together with the -CO _2- ^{or -S} (O) ₂ O-.
bx represents an integer of 1 to 6.
When ax is 0, mx is 0; when ax is other than 0, mx represents the number of MX ^{b +} .
When ax is 0, nx is 0; when ax is other than 0, nx is a number that satisfies the relationship nx = bx × mx / ax. ]

The group represented by the formula (1ax) includes the group represented by the formula (2ax).

[In the formula (2a-x), R ²³ to R ²⁴ are independent of each other and may have a hydrocarbon group having 1 to 40 carbon atoms and a heterocycle which may have a substituent. When a group or a hydrogen atom is contained and the hydrocarbon group contains -CH _2- and the heterocyclic group does not form a ring-CH _2- , the -CH _2- is -O-, -CO-. , -S (O) _2- or -NR ^na- may be replaced. However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ^na has the same meaning as described above.
* 2 represents a bond with the isoindoline ring. ]

The compound represented by the formula (II) may be a compound represented by the formula (IIB).

［式（１ａ－ｘｂ）中、Ｒ^21b～Ｒ^22bは、互いに独立に、置換基を有していてもよい炭素数１～４０の炭化水素基、置換基を有していてもよい複素環基、水素原子、ハロゲン原子、シアノ基又はニトロ基を表し、該炭化水素基に含まれる－ＣＨ₂－及び該複素環基が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
Ｒ^21bとＲ^22bとは、互いに結合して置換基を有していてもよい環を形成してもよく、該環が環を構成しない－ＣＨ₂－を含むときの該－ＣＨ₂－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）₂－又は－ＮＲ^nb－に置き換わっていてもよい。ただし、－ＣＨ₂－が置き換わることで－ＣＯＯＨ又は－Ｓ（Ｏ）₂ＯＨを形成することはない。
＊１は、イソインドリン環との結合手を表す。］
Ｒ^nb、Ｒ^nb1は、前記と同じ意味を表す。］ [In formula (IIB),
R ^11b represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and is contained in the hydrocarbon group-CH. When _2- and the heterocyclic group contain -CH _2- , which does not form a ring, the -CH _2- is replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . May be. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^12b to R ^15b are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, and a cyano. Representing a group or a nitro group, the —CH ₂ − when the hydrocarbon group contains —CH ₂ − and the heterocyclic group does not form a ring —— CH ₂ − is —O—, —CO—. , -S (O) _2- or -NR ^nb- may be replaced. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^12b and R ^13b , R ^13b and R ^14b , and R ^14b and R ^15b may be combined with the carbon atom to which they are bonded to form a ring which may have a substituent. When the ring contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^16b is -CO-OR ^nb1 , -CO-NH ₂ , -CO-NH (R ^nb1 ), -CO-N (R ^nb1 ) ₂ , -CO-H, -CO-R ^nb1 or -S (O). ) ₂ -R represents ^nb1 .
However, when R ^16b represents −CO-NH (R ^nb1 ), R ^12b to R ^15b satisfy at least one of (ixb) and (iixb).
(Ixb) At least one of R ^12b to R ^15b is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a halogen atom, and a cyano group. Or, when it represents a nitro group and contains —CH ₂ − contained in the hydrocarbon group and —CH _{2 − in which the heterocyclic group does not form a ring, the —CH 2 −} is —O—, —CO—, It may be replaced with -S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
(Iixb) Even if at least one set of R ^12b and R ^13b , R ^13b and R ^14b , and R ^14b and R ^15b is bonded together with a carbon atom to which each bond has a substituent. When a good ring is formed and the ring contains -CH _2- , which does not form a ring, the -CH _2- is -O-, -CO-, -S (O) _2- or -NR ^nb- . May be replaced with. However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Of R ^12b to R ^15b , those which do not form a ring are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and a heterocyclic group which may have a substituent. Representing a hydrogen atom, a halogen atom, a cyano group or a nitro group, -CH _{2- contained in the hydrocarbon group and -CH 2- when} the heterocyclic group does not form a ring-CH _2- It may be replaced with -O-, -CO-, -S (O) ₂ -or-NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
X ^1b represents a group represented by the formula (1a-xb).

[In the formula (1a-xb), R ^21b to R ^22b may have a hydrocarbon group having 1 to 40 carbon atoms and a substituent which may have a substituent independently of each other. Representing a group, a hydrogen atom, a halogen atom, a cyano group or a nitro group, and containing -CH _2- contained in the hydrocarbon group and -CH _2- when the heterocyclic group does not form a _ring- . May be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^21b and R ^22b may be bonded to each other to form a ring which may have a substituent, and when the ring contains -CH _2- , which does not form a ring, the -CH _2- , -O-, -CO-, -S (O) _2- or -NR ^nb- may be replaced. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
* 1 represents a bond with an isoindoline ring. ]
R ^nb and R ^nb1 have the same meanings as described above. ]

The total number of -CO ₂ H and -S (O) ₂ OH contained in the compound represented by the formula (IIB) is 0.

The group represented by the formula (1a-xb) includes the group represented by the formula (2a-xb).

[In the formula (2a-xb), R ^23b to R ^24b are independent of each other and may have a hydrocarbon group having 1 to 40 carbon atoms and a heterocycle which may have a substituent. When a group or a hydrogen atom is contained and the hydrocarbon group contains -CH _2- and the heterocyclic group does not form a ring-CH _2- , the -CH _2- is -O-, -CO-. , -S (O) _2- or -NR ^nb- may be replaced. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH.
R ^nb has the same meaning as described above.
* 2 represents a bond with the isoindoline ring. ]

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na and R ^nb . The hydrocarbon groups having 1 to 40 carbon atoms represented by, and the hydrocarbon groups having 1 to 35 carbon atoms represented by R ^na1 , R ^na10 , R ^nb1 and R ^nb10 are aliphatic hydrocarbon groups and aromatic hydrocarbons. It may be a group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be in the form of a chain or an alicyclic.

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 Saturated or unsaturated chain hydrocarbon groups include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group and octyl group. Linear alkyl groups such as groups, nonyl groups, decyl groups, undecyl groups, dodecyl groups, heptadecyl groups, octadecyl groups and icosyl groups; isopropyl groups, (2-methyl) propyl groups, isobutyl groups, sec-butyl groups, etc. tert-butyl group, (2-ethyl) butyl group, isopentyl group, neopentyl group, tert-pentyl group, (1-methyl) pentyl group, (2-methyl) pentyl group, (1-ethyl) pentyl group, (3) -Branch-chain alkyl groups such as (ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group, and (3-ethyl) heptyl group; vinyl group, 1-propenyl group , 2-propenyl group (allyl group), isopropenyl group, (1-methyl) ethenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1- (2-propenyl)) ethenyl group , (1,2-Dimethyl) propenyl groups, alkenyl groups such as 2-pentenyl groups; and the like.
R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^na10 , R ^nb and R ^{nb 10} have a saturated or unsaturated chain hydrocarbon group having a carbon number of preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15. It is even more preferably 1 to 10, even more preferably 1 to 8, and particularly preferably 1 to 5. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group represented by R ^na1 , R ^na10 , R ^nb1 and R ^nb10 is preferably 1 to 28, more preferably 1 to 18, and even more preferably 1. It is ~ 13, still more preferably 1 to 8, even more preferably 1 to 6, and particularly preferably 1 to 3.

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 Saturated or unsaturated alicyclic hydrocarbon groups include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and cyclo. Heptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group , 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2 , 2-Dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group and Cycloalkyl groups such as 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 4-cyclohexylcyclohexyl group; cyclohexenyl group (eg cyclohex-2-ene, cyclohexa-3). -En), cycloalkenyl groups such as cycloheptenyl group, cyclooctenyl group; norbornan group, adamantyl group, bicyclo [2.2.2] octane and the like can be mentioned. R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 have a carbon number of preferably 3 to 30, more preferably 3 to 20, and even more preferably 4 to 20. It is even more preferably 4 to 15, even more preferably 5 to 15, particularly preferably 5 to 10, and among them, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Is particularly preferred.

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb . , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 may be a combination of the above-mentioned chain hydrocarbon group and alicyclic hydrocarbon group. Often, for example, one or more alicyclic hydrocarbons such as cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, cyclohexylethyl group and the like. Examples thereof include an alkyl group to which a group is bonded. The carbon number is preferably 4 to 30, more preferably 4 to 20, and even more preferably 4 to 15.

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb . , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 include phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,3-dimethylphenyl group, as aromatic hydrocarbon groups. 2,4-Dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, o-isopropylphenyl group, m-isopropylphenyl Group, p-isopropylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, mesityl group, 2,6-bis (2-propyl) phenyl group, 2, 4,6-trimethylphenyl group, 1-naphthyl group, 2-naphthyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, fluorenyl group , Aromatic hydrocarbon groups such as phenyl group and anthryl group; and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 15.

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb . , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 are not particularly limited as long as they are hydrocarbon groups having an aromatic hydrocarbon ring, and the above-mentioned chain hydrocarbon groups, At least one of the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be a group in combination with the aromatic hydrocarbon group mentioned above, and may be a benzyl group, a 2-methylbenzyl group, or a 3-methyl group. Aralkyl groups such as benzyl group, 4-methylbenzyl group, phenylethyl group, phenylpropyl group and 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group); phenylethynyl group and the like. Arylalkynyl group; a phenyl group to which one or more phenyl groups such as a biphenylyl group and a terphenylyl group are bonded; a cyclohexylmethylphenyl group, a benzylphenyl group, a (dimethyl (phenyl) methyl) phenyl group; and the like, and carbon thereof. The number is preferably 7 to 30, more preferably 7 to 20, and even more preferably 7 to 15.

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 may have a monovalent substituent or a divalent substituent. The divalent substituent preferably has two bonds attached to the same carbon atom to form a double bond.
As the monovalent substituent,
An alkylsulfanil group having 1 to 10 carbon atoms such as a methylthio group, an ethylthio group, a propylthio group and a butylthio group;
Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
Nitro group;
Cyano group;
Trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoroheptyl group, perfluorooctyl group, perfluorononyl group, A hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms in which all hydrogen atoms such as a perfluorodecyl group, a perfluorocyclohexyl group, and a perfluorophenyl group are substituted with a fluorine atom;
* -CO-SH;
* -CO-S-CH ₃ , * -CO-S-CH ₂ CH ₃ , * -CO-S-CH ₂ -CH ₂ -CH ₃ , * -CO-S-CH ₂ -CH ₂ -CH _2- A carbonyl group bonded to a sulfur atom bonded to an alkyl group such as CH ₃ (the alkyl group has 1 to 10 carbon atoms);
* _-Carbonyl group bonded to a sulfur atom bonded to an aryl group such as CO-SC 6H ₅ (the aryl group has 6 to 20 carbon atoms);
* -OP (O) (OR ^nb2 ) ₂ ;
* -Si (R ^nb2 ) (R ^nb3 ) (R ^nb4 ); etc.
In the above formula, R ^nb2 , R ^nb3 , and R ^nb4 may be the same or different, and may have a substituent, respectively. A hydrocarbon group having 1 to 35 carbon atoms or a substituent may be used. Representing a heterocyclic group which may be possessed, -CH _2- contained in the hydrocarbon group and -CH _2- when the heterocyclic group does not form a ring-CH _2- is -O. -, -CO-, -S (O) _2- , -N ^nb10 -may be replaced. However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. R ^nb10 is the same as described above. The specific examples and preferable ranges of R ^nb2 , R ^nb3 , and R ^nb4 are the same as those of R ¹ except that the examples having 36 or more carbon atoms are not included.

The divalent substituent includes a thioxo group, an imino group, an imino group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted with an aryl group having 6 to 20 carbon atoms. And so on. Examples of the imino group substituted with the alkyl group include CH ₃ -N =, CH ₃ -CH ₂ -N =, CH _3- (CH ₂ ) ₂ -N =, CH _3- (CH ₂ ) ₃ -N =, and the like. Can be mentioned. Examples of the imino group substituted with the aryl group include C ₆ H ₅ -N = and the like.

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 as substituents for the hydrocarbon groups.
Halogen atom; Nitro group; Cyano group; Hydrocarbon group having 1 to 20 carbon atoms in which all hydrogen atoms are replaced by fluorine atom; Thiocarbonyl group; * -OP (O) (OR ^nb2 ) ₂ ; * -Si (R) ^nb2 ) (R ^nb3 ) (R ^nb4 ); etc. are preferable.
Halogen atoms; nitro groups; cyano groups; hydrocarbon groups having 1 to 20 carbon atoms in which all hydrogen atoms are replaced by fluorine atoms; thiocarbonyl groups; etc. are more preferable.
Fluorine atom, chlorine atom, bromine atom; nitro group; cyano group; hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are substituted with fluorine atom; thiocarbonyl group; and the like are more preferable.

In the case where a is an integer of 1 to 10 in the formula (I), or in the compound represented by the formula (IA) or the formula (II), the hydrocarbon group is -CH _2- , -O-,-. It may have a group (ie, group (Z1)) formed by substituting CO-, -S (O) _2- , -NR ^na- . Further, when a is 0 in the formula (I), or in the compound represented by the formula (IB) or the formula (IIB), the hydrocarbon group is -CH _2- , -O-, -CO-,. It may have a group (ie, group (Z2)) formed by substituting —S (O) ₂ − or −NR ^nb −.
As a group (Z1) and a group (Z2),
Methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, An oxy group having 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms such as an octyloxy group, a nonyloxy group, a phenyloxy group, and an o-tolyloxy group bonded to one side;
Epoxy group;
Holmil group;
The acetyl group, propanoyl group, butanoyl group, tert-butanoyl group, pentanoyl group, hexanoyl group, (2-ethyl) hexanoyl group, heptanoyle group, octanoyl group, nonanoyl group, benzoyl group and the like have 2 to 22 carbon atoms, preferably 2 to 22 carbon atoms. Acyl groups with 2-12 carbon atoms (preferably alkanoyl groups);
Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl) hexyloxycarbonyl group, heptyloxycarbonyl group and octyloxycarbonyl group An oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms such as a group, a nonyloxycarbonyl group, a phenyloxycarbonyl group, and an o-tolyloxycarbonyl group is bonded;
Amino group;
N-methylamino group, N, N-dimethylamino group, N-ethylamino group, N, N-diethylamino group, N-propylamino group, N, N-dipropylamino group, N-isopropylamino group, N, N-diisopropylamino group, N-butylamino group, N, N-dibutylamino group, N-isobutylamino group, N, N-diisobutylamino group, N-sec-butylamino group, N, N-disec-butyl Amino group, N-tert-butylamino group, N, N-ditert-butylamino group, N-pentylamino group, N, N-dipentylamino group, N- (1-ethylpropyl) amino group, N, N -Di (1-ethylpropyl) amino group, N-hexylamino group, N, N-dihexylamino group, N- (2-ethyl) hexylamino group, N, N-di (2-ethyl) hexylamino group, N-heptylamino group, N, N-diheptylamino group, N-octylamino group, N, N-dioctylamino group, N-nonylamino group, N, N-dinonylamino group, N-phenylamino group, N, N -Diphenylamino group, N, N-ethylmethylamino group, N, N-propylmethylamino group, N, N-isopropylmethylamino group, N, N-butylmethylamino group, N, N-tert-butylmethylamino An amino group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms, preferably 1 to 20 carbon atoms, such as a group and an N, N-phenylmethylamino group;
Sulfamoyl group;
N-methylsulfamoyl group, N, N-dimethylsulfamoyl group, N-ethylsulfamoyl group, N, N-diethylsulfamoyl group, N-propylsulfamoyl group, N, N-dipropyls Rufamoyl group, N-isopropylsulfamoyl group, N, N-diisopropylsulfamoyl group, N-butylsulfamoyl group, N, N-dibutylsulfamoyl group, N-isobutylsulfamoyl group, N, N-diisobutylsulfamoyl group, N-sec-butylsulfamoyl group, N, N-disec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N, N-ditert-butylsul Famoyl group, N-pentylsulfamoyl group, N, N-dipentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N, N-di (1-ethylpropyl) sulfamoyl group, N-hexyl Sulfamoyl group, N, N-dihexyl sulfamoyl group, N- (2-ethyl) hexyl sulfamoyl group, N, N-di (2-ethyl) hexyl sulfamoyl group, N-heptyl sulfamoyl Group, N, N-diheptyl sulfamoyl group, N-octyl sulfamoyl group, N, N-dioctyl sulfamoyl group, N, N-octylmethyl sulfamoyl group, N-nonyl sulfamoyl group, N, N-dinonyl sulfamoyl group, N-phenyl sulfamoyl group, N, N-diphenyl sulfamoyl group, N, N-ethylmethyl sulfamoyl group, N, N-propylmethyl sulfamoyl group, One of N, N-isopropylmethylsulfamoyl group, N, N-butylmethylsulfamoyl group, N, N-tert-butylmethylsulfamoyl group, N, N-phenylmethylsulfamoyl group, etc. A sulfamoyl group substituted with two hydrocarbon groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms;
Formylamino group;
Acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanolamino group, pentanoylamino group, hexanoylamino group, (2-ethyl) hexanoylamino group, heptanoyleamino group, octa Noylamino group, nonanoylamino group, decanoyylamino group, undecanoylamino group, dodecanoylamino group, henicosanoylamino group, benzoylamino group, etc. have 1 to 22 carbon atoms, preferably 1 to 12 carbon atoms. Arcanoylamino group;
Hydroxy group;
Formyloxy group, acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl) hexanoyloxy group, heptanoiloxy An alkanoyloxy group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms such as a group, an octanoyloxy group, a nonanoyloxy group and a benzoyloxy group;
Methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl) hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, phenyl A sulfonyl group substituted with a hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms such as a sulfonyl group and a p-tolylsulfonyl group;
Carbamic group;
N-Methylcarbamoyl group, N, N-dimethylcarbamoyl group, N-ethylcarbamoyl group, N, N-diethylcarbamoyl group, N-propylcarbamoyl group, N, N-dipropylcarbamoyl group, N-isopropylcarbamoyl group, N , N-diisopropylcarbamoyl group, N-butylcarbamoyl group, N, N-dibutylcarbamoyl group, N-isobutylcarbamoyl group, N, N-diisobutylcarbamoyl group, N-sec-butylcarbamoyl group, N, N-disec- Butylcarbamoyl group, N-tert-butylcarbamoyl group, N, N-ditert-butylcarbamoyl group, N-pentylcarbamoyl group, N, N-dipentylcarbamoyl group, N- (1-ethylpropyl) carbamoyl group, N, N-di (1-ethylpropyl) carbamoyl group, N-hexylcarbamoyl group, N, N-dihexylcarbamoyl group, N- (2-ethyl) hexylcarbamoyl group, N, N-di (2-ethyl) hexylcarbamoyl group , N-Heptylcarbamoyl group, N, N-diheptylcarbamoyl group, N-octylcarbamoyl group, N, N-dioctylcarbamoyl group, N-nonylcarbamoyl group, N, N-dinonylcarbamoyl group, N-phenylcarbamoyl group. , N, N-diphenylcarbamoyl group, N, N-ethylmethylcarbamoyl group, N, N-propylmethylcarbamoyl group, N, N-isopropylmethylcarbamoyl group, N, N-butylmethylcarbamoyl group, N, N-tert -Carbamoyl group substituted with one or two hydrocarbon groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, such as a butylmethylcarbamoyl group and an N, N-phenylmethylcarbamoyl group;
* -COCOR ^nb2 ;
* -OCON (R ^nb2 ) ₂ ;
* -N (R ^nb2 ) COOR ^nb2 ; etc.
In the above formula, R ^nb2 may be the same or different, and has the same meaning as described above.

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 may be monocyclic or polycyclic, preferably a heterocycle containing a heteroatom as a component of the ring. Is. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 have a carbon number of preferably 2 to 30, more preferably 3 to 22, and even more preferably 3 to 20. It is even more preferably 3 to 18, even more preferably 3 to 15, and particularly preferably 3 to 14.

Examples of the heterocycle containing only a nitrogen atom as a heteroatope include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; pyrol such as 2,5-dimethylpyrazole, 2-methylpyrazole and 3-methylpyrazole. Pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole and other 5-membered ring-based unsaturated heterocycles; pyrimidine, pyrazine, 1,3, etc. such as pyridine, pyridazine, 6-methylpyrimidine 6-membered ring-based unsaturated heterocycles such as 5-triazine; indazole, indolin, isoindolin, indole, indolidine, benzoimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro (3-methyl) quinoxalin, 3 -Fused bicyclic heterocycles such as quinoxalin such as methylquinoxalin, quinazoline, cinnoline, phthalazine, naphthylidine, purine, pteridine, benzopyrazole, benzopiperidin; fused tricyclic heterocycles such as carbazole, aclysine and phenazine; Examples include the represented ring.

（式中、＊は結合手を表す）

(In the formula, * represents a bond)

Examples of the heterocycle containing only an oxygen atom as a hetero atom include monocyclic saturated heterocycles such as oxylane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, and 1-cyclopentyldioxolane; 1,4. -Bicyclic saturated heterocycles such as dioxaspiro [4.5] decane and 1,4-dioxaspiro [4.5] nonane; α-acetlactone, β-propiolactone, γ-butyrolactone, δ-valerolactone and the like. Lactone-based heterocycles; 5-membered ring-based unsaturated heterocycles such as furan such as 2,3-dimethylfuran and 2,5-dimethylfuran; 6-membered ring-based unsaturated heterocycles such as 2H-pyran and 4H-pyran; Examples thereof include benzopyran such as 1-benzofuran and 4-methylbenzopyran, fused bicyclic heterocycles such as benzodioxol, chroman and isochroman; condensed tricyclic heterocycles such as xanthene and dibenzofuran; and the like.

As a heterocycle containing only a sulfur atom as a heteroatom, a 5-membered ring-based saturated heterocycle such as dithiolane; a 6-membered ring-based saturated heterocycle such as thiane, 1,3-dithian, and 2-methyl1,3-dithian; Five-membered ring-based unsaturated heterocycles such as thiophenes such as 3-methylthiophene and 2-carboxythiophene, 4H-thiopyran, benzothiopyrans such as benzotetrahydrothiopyrane; fused bicyclic heterocycles such as benzothiophene; thianthene, dibenzo Condensed tricyclic heterocycles such as thiophene; and the like.

Examples of the heterocycle containing a nitrogen atom and an oxygen atom as heteroatomes include monocyclic saturated heterocycles such as morpholin, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, and 2-methyl-2-piperidone; 4 -Oxazole such as methyloxazole, monocyclic unsaturated heterocycle such as isooxazole such as 2-methylisoxazole and 3-methylisoxazole; condensation of benzoxazole, benzoisoxazole, benzoxazine, benzodioxane, benzoimidazoline and the like. Bicyclic heterocycles; fused tricyclic heterocycles such as phenoxazine; and the like.

Examples of the heterocycle containing a nitrogen atom and a sulfur atom as heteroatoms include a monocyclic heterocycle such as thiazole such as 3-methylthiazole and 2,4-dimethylthiazole; a fused bicyclic heterocycle such as benzothiazole; phenothiazine and the like. Condensed tricyclic heterocycle; etc.

The heterocyclic group may be a group in which the above-mentioned hydrocarbon groups are combined, and examples thereof include a tetrahydrofurylmethyl group and a methyltetrahydrofuryl group.
The bond position of the above heterocycle is a portion where an arbitrary hydrogen atom contained in each ring is eliminated.

When the heterocyclic group represented by R ¹ to R ⁹ , R ^1a to R ^9a , R ¹¹ to R ¹⁵ , and R ²¹ to R ²⁴ contains -CH _2- , which does not form a ring, the -CH _2- , -O-, -CO-, -S (O) _2- or -NR ^na- may be substituted. When −CH ₂ − is substituted, the heterocyclic groups represented by R ¹ to R ⁹ , R ^1a to R ^9a , R ¹¹ to R ¹⁵ , and R ²¹ to R ²⁴ include the above group (Z1). ..
When the heterocyclic groups represented by R ¹ to R ⁵ , R ⁷ , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , and R ^17b to R ^24b contain —CH _2- , which does not form a ring, The -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . When −CH ₂ − is substituted, the heterocyclic groups represented by R ¹ to R ⁵ , R ⁷ , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , and R ^17b to R ^24b are described above. Includes group (Z2).

When the heterocycle contains a nitrogen atom as a constituent element thereof, the above-mentioned R ¹ may be bonded to the nitrogen atom.

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ²¹ And R ²² , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a and R ^5a , R ^6a and R ^7a , R ^8a and R ^9a , R ^2b and R ^3b , R ^3b and R ^4b , R ^{4 b} and R. If ^5b , R ^6b and R ^7b , R ^12b and R ^13b , R ^13b and R ^14b , R ^14b and R ^15b , R ^17b and R ^18b , or R ^21b and R ^22b combine to form a ring, this ring May be a hydrocarbon ring or a heterocycle. Examples of the hydrocarbon ring include an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring.

The aliphatic hydrocarbon ring includes a cyclopropane ring, a methylcyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptan ring, a methylcyclohexane ring, a 1,1-dimethylcyclohexane ring, and a 1,2-dimethylcyclohexane ring. , 1,3-dimethylcyclohexane ring, 1,4-dimethylcyclohexane ring, cyclooctane ring, 1,3,5-trimethylcyclohexane ring, 1,1,3,3-tetramethylcyclohexane ring, pentylcyclohexane ring, octylcyclohexane Cycloalkane rings such as rings and cyclohexanecyclohexane rings; cycloalkene rings such as cyclohexene rings, cycloheptene rings and cyclooctene rings; norbornan, adamantan, bicyclo [2.2.2] octane and the like. The aliphatic hydrocarbon ring has, for example, 3 to 30, preferably 3 to 20, more preferably 4 to 20, still more preferably 4 to 15, and even more preferably 5. It is about 15, and particularly preferably 5 to 10.

Aromatic hydrocarbon rings include benzene, toluene, o-xylene, m-xylene, p-xylene, isopropylbenzene, tert-butylbenzene, mecitylene, 1,5-bis (2-propyl) benzene, naphthalene, 1, 2,3,4-tetrahydronaphthalene, fluorene, benzene, anthracene; and the like. The number of carbon atoms of the aromatic hydrocarbon group is, for example, 6 to 30, preferably 6 to 20, and more preferably 6 to 15.

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ²¹ And R ²² , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a and R ^5a , R ^6a and R ^7a , R ^8a and R ^9a , R ^2b and R ^3b , R ^3b and R ^4b , R ^{4 b} and R. Rings formed by combining ^5b , R ^6b and R ^7b , R ^12b and R ^13b , R ^13b and R ^14b , R ^14b and R ^15b , R ^17b and R ^18b , or R ^21b and R ^22b have substituents. You may have. The substituents include R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , and R ^17b to R ^24b . , R ^na , R ^nb , R ^na1 , R ^na10 , R ^nb1 and the same substituents that the hydrocarbon groups represented by R ^nb10 may have.

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ²¹ And R ²² , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a and R ^5a , R ^6a and R ^7a , or R ^8a and R ^9a combined to form a ring that does not form a ring-CH _2- When, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . When -CH ₂ -is replaced, R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ²¹ and R ²² , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a and R ^5a , R ^6a and R ^7a or R ^8a and R ^9a are combined to form. The ring contains the above group (Z1).

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ^2b and R ^3b , R ^3b and R ^4b , R ^4b and R ^5b , R ^6b and R ^7b , R ^12b and R ^13b , R ^13b . When the ring formed by the combination of R 14b and R ^14b , R ^14b and R ^15b , R ^17b and R ^18b , or R ^21b and R ^22b contains -CH _2- , which does not form a ring, the -CH _2- It may be substituted with —O—, —CO—, —S (O) ₂ -or —NR ^nb −. When -CH ₂ -is replaced, R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ^2b and R ^3b , R ^3b and R ^4b , R ^4b and R ^5b , R ^6b . The ring formed by combining R ^7b , R ^12b and R ^13b , R ^13b and R ^14b , R ^14b and R ^15b , R ^17b and R ^18b , or R ^21b and R ^22b contains the above group (Z2).

Also R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R. ²¹ and R ²² , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a and R ^5a , R ^6a and R ^7a , R ^8a and R ^9a , R ^2b and R ^3b , R ^3b and R ^4b , R ^4b and When R ^5b , R ^6b and R ^7b , R ^12b and R ^13b , R ^13b and R ^14b , R ^14b and R ^15b , R ^17b and R ^18b , or R ^21b and R ^22b combine to form a heterocycle. These heterocycles are R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , A complex ring similar to the complex ring represented by R ^na , R ^nb , R ^na1 , R ^na10 , R ^nb1 and R ^nb10 may be formed. R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ^2a And R ^3a , R ^3a and R ^4a , R ^4a and R ^5a , R ^2b and R ^3b , R ^3b and R ^4b , R ^4b and R ^5b , R ^6b and R ^7b , R ^12b and R ^13b , R ^13b and R. When ^14b or R ^14b and R ^15b are combined to form a heterocycle, the heterocyclic group is R ² to R ⁵ , R ^2a to R ^5a , R ^2b to R ^5b , R ¹² to R ¹⁵ or It has a ring structure of two or more rings together with a benzene ring to which R ^12b to R ^15b are bonded. Examples of the heterocycle having a ring structure of two or more rings include a heterocycle having a structure of the following formula.

(The benzene ring in the formula corresponds to the benzene ring in the isoindoline structure of the compound represented by the formula (I)).

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ²¹ And R ²² , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a and R ^5a , R ^6a and R ^7a , R ^8a and R ^9a , R ^2b and R ^3b , R ^3b and R ^4b , R ^{4 b} and R. ^{When 5b} , R ^6b and R ^7b , R ^12b and R ^13b , R ^13b and R ^14b , R ^14b and R ^15b , R ^17b and R ^18b , or R ^21b and R ^22b combine to form a heterocycle. The heterocycle may have a substituent. The substituents include R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , and R ^17b to R ^24b . , R ^na , R ^nb , R ^na1 , R ^na10 , R ^nb1 and the same substituents that the hydrocarbon groups represented by R ^nb10 may have.

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ²¹ ~ R ²⁴ , R ²¹ and R ²² , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a and R ^5a , R ^6a and R ^7a or R ^8a and R ^9a are combined to form a ring. When -CH _2- is contained, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . When -CH ₂ -is replaced, R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ²¹ and R ²² , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a and R ^5a , R ^6a and R ^7a or R ^8a and R ^9a are combined to form. The heterocycle contains the above group (Z1).

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ^2b and R ^3b , R ^3b and R ^4b , R ^4b and R ^5b , R ^6b and R ^7b , R ^12b . And R ^13b , R ^13b and R ^14b , R ^14b and R ^15b , R ^17b and R ^18b , or when the heterocycle formed by combining R ^21b and R ^22b contains -CH _2- , which does not form a ring. The -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb- . When -CH ₂ -is replaced, R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ^2b and R ^3b , R ^3b and R ^4b , R ^4b and The heterocycle formed by combining R ^5b , R ^6b and R ^7b , R ^12b and R ^13b , R ^13b and R ^14b , R ^14b and R ^15b , R ^17b and R ^18b , or R ^21b and R ^22b is described above. Includes group (Z2).

When the heterocycle contains a nitrogen atom as a constituent element thereof, the above-mentioned R ^1b may be bonded to the nitrogen atom.

R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , R ^nb , R ^na1 and R ^nb1 may have a substituent. The substituents include R ¹ to R ⁹ , R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , and R ^17b to R ^24b . , R ^na , R ^nb , R ^na1 and the same substituents that the hydrocarbon groups represented by R ^nb1 may have. When the heterocycle contains a nitrogen atom as a constituent element thereof, the above-mentioned hydrocarbon group may be bonded to the nitrogen atom as a substituent.

At least one of R ^1a to R ^9a , preferably at least one of R ^6a to R ^9a , more preferably one of R ^6a and R ^7a and one of R ^8a and R ^9a are preferably hydrocarbon groups. .. When R ^1a to R ^9a , R ¹¹ to R ¹⁶ or R ²¹ to R ²⁴ are hydrocarbon groups, -CH _2- contained in the hydrocarbon group is -O-, -CO-, -S (O). It may be replaced with ₂ -or -NR ^na- . However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Further, when one of R ^6a and R ^7a and one of R ^8a and R ^9a are hydrocarbon groups and -CH ₂ -contained in the hydrocarbon group is replaced, the other of R ^6a and R ^7a is replaced with the other. The other of R ^8a and R ^9a is preferably one selected from the group consisting of CN, COO ⁻ , S (O) ₂ O ⁻ , and more preferably CN. Examples of the group in which -CH ₂ -is replaced include -CO-OR ^na2 (this group is replaced by two -CH 2- of -CH ₂ -CH ₂ -R ^na ₂ , respectively, with -CO- and -O-, respectively. (This group is a group in which _two -CH ₂ -H of -CH ₂ -CH ₂ -H are replaced by -CO- and -NH-, respectively), -CO. -NH (R ^na2 ) (this group is a group in which two -CH 2- of -CH ₂ -CH ₂ -R ^na ₂ are replaced by -CO- and -NH-, respectively), -CO-N (R). ^na2 ) ₂ (This group is a group in which two -CH _2- of -CH ₂ -CH ₂ -R ^na2 are replaced by -CO- and -NR ^na2- , respectively), -CO-H (this group is , -CH ₂ -H-CH ₂ -is replaced by -CO-), -CO-R ^na2 (This group is -CH ₂ -R na 2 -CH ₂ ^-replaced by -CO- (It is a group) or -S (O) ₂ -R ^na2 (this group is a group in which -CH 2- of -CH ₂ -R ^na ₂ is replaced by -S (O) _2- ) and the like. ..

R ^na2 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and is contained in the hydrocarbon group-CH _2- . And when the heterocyclic group contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na10- . good. However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Further, the hydrocarbon group or the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . R ^na10 is the same as described above. Specific examples and preferable ranges of R ^na 2 are the same as those of R ^1a except that the examples having 36 or more carbon atoms are not included. When a plurality of R ^na2 are contained, they may be the same or different.

R ^na2 may have a group (Z1). The preferred group (Z1) that R ^na2 may have is a halogen atom such as a chlorine atom; a sulfamoyl group; a hydroxy group; an oxy group in which a hydrocarbon group having 1 to 10 carbon atoms such as a methoxy group is bonded to one side. An oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms such as a methoxycarbonyl group is bonded; -SO ₂ NH ₂ and the like are preferable. Further, R ^na2 may have −CO ₂ ⁻ , —S (O) ₂ O ⁻ , and the like.

When R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , and R ^17b to R ^24b are hydrocarbon groups, -CH _2- contained in the hydrocarbon group is -O-, -CO-, -S. (O) It may be replaced with ₂ -or -NR ^nb- . The groups in which -CH ₂ -replaced are, for example, -CO-OR ^nb5 , -CO-NH ₂ , -CO-NH (R ^nb5 ), -CO-N (R ^nb5 ) ₂ , -CO-H,-. Examples thereof include CO-R ^nb5 or -S (O) ₂ -R ^nb5 .
R ^nb5 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and is contained in the hydrocarbon group-CH _2- . And when the heterocyclic group contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^nb10- . good. However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. R ^nb10 is the same as described above. Specific examples and preferable ranges of R ^nb 5 are the same as those of R ^nb 1 except that the examples having 36 or more carbon atoms are not included. When a plurality of R ^nb5 are included, they may be the same or different.

-CO-OR ^na1 , -CO-OR ^na2 , -CO-OR ^nb1 , -CO-OR ^nb5 include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxy. Carbonyl group, hexyloxycarbonyl group, (2-ethyl) hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyl An oxycarbonyl group or the like to which a hydrocarbon group having 1 to 35 carbon atoms such as an oxycarbonyl group and an icosyloxycarbonyl group is bonded is preferable, and a oxycarbonyl group or the like to which a hydrocarbon group having 1 to 10 carbon atoms is bonded is more preferable. Can be mentioned.

-CO-NH (R ^na1 ), -CO-NH (R ^na2 ), -CO-NH (R ^nb1 ), -CO-NH (R ^nb5 ), -CO-N (R ^na1 ) ₂ , -CO-N As (R ^na2 ) ₂ , -CO-N (R ^nb1 ) ₂ , -CO-N (R ^nb5 ) ₂ , N-methylcarbamoyl group, N-ethylcarbamoyl group, N-propylcarbamoyl group, N-isopropylcarbamoyl Group, N-butylcarbamoyl group, N-isobutylcarbamoyl group, N-sec-butylcarbamoyl group, N-tert-butylcarbamoyl group, N-pentylcarbamoyl group, N- (1-ethylpropyl) carbamoyl group, N-hexyl Carbamoyl group, N- (2-ethyl) hexylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group, N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group. , Carbamoyl group substituted with one hydrocarbon group having 1 to 35 carbon atoms such as N-icosylcarbamoyl group and N-phenylcarbamoyl group;
N, N-dimethylcarbamoyl group, N, N-ethylmethylcarbamoyl group, N, N-diethylcarbamoyl group, N, N-propylmethylcarbamoyl group, N, N-dipropylcarbamoyl group, N, N-isopropylmethylcarbamoyl Group, N, N-diisopropylcarbamoyl group, N, N-tert-butylmethylcarbamoyl group, N, N-diisobutylcarbamoyl group, N, N-disec-butylcarbamoyl group, N, N-ditert-butylcarbamoyl group , N, N-butylmethylcarbamoyl group, N, N-dibutylcarbamoyl group, N, N-butyloctylcarbamoyl group, N, N-dipentylcarbamoyl group, N, N-di (1-ethylpropyl) carbamoyl group, N , N-dihexylcarbamoyl group, N, N-di (2-ethyl) hexylcarbamoyl group, N, N-diheptylcarbamoyl group, N, N-octylmethylcarbamoyl group, N, N-dioctylcarbamoyl group, N, N -Dinonylcarbamoyl group, N, N-decylmethylcarbamoyl group, N, N-undecylmethylcarbamoyl group, N, N-dodecylmethylcarbamoyl group, N, N-icosylmethylcarbamoyl group, N, N-phenylmethyl A carbamoyl group substituted with two hydrocarbon groups having 1 to 35 carbon atoms such as a carbamoyl group and an N, N-diphenylcarbamoyl group is preferable, and more preferably one or two hydrocarbon groups having 1 to 10 carbon atoms. Examples thereof include a hydrocarbon group substituted with. In -CO-NH (R ^na2 ), -CO-N (R ^na2 ) ₂ , in the carbamoyl group substituted with the one or two hydrocarbon groups ^, the hydrocarbon group has -COO-. May be good.

-CO-R ^na1 , -CO-R ^na2 , -CO-R ^nb1 and -CO-R ^nb5 include acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanol group, pentanoyl group and hexanoyl group. (2-Ethyl) Hydrocarbons such as hexanoyl group, heptanoyle group, octanoyl group, nonanoyl group, decanoyle group, undecanoyl group, dodecanoyl group, henicosanoyl group, benzoyl group, phenylmethylcarbonyl group, phenylethylcarbonyl group and phenylpropylcarbonyl group. A carbonyl group which is a group to which a group having 1 to 35 carbon atoms is bonded is preferable, and a carbonyl group which is a hydrocarbon group to which a group having 1 to 10 carbon atoms is bonded is preferable. In -CO-R ^na1 , -CO-R ^na2 , -CO-R ^nb1 , and -CO-R ^nb5 , in the carbonyl group to which the hydrocarbon group is bonded, the hydrocarbon group is a halogen atom such as a chlorine atom; a sulfamoyl group. It has an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms such as a methoxy group is bonded to one side; an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms such as a methoxycarbonyl group is bonded; and the like. May be. In -CO-R ^a1 and -CO-R ^na2 , in the carbonyl group to which the hydrocarbon group is bonded, the hydrocarbon group may have -COO- ^, S (O) _2O ^- and the like. Further, as -CO-R ^na1 , -CO-R ^na2 , -CO-R ^nb1 and -CO-R ^nb5 , a formyl group is also preferable.

-S (O) ₂ -R ^na1 , -S (O) ₂ -R ^na2 , -S (O) ₂ -R ^nb1 , -S (O) ₂ -R ^nb5 include methyl sulfonyl groups and ethyl sulfonyl groups. Propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl) hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, A sulfonyl group to which a hydrocarbon group having 1 to 35 carbon atoms such as an icosylsulfonyl group, a phenylsulfonyl group, and a p-tolylsulfonyl group is bonded is preferable, and a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms is bonded is more preferable. The basis etc. can be mentioned.

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a And R ^5a , R ^2b and R ^3b , R ^3b and R ^4b , R ^4b and R ^5b , R ^12b and R ^13b , R ^13b and R ^14b , and the ring formed by R ^14b and R ^15b is the equation (I). , Formula (IA), formula (IB), formula (II) or formula (IIB) is condensed with benzene of the isoindoline skeleton. R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a . And R ^5a , R ^2b and R ^3b , R ^3b and R ^4b , R ^4b and R ^5b , R ^12b and R ^13b , R ^13b and R ^14b , and the ring formed by R ^14b and R ^15b and the benzene ring. The fused ring structure includes inden, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluorantene, acephenanthrylene, aceanthrylene, triphenylene, pyrene, chrysen, N-methylphthalimide, N- (1). -Fenylethyl) Hydrocarbon-based condensed ring structures such as phthalimide and tetracene and their partial reductions (eg, 9,10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, etc.); indol, isoindole, indazole, etc. Nitrogen-containing fused heterocycles such as quinoline, isoquinoline, phthalazine, quinoxalin, quinazoline, cinnoline, carbazole, carboline, phenanthridine, aclysine, perimidine, phenanthroline, and phenazine; and partially reduced compounds thereof; containing 3-hydrobenzofuran 2-one and the like. Examples thereof include an oxygen-fused heterocycle and a partially reduced product thereof.

The ring formed by R ⁶ and R ⁷ or the ring formed by R ⁸ and R ⁹ is bound to exomethylene (C = CH ₂ ) of the isoindoline skeleton of formula (I). Further, the ring formed by R ^6a and R ^7a or the ring formed by R ^8a and R ^9a is bound to exomethylene (C = CH ₂ ) of the isoindoline skeleton of the formula (IA). This exomethylene (C = CH) is a ring formed by R ⁶ and R ⁷ , a ring formed by R ⁸ and R ⁹ , a ring formed by R ^6a and R ^7a , or a ring formed by R ^8a and R ^9a . As a structure containing ₂ ), for example, a structure in which a carbonyl group, an exomethylene, and a carbonyl group are arranged in this order as shown in Group A below can be exemplified. ** represents a bond with the isoindoline skeleton.

[Group A]

[In the formula, R ²⁵ and R ²⁶ are independent of each other, a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, or a hydrogen atom. -CH ₂ -contained in the hydrocarbon group may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) _2O ^— as a substituent. Specific examples and preferable examples of R ²⁵ and R ²⁶ include examples of the above R ^1a excluding the example having 36 or more carbon atoms. ]

The ring formed by R ²¹ and R ²² is bound to the exomethylene (C = CH ₂ ) of the isoindoline skeleton of the formula (II), and the ring formed by R ²¹ and R ²² is this exomethylene (C). As a structure containing = CH ₂ ), for example, a structure in which a carbonyl group, an exomethylene, and a carbonyl group are arranged in this order as in group B below can be exemplified. ** represents a bond with the isoindoline skeleton.

[Group B]

[In the formula, R ²³ and R ²⁴ are the same as above. ]
The ring formed by R ^17b and R ^18b is bound to exomethylene (C = CH ₂ ) of the isoindoline skeleton of formula (IB). Further, the ring formed by R ^21b and R ^22b is bound to exomethylene (C = CH ₂ ) of the isoindoline skeleton of the formula (IIB). The ring formed by R ^17b and R ^18b or the ring formed by R ^21b and R ^22b can be cited as a structure containing this exomethylene (C = CH ₂ ). An example is a structure in which methylene and a carbonyl group are arranged in this order. ** represents a bond with the isoindoline skeleton.

[Group C]

[In the formula, R ^23b and R ^24b have the same meanings as described above. ]

R ² and R ³ , R ³ and R ⁴ , R ⁴ and R ⁵ , R ¹² and R ¹³ , R ¹³ and R ¹⁴ , R ¹⁴ and R ¹⁵ , R ^2a and R ^3a , R ^3a and R ^4a , R ^4a . And R ^5a , R ^2b and R ^3b , R ^3b and R ^4b , R ^4b and R ^5b , R ^12b and R ^13b , R ^13b and R ^14b , and the rings formed by R ^14b and R ^15b have substituents. You may be doing it. The substituents include R ¹¹ to R ¹⁵ , R ²¹ to R ²⁴ , R ^1a to R ^9a , R ^1b to R ^5b , R ^7b , R ^11b to R ^15b , R ^17b to R ^24b , R ^na , and R ^nb . , R ^na1 , R ^na10 , R ^nb1 and the same substituents that the hydrocarbon groups represented by R ^nb10 may have.

As halogens represented by R ¹² to R ¹⁵ , R ²¹ to R ²² , R ^2a to R ^9a , R ^2b to R ^5b , R ^7b , R ^12b to R ^15b , R ^17b to R ^18b , and R ^21b to R ^22b . Examples thereof include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom and a bromine atom are preferable.

M ^{b +} and MX ^{bx +} are preferably hydrons or monovalent metal ions such as Li ⁺ , Na ⁺ and K ⁺ , and preferably divalent or higher metal cations, and are hydron or divalent or higher metal cations. Is more preferred, and hydron is most preferred. It may be a divalent or higher metal cation. Examples of the divalent or higher metal cation include metal cations of groups 2 to 15 in the periodic table of elements, preferably Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , and Cd. Divalent metal cations such as ²⁺ , Ni ²⁺ , Zn ²⁺ , Cu ²⁺ , Hg ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Pb ²⁺ and Mn ²⁺ ; Al ³⁺ , Fe ³⁺ and Cr ³⁺ and other trivalent metal cations; and examples include tetravalent metal cations such as Sn ⁴⁺ , Mn ⁴⁺ and Ce ⁴⁺ , more preferably Mg ²⁺ and Ca ²⁺ . , Sr ²⁺ , Ba ²⁺ , Ni ²⁺ , Zn ²⁺ , Cu ²⁺ , Fe ²⁺ , Co ²⁺ , Sn ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ , Sn Examples include ⁴⁺ and Mn ⁴⁺ , more preferably Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Zn ²⁺ , Cu ²⁺ , Fe ²⁺ , Mn ²⁺ , Al ³⁺ , Fe. Examples include ³⁺ , Cr ³⁺ and Mn ⁴⁺ . When M ^{b +} is a hydron, the hydron binds to -CO _2- ^or -S (O) ₂ O- ^and exists as -COOH or -S (O) ₂ OH.

a and ax are preferably 1 to 10, more preferably 1 to 5, and most preferably 2 to 4.

The compound represented by the formula (I) is represented by the formula (IA) or the formula (IB).
As the compound represented by the formula (IA), those in which R ^1a to R ^9a , R ^na2 , M ^{b +} and a are as follows are preferable.
A hydrogen atom is preferable as R ^1a .
Examples of R ^2a to R ^5a include a hydrogen atom; an alkyl group having 1 to 10 carbon atoms such as a butyl group; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group; and a hydrogen atom contained in an alkyl group such as a trifluoromethyl group. _A group in which all of the atoms _are replaced with a fluorine atom ^; a halogen atom such as a chlorine atom ^and a bromine atom; a nitro group;
As R ^6a , -COO- ^, -CO-OR ^na2 , -CO-NH ₂ , -CO-NH (R ^na2 ), -CO-N (R ^na2 ) ₂ , -CO-H, -CO-R ^na2 Alternatively, -S (O) ₂ -R ^na2 is preferred, with -CO-OR ^na2 , -CO-NH ₂ , -CO-NH (R ^na2 ), -CO-N (R ^na2 ) ₂ or -CO-R ^na2 . More preferred.
Examples of R ^7a include a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, a cyano group, a nitro group, and-. CO ₂ ^- or —S (O) ₂ O ^— is preferred, and a cyano group is more preferred.
If R ^8a and R ^9a do not form a ring together with the carbon atoms to which they are bonded, then R ^8a will be -COO- ^, -CO-OR ^na2 , -CO-NH ₂ , -CO-NH ( R ^na2 ), -CO-N (R ^na2 ) ₂ , -CO-H, -CO-R ^na2 or -S (O) ₂ -R ^na2 is preferable, -CO-OR ^na2 , -CO-NH ₂ ,- CO-NH (R ^na2 ), -CO-N (R ^na2 ) ₂ or -CO-R ^na2 is more preferable, and R ^9a is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent. , A heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, a cyano group, a nitro group, —CO _2- or —S (O) _2O ^— is preferable, ^and a cyano group is more preferable. In this case, it is preferable that R ^6a and R ^8a are the same group.
When R ^8a and R ^9a form a ring together with the carbon atom to which each bond is formed, it is preferable to form a structure of group A, and it is preferable to form a ring represented by the formula (QQ18). .. In the formula (QQ18), a hydrogen atom is preferable as R ²⁵ and R ²⁶ .
It is also preferable that R ^8a and R ^9a do not form a ring.
R ^na2 is an alkyl group having 1 to 10 carbon atoms such as a methyl group, an ethyl group and a butyl group; an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group, a toluyl group and an ethylphenyl group; a benzyl group (benzyl group). A group that combines a chain hydrocarbon group such as a phenylmethyl group), a 2-methylbenzyl group, a 3-methylbenzyl group, a 4-methylbenzyl group, a phenylethyl group, and a phenylpropyl group with an aromatic hydrocarbon group. A group having 7 to 15 carbon atoms; etc. is preferable, and these groups may have −CO _2- , —S (O) _2O ⁻ ;, ^and carbon such as a methoxy group can be used as a substituent. It may have an alkoxy group having a number of 1 to 10; an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms such as a methoxycarbonyl group is bonded; a sulfamoyl group; a hydroxy group; a halogen atom such as a chlorine atom; It is preferable ^to have -CO _2- ^, -S (O) ₂ O-.
M ^{b +} includes hydron, Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Zn ²⁺ , Cu ²⁺ , Fe ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ . One selected from the group consisting of Mn 4+ and Mn ⁴⁺ is preferable, and hydron is more preferable.
As a, any integer of 1 to 5 is preferable, and 2 is even more preferable.

As the compound represented by the formula (IB), those having R ^1b to R ^7b , R ^17b to R ^20b , R ^nb1 and R ^{nb 5} are preferable.
A hydrogen atom is preferable as R ^1b .
Examples of R ^2b to R ^5b include a hydrogen atom; an alkyl group having 1 to 10 carbon atoms such as a butyl group; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group; and a hydrogen atom contained in an alkyl group such as a trifluoromethyl group. A group in which all of the above are replaced with a fluorine atom; a halogen atom such as a chlorine atom and a bromine atom; a nitro group and the like are preferable.
As R ^6b , -CO-OR ^nb1 , -CO-NH ₂ , -CO-NH (R ^nb1 ), -CO-N (R ^nb1 ) ₂ or -CO-R ^nb1 are preferable.
Examples of R ^7b include a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, a cyano group, a nitro group, and-. CO _2- ^or —S (O) ₂ O ^— is preferred, and a cyano group is more preferred.
If R ^17b and R ^18b do not form a ring together with the carbon atoms to which they are bonded, then R ^17b is -CO-OR ^nb5 , -CO-NH ₂ , -CO-NH (R ^nb5 ), -CO-N (R ^nb5 ) ₂ , -CO-H, -CO-R ^nb5 or -S (O) ₂ -R ^nb5 is preferable, -CO-OR ^nb5 , -CO-NH ₂ , -CO-NH ( R ^nb5 ), -CO-N (R ^nb5 ) ₂ or -CO-R ^nb5 is more preferable, and R ^18b includes a hydrocarbon group having 1 to 40 carbon atoms and a substituent which may have a substituent. A heterocyclic group, a hydrogen atom, a halogen atom, a cyano group or a nitro group which may be possessed is preferable, and a cyano group is more preferable. In this case, R ^6b and R ^17b are preferably the same group.
When R ^17b and R ^18b form a ring together with the carbon atom to which each bond is formed, those forming the structure of group C are preferable, and the ring represented by the formula (2a) is more preferably formed. preferable. In the formula (2a), a hydrogen atom is preferable as R ^19b and R ^20b .
It is also preferable that R ^17b and R ^18b do not form a ring.
As R ^nb1 and R ^nb5 , an alkyl group having 1 to 10 carbon atoms such as a methyl group, an ethyl group and a butyl group; an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group, a toluyl group and an ethylphenyl group; A group that is a combination of a chain hydrocarbon group such as a phenylmethyl group or a phenylethyl group and an aromatic hydrocarbon group and has 7 to 15 carbon atoms; and the like are preferable, and these groups are methoxy groups as substituents. Etc., an alkoxy group having 1 to 10 carbon atoms; an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms such as a methoxycarbonyl group is bonded; a sulfamoyl group; a hydroxy group; a halogen atom such as a chlorine atom; May be good.

The compounds represented by the formula (II) preferably have R ¹¹ to R ¹⁶ , R ²¹ to R ²² , R ^na1 , R ^na2 , MX ^{bx +} , and ax as follows.
A hydrogen atom is preferable as R ¹¹ .
Examples of R ¹² to R ¹⁵ include a hydrogen atom; an alkyl group having 1 to 10 carbon atoms such as a butyl group; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group; and a hydrogen atom contained in an alkyl group such as a trifluoromethyl group. _A group in which all of the atoms _are replaced with a fluorine atom ^; a halogen atom such as a chlorine atom ^and a bromine atom; a nitro group;
As R ¹⁶ , -CO-OR ^na1 , -CO-NH ₂ , -CO-NH (R ^na1 ), -CO-N (R ^na1 ) ₂ or -CO-R ^na1 are preferable.
If R ²¹ and R ²² do not form a ring together with the carbon atoms to which they are bonded, then R ²¹ may be -CO-OR ^na2 , -CO-NH ₂ , -CO-NH (R ^na2 ), etc. -CO-N (R ^na2 ) ₂ , -CO-H, -CO-R ^na2 or -S (O) ₂ -R ^na2 is preferable, -CO-OR ^na2 , -CO-NH ₂ , -CO-NH ( R ^na2 ), -CO-N (R ^na2 ) ₂ or -CO-R ^na2 is more preferable, and R ²² includes a hydrocarbon group having 1 to 40 carbon atoms and a substituent which may have a substituent. A heterocyclic group, a hydrogen atom, a halogen atom, a cyano group, a nitro group, —CO _2- or —S (O) _2O ^— which may be possessed is preferable, ^and a cyano group is more preferable. In this case, R ¹⁶ and R ²¹ are preferably the same group.
When R ²¹ and R ²² form a ring together with the carbon atom to which each bond is formed, it is preferable to form a structure of group B, and to form a ring represented by the formula (2a-x). Is more preferable. In the formula (2a-x), a hydrogen atom is preferable as R ²³ and R ²⁴ .
It is also preferable that R ²¹ and R ²² do not form a ring.
As R ^na1 and R ^na2 , an alkyl group having 1 to 10 carbon atoms such as a methyl group, an ethyl group and a butyl group; an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group, a toluyl group and an ethylphenyl group; A group that is a combination of a chain hydrocarbon group such as a phenylmethyl group or a phenylethyl group and an aromatic hydrocarbon group and has 7 to 15 carbon atoms; etc., and these groups are preferably −CO as a substituent. _2- ^; -S (O) ₂ ^O- ; An alkoxy group having 1 to 10 carbon atoms such as a methoxy group; an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms such as a methoxycarbonyl group is bonded; a sulfamoyl group; a hydroxy It may have a group; a halogen atom such as a chlorine atom;
MX ^{bx +} includes hydron, Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Zn ²⁺ , Cu ²⁺ , Fe ²⁺ , Mn ²⁺ , Al ³⁺ , Fe ³⁺ , Cr ³⁺ . And one selected from the group consisting of Mn ⁴⁺ is preferred.
As ax, any integer of 1 to 10 is preferable, and any integer of 1 to 5 is more preferable.

As the compound represented by the formula (IIB), those having R ^11b to R ^16b , R ^21b to R ^24b , R ^nb1 and R ^{nb 5} are preferable.
A hydrogen atom is preferable as R ^11b .
Examples of R ^12b to R ^15b include a hydrogen atom; an alkyl group having 1 to 10 carbon atoms such as a butyl group; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group; and a hydrogen atom contained in an alkyl group such as a trifluoromethyl group. A group in which all of the above are replaced with a fluorine atom; a halogen atom such as a chlorine atom and a bromine atom; a nitro group and the like are preferable.
As R ^16b , -CO-OR ^nb1 , -CO-NH ₂ , -CO-NH (R ^nb1 ), -CO-N (R ^nb1 ) ₂ or -CO-R ^nb1 are preferable.
When R ^21b and R ^22b do not form a ring together with the carbon atoms to which they are bonded, the R ^21b is -CO-OR ^nb5 , -CO-NH ₂ , -CO-NH (R ^nb5 ), and so on. -CO-N (R ^nb5 ) ₂ , -CO-H, -CO-R ^nb5 or -S (O) ₂ -R ^nb5 is preferable, -CO-OR ^nb5 , -CO-NH ₂ , -CO-NH ( R ^nb5 ), -CO-N (R ^nb5 ) ₂ or -CO-R ^nb5 is more preferable, and R ^22b includes a hydrocarbon group having 1 to 40 carbon atoms and a substituent which may have a substituent. A heterocyclic group, a hydrogen atom, a halogen atom, a cyano group or a nitro group which may be possessed is preferable, and a cyano group is more preferable. In this case, it is preferable that R ^16b and R ^21b are the same group.
When R ^21b and R ^22b form a ring together with carbon atoms to which they are bonded, it is preferable to form a structure of group C, and to form a ring represented by the formula (2a-xb). Is more preferable. In the formula (2a-xb), a hydrogen atom is preferable as R ^23b and R ^24b .
It is also preferable that R ^21b and R ^22b do not form a ring.
As R ^nb1 and R ^nb5 , an alkyl group having 1 to 10 carbon atoms such as a methyl group, an ethyl group and a butyl group; an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group, a toluyl group and an ethylphenyl group; A group that is a combination of a chain hydrocarbon group such as a phenylmethyl group or a phenylethyl group and an aromatic hydrocarbon group and has 7 to 15 carbon atoms; and the like are preferable, and these groups are methoxy groups as substituents. Etc., an alkoxy group having 1 to 10 carbon atoms; an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms such as a methoxycarbonyl group is bonded; a sulfamoyl group; a hydroxy group; a halogen atom such as a chlorine atom; May be good.

As -CO-OR ^na1 , -CO-OR ^na2 , -CO-OR ^nb1 , and -CO-OR ^nb5 , hydrocarbon groups having 1 to 10 carbon atoms (particularly, alkyl groups such as methoxycarbonyl group and ethoxycarbonyl group) have 1 to 10 carbon atoms. An oxycarbonyl group to which an alkyl group) is bonded is preferable.

-CO-R ^na1 , -CO-R ^na2 , -CO-R ^nb1 , and -CO-R ^nb5 are carbonyl groups to which an aromatic ring having 6 to 10 carbon atoms such as a benzoyl group is bonded; ethylcarbonyl group, butyl. A carbonyl group to which an alkyl group having 1 to 10 carbon atoms such as a carbonyl group is bonded; an alkyl group having 1 to 10 carbon atoms to which an aromatic ring having 1 to 10 carbon atoms such as a phenylmethyl group and a phenylethyl group is bonded is bonded. A carbonyl group is preferred. Further, R ^na1 and R ^na2 of -CO-R ^na1 and -CO-R ^na2 are, as substituents, -CO _2- ^; -S (O) ₂ ^O- ; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group. It may have an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms such as a methoxycarbonyl group is bonded; a sulfamoyl group; a hydroxy group; a halogen atom such as a chlorine atom; and the aromatic ring is bonded. _{A carbonyl} group ^; a carbonyl group ^to which an alkyl group is bonded; a carbon atom such as a carbonyl group to which an alkyl group to which an aromatic ring is bonded; An alkoxy group having a number of 1 to 10; an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms such as a methoxycarbonyl group is bonded; a sulfamoyl group; a hydroxy group; a halogen atom such as a chlorine atom; and the like may be bonded. ..
-CO-NH (R ^na1 ), -CO-NH (R ^na2 ), -CO-NH (R ^nb1 ), and -CO-NH (R ^nb5 ) have 1 to 10 carbon atoms such as a methylaminocarbonyl group. An aminocarbonyl group to which an alkyl group is bonded is preferable. Further, —CO ₂ ^- may be bonded to a carbon atom such as an aminocarbonyl group to which the alkyl group is bonded or an aminocarbonyl group to which an aromatic hydrocarbon ring is bonded.
-CO-N (R ^na1 ) ₂ , -CO-N (R ^na2 ) ₂ , -CO-N (R ^nb1 ) ₂ , -CO-N (R ^nb5 ) ₂ have carbon atoms such as a dimethylaminocarbonyl group. An aminocarbonyl group in which two alkyl groups 1 to 10 are bonded is preferable.

The compound represented by the formula (I) is represented by the formula (P).

[In the formula, L ^1p and L ^2p represent a hydrocarbon group having 1 to 10 carbon atoms independently of each other, and -CH _2- contained in the hydrocarbon group may be replaced with -NH-. R ^p represents a hydrogen atom or a substituent, and p represents an integer of 1 to 4. ]

Specific examples of the compound represented by the formula (I), (IA), (IB), (II) or the formula (IIB) include, for example, R ³¹ , L ¹ in the compound represented by the formula (Ia). , L ² , R ³² , B ¹ B ² , n, m and M ^{b +} in any of Tables 1 to 4, and in the compounds represented by the formula (Ib), R ³³ , L. Examples thereof include compounds in which the combination of ³ , B ¹ B ² , n, m and M ^{b +} is any one of Tables 5 to 6. In addition, R ³¹ , R ³² , and R ³³ represent any partial structure represented by the formula (HH1) to the formula (HH18). B ¹ B ² represents any partial structure represented by the equations (BB1) to (BB9).

（式中、波線は、Ｅ体及びＺ体の両方を含むことを示す）

(In the equation, the wavy line indicates that it contains both E-form and Z-form)

Among the compounds shown in the table, compound numbers 28 to 31, 37 to 40, 46 to 49, 73 to 76, 82 to 85, 91 to 94, 136 to 139, 154 to 157, 190 to 193, 199 to 202, Compounds 208 to 211, 244 to 247, 298 to 301 are preferred.

In the compound represented by the formula (I) (hereinafter, also referred to as compound (I)), the compound in which R ¹ is a hydrogen atom (hereinafter, also referred to as compound (IH)) is represented by the formula (pt1). After reacting a compound (hereinafter, may be referred to as a phthalonitrile compound) with a compound represented by the formula (pt2) (hereinafter, may be referred to as an alkoxide compound), the compound represented by the formula (pt3) (hereinafter, may be referred to as an alkoxide compound). It can be produced by further reacting with a compound (sometimes referred to as pt3) and a compound represented by the formula (pt4) (hereinafter, sometimes referred to as a compound (pt4)) in the presence of an acid.

[In the formulas (pt1) to (pt8), formulas (IH), formulas (IM), and formulas (IR), ^R1 to ^R7 , X, M ^{b +} , a, m, and n represents the same meaning as described above. R ⁴¹ and R ⁴² independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. M ¹ and M ² represent alkali metal atoms independently of each other. LG ¹ and LG ² represent a halogen atom, a methanesulfonyloxy group, a chloromethylsulfonyloxy group, a toluenesulfonyloxy group or a trifluoromethanesulfonyloxy group. ]

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ⁴¹ and R ⁴² include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group. However, an alkyl group having 1 to 6 carbon atoms is preferable.
Examples of the alkali metal atom represented by M ¹ and M ² include a lithium atom, a sodium atom and a potassium atom.

The amount of the alkoxide compound represented by the formula (pt2) to be used is usually 0.1 to 10 mol, preferably 0.2 to 5 mol, with respect to 1 mol of the phthalonitrile compound represented by the formula (pt1). It is mol, more preferably 0.3 to 3 mol, still more preferably 0.4 to 2 mol.

The total amount of the compound (pt3) and the compound (pt4) used is usually 2 to 20 mol, preferably 2 to 10 mol, based on 1 mol of the phthalonitrile compound represented by the formula (pt1). , More preferably 2 to 6 mol, still more preferably 2 to 4 mol. The compound (pt3) and the compound (pt4) may be the same.

Examples of the acid include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, nitric acid, fluorosulfonic acid and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid and p-toluenesulfonic acid; acetic acid. , Citrate, formic acid, gluconic acid, lactic acid, oxalic acid and tartrate acid and the like, preferably hydrogen chloride, hydrogen bromide, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid and carboxylic. Acids are mentioned, more preferably acetic acid.
The amount of the acid used is usually 1 to 20 mol, preferably 1 to 10 mol, more preferably 1 to 8 mol, still more preferably 1 to 6 mol, relative to 1 mol of the phthalonitrile compound. be.

The reaction of the phthalonitrile compound, the alkoxide compound, the compound (pt3) and the compound (pt4) is usually carried out in the presence of a solvent. As the solvent, water; a nitrile solvent such as acetonitrile; an alcohol solvent such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; an ether solvent such as tetrahydrofuran; a ketone solvent such as acetone; acetic acid. Ester solvents such as ethyl; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride and chloroform; amides such as N, N-dimethylformaldehyde and N-methylpyrrolidone. Solvents; examples include sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents. More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, methylene chloride, chloroform, N, N-dimethylformaldehyde. , N-dimethylacetaldehyde, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone and dimethylsulfoxide. More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, methylene chloride, chloroform, N, N-dimethylformaldehyde, N-dimethylacetaldehyde, 1 , 3-Dimethyl-2-imidazolidinone and 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone N-methylpyrrolidone and dimethylsulfoxide, with particular preference being water, acetonitrile. , Methanol, ethanol, 2-propanol, N-methylpyrrolidone and dimethylsulfoxide. The amount of the solvent used is usually 1 to 1000 parts by mass with respect to 1 part by mass of the phthalonitrile compound.

The reaction temperature of the phthalonitrile compound, the alkoxide compound, the compound (pt3) and the compound (pt4) is usually 0 to 200 ° C., preferably 0 to 100 ° C., and more preferably 0 to 50 ° C. The reaction time is usually 0.5 to 300 hours.

The amount of the compound represented by the formula (pt6) (hereinafter, may be referred to as compound (pt6)) is usually 1 to 10 mol, preferably 1 to 1 to 1 mol of the compound (IH). It is 5 mol, more preferably 1 to 3 mol, still more preferably 1 to 2 mol.

Further, when the compound (pt6) is reacted, it is preferable that a base coexists. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, pyridine and piperidine, metal alkoxides such as sodium methoxydo, sodium ethoxydo, sodium tert-butoxide and potassium tert-butoxide, and butyl lithium. , Tart-organic metal compounds such as butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.

The amount of the base used is usually 1 to 10 mol, preferably 1 to 5 mol, more preferably 1 to 3 mol, still more preferably 1 to 2 mol, relative to 1 mol of compound (IH). It is a mole.

The reaction of compound (pt6) is usually carried out in the presence of a solvent. The solvent can be selected from the same range as described above.

The amount of the solvent used is usually 1 to 1000 parts by mass with respect to 1 part by mass of the compound (hereinafter, also referred to as compound (IR)) in which R ¹ is not a hydrogen atom in the compound (I). The reaction temperature of the compound (pt6) is usually −90 to 200 ° C., preferably −80 to 100 ° C., and more preferably 0 to 50 ° C. The reaction time is usually 0.5 to 300 hours.

When the compound (IR) does not have a sulfo group, the sulfo group can be introduced by reacting the compound (IR) with a sulphonizing agent such as fuming sulfuric acid or chlorosulfonic acid.

The amount of SO ₃ used in fuming sulfuric acid is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and further, relative to 1 mol of compound (IR). It is preferably 5 to 25 mol. The amount of sulfuric acid used in the fuming sulfuric acid is usually 1 to 200 mol, preferably 10 to 100 mol, more preferably 10 to 75 mol, still more preferably, relative to 1 mol of compound (IR). Is 10 to 50 mol.

The amount of chlorosulfonic acid used is usually 1 to 500 mol, preferably 10 to 300 mol, more preferably 10 to 200 mol, still more preferably 10 per 1 mol of compound (IR). ~ 150 mol.

The reaction temperature for sulfonation is usually −20 to 200 ° C., preferably −10 to 100 ° C., and more preferably 0 to 50 ° C. The reaction time is usually 0.5 to 300 hours.

When the compound (IR) has a carboxy group or a sulfo group, the compound represented by the formula (pt7) is reacted with the compound represented by the formula (pt8), and the compound (I) containing the metal M ^{b +} is reacted. ) (Hereinafter, also referred to as compound (IM)) may be produced.

The method for extracting compound (I) from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after completion of the reaction, compound (I) can be taken out by filtering the reaction mixture. Further, after filtering, the obtained residue may be washed with a solvent. Further, after filtration, column chromatography, recrystallization or sublimation purification may be performed.

In the colored curable resin composition of the present invention, the content of the compound (I) is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, still more preferably, based on 100% by mass of the total solid content. Is 0.3% by mass or more, more preferably 1% by mass or more, particularly preferably 2% by mass or more, preferably 80% by mass or less, more preferably 70% by mass or less, still more preferably 60% by mass or less. Even more preferably, it is 50% by mass or less, and particularly preferably 30% by mass or less.
Further, the content of the compound (I) is preferably 0.1% by mass or more, more preferably 1% by mass or more, still more preferably 3% by mass or more, still more, in the total amount of the colorant (A) of 100% by mass. It is preferably 5% by mass or more, particularly preferably 10% by mass or more, preferably 90% by mass or less, more preferably 80% by mass or less, still more preferably 70% by mass or less, and even more preferably 60% by mass or less. ..
As used herein, the term "total amount of solids" refers to the total amount of the components of the coloring composition or the coloring curable resin composition of the present invention excluding the solvent (E). The total amount of solid content and the content of each component relative to the total amount can be measured by a known analytical means such as liquid chromatography or gas chromatography.

As the red pigment contained in the color curable resin composition of the present invention, known pigments can be used, and for example, among the pigments classified as pigments in the Color Index (The Society of Dyers and Colorists). , Those classified as red. Two or more types may be combined.

Specifically, C.I. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 208, 209, 215, 216, 224, 242, 254, 255, 264, 265, Examples thereof include red pigments such as 266, 268, 269, and 273.

Among the red pigments, anthraquinone pigments, azo pigments, quinacridone pigments, perylene pigments, and diketopyrrolopyrrole pigments are preferable, and C.I. I. Pigment Red 177, 208, 242, 254, 269, and the red pigment (A-1) obtained in Synthetic Example 6 described later are preferable. I. Pigment Red 177, 254 and the red pigment (A-1) are more preferred.

The red pigment preferably has absorption in a wavelength range of 580 nm or less, and more preferably has absorption in a wavelength range of 480 nm or more and 560 nm or less. Further, the red pigment preferably transmits light in a wavelength range of 610 nm or more.

The content of the red pigment is preferably 10 parts by mass or more, more preferably 25 parts by mass or more, still more preferably 40 parts by mass or more, and even more preferably 70 parts by mass or more with respect to 100 parts by mass of the compound (I). Especially preferably 90 parts by mass or more, preferably 99900 parts by mass or less, more preferably 9900 parts by mass or less, still more preferably 3300 parts by mass or less, still more preferably 1500 parts by mass or less, and particularly preferably 500 parts by mass or less. Is.
Further, the total content of the compound (I) and the red pigment is preferably 30% by mass or more, more preferably 40% by mass or more, still more preferably 50% by mass or more, still more, in the total amount of the colorant of 100% by mass. It is preferably 80% by mass or more, particularly preferably 90% by mass or more, and preferably 100% by mass or less.

The color-curable resin composition of the present invention may contain a colorant other than the compound (I) and the red pigment (hereinafter, may be referred to as a colorant (A1)) as the colorant (A). The colorant (A1) may contain one kind or two or more kinds of colorants.

The colorant (A1) may be a dye or a pigment. Examples of the dye include known dyes described in the Color Index (published by The Society of Dyers and Colorists) and Dyeing Note (Dyeing Co., Ltd.). According to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridin dyes, styryl dyes, coumarin dyes, quinoline. Examples thereof include dyes, nitro dyes and phthalocyanine dyes. Of these, organic solvent-soluble dyes are preferable. Two or more of these dyes may be used in combination.

Specific examples thereof include dyes having the following color index (CI) numbers. C. I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Reactive Yellow 2,76,116;
C. I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C. I. Disperse Yellow 51, 54, 76;
C. I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C. I. Reactive orange 16;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
C. I. Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;
C. I. Acid Violet 34, 102;
C. I. Disperse Violet 26, 27;
C. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. Acid Blue 25, 27, 40, 45, 78, 80, 112;
C. I. Direct blue 40;
C. I. Disperse Blue 1, 14, 56, 60;
C. I. Solvent Green 1, 3, 5, 28, 29, 32, 33;
C. I. Acid Green 3, 5, 9, 25, 27, 28, 41;
C. I. Basic green 1;
C. I. Bat green 1st prize.

As the pigment, known pigments can be used, and examples thereof include pigments classified as pigments in the Color Index (The Society of Dyers and Colorists Publishing). Two or more types may be combined.
Specifically, C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet color pigments;
C. I. Pigment Green 7, 36, 58, 59 green pigments can be mentioned.

As the colorant (A1), a yellow dye and a yellow pigment (hereinafter, these may be collectively referred to as "yellow colorant") are preferable.

Examples of the yellow dye include dyes whose hue is classified as yellow among the above dyes, and examples of yellow pigments include pigments whose hue is classified as yellow among the above pigments.

The amount of the colorant (A1) is 0 parts by mass or more and 95 parts by mass or less, preferably 90 parts by mass or less, more preferably 80 parts by mass or less, and even more preferably 50 parts by mass with respect to 100 parts by mass of the compound (I). The amount is 20 parts or less, more preferably 20 parts by mass or less, and particularly preferably 10 parts by mass or less.

The colorant (A) is, if necessary, treated with a rosin, a surface treatment using a colorant derivative having an acidic group or a basic group introduced therein, and a graft treatment on the surface of the colorant (A) with a polymer compound or the like. , Sulfuric acid atomization treatment or the like, cleaning treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method or the like may be performed. The particle size of the colorant (A) is preferably substantially uniform. The colorant (A) can be uniformly dispersed in the dispersion liquid by containing the dispersant and performing the dispersion treatment.

Examples of the dispersant include a surfactant and the like, and any of a cationic, anionic, nonionic and amphoteric surfactants may be used. Specific examples thereof include polyester-based, polyamine-based and acrylic-based surfactants. These dispersants may be used alone or in combination of two or more. Dispersants include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), and EFKA (registered trademark). (BASF), Azisper (registered trademark) (Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (Big Chemie), BYK (registered trademark) (Big Chemie) and the like.

When a dispersant is used, the amount of the dispersant used is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less, based on 100 parts by mass of the colorant (A). When the amount of the dispersant used is in the above range, a liquid containing the colorant (A) in a more uniform dispersed state tends to be obtained.

The content of the colorant (A) in the color-curable resin composition is usually 1% by mass or more and 90% by mass or less, preferably 1% by mass or more and 80% by mass or less, based on the total amount of solid content. It is preferably 5% by mass or more and 75% by mass or less.

<Resin (B)>
The resin (B) is preferably an alkali-soluble resin, and is at least one monomer (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter, "monomer (a)". ) ”), It is preferable that the polymer has a structural unit derived from).
The resin (B) is a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, may be referred to as “monomer (b)”). , And other structural units are preferred.
The other structural unit is the monomer (c) copolymerizable with the monomer (a) (however, it is different from the monomer (a) and the monomer (b). Examples thereof include structural units derived from c) ”, structural units having an ethylenically unsaturated bond, and the like.

Examples of the monomer (a) include acrylic acid, methacrylic acid, crotonic acid and unsaturated monocarboxylic acids such as o-, m- and p-vinylbenzoic acid;
Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, Bicyclounsaturated compounds containing carboxy groups such as 5-carboxymethylbicyclo [2.2.1] hept-2-ene and 5-carboxyethylbicyclo [2.2.1] hept-2-ene;
Carboxylic acid anhydrides such as the above unsaturated dicarboxylic acid anhydrides excluding fumaric acid and mesaconic acid;
Unsaturated mono [(meth) acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as monosuccinic acid mono [2- (meth) acryloyloxyethyl] and mono [2- (meth) acryloyloxyethyl] phthalates. Kind;
Examples thereof include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α- (hydroxymethyl) acrylic acid.
Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and the solubility of the obtained resin in an alkaline aqueous solution.

The monomer (b) is a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxylan ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. To say. The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
Examples of the monomer (b) include a monomer (b1) having an oxylanyl group and an ethylenically unsaturated bond (hereinafter, may be referred to as “monomer (b1)”), an oxetanyl group and an ethylenically unsaturated bond. Monomer (b2) having a saturated bond (hereinafter sometimes referred to as "monomer (b2)") and monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter "monomer") (Sometimes referred to as "body (b3)").

The monomer (b1) is, for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter, “monomer (b1-)”. 1) ”) and a monomer (b1-2) having an epoxidized structure of an alicyclic unsaturated hydrocarbon (hereinafter sometimes referred to as“ monomer (b1-2) ”) Can be mentioned.

As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable. Specific examples of the monomer (b1-1) include glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethylglycidyl (meth) acrylate, glycidyl vinyl ether, vinylbenzyl glycidyl ether, and α-. Methylvinylbenzyl glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene, 2,4-bis (glycidyloxymethyl) styrene, 2,5-bis (glycidyloxymethyl) styrene, 2,6-bis (glycidyloxy) Methyl) styrene, 2,3,4-tris (glycidyloxymethyl) styrene, 2,3,5-tris (glycidyloxymethyl) styrene, 2,3,6-tris (glycidyloxymethyl) styrene, 3,4 Examples thereof include 5-tris (glycidyloxymethyl) styrene and 2,4,6-tris (glycidyloxymethyl) styrene.

Examples of the monomer (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, seroxide (registered trademark) 2000; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexylmethyl. (Meta) acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Dycel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer (registered trademark) M100; manufactured by Dycel Co., Ltd.) , The compound represented by the formula (BI), the compound represented by the formula (BII), and the like.

[In the formula (BI) and the formula (BII ^{), Ra and R b represent} a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with a hydroxy group. You may.
X ^a and X ^b independently represent a single bond, * -R ^{c-, * -R c-O-, * -R c-S- or * -R c - NH- .}
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ]

Examples of the compound represented by the formula (BI) include compounds represented by any of the formulas (BI-1) to (BI-15). Among them, the formula (BI-1), the formula (BI-3), the formula (BI-5), the formula (BI-7), the formula (BI-9) and the formula (BI-11) to the formula (BI-15). The compound represented by the formula (BI-1), the formula (BI-7), the formula (BI-9) and the compound represented by the formula (BI-15) are more preferable.

Examples of the compound represented by the formula (BII) include compounds represented by any of the formulas (BII-1) to (BII-15), and among them, the formula (BII-1) and the formula are preferable. (BII-3), formula (BII-5), formula (BII-7), formula (BII-9) and compounds represented by formulas (BII-11) to formula (BII-15) can be mentioned. Preferred examples thereof include compounds represented by the formula (BII-1), the formula (BII-7), the formula (BII-9) and the formula (BII-15).

The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone or in combination with the compound represented by the formula (BI) and the compound represented by the formula (BII). You may. When these are used in combination, the content ratios of the compound represented by the formula (BI) and the compound represented by the formula (BII) are based on a molar basis, preferably 5:95 to 95: 5, and more preferably 10: It is 90 to 90:10, more preferably 20:80 to 80:20.

Examples of the monomer (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, and 2-ethylhexyl. (Meta) acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decane-8-yl (meth) Acrylic, tricyclo [5.2.1.0 ^2,6 ] decane-9-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decene-8-yl (meth) acrylate, tricyclo [ 5.2.1.0 ^2,6 ] Decene-9-yl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, (Meta) acrylic acid esters such as propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate and benzyl (meth) acrylate;
Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconic acid;
Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2'-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5,6-dihydroxybicyclo [2.2] .1] Hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] Hept-2-ene, 5,6-di (2'-hydroxyethyl) bicyclo [2.2. 1] Hept-2-ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy -5-Methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2] .2.1] Hept-2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept-2-ene, 5-Phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5,6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept-2-ene and 5,6-bis (cyclohexyl) Oxycarbonyl) Bicyclo unsaturated compounds such as bicyclo [2.2.1] hept-2-ene;
N-Phenylmaleimide, N-Cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate and N- (9-acridinyl) maleimide;
Vinyl group-containing aromatic compounds such as styrene, α-methylstyrene, vinyltoluene and p-methoxystyrene; vinyl group-containing nitriles such as (meth) acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; (meth) acrylamide. Vinyl group-containing amides such as; esters such as vinyl acetate; diene such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene; and the like.
Of these, from the viewpoint of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo [5.2.1.0 ^2,6 ] decane-8-yl (meth) acrylate, tricyclo [5.2.1. .0 ^2,6 ] Decane-9-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] Decene-8-yl (meth) acrylate, tricyclo [5.2.1.0 ^{2, 6} ] Decene-9-yl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene, benzyl (meth) acrylate and the like are preferable.

The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth) acryloyl group. A resin having such a structural unit is a polymer having a structural unit derived from the monomer (a) or the monomer (b), and a group having the monomer (a) or the monomer (b). It can be obtained by adding a monomer having a group capable of reacting with and an ethylenically unsaturated bond.
Such structural units include a structural unit in which glycidyl (meth) acrylate is added to a (meth) acrylic acid unit, a structural unit in which 2-hydroxyethyl (meth) acrylate is added to a maleic anhydride unit, and glycidyl (meth). ) A structural unit in which (meth) acrylic acid is added to an acrylate unit can be mentioned. When these structural units have a hydroxy group, a structural unit to which a carboxylic acid anhydride is further added can also be mentioned as a structural unit having an ethylenically unsaturated bond.

The polymer having a structural unit derived from the monomer (a) can be produced, for example, by polymerizing the monomer constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator, solvent and the like are not particularly limited, and those usually used in the art can be used. For example, as the polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) As the solvent, any solvent may be used as long as it dissolves each monomer, and the above-mentioned solvent (E) and the like can be mentioned.

As the obtained polymer, the solution after the reaction may be used as it is, a concentrated or diluted solution may be used, or the polymer is taken out as a solid (powder) by a method such as reprecipitation. May be used.
If necessary, a reaction catalyst of a carboxylic acid or carboxylic acid anhydride and a cyclic ether (for example, tris (dimethylaminomethyl) phenol, etc.), a polymerization inhibitor (for example, hydroquinone, etc.) and the like may be used.
Examples of the carboxylic acid anhydride include maleic anhydride, citraconic acid anhydride, itaconic acid anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 , 2,3,6-Tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride and 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride and the like.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer and 3,4-epoxytricyclo [5.2.1.0 ^2,6 . ] Decyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth)
Acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^{2 , 6} ] Decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) ) Acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / tricyclo [5.2.1.0 ^2,6 ] decenyl ( Meta) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3- (meth) acrylic loyloxymethyloxetane / (meth) acrylic acid / styrene copolymer, benzyl (meth) acrylate / (Meta) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer, and the resins described in JP-A-9-106071, JP-A-2004-29518 and JP-A-2004-361455. Can be mentioned.
Among them, as the resin (B), a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b) is preferable.
The resin (B) may be a combination of two or more, in which case the resin (B) is at least 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate. / (Meta) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (Meta) Acrylate Copolymer, 3,4-Epoxytricyclo [5.2.1.0 ^2,6 ] Decyl (meth) Acrylate / (Meta) Acrylic Acid / Vinyl Toluene Copolymer, 3,4-Epoxy It is preferable to contain 1 or more selected from the tricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / (meth) acrylate / 2-ethylhexyl (meth) acrylate copolymer.

The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. .. The dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.

The solid acid value of the resin (B) is preferably 20 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and even more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution.

The content of the resin (B) in the color-curable resin composition is, for example, 1 to 700 parts by mass, preferably 5 to 500 parts by mass, more preferably 100 parts by mass with respect to 100 parts by mass of the compound (I). Is 10 to 400 parts by mass.
Further, the content of the resin (B) in the colored curable resin composition is preferably 7 to 99% by mass, more preferably 13 to 99% by mass, and further preferably 13 to 99% by mass with respect to the total amount of solid content. It is 15 to 95% by mass.

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenically unsaturated bond, and is preferable. It is a (meth) acrylic acid ester compound.

Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. Etc., as well as the above-mentioned monomers (a), monomer (b) and monomer (c).

Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol di. Examples thereof include (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.

Above all, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylol propantri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (dipentaerythritol hexa (). Meta) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl ) Isocyanurate, ethylene glycol-modified pentaerythritol tetra (meth) acrylate, ethylene glycol-modified dipentaerythritol hexa (meth) acrylate, propylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, Examples thereof include caprolactone-modified pentaerythritol tetra (meth) acrylate and caprolactone-modified dipentaerythritol hexa (meth) acrylate, preferably dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

The content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 10 to 60% by mass, and further preferably 10 to 60% by mass with respect to the total amount of solids in the colored curable resin composition. It is preferably 13 to 55% by mass.

<Polymer Initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids and the like by the action of light or heat, and a known polymerization initiator can be used. Examples of the polymerization initiator (D) include an O-acyloxime compound, an alkylphenone compound, a biimidazole compound, a triazine compound, an acylphosphine oxide compound and the like.

等の市販品を用いてもよい。中でも、Ｏ－アシルオキシム化合物としては、Ｎ－ベンゾイルオキシ－１－（４－フェニルスルファニルフェニル）ブタン－１－オン－２－イミン、Ｎ－ベンゾイルオキシ－１－（４－フェニルスルファニルフェニル）オクタン－１－オン－２－イミン及びＮ－ベンゾイルオキシ－１－（４－フェニルスルファニルフェニル）－３－シクロペンチルプロパン－１－オン－２－イミン、Ｎ－アセトキシ－１－（４－フェニルスルファニルフェニル）－３－シクロペンチルプロパン－１－オン－２－イミン、Ｎ－アセトキシ－１－（４－フェニルスルファニルフェニル）－３－シクロヘキシルプロパン－１－オン－２－イミンからなる群から選ばれる少なくとも１種が好ましく、Ｎ－ベンゾイルオキシ－１－（４－フェニルスルファニルフェニル）オクタン－１－オン－２－イミン、Ｎ－アセトキシ－１－（４－フェニルスルファニルフェニル）－３－シクロヘキシルプロパン－１－オン－２－イミンがより好ましい。 Examples of the O-acyloxym compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-. 1-on-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-on-2-imine, N-acetoxy-1- [9-ethyl-6- (9-ethyl-6- ( 2-Methylbenzoyl) -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,4) -Dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole- 3-Il] -3-cyclopentylpropane-1-imine and N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl] -3-cyclopentylpropane-1 -On-2-Imin and the like. Further, as the O-acyloxime compound, Irgacure OXE01, OXE02 (above, manufactured by BASF) and N-1919 (manufactured by ADEKA), a compound represented by the following formula (d).

And other commercially available products may be used. Among them, the O-acyloxym compounds include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-. 1-on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-on-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl)- At least one selected from the group consisting of 3-cyclopentylpropane-1-on-2-imine and N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-1-on-2-imine is preferable. , N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-on-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-1-on-2- Imin is more preferred.

Examples of the alkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-. On and 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butane-1-one, 2-hydroxy-2-methyl-1-phenyl Propane-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] Propane-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1- Examples thereof include (4-isopropenylphenyl) propan-1-one oligomers, α, α-diethoxyacetophenone, benzyldimethylketal and the like. As the alkylphenone compound, a commercially available product such as Irgacure 369, 907, 379 (all manufactured by BASF) may be used.

Examples of the biimidazole compound include 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2,3-dichlorophenyl) -4. , 4', 5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372, JP-A-6-75373, etc.), 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (alkoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (dialkoxyphenyl) biimidazole, 2,2' -Bis (2-chlorophenyl) -4,4', 5,5'-tetra (trialkoxyphenyl) biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, etc.) and 4 , 4', 5,5'-position phenyl group is substituted with a carboalkoxy group, and examples thereof include a biimidazole compound (see, for example, JP-A-7-10913).

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl). -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl)- 1,3,5-Triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis ( Trichloromethyl) -6- [2- (fran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methyl) Phenyl) ethenyl] -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine and the like can be mentioned. ..

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.

Further, as the polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and benzoin isobutyl ether; benzophenone, o-methyl benzoyl benzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone and 2,4,6-trimethylbenzophenone; 9,10-phenanthlenquinone, Kinon compounds such as 2-ethylanthraquinone and camphorquinone; examples thereof include 10-butyl-2-chloroacrydone, benzyl, methyl phenylglycoxylate and titanosen compounds. These are preferably used in combination with the polymerization initiation aid (D1) (particularly amines) described later.

The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound, and more preferably. A polymerization initiator containing an O-acyloxime compound.

The content of the polymerization initiator (D) is preferably 0.001 to 40% by mass, more preferably 0.01 to 30% by mass, based on the total amount of solids in the colored curable resin composition.

The colored curable resin composition of the present invention may further contain a polymerization initiation aid (D1), a leveling agent (F), and the like.

<Polymerization initiation aid (D1)>
The polymerization initiator (D1) is a compound or a sensitizer used to promote the polymerization of the polymerizable compound (C) whose polymerization has been started by the polymerization initiator. When the polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4-. 2-Ethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4'-bis (diethylamino) benzophenone and 4,4'-bis ( Ethylmethylamino) benzophenone and the like, preferably 4,4'-bis (diethylamino) benzophenone and the like. Further, as the amine compound, a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-dibutoxy. Examples thereof include anthracene and 2-ethyl-9,10-dibutoxyanthracene.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and the like.

Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, and N. -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like can be mentioned.

When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.001 to 30% by mass, more preferably 0.01 to 0.01% of the total solid content of the colored curable resin composition. It is 20% by mass.

<Solvent (E)>
Examples of the solvent (E) include an ester solvent (solvent containing -COO- in the molecule and not containing -O-) and an ether solvent (solvent containing -O- in the molecule and not containing -COO-). , Ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule but not -COO-), alcohol solvent (OH in the molecule) Included, -O-, -CO- and -COO-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide and the like.

Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate. , Methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, γ-butyrolactone and the like.

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether. , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl Examples thereof include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenyletol, methyl anisol and the like.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy. Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl Examples thereof include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. And so on.

Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin and the like.
Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene and the like.
Examples of the amide solvent include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.
Two or more of these solvents may be used in combination.
The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 90% by mass, based on the total amount of the colored curable resin composition.

When the colorant (A) is dispersed in the solvent (E) to prepare a color dispersion liquid, a part or all, preferably a part of the resin (B) contained in the color curable resin composition is previously contained. You may. By including the resin (B) in advance, the dispersion stability of the colored composition can be further improved.

<Leveling agent (F)>
Examples of the leveling agent (F) include a silicone-based surfactant, a fluorine-based surfactant, and a silicone-based surfactant having a fluorine atom. These may have a polymerizable group in the side chain.
Examples of the silicone-based surfactant include a surfactant having a siloxane bond in the molecule. Specifically, Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, Examples thereof include KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan GK).

Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafuck (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F554. R30, RS-718-K (manufactured by DIC Co., Ltd.), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.).

Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megafuck (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Corporation).

The content of the leveling agent (F) is preferably 0.001% by mass or more and 0.2% by mass or less, and preferably 0.002% by mass or more and 0.1 with respect to the total amount of the colored curable resin composition. It is by mass or less, more preferably 0.007% by mass or more and 0.07% by mass or less, and most preferably 0.007% by mass or more and 0.05% by mass or less. The content of the pigment dispersant is not included in this content. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Other ingredients>
The colored curable resin composition of the present invention is an additive known in the art such as a filler, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and the like, if necessary. May include.

<Manufacturing method of colored curable resin composition>
The color-curable resin composition of the present invention includes, for example, a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E) used as necessary. It can be prepared by mixing a leveling agent (F), a polymerization initiator (D1) and other components.
The compound (I), the red pigment, and the pigment as the colorant (A1) used as necessary are mixed in advance with a part or all of the solvent (E), and the average particle size of the pigment is about 0.2 μm or less. It is preferable to disperse using a bead mill or the like until the above results are obtained. At this time, if necessary, a part or all of the pigment dispersant and the resin (B) may be blended. A color-curable resin composition can be prepared by mixing the remaining components with the pigment dispersion liquid thus obtained so as to have a predetermined concentration.

In particular, after preparing a compound (I) -containing liquid containing the compound (I) and the solvent (E) in advance and a red pigment-containing liquid containing the red pigment and the solvent (E), the compound (I) -containing liquid and the liquid The colored curable resin composition may be prepared using the red pigment-containing liquid. The compound (I) -containing liquid or the red pigment-containing liquid can be prepared by dispersing the compound (I) or the red pigment in the solvent (E) and mixing them. The compound (I) -containing liquid or the red pigment-containing liquid may contain a part or all of the solvent (E) contained in the colored curable resin composition.
It is preferable to filter the colored curable resin composition after mixing with a filter having a pore size of about 0.1 to 10 μm.

<Manufacturing method of color filter>
Examples of the method for producing a colored pattern from the colored curable resin composition of the present invention include a photolithography method, an inkjet method, a printing method and the like. Of these, the photolithography method is preferable. The photolithography method is a method in which the colored curable resin composition is applied to a substrate and dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the photolithography method, a colored coating film which is a cured product of the colored composition layer can be formed by not using a photomask at the time of exposure and / or not developing the photomask. The colored pattern or colored coating film thus formed can be used as the color filter of the present invention.
The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose, application and the like. For example, 0.1 to 30 μm, preferably 0.1 to 20 μm, still more preferably 0.5. It is ~ 6 μm.

The substrate includes a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is silica-coated, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or on the substrate. Aluminum, silver, silver / copper / palladium alloy thin films, etc. are formed on the glass. Another color filter layer, resin layer, transistor, circuit and the like may be formed on these substrates.

The formation of each color pixel by the photolithography method can be performed by a known or conventional device or condition. For example, it can be produced as follows.
First, the colored curable resin composition is applied onto a substrate and dried by heating and drying (pre-baking) and / or under reduced pressure to remove volatile components such as a solvent to obtain a smooth colored composition layer.
Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.
The temperature for heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.
When drying under reduced pressure, it is preferable to carry out drying under a pressure of 50 to 150 Pa in a temperature range of 20 to 25 ° C.
The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected depending on the film thickness of the target color filter.

The coloring composition layer is then exposed via a photomask to form the desired coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
As the light source used for exposure, a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, light less than 350 nm is cut by using a filter that cuts this wavelength range, and light near 436 nm, 408 nm, and 365 nm is selectively extracted by using a bandpass filter that extracts these wavelength ranges. You may do it. Specific examples thereof include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps and the like.
An exposure device such as a mask aligner and a stepper should be used because it is possible to uniformly irradiate the entire exposed surface with parallel rays and to accurately align the photomask with the substrate on which the coloring composition layer is formed. Is preferable.

A coloring pattern is formed on the substrate by bringing the exposed coloring composition layer into contact with a developing solution for development. By development, the unexposed portion of the colored composition layer is dissolved in a developer and removed. As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Further, the developer may contain a surfactant.
The developing method may be any of a paddle method, a dipping method, a spray method and the like. Further, the substrate may be tilted at an arbitrary angle during development.
After development, it is preferable to wash with water.

Further, it is preferable to post-bake the obtained coloring pattern. The post-bake temperature is preferably 150 to 250 ° C, more preferably 160 to 235 ° C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

According to the color curable resin composition of the present invention, it is possible to produce a color filter having particularly excellent contrast. The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state image sensor.

Hereinafter, the colored curable resin composition of the present invention will be described in more detail by way of examples. Unless otherwise specified, "%" and "part" in the example are mass% and parts by mass.
In the following synthetic examples, the compounds were identified by mass spectrometry (LC; Agilent 1200, MASS; Agilent LC / MSD) or elemental analysis (VARIO-EL; (Elemental)).

Synthesis example 1
3 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 300 parts of methanol were mixed. While keeping the temperature of the obtained mixture at 5 ° C or lower, 2.71 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise over 30 minutes, and the mixture was stirred at 5 ° C for 6 hours. did. 14 parts of acetic acid was added while keeping the temperature of the obtained mixture below 5 ° C. To the resulting mixture, 12 parts of 5-cyano-4-oxo-pentanoic acid (synthesized according to the method described in Journal of Organic Chemistry, 1992, 57 (18), 5005-5013) was added and 26 at 45 ° C. Stir for hours. The obtained mixture was filtered, and the residue was washed with 300 parts of water, 300 parts of methanol, and 15 parts of N, N-dimethylformamide in this order. The obtained residue was dried under reduced pressure at 60 ° C. to obtain 7.4 parts of a compound represented by the formula (I-1) (compound No. 136, hereinafter sometimes referred to as compound (I-1)). (Yield 80%).

<Identification of the compound represented by the formula (I-1) (Compound No. 136)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 394
Exact Mass: 393

Synthesis example 2
Same as Synthesis Example 1 except that 12 parts of 5-cyano-4-oxo-pentanoic acid of Synthesis Example 1 were replaced with 14 parts of 4- (2-cyanoacetyl) benzoic acid (synthesized according to the method described in US2680731). The compound represented by the formula (I-2) (compound number 46; hereinafter may be referred to as compound (I-2)) was obtained in 10 parts (yield 83%).

<Identification of compound represented by formula (I-2) (Compound No. 46)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 490
Exact Mass: 489

Synthesis example 3
(1) Synthesis of o-cyanoacetylphenylacetic acid 18 parts of 2- (2-methoxy-2-oxoethyl) benzoic acid (synthesized according to the method described in WO2015 / 100363) was dissolved in 540 parts of THF. While keeping the temperature of the obtained mixture at -50 ° C or lower, 371 parts of a hexane solution of 1 mol / L lithium bis (trimethylsilyl) amide (manufactured by Kanto Chemical Co., Ltd.) was added dropwise over 120 minutes and stirred for 30 minutes. .. While keeping the temperature below −50 ° C., 23 parts of acetonitrile (manufactured by Kanto Chemical Co., Inc.) was added dropwise over 90 minutes, the temperature was raised to 25 ° C., and the mixture was stirred at 25 ° C. for 6 hours. The reaction mixture was washed with water, the ethyl acetate extract was dried over anhydrous sodium sulfate, the solvent was distilled off after filtration, and the residue was purified by reprecipitation with ethyl acetate / n-hexane (volume ratio 2/1). -Cyanoacetylphenylacetic acid 13 parts was obtained (yield 69%).
(2) Synthesis of compound represented by formula (I-3) (Compound No. 73) 3 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 300 parts of methanol were mixed. While keeping the temperature of the obtained mixture at 5 ° C or lower, 2.71 parts of a 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise over 30 minutes, and the mixture was stirred at 5 ° C for 6 hours. did. 14 parts of acetic acid was added while keeping the temperature of the obtained mixture below 5 ° C. To the obtained mixture, 11 parts of o-cyanoacetylphenylacetic acid was added, and the mixture was stirred at 45 ° C. for 26 hours. The obtained mixture was filtered, and the residue was washed with 300 parts of water, 300 parts of methanol, and 15 parts of N, N-dimethylformamide in this order. The obtained residue was dried under reduced pressure at 60 ° C. to obtain 9 parts of a compound represented by the formula (I-3) (compound No. 73; hereinafter, sometimes referred to as compound (I-3)) (yield). Rate 71%).

<Identification of the compound represented by the formula (I-3) (Compound No. 73)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 518
Exact Mass: 517

Synthesis example 4
(1) Synthesis of 4-carboxy-1- (4-cyano-3-oxybutyl) benzene Methyl 4-carboxy-1-benzenepropionate (synthesized according to the method described in WO2005 / 012220) 30.0 parts of THF900 It was dissolved in the part. While keeping the temperature of the obtained mixture at -50 ° C or lower, 576 parts of a hexane solution of 1 mol / L lithium bis (trimethylsilyl) amide (manufactured by Kanto Chemical Co., Ltd.) was added dropwise over 120 minutes and stirred for 30 minutes. .. While keeping the temperature below −50 ° C., 36 parts of acetonitrile (manufactured by Kanto Chemical Co., Inc.) was added dropwise over 90 minutes, the temperature was raised to 25 ° C., and the mixture was stirred at 25 ° C. for 6 hours. The reaction mixture was washed with water, the ethyl acetate extract was dried over anhydrous sodium sulfate, the solvent was distilled off after filtration, and the residue was purified by reprecipitation with ethyl acetate / n-hexane (volume ratio 2/1). -Carbox-1- (4-cyano-3-oxybutyl) benzene 26.6 parts was obtained (yield 85%).
(2) Synthesis of compound represented by the formula (I-4) (Compound No. 154) 12 parts of 5-cyano-4-oxo-pentanoic acid of Synthesis Example 1 are 4-carboxy-1- (4-cyano-3). -Synthesis was carried out in the same manner as in Synthesis Example 1 except that 12 parts of oxybutyl) benzene was used, and the compound represented by the formula (I-4) (compound number 154; hereinafter referred to as compound (I-4)) may be used. 7.7 parts were obtained (yield 60%).

<Identification of the compound represented by the formula (I-4) (Compound No. 154)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 546
Exact Mass: 545

Synthesis example 5
(1) Synthesis of p-cyanoacetylphenylacetic acid Except that 2- (2-methoxy-2-oxoethyl) benzoic acid in Synthesis Example 3 (1) was changed to 4- (2-methoxy-2-oxoethyl) benzoic acid. The synthesis was performed in the same manner. 13 parts of p-cyanoacetylphenylacetic acid was obtained (yield 70%).
(2) Synthesis of the compound represented by the formula (I-5) (Compound No. 82) Synthesis Example 3 (Synthesis Example 3) except that o-cyanoacetylphenylacetic acid in Synthesis Example 3 (2) was changed to p-cyanoacetylphenylacetic acid. The synthesis was performed in the same manner as in 2). 8.7 parts of the compound represented by the formula (I-5) (compound No. 82; hereinafter may be referred to as compound (I-5)) were obtained (yield 68%).

<Identification of the compound represented by the formula (I-5) (Compound No. 82)>
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] ⁺ 518
Exact Mass: 517

Synthesis example 6
174 g of tert-amyl alcohol and 22.2 g of metallic sodium were reacted at 130 ° C. under a nitrogen atmosphere to synthesize sodium tert-amyl alcoholate. This is heated to 60 ° C., 91.0 g of 4-bromobenzonitrile, 71.05 g of succinic acid di-tert-amyl ester, and 108.9 g of tert-amyl alcohol are added so that the liquid temperature becomes 85 ° C. or lower. Stir for hours. The suspension was further stirred for 18 hours or more, and then added to a mixture of 200 g of methanol cooled to −10 ° C., 1000 g of water and 49.21 g of sulfuric acid. After the addition of the suspension was completed, the mixture was kept at 0 ° C. and stirred for 5 hours to complete the reaction, and then the solid content was filtered. The solids were washed alternately with methanol and water until the filtrate was no longer colored and no salt was deposited. Then, the solid content was dried in a vacuum dryer at 80 ° C. for 18 hours to obtain the desired red pigment (A-1). The obtained amount was 107 g.

Synthesis example 7
An appropriate amount of nitrogen was poured into a 1 L flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace it with a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80 ° C. with stirring. Then 38 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8-ylacrylate and 3,4-epoxytricyclo [5.2.2.10 ^{2, 6} ] A mixed solution of 289 parts of a mixture of decane-9-ylacrylate and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. On the other hand, a mixed solution prepared by dissolving 33 parts of 2,2-azobis (2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropping, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B1) having a solid content of 35.0%. The weight average molecular weight of the obtained resin B1 was 8800, the dispersibility was 2.1, and the acid value in terms of solid content was 77 mg-KOH / g.
Solvent; THF (tetrahydrofuran)
Flow velocity; 1.0 mL / min
Detector; RI
Calibration standard material; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
The ratio (Mw / Mn) of the polystyrene-equivalent weight average molecular weight and the number average molecular weight obtained above was taken as the molecular weight distribution.

Synthesis example 8
An appropriate amount of nitrogen was poured into a 1 L flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace it with a nitrogen atmosphere, 371 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 85 ° C. with stirring. Then, 54 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8-ylacrylate and 3,4-epoxytricyclo [5.2.2.10 ^{2, 6} ] A mixed solution of 225 parts of a mixture of decane-9-ylacrylate, 81 parts of vinyl toluene (isomer mixture) and 80 parts of propylene glycol monomethyl ether acetate was added dropwise over 4 hours. On the other hand, a solution prepared by dissolving 30 parts of the polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the dropping of the initiator solution was completed, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a solution of a copolymer (resin B3) having a solid content of 37.5%. The weight average molecular weight of the obtained resin B3 was 10600, the dispersity was 2.0, and the acid value in terms of solid content was 112 mg-KOH / g.

The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin were measured by using the GPC method under the following conditions.
Equipment; K2479 (manufactured by Shimadzu Corporation)
Column; SHIMADZU Shima-pack GPC-80M
Column temperature; 40 ° C

Examples 1 to 6, Comparative Examples 1 to 3
(1) Preparation of Colored Curable Resin Composition The components shown in Table 7 were mixed, and a dispersion liquid in which compound (I) was dispersed was prepared using a bead mill.

Separately, the components shown in Table 8 were mixed to obtain a red pigment dispersion liquid in which the red pigment was dispersed using a bead mill. The red pigment (A-1) in the table is the red pigment obtained in Synthesis Example 6. The red pigment (A-2) in the table is C.I. I. Pigment Red 177.

Then, the components shown in Tables 9 and 10 were mixed to obtain a colored curable resin composition.

（Ｅ－１）：４－ヒドロキシ－４－メチル－２－ペンタノン（ジアセトンアルコールともいう）
（Ｅ－２）：プロピレングリコールモノメチルエーテルアセテート
（Ｆ－１）：ポリエーテル変性シリコーンオイル（トーレシリコーンＳＨ８４００；東レダウコーニング（株）製） However, each symbol represents the following compound.
(AX1): C.I. I. Pigment Yellow 185
(A-X2): C.I. I. Pigment Yellow 139
(B-1): Resin B1 (in terms of solid content)
(B-2): Resin B3 (solid content conversion)
(C-1): Dipentaerythritol polyacrylate (“A9550” manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
(D-1): Compound represented by the formula (d) (manufactured by Changzhou Powerful Electronics New Material Co., Ltd.)

(E-1): 4-Hydroxy-4-methyl-2-pentanone (also referred to as diacetone alcohol)
(E-2): Propylene glycol monomethyl ether acetate (F-1): Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

(2) Preparation of colored coating film A spin-coating method is performed on a 5 cm square glass substrate (Eagle XG; manufactured by Corning Inc.) with a colored curable resin composition so that the film thickness after post-baking is about 2 to 3 μm. Then, it was prebaked at 100 ° C. for 3 minutes to form a colored composition layer. After allowing to cool, the colored composition layer formed on the substrate was exposed to light at an exposure amount of 80 mJ / cm ² (365 nm standard) under an atmospheric atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). Irradiated. After light irradiation, post-baking was performed at 230 ° C. for 30 minutes in an oven to obtain a colored coating film.

(3) Thickness measurement The thickness of the obtained colored coating film was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.).

(4) Saturation evaluation The obtained colored coating film was measured for spectroscopy using a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.), and the CIE XYZ table was used using the characteristic function of the C light source. The xy chromaticity coordinates (x, y) and the stimulus value Y in the color system were measured. The larger the value of Y, the higher the brightness. The results are shown in Tables 11 and 12.

(5) Contrast evaluation Contrast meter (CT-1: Tsubosaka Electric Co., Ltd., color difference meter BM-5A: Topcon Co., Ltd., light source: F-10, polarizing film: Tsubosaka Electric Co., Ltd.) (Co., Ltd.) was used to measure the contrast. The blank value at the time of measurement is 30,000. The results are shown in Tables 11 and 12.

As shown in Table 11, Examples 1 to 5 in which the red pigment (A-1) and any of the compounds (I-1) to (I-5) are combined have higher contrast than Comparative Examples 1 and 2. It was excellent. Further, as shown in Table 12, Example 6 in which the red pigment (A-2) and the compound (I-2) were combined had excellent contrast as compared with Comparative Example 3. Example 6 had a thicker film thickness than Comparative Example 3, but had a higher contrast.

According to the colored curable resin composition of the present invention, it is possible to produce a color filter having particularly excellent contrast.

Claims (4)

Contains colorants, resins, polymerizable compounds and polymerization initiators
A coloring curable resin composition containing a compound represented by the following formula (IA) and a red pigment as a coloring agent.

[In formula (IA),
R ^1a represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and is contained in the hydrocarbon group-CH. When _2- and the heterocyclic group contain -CH _2- , which does not form a ring, the -CH _2- is replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . May be. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— .
R ^2a to R ^5a are independent of each other, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group which may have a substituent, a hydrogen atom, a halogen atom, and a cyano. When it represents a group, a nitro group, -CO ₂ ^- or -S (O) _{2 O-} , and contains -CH _2- contained in the hydrocarbon group and -CH ^2- in which the heterocyclic group does not form a ring . The -CH _2- may be replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the hydrocarbon group and the heterocyclic group may have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . At least one set of R ^2a and R ^3a , R ^3a and R ^4a , and R ^4a and R ^5a , together with the carbon atom to which each bond, forms a ring that may have a substituent. However, when the ring contains -CH _2- , which does not form a ring, the -CH ₂ -is replaced with -O-, -CO-, -S (O) _2- or -NR ^na- . May be good. However, the replacement of -CH _2- does not form -COOH or -S (O) ₂ OH. Further, the ring may have at least one selected from the group consisting of —CO ₂ ⁻ and —S (O) ₂ O ⁻ .
R ^na represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a heterocyclic group or a hydrogen atom which may have a substituent, and the hydrocarbon group and the heterocyclic group. May have at least one selected from the group consisting of —CO _2- ^and —S (O) ₂ O ^— . When there are a plurality of R ^na , they may be the same or different.
R ^6a and R ^8a independently represent -CO-OR ^na2 , -CO-NH (R ^na2 ), -CO-N (R ^na2 ) ₂ or -CO-R ^na 2 .
R ^na2 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and is contained in the hydrocarbon group-CH 2- _. And when the heterocyclic group contains -CH _2- , which does not form a ring, the -CH _2- may be replaced with -O- , -CO-, -S (O) _2- or -NR ^na10- . good. However, the replacement of -CH _2- does not form -COOH and -S (O) ₂ OH. Further ^, the hydrocarbon group or the heterocyclic group has at least one -CO _2- . When there are a plurality of R ^na2 , they may be the same or different.
R ^na10 represents a hydrocarbon group having 1 to 35 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, and when a plurality of R ^na10 are present, they are the same. But it can be different.
R ^7a and R ^9a represent a cyano group.
M ^{b +} represents a hydron or b-valent metal ion. When there are a plurality of M ^{b +} , they may be the same or different.
b represents an integer of 1 to 6.
aa represents an integer of 2 to 10.
ma represents the number of M ^{b +} .
na is a number that satisfies the relationship of na = b × ma / aa. ] The colored curable resin composition according to claim 1, further comprising a solvent. A color filter formed from the colored curable resin composition according to claim 1 or 2 . A display device including the color filter according to claim 3 .