WO2019171999A1 - Coloring agent dispersion, coloring curable resin composition, color filter and display device - Google Patents

Coloring agent dispersion, coloring curable resin composition, color filter and display device Download PDF

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Publication number
WO2019171999A1
WO2019171999A1 PCT/JP2019/006984 JP2019006984W WO2019171999A1 WO 2019171999 A1 WO2019171999 A1 WO 2019171999A1 JP 2019006984 W JP2019006984 W JP 2019006984W WO 2019171999 A1 WO2019171999 A1 WO 2019171999A1
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Prior art keywords
group
ring
substituent
hydrocarbon group
carbon atoms
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PCT/JP2019/006984
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French (fr)
Japanese (ja)
Inventor
学 栂井
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住友化学株式会社
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Application filed by 住友化学株式会社 filed Critical 住友化学株式会社
Priority to KR1020207028203A priority Critical patent/KR102637673B1/en
Priority to CN201980016992.8A priority patent/CN111836859B/en
Publication of WO2019171999A1 publication Critical patent/WO2019171999A1/en

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B25/00—Quinophthalones

Definitions

  • the present invention relates to a colorant dispersion, a colored curable resin composition, a color filter, and a display device.
  • Colored curable resin compositions are used in the manufacture of color filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays.
  • a display device using a color filter is required to have high contrast.
  • Patent Document 1 describes C.I. which is a yellow pigment in order to improve the contrast of a display device.
  • C.I. which is a yellow pigment in order to improve the contrast of a display device.
  • Pigment Yellow 138 containing C.I.
  • the inclusion of a sulfonated derivative of CI Pigment Yellow 138 is described.
  • the object of the present invention is C.I. I.
  • Another object is to provide a color filter formed from the colored curable resin composition and a display device including the color filter.
  • the present invention provides the following colorant dispersion, colored curable resin composition, color filter, and display device.
  • C.I. A colorant dispersion containing a co-dispersion of CI Pigment Yellow 138 (A) and the compound (B) represented by the formula (I).
  • a represents the total number of —CO 2 — and —S (O) 2 O — contained in the compound represented by the formula (I), and is an integer of 0 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 which may have a substituent or a hydrogen atom, and —CH contained in the hydrocarbon group 2 - the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO -, - S (O) 2 - or -NR na - to have replaced May be.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 each independently 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, cyano.
  • —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 —, or —NR na —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 selected from the group consisting 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 combined with the carbon atom to which each is bonded.
  • —CH 2 — represents —O—, —CO—, —S (O) 2 — or —NR na —
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 — .
  • M b + represents hydron or a b-valent metal ion. When a plurality of M b + are present, these may be the same or different.
  • M b + is hydrone
  • the hydrone is present 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 + .
  • R 1 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, and —CH contained in the hydrocarbon group 2 - the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO -, - S (O) 2 - or -NR nb - to have replaced May be. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 2 to R 5 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • At least one selected from the group consisting of R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may have a substituent together with the carbon atom to which each is bonded.
  • a ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR nb — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 6 represents —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 .
  • R 6 represents —CO—NH (R nb1 )
  • R 2 to R 5 satisfy at least one of (ib) and (iib).
  • At least one of R 2 to R 5 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR nb — may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR nb- may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 2 to R 5 which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, —O—, —CO—, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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, -CH 2 - contained in the hydrocarbon group and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 -Or -NR nb- may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 7 may be combined with the carbon atom to which R 6 and R 7 are bonded to form a ring.
  • X represents a group represented by the formula (1a).
  • R 17b and R 18b each independently represent 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 17b and R 18b may form a ring optionally having a substituent together with the carbon atom to which each is bonded, and when the ring contains —CH 2 — that does not form a ring,
  • the —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR nb —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • * 1 represents a bond to the 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.
  • 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 —CH 2 — contained in the hydrocarbon group and it is, -O - - the -CH 2 when including - heterocyclic group -CH 2 that does not constitute a ring, - CO -, - S ( O) 2 - or -NR NB 10 - may be replaced by .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 two or more Rnb10 exists, these may be the same and may differ. ]
  • R 19b and R 20b each independently represent 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, the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring - -CH 2 contained in the hydrogen group, -O -, - CO -, - S (O) 2 - or -NR nb- may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R nb represents the same meaning as described above. * 2 represents a bond to the isoindoline ring.
  • R 2 to R 5 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR na — may be substituted.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 selected from the group consisting of R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may have a substituent together with the carbon atom to which each is bonded.
  • a ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR na — May be replaced.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
  • R 6 represents —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 .
  • R 6 represents —CO—NH (R na1 )
  • R 2 to R 5 satisfy at least one of (ia) and (ia).
  • At least one of R 2 to R 5 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR na — may be substituted.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 selected from the group consisting of R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR It may be replaced with na-.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
  • R 2 to R 5 which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, It may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 7 represents a cyano group.
  • X represents a group represented by the formula (1a-x).
  • R 21 and R 22 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 together with the carbon atom to which each is bonded may form a ring that may have a substituent, and when the ring contains —CH 2 — that does not form a ring
  • the —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
  • * 1 represents a bond to the isoindoline ring.
  • R na represents 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 —CH 2 — contained in the hydrocarbon group and it is, -O - - the -CH 2 when including - heterocyclic group -CH 2 that does not constitute a ring, - CO -, - S ( O) 2 - or -NR NA 10 - may be replaced by .
  • —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —.
  • 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 na1 represents an optionally substituted hydrocarbon group having 1 to 35 carbon atoms or an optionally substituted heterocyclic group, and when there are a plurality of Rna10 , these are the same. But it may be different.
  • R 7 is the colorant dispersion according to [1] or [2], in which R 7 represents a cyano group.
  • R 23 and R 24 each independently represent 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
  • the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring - -CH 2 contained in the hydrogen group
  • -O -, - CO -, - S (O) 2 - or -NR na- may be substituted.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 represents the same meaning as described above.
  • * 2 represents a bond to the isoindoline ring.
  • [5] The colorant dispersion according to any one of [1] to [4], further comprising a metal salt (C) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms and having a hydroxy group.
  • a colored curable resin composition comprising the colorant dispersion according to any one of [1] to [5] and a resin (D).
  • [8] A display device including the color filter according to [7].
  • the colorant dispersion and colored curable resin composition according to the present invention can provide a color filter exhibiting good contrast and a display device including the same.
  • the colorant dispersion of the present invention contains C.I. I. Pigment Yellow 138 (A) and a compound (B) represented by the formula (I) are included.
  • the colorant dispersion may further contain a metal salt (C) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms and having a hydroxy group.
  • the metal salt (C) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms and having a hydroxy group is also referred to as “aliphatic carboxylic acid metal salt (C)”.
  • aliphatic carboxylic acid metal salt (C) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms and having a hydroxy group
  • I. Pigment Yellow 138 (A) C. contained in co-dispersion.
  • I. Pigment Yellow 138 (A) is a yellow pigment classified as a pigment by the Color Index (published by The Society of Dyers and Colorists).
  • a represents the total number of —CO 2 — and —S (O) 2 O — contained in the compound represented by the formula (I), and is an integer of 0 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 which may have a substituent or a hydrogen atom, and —CH contained in the hydrocarbon group 2 - the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO -, - S (O) 2 - or -NR na - to have replaced May be.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 each independently 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, cyano.
  • —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 —, or —NR na —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 selected from the group consisting 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 combined with the carbon atom to which each is bonded.
  • —CH 2 — represents —O—, —CO—, —S (O) 2 — or —NR na —
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 — .
  • M b + represents hydron or a b-valent metal ion. When a plurality of M b + are present, these may be the same or different.
  • M b + is hydrone
  • the hydrone is present 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 + .
  • R 1 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, and —CH contained in the hydrocarbon group 2 - the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO -, - S (O) 2 - or -NR nb - to have replaced May be. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 2 to R 5 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • At least one selected from the group consisting of R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may have a substituent together with the carbon atom to which each is bonded.
  • a ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR nb — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 6 represents —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 .
  • R 6 represents —CO—NH (R nb1 )
  • R 2 to R 5 satisfy at least one of (ib) and (iib).
  • At least one of R 2 to R 5 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR nb — may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR nb- may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 2 to R 5 which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, —O—, —CO—, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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, -CH 2 - contained in the hydrocarbon group and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 -Or -NR nb- may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 7 may be combined with the carbon atom to which R 6 and R 7 are bonded to form a ring.
  • X represents a group represented by the formula (1a).
  • R 17b and R 18b each independently represent 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 17b and R 18b may form a ring optionally having a substituent together with the carbon atom to which each is bonded, and when the ring contains —CH 2 — that does not form a ring,
  • the —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR nb —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • * 1 represents a bond to the 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.
  • 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 —CH 2 — contained in the hydrocarbon group and it is, -O - - the -CH 2 when including - heterocyclic group -CH 2 that does not constitute a ring, - CO -, - S ( O) 2 - or -NR NB 10 - may be replaced by .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 two or more Rnb10 exists, these may be the same and may differ. ]
  • the group represented by the formula (1a) is preferably a group represented by the formula (2a).
  • R 19b and R 20b each independently represent 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, the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring - -CH 2 contained in the hydrogen group, -O -, - CO -, - S (O) 2 - or -NR nb- may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R nb represents the same meaning as described above. * 2 represents a bond to the isoindoline ring.
  • -CH 2 - represents a group or a nitro group
  • -O -, - CO- , —S (O) 2 — or —NR na — may be substituted.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 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 is bonded forms a ring that may have a substituent.
  • -CH 2 is good, the ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR na - be replaced in Good.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
  • R 6 represents —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 .
  • R 6 represents —CO—NH (R na1 )
  • R 2 to R 5 satisfy at least one of (ia) and (ia).
  • At least one of R 2 to R 5 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR na — may be substituted.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 selected from the group consisting of R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR It may be replaced with na-.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
  • R 2 to R 5 which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, It may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 7 represents a cyano group.
  • X represents a group represented by the formula (1a-x).
  • R 21 and R 22 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 together with the carbon atom to which each is bonded may form a ring that may have a substituent, and when the ring contains —CH 2 — that does not form a ring
  • the —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
  • * 1 represents a bond to the isoindoline ring.
  • R na represents 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 —CH 2 — contained in the hydrocarbon group and it is, -O - - the -CH 2 when including - heterocyclic group -CH 2 that does not constitute a ring, - CO -, - S ( O) 2 - or -NR NA 10 - may be replaced by .
  • —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —.
  • 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 na1 When a plurality of R na1 are present, these may be the same or different.
  • R na10 represents an optionally substituted hydrocarbon group having 1 to 35 carbon atoms or an optionally substituted heterocyclic group, and when there are a plurality of Rna10 , these are the same. But it may be different.
  • R 7 represents a cyano group.
  • the group represented by the formula (1a-x) is preferably a group represented by the formula (2a-x).
  • R 23 and R 24 each independently represent 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
  • the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring - -CH 2 contained in the hydrogen group
  • -O -, - CO -, - S (O) 2 - or -NR na- may be substituted.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 represents the same meaning as described above.
  • * 2 represents a bond to the isoindoline ring.
  • R 11b to R 15b each have the same meaning as R 1 to R 5 when a is 0 in formula (I). At least one selected from the group consisting of R 12b and R 13b , R 13b and R 14b , and R 14b and R 15b may have a substituent together with the carbon atom to which each is bonded.
  • a ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR nb — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 .
  • R 16b represents —CO—NH (R nb1 )
  • R 12b to R 15b satisfy at least one of (ixb) and (ixb).
  • At least one of R 12b to R 15b may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR nb — may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • At least one set selected from the group consisting of R 12b and R 13b , R 13b and R 14b , and R 14b and R 15b has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR nb- may be substituted .
  • —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —.
  • R 12b to R 15b which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, —O—, —CO—, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • X 1b represents a group represented by the formula (1a-xb).
  • R 21b , R 22b and * 1 represent the same meaning as R 17b , R 18b and * 1 in the formula (1a), respectively.
  • R nb and R nb1 represent the same meaning 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 zero.
  • the group represented by the formula (1a-xb) is preferably a group represented by the formula (2a-xb).
  • R 23b , R 24b and * 2 represent the same meaning as R 19b , R 20b and * 2 in the formula (2a), respectively.
  • R nb represents the same meaning as described above.
  • R 1a to R 9a represent the same meaning as R 1 to R 9 in the case where a is any integer of 1 to 10 in the formula (I), respectively. At least one selected from the group consisting 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 is combined with the carbon atom to which each is bonded.
  • 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 is combined with the carbon atom to which each is bonded.
  • To form an optionally substituted ring and when the ring contains —CH 2 — that does not form a ring, —CH 2 — represents —O—, —CO—, —S (O) 2 — or —NR na — may be substituted.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
  • R na and M b + represent the same meaning as described above.
  • b represents an integer of 1 to 6.
  • aa represents the total number of —CO 2 — and —S (O) 2 O — contained in the compound represented by the formula (IA), and is an integer of 1 to 10.
  • ma represents the number of M b + .
  • R 1b to R 5b represent the same meaning as R 1 to R 5 when a is 0 in formula (I), respectively.
  • 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 may have a substituent together with the carbon atom to which each is bonded.
  • a ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR nb — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 6b 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 .
  • R 6b represents —CO—NH (R nb1 )
  • R 2b to R 5b satisfy at least one of (ibb) and (iibb).
  • 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 that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR nb — may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • 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 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR nb- may be substituted .
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 2b to R 5b which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, —O—, —CO—, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R 7b represents the same meaning as R 7 when a is 0 in formula (I).
  • R 7b may form a ring together with the carbon atom to which R 6b and R 7b are bonded.
  • Xb represents the same meaning as X when a is 0 in formula (I).
  • R nb , R nb1 and R nb10 represent the same meaning as described above.
  • the total number of —CO 2 H and —S (O) 2 OH contained in the compound represented by the formula (IB) is zero.
  • the group represented by the formula (1a) is preferably a group represented by the formula (2a).
  • the carbon number of the hydrocarbon group having a substituent is the carbon number of the hydrocarbon group before being substituted by the substituent.
  • the carbon number of the formed group is the carbon number of the hydrocarbon group before being substituted by the group.
  • group (Z) By replacing —CH 2 — contained in the hydrocarbon group with —O—, —CO—, —S (O) 2 —, —NR na —, —NR nb —, —NR na10 — or —NR nb10 —.
  • group (Z) the formed groups are also collectively referred to as “group (Z)”.
  • R 1 to R 9 , R 11b to R 16b , R 1a to R 9a R 1b to R 7b , R na , R nb , R na1 , R nb1 , R na10 , R nb10 , R 17b to R 24b , and R 21 to R 24 are usually monovalent groups. .
  • the hydrocarbon group having 1 to 35 carbon atoms represented by 1 to 40 hydrocarbon group, R na1 , R nb1 , R na10 and R nb10 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group.
  • the aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain or alicyclic.
  • the hydrocarbon groups represented by R 1 to R 9 , R 1a to R 9a , R 21 to R 24 and R na are represented by —CO 2 — and — It may have at least one selected from the group consisting of S (O) 2 O 2 — .
  • R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 Saturated or unsaturated chain hydrocarbon groups represented by R na10 and R nb10 are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl Group, undecyl group, dodecyl group, heptadecyl group, linear alkyl group such as octadecyl group and icosyl group, etc .; isopropyl group, (2-methyl) propyl group, isobutyl group, sec-butyl group, tert-butyl group, ( 2-ethyl) buty
  • R 1 to R 9 Saturation represented by R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24
  • the number of carbon atoms of the unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, still more preferably 1 to 10, and even more. More preferably, it is 1-8, and particularly preferably 1-5.
  • the carbon number of the saturated or unsaturated chain hydrocarbon group represented by R na1 , R nb1 , R na10 and R nb10 is preferably 1 to 28, more preferably 1 to 18, and still more preferably 1 -13, even more preferably 1-8, even more preferably 1-6, and particularly preferably 1-3.
  • the saturated or unsaturated alicyclic hydrocarbon group represented by R na10 and R nb10 includes a cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methyl Cyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethyl group Cyclohexyl, 2,
  • the saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20, more preferably 4 to 20, and still more preferably 4 to 15 carbon atoms. And more preferably 5 to 15, particularly preferably 5 to 10, and particularly preferably a cyclopentyl group, a cyclohexyl group, a cycloheptyl group or a cyclooctyl group.
  • the saturated or unsaturated hydrocarbon group represented by R na10 and R nb10 may be a group in which the chain hydrocarbon group and the alicyclic hydrocarbon group listed above are combined.
  • cyclopropyl An alkyl group to which one or more alicyclic hydrocarbon groups such as methyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group and cyclohexylethyl group are bonded Is mentioned.
  • the number of carbon atoms of a group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group is preferably 4 to 30, more preferably 4 to 20, and still more preferably 4 to 15.
  • the aromatic hydrocarbon groups represented by R na10 and R nb10 include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,3-dimethylphenyl group, and a 2,4-dimethylphenyl group.
  • the aromatic hydrocarbon group represented by R na10 and R nb10 is not particularly limited as long as it is a hydrocarbon group having an aromatic hydrocarbon ring, and the chain hydrocarbon group and alicyclic hydrocarbon listed above Group and at least one of the aromatic hydrocarbon groups may be a group in combination with the aromatic hydrocarbon group listed above, for example, benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, Aralkyl groups such as 4-methylbenzyl group, phenylethyl group, phenylpropyl group and 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl
  • the number of carbon atoms of a group obtained by combining at least one of a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group with an aromatic hydrocarbon group is preferably 7 to 30, and more preferably 7 -20, more preferably 7-15.
  • the hydrocarbon groups represented by R nb1 , R na10 and R nb10 may have a monovalent substituent or a divalent substituent.
  • the divalent substituent is preferably a substituent in which two bonds are bonded to the same carbon atom to form a double bond.
  • An alkylsulfanyl 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 perfluorodecyl group, perfluorocyclohexyl group and perfluorophen
  • R nb2 , R nb3 , and R nb4 may be the same or different, and independently of each other, may have a hydrocarbon group having 1 to 35 carbon atoms, or a substituent. to represent also heterocyclic group optionally, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O- , —CO—, —S (O) 2 —, and —N nb10 — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • R nb10 represents the same meaning as described above. Specific examples and preferred examples of R nb2, R nb3, R nb4 is the same as R nb1. ]
  • Examples of the divalent substituent include 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. Groups and the like.
  • Examples of the imino group substituted with an aryl group include C 6 H 5 —N ⁇ .
  • —CH 2 — contained in the hydrocarbon group represented by R 1 to R 9 , R 1a to R 9a , R 21 to R 24 is —O— , —CO—, —S (O) 2 —, or —NR na — may be substituted.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • —CH 2 — contained in the hydrocarbon group represented by R 1 to R 5 , R 7 , R 11b to R 15b , R 1b to R 5b , R 7b , R 17b to R 24b May be replaced by —O—, —CO—, —S (O) 2 — or —NR nb —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • —CH 2 — contained in the hydrocarbon group represented by R na1 may be replaced by —O—, —CO—, —S (O) 2 —, or —NR na10 —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • —CH 2 — contained in the hydrocarbon group represented by R nb1 may be replaced by —O—, —CO—, —S (O) 2 —, or —NR nb10 —.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the heterocyclic group represented by R na10 and R nb10 may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a hetero atom as a ring component.
  • the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.
  • the number of carbon atoms in the heterocyclic group is preferably 2-30, more preferably 3-22, still more preferably 3-20, still more preferably 3-18, and even more preferably 3 -15, particularly preferably 3-14.
  • a is an integer of 1 to 10
  • the heterocyclic group represented by R 1 to R 9 , R 21 to R 24 , R na and R na1 is represented by —CO 2 — and —S (O ) 2 O - may have at least one selected from the group consisting of.
  • Heterocycles containing only nitrogen atoms as heteroatoms include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; pyrroles such as 2,5-dimethylpyrrole, 2-methylpyrazole and 3-methylpyrazole And 5-membered unsaturated heterocyclic rings such as imidazole, 1,2,3-triazole and 1,2,4-triazole; pyrimidines such as pyridine, pyridazine and 6-methylpyrimidine, pyrazines, and 6-membered unsaturated heterocycles such as 1,3,5-triazine; indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro (3-methyl ) Quinoxalines such as quinoxaline and 3-methylquinoxaline Condensed bicyclic heterocycles such as qui
  • Heterocycles containing only oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, and 1-cyclopentyldioxolane; Bicyclic saturated heterocycles such as 4-dioxaspiro [4.5] decane and 1,4-dioxaspiro [4.5] nonane; ⁇ -acetolactone, ⁇ -propiolactone, ⁇ -butyrolactone, and ⁇ -valero Lactone heterocycles such as lactones; 5-membered unsaturated heterocycles such as furans such as 2,3-dimethylfuran and 2,5-dimethylfuran; 6-membered ring systems such as 2H-pyran and 4H-pyran Unsaturated heterocycles; benzopyrans such as 1-benzofuran and 4-methylbenz
  • Heterocycles containing only sulfur atoms as heteroatoms include 5-membered saturated heterocycles such as dithiolane; 6-membered saturated heterocycles such as thiane, 1,3-dithiane, and 2-methyl-1,3-dithiane
  • a 5-membered unsaturated heterocyclic ring such as thiophene such as 3-methylthiophene and 2-carboxythiophene, 4H-thiopyran, and benzothiopyran such as benzotetrahydrothiopyran; a condensed bicyclic heterocyclic ring such as benzothiophene; Condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.
  • Heterocycles containing nitrogen and oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 2-methyl-2-piperidone; 4 -Monocyclic unsaturated heterocycles such as oxazoles such as methyloxazole, isoxazoles such as 2-methylisoxazole and 3-methylisoxazole; condensations such as benzoxazole, benzisoxazole, benzoxazine, benzodioxan and benzimidazoline Bicyclic heterocycles; condensed tricyclic heterocycles such as phenoxazine; and the like.
  • monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 2-methyl-2-piperidone
  • 4 -Monocyclic unsaturated heterocycles such as oxazoles such as methyl
  • Heterocycles containing nitrogen and sulfur atoms as heteroatoms include monocyclic heterocycles such as 3-methylthiazole and thiazole such as 2,4-dimethylthiazole; condensed bicyclic heterocycles such as benzothiazole; phenothiazine Condensed tricyclic heterocycles such as; and the like.
  • the heterocyclic group may be a group obtained by combining the hydrocarbon groups listed above, and examples thereof include a tetrahydrofurylmethyl group and a methyltetrahydrofuryl group.
  • the bonding position of the above heterocyclic ring is a portion from which an arbitrary hydrogen atom contained in each ring is eliminated.
  • the heterocyclic group represented by R 1 to R 9 , R 1a to R 9a , R 21 to R 24 includes —CH 2 — that does not form a ring.
  • the —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —, in which case the heterocyclic group is the group (Z) including.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the heterocyclic group represented by R 1 to R 5 , R 7 , R 11b to R 15b , R 1b to R 5b , R 7b , R 17b to R 24b does not form a ring—
  • the —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR nb —, in which case the heterocyclic group is The group (Z) is included.
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the heterocyclic group represented by R na1 contains —CH 2 — that does not constitute a ring, —CH 2 — represents —O—, —CO—, —S (O) 2 —, or —NR na10 —.
  • the heterocyclic group includes the group (Z).
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the —CH 2 — that does not constitute the ring represented by R nb1 is included, the —CH 2 — may be replaced by —O—, —CO— , —S (O) 2 —, or —NR nb10 —.
  • the heterocyclic group includes the group (Z).
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • heterocyclic ring which may contain a nitrogen atom as its constituent elements, this nitrogen atom, R 1 as described above may be bonded.
  • the substituents of the heterocyclic group represented by R na10 and R nb10 include R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R Examples thereof include the same substituents that the hydrocarbon group represented by nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 , R na10, and R nb10 may have.
  • Aliphatic hydrocarbon rings include cyclopropane ring, methylcyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, methylcyclohexane ring, 1,1-dimethylcyclohexane ring, 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 And cycloalkane rings such as cyclohexylcyclohexane ring; cycloalkene rings such as cyclohexene ring, cycloheptene
  • Aromatic hydrocarbon rings include benzene, toluene, o-xylene, m-xylene, p-xylene, isopropylbenzene, tert-butylbenzene, mesitylene, 1,5-bis (2-propyl) benzene, naphthalene, 1, 2,3,4-tetrahydronaphthalene, fluorene, phenanthrene, and anthracene;
  • the number of carbon atoms in the aromatic hydrocarbon ring is, for example, 6 to 30, preferably 6 to 20, and more preferably 6 to 15.
  • R na1 , R nb1 , R na10 and R nb10 are the same as the substituents which the hydrocarbon group represented by Rnb10 may have.
  • —CH 2 — means —O—, —CO—, —S (O) 2 —, —NR na — or —NR nb —.
  • the ring contains the group (Z).
  • —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
  • the heterocyclic ring having two or more ring structures include a heterocyclic ring having a structure of the following formula.
  • One of 9 , or one of R 6 and R 7 and one of R 17b and R 18b are preferably a hydrocarbon group.
  • At least one of R 11b to R 16b , R 21b and R 22b , preferably at least one of R 16b , R 21b and R 22b , more preferably R 16b and one of R 21b and R 22b is a hydrocarbon group It is preferable that 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 is preferably a hydrocarbon group. .
  • At least one of R 1b to R 7b , R 17b and R 18b preferably at least one of R 6b , R 7b , R 17b and R 18b , more preferably one of R 6b and R 7b , and R 17b and R
  • 18b is preferably a hydrocarbon group.
  • —CO—OR na1 and —CO—OR nb1 methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl ) Carbons such as hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group and icosyloxycarbonyl group An oxycarbonyl group to which a hydrocarbon group of 1 to 35 is bonded is preferable, and an oxycarbonyl group to which a hydrocarbon group of 1 to 10 carbons is bonded is more preferable.
  • —CO—NH (R na1 ), —CO—N (R na1 ) 2 , —CO—NH (R nb1 ), —CO—N (R nb1 ) 2 include an 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-hexylcarbamoyl group, N- (2-ethyl) hexylcarbamoyl group, N-heptylcarbamoyl group, N
  • —CO—R na1 and —CO—R nb1 include acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl) hexanoyl group, heptanoyl group, octanoyl
  • a hydrocarbon group such as a group, nonanoyl group, decanoyl group, undecanoyl group, dodecanoyl group, henicosanoyl group, benzoyl group, phenylmethylcarbonyl group, phenylethylcarbonyl group and phenylpropylcarbonyl group, and having 1 to 35 carbon atoms
  • a carbonyl group to which is bonded is preferable, and a carbonyl group to which a group having 1 to 10 carbon atoms is bonded is preferable.
  • —CO—R na1 and —CO—R nb1 which are carbonyl groups to which a hydrocarbon group is bonded, the hydrocarbon group is a halogen atom such as a chlorine atom; a sulfamoyl group; a hydroxy group; An oxy group having 10 hydrocarbon groups bonded to one side; an oxycarbonyl group having 1 to 10 carbon atoms such as a methoxycarbonyl group bonded; and the like.
  • the hydrocarbon group in the carbonyl group to which a hydrocarbon group is bonded, the hydrocarbon group may have —CO 2 —, —S (O) 2 O —, and the like.
  • methylsulfonyl group methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl ) 1 carbon number such as hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, and p-tolylsulfonyl group
  • R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 12b and R 13b , R 13b and R 14b , R 14b and R 15b , 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 , or R 4b and R 5b may be formed together with the carbon atoms to which each is bonded, are represented by formula (I), formula ( IIB), condensed with the benzene ring of the isoindoline skeleton of formula (IA) or formula (IB).
  • R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 12b and R 13b , R 13b and R 14b , R 14b and R 15b , 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 , or R 4b and R 5b may be formed together with the carbon atom to which each is bonded, and the condensed ring structure of the benzene ring
  • indene naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, acanthrylene, triphenylene, pyrene, chrysene, N-methylphthalimide, N- (1-phenylethyl) ) Hydrocarbon-based condensed
  • the ring that R 6a and R 7a , or R 8a and R 9a may form together with the carbon atoms to which each is bonded is an exomethylene (C ⁇ CH 2 ) of the isoindoline skeleton of formula (IA)
  • the ring is exemplified as a structure containing this exomethylene (C ⁇ CH 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. It can be illustrated. ** represents a bond to the isoindoline skeleton.
  • R 25 and R 26 are each independently 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 by —O—, —CO—, —S (O) 2 —, or —NR na —.
  • —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —.
  • 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 — as a substituent.
  • Specific examples and preferred examples of R 25 and R 26 are the same as those of R na1 . ]
  • the ring which R 21 and R 22 may form together with the carbon atom to which each is bonded is bonded to the isoindoline skeleton of formula (I) (C ⁇ CH 2 ),
  • the ring is exemplified as a structure containing this exomethylene (C ⁇ CH 2 ), for example, a structure in which a carbonyl group, an exomethylene, and a carbonyl group are arranged in this order as shown in the following group B can be exemplified.
  • ** represents a bond to the isoindoline skeleton.
  • the ring that R 17b and R 18b , or R 21b and R 22b may form together with the carbon atoms to which each is bonded is an exomethylene (C ⁇ CH 2 ) of the isoindoline skeleton of formula (IIB).
  • C ⁇ CH 2 exomethylene
  • the ring is exemplified as a structure containing this exomethylene (C ⁇ CH 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 C below. It can be illustrated. ** represents a bond to the isoindoline skeleton.
  • R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 12b and R 13b , R 13b and R 14b , R 14b and R 15b , 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 , or R 4b and R 5b may be formed together with the carbon atoms to which they are bonded, each having a substituent Also good.
  • R na1 , R nb1 , R na10 and R nb10 are the same as the substituents which the hydrocarbon group represented by Rnb10 may have.
  • Halogen atoms represented by R 2 to R 9 , R 17b , R 18b , R 21 , R 22 , R 12b to R 15b , R 21b and R 22b , R 2a to R 9a , R 2b to R 5b and R 7b examples thereof include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a chlorine atom and a bromine atom.
  • M b + is Hydron or Li +, Na +, 1 valent metal ions K + and the like, preferably a divalent or higher valent metal cation, more preferably Hydron or divalent or higher valent metal cation More preferred is hydrone.
  • the metal cation having a valence of 2 or more include cations of metals in groups 2 to 15 of the periodic table of elements, and preferably Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Cd 2+ , Ni 2+.
  • Divalent metal cations such as Zn 2+ , Cu 2+ , Hg 2+ , Fe 2+ , Co 2+ , Sn 2+ , Pb 2+ and Mn 2+ ; trivalent metal cations such as Al 3+ , Fe 3+ and Cr 3+ ;
  • Examples include tetravalent metal cations such as Sn 4+ , Mn 4+ , and Ce 4+ , and more preferably Mg 2+ , 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 4+ and Mn 4+ and the like, more preferably Mg 2+, Ca 2+, Sr 2+ , Ba 2 , Zn 2+, Cu 2+, Fe 2+, Mn 2+, Al 3+, Fe 3+, Cr 3+ and Mn 4+ and the like
  • A is preferably an integer of 0 to 10, more preferably an integer of 0 to 5, and further preferably an integer of 0 or 2 to 4.
  • R 1 to R 6 , R 21 , R 22 , R na1 , R na2 , M b + and a are preferably as follows: .
  • R 1 is preferably a hydrogen atom.
  • R 2 to R 5 are each 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; a hydrogen atom contained in an alkyl group such as a trifluoromethyl group A group in which all of the above are replaced by a fluorine atom; a halogen atom such as a chlorine atom or a bromine atom; a nitro group; —CO 2 — ; —S (O) 2 O — or the like.
  • R 6 is preferably —CO—OR na1 , —CO—NH 2 , —CO—NH (R na1 ), —CO—N (R na1 ) 2 or —CO—R na1 .
  • R 21 and R 22 do not form a ring together with the carbon atom to which each is bonded, R 21 includes —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 are preferred, —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 is an optionally substituted hydrocarbon group having 1 to 40 carbon atom
  • R 6 and R 21 are preferably the same group.
  • 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 —CH 2 — contained in the hydrocarbon group and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR NA 10 - be replaced in Good.
  • —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —.
  • Specific examples and preferred examples of R na2 are the same as R na1. When two or more Rna2 exists, these may be the same and may differ.
  • R 21 and R 22 together with the carbon atom to which each is bonded form a ring, it is preferable to form the structure of group B, and to form the ring represented by formula (2a-x) Is more preferable.
  • R 23 and R 24 are preferably hydrogen atoms. It is also preferred that R 21 and R 22 do not form a ring.
  • R na1 and R na2 are alkyl groups having 1 to 10 carbon atoms such as methyl group, ethyl group and butyl group; aromatic hydrocarbon groups having 6 to 10 carbon atoms such as phenyl group, toluyl group and ethylphenyl group; Combination of chain hydrocarbon group such as benzyl group (also called phenylmethyl group), 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, phenylethyl group, phenylpropyl group and aromatic hydrocarbon group These groups are preferably a group having 7 to 15 carbon atoms; these groups may have —CO 2 — or —S (O) 2 O — , and a substituent such as a methoxy group An alkoxy group having 1 to 10 carbon atoms such as a methoxycarbonyl group; a sulfamoyl group; a hydroxy group; a halogen atom such as a chlorine
  • M b + is a kind selected from the group consisting of hydrone, Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Zn 2+ , Cu 2+ , Fe 2+ , Mn 2+ , Al 3+ , Fe 3+ , Cr 3+ and Mn 4+.
  • hydrone is more preferable.
  • a is preferably an integer of 1 to 10, more preferably an integer of 1 to 5. It is also preferable that a is 0.
  • R 11b to R 16b , R 21b to R 24b , R nb1 , R nb5 are the following: It is preferable that it is as follows.
  • R 11b is preferably a hydrogen atom.
  • R 16b is preferably —CO—OR nb1 , —CO—NH 2 , —CO—NH (R nb1 ), —CO—N (R nb1 ) 2 or —CO—R nb1 .
  • R 21b includes -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 are preferred, —CO—OR nb5 , —CO—NH 2 , —CO—NH ( R nb5 ), —CO—N (R nb5 ) 2 or —CO—R nb5 is more preferred, and R 22b represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a substituent.
  • R 16b and R 21b are preferably the same group.
  • 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 —CH 2 — contained in the hydrocarbon group and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR NB 10 - be replaced in Good.
  • R nb5 is the same as R nb1. When two or more Rnb5 exists, these may be the same and may differ.
  • R 21b and R 22b together with the carbon atom to which each is bonded form a ring it is preferable to form the structure of group C and form the ring represented by formula (2a-xb) Is more preferable.
  • R 23b and R 24b are preferably hydrogen atoms. It is also preferred that R 21b and R 22b do not form a ring.
  • R nb1 and R nb5 are alkyl groups having 1 to 10 carbon atoms such as methyl group, ethyl group and butyl group; aromatic hydrocarbon groups having 6 to 10 carbon atoms such as phenyl group, toluyl group and ethylphenyl group; A group comprising a chain hydrocarbon group such as phenylmethyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, phenylethyl group, phenylpropyl group, etc., and an aromatic hydrocarbon group.
  • These groups are preferably substituted with a C 1-10 alkoxy group such as a methoxy group; a C 1-10 hydrocarbon group such as a methoxycarbonyl group as a substituent.
  • a C 1-10 alkoxy group such as a methoxy group
  • a C 1-10 hydrocarbon group such as a methoxycarbonyl group as a substituent.
  • An oxycarbonyl group; a sulfamoyl group; a hydroxy group; and a halogen atom such as a chlorine atom.
  • R 1a to R 9a , R na4 , M b + and a are as follows: Is preferred.
  • R 1a is preferably a hydrogen atom.
  • R 2a to R 5a are each 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; a hydrogen atom contained in an alkyl group such as a trifluoromethyl group group all is replaced with a fluorine atom; a chlorine atom, a halogen atom such as a bromine atom; a nitro group; -CO 2 -; -S (O ) 2 O - , and the like are preferable.
  • R 6a includes —COO ⁇ , —CO—OR na 4 , —CO—NH 2 , —CO—NH (R na4 ), —CO—N (R na4 ) 2 , —CO—H, —CO—R na 4 Or —S (O) 2 —R na4 is preferred, —CO—OR na4 , —CO—NH 2 , —CO—NH (R na4 ), —CO—N (R na4 ) 2 or —CO—R na4 is More preferred.
  • R na4 represents an optionally substituted hydrocarbon group having 1 to 35 carbon atoms or an optionally substituted heterocyclic group, and —CH 2 — contained in the hydrocarbon group. and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR NA 10 - be replaced in Good. However, —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —. Specific examples and preferred examples of R na4 is the same as R na1. When two or more Rna2 exists, these may be the same and may differ.
  • an optionally substituted hydrocarbon group having 1 to 40 carbon atoms an optionally substituted heterocyclic group, a hydrogen atom, a halogen atom, a cyano group, a nitro group, — CO 2 — or —S (O) 2 O — is preferable, and a cyano group is more preferable.
  • R 8a includes —COO ⁇ , —CO—OR na4 , —CO—NH 2 , —CO—NH ( R na4 ), —CO—N (R na4 ) 2 , —CO—H, —CO—R na4 or —S (O) 2 —R na4 are preferred, —CO—OR na4 , —CO—NH 2 , — CO—NH (R na4 ), —CO—N (R na4 ) 2 or —CO—R na4 is more preferable, and R 7a is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent.
  • R 6a and R 8a are preferably the same group.
  • R 8a and R 9a together with the carbon atom to which each is bonded form a ring it is preferable to form a structure of group A, and it is preferable to form a ring represented by the formula (QQ18) .
  • R 25 and R 26 are preferably a hydrogen atom. It is also preferred that R 8a and R 9a do not form a ring.
  • R na4 includes 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 phenylmethyl group A group comprising a combination of a chain hydrocarbon group such as 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, phenylethyl group, phenylpropyl group and an aromatic hydrocarbon group, having 7 to 7 carbon atoms And the like.
  • These groups may have —CO 2 — or —S (O) 2 O — , and the substituent may be an alkoxy group having 1 to 10 carbon atoms such as a methoxy group.
  • a halogen atom such as a chlorine atom; a sulfamoyl group; hydroxy group oxycarbonyl group having a hydrocarbon group bonded having 1 to 10 carbon atoms such as a methoxycarbonyl group may have, -CO 2 - -S (O) 2 O - preferably it has.
  • M b + is a kind selected from the group consisting of hydrone, Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Zn 2+ , Cu 2+ , Fe 2+ , Mn 2+ , Al 3+ , Fe 3+ , Cr 3+ and Mn 4+.
  • hydrone is more preferable.
  • a is preferably an integer of 1 to 5.
  • R 1b to R 7b , R 17b to R 18b , R nb1 , R nb6 are the following: It is preferable that it is as follows.
  • R 1b is preferably a hydrogen atom.
  • R 6b is preferably —CO—OR nb1 , —CO—NH 2 , —CO—NH (R nb1 ), —CO—N (R nb1 ) 2 or —CO—R nb1 .
  • R 7b includes 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) 2 O — is preferable, and a cyano group is more preferable.
  • R 17b includes —CO—OR nb6 , —CO—NH 2 , —CO—NH (R nb6 ), —CO—N (R nb6 ) 2 , —CO—H, —CO—R nb6 or —S (O) 2 —R nb6 are preferred, —CO—OR nb6 , —CO—NH 2 , —CO—NH ( R nb6 ), —CO—N (R nb6 ) 2 or —CO—R nb6 is more preferred, and R 18b is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a substituent.
  • R 6b and R 17b are preferably the same group.
  • R nb6 represents an optionally substituted hydrocarbon group having 1 to 35 carbon atoms or an optionally substituted heterocyclic group, and —CH 2 — contained in the hydrocarbon group. and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR NB 10 - be replaced in Good.
  • R nb6 is the same as R nb1. When two or more Rnb6 exists, these may be the same and may differ.
  • R 17b and R 18b together with the carbon atom to which each is bonded form a ring those that form the structure of group C are preferred, and more preferably form the ring represented by formula (2a) preferable.
  • R 19b and R 20b are preferably hydrogen atoms. It is also preferred that R 17b and R 18b do not form a ring.
  • R nb1 and R nb6 are alkyl groups having 1 to 10 carbon atoms such as methyl group, ethyl group and butyl group; aromatic hydrocarbon groups having 6 to 10 carbon atoms such as phenyl group, toluyl group and ethylphenyl group; A group comprising a chain hydrocarbon group such as phenylmethyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, phenylethyl group, phenylpropyl group, etc., and an aromatic hydrocarbon group.
  • These groups are preferably substituted with a C 1-10 alkoxy group such as a methoxy group; a C 1-10 hydrocarbon group such as a methoxycarbonyl group as a substituent.
  • a C 1-10 alkoxy group such as a methoxy group
  • a C 1-10 hydrocarbon group such as a methoxycarbonyl group as a substituent.
  • An oxycarbonyl group; a sulfamoyl group; a hydroxy group; and a halogen atom such as a chlorine atom.
  • -CO-OR na1 , -CO-OR na2 , -CO-OR nb1 , -CO-OR nb5 , -CO-OR na4 , -CO-OR nb6 are alkyl groups such as methoxycarbonyl group and ethoxycarbonyl group.
  • An oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms (particularly an alkyl group) is bonded is preferred.
  • —CO—R na1 , —CO—R na2 , —CO—R nb1 , —CO—R nb5 , —CO—R na4 , —CO—R nb6 are aromatics having 6 to 10 carbon atoms such as a benzoyl group.
  • a carbonyl group to which an alkyl group having 1 to 10 carbon atoms to which an aromatic ring is bonded is bonded is preferred.
  • R na1, R na2, R na4 is, -CO 2 - or -S (O) 2 O -
  • R na1, R na2, R na4 is, -CO 2 - or -S (O) 2 O -
  • an alkoxy group having 1 to 10 carbon atoms such as a methoxy group
  • a sulfamoyl group such as a hydroxy group
  • a halogen atom such as a chlorine atom
  • a carbon atom such as a carbonyl group to which the aromatic ring is bonded
  • a carbonyl group to which an alkyl group to which an aromatic ring is bonded is bonded to —CO 2 -; -S (O) 2 O -
  • -CO-NH (R na1), - CO-NH (R na2), - CO-NH (R nb1), - CO-NH (R nb5), - CO-NH (R na4), - CO-NH ( R nb6 ) is preferably an aminocarbonyl group to which an alkyl group having 1 to 10 carbon atoms such as a methylaminocarbonyl group is bonded.
  • —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 nb6 ) 2 is preferably an aminocarbonyl group in which two alkyl groups having 1 to 10 carbon atoms such as a dimethylaminocarbonyl group are bonded.
  • (P), L 4 and L 5 independently of one another, represents a divalent hydrocarbon group having 1 to 10 carbon atoms, the hydrocarbon group is -CH 2 - if it contains, the -CH 2 - May be replaced by -NH-.
  • R p represents a hydrogen atom or a substituent, and p represents any integer of 1 to 4.
  • the wavy line represents the E body, the Z body, or both.
  • Examples of the divalent hydrocarbon group include an alkylene group and an arylene group (for example, a phenylene group).
  • Another more preferable example of the compound (B) represented by the formula (I) is a compound in which two COOH groups are replaced by —S (O) 2 OH groups in the formula (P).
  • Specific examples of the compound represented by formula (I), formula (IA), formula (IB) or formula (IIB) include, for example, in the compound represented by the following formula (Ia), a combination of R 31 , L 1 , L 2 , R 32 , B 1 B 2 , n, m and M b + is any of Tables 1 to 4 A compound, and Examples of the compound represented by the following formula (Ib) include compounds in which the combination of R 33 , L 3 , B 1 B 2 , n, m and M b + is any one of those shown in Tables 5 to 6. Note that R 31 , R 32 , and R 33 each represent a partial structure represented by the formula (HH1) to the formula (HH18). B 1 B 2 represents any one of the partial structures represented by the formulas (BB1) to (BB9).
  • R 1 to R 7 , X, M b + , a, m, and n represent the same meaning as described above.
  • R 41 and R 42 each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
  • M 1 and M 2 represent an alkali metal atom.
  • LG 1 and LG 2 each independently represent a halogen atom, a methanesulfonyloxy group, a chloromethylsulfonyloxy group, a toluenesulfonyloxy group, or a trifluoromethanesulfonyloxy group.
  • M represents a metal atom.
  • 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.
  • 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) is usually 0.1 mol or more and 10 mol or less, preferably 0.2 mol, relative to 1 mol of the phthalonitrile compound represented by the formula (pt1).
  • the number of moles is 5 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles.
  • the total amount of compound (pt3) and compound (pt4) used is usually 2 mol or more and 20 mol or less, preferably 2 mol or more and 10 mol, per 1 mol of the phthalonitrile compound represented by formula (pt1).
  • the amount is 2 mol or less, more preferably 2 mol or more and 6 mol or less, and further preferably 2 mol or more and 4 mol or less.
  • the compound (pt3) and the compound (pt4) may be the same compound.
  • acids include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid;
  • carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid And carboxylic acid, more preferably acetic acid.
  • the amount of the acid used is usually 1 mol or more and 20 mol or less, preferably 1 mol or more and 10 mol or less, more preferably 1 mol or more and 8 mol or less, more preferably 1 mol per mol of the phthalonitrile compound. Is 1 mol or more and 6 mol or less.
  • solvents include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; 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 Solvent; sulfoxide solvents such as dimethyl sulfoxide are mentioned, preferably water, nitrile solvent, alcohol solvent, ether solvent, ket
  • Cited 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 dimethyl sulfoxide More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, methylene chloride, chloroform, N, N-dimethylformaldehyde, N-dimethyla Examples
  • the reaction temperature of the phthalonitrile compound, alkoxide compound, compound (pt3) and compound (pt4) is usually 0 ° C. or higher and 200 ° C. or lower, preferably 0 ° C. or higher and 100 ° C. or lower, more preferably 0 ° C. or higher and 50 ° C. or lower. It is as follows.
  • the reaction time is usually 0.5 hours or more and 300 hours or less.
  • the compound (B) represented by the formula (I) in which R 1 is not a hydrogen atom can be obtained.
  • the amount of compound (pt6) to be used is generally 1 mol to 10 mol, preferably 1 mol to 5 mol, per 1 mol of compound (B) represented by formula (I) wherein R 1 is a hydrogen atom. It is 1 mol or less, More preferably, it is 1 mol or more and 3 mol or less, More preferably, it is 1 mol or more and 2 mol or less.
  • the base When reacting the compound (pt6), it is preferable to coexist with a base.
  • the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, pyridine and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide; butyllithium Organic metal compounds such as tert-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 mol or more and 10 mol or less, preferably 1 mol or more and 5 mol or less, relative to 1 mol of the compound (B) represented by the formula (I) in which R 1 is a hydrogen atom. More preferably, it is 1 mol or more and 3 mol or less, More preferably, it is 1 mol or more and 2 mol or less.
  • the reaction of the 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 part by mass or more and 1000 parts by mass or less with respect to 1 part by mass of the compound (B) represented by the formula (I) in which R 1 is not a hydrogen atom.
  • the reaction temperature with the compound (pt6) is usually ⁇ 90 ° C. or higher and 200 ° C. or lower, preferably ⁇ 80 ° C. or higher and 100 ° C. or lower, more preferably 0 ° C. or higher and 50 ° C. or lower.
  • the reaction time is usually 0.5 hours or more and 300 hours or less.
  • the compound (B) represented by the formula (I) does not have a sulfo group
  • the compound (B) represented by the formula (I) is reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid.
  • a sulfo group can be introduced.
  • the amount of SO 3 used in the fuming sulfuric acid is usually 1 mol or more and 50 mol or less, preferably 5 mol or more and 40 mol or less, based on 1 mol of the compound (B) represented by the formula (I). Preferably they are 5 mol or more and 30 mol or less, More preferably, they are 5 mol or more and 25 mol or less.
  • the amount of sulfuric acid used in the fuming sulfuric acid is usually 1 mol to 200 mol, preferably 10 mol to 100 mol, and more preferably 1 mol of the compound (B) represented by the formula (I). Is from 10 mol to 75 mol, more preferably from 10 mol to 50 mol.
  • the amount of chlorosulfonic acid used is usually 1 mol or more and 500 mol or less, preferably 10 mol or more and 300 mol or less, more preferably 10 mol, per 1 mol of the compound (B) represented by the formula (I). It is more than mol and 200 mol or less, More preferably, it is 10 mol or more and 150 mol or less.
  • the reaction temperature of sulfonation is usually ⁇ 20 ° C. or higher and 200 ° C. or lower, preferably ⁇ 10 ° C. or higher and 100 ° C. or lower, more preferably 0 ° C. or higher and 50 ° C. or lower.
  • the reaction time is usually 0.5 hours or more and 300 hours or less.
  • the compound (B) represented by the formula (I) has a carboxy group or a sulfo group
  • the compound (pt7) and the compound (pt8) are reacted with each other to represent the compound represented by the formula (I) containing the metal ion M b +.
  • Compound (B) may be produced.
  • the method for taking out the compound (B) represented by the formula (I) from the reaction mixture is not particularly limited, and it can be taken out by various known methods.
  • the compound (B) represented by the formula (I) can be taken out by filtering the reaction mixture. Further, after filtration, the obtained residue may be washed with a solvent. Further, after filtration, column chromatography, recrystallization, or sublimation purification may be performed.
  • I. Pigment Yellow 138 (A) and a compound (B) represented by the formula (I) are included.
  • the colorant dispersion containing the co-dispersion for example, C.I. I. Pigment Yellow 138 (A) dispersion and a compound (B) dispersion represented by formula (I) are prepared separately, and compared with a colorant dispersion obtained by mixing them. Can be improved.
  • a main component means a component with the highest content rate (mass basis) among the colorants contained in a colorant dispersion.
  • the colorant is a general term for pigments represented by pigments and dyes.
  • the co-dispersion is C.I. I.
  • the compound (B) represented by the formula (I) together with CI Pigment Yellow 138 (A) is dispersed in a solvent in the presence of a dispersant as necessary or in the presence of a resin as necessary.
  • a dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more.
  • the resin may be selected from the resin (D) described later.
  • the solvent may be selected from the solvent (G) described later.
  • the co-dispersion is, for example, C.I. I.
  • Pigment Yellow 138 (A) and the compound (B) represented by the formula (I) are mixed with a part or all of the solvent (G), and optionally in the presence of a dispersant, or further as necessary.
  • the resin (D) can be prepared by dispersing it using a bead mill or the like until the average particle diameter of the colorant is about 0.2 ⁇ m or less in the presence of part or all of the resin (D).
  • the amount used is preferably 1% by mass or more and 100% by mass or less, and more preferably 5% by mass or more and 80% by mass or less, with respect to the total amount of the colorant.
  • the amount of the dispersant used is in the above range, a co-dispersed product in a uniform dispersion state tends to be obtained.
  • the usage-amount is with respect to the total amount of a coloring agent, Preferably it is 1 to 100 mass%, More preferably, it is 5 to 80 mass%.
  • the amount of the resin used is in the above range, a co-dispersed material in a uniform dispersion state tends to be obtained.
  • the content of Pigment Yellow 138 (A) is C.I. I. Pigment Yellow 138 (A) and Compound (B) represented by Formula (I) in a total amount of 100 parts by mass, preferably 50.1 parts by mass to 99.9 parts by mass, more preferably 60 parts by mass. It is 99 mass parts or less, More preferably, it is 85 mass parts or more and 99 mass parts or less.
  • the content of the compound (B) represented by the formula (I) is C.I. I.
  • the co-dispersion and the colorant dispersion are respectively C.I. I.
  • Other components than the pigment yellow 138 (A) and the compound (B) represented by the formula (I) can be included.
  • Other components include C.I. I. Pigment Yellow 138 (A) and other colorants (pigments, dyes) other than the compound (B) represented by Formula (I), solvents, dispersants, resins, aliphatic carboxylic acid metal salts (C), and the like. It is done.
  • the aliphatic carboxylic acid metal salt (C) will be described later.
  • Each of the co-dispersion and the colorant dispersion may contain only one type of other component, or may contain two or more types.
  • pigments are not particularly limited, and publicly known pigments can be used. Examples thereof include pigments classified as pigments according to the color index (published by The Society of Dyers and Colorists). As a pigment, for example, C. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 139, 147, Yellow pigments such as 148, 150, 153, 154, 166, 173, 185, 194, 214; C. I. Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; C. I.
  • Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265; C. I. Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60; C. I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; C. I. Green pigments such as CI Pigment Green 7, 36, 58, 59; C. I. Brown pigments such as CI Pigment Brown 23 and 25; C. I. Black pigments such as CI Pigment Black 1 and 7; Etc.
  • Blue pigments such as CI Pigment Blue 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265
  • pigments are C.I. I. Pigment Yellow 138 (A) and the compound (B) represented by the formula (I) may be co-dispersed in the co-dispersion, or C.I. I. Pigment Yellow 138 (A) and the co-dispersion containing the compound (B) represented by the formula (I) may be added to the colorant dispersion.
  • a well-known dye can be used, For example, a solvent dye, an acid dye, a direct dye, a mordant dye etc. are mentioned.
  • the dye include known dyes described in Color Index (published by The Society of Dyers and Colorists) and dyeing notes (Color Dyeing).
  • the dyes include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, Examples include styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Of these, organic solvent-soluble dyes are preferred.
  • the dye may be contained in the co-dispersion, or may be added to the co-dispersion and contained in the colorant dispersion.
  • Resin may be selected from the resin (D) described below.
  • the solvent may be selected from the solvent (G) described later.
  • the total content of the pigment yellow 138 (A) and the compound (B) represented by the formula (I) is preferably 5 parts by mass or more in 100 parts by mass of the colorant contained in the co-dispersion or the colorant dispersion. More preferably 10 parts by mass or more, still more preferably 30 parts by mass or more, still more preferably 50 parts by mass or more, particularly preferably 80 parts by mass or more, and most preferably 90 parts by mass or more. It is.
  • the total content may be 100 parts by mass in 100 parts by mass of the colorant contained in the co-dispersion or the colorant dispersion.
  • the total content of Pigment Yellow 138 (A) and the compound (B) represented by the formula (I) is preferably 10 parts by mass in the total amount of solids contained in the co-dispersion or the colorant dispersion. It is 90 parts by mass or less, more preferably 15 parts by mass or more and 80 parts by mass or less, and further preferably 20 parts by mass or more and 70 parts by mass or less.
  • the “total amount of solids” contained in the co-dispersion, colorant dispersion or colored curable resin composition refers to the total amount of the co-dispersion, colorant dispersion or colored curable resin composition. The amount excluding the solvent content.
  • the total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography, for example.
  • Aliphatic carboxylic acid metal salt (C) The colorant dispersion may contain an aliphatic carboxylic acid metal salt (C) as the other component. Further inclusion of the aliphatic carboxylic acid metal salt (C) is advantageous for improving the contrast.
  • the aliphatic carboxylic acid metal salt (C) may be contained in the co-dispersion, or may be added to the co-dispersion and contained in the colorant dispersion.
  • the aliphatic carboxylic acid metal salt (C) is a salt composed of a metal cation and an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms having a hydroxy group.
  • the aliphatic carboxylic acid having 1 to 40 carbon atoms having a hydroxy group is also referred to as “aliphatic carboxylic acid (X)”.
  • aliphatic carboxylic acid means a carboxylic acid having no aromatic ring.
  • the colored curable resin composition of the present invention may contain only one type of aliphatic carboxylic acid metal salt (C), or may contain two or more types.
  • the aliphatic carboxylic acid (X) has 1 to 40 carbon atoms including carbon of the carboxy group, and may be linear, branched or cyclic. It may be a combination of two or more structures selected from the group consisting of a linear structure, a branched chain structure and a cyclic structure.
  • the aliphatic carboxylic acid (X) may contain an unsaturated bond.
  • the aliphatic carboxylic acid (X) has one or more hydroxy groups in the molecule.
  • the aliphatic carboxylic acid (X) has one or more carboxy groups in the molecule.
  • the number of carboxy groups is usually 10 or less.
  • the carbon number of the aliphatic carboxylic acid (X) is from 1 to 40, preferably from 10 to 36, more preferably from 12 to 24, from the viewpoint of enhancing the contrast.
  • the aliphatic carboxylic acid metal salt (C) only needs to have at least one anion of the aliphatic carboxylic acid (X).
  • the aliphatic carboxylic acid metal salt (C) has two or more kinds of anions of the aliphatic carboxylic acid (X). It may have an anion of aliphatic carboxylic acid (X) and an anion other than the anion of aliphatic carboxylic acid (X).
  • the other anion is not particularly limited and may be a halogen ion, a nitrate ion, a sulfate ion, or the like, but is preferably an anion of an aliphatic carboxylic acid other than the aliphatic carboxylic acid (X).
  • the aliphatic carboxylic acid other than the aliphatic carboxylic acid (X) means an aliphatic carboxylic acid having no hydroxy group.
  • the aliphatic carboxylic acid (X) is the same as the aliphatic carboxylic acid (X) except having no hydroxy group.
  • the anion contained in the aliphatic carboxylic acid metal salt (C) is preferably composed only of the anion of the aliphatic carboxylic acid (X).
  • the metal cation possessed by the aliphatic carboxylic acid metal salt (C) is preferably a metal cation having a valence of not less than 10 and not more than 10 from the viewpoint of enhancing contrast.
  • Examples of the bivalent or higher metal cation include cations of metals belonging to Groups 2 to 15 of the periodic table of elements.
  • the metal cation is preferably a divalent to hexavalent metal cation.
  • Metal cations are More preferably, divalent such as Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Cd 2+ , Ni 2+ , Zn 2+ , Cu 2+ , Hg 2+ , Fe 2+ , Co 2+ , Sn 2+ , Pb 2+ and Mn 2+.
  • the aliphatic carboxylic acid metal salt (C) may be a compound represented by the following formula (Aa).
  • D represents an aliphatic hydrocarbon having a hydroxy group.
  • a represents an integer of 1 to 10, and preferably an integer of 1 to 3. When a plurality are present, they may be the same as or different from each other.
  • the carbon number + a of D is an integer of 1 to 40.
  • b represents any integer of 1 or more. When b represents any integer of 2 or more, “[D]-(CO 2 ⁇ ) a ” may be the same as or different from each other.
  • J k- represents an anion other than “[D]-(CO 2 ⁇ ) a ”.
  • k represents an integer of 1 to 10, preferably an integer of 1 to 6.
  • m represents any integer of 0 or more.
  • a c + represents a c-valent metal cation, and specific examples thereof are as described above.
  • c represents an integer of 2 to 10, preferably an integer of 2 to 6.
  • d represents any integer of 1 or more.
  • a c + may be the same as or different from each other.
  • the total valence of Is equal to the valence of. ]
  • the aliphatic carboxylic acid metal salt (C) is obtained, for example, as a precipitate generated by dissolving the aliphatic carboxylic acid (X) in an alkaline aqueous solution and then adding a salt having a metal cation (such as a halide). be able to.
  • the obtained aliphatic carboxylic acid metal salt (C) may be subjected to purification treatment such as washing, if necessary.
  • M, L, p and q are each a compound represented by the following [Table A], [ in the compounds AA1 ⁇ AA22 Table a], Mg 2+ instead of M is Fe 2+, Ca 2+, Sr 2+ , Ba 2+, Cd 2+, Ni 2+, Zn 2+, Cu 2+, Hg 2+, Co 2+, Sn 2+, A compound represented by Pb 2+ or Mn 2+ , a compound represented by [Table B], a compound AA23 to AA44 of [Table B], wherein M is Al 3+ , Co 3+ or Cr 3+ instead of Fe 3+ , And compounds represented by [Table C].
  • Examples of the aliphatic carboxylic acid metal salt (C) having an anion of the aliphatic carboxylic acid (X) and an anion other than the anion of the aliphatic carboxylic acid (X) include, for example, a salt represented by the following formula: Is mentioned.
  • the content of the aliphatic carboxylic acid metal salt (C) is the solid content contained in the co-dispersion or the colorant dispersion.
  • the total amount is 100 parts by mass, preferably 0.01 parts by mass or more and 25 parts by mass or less, more preferably 0.1 parts by mass or more and 20 parts by mass or less, and further preferably 0.2 parts by mass or more and 15 parts by mass or less. Especially preferably, it is 0.3 mass part or more and 10 mass parts or less.
  • the content of the aliphatic carboxylic acid metal salt (C) is C.I. I.
  • they are 0.1 mass part or more and 20 mass parts or less with respect to 100 mass parts of total amounts of the compound (B) represented by pigment yellow 138 (A) and Formula (I), More preferably, it is 0.3. It is not less than 15 parts by mass and more preferably not less than 0.5 parts by mass and not more than 13 parts by mass.
  • the colored curable resin composition contains the colorant dispersion and the resin (D).
  • the colored curable resin composition preferably further includes a polymerizable compound (E) and a polymerization initiator (F), and further includes a polymerizable compound (E), a polymerization initiator (F), and a solvent (G). Is more preferable.
  • the colored curable resin composition may further contain a polymerization initiation assistant (F1) and / or a leveling agent (H). According to the said colored curable resin composition, the color filter formed from it and the contrast of a display apparatus using the same can be made favorable.
  • the compound illustrated as each component can be used individually or in combination of multiple types.
  • the colorant dispersion contains the content of the colorant contained therein (or CI Pigment Yellow 138 (A) and the formula
  • the total content of the compound (B) represented by (I)) is preferably 100 parts by mass or more and more preferably 90 parts by mass or less, more preferably 100 parts by mass or less, more preferably 100 parts by mass of the solid content of the colored curable resin composition. It is contained in the colored curable resin composition so as to be 0.5 parts by mass or more and 80 parts by mass or less, more preferably 1 part by mass or more and 70 parts by mass or less.
  • the resin (D) is not particularly limited, but is preferably an alkali-soluble resin, and is at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (hereinafter referred to as “(a)”).
  • the resin (D) further includes a structural unit derived from the monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”).
  • Examples of (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and succinic acid mono [2- (meth) acryloyloxyethyl]. Among them, acrylic acid, methacrylic acid, and maleic anhydride are preferable.
  • (B) is a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and a (meth) acryloyloxy group.
  • (meth) acrylic acid represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as “(meth) acryloyl” and “(meth) acrylate” have the same meaning.
  • Examples of (b) include glycidyl (meth) acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl (meth) acrylate, 3-ethyl-3- (Meth) acryloyloxymethyloxetane, tetrahydrofurfuryl (meth) acrylate, and the like can be mentioned.
  • Examples of (c) include methyl (meth) acrylate, butyl (meth) acrylate cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, and tricyclo [5.2.1.0 2,6 ] decane-8.
  • a resin having a structural unit having an ethylenically unsaturated bond in the side chain is obtained by adding (b) to a copolymer of (a) and (c) or a copolymer of (b) and (c) It can be produced by adding (a) to.
  • the resin may be a resin obtained by adding (a) to a copolymer of (b) and (c) and further reacting with a carboxylic acid anhydride.
  • the polystyrene equivalent weight average molecular weight of the resin (D) is preferably 3000 or more and 100,000 or less, more preferably 5000 or more and 50000 or less, and further preferably 5000 or more and 30000 or less.
  • the dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (D) is preferably 1.1 or more and 6 or less, more preferably 1.2 or more and 4 or less.
  • the acid value of the resin (D) is preferably 20 mg-KOH / g or more and 170 mg-KOH / g or less, more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, more preferably in terms of solid content. It is 40 mg-KOH / g or more and 135 mg-KOH / g or less.
  • the acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (D), and can be determined by titration with an aqueous potassium hydroxide solution, for example.
  • the content of the resin (D) is preferably 7 parts by mass or more and 65 parts by mass or less, more preferably 13 parts by mass or more and 60 parts by mass or less, in a total amount of 100 parts by mass of the solid content of the colored curable resin composition. Yes, more preferably 17 parts by mass or more and 55 parts by mass or less.
  • the polymerizable compound (E) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (F), and examples thereof include a compound having a polymerizable ethylenically unsaturated bond. Is a (meth) acrylic acid ester compound.
  • the polymerizable compound (E) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds.
  • examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa ( And (meth) acrylate.
  • the weight average molecular weight of the polymerizable compound (E) is preferably 150 or more and 2900 or less, more preferably 250 or more and 1500 or less.
  • the content of the polymerizable compound (E) is preferably 7 parts by weight or more and 65 parts by weight or less, more preferably 13 parts by weight or more and 60 parts by weight or less, in a total amount of 100 parts by weight of the solid content of the colored curable resin composition. Or less, more preferably 15 parts by mass or more and 55 parts by mass or less.
  • the polymerization initiator (F) is not particularly limited as long as it is a compound capable of generating an active radical, an acid or the like by the action of light or heat and starting polymerization, and a known polymerization initiator can be used.
  • polymerization initiators that generate active radicals include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) ) Octane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine, 2-methyl-2-morpholino-1- ( 4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,4-bis (trichloromethyl) ) -6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoy Diphenyl phosphine oxide, 2,2'-bis (2-ch)
  • the content of the polymerization initiator (F) is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 100 parts by mass of the total amount of the resin (D) and the polymerizable compound (E). 1 to 20 parts by mass.
  • the content of the polymerization initiator (F) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, so the productivity of the color filter is improved.
  • the polymerization initiation assistant (F1) is a compound or a sensitizer used for accelerating the polymerization of the polymerizable compound (E) that has been polymerized by the polymerization initiator (F).
  • the polymerization initiation assistant (F1) is contained, it is usually used in combination with the polymerization initiator (F).
  • polymerization initiation assistant (F1), 4,4′-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4′-bis (diethylamino) benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone N-phenylglycine and the like.
  • the content thereof is preferably 0.1 to 30 parts by mass, more preferably 100 parts by mass of the total amount of the resin (D) and the polymerizable compound (F). 1 to 20 parts by mass.
  • the amount of the polymerization initiation assistant (F1) is within this range, a colored pattern can be formed with higher sensitivity and the productivity of the color filter tends to be improved.
  • a solvent (G) is not specifically limited, The solvent normally used in the said field
  • ester solvents solvents containing —COO— in the molecule and not containing —O—
  • ether solvents solvents containing —O— in the molecule and not containing —COO—
  • ether ester solvents intramolecular Solvent containing -COO- and -O-
  • ketone solvent solvent containing -CO- in the molecule and not containing -COO-
  • alcohol solvent containing OH in the molecule, -O-,- Solvent containing no CO- and -COO-
  • aromatic hydrocarbon solvent amide solvent, dimethyl sulfoxide and the like.
  • Ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate and ⁇ -butyrolactone (within the molecule -COO- Containing -O--free solvent); Ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether (solvents containing —O— in the molecule and not —COO—) ); Ether ester solvents such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybuty
  • solvents containing OH in the molecule but not -O-, -CO- and -COO- solvents containing OH in the molecule but not -O-, -CO- and -COO-
  • amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone
  • solvent (G) propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate and 4-hydroxy-4-methyl-2-pentanone are more preferable.
  • the content of the solvent (G) is preferably 70 parts by mass or more and 95 parts by mass or less, more preferably 75 parts by mass or more, in a total amount of 100 parts by mass of the colored curable resin composition. 92 parts by mass or less.
  • the total amount of the solid content of the colored curable resin composition is preferably 5 parts by mass or more and 30 parts by mass or less, more preferably 8 parts by mass or more and 25 parts by mass in the total amount of the colored curable resin composition of 100 parts by mass. It is as follows. When the content of the solvent (G) is within the above range, the flatness at the time of coating is good, and when the color filter is formed, the color density does not become insufficient and the display characteristics tend to be good. .
  • Leveling agent (H) examples include silicone surfactants, fluorine surfactants, and silicone surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
  • silicone surfactant examples include a surfactant having a siloxane bond in the molecule.
  • Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade names: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (made by Momentive Performance Materials Japan GK) .
  • fluorosurfactant examples include surfactants having a fluorocarbon chain in the molecule.
  • Florard registered trademark
  • FC430 FC431
  • MegaFac registered trademark
  • F142D F171, F172, F173, F177, F183, F183, F554, R30
  • RS-718-K manufactured by DIC Corporation
  • EFTOP registered trademark
  • EF301 EF301
  • EF303 EF351
  • EF352 manufactured by Mitsubishi Materials Electronic Chemicals
  • Surflon registered trademark
  • SC101 SC105
  • SC105 Asahi Glass Co., Ltd.
  • E5844 Daikin Fine Chemical Laboratory Co., Ltd.
  • silicone surfactant having a fluorine atom examples include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule.
  • Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation), and the like can be given.
  • the content of the leveling agent (F) is preferably 1001 parts by mass or more and 0.2 parts by mass or less, more preferably in a total amount of 100 parts by mass of the colored curable resin composition. Preferably they are 0.002 mass part or more and 0.1 mass part or less. This content does not include the content of the dispersant.
  • the content of the leveling agent (H) is in the above range, the flatness of the color filter can be improved.
  • the colored curable resin composition is known in the art as necessary, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, etc.
  • the additive may be included.
  • the additive may be contained in the colorant dispersion or co-dispersion.
  • the colored curable resin composition comprises a colorant dispersion, a resin (D), and a polymerizable compound (E) and a polymerization initiator (F) used as necessary.
  • Solvent (G) polymerization initiation assistant (F1), leveling agent (H) and other components can be mixed.
  • Examples of the method for producing a colored pattern from the colorant dispersion or the colored curable resin composition include a photolithographic method, an ink jet method, and a printing method. Of these, the photolithographic method is preferable.
  • the colorant dispersion or the colored curable resin composition contains the above-mentioned co-dispersion, a color filter having excellent contrast can be produced.
  • the color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors.
  • ⁇ Synthesis Example 1 Preparation of Compound (I)> 3 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 300 parts of methanol were mixed. While maintaining the temperature of the obtained mixture at 5 ° C. or lower, 2.71 parts of 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise over 30 minutes and stirred at 5 ° C. for 6 hours. did. While maintaining the temperature of the obtained mixture at 5 ° C. or lower, 14 parts of acetic acid was added.
  • the weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured using the GPC method under the following conditions. Apparatus; K2479 (manufactured by Shimadzu Corporation) Column; SHIMADZU Shim-pack GPC-80M Column temperature: 40 ° C Solvent; tetrahydrofuran (THF) Flow rate: 1.0 mL / min Detector; RI Standard material for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
  • the ratio (Mw / Mn) between the weight average molecular weight (Mw) in terms of polystyrene and the number average molecular weight (Mn) obtained above was defined as the dispersity.
  • Aliphatic carboxylic acid metal salt (C) Aliphatic carboxylic acid metal salt (C) obtained in Synthesis Example 4
  • Dispersant 1 Dispersant (DISPERBYK-111; manufactured by Big Chemie Japan Co., Ltd.)
  • PGMEA Propylene glycol monomethyl ether acetate
  • DAA Diacetone alcohol (4-hydroxy-4-methyl-2-pentanone)
  • polymerizable compound (E), the polymerization initiator (F), and the leveling agent (H) are as follows.
  • CT-1 manufactured by Aisaka Electric Co., Ltd., color / color difference meter BM-5A; manufactured by Topcon Co., Ltd., light source
  • F-10 polarizing film

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Abstract

The present invention addresses the problem of providing: a coloring agent dispersion containing C. I. pigment yellow 138, which is capable of forming a color filter that exhibits a good contrast; a coloring curable resin composition which contains this coloring agent dispersion; a color filter which is formed from this coloring agent dispersion or this coloring curable resin composition; and a display device which comprises this color filter. A coloring agent dispersion according to the present invention, which contains a co-dispersion of (A) C. I. pigment yellow 138 that serves as a main component and (B) a compound represented by formula (I), and a coloring curable resin composition which contains this coloring agent dispersion are able to provide a color filter that exhibits a good contrast and a display device which comprises this color filter.

Description

着色剤分散液、着色硬化性樹脂組成物、カラーフィルタ及び表示装置Colorant dispersion, colored curable resin composition, color filter, and display device
　本発明は、着色剤分散液、着色硬化性樹脂組成物、カラーフィルタ及び表示装置に関する。 The present invention relates to a colorant dispersion, a colored curable resin composition, a color filter, and a display device.
　着色硬化性樹脂組成物は、液晶表示装置、エレクトロルミネッセンス表示装置及びプラズマディスプレイ等の表示装置に使用されるカラーフィルタの製造に用いられている。カラーフィルタを用いた表示装置には、高いコントラストが要求される。 Colored curable resin compositions are used in the manufacture of color filters used in display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays. A display device using a color filter is required to have high contrast.
　特開２００２－１７９９７９号公報（特許文献１）には、表示装置のコントラストを改善するために、黄色顔料であるＣ．Ｉ．ピグメントイエロー１３８を含むカラーペーストにＣ．Ｉ．ピグメントイエロー１３８のスルホン化誘導体をさらに含有させることが記載されている。 Japanese Patent Laid-Open No. 2002-179979 (Patent Document 1) describes C.I. which is a yellow pigment in order to improve the contrast of a display device. I. Pigment Yellow 138 containing C.I. I. The inclusion of a sulfonated derivative of CI Pigment Yellow 138 is described.
特開２００２－１７９９７９号公報Japanese Patent Laid-Open No. 2002-179979
　本発明の目的は、Ｃ．Ｉ．ピグメントイエロー１３８を含む着色剤分散液であって、良好なコントラストを示すカラーフィルタを形成することができる着色剤分散液、該着色剤分散液を含む着色硬化性樹脂組成物、該着色剤分散液又は該着色硬化性樹脂組成物から形成されるカラーフィルタ、及び該カラーフィルタを含む表示装置を提供することにある。 The object of the present invention is C.I. I. A colorant dispersion containing Pigment Yellow 138, which can form a color filter exhibiting good contrast, a color curable resin composition containing the colorant dispersion, and the colorant dispersion Another object is to provide a color filter formed from the colored curable resin composition and a display device including the color filter.
　本発明は、以下に示す着色剤分散液、着色硬化性樹脂組成物、カラーフィルタ及び表示装置を提供する。
　［１］　主成分としてのＣ．Ｉ．ピグメントイエロー１３８（Ａ）と、式（Ｉ）で表される化合物（Ｂ）との共分散物を含む、着色剤分散液。 The present invention provides the following colorant dispersion, colored curable resin composition, color filter, and display device.
[1] C.I. I. A colorant dispersion containing a co-dispersion of CI Pigment Yellow 138 (A) and the compound (B) represented by the formula (I).
Figure JPOXMLDOC01-appb-I000006
Figure JPOXMLDOC01-appb-I000006
［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、０～１０のいずれかの整数である。
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－ＮＲｎａ－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－からなる群より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－ＮＲｎａ－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－からなる群より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からなる群より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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　Ｒｎａ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－からなる群より選ばれる少なくとも一種を有していてもよい。Ｒｎａが複数個存在する場合、これらは同一でもよく、異なっていてもよい。
　Ｍｂ＋は、ヒドロン又はｂ価の金属イオンを表す。Ｍｂ＋が複数個存在する場合、これらは同一でもよく、異なっていてもよい。Ｍｂ＋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、Ｍｂ＋の個数を表す。
　ｎは、ｎ＝ｂ×ｍ／ａの関係を満たす数である。 [In the formula (I),
a represents the total number of —CO 2 — and —S (O) 2 O — contained in the compound represented by the formula (I), and is an integer of 0 to 10.
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 which may have a substituent or a hydrogen atom, and —CH contained in the hydrocarbon group 2 - the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO -, - S (O) 2 - or -NR na - to have replaced May be. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 each independently 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, cyano. group, a nitro group, -CO 2 - or -S (O) 2 O - represents, -CH 2 - contained in the hydrocarbon group when including - and said heterocyclic group is -CH 2 does not constitute a ring The —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 —, or —NR na —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 selected from the group consisting 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 combined with the carbon atom to which each is bonded. To form an optionally substituted ring, and when the ring contains —CH 2 — that does not form a ring, —CH 2 — represents —O—, —CO—, —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 a plurality of R na are present, these may be the same or different.
M b + represents hydron or a b-valent metal ion. When a plurality of M b + are present, these may be the same or different. When M b + is hydrone, the hydrone is present 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 n = b × m / a.
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－ＮＲｎｂ－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－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－ＮＲｎｂ－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からなる群より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－ＮＲｎｂ－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－ＯＲｎｂ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ１）、－ＣＯ－Ｎ（Ｒｎｂ１）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎｂ１又は－Ｓ（Ｏ）２－Ｒｎｂ１を表す。
　ただし、Ｒ６が－ＣＯ－ＮＨ（Ｒｎｂ１）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－ＮＲｎｂ－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からなる群より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－ＮＲｎｂ－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－ＮＲｎｂ－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－ＮＲｎｂ－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。 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 which may have a substituent or a hydrogen atom, and —CH contained in the hydrocarbon group 2 - the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO -, - S (O) 2 - or -NR nb - to have replaced May be. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R 2 to R 5 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
At least one selected from the group consisting of R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may have a substituent together with the carbon atom to which each is bonded. A ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR nb — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R 6 represents —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 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
(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 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR nb- may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. R 2 to R 5 which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, —O—, —CO—, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
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, -CH 2 - contained in the hydrocarbon group and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 -Or -NR nb- may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. R 7 may be combined with the carbon atom to which R 6 and R 7 are bonded to form a ring.
X represents a group represented by the formula (1a).
Figure JPOXMLDOC01-appb-I000007
Figure JPOXMLDOC01-appb-I000007
［式（１ａ）中、
　Ｒ１７ｂ及びＲ１８ｂ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－ＮＲｎｂ－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。
　Ｒ１７ｂとＲ１８ｂ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－ＮＲｎｂ－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。］
　Ｒｎｂ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。Ｒｎｂが複数個存在する場合、これらは同一でもよく、異なっていてもよい。
　Ｒｎｂ１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－ＮＲｎｂ１０－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。Ｒｎｂ１が複数個存在する場合、これらは同一でもよく、異なっていてもよい。
　Ｒｎｂ１０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。Ｒｎｂ１０が複数個存在する場合、これらは同一でもよく、異なっていてもよい。］ [In Formula (1a),
R 17b and R 18b each independently represent 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R 17b and R 18b may form a ring optionally having a substituent together with the carbon atom to which each is bonded, and when the ring contains —CH 2 — that does not form a ring, The —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR nb —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
* 1 represents a bond to the 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 two or more Rnb exists, these may be the same and may differ.
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 —CH 2 — contained in the hydrocarbon group and it is, -O - - the -CH 2 when including - heterocyclic group -CH 2 that does not constitute a ring, - CO -, - S ( O) 2 - or -NR NB 10 - may be replaced by . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. When two or more Rnb1 exists, these may be the same and may differ.
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 two or more Rnb10 exists, these may be the same and may differ. ]
　［２］　式（１ａ）で表される基が、式（２ａ）で表される基である、［１］に記載の着色剤分散液。 [2] The colorant dispersion according to [1], wherein the group represented by the formula (1a) is a group represented by the formula (2a).
Figure JPOXMLDOC01-appb-I000008
Figure JPOXMLDOC01-appb-I000008
［式（２ａ）中、
　Ｒ１９ｂ及びＲ２０ｂ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－ＮＲｎｂ－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。
　Ｒｎｂ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。］ [In Formula (2a),
R 19b and R 20b each independently represent 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, the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring - -CH 2 contained in the hydrogen group, -O -, - CO -, - S (O) 2 - or -NR nb- may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R nb represents the same meaning as described above.
* 2 represents a bond to the isoindoline ring. ]
　［３］　式（Ｉ）中、
ａ）ａが１～１０のいずれかの整数である場合、
　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－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－ＮＲｎａ－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－からなる群より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、及び、Ｒ４とＲ５からなる群より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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　Ｒ６は、－ＣＯ－ＯＲｎａ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎａ１）、－ＣＯ－Ｎ（Ｒｎａ１）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎａ１又は－Ｓ（Ｏ）２－Ｒｎａ１を表す。
　ただし、Ｒ６が－ＣＯ－ＮＨ（Ｒｎａ１）を表す場合、Ｒ２～Ｒ５は、（ｉａ）及び（ｉｉａ）の少なくとも一方を充足する。
　（ｉａ）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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　（ｉｉａ）Ｒ２とＲ３、Ｒ３とＲ４、及び、Ｒ４とＲ５からなる群より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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　Ｒ７は、シアノ基を表す。
　Ｘは、式（１ａ－ｘ）で表される基を表す。 [3] In formula (I),
a) When a is an integer of 1 to 10,
R 2 to R 5 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 selected from the group consisting of R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may have a substituent together with the carbon atom to which each is bonded. A ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR na — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. The ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
R 6 represents —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 6 represents —CO—NH (R na1 ), R 2 to R 5 satisfy at least one of (ia) and (ia).
(Ia) At least one of R 2 to R 5 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 — .
(Iii) 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 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR It may be replaced with na-. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. The ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — . R 2 to R 5 which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, It may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 7 represents a cyano group.
X represents a group represented by the formula (1a-x).
Figure JPOXMLDOC01-appb-I000009
Figure JPOXMLDOC01-appb-I000009
［式（１ａ－ｘ）中、
　Ｒ２１及び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－ＮＲｎａ－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－からなる群より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、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－ＮＲｎａ－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－からなる群より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。］
　Ｒｎａは、前記と同じ意味を表す。
　Ｒｎａ１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－ＮＲｎａ１０－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。該炭化水素基及び該複素環基は、－ＣＯ２ －及び－Ｓ（Ｏ）２Ｏ－からなる群より選ばれる少なくとも一種を有していてもよい。Ｒｎａ１が複数個存在する場合、これらは同一でもよく、異なっていてもよい。
　Ｒｎａ１０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、Ｒｎａ１０が複数個存在する場合、これらは同一でもよく、異なっていてもよい。
ｂ）ａが０である場合、
　Ｒ７は、シアノ基を表す、［１］又は［２］に記載の着色剤分散液。 [In the formula (1a-x),
R 21 and R 22 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 together with the carbon atom to which each is bonded may form a ring that may have a substituent, and when the ring contains —CH 2 — that does not form a ring The —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. The ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
* 1 represents a bond to the isoindoline ring. ]
R na represents 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 —CH 2 — contained in the hydrocarbon group and it is, -O - - the -CH 2 when including - heterocyclic group -CH 2 that does not constitute a ring, - CO -, - S ( O) 2 - or -NR NA 10 - may be replaced by . However, —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —. 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 a plurality of R na1 are present, these may be the same or different.
R na10 represents an optionally substituted hydrocarbon group having 1 to 35 carbon atoms or an optionally substituted heterocyclic group, and when there are a plurality of Rna10 , these are the same. But it may be different.
b) If a is 0,
R 7 is the colorant dispersion according to [1] or [2], in which R 7 represents a cyano group.
　［４］　式（１ａ－ｘ）で表される基が、式（２ａ－ｘ）で表される基である、［３］に記載の着色剤分散液。 [4] The colorant dispersion according to [3], wherein the group represented by the formula (1a-x) is a group represented by the formula (2a-x).
Figure JPOXMLDOC01-appb-I000010
Figure JPOXMLDOC01-appb-I000010
［式（２ａ－ｘ）中、
　Ｒ２３及び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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　Ｒｎａ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。］ [In the formula (2a-x)
R 23 and R 24 each independently represent 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, the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring - -CH 2 contained in the hydrogen group, -O -, - CO -, - S (O) 2 - or -NR na- may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 represents the same meaning as described above.
* 2 represents a bond to the isoindoline ring. ]
　［５］　ヒドロキシ基を有する炭素数１～４０の脂肪族カルボン酸のアニオンを有する金属塩（Ｃ）をさらに含む、［１］～［４］のいずれかに記載の着色剤分散液。
　［６］　［１］～［５］のいずれかに記載の着色剤分散液と、樹脂（Ｄ）とを含む、着色硬化性樹脂組成物。
　［７］　［１］～［５］のいずれかに記載の着色剤分散液又は［６］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。
　［８］　［７］に記載のカラーフィルタを含む、表示装置。 [5] The colorant dispersion according to any one of [1] to [4], further comprising a metal salt (C) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms and having a hydroxy group.
[6] A colored curable resin composition comprising the colorant dispersion according to any one of [1] to [5] and a resin (D).
[7] A color filter formed from the colorant dispersion according to any one of [1] to [5] or the colored curable resin composition according to [6].
[8] A display device including the color filter according to [7].
　本発明に係る着色剤分散液及び着色硬化性樹脂組成物によれば、良好なコントラストを示すカラーフィルタ、及びそれを含む表示装置を提供することができる。 The colorant dispersion and colored curable resin composition according to the present invention can provide a color filter exhibiting good contrast and a display device including the same.
　＜着色剤分散液＞
　本発明の着色剤分散液は、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）と、式（Ｉ）で表される化合物（Ｂ）との共分散物を含む。
　上記着色剤分散液によれば、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）を主成分とするにもかかわらず、該着色剤分散液又は該着色剤分散液を含む着色硬化性樹脂組成物から形成されるカラーフィルタ及びそれを用いた表示装置のコントラストを良好なものとすることができる。
　着色剤分散液は、ヒドロキシ基を有する炭素数１～４０の脂肪族カルボン酸のアニオンを有する金属塩（Ｃ）をさらに含むことができる。以下、ヒドロキシ基を有する炭素数１～４０の脂肪族カルボン酸のアニオンを有する金属塩（Ｃ）を「脂肪族カルボン酸金属塩（Ｃ）」ともいう。
　以下、各成分として例示する化合物は、特に断りのない限り、単独で又は複数種を組み合わせて使用することができる。 <Colorant dispersion>
The colorant dispersion of the present invention contains C.I. I. Pigment Yellow 138 (A) and a compound (B) represented by the formula (I) are included.
According to the colorant dispersion, C.I. I. Color filter formed from the colorant dispersion or a colored curable resin composition containing the colorant dispersion despite having Pigment Yellow 138 (A) as a main component, and contrast of a display device using the color filter Can be made good.
The colorant dispersion may further contain a metal salt (C) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms and having a hydroxy group. Hereinafter, the metal salt (C) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms and having a hydroxy group is also referred to as “aliphatic carboxylic acid metal salt (C)”.
Hereinafter, unless otherwise indicated, the compound illustrated as each component can be used individually or in combination of multiple types.
　〔１〕Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）
　共分散物に含まれるＣ．Ｉ．ピグメントイエロー１３８（Ａ）は、カラーインデックス（The Society of Dyers and Colourists出版）でピグメントに分類されている黄色顔料である。 [1] C.I. I. Pigment Yellow 138 (A)
C. contained in co-dispersion. I. Pigment Yellow 138 (A) is a yellow pigment classified as a pigment by the Color Index (published by The Society of Dyers and Colorists).
　〔２〕式（Ｉ）で表される化合物（Ｂ）
　共分散物は、式（Ｉ）で表される化合物（Ｂ）を含む。 [2] Compound (B) represented by formula (I)
The co-dispersion contains the compound (B) represented by the formula (I).
Figure JPOXMLDOC01-appb-I000011
Figure JPOXMLDOC01-appb-I000011
［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、０～１０のいずれかの整数である。 [In the formula (I),
a represents the total number of —CO 2 — and —S (O) 2 O — contained in the compound represented by the formula (I), and is an integer of 0 to 10.
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－ＮＲｎａ－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－からなる群より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－ＮＲｎａ－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－からなる群より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からなる群より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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　Ｒｎａ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－からなる群より選ばれる少なくとも一種を有していてもよい。Ｒｎａが複数個存在する場合、これらは同一でもよく、異なっていてもよい。
　Ｍｂ＋は、ヒドロン又はｂ価の金属イオンを表す。Ｍｂ＋が複数個存在する場合、これらは同一でもよく、異なっていてもよい。Ｍｂ＋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、Ｍｂ＋の個数を表す。
　ｎは、ｎ＝ｂ×ｍ／ａの関係を満たす数である。 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 which may have a substituent or a hydrogen atom, and —CH contained in the hydrocarbon group 2 - the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO -, - S (O) 2 - or -NR na - to have replaced May be. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 each independently 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, cyano. group, a nitro group, -CO 2 - or -S (O) 2 O - represents, -CH 2 - contained in the hydrocarbon group when including - and said heterocyclic group is -CH 2 does not constitute a ring The —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 —, or —NR na —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 selected from the group consisting 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 combined with the carbon atom to which each is bonded. To form an optionally substituted ring, and when the ring contains —CH 2 — that does not form a ring, —CH 2 — represents —O—, —CO—, —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 a plurality of R na are present, these may be the same or different.
M b + represents hydron or a b-valent metal ion. When a plurality of M b + are present, these may be the same or different. When M b + is hydrone, the hydrone is present 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 n = b × m / a.
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－ＮＲｎｂ－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－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－ＮＲｎｂ－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からなる群より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－ＮＲｎｂ－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－ＯＲｎｂ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ１）、－ＣＯ－Ｎ（Ｒｎｂ１）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎｂ１又は－Ｓ（Ｏ）２－Ｒｎｂ１を表す。
　ただし、Ｒ６が－ＣＯ－ＮＨ（Ｒｎｂ１）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－ＮＲｎｂ－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からなる群より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－ＮＲｎｂ－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－ＮＲｎｂ－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－ＮＲｎｂ－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。 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 which may have a substituent or a hydrogen atom, and —CH contained in the hydrocarbon group 2 - the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO -, - S (O) 2 - or -NR nb - to have replaced May be. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R 2 to R 5 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
At least one selected from the group consisting of R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may have a substituent together with the carbon atom to which each is bonded. A ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR nb — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R 6 represents —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 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
(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 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR nb- may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. R 2 to R 5 which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, —O—, —CO—, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
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, -CH 2 - contained in the hydrocarbon group and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 -Or -NR nb- may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. R 7 may be combined with the carbon atom to which R 6 and R 7 are bonded to form a ring.
X represents a group represented by the formula (1a).
Figure JPOXMLDOC01-appb-I000012
Figure JPOXMLDOC01-appb-I000012
［式（１ａ）中、
　Ｒ１７ｂ及びＲ１８ｂ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－ＮＲｎｂ－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。
　Ｒ１７ｂとＲ１８ｂ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－ＮＲｎｂ－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。］
　Ｒｎｂ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。Ｒｎｂが複数個存在する場合、これらは同一でもよく、異なっていてもよい。
　Ｒｎｂ１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－ＮＲｎｂ１０－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。Ｒｎｂ１が複数個存在する場合、これらは同一でもよく、異なっていてもよい。
　Ｒｎｂ１０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。Ｒｎｂ１０が複数個存在する場合、これらは同一でもよく、異なっていてもよい。］ [In Formula (1a),
R 17b and R 18b each independently represent 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R 17b and R 18b may form a ring optionally having a substituent together with the carbon atom to which each is bonded, and when the ring contains —CH 2 — that does not form a ring, The —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR nb —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
* 1 represents a bond to the 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 two or more Rnb exists, these may be the same and may differ.
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 —CH 2 — contained in the hydrocarbon group and it is, -O - - the -CH 2 when including - heterocyclic group -CH 2 that does not constitute a ring, - CO -, - S ( O) 2 - or -NR NB 10 - may be replaced by . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. When two or more Rnb1 exists, these may be the same and may differ.
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 two or more Rnb10 exists, these may be the same and may differ. ]
　式（１ａ）で表される基は、好ましくは式（２ａ）で表される基である。 The group represented by the formula (1a) is preferably a group represented by the formula (2a).
Figure JPOXMLDOC01-appb-I000013
Figure JPOXMLDOC01-appb-I000013
［式（２ａ）中、
　Ｒ１９ｂ及びＲ２０ｂ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－ＮＲｎｂ－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。
　Ｒｎｂ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。］ [In Formula (2a),
R 19b and R 20b each independently represent 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, the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring - -CH 2 contained in the hydrogen group, -O -, - CO -, - S (O) 2 - or -NR nb- may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R nb represents the same meaning as described above.
* 2 represents a bond to the isoindoline ring. ]
　〔２－１〕式（Ｉ）で表される化合物（Ｂ）の第１態様
　式（Ｉ）で表される化合物（Ｂ）の好ましい一態様である第１態様において、
　式（Ｉ）中、
ａ）ａが１～１０のいずれかの整数である場合、
　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－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－ＮＲｎａ－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－からなる群より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、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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　Ｒ６は、－ＣＯ－ＯＲｎａ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎａ１）、－ＣＯ－Ｎ（Ｒｎａ１）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎａ１又は－Ｓ（Ｏ）２－Ｒｎａ１を表す。
　ただし、Ｒ６が－ＣＯ－ＮＨ（Ｒｎａ１）を表す場合、Ｒ２～Ｒ５は、（ｉａ）及び（ｉｉａ）の少なくとも一方を充足する。
　（ｉａ）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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　（ｉｉａ）Ｒ２とＲ３、Ｒ３とＲ４、及び、Ｒ４とＲ５からなる群より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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　Ｒ７は、シアノ基を表す。
　Ｘは、式（１ａ－ｘ）で表される基を表す。 [2-1] First Embodiment of Compound (B) Represented by Formula (I) In the first embodiment which is a preferred embodiment of the compound (B) represented by formula (I):
In formula (I),
a) When a is an integer of 1 to 10,
R 2 to R 5 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 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 is bonded forms a ring that may have a substituent. -CH 2 is good, the ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR na - be replaced in Good. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. The ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
R 6 represents —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 6 represents —CO—NH (R na1 ), R 2 to R 5 satisfy at least one of (ia) and (ia).
(Ia) At least one of R 2 to R 5 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 — .
(Iii) 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 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR It may be replaced with na-. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. The ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — . R 2 to R 5 which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, It may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 7 represents a cyano group.
X represents a group represented by the formula (1a-x).
Figure JPOXMLDOC01-appb-I000014
Figure JPOXMLDOC01-appb-I000014
［式（１ａ－ｘ）中、
　Ｒ２１及び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－ＮＲｎａ－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－からなる群より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、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－ＮＲｎａ－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－からなる群より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。］
　Ｒｎａは、前記と同じ意味を表す。
　Ｒｎａ１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－ＮＲｎａ１０－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。該炭化水素基及び該複素環基は、－ＣＯ２ －及び－Ｓ（Ｏ）２Ｏ－からなる群より選ばれる少なくとも一種を有していてもよい。Ｒｎａ１が複数個存在する場合、これらは同一でもよく、異なっていてもよい。
　Ｒｎａ１０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、Ｒｎａ１０が複数個存在する場合、これらは同一でもよく、異なっていてもよい。 [In the formula (1a-x),
R 21 and R 22 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 together with the carbon atom to which each is bonded may form a ring that may have a substituent, and when the ring contains —CH 2 — that does not form a ring The —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. The ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
* 1 represents a bond to the isoindoline ring. ]
R na represents 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 —CH 2 — contained in the hydrocarbon group and it is, -O - - the -CH 2 when including - heterocyclic group -CH 2 that does not constitute a ring, - CO -, - S ( O) 2 - or -NR NA 10 - may be replaced by . However, —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —. 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 a plurality of R na1 are present, these may be the same or different.
R na10 represents an optionally substituted hydrocarbon group having 1 to 35 carbon atoms or an optionally substituted heterocyclic group, and when there are a plurality of Rna10 , these are the same. But it may be different.
ｂ）ａが０である場合、
　Ｒ７は、シアノ基を表す。 b) If a is 0,
R 7 represents a cyano group.
　式（１ａ－ｘ）で表される基は、好ましくは式（２ａ－ｘ）で表される基である。 The group represented by the formula (1a-x) is preferably a group represented by the formula (2a-x).
Figure JPOXMLDOC01-appb-I000015
Figure JPOXMLDOC01-appb-I000015
［式（２ａ－ｘ）中、
　Ｒ２３及び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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　Ｒｎａ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。］ [In the formula (2a-x)
R 23 and R 24 each independently represent 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, the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring - -CH 2 contained in the hydrogen group, -O -, - CO -, - S (O) 2 - or -NR na- may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 represents the same meaning as described above.
* 2 represents a bond to the isoindoline ring. ]
　〔２－２〕式（Ｉ）で表される化合物（Ｂ）の第２態様
　式（Ｉ）で表される化合物（Ｂ）の他の好ましい一態様である第２態様は、上記第１態様において、ａが０である式（ＩＩＢ）で表される化合物である。 [2-2] Second Embodiment of Compound (B) Represented by Formula (I) The second embodiment, which is another preferred embodiment of the compound (B) represented by formula (I), is the first embodiment described above. A compound represented by the formula (IIB) in which a is 0.
Figure JPOXMLDOC01-appb-I000016
Figure JPOXMLDOC01-appb-I000016
［式（ＩＩＢ）中、
　Ｒ１１ｂ～Ｒ１５ｂは、それぞれ、式（Ｉ）においてａが０である場合のＲ１～Ｒ５と同じ意味を表す。
　Ｒ１２ｂとＲ１３ｂ、Ｒ１３ｂとＲ１４ｂ、及び、Ｒ１４ｂとＲ１５ｂからなる群より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－ＮＲｎｂ－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。
　Ｒ１６ｂは、－ＣＯ－ＯＲｎｂ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ１）、－ＣＯ－Ｎ（Ｒｎｂ１）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎｂ１又は－Ｓ（Ｏ）２－Ｒｎｂ１を表す。
　ただし、Ｒ１６ｂが－ＣＯ－ＮＨ（Ｒｎｂ１）を表す場合、Ｒ１２ｂ～Ｒ１５ｂは、（ｉｘｂ）及び（ｉｉｘｂ）の少なくとも一方を充足する。
　（ｉｘｂ）Ｒ１２ｂ～Ｒ１５ｂ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－ＮＲｎｂ－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。
　（ｉｉｘｂ）Ｒ１２ｂとＲ１３ｂ、Ｒ１３ｂとＲ１４ｂ、及び、Ｒ１４ｂとＲ１５ｂからなる群より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－ＮＲｎｂ－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。Ｒ１２ｂ～Ｒ１５ｂ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－ＮＲｎｂ－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。
　Ｘ１ｂは、式（１ａ－ｘｂ）で表される基を表す。 [In the formula (IIB),
R 11b to R 15b each have the same meaning as R 1 to R 5 when a is 0 in formula (I).
At least one selected from the group consisting of R 12b and R 13b , R 13b and R 14b , and R 14b and R 15b may have a substituent together with the carbon atom to which each is bonded. A ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR nb — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
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 (ixb).
(Ixb) At least one of R 12b to R 15b may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
(Ixb) At least one set selected from the group consisting of R 12b and R 13b , R 13b and R 14b , and R 14b and R 15b has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR nb- may be substituted . However, —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —. R 12b to R 15b which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, —O—, —CO—, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
X 1b represents a group represented by the formula (1a-xb).
Figure JPOXMLDOC01-appb-I000017
Figure JPOXMLDOC01-appb-I000017
［式（１ａ－ｘｂ）中、
　Ｒ２１ｂ、Ｒ２２ｂ及び＊１は、それぞれ、式（１ａ）中のＲ１７ｂ、Ｒ１８ｂ及び＊１と同じ意味を表す。］
　Ｒｎｂ及びＲｎｂ１は、前記と同じ意味を表す。］ [In the formula (1a-xb),
R 21b , R 22b and * 1 represent the same meaning as R 17b , R 18b and * 1 in the formula (1a), respectively. ]
R nb and R nb1 represent the same meaning as described above. ]
　式（ＩＩＢ）で表される化合物が有する－ＣＯ２Ｈ及び－Ｓ（Ｏ）２ＯＨの合計数は０である。 The total number of —CO 2 H and —S (O) 2 OH contained in the compound represented by the formula (IIB) is zero.
　式（１ａ－ｘｂ）で表される基は、好ましくは式（２ａ－ｘｂ）で表される基である。 The group represented by the formula (1a-xb) is preferably a group represented by the formula (2a-xb).
Figure JPOXMLDOC01-appb-I000018
Figure JPOXMLDOC01-appb-I000018
［式（２ａ－ｘｂ）中、
　Ｒ２３ｂ、Ｒ２４ｂ及び＊２は、それぞれ、式（２ａ）中のＲ１９ｂ、Ｒ２０ｂ及び＊２と同じ意味を表す。
　Ｒｎｂは、前記と同じ意味を表す。］ [In the formula (2a-xb),
R 23b , R 24b and * 2 represent the same meaning as R 19b , R 20b and * 2 in the formula (2a), respectively.
R nb represents the same meaning as described above. ]
　〔２－３〕式（Ｉ）で表される化合物（Ｂ）の第３態様
　式（Ｉ）で表される化合物（Ｂ）の他の好ましい一態様である第３態様は、式（Ｉ）中のａ（すなわち、式（Ｉ）で表される化合物が有する－ＣＯ２ －及び－Ｓ（Ｏ）２Ｏ－の合計数）が１～１０のいずれかの整数である式（ＩＡ）で表される化合物である。 [2-3] Third Embodiment of Compound (B) Represented by Formula (I) The third embodiment, which is another preferred embodiment of the compound (B) represented by formula (I), is represented by formula (I) In the formula (IA), a (that is, the total number of —CO 2 — and —S (O) 2 O — contained in the compound represented by the formula (I)) is an integer of 1 to 10. It is a compound represented.
Figure JPOXMLDOC01-appb-I000019
Figure JPOXMLDOC01-appb-I000019
［式（ＩＡ）中、
　Ｒ１ａ～Ｒ９ａは、それぞれ、式（Ｉ）においてａが１～１０のいずれかの整数である場合のＲ１～Ｒ９と同じ意味を表す。
　Ｒ２ａとＲ３ａ、Ｒ３ａとＲ４ａ、Ｒ４ａとＲ５ａ、Ｒ６ａとＲ７ａ、及び、Ｒ８ａとＲ９ａからなる群より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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
　Ｒｎａ及びＭｂ＋は、前記と同じ意味を表す。
　ｂは、１～６のいずれかの整数を表す。
　ａａは、式（ＩＡ）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、１～１０のいずれかの整数である。
　ｍａは、Ｍｂ＋の個数を表す。
　ｎａは、ｎａ＝ｂ×ｍａ／ａａの関係を満たす数である。］ [In the formula (IA),
R 1a to R 9a represent the same meaning as R 1 to R 9 in the case where a is any integer of 1 to 10 in the formula (I), respectively.
At least one selected from the group consisting 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 is combined with the carbon atom to which each is bonded. To form an optionally substituted ring, and when the ring contains —CH 2 — that does not form a ring, —CH 2 — represents —O—, —CO—, —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. The ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
R na and M b + represent the same meaning as described above.
b represents an integer of 1 to 6.
aa represents the total number of —CO 2 — and —S (O) 2 O — contained in the compound represented by the formula (IA), and is an integer of 1 to 10.
ma represents the number of M b + .
na is a number that satisfies the relationship na = b × ma / aa. ]
　〔２－４〕式（Ｉ）で表される化合物（Ｂ）の第４態様
　式（Ｉ）で表される化合物（Ｂ）の他の好ましい一態様である第４態様は、式（Ｉ）中のａが０である式（ＩＢ）で表される化合物である。 [2-4] Fourth Embodiment of Compound (B) Represented by Formula (I) The fourth embodiment, which is another preferred embodiment of the compound (B) represented by formula (I), is represented by formula (I) It is a compound represented by the formula (IB) in which a is 0.
Figure JPOXMLDOC01-appb-I000020
Figure JPOXMLDOC01-appb-I000020
［式（ＩＢ）中、
　Ｒ１ｂ～Ｒ５ｂは、それぞれ、式（Ｉ）においてａが０である場合のＲ１～Ｒ５と同じ意味を表す。
　Ｒ２ｂとＲ３ｂ、Ｒ３ｂとＲ４ｂ、及び、Ｒ４ｂとＲ５ｂからなる群より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－ＮＲｎｂ－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。
　Ｒ６ｂは、－ＣＯ－ＯＲｎｂ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ１）、－ＣＯ－Ｎ（Ｒｎｂ１）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎｂ１又は－Ｓ（Ｏ）２－Ｒｎｂ１を表す。
　ただし、Ｒ６ｂが－ＣＯ－ＮＨ（Ｒｎｂ１）を表す場合、Ｒ２ｂ～Ｒ５ｂは、（ｉｂｂ）及び（ｉｉｂｂ）の少なくとも一方を充足する。
　（ｉｂｂ）Ｒ２ｂ～Ｒ５ｂ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－ＮＲｎｂ－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。
　（ｉｉｂｂ）Ｒ２ｂとＲ３ｂ、Ｒ３ｂとＲ４ｂ、及び、Ｒ４ｂとＲ５ｂからなる群より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－ＮＲｎｂ－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。Ｒ２ｂ～Ｒ５ｂ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－ＮＲｎｂ－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。
　Ｒ７ｂは、式（Ｉ）においてａが０である場合のＲ７と同じ意味を表す。Ｒ７ｂは、Ｒ６ｂ及びＲ７ｂ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。
　Ｘｂは、式（Ｉ）においてａが０である場合のＸと同じ意味を表す。
　Ｒｎｂ、Ｒｎｂ１及びＲｎｂ１０は、前記と同じ意味を表す。］ [In the formula (IB),
R 1b to R 5b represent the same meaning as R 1 to R 5 when a is 0 in formula (I), respectively.
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 may have a substituent together with the carbon atom to which each is bonded. A ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR nb — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R 6b 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 6b represents —CO—NH (R nb1 ), R 2b to R 5b satisfy at least one of (ibb) and (iibb).
(Ibb) 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 that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
(Iibb) 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 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR nb- may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. R 2b to R 5b which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, —O—, —CO—, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R 7b represents the same meaning as R 7 when a is 0 in formula (I). R 7b may form a ring together with the carbon atom to which R 6b and R 7b are bonded.
Xb represents the same meaning as X when a is 0 in formula (I).
R nb , R nb1 and R nb10 represent the same meaning as described above. ]
　式（ＩＢ）で表される化合物に含まれる－ＣＯ２Ｈ及び－Ｓ（Ｏ）２ＯＨの合計数は０である。 The total number of —CO 2 H and —S (O) 2 OH contained in the compound represented by the formula (IB) is zero.
　式（ＩＢ）で表される化合物において、上記式（１ａ）で表される基は、好ましくは上記式（２ａ）で表される基である。 In the compound represented by the formula (IB), the group represented by the formula (1a) is preferably a group represented by the formula (2a).
　本明細書において、置換基を有する炭化水素基の炭素数は、置換基によって置換される前の炭化水素基の炭素数である。
　炭化水素基に含まれる－ＣＨ２－が－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－、－ＮＲｎａ－、－ＮＲｎｂ－、－ＮＲｎａ１０－又は－ＮＲｎｂ１０－等に置き換わって形成される基の炭素数は、該基によって置換される前の炭化水素基の炭素数である。
　炭化水素基に含まれる－ＣＨ２－が－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－、－ＮＲｎａ－、－ＮＲｎｂ－、－ＮＲｎａ１０－又は－ＮＲｎｂ１０－に置き換わることによって形成される基を総称して、以下、「基（Ｚ）」ともいう。 In the present specification, the carbon number of the hydrocarbon group having a substituent is the carbon number of the hydrocarbon group before being substituted by the substituent.
Is -O - - -CH 2 contained in the hydrocarbon group, - CO -, - S ( O) 2 -, - NR na -, - NR nb -, - NR na10 - or -NR NB 10 - like replaced by the The carbon number of the formed group is the carbon number of the hydrocarbon group before being substituted by the group.
By replacing —CH 2 — contained in the hydrocarbon group with —O—, —CO—, —S (O) 2 —, —NR na —, —NR nb —, —NR na10 — or —NR nb10 —. Hereinafter, the formed groups are also collectively referred to as “group (Z)”.
　〔２－５〕式（Ｉ）で表される化合物（Ｂ）及びその第１～第４態様に係る化合物が有する基の説明
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１６ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０、Ｒｎｂ１０、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４で表される基は通常、１価の基である。 [2-5] Description of groups possessed by the compound (B) represented by the formula (I) and the compounds according to the first to fourth embodiments thereof R 1 to R 9 , R 11b to R 16b , R 1a to R 9a R 1b to R 7b , R na , R nb , R na1 , R nb1 , R na10 , R nb10 , R 17b to R 24b , and R 21 to R 24 are usually monovalent groups. .
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４で表される炭素数１～４０の炭化水素基、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される炭素数１～３５の炭化水素基は、脂肪族炭化水素基又は芳香族炭化水素基であってもよく、該脂肪族炭化水素基は、飽和又は不飽和であってもよく、鎖状又は脂環式であってもよい。
　ａが１～１０のいずれかの整数である場合において、Ｒ１～Ｒ９、Ｒ１ａ～Ｒ９ａ、Ｒ２１～Ｒ２４及びＲｎａで表される炭化水素基は、－ＣＯ２ －及び－Ｓ（Ｏ）２Ｏ－からなる群より選ばれる少なくとも一種を有していてもよい。 R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 The hydrocarbon group having 1 to 35 carbon atoms represented by 1 to 40 hydrocarbon group, R na1 , R nb1 , R na10 and R nb10 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain or alicyclic.
When a is an integer of 1 to 10, the hydrocarbon groups represented by R 1 to R 9 , R 1a to R 9a , R 21 to R 24 and R na are represented by —CO 2 — and — It may have at least one selected from the group consisting of S (O) 2 O 2 — .
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される飽和又は不飽和鎖状炭化水素基としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、ヘプタデシル基、オクタデシル基及びイコシル基等の直鎖状アルキル基等；イソプロピル基、（２－メチル）プロピル基、イソブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、（２－エチル）ブチル基、イソペンチル基、ネオペンチル基、ｔｅｒｔ－ペンチル基、（１－メチル）ペンチル基、（２－メチル）ペンチル基、（１－エチル）ペンチル基、（３－エチル）ペンチル基、イソヘキシル基、（５－メチル）ヘキシル基、（２－エチル）ヘキシル基、及び（３－エチル）ヘプチル基等の分枝鎖状アルキル基等；ビニル基、１－プロペニル基、２－プロペニル基（アリル基）、イソプロペニル基、（１－メチル）エテニル基、２－ブテニル基、３－ブテニル基、１，３－ブタジエニル基、（１－（２－プロペニル））エテニル基、（１，２－ジメチル）プロペニル基及び２－ペンテニル基等のアルケニル基；等が挙げられる。 R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 Saturated or unsaturated chain hydrocarbon groups represented by R na10 and R nb10 are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl Group, undecyl group, dodecyl group, heptadecyl group, linear alkyl group such as octadecyl group and icosyl group, etc .; isopropyl group, (2-methyl) propyl group, isobutyl group, sec-butyl group, tert-butyl group, ( 2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl Branched chain alkyl such as (1-ethyl) pentyl group, (3-ethyl) pentyl group, isohexyl group, (5-methyl) hexyl group, (2-ethyl) hexyl group, and (3-ethyl) heptyl group Groups such as 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, ( Alkenyl groups such as 1- (2-propenyl)) ethenyl group, (1,2-dimethyl) propenyl group and 2-pentenyl group; and the like.
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４で表される飽和又は不飽和鎖状炭化水素基の炭素数は、好ましくは１～３０であり、より好ましくは１～２０であり、さらに好ましくは１～１５であり、さらにより好ましくは１～１０であり、さらにより一層好ましくは１～８であり、特に好ましくは１～５である。
　Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される飽和又は不飽和鎖状炭化水素基の炭素数は、好ましくは１～２８であり、より好ましくは１～１８であり、さらに好ましくは１～１３であり、さらにより好ましくは１～８であり、さらにより一層好ましくは１～６であり、特に好ましくは１～３である。 Saturation represented by R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 The number of carbon atoms of the unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, still more preferably 1 to 10, and even more. More preferably, it is 1-8, and particularly preferably 1-5.
The carbon number of the saturated or unsaturated chain hydrocarbon group represented by R na1 , R nb1 , R na10 and R nb10 is preferably 1 to 28, more preferably 1 to 18, and still more preferably 1 -13, even more preferably 1-8, even more preferably 1-6, and particularly preferably 1-3.
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される飽和又は不飽和脂環式炭化水素基としては、シクロプロピル基、１－メチルシクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、１－メチルシクロヘキシル基、２－メチルシクロヘキシル基、３－メチルシクロヘキシル基、４－メチルシクロヘキシル基、１，２－ジメチルシクロヘキシル基、１，３－ジメチルシクロヘキシル基、１，４－ジメチルシクロヘキシル基、２，３－ジメチルシクロヘキシル基、２，４－ジメチルシクロヘキシル基、２，５－ジメチルシクロヘキシル基、２，６－ジメチルシクロヘキシル基、３，４－ジメチルシクロヘキシル基、３，５－ジメチルシクロヘキシル基、２，２－ジメチルシクロヘキシル基、３，３－ジメチルシクロヘキシル基、４，４－ジメチルシクロヘキシル基、シクロオクチル基、２，４，６－トリメチルシクロヘキシル基、２，２，６，６－テトラメチルシクロヘキシル基、３，３，５，５－テトラメチルシクロヘキシル基、４－ペンチルシクロヘキシル基、４－オクチルシクロヘキシル基及び４－シクロヘキシルシクロヘキシル基等のシクロアルキル基；シクロヘキセニル基（例えばシクロヘキサ－２－エン、シクロヘキサ－３－エン）、シクロヘプテニル基及びシクロオクテニル基等のシクロアルケニル基；ノルボルナン基、アダマンチル基、ビシクロ［２．２．２］オクタン等が挙げられる。
　上記飽和又は不飽和脂環式炭化水素基の炭素数は、好ましくは３～３０であり、より好ましくは３～２０であり、さらに好ましくは４～２０であり、さらにより好ましくは４～１５であり、より一層好ましくは５～１５であり、特に好ましくは５～１０であり、中でも、シクロペンチル基、シクロヘキシル基、シクロへプチル基又はシクロオクチル基であることがとりわけ好ましい。 R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 The saturated or unsaturated alicyclic hydrocarbon group represented by R na10 and R nb10 includes a cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methyl Cyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethyl group Cyclohexyl, 2,4-dimethylcyclohexyl, 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, 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octyl A cycloalkyl group such as a cyclohexyl group and a 4-cyclohexylcyclohexyl group; a cycloalkenyl group such as a cyclohexenyl group (eg, cyclohex-2-ene, cyclohex-3-ene), a cycloheptenyl group, and a cyclooctenyl group; a norbornane group, an adamantyl group, a bicyclo [2. .2] octane, and the like.
The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 30 carbon atoms, more preferably 3 to 20, more preferably 4 to 20, and still more preferably 4 to 15 carbon atoms. And more preferably 5 to 15, particularly preferably 5 to 10, and particularly preferably a cyclopentyl group, a cyclohexyl group, a cycloheptyl group or a cyclooctyl group.
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される飽和又は不飽和炭化水素基は、上記に挙げた鎖状炭化水素基と脂環式炭化水素基とを組み合わせた基であってもよく、例えば、シクロプロピルメチル基、シクロプロピルエチル基、シクロブチルメチル基、シクロブチルエチル基、シクロペンチルメチル基、シクロペンチルエチル基、シクロヘキシルメチル基及びシクロヘキシルエチル基等の１つ以上の脂環式炭化水素基が結合したアルキル基が挙げられる。
　鎖状炭化水素基と脂環式炭化水素基とを組み合わせた基の炭素数は、好ましくは４～３０であり、より好ましくは４～２０であり、さらに好ましくは４～１５である。 R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 The saturated or unsaturated hydrocarbon group represented by R na10 and R nb10 may be a group in which the chain hydrocarbon group and the alicyclic hydrocarbon group listed above are combined. For example, cyclopropyl An alkyl group to which one or more alicyclic hydrocarbon groups such as methyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group and cyclohexylethyl group are bonded Is mentioned.
The number of carbon atoms of a group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group is preferably 4 to 30, more preferably 4 to 20, and still more preferably 4 to 15.
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される芳香族炭化水素基としては、フェニル基、ｏ－トリル基、ｍ－トリル基、ｐ－トリル基、２，３－ジメチルフェニル基、２，４－ジメチルフェニル基、２，５－ジメチルフェニル基、２，６－ジメチルフェニル基、３，４－ジメチルフェニル基、３，５－ジメチルフェニル基、ｏ－イソプロピルフェニル基、ｍ－イソプロピルフェニル基、ｐ－イソプロピルフェニル基、ｏ－ｔｅｒｔ－ブチルフェニル基、ｍ－ｔｅｒｔ－ブチルフェニル基、ｐ－ｔｅｒｔ－ブチルフェニル基、メシチル基、２，６－ビス（２－プロピル）フェニル基、２，４，６－トリメチルフェニル基、１－ナフチル基、２－ナフチル基、５，６，７，８－テトラヒドロ－１－ナフチル基、５，６，７，８－テトラヒドロ－２－ナフチル基、フルオレニル基、フェナントリル基及びアントリル基等の芳香族炭化水素基；等が挙げられる。
　上記芳香族炭化水素基の炭素数は、好ましくは６～３０であり、より好ましくは６～２０であり、さらに好ましくは６～１５である。 R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 The aromatic hydrocarbon groups represented by R na10 and R nb10 include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2,3-dimethylphenyl group, and a 2,4-dimethylphenyl group. 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-propylene ) 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 -Aromatic hydrocarbon groups such as naphthyl group, fluorenyl group, phenanthryl group and anthryl group;
The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and still more preferably 6 to 15 carbon atoms.
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される芳香族炭化水素基は、芳香族炭化水素環を有する炭化水素基である限り特に限定されず、上記に挙げた鎖状炭化水素基、脂環式炭化水素基、及び芳香族炭化水素基の少なくとも一つを、上記に挙げた芳香族炭化水素基と組み合わせた基であってもよく、例えば、ベンジル基、２－メチルベンジル基、３－メチルベンジル基、４－メチルベンジル基、フェニルエチル基、フェニルプロピル基及び１－メチル－１－フェニルエチル基等のアラルキル基；フェニルエテニル基（フェニルビニル基）等のアリールアルケニル基；フェニルエチニル基等のアリールアルキニル基；ビフェニリル基及びターフェニリル基等の１つ以上のフェニル基が結合したフェニル基；シクロヘキシルメチルフェニル基、ベンジルフェニル基、（ジメチル（フェニル）メチル）フェニル基；等が挙げられる。
　鎖状炭化水素基、脂環式炭化水素基、及び芳香族炭化水素基の少なくとも一つを芳香族炭化水素基と組み合わせた基の炭素数は、好ましくは７～３０であり、より好ましくは７～２０であり、さらに好ましくは７～１５である。 R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 The aromatic hydrocarbon group represented by R na10 and R nb10 is not particularly limited as long as it is a hydrocarbon group having an aromatic hydrocarbon ring, and the chain hydrocarbon group and alicyclic hydrocarbon listed above Group and at least one of the aromatic hydrocarbon groups may be a group in combination with the aromatic hydrocarbon group listed above, for example, benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, Aralkyl groups such as 4-methylbenzyl group, phenylethyl group, phenylpropyl group and 1-methyl-1-phenylethyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group) Arylalkynyl groups such as phenylethynyl group; phenyl groups to which one or more phenyl groups such as biphenylyl group and terphenylyl group are bonded; cyclohexylmethylphenyl group, benzylphenyl group, (dimethyl (phenyl) methyl) phenyl group; It is done.
The number of carbon atoms of a group obtained by combining at least one of a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group with an aromatic hydrocarbon group is preferably 7 to 30, and more preferably 7 -20, more preferably 7-15.
　また、Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される炭化水素基は、１価の置換基、又は２価の置換基を有していてもよい。２価の置換基は、２つの結合手が同じ炭素原子に結合して二重結合を形成する置換基であることが好ましい。 R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 , R na1 , The hydrocarbon groups represented by R nb1 , R na10 and R nb10 may have a monovalent substituent or a divalent substituent. The divalent substituent is preferably a substituent in which two bonds are bonded to the same carbon atom to form a double bond.
　１価の置換基としては、
　メチルチオ基、エチルチオ基、プロピルチオ基及びブチルチオ基等の炭素数１～１０のアルキルスルファニル基；
　フッ素原子、塩素原子、臭素原子及びヨウ素原子等のハロゲン原子；
　ニトロ基；シアノ基；
　トリフルオロメチル基、パーフルオロエチル基、パーフルオロプロピル基、パーフルオロイソプロピル基、パーフルオロブチル基、パーフルオロペンチル基、パーフルオロヘキシル基、パーフルオロヘプチル基、パーフルオロオクチル基、パーフルオロノニル基、パーフルオロデシル基、パーフルオロシクロヘキシル基及びパーフルオロフェニル基等の水素原子の全てをフッ素原子で置換した炭素数１～２０、好ましくは炭素数１～１０の炭化水素基；
　＊－ＣＯ－ＳＨ；
　＊－ＣＯ－Ｓ－ＣＨ３、＊－ＣＯ－Ｓ－ＣＨ２ＣＨ３、＊－ＣＯ－Ｓ－ＣＨ２－ＣＨ２－ＣＨ３、及び＊－ＣＯ－Ｓ－ＣＨ２－ＣＨ２－ＣＨ２－ＣＨ３等のアルキル基（該アルキル基の炭素数は１～１０）と結合した硫黄原子と結合したカルボニル基；
　＊－ＣＯ－Ｓ－Ｃ６Ｈ５等のアリール基（該アリール基の炭素数は６～２０）と結合した硫黄原子と結合したカルボニル基；
　＊－ＯＰ（Ｏ）（ＯＲｎｂ２）２；
　＊－Ｓｉ（Ｒｎｂ２）（Ｒｎｂ３）（Ｒｎｂ４）；等が挙げられる。
［前記式中、
　＊は、上記炭化水素基との結合手を表す。
　Ｒｎｂ２、Ｒｎｂ３、Ｒｎｂ４は、同一であってもよく異なっていてもよく、互いに独立に、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－、－Ｎｎｂ１０－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。
　Ｒｎｂ１０は、前記と同じ意味を表す。
　Ｒｎｂ２、Ｒｎｂ３、Ｒｎｂ４の具体例及び好ましい例は、Ｒｎｂ１と同様である。］ As a monovalent substituent,
An alkylsulfanyl 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 perfluorodecyl group, perfluorocyclohexyl group and perfluorophenyl group are substituted with fluorine atoms;
* -CO-SH;
* -CO-S-CH 3, * - CO-S-CH 2 CH 3, * - CO-S-CH 2 -CH 2 -CH 3, and * -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);
* A carbonyl group bonded to a sulfur atom bonded to an aryl group such as —CO—S—C 6 H 5 (the aryl group has 6 to 20 carbon atoms);
* -OP (O) (OR nb2 ) 2 ;
* -Si (R nb2 ) (R nb3 ) (R nb4 );
[In the above formula,
* Represents a bond with the hydrocarbon group.
R nb2 , R nb3 , and R nb4 may be the same or different, and independently of each other, may have a hydrocarbon group having 1 to 35 carbon atoms, or a substituent. to represent also heterocyclic group optionally, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O- , —CO—, —S (O) 2 —, and —N nb10 — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
R nb10 represents the same meaning as described above.
Specific examples and preferred examples of R nb2, R nb3, R nb4 is the same as R nb1. ]
　２価の置換基としては、チオキソ基、イミノ基、炭素数１～２０（好ましくは炭素数１～１０）のアルキル基が置換したイミノ基、及び炭素数６～２０のアリール基が置換したイミノ基等が挙げられる。
　アルキル基が置換したイミノ基としては、ＣＨ３－Ｎ＝、ＣＨ３－ＣＨ２－Ｎ＝、ＣＨ３－（ＣＨ２）２－Ｎ＝、ＣＨ３－（ＣＨ２）３－Ｎ＝等が挙げられる。
　アリール基が置換したイミノ基としては、Ｃ６Ｈ５－Ｎ＝等が挙げられる。 Examples of the divalent substituent include 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. Groups and the like.
Examples of the imino group substituted with an 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 an aryl group include C 6 H 5 —N═.
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される炭化水素基の置換基としては、
　ハロゲン原子；ニトロ基；シアノ基；水素原子の全てをフッ素原子で置換した炭素数１～２０の炭化水素基；チオカルボニル基；＊－ＯＰ（Ｏ）（ＯＲｎｂ２）２；＊－Ｓｉ（Ｒｎｂ２）（Ｒｎｂ３）（Ｒｎｂ４）；等が好ましく、
　ハロゲン原子；ニトロ基；シアノ基；水素原子の全てをフッ素原子で置換した炭素数１～２０の炭化水素基；チオカルボニル基；等がより好ましく、
　フッ素原子、塩素原子、臭素原子；ニトロ基；シアノ基；水素原子の全てをフッ素原子で置換した炭素数１～１０の炭化水素基；チオカルボニル基；等がさらに好ましい。 R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 As a substituent of the hydrocarbon group represented by R na10 and R nb10 ,
A halogen atom; a nitro group; a cyano group; a hydrocarbon group having 1 to 20 carbon atoms in which all of the hydrogen atoms are substituted with fluorine atoms; a thiocarbonyl group; * -OP (O) (OR nb2 ) 2 ; * -Si (R nb2 ) ( Rnb3 ) ( Rnb4 );
A halogen atom; a nitro group; a cyano group; a hydrocarbon group having 1 to 20 carbon atoms in which all of the hydrogen atoms are substituted with fluorine atoms; a thiocarbonyl group;
More preferred are a fluorine atom, a chlorine atom, a bromine atom; a nitro group; a cyano group; a hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms; a thiocarbonyl group;
　ａが１～１０のいずれかの整数である場合、Ｒ１～Ｒ９、Ｒ１ａ～Ｒ９ａ、Ｒ２１～Ｒ２４で表される炭化水素基に含まれる－ＣＨ２－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－又は－ＮＲｎａ－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。
　ａが０である場合、Ｒ１～Ｒ５、Ｒ７、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒ１７ｂ～Ｒ２４ｂで表される炭化水素基に含まれる－ＣＨ２－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－又は－ＮＲｎｂ－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。
　Ｒｎａ１で表される炭化水素基に含まれる－ＣＨ２－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－又は－ＮＲｎａ１０－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。
　Ｒｎｂ１で表される炭化水素基に含まれる－ＣＨ２－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－又は－ＮＲｎｂ１０－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。 When a is an integer of 1 to 10, —CH 2 — contained in the hydrocarbon group represented by R 1 to R 9 , R 1a to R 9a , R 21 to R 24 is —O— , —CO—, —S (O) 2 —, or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
When a is 0, —CH 2 — contained in the hydrocarbon group represented by R 1 to R 5 , R 7 , R 11b to R 15b , R 1b to R 5b , R 7b , R 17b to R 24b May be replaced by —O—, —CO—, —S (O) 2 — or —NR nb —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
—CH 2 — contained in the hydrocarbon group represented by R na1 may be replaced by —O—, —CO—, —S (O) 2 —, or —NR na10 —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
—CH 2 — contained in the hydrocarbon group represented by R nb1 may be replaced by —O—, —CO—, —S (O) 2 —, or —NR nb10 —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
　炭化水素基に含まれる－ＣＨ２－が－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－、－ＮＲｎａ－、－ＮＲｎｂ－、－ＮＲｎａ１０－又は－ＮＲｎｂ１０－に置き換わることによって形成される基（Ｚ）としては、
　メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、イソブトキシ基、ｓｅｃ－ブトキシ基、ｔｅｒｔ－ブトキシ基、ペンチルオキシ基、ヘキシルオキシ基、（２－エチル）ヘキシルオキシ基、ヘプチルオキシ基、オクチルオキシ基、ノニルオキシ基、フェニルオキシ基、及びｏ－トリルオキシ基等の炭素数が１～２０、より好ましくは炭素数１～１０の炭化水素基が片側に結合したオキシ基；
　エポキシ基；
　ホルミル基;
　アセチル基、プロパノイル基、ブタノイル基、ｔｅｒｔ－ブタノイル基、ペンタノイル基、ヘキサノイル基、（２－エチル）ヘキサノイル基、ヘプタノイル基、オクタノイル基、ノナノイル基、及びベンゾイル基等の炭素数が２～２２、好ましくは炭素数が２～１２のアシル基（好ましくはアルカノイル基）；
　メトキシカルボニル基、エトキシカルボニル基、プロポキシカルボニル基、ブトキシカルボニル基、ｔｅｒｔ－ブトキシカルボニル基、ペンチルオキシカルボニル基、ヘキシルオキシカルボニル基、（２－エチル）ヘキシルオキシカルボニル基、ヘプチルオキシカルボニル基及びオクチルオキシカルボニル基、ノニルオキシカルボニル基、フェニルオキシカルボニル基、及びｏ－トリルオキシカルボニル基等の炭素数１～２０、好ましくは炭素数１～１０の炭化水素基が結合したオキシカルボニル基；
　アミノ基；
　Ｎ－メチルアミノ基、Ｎ，Ｎ－ジメチルアミノ基、Ｎ－エチルアミノ基、Ｎ，Ｎ－ジエチルアミノ基、Ｎ－プロピルアミノ基、Ｎ，Ｎ－ジプロピルアミノ基、Ｎ－イソプロピルアミノ基、Ｎ，Ｎ－ジイソプロピルアミノ基、Ｎ－ブチルアミノ基、Ｎ，Ｎ－ジブチルアミノ基、Ｎ－イソブチルアミノ基、Ｎ，Ｎ－ジイソブチルアミノ基、Ｎ－ｓｅｃ－ブチルアミノ基、Ｎ，Ｎ－ジｓｅｃ－ブチルアミノ基、Ｎ－ｔｅｒｔ－ブチルアミノ基、Ｎ，Ｎ－ジｔｅｒｔ－ブチルアミノ基、Ｎ－ペンチルアミノ基、Ｎ，Ｎ－ジペンチルアミノ基、Ｎ－（１－エチルプロピル）アミノ基、Ｎ，Ｎ－ジ（１－エチルプロピル）アミノ基、Ｎ－ヘキシルアミノ基、Ｎ，Ｎ－ジヘキシルアミノ基、Ｎ－（２－エチル）ヘキシルアミノ基、Ｎ，Ｎ－ジ（２－エチル）ヘキシルアミノ基、Ｎ－ヘプチルアミノ基、Ｎ，Ｎ－ジヘプチルアミノ基、Ｎ－オクチルアミノ基、Ｎ，Ｎ－ジオクチルアミノ基、Ｎ－ノニルアミノ基、Ｎ，Ｎ－ジノニルアミノ基、Ｎ－フェニルアミノ基、Ｎ，Ｎ－ジフェニルアミノ基、Ｎ，Ｎ－エチルメチルアミノ基、Ｎ，Ｎ－プロピルメチルアミノ基、Ｎ，Ｎ－イソプロピルメチルアミノ基、Ｎ，Ｎ－ブチルメチルアミノ基、Ｎ，Ｎ－ｔｅｒｔ－ブチルメチルアミノ基、及びＮ，Ｎ－フェニルメチルアミノ基等の１つ又は２つの炭素数１～１０、好ましくは炭素数１～２０の炭化水素基で置換されたアミノ基；
　スルファモイル基；
　Ｎ－メチルスルファモイル基、Ｎ，Ｎ－ジメチルスルファモイル基、Ｎ－エチルスルファモイル基、Ｎ，Ｎ－ジエチルスルファモイル基、Ｎ－プロピルスルファモイル基、Ｎ，Ｎ－ジプロピルスルファモイル基、Ｎ－イソプロピルスルファモイル基、Ｎ，Ｎ－ジイソプロピルスルファモイル基、Ｎ－ブチルスルファモイル基、Ｎ，Ｎ－ジブチルスルファモイル基、Ｎ－イソブチルスルファモイル基、Ｎ，Ｎ－ジイソブチルスルファモイル基、Ｎ－ｓｅｃ－ブチルスルファモイル基、Ｎ，Ｎ－ジｓｅｃ－ブチルスルファモイル基、Ｎ－ｔｅｒｔ－ブチルスルファモイル基、Ｎ，Ｎ－ジｔｅｒｔ－ブチルスルファモイル基、Ｎ－ペンチルスルファモイル基、Ｎ，Ｎ－ジペンチルスルファモイル基、Ｎ－（１－エチルプロピル）スルファモイル基、Ｎ，Ｎ－ジ（１－エチルプロピル）スルファモイル基、Ｎ－ヘキシルスルファモイル基、Ｎ，Ｎ－ジヘキシルスルファモイル基、Ｎ－（２－エチル）ヘキシルスルファモイル基、Ｎ，Ｎ－ジ（２－エチル）ヘキシルスルファモイル基、Ｎ－ヘプチルスルファモイル基、Ｎ，Ｎ－ジヘプチルスルファモイル基、Ｎ－オクチルスルファモイル基、Ｎ，Ｎ－ジオクチルスルファモイル基、Ｎ，Ｎ－オクチルメチルスルファモイル基、Ｎ－ノニルスルファモイル基、Ｎ，Ｎ－ジノニルスルファモイル基、Ｎ－フェニルスルファモイル基、Ｎ，Ｎ－ジフェニルスルファモイル基、Ｎ，Ｎ－エチルメチルスルファモイル基、Ｎ，Ｎ－プロピルメチルスルファモイル基、Ｎ，Ｎ－イソプロピルメチルスルファモイル基、Ｎ，Ｎ－ブチルメチルスルファモイル基、Ｎ，Ｎ－ｔｅｒｔ－ブチルメチルスルファモイル基、及びＮ，Ｎ－フェニルメチルスルファモイル基等の１つ又は２つの炭素数１～２０、好ましくは炭素数１～１０の炭化水素基で置換されたスルファモイル基；
　ホルミルアミノ基；アセチルアミノ基、プロパノイルアミノ基、ブタノイルアミノ基、２，２－ジメチルプロパノイルアミノ基、ペンタノイルアミノ基、ヘキサノイルアミノ基、（２－エチル）ヘキサノイルアミノ基、ヘプタノイルアミノ基、オクタノイルアミノ基、ノナノイルアミノ基、デカノイルアミノ基、ウンデカノイルアミノ基、ドデカノイルアミノ基、ヘンイコサノイルアミノ基、及びベンゾイルアミノ基等の炭素数１～２２、好ましくは炭素数１～１２のアルカノイルアミノ基；
　ヒドロキシ基；
　ホルミルオキシ基、アセトキシ基、プロパノイルオキシ基、ブタノイルオキシ基、２，２－ジメチルプロパノイルオキシ基、ペンタノイルオキシ基、ヘキサノイルオキシ基、（２－エチル）ヘキサノイルオキシ基、ヘプタノイルオキシ基、オクタノイルオキシ基、ノナノイルオキシ基、及びベンゾイルオキシ基等の炭素数１～２０、好ましくは炭素数１～１０のアルカノイルオキシ基；
　メチルスルホニル基、エチルスルホニル基、プロピルスルホニル基、ブチルスルホニル基、ペンチルスルホニル基、ヘキシルスルホニル基、（２－エチル）ヘキシルスルホニル基、ヘプチルスルホニル基、オクチルスルホニル基、ノニルスルホニル基、デシルスルホニル基、フェニルスルホニル基、及びｐ－トリルスルホニル基等の炭素数１～２０、好ましくは炭素数１～１０の炭化水素基が置換したスルホニル基；
　カルバモイル基；
　Ｎ－メチルカルバモイル基、Ｎ，Ｎ－ジメチルカルバモイル基、Ｎ－エチルカルバモイル基、Ｎ，Ｎ－ジエチルカルバモイル基、Ｎ－プロピルカルバモイル基、Ｎ，Ｎ－ジプロピルカルバモイル基、Ｎ－イソプロピルカルバモイル基、Ｎ，Ｎ－ジイソプロピルカルバモイル基、Ｎ－ブチルカルバモイル基、Ｎ，Ｎ－ジブチルカルバモイル基、Ｎ－イソブチルカルバモイル基、Ｎ，Ｎ－ジイソブチルカルバモイル基、Ｎ－ｓｅｃ－ブチルカルバモイル基、Ｎ，Ｎ－ジｓｅｃ－ブチルカルバモイル基、Ｎ－ｔｅｒｔ－ブチルカルバモイル基、Ｎ，Ｎ－ジｔｅｒｔ－ブチルカルバモイル基、Ｎ－ペンチルカルバモイル基、Ｎ，Ｎ－ジペンチルカルバモイル基、Ｎ－（１－エチルプロピル）カルバモイル基、Ｎ，Ｎ－ジ（１－エチルプロピル）カルバモイル基、Ｎ－ヘキシルカルバモイル基、Ｎ，Ｎ－ジヘキシルカルバモイル基、Ｎ－（２－エチル）ヘキシルカルバモイル基、Ｎ，Ｎ－ジ（２－エチル）ヘキシルカルバモイル基、Ｎ－ヘプチルカルバモイル基、Ｎ，Ｎ－ジヘプチルカルバモイル基、Ｎ－オクチルカルバモイル基、Ｎ，Ｎ－ジオクチルカルバモイル基、Ｎ－ノニルカルバモイル基、Ｎ，Ｎ－ジノニルカルバモイル基、Ｎ－フェニルカルバモイル基、Ｎ，Ｎ－ジフェニルカルバモイル基、Ｎ，Ｎ－エチルメチルカルバモイル基、Ｎ，Ｎ－プロピルメチルカルバモイル基、Ｎ，Ｎ－イソプロピルメチルカルバモイル基、Ｎ，Ｎ－ブチルメチルカルバモイル基、Ｎ，Ｎ－ｔｅｒｔ－ブチルメチルカルバモイル基、及びＮ，Ｎ－フェニルメチルカルバモイル基等の１つ又は２つの炭素数１～２０、好ましくは炭素数１～１０の炭化水素基で置換されたカルバモイル基；
　＊－ＣＯＣＯＲｎｂ２；
　＊－ＯＣＯＮ（Ｒｎｂ２）２；
　＊－Ｎ（Ｒｎｂ２）ＣＯＯＲｎｂ２；等が挙げられる。
［前記式中、
　＊は、結合手を表す。
　Ｒｎｂ２は、複数個存在する場合、同一であってもよく異なっていてもよく、前記と同じ意味を表す。］ By replacing —CH 2 — contained in the hydrocarbon group with —O—, —CO—, —S (O) 2 —, —NR na —, —NR nb —, —NR na10 — or —NR nb10 —. As the group (Z) to be formed,
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 in which a hydrocarbon 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 is bonded to one side;
Epoxy groups;
Formyl group;
2 to 22 carbon atoms such as acetyl group, propanoyl group, butanoyl group, tert-butanoyl group, pentanoyl group, hexanoyl group, (2-ethyl) hexanoyl group, heptanoyl group, octanoyl group, nonanoyl group and benzoyl group, preferably Is an acyl group having 2 to 12 carbon atoms (preferably an alkanoyl group);
Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl) hexyloxycarbonyl group, heptyloxycarbonyl group and octyloxycarbonyl An oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, such as a group, nonyloxycarbonyl group, phenyloxycarbonyl group, and o-tolyloxycarbonyl group is bonded;
An 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) Xylamino 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- 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 butylmethylamino group and an N, N-phenylmethylamino group;
A 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-butylsulfur Famoyl group, N-pentylsulfamoyl group, N, N-dipentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, , N-di (1-ethylpropyl) sulfamoyl group, N-hexylsulfamoyl group, N, N-dihexylsulfamoyl group, N- (2-ethyl) hexylsulfamoyl group, N, N-di ( 2-ethyl) hexylsulfamoyl group, N-heptylsulfamoyl group, N, N-diheptylsulfamoyl group, N-octylsulfamoyl group, N, N-dioctylsulfamoyl group, N, N -Octylmethylsulfamoyl group, N-nonylsulfamoyl group, N, N-dinonylsulfamoyl group, N-phenylsulfamoyl group, N, N-diphenylsulfamoyl group, N, N-ethylmethyl Sulfamoyl group, N, N-propylmethylsulfamoyl group, N, N-isopropylmethylsulfamoyl group, N, N-butylmethylsulfamoyl group N, N-tert-butylmethylsulfamoyl group, N, N-phenylmethylsulfamoyl group and the like, or one or two hydrocarbon groups having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms Substituted sulfamoyl groups;
Formylamino group; acetylamino group, propanoylamino group, butanoylamino group, 2,2-dimethylpropanoylamino group, pentanoylamino group, hexanoylamino group, (2-ethyl) hexanoylamino group, heptanoyl 1 to 22 carbon atoms such as amino group, octanoylamino group, nonanoylamino group, decanoylamino group, undecanoylamino group, dodecanoylamino group, heicosanoylamino group, and benzoylamino group, preferably An alkanoylamino group having 1 to 12 carbon atoms;
A hydroxy group;
Formyloxy, acetoxy, propanoyloxy, butanoyloxy, 2,2-dimethylpropanoyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy An alkanoyloxy group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, such as a group, octanoyloxy group, nonanoyloxy group, and 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, preferably 1 to 10 carbon atoms, such as a sulfonyl group and a p-tolylsulfonyl group;
A carbamoyl 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) carba Yl 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-butylmethylcarbamoyl group, 1 or 2 carbons such as N-phenylmethylcarbamoyl group 1-20, preferably a carbamoyl group substituted with a hydrocarbon group having 1 to 10 carbon atoms;
* -COCOR nb2 ;
* -OCON (R nb2 ) 2 ;
* -N (R nb2 ) COOR nb2 ;
[In the above formula,
* Represents a bond.
When there are a plurality of R nb2 s , they may be the same or different and represent the same meaning as described above. ]
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される複素環基は、単環であってもよいし多環であってもよく、好ましくは環の構成要素としてヘテロ原子を含む複素環である。ヘテロ原子としては、窒素原子、酸素原子及び硫黄原子等が挙げられる。
　上記複素環基の炭素数は、好ましくは２～３０であり、より好ましくは３～２２であり、さらに好ましくは３～２０であり、さらにより好ましくは３～１８であり、より一層好ましくは３～１５であり、特に好ましくは３～１４である。
　ａが１～１０のいずれかの整数である場合において、Ｒ１～Ｒ９、Ｒ２１～Ｒ２４、Ｒｎａ及びＲｎａ１で表される複素環基は、－ＣＯ２ －及び－Ｓ（Ｏ）２Ｏ－からなる群より選ばれる少なくとも一種を有していてもよい。 R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 The heterocyclic group represented by R na10 and R nb10 may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a hetero atom as a ring component. Examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.
The number of carbon atoms in the heterocyclic group is preferably 2-30, more preferably 3-22, still more preferably 3-20, still more preferably 3-18, and even more preferably 3 -15, particularly preferably 3-14.
When a is an integer of 1 to 10, the heterocyclic group represented by R 1 to R 9 , R 21 to R 24 , R na and R na1 is represented by —CO 2 — and —S (O ) 2 O - may have at least one selected from the group consisting of.
　窒素原子のみをヘテロ原子として含む複素環としては、アジリジン、アゼチジン、ピロリジン、ピペリジン及びピペラジン等の単環系飽和複素環；２，５－ジメチルピロール等のピロール、２－メチルピラゾール及び３－メチルピラゾール等のピラゾール、並びに、イミダゾール、１，２，３－トリアゾール及び１，２，４－トリアゾール等の５員環系不飽和複素環；ピリジン、ピリダジン及び６－メチルピリミジン等のピリミジン、ピラジン、並びに、１，３，５－トリアジン等の６員環系不飽和複素環；インダゾール、インドリン、イソインドリン、インドール、インドリジン、ベンゾイミダゾール、キノリン、イソキノリン、５，６，７，８－テトラヒドロ（３－メチル）キノキサリン及び３－メチルキノキサリン等のキノキサリン、キナゾリン、シンノリン、フタラジン、ナフチリジン、プリン、プテリジン、ベンゾピラゾール、並びに、ベンゾピペリジン等の縮合二環系複素環；カルバゾール、アクリジン及びフェナジン等の縮合三環系複素環；下記式で表される環等が挙げられる。 Heterocycles containing only nitrogen atoms as heteroatoms include monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; pyrroles such as 2,5-dimethylpyrrole, 2-methylpyrazole and 3-methylpyrazole And 5-membered unsaturated heterocyclic rings such as imidazole, 1,2,3-triazole and 1,2,4-triazole; pyrimidines such as pyridine, pyridazine and 6-methylpyrimidine, pyrazines, and 6-membered unsaturated heterocycles such as 1,3,5-triazine; indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7,8-tetrahydro (3-methyl ) Quinoxalines such as quinoxaline and 3-methylquinoxaline Condensed bicyclic heterocycles such as quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole and benzopiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; rings represented by the following formula Is mentioned.
Figure JPOXMLDOC01-appb-I000021
［式中、＊は結合手を表す。］
Figure JPOXMLDOC01-appb-I000021
[In the formula, * represents a bond. ]
　酸素原子のみをヘテロ原子として含む複素環としては、オキシラン、オキセタン、テトラヒドロフラン、テトラヒドロピラン、１，３－ジオキサン、１，４－ジオキサン、及び１－シクロペンチルジオキソラン等の単環系飽和複素環；１，４－ジオキサスピロ［４．５］デカン、及び１，４－ジオキサスピロ［４．５］ノナン等の二環系飽和複素環；α－アセトラクトン、β－プロピオラクトン、γ－ブチロラクトン、及びδ－バレロラクトン等のラクトン系複素環；２，３－ジメチルフラン、及び２，５－ジメチルフラン等のフラン等の５員環系不飽和複素環；２Ｈ－ピラン、及び４Ｈ－ピラン等の６員環系不飽和複素環；１－ベンゾフラン、及び４－メチルベンゾピラン等のベンゾピラン、ベンゾジオキソール、クロマン、並びに、イソクロマン等の縮合二環系複素環；キサンテン、及びジベンゾフラン等の縮合三環系複素環；等が挙げられる。 Heterocycles containing only oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as oxirane, oxetane, tetrahydrofuran, tetrahydropyran, 1,3-dioxane, 1,4-dioxane, and 1-cyclopentyldioxolane; Bicyclic saturated heterocycles such as 4-dioxaspiro [4.5] decane and 1,4-dioxaspiro [4.5] nonane; α-acetolactone, β-propiolactone, γ-butyrolactone, and δ-valero Lactone heterocycles such as lactones; 5-membered unsaturated heterocycles such as furans such as 2,3-dimethylfuran and 2,5-dimethylfuran; 6-membered ring systems such as 2H-pyran and 4H-pyran Unsaturated heterocycles; benzopyrans such as 1-benzofuran and 4-methylbenzopyran, benzodioxole, chroman, and iso Fused bicyclic heterocycle of Roman like; xanthene, and fused tricyclic heterocyclic ring such as dibenzofuran; and the like.
　硫黄原子のみをヘテロ原子として含む複素環としては、ジチオラン等の５員環系飽和複素環；チアン、１，３－ジチアン、及び２－メチル１，３－ジチアン等の６員環系飽和複素環；３－メチルチオフェン、及び２－カルボキシチオフェン等のチオフェン、４Ｈ－チオピラン、並びに、ベンゾテトラヒドロチオピラン等のベンゾチオピラン等の５員環系不飽和複素環；ベンゾチオフェン等の縮合二環系複素環等；チアントレン、及びジベンゾチオフェン等の縮合三環系複素環；等が挙げられる。 Heterocycles containing only sulfur atoms as heteroatoms include 5-membered saturated heterocycles such as dithiolane; 6-membered saturated heterocycles such as thiane, 1,3-dithiane, and 2-methyl-1,3-dithiane A 5-membered unsaturated heterocyclic ring such as thiophene such as 3-methylthiophene and 2-carboxythiophene, 4H-thiopyran, and benzothiopyran such as benzotetrahydrothiopyran; a condensed bicyclic heterocyclic ring such as benzothiophene; Condensed tricyclic heterocycles such as thianthrene and dibenzothiophene; and the like.
　窒素原子及び酸素原子をヘテロ原子として含む複素環としては、モルホリン、２－ピロリドン、２－メチル－２－ピロリドン、２－ピペリドン、２－メチル－２－ピペリドン等の単環系飽和複素環；４－メチルオキサゾール等のオキサゾール、２－メチルイソオキサゾール、３－メチルイソオキサゾール等のイソオキサゾール等の単環系不飽和複素環；ベンゾオキサゾール、ベンゾイソオキサゾール、ベンゾオキサジン、ベンゾジオキサン、ベンゾイミダゾリン等の縮合二環系複素環；フェノキサジン等の縮合三環系複素環；等が挙げられる。 Heterocycles containing nitrogen and oxygen atoms as heteroatoms include monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone, 2-methyl-2-piperidone; 4 -Monocyclic unsaturated heterocycles such as oxazoles such as methyloxazole, isoxazoles such as 2-methylisoxazole and 3-methylisoxazole; condensations such as benzoxazole, benzisoxazole, benzoxazine, benzodioxan and benzimidazoline Bicyclic heterocycles; condensed tricyclic heterocycles such as phenoxazine; and the like.
　窒素原子及び硫黄原子をヘテロ原子として含む複素環としては、３－メチルチアゾール、及び２，４－ジメチルチアゾール等のチアゾール等の単環系複素環；ベンゾチアゾール等の縮合二環系複素環；フェノチアジン等の縮合三環系複素環；等が挙げられる。 Heterocycles containing nitrogen and sulfur atoms as heteroatoms include monocyclic heterocycles such as 3-methylthiazole and thiazole such as 2,4-dimethylthiazole; condensed bicyclic heterocycles such as benzothiazole; phenothiazine Condensed tricyclic heterocycles such as; and the like.
　上記複素環基は、上記に挙げた炭化水素基を組み合わせた基であってもよく、例えば、テトラヒドロフリルメチル基、メチルテトラヒドロフリル基等が挙げられる。
　なお、上記の複素環の結合位は、各環に含まれる任意の水素原子が脱離した部分である。 The heterocyclic group may be a group obtained by combining the hydrocarbon groups listed above, and examples thereof include a tetrahydrofurylmethyl group and a methyltetrahydrofuryl group.
In addition, the bonding position of the above heterocyclic ring is a portion from which an arbitrary hydrogen atom contained in each ring is eliminated.
　ａが１～１０のいずれかの整数である場合、Ｒ１～Ｒ９、Ｒ１ａ～Ｒ９ａ、Ｒ２１～Ｒ２４で表される複素環基は、環を構成しない－ＣＨ２－を含むとき、該－ＣＨ２－が、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－又は－ＮＲｎａ－に置き換わっていてもよく、この場合、該複素環基は、上記基（Ｚ）を含む。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。
　ａが０である場合、Ｒ１～Ｒ５、Ｒ７、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒ１７ｂ～Ｒ２４ｂで表される複素環基は、環を構成しない－ＣＨ２－を含むとき、該－ＣＨ２－が、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－又は－ＮＲｎｂ－に置き換わっていてもよく、この場合、該複素環基は、上記基（Ｚ）を含む。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。
　Ｒｎａ１で表される複素環基は、環を構成しない－ＣＨ２－を含むとき、該－ＣＨ２－が、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－又は－ＮＲｎａ１０－に置き換わっていてもよく、この場合、該複素環基は、上記基（Ｚ）を含む。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。
　Ｒｎｂ１で表される環を構成しない－ＣＨ２－を含むとき、該－ＣＨ２－が、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－又は－ＮＲｎｂ１０－に置き換わっていてもよく、この場合、該複素環基は、上記基（Ｚ）を含む。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。 When a is an integer of 1 to 10, the heterocyclic group represented by R 1 to R 9 , R 1a to R 9a , R 21 to R 24 includes —CH 2 — that does not form a ring. In some cases, the —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —, in which case the heterocyclic group is the group (Z) including. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
When a is 0, the heterocyclic group represented by R 1 to R 5 , R 7 , R 11b to R 15b , R 1b to R 5b , R 7b , R 17b to R 24b does not form a ring— When CH 2 — is included, the —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR nb —, in which case the heterocyclic group is The group (Z) is included. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
When the heterocyclic group represented by R na1 contains —CH 2 — that does not constitute a ring, —CH 2 — represents —O—, —CO—, —S (O) 2 —, or —NR na10 —. In this case, the heterocyclic group includes the group (Z). However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
When —CH 2 — that does not constitute the ring represented by R nb1 is included, the —CH 2 — may be replaced by —O—, —CO— , —S (O) 2 —, or —NR nb10 —. In this case, the heterocyclic group includes the group (Z). However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
　また、前記複素環が、その構成元素として窒素原子を含んでいる場合、この窒素原子には、上述したＲ１が結合していてもよい。 Further, the heterocyclic ring, which may contain a nitrogen atom as its constituent elements, this nitrogen atom, R 1 as described above may be bonded.
　Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される複素環基の置換基としては、Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される炭化水素基が有していてもよい置換基と同様のものが挙げられる。 R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 The substituents of the heterocyclic group represented by R na10 and R nb10 include R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R Examples thereof include the same substituents that the hydrocarbon group represented by nb , R 17b to R 24b , R 21 to R 24 , R na1 , R nb1 , R na10, and R nb10 may have.
　Ｒ２とＲ３、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ６とＲ７、Ｒ８とＲ９、Ｒ１７ｂとＲ１８ｂ、Ｒ２１とＲ２２、Ｒ１２ｂとＲ１３ｂ、Ｒ１３ｂとＲ１４ｂ、及び、Ｒ１４ｂとＲ１５ｂ、Ｒ２ａとＲ３ａ、Ｒ３ａとＲ４ａ、Ｒ４ａとＲ５ａ、Ｒ６ａとＲ７ａ、Ｒ８ａとＲ９ａ、Ｒ２ｂとＲ３ｂ、Ｒ３ｂとＲ４ｂ、Ｒ４ｂとＲ５ｂ、Ｒ６ｂとＲ７ｂ、又はＲ２１ｂとＲ２２ｂが、各々が結合する炭素原子と一緒になって環を形成する場合、この環は、炭化水素環であってもよく、複素環であってもよい。炭化水素環としては、脂肪族炭化水素環、芳香族炭化水素環等が挙げられる。 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 17b and R 18b , R 21 and R 22 , R 12b and R 13b , R 13b R 14b , R 14b and R 15b , 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 R 5b , R 6b and R 7b , or R 21b and R 22b together with the carbon atoms to which they are attached form a ring, the ring is a hydrocarbon ring It may be a heterocyclic ring. Examples of the hydrocarbon ring include an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring.
　脂肪族炭化水素環としては、シクロプロパン環、メチルシクロプロパン環、シクロブタン環、シクロペンタン環、シクロヘキサン環、シクロヘプタン環、メチルシクロヘキサン環、１，１－ジメチルシクロヘキサン環、１，２－ジメチルシクロヘキサン環、１，３－ジメチルシクロヘキサン環、１，４－ジメチルシクロヘキサン環、シクロオクタン環、１，３，５－トリメチルシクロヘキサン環、１，１，３，３－テトラメチルシクロヘキサン環、ペンチルシクロヘキサン環、オクチルシクロヘキサン環、及びシクロヘキシルシクロヘキサン環等のシクロアルカン環；シクロヘキセン環、シクロヘプテン環、及びシクロオクテン環等のシクロアルケン環；ノルボルナン、アダマンタン、及びビシクロ［２．２．２］オクタン等が挙げられる。
　脂肪族炭化水素環の炭素数は、例えば、３～３０であり、好ましくは３～２０であり、より好ましくは４～２０であり、さらに好ましくは４～１５であり、さらにより好ましくは５～１５であり、特に好ましくは５～１０である。 Aliphatic hydrocarbon rings include cyclopropane ring, methylcyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, methylcyclohexane ring, 1,1-dimethylcyclohexane ring, 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 And cycloalkane rings such as cyclohexylcyclohexane ring; cycloalkene rings such as cyclohexene ring, cycloheptene ring, and cyclooctene ring; norbornane, adamantane, and bicyclo [2.2.2] octane.
The carbon number of the aliphatic hydrocarbon ring is, for example, 3 to 30, preferably 3 to 20, more preferably 4 to 20, still more preferably 4 to 15, and still more preferably 5 to 15, particularly preferably 5 to 10.
　芳香族炭化水素環としては、ベンゼン、トルエン、ｏ－キシレン、ｍ－キシレン、ｐ－キシレン、イソプロピルベンゼン、ｔｅｒｔ－ブチルベンゼン、メシチレン、１，５－ビス（２－プロピル）ベンゼン、ナフタレン、１，２，３，４－テトラヒドロナフタレン、フルオレン、フェナントレン、及びアントラセン；等が挙げられる。
　芳香族炭化水素環の炭素数は、例えば、６～３０であり、好ましくは６～２０であり、より好ましくは６～１５である。 Aromatic hydrocarbon rings include benzene, toluene, o-xylene, m-xylene, p-xylene, isopropylbenzene, tert-butylbenzene, mesitylene, 1,5-bis (2-propyl) benzene, naphthalene, 1, 2,3,4-tetrahydronaphthalene, fluorene, phenanthrene, and anthracene;
The number of carbon atoms in the aromatic hydrocarbon ring is, for example, 6 to 30, preferably 6 to 20, and more preferably 6 to 15.
　Ｒ２とＲ３、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ６とＲ７、Ｒ８とＲ９、Ｒ１７ｂとＲ１８ｂ、Ｒ２１とＲ２２、Ｒ１２ｂとＲ１３ｂ、Ｒ１３ｂとＲ１４ｂ、Ｒ１４ｂとＲ１５ｂ、Ｒ２ａとＲ３ａ、Ｒ３ａとＲ４ａ、Ｒ４ａとＲ５ａ、Ｒ６ａとＲ７ａ、Ｒ８ａとＲ９ａ、Ｒ２ｂとＲ３ｂ、Ｒ３ｂとＲ４ｂ、Ｒ４ｂとＲ５ｂ、Ｒ６ｂとＲ７ｂ、又はＲ２１ｂとＲ２２ｂが、各々が結合する炭素原子と一緒になって環を形成する場合、該環は、置換基を有していてもよい。該置換基としては、Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される炭化水素基が有していてもよい置換基と同様のものが挙げられる。 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 17b and R 18b , R 21 and R 22 , R 12b and R 13b , R 13b And R 14b , R 14b and R 15b , 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 R 5b , R 6b and R 7b , or R 21b and R 22b together with the carbon atoms to which they are attached form a ring, the ring has a substituent Also good. Examples of the substituent include R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24. , R na1 , R nb1 , R na10 and R nb10 are the same as the substituents which the hydrocarbon group represented by Rnb10 may have.
　Ｒ２とＲ３、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ６とＲ７、Ｒ８とＲ９、Ｒ１７ｂとＲ１８ｂ、Ｒ２１とＲ２２、Ｒ１２ｂとＲ１３ｂ、Ｒ１３ｂとＲ１４ｂ、及び、Ｒ１４ｂとＲ１５ｂ、Ｒ２ａとＲ３ａ、Ｒ３ａとＲ４ａ、Ｒ４ａとＲ５ａ、Ｒ６ａとＲ７ａ、Ｒ８ａとＲ９ａ、Ｒ２ｂとＲ３ｂ、Ｒ３ｂとＲ４ｂ、Ｒ４ｂとＲ５ｂ、Ｒ６ｂとＲ７ｂ、又はＲ２１ｂとＲ２２ｂが、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する場合であって、該環が環を構成しない－ＣＨ２－を含むとき、該－ＣＨ２－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－、－ＮＲｎａ－又は－ＮＲｎｂ－に置き換わっていてもよく、この場合、該環は、上記基（Ｚ）を含む。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 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 17b and R 18b , R 21 and R 22 , R 12b and R 13b , R 13b R 14b , R 14b and R 15b , 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 R 5b , R 6b and R 7b , or R 21b and R 22b together with the carbon atoms to which they are bonded form a ring that may have a substituent. And when the ring contains —CH 2 —, which does not constitute a ring, —CH 2 — means —O—, —CO—, —S (O) 2 —, —NR na — or —NR nb —. In this case, the ring contains the group (Z). However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
　Ｒ２とＲ３、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ６とＲ７、Ｒ８とＲ９、Ｒ１７ｂとＲ１８ｂ、Ｒ２１とＲ２２、Ｒ１２ｂとＲ１３ｂ、Ｒ１３ｂとＲ１４ｂ、Ｒ１４ｂとＲ１５ｂ、Ｒ２ａとＲ３ａ、Ｒ３ａとＲ４ａ、Ｒ４ａとＲ５ａ、Ｒ６ａとＲ７ａ、Ｒ８ａとＲ９ａ、Ｒ２ｂとＲ３ｂ、Ｒ３ｂとＲ４ｂ、Ｒ４ｂとＲ５ｂ、Ｒ６ｂとＲ７ｂ、又はＲ２１ｂとＲ２２ｂが、各々が結合する炭素原子と一緒になって環を形成する場合、該環は、複素環であってもよい。
　Ｒ２とＲ３、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ１２ｂとＲ１３ｂ、Ｒ１３ｂとＲ１４ｂ、Ｒ１４ｂとＲ１５ｂ、Ｒ２ａとＲ３ａ、Ｒ３ａとＲ４ａ、Ｒ４ａとＲ５ａ、Ｒ２ｂとＲ３ｂ、Ｒ３ｂとＲ４ｂ、又はＲ４ｂとＲ５ｂが、各々が結合する炭素原子と一緒になって環を形成する場合、該複素環基は、Ｒ２～Ｒ５、Ｒ１２ｂ～Ｒ１５ｂ、Ｒ２ａ～Ｒ５ａ、又はＲ２ｂ～Ｒ５ｂが結合するベンゼン環と共に２環以上の環構造を有している。この２環以上の環構造を有する複素環としては、例えば、下記式の構造を有する複素環が挙げられる。 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 17b and R 18b , R 21 and R 22 , R 12b and R 13b , R 13b And R 14b , R 14b and R 15b , 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 When 4b , R4b and R5b , R6b and R7b , or R21b and R22b together with the carbon atoms to which they are attached form a ring, the ring may be a heterocycle .
R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 12b and R 13b , R 13b and R 14b , R 14b and R 15b , R 2a and R 3a , R 3a and R 4a , R 4a and if R 5a, R 2b and R 3b, R 3b and R 4b, or R 4b and R 5b together with the carbon atom to which each is attached to form a ring, said heterocyclic groups, R 2 ~ It has a ring structure of two or more rings together with a benzene ring to which R 5 , R 12b to R 15b , R 2a to R 5a , or R 2b to R 5b are bonded. Examples of the heterocyclic ring having two or more ring structures include a heterocyclic ring having a structure of the following formula.
Figure JPOXMLDOC01-appb-I000022
［式中のベンゼン環は、式（Ｉ）で表される化合物が有するイソインドリン構造中のベンゼン環に相当する。］
Figure JPOXMLDOC01-appb-I000022
[The benzene ring in the formula corresponds to the benzene ring in the isoindoline structure of the compound represented by the formula (I). ]
　Ｒ１～Ｒ９、Ｒ１７ｂ及びＲ１８ｂの少なくとも１つ、好ましくはＲ６～Ｒ９、Ｒ１７ｂ及びＲ１８ｂの少なくとも１つ、より好ましくはＲ６及びＲ７の一方と、Ｒ８及びＲ９の一方、又はＲ６及びＲ７の一方と、Ｒ１７ｂ及びＲ１８ｂの一方は、炭化水素基であることが好ましい。
　Ｒ１１ｂ～Ｒ１６ｂ、Ｒ２１ｂ及びＲ２２ｂの少なくとも１つ、好ましくはＲ１６ｂ、Ｒ２１ｂ及びＲ２２ｂの少なくとも１つ、より好ましくはＲ１６ｂと、Ｒ２１ｂ及びＲ２２ｂの一方は、炭化水素基であることが好ましい。
　Ｒ１ａ～Ｒ９ａの少なくとも１つ、好ましくはＲ６ａ～Ｒ９ａの少なくとも１つ、より好ましくはＲ６ａ及びＲ７ａの一方とＲ８ａ及びＲ９ａの一方は、炭化水素基であることが好ましい。
　Ｒ１ｂ～Ｒ７ｂ、Ｒ１７ｂ及びＲ１８ｂの少なくとも１つ、好ましくはＲ６ｂ、Ｒ７ｂ、Ｒ１７ｂ及びＲ１８ｂの少なくとも１つ、より好ましくはＲ６ｂ及びＲ７ｂの一方と、Ｒ１７ｂ及びＲ１８ｂの一方は、炭化水素基であることが好ましい。 At least one of R 1 to R 9 , R 17b and R 18b , preferably at least one of R 6 to R 9 , R 17b and R 18b , more preferably one of R 6 and R 7 , R 8 and R One of 9 , or one of R 6 and R 7 and one of R 17b and R 18b are preferably a hydrocarbon group.
At least one of R 11b to R 16b , R 21b and R 22b , preferably at least one of R 16b , R 21b and R 22b , more preferably R 16b and one of R 21b and R 22b is a hydrocarbon group It is preferable that
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 is preferably a hydrocarbon group. .
At least one of R 1b to R 7b , R 17b and R 18b , preferably at least one of R 6b , R 7b , R 17b and R 18b , more preferably one of R 6b and R 7b , and R 17b and R One of 18b is preferably a hydrocarbon group.
　－ＣＯ－ＯＲｎａ１、－ＣＯ－ＯＲｎｂ１としては、メトキシカルボニル基、エトキシカルボニル基、プロポキシカルボニル基、ｔｅｒｔ－ブトキシカルボニル基、ブトキシカルボニル基、ペンチルオキシカルボニル基、ヘキシルオキシカルボニル基、（２－エチル）ヘキシルオキシカルボニル基、ヘプチルオキシカルボニル基、オクチルオキシカルボニル基、ノニルオキシカルボニル基、デシルオキシカルボニル基、ウンデシルオキシカルボニル基、ドデシルオキシカルボニル基、フェニルオキシカルボニル基及びイコシルオキシカルボニル基等の炭素数１～３５の炭化水素基が結合したオキシカルボニル基等が好ましく、より好ましくは炭素数１～１０の炭化水素基が結合したオキシカルボニル基等が挙げられる。 As —CO—OR na1 and —CO—OR nb1 , methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl ) Carbons such as hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, undecyloxycarbonyl group, dodecyloxycarbonyl group, phenyloxycarbonyl group and icosyloxycarbonyl group An oxycarbonyl group to which a hydrocarbon group of 1 to 35 is bonded is preferable, and an oxycarbonyl group to which a hydrocarbon group of 1 to 10 carbons is bonded is more preferable.
　－ＣＯ－ＮＨ（Ｒｎａ１）、－ＣＯ－Ｎ（Ｒｎａ１）２、－ＣＯ－ＮＨ（Ｒｎｂ１）、－ＣＯ－Ｎ（Ｒｎｂ１）２としては、Ｎ－メチルカルバモイル基、Ｎ－エチルカルバモイル基、Ｎ－プロピルカルバモイル基、Ｎ－イソプロピルカルバモイル基、Ｎ－ブチルカルバモイル基、Ｎ－イソブチルカルバモイル基、Ｎ－ｓｅｃ－ブチルカルバモイル基、Ｎ－ｔｅｒｔ－ブチルカルバモイル基、Ｎ－ペンチルカルバモイル基、Ｎ－（１－エチルプロピル）カルバモイル基、Ｎ－ヘキシルカルバモイル基、Ｎ－（２－エチル）ヘキシルカルバモイル基、Ｎ－ヘプチルカルバモイル基、Ｎ－オクチルカルバモイル基、Ｎ－ノニルカルバモイル基、Ｎ－デシルカルバモイル基、Ｎ－ウンデシルカルバモイル基、Ｎ－ドデシルカルバモイル基、Ｎ－イコシルカルバモイル基及びＮ－フェニルカルバモイル基等の１つの炭素数１～３５の炭化水素基で置換されたカルバモイル基等；
　Ｎ，Ｎ－ジメチルカルバモイル基、Ｎ，Ｎ－エチルメチルカルバモイル基、Ｎ，Ｎ－ジエチルカルバモイル基、Ｎ，Ｎ－プロピルメチルカルバモイル基、Ｎ，Ｎ－ジプロピルカルバモイル基、Ｎ，Ｎ－イソプロピルメチルカルバモイル基、Ｎ，Ｎ－ジイソプロピルカルバモイル基、Ｎ，Ｎ－ｔｅｒｔ－ブチルメチルカルバモイル基、Ｎ，Ｎ－ジイソブチルカルバモイル基、Ｎ，Ｎ－ジｓｅｃ－ブチルカルバモイル基、Ｎ，Ｎ－ジｔｅｒｔ－ブチルカルバモイル基、Ｎ，Ｎ－ブチルメチルカルバモイル基、Ｎ，Ｎ－ジブチルカルバモイル基、Ｎ，Ｎ－ブチルオクチルカルバモイル基、Ｎ，Ｎ－ジペンチルカルバモイル基、Ｎ，Ｎ－ジ（１－エチルプロピル）カルバモイル基、Ｎ，Ｎ－ジヘキシルカルバモイル基、Ｎ，Ｎ－ジ（２－エチル）ヘキシルカルバモイル基、Ｎ，Ｎ－ジヘプチルカルバモイル基、Ｎ，Ｎ－オクチルメチルカルバモイル基、Ｎ，Ｎ－ジオクチルカルバモイル基、Ｎ，Ｎ－ジノニルカルバモイル基、Ｎ，Ｎ－デシルメチルカルバモイル基、Ｎ，Ｎ－ウンデシルメチルカルバモイル基、Ｎ，Ｎ－ドデシルメチルカルバモイル基、Ｎ，Ｎ－イコシルメチルカルバモイル基、Ｎ，Ｎ－フェニルメチルカルバモイル基及びＮ，Ｎ－ジフェニルカルバモイル基等の２つの炭素数１～３５の炭化水素基で置換されたカルバモイル基等が好ましく、より好ましくは１つ又は２つの炭素数１～１０の炭化水素基で置換されたカルバモイル基等が挙げられる。 —CO—NH (R na1 ), —CO—N (R na1 ) 2 , —CO—NH (R nb1 ), —CO—N (R nb1 ) 2 include an 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-hexylcarbamoyl group, N- (2-ethyl) hexylcarbamoyl group, N-heptylcarbamoyl group, N-octylcarbamoyl group, N-nonylcarbamoyl group, N-decylcarbamoyl group, N-undecylcarbamoyl group, N-dodecylcarbamoyl group, N Lee waist carbamoyl group and N-1 single carbamoyl group substituted with a hydrocarbon group having 1 to 35 carbon atoms in the phenylcarbamoyl group and the like;
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) hexyl Rucarbamoyl group, N, N-diheptylcarbamoyl group, N, N-octylmethylcarbamoyl group, N, N-dioctylcarbamoyl group, N, N-dinonylcarbamoyl group, N, N-decylmethylcarbamoyl group, N, N -Two carbon atoms such as undecylmethylcarbamoyl group, N, N-dodecylmethylcarbamoyl group, N, N-icosylmethylcarbamoyl group, N, N-phenylmethylcarbamoyl group, N, N-diphenylcarbamoyl group, etc. A carbamoyl group substituted with 35 hydrocarbon groups is preferred, and a carbamoyl group substituted with one or two hydrocarbon groups having 1 to 10 carbon atoms is more preferred.
　－ＣＯ－Ｒｎａ１、－ＣＯ－Ｒｎｂ１としては、アセチル基、プロパノイル基、ブタノイル基、２，２－ジメチルプロパノイル基、ペンタノイル基、ヘキサノイル基、（２－エチル）ヘキサノイル基、ヘプタノイル基、オクタノイル基、ノナノイル基、デカノイル基、ウンデカノイル基、ドデカノイル基、ヘンイコサノイル基、ベンゾイル基、フェニルメチルカルボニル基、フェニルエチルカルボニル基及びフェニルプロピルカルボニル基等の炭化水素基であって炭素数が１～３５の基が結合したカルボニル基が好ましく、好ましくは炭化水素基であって炭素数が１～１０の基が結合したカルボニル基等が挙げられる。
　炭化水素基が結合したカルボニル基である－ＣＯ－Ｒｎａ１、－ＣＯ－Ｒｎｂ１において、該炭化水素基が、塩素原子等のハロゲン原子；スルファモイル基；ヒドロキシ基；メトキシ基等の炭素数１～１０の炭化水素基が片側に結合したオキシ基；メトキシカルボニル基等の炭素数１～１０の炭化水素基が結合したオキシカルボニル基；等を有していてもよい。
　－ＣＯ－Ｒｎａ１において、炭化水素基が結合したカルボニル基では、該炭化水素基が－ＣＯ２ －及び－Ｓ（Ｏ）２Ｏ－等を有していてもよい。 —CO—R na1 and —CO—R nb1 include acetyl group, propanoyl group, butanoyl group, 2,2-dimethylpropanoyl group, pentanoyl group, hexanoyl group, (2-ethyl) hexanoyl group, heptanoyl group, octanoyl A hydrocarbon group such as a group, nonanoyl group, decanoyl group, undecanoyl group, dodecanoyl group, henicosanoyl group, benzoyl group, phenylmethylcarbonyl group, phenylethylcarbonyl group and phenylpropylcarbonyl group, and having 1 to 35 carbon atoms A carbonyl group to which is bonded is preferable, and a carbonyl group to which a group having 1 to 10 carbon atoms is bonded is preferable.
In —CO—R na1 and —CO—R nb1 which are carbonyl groups to which a hydrocarbon group is bonded, the hydrocarbon group is a halogen atom such as a chlorine atom; a sulfamoyl group; a hydroxy group; An oxy group having 10 hydrocarbon groups bonded to one side; an oxycarbonyl group having 1 to 10 carbon atoms such as a methoxycarbonyl group bonded; and the like.
In —CO—R na1 , in the carbonyl group to which a hydrocarbon group is bonded, the hydrocarbon group may have —CO 2 —, —S (O) 2 O —, and the like.
　－Ｓ（Ｏ）２－Ｒｎａ１、－Ｓ（Ｏ）２－Ｒｎｂ１としては、メチルスルホニル基、エチルスルホニル基、プロピルスルホニル基、ブチルスルホニル基、ペンチルスルホニル基、ヘキシルスルホニル基、（２－エチル）ヘキシルスルホニル基、ヘプチルスルホニル基、オクチルスルホニル基、ノニルスルホニル基、デシルスルホニル基、ウンデシルスルホニル基、ドデシルスルホニル基、イコシルスルホニル基、フェニルスルホニル基、及びｐ－トリルスルホニル基等の炭素数１～３５の炭化水素基が結合したスルホニル基等が好ましく、より好ましくは炭素数１～１０の炭化水素基が結合したスルホニル基等が挙げられる。 As —S (O) 2 —R na1 and —S (O) 2 —R nb1 , methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl ) 1 carbon number such as hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, icosylsulfonyl group, phenylsulfonyl group, and p-tolylsulfonyl group A sulfonyl group to which a hydrocarbon group of ˜35 is bonded is preferable, and a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms is bonded is more preferable.
　Ｒ２とＲ３、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ１２ｂとＲ１３ｂ、Ｒ１３ｂとＲ１４ｂ、Ｒ１４ｂとＲ１５ｂ、Ｒ２ａとＲ３ａ、Ｒ３ａとＲ４ａ、Ｒ４ａとＲ５ａ、Ｒ２ｂとＲ３ｂ、Ｒ３ｂとＲ４ｂ、又はＲ４ｂとＲ５ｂが、各々が結合する炭素原子と一緒になって形成してもよい環は、式（Ｉ）、式（ＩＩＢ）、式（ＩＡ）、又は式（ＩＢ）のイソインドリン骨格のベンゼン環と縮合している。
　Ｒ２とＲ３、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ１２ｂとＲ１３ｂ、Ｒ１３ｂとＲ１４ｂ、Ｒ１４ｂとＲ１５ｂ、Ｒ２ａとＲ３ａ、Ｒ３ａとＲ４ａ、Ｒ４ａとＲ５ａ、Ｒ２ｂとＲ３ｂ、Ｒ３ｂとＲ４ｂ、又はＲ４ｂとＲ５ｂが、各々が結合する炭素原子と一緒になって形成してもよい環と前記ベンゼン環との縮合環構造としては、インデン、ナフタレン、ビフェニレン、インダセン、アセナフチレン、フルオレン、フェナレン、フェナントレン、アントラセン、フルオランテン、アセフェナントリレン、アセアントリレン、トリフェニレン、ピレン、クリセン、Ｎ－メチルフタルイミド、Ｎ－（１－フェニルエチル）フタルイミド及びテトラセン等の炭化水素系縮環構造及びその部分還元体（例えば、９，１０－ジヒドロアントラセン、１，２，３，４－テトラヒドロナフタレン等）；インドール、イソインドール、インダゾール、キノリン、イソキノリン、フタラジン、キノキサリン、キナゾリン、シンノリン、カルバゾール、カルボリン、フェナントリジン、アクリジン、ペリミジン、フェナントロリン、フェナジン等の含窒素縮合複素環及びその部分還元体；３－ヒドロベンゾフラン２－オン等の含酸素縮合複素環及びその部分還元体が挙げられる。 R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 12b and R 13b , R 13b and R 14b , R 14b and R 15b , 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 , or R 4b and R 5b may be formed together with the carbon atoms to which each is bonded, are represented by formula (I), formula ( IIB), condensed with the benzene ring of the isoindoline skeleton of formula (IA) or formula (IB).
R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 12b and R 13b , R 13b and R 14b , R 14b and R 15b , 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 , or R 4b and R 5b may be formed together with the carbon atom to which each is bonded, and the condensed ring structure of the benzene ring As indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrylene, acanthrylene, triphenylene, pyrene, chrysene, N-methylphthalimide, N- (1-phenylethyl) ) Hydrocarbon-based condensed ring structures such as phthalimide and tetracene and partially reduced products thereof (for example, 9,10-dihydro) Indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, perimidine, phenanthroline, phenazine, etc. And nitrogen-containing condensed heterocyclic rings and partially reduced products thereof; oxygen-containing condensed heterocyclic rings such as 3-hydrobenzofuran-2-one and partially reduced products thereof.
　Ｒ６ａとＲ７ａ、又はＲ８ａとＲ９ａが、各々が結合する炭素原子と一緒になって形成してもよい環は、式（ＩＡ）のイソインドリン骨格のエキソメチレン（Ｃ＝ＣＨ２）と結合しており、該環をこのエキソメチレン（Ｃ＝ＣＨ２）を含んだ構造として挙げると、例えば、下記群Ａの様なカルボニル基とエキソメチレンとカルボニル基とがこの順で並ぶ構造が例示できる。＊＊は、イソインドリン骨格との結合手を表す。 The ring that R 6a and R 7a , or R 8a and R 9a may form together with the carbon atoms to which each is bonded is an exomethylene (C═CH 2 ) of the isoindoline skeleton of formula (IA) When the ring is exemplified as a structure containing this exomethylene (C═CH 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. It can be illustrated. ** represents a bond to the isoindoline skeleton.
　［群Ａ］
Figure JPOXMLDOC01-appb-I000023
[Group A]
Figure JPOXMLDOC01-appb-I000023
［式中、Ｒ２５及びＲ２６は、互いに独立に、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、又は水素原子を表し、該炭化水素基に含まれる－ＣＨ２－は、－Ｏ－、－ＣＯ－、－Ｓ（Ｏ）２－又は－ＮＲｎａ－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。該炭化水素基及び該複素環基は、置換基として－ＣＯ２ －及び－Ｓ（Ｏ）２Ｏ－からなる群より選ばれる少なくとも一種を有していてもよい。Ｒ２５、Ｒ２６の具体例及び好ましい例は、Ｒｎａ１と同様である。］ [Wherein, R 25 and R 26 are each independently 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. And —CH 2 — contained in the hydrocarbon group may be replaced by —O—, —CO—, —S (O) 2 —, or —NR na —. However, —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —. 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 — as a substituent. Specific examples and preferred examples of R 25 and R 26 are the same as those of R na1 . ]
　Ｒ２１とＲ２２が、各々が結合する炭素原子と一緒になって形成してもよい環は、式（Ｉ）のイソインドリン骨格のエキソメチレン（Ｃ＝ＣＨ２）と結合しており、該環をこのエキソメチレン（Ｃ＝ＣＨ２）を含んだ構造として挙げると、例えば、下記群Ｂの様なカルボニル基とエキソメチレンとカルボニル基とがこの順で並ぶ構造が例示できる。＊＊は、イソインドリン骨格との結合手を表す。 The ring which R 21 and R 22 may form together with the carbon atom to which each is bonded is bonded to the isoindoline skeleton of formula (I) (C═CH 2 ), When the ring is exemplified as a structure containing this exomethylene (C═CH 2 ), for example, a structure in which a carbonyl group, an exomethylene, and a carbonyl group are arranged in this order as shown in the following group B can be exemplified. ** represents a bond to the isoindoline skeleton.
　［群Ｂ］
Figure JPOXMLDOC01-appb-I000024
［式中、Ｒ２３及びＲ２４は、前記と同じ意味を表す。］ [Group B]
Figure JPOXMLDOC01-appb-I000024
[Wherein R 23 and R 24 represent the same meaning as described above. ]
　Ｒ１７ｂとＲ１８ｂ、又はＲ２１ｂとＲ２２ｂが、各々が結合する炭素原子と一緒になって形成してもよい環は、式（ＩＩＢ）のイソインドリン骨格のエキソメチレン（Ｃ＝ＣＨ２）と結合しており、該環をこのエキソメチレン（Ｃ＝ＣＨ２）を含んだ構造として挙げると、例えば、下記群Ｃの様なカルボニル基とエキソメチレンとカルボニル基とがこの順で並ぶ構造が例示できる。＊＊は、イソインドリン骨格との結合手を表す。 The ring that R 17b and R 18b , or R 21b and R 22b may form together with the carbon atoms to which each is bonded is an exomethylene (C═CH 2 ) of the isoindoline skeleton of formula (IIB). When the ring is exemplified as a structure containing this exomethylene (C═CH 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 C below. It can be illustrated. ** represents a bond to the isoindoline skeleton.
　［群Ｃ］
Figure JPOXMLDOC01-appb-I000025
［式中、Ｒ２３ｂ及びＲ２４ｂは、前記と同じ意味を表す。］ [Group C]
Figure JPOXMLDOC01-appb-I000025
[Wherein, R 23b and R 24b represent the same meaning as described above. ]
　Ｒ２とＲ３、Ｒ３とＲ４、Ｒ４とＲ５、Ｒ１２ｂとＲ１３ｂ、Ｒ１３ｂとＲ１４ｂ、Ｒ１４ｂとＲ１５ｂ、Ｒ２ａとＲ３ａ、Ｒ３ａとＲ４ａ、Ｒ４ａとＲ５ａ、Ｒ２ｂとＲ３ｂ、Ｒ３ｂとＲ４ｂ、又はＲ４ｂとＲ５ｂが、各々が結合する炭素原子と一緒になって形成してもよい環は、置換基を有していてもよい。該置換基としては、Ｒ１～Ｒ９、Ｒ１１ｂ～Ｒ１５ｂ、Ｒ１ａ～Ｒ９ａ、Ｒ１ｂ～Ｒ５ｂ、Ｒ７ｂ、Ｒｎａ、Ｒｎｂ、Ｒ１７ｂ～Ｒ２４ｂ、Ｒ２１～Ｒ２４、Ｒｎａ１、Ｒｎｂ１、Ｒｎａ１０及びＲｎｂ１０で表される炭化水素基が有していてもよい置換基と同様のものが挙げられる。 R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 12b and R 13b , R 13b and R 14b , R 14b and R 15b , 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 , or R 4b and R 5b may be formed together with the carbon atoms to which they are bonded, each having a substituent Also good. Examples of the substituent include R 1 to R 9 , R 11b to R 15b , R 1a to R 9a , R 1b to R 5b , R 7b , R na , R nb , R 17b to R 24b , R 21 to R 24. , R na1 , R nb1 , R na10 and R nb10 are the same as the substituents which the hydrocarbon group represented by Rnb10 may have.
　Ｒ２～Ｒ９、Ｒ１７ｂ、Ｒ１８ｂ、Ｒ２１、Ｒ２２、Ｒ１２ｂ～Ｒ１５ｂ、Ｒ２１ｂ及びＲ２２ｂ、Ｒ２ａ～Ｒ９ａ、Ｒ２ｂ～Ｒ５ｂ及びＲ７ｂで表されるハロゲン原子としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子が挙げられ、好ましくは、塩素原子、臭素原子である。 Halogen atoms represented by R 2 to R 9 , R 17b , R 18b , R 21 , R 22 , R 12b to R 15b , R 21b and R 22b , R 2a to R 9a , R 2b to R 5b and R 7b Examples thereof include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a chlorine atom and a bromine atom.
　Ｍｂ＋は、ヒドロン又はＬｉ＋、Ｎａ＋、Ｋ＋等の１価の金属イオン、２価以上の金属陽イオンであることが好ましく、ヒドロン又は２価以上の金属陽イオンであることがより好ましく、ヒドロンであることがさらに好ましい。
　２価以上の金属陽イオンとしては、元素の周期律表の２族～１５族の金属の陽イオンが挙げられ、好ましくは、Ｍｇ２＋、Ｃａ２＋、Ｓｒ２＋、Ｂａ２＋、Ｃｄ２＋、Ｎｉ２＋、Ｚｎ２＋、Ｃｕ２＋、Ｈｇ２＋、Ｆｅ２＋、Ｃｏ２＋、Ｓｎ２＋、Ｐｂ２＋及びＭｎ２＋等の２価の金属陽イオン；Ａｌ３＋、Ｆｅ３＋及びＣｒ３＋等の３価の金属陽イオン；Ｓｎ４＋、Ｍｎ４＋、Ｃｅ４＋等の４価の金属陽イオンが挙げられ、より好ましくはＭｇ２＋、Ｃａ２＋、Ｓｒ２＋、Ｂａ２＋、Ｎｉ２＋、Ｚｎ２＋、Ｃｕ２＋、Ｆｅ２＋、Ｃｏ２＋、Ｓｎ２＋、Ｍｎ２＋、Ａｌ３＋、Ｆｅ３＋、Ｃｒ３＋、Ｓｎ４＋及びＭｎ４＋が挙げられ、さらに好ましくはＭｇ２＋、Ｃａ２＋、Ｓｒ２＋、Ｂａ２＋、Ｚｎ２＋、Ｃｕ２＋、Ｆｅ２＋、Ｍｎ２＋、Ａｌ３＋、Ｆｅ３＋、Ｃｒ３＋及びＭｎ４＋が挙げられる。
　なお、Ｍｂ＋がヒドロンである場合、該ヒドロンは、－ＣＯ２ －又は－Ｓ（Ｏ）２Ｏ－と結合し、－ＣＯＯＨ又は－Ｓ（Ｏ）２ＯＨとして存在する。 M b + is Hydron or Li +, Na +, 1 valent metal ions K + and the like, preferably a divalent or higher valent metal cation, more preferably Hydron or divalent or higher valent metal cation More preferred is hydrone.
Examples of the metal cation having a valence of 2 or more include cations of metals in groups 2 to 15 of the periodic table of elements, and preferably Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Cd 2+ , Ni 2+. Divalent metal cations such as Zn 2+ , Cu 2+ , Hg 2+ , Fe 2+ , Co 2+ , Sn 2+ , Pb 2+ and Mn 2+ ; trivalent metal cations such as Al 3+ , Fe 3+ and Cr 3+ ; Examples include tetravalent metal cations such as Sn 4+ , Mn 4+ , and Ce 4+ , and more preferably Mg 2+ , 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 4+ and Mn 4+ and the like, more preferably Mg 2+, Ca 2+, Sr 2+ , Ba 2 , Zn 2+, Cu 2+, Fe 2+, Mn 2+, Al 3+, Fe 3+, Cr 3+ and Mn 4+ and the like.
When M b + is hydrone, the hydrone is bonded to —CO 2 — or —S (O) 2 O — and exists as —COOH or —S (O) 2 OH.
　ａは、好ましくは０～１０のいずれかの整数であり、より好ましくは０～５のいずれかの整数であり、さらに好ましくは０又は２～４のいずれかの整数である。 A is preferably an integer of 0 to 10, more preferably an integer of 0 to 5, and further preferably an integer of 0 or 2 to 4.
　式（Ｉ）で表される化合物（Ｂ）の第１態様において、Ｒ１～Ｒ６、Ｒ２１、Ｒ２２、Ｒｎａ１、Ｒｎａ２、Ｍｂ＋、ａは、以下のとおりであることが好ましい。
　Ｒ１としては、水素原子が好ましい。
　Ｒ２～Ｒ５としては、水素原子；ブチル基等の炭素数１～１０のアルキル基；メトキシ基等の炭素数１～１０のアルコキシ基；トリフルオロメチル基等のアルキル基に含まれる水素原子の全てがフッ素原子に置き換わった基；塩素原子、臭素原子等のハロゲン原子；ニトロ基；－ＣＯ２ －；－Ｓ（Ｏ）２Ｏ－等が好ましい。
　Ｒ６としては、－ＣＯ－ＯＲｎａ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎａ１）、－ＣＯ－Ｎ（Ｒｎａ１）２又は－ＣＯ－Ｒｎａ１が好ましい。
　Ｒ２１及びＲ２２が、各々が結合する炭素原子と一緒になって環を形成しない場合、Ｒ２１としては、－ＣＯ－ＯＲｎａ２、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎａ２）、－ＣＯ－Ｎ（Ｒｎａ２）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎａ２又は－Ｓ（Ｏ）２－Ｒｎａ２が好ましく、－ＣＯ－ＯＲｎａ２、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎａ２）、－ＣＯ－Ｎ（Ｒｎａ２）２又は－ＣＯ－Ｒｎａ２がより好ましく、Ｒ２２としては、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、ニトロ基、－ＣＯ２ －又は－Ｓ（Ｏ）２Ｏ－が好ましく、シアノ基がより好ましい。この場合、Ｒ６とＲ２１とは、同一の基であることが好ましい。
　Ｒｎａ２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－ＮＲｎａ１０－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。Ｒｎａ２の具体例及び好ましい例は、Ｒｎａ１と同様である。Ｒｎａ２が複数個存在する場合、これらは同一であってもよく、異なっていてもよい。
　Ｒ２１及びＲ２２が、各々が結合する炭素原子と一緒になって環を形成する場合、群Ｂの構造を形成することが好ましく、式（２ａ－ｘ）で表される環を形成することがより好ましい。式（２ａ－ｘ）において、Ｒ２３及びＲ２４としては、水素原子が好ましい。
　Ｒ２１及びＲ２２は、環を形成しないことも好ましい。
　Ｒｎａ１、Ｒｎａ２としては、メチル基、エチル基、ブチル基等の炭素数１～１０のアルキル基；フェニル基、トルイル基、エチルフェニル基等の炭素数６～１０の芳香族炭化水素基；ベンジル基（フェニルメチル基ともいう）、２－メチルベンジル基、３－メチルベンジル基、４－メチルベンジル基、フェニルエチル基、フェニルプロピル基等の鎖状炭化水素基と芳香族炭化水素基を組み合わせた基であって炭素数７～１５の基；等が好ましく、これらの基は、－ＣＯ２ －又は－Ｓ（Ｏ）２Ｏ－を有していてもよく、置換基として、メトキシ基等の炭素数１～１０のアルコキシ基；メトキシカルボニル基等の炭素数１～１０の炭化水素基が結合したオキシカルボニル基；スルファモイル基；ヒドロキシ基；塩素原子等のハロゲン原子；を有していてもよく、－ＣＯ２ －、－Ｓ（Ｏ）２Ｏ－を有することが好ましい。
　Ｍｂ＋としては、ヒドロン、Ｍｇ２＋、Ｃａ２＋、Ｓｒ２＋、Ｂａ２＋、Ｚｎ２＋、Ｃｕ２＋、Ｆｅ２＋、Ｍｎ２＋、Ａｌ３＋、Ｆｅ３＋、Ｃｒ３＋及びＭｎ４＋からなる群より選ばれる一種が好ましく、ヒドロンがより好ましい。
　ａとしては、１～１０のいずれかの整数が好ましく、１～５のいずれかの整数がより好ましい。ａが０であることも好ましい。 In the first embodiment of the compound (B) represented by the formula (I), R 1 to R 6 , R 21 , R 22 , R na1 , R na2 , M b + and a are preferably as follows: .
R 1 is preferably a hydrogen atom.
R 2 to R 5 are each 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; a hydrogen atom contained in an alkyl group such as a trifluoromethyl group A group in which all of the above are replaced by a fluorine atom; a halogen atom such as a chlorine atom or a bromine atom; a nitro group; —CO 2 — ; —S (O) 2 O — or the like.
R 6 is preferably —CO—OR na1 , —CO—NH 2 , —CO—NH (R na1 ), —CO—N (R na1 ) 2 or —CO—R na1 .
When R 21 and R 22 do not form a ring together with the carbon atom to which each is bonded, R 21 includes —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 are preferred, —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 is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or a substituent. An optionally substituted heterocyclic group, a hydrogen atom, a halogen atom, a cyano group, a nitro group, —CO 2 — or —S (O) 2 O — is preferable, and a cyano group is more preferable. In this case, R 6 and R 21 are preferably the same group.
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 —CH 2 — contained in the hydrocarbon group and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR NA 10 - be replaced in Good. However, —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —. Specific examples and preferred examples of R na2 are the same as R na1. When two or more Rna2 exists, these may be the same and may differ.
When R 21 and R 22 together with the carbon atom to which each is bonded form a ring, it is preferable to form the structure of group B, and to form the ring represented by formula (2a-x) Is more preferable. In the formula (2a-x), R 23 and R 24 are preferably hydrogen atoms.
It is also preferred that R 21 and R 22 do not form a ring.
R na1 and R na2 are alkyl groups having 1 to 10 carbon atoms such as methyl group, ethyl group and butyl group; aromatic hydrocarbon groups having 6 to 10 carbon atoms such as phenyl group, toluyl group and ethylphenyl group; Combination of chain hydrocarbon group such as benzyl group (also called phenylmethyl group), 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, phenylethyl group, phenylpropyl group and aromatic hydrocarbon group These groups are preferably a group having 7 to 15 carbon atoms; these groups may have —CO 2 — or —S (O) 2 O — , and a substituent such as a methoxy group An alkoxy group having 1 to 10 carbon atoms such as a methoxycarbonyl group; a sulfamoyl group; a hydroxy group; a halogen atom such as a chlorine atom May have, -CO 2 -, -S (O ) 2 O - preferably has.
M b + is a kind selected from the group consisting of hydrone, Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Zn 2+ , Cu 2+ , Fe 2+ , Mn 2+ , Al 3+ , Fe 3+ , Cr 3+ and Mn 4+. Preferably, hydrone is more preferable.
a is preferably an integer of 1 to 10, more preferably an integer of 1 to 5. It is also preferable that a is 0.
　式（Ｉ）で表される化合物（Ｂ）の第２態様に係る式（ＩＩＢ）で表される化合物において、Ｒ１１ｂ～Ｒ１６ｂ、Ｒ２１ｂ～Ｒ２４ｂ、Ｒｎｂ１、Ｒｎｂ５は、以下のとおりであることが好ましい。
　Ｒ１１ｂとしては、水素原子が好ましい。
　Ｒ１２ｂ～Ｒ１５ｂとしては、水素原子；ブチル基等の炭素数１～１０のアルキル基；メトキシ基等の炭素数１～１０のアルコキシ基；トリフルオロメチル基等のアルキル基に含まれる水素原子の全てがフッ素原子に置き換わった基；塩素原子、臭素原子等のハロゲン原子；ニトロ基等が好ましい。
　Ｒ１６ｂとしては、－ＣＯ－ＯＲｎｂ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ１）、－ＣＯ－Ｎ（Ｒｎｂ１）２又は－ＣＯ－Ｒｎｂ１が好ましい。
　Ｒ２１ｂ及びＲ２２ｂが、各々が結合する炭素原子と一緒になって環を形成しない場合、Ｒ２１ｂとしては、－ＣＯ－ＯＲｎｂ５、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ５）、－ＣＯ－Ｎ（Ｒｎｂ５）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎｂ５又は－Ｓ（Ｏ）２－Ｒｎｂ５が好ましく、－ＣＯ－ＯＲｎｂ５、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ５）、－ＣＯ－Ｎ（Ｒｎｂ５）２又は－ＣＯ－Ｒｎｂ５がより好ましく、Ｒ２２ｂとしては、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が好ましく、シアノ基がより好ましい。この場合、Ｒ１６ｂとＲ２１ｂとは、同一の基であることが好ましい。
　Ｒｎｂ５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－ＮＲｎｂ１０－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。Ｒｎｂ５の具体例及び好ましい例は、Ｒｎｂ１と同様である。Ｒｎｂ５が複数個存在する場合、これらは同一であってもよく、異なっていてもよい。
　Ｒ２１ｂ及びＲ２２ｂが、各々が結合する炭素原子と一緒になって環を形成する場合、群Ｃの構造を形成することが好ましく、式（２ａ－ｘｂ）で表される環を形成することがより好ましい。式（２ａ－ｘｂ）において、Ｒ２３ｂ及びＲ２４ｂとしては、水素原子が好ましい。
　Ｒ２１ｂ及びＲ２２ｂは、環を形成しないことも好ましい。
　Ｒｎｂ１、Ｒｎｂ５としては、メチル基、エチル基、ブチル基等の炭素数１～１０のアルキル基；フェニル基、トルイル基、エチルフェニル基等の炭素数６～１０の芳香族炭化水素基；フェニルメチル基、２－メチルベンジル基、３－メチルベンジル基、４－メチルベンジル基、フェニルエチル基、フェニルプロピル基等の鎖状炭化水素基と芳香族炭化水素基を組み合わせた基であって炭素数７～１５の基；等が好ましく、これらの基は、置換基として、メトキシ基等の炭素数１～１０のアルコキシ基；メトキシカルボニル基等の炭素数１～１０の炭化水素基が結合したオキシカルボニル基；スルファモイル基；ヒドロキシ基；塩素原子等のハロゲン原子；を有していてもよい。 In the compound represented by the formula (IIB) according to the second embodiment of the compound (B) represented by the formula (I), R 11b to R 16b , R 21b to R 24b , R nb1 , R nb5 are the following: It is preferable that it is as follows.
R 11b is preferably a hydrogen atom.
R 12b to R 15b are each a hydrogen atom; a C 1-10 alkyl group such as a butyl group; a C 1-10 alkoxy group such as a methoxy group; a hydrogen atom contained in an alkyl group such as a trifluoromethyl group Are preferably groups in which all of the above are replaced by fluorine atoms; halogen atoms such as chlorine atoms and bromine atoms; nitro groups and the like.
R 16b is preferably —CO—OR nb1 , —CO—NH 2 , —CO—NH (R nb1 ), —CO—N (R nb1 ) 2 or —CO—R nb1 .
When R 21b and R 22b do not form a ring together with the carbon atom to which each is bonded, R 21b includes -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 are preferred, —CO—OR nb5 , —CO—NH 2 , —CO—NH ( R nb5 ), —CO—N (R nb5 ) 2 or —CO—R nb5 is more preferred, and R 22b represents a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or a substituent. An optionally substituted heterocyclic group, a hydrogen atom, a halogen atom, a cyano group or a nitro group is preferable, and a cyano group is more preferable. In this case, R 16b and R 21b are preferably the same group.
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 —CH 2 — contained in the hydrocarbon group and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR NB 10 - be replaced in Good. However, —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —. Specific examples and preferred examples of R nb5 is the same as R nb1. When two or more Rnb5 exists, these may be the same and may differ.
When R 21b and R 22b together with the carbon atom to which each is bonded form a ring, it is preferable to form the structure of group C and form the ring represented by formula (2a-xb) Is more preferable. In formula (2a-xb), R 23b and R 24b are preferably hydrogen atoms.
It is also preferred that R 21b and R 22b do not form a ring.
R nb1 and R nb5 are alkyl groups having 1 to 10 carbon atoms such as methyl group, ethyl group and butyl group; aromatic hydrocarbon groups having 6 to 10 carbon atoms such as phenyl group, toluyl group and ethylphenyl group; A group comprising a chain hydrocarbon group such as phenylmethyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, phenylethyl group, phenylpropyl group, etc., and an aromatic hydrocarbon group. These groups are preferably substituted with a C 1-10 alkoxy group such as a methoxy group; a C 1-10 hydrocarbon group such as a methoxycarbonyl group as a substituent. An oxycarbonyl group; a sulfamoyl group; a hydroxy group; and a halogen atom such as a chlorine atom.
　式（Ｉ）で表される化合物（Ｂ）の第３態様に係る式（ＩＡ）で表される化合物において、Ｒ１ａ～Ｒ９ａ、Ｒｎａ４、Ｍｂ＋、ａは、以下のとおりであることが好ましい。
　Ｒ１ａとしては、水素原子が好ましい。
　Ｒ２ａ～Ｒ５ａとしては、水素原子；ブチル基等の炭素数１～１０のアルキル基；メトキシ基等の炭素数１～１０のアルコキシ基；トリフルオロメチル基等のアルキル基に含まれる水素原子の全てがフッ素原子に置き換わった基；塩素原子、臭素原子等のハロゲン原子；ニトロ基；－ＣＯ２ －；－Ｓ（Ｏ）２Ｏ－等が好ましい。
　Ｒ６ａとしては、－ＣＯＯ－、－ＣＯ－ＯＲｎａ４、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎａ４）、－ＣＯ－Ｎ（Ｒｎａ４）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎａ４又は－Ｓ（Ｏ）２－Ｒｎａ４が好ましく、－ＣＯ－ＯＲｎａ４、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎａ４）、－ＣＯ－Ｎ（Ｒｎａ４）２又は－ＣＯ－Ｒｎａ４がより好ましい。
　Ｒｎａ４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－ＮＲｎａ１０－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。Ｒｎａ４の具体例及び好ましい例は、Ｒｎａ１と同様である。Ｒｎａ２が複数個存在する場合、これらは同一であってもよく、異なっていてもよい。
　Ｒ７ａとしては、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、ニトロ基、－ＣＯ２ －又は－Ｓ（Ｏ）２Ｏ－が好ましく、シアノ基がより好ましい。
　Ｒ８ａ及びＲ９ａが、各々が結合する炭素原子と一緒になって環を形成しない場合、Ｒ８ａとしては、－ＣＯＯ－、－ＣＯ－ＯＲｎａ４、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎａ４）、－ＣＯ－Ｎ（Ｒｎａ４）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎａ４又は－Ｓ（Ｏ）２－Ｒｎａ４が好ましく、－ＣＯ－ＯＲｎａ４、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎａ４）、－ＣＯ－Ｎ（Ｒｎａ４）２又は－ＣＯ－Ｒｎａ４がより好ましく、Ｒ７ａとしては、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、ニトロ基、－ＣＯ２ －又は－Ｓ（Ｏ）２Ｏ－が好ましく、シアノ基がより好ましい。この場合、Ｒ６ａとＲ８ａとは、同一の基であることが好ましい。
　Ｒ８ａ及びＲ９ａが、各々が結合する炭素原子と一緒になって環を形成する場合、群Ａの構造を形成することが好ましく、式（ＱＱ１８）で表される環を形成することが好ましい。式（ＱＱ１８）において、Ｒ２５及びＲ２６としては、水素原子が好ましい。
　Ｒ８ａ及びＲ９ａは、環を形成しないことも好ましい。
　Ｒｎａ４としては、メチル基、エチル基、ブチル基等の炭素数１～１０のアルキル基；フェニル基、トルイル基、エチルフェニル基等の炭素数６～１０の芳香族炭化水素基；フェニルメチル基、２－メチルベンジル基、３－メチルベンジル基、４－メチルベンジル基、フェニルエチル基、フェニルプロピル基等の鎖状炭化水素基と芳香族炭化水素基を組み合わせた基であって炭素数７～１５の基；等が好ましく、これらの基は、－ＣＯ２ －又は－Ｓ（Ｏ）２Ｏ－を有していてもよく、置換基として、メトキシ基等の炭素数１～１０のアルコキシ基；メトキシカルボニル基等の炭素数１～１０の炭化水素基が結合したオキシカルボニル基；スルファモイル基；ヒドロキシ基；塩素原子等のハロゲン原子；を有していてもよく、－ＣＯ２ －、－Ｓ（Ｏ）２Ｏ－を有することが好ましい。
　Ｍｂ＋としては、ヒドロン、Ｍｇ２＋、Ｃａ２＋、Ｓｒ２＋、Ｂａ２＋、Ｚｎ２＋、Ｃｕ２＋、Ｆｅ２＋、Ｍｎ２＋、Ａｌ３＋、Ｆｅ３＋、Ｃｒ３＋及びＭｎ４＋からなる群より選ばれる一種が好ましく、ヒドロンがより好ましい。
　ａとしては、１～５のいずれかの整数が好ましい。 In the compound represented by the formula (IA) according to the third embodiment of the compound (B) represented by the formula (I), R 1a to R 9a , R na4 , M b + and a are as follows: Is preferred.
R 1a is preferably a hydrogen atom.
R 2a to R 5a are each 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; a hydrogen atom contained in an alkyl group such as a trifluoromethyl group group all is replaced with a fluorine atom; a chlorine atom, a halogen atom such as a bromine atom; a nitro group; -CO 2 -; -S (O ) 2 O - , and the like are preferable.
R 6a includes —COO − , —CO—OR na 4 , —CO—NH 2 , —CO—NH (R na4 ), —CO—N (R na4 ) 2 , —CO—H, —CO—R na 4 Or —S (O) 2 —R na4 is preferred, —CO—OR na4 , —CO—NH 2 , —CO—NH (R na4 ), —CO—N (R na4 ) 2 or —CO—R na4 is More preferred.
R na4 represents an optionally substituted hydrocarbon group having 1 to 35 carbon atoms or an optionally substituted heterocyclic group, and —CH 2 — contained in the hydrocarbon group. and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR NA 10 - be replaced in Good. However, —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —. Specific examples and preferred examples of R na4 is the same as R na1. When two or more Rna2 exists, these may be the same and may differ.
As R 7a, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, an optionally substituted heterocyclic group, a hydrogen atom, a halogen atom, a cyano group, a nitro group, — CO 2 — or —S (O) 2 O — is preferable, and a cyano group is more preferable.
When R 8a and R 9a do not form a ring with the carbon atom to which each is bonded, R 8a includes —COO − , —CO—OR na4 , —CO—NH 2 , —CO—NH ( R na4 ), —CO—N (R na4 ) 2 , —CO—H, —CO—R na4 or —S (O) 2 —R na4 are preferred, —CO—OR na4 , —CO—NH 2 , — CO—NH (R na4 ), —CO—N (R na4 ) 2 or —CO—R na4 is more preferable, and R 7a is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent. An optionally substituted heterocyclic group, a hydrogen atom, a halogen atom, a cyano group, a nitro group, —CO 2 — or —S (O) 2 O — is preferable, and a cyano group is more preferable. In this case, R 6a and R 8a are preferably the same group.
When R 8a and R 9a together with the carbon atom to which each is bonded form a ring, it is preferable to form a structure of group A, and it is preferable to form a ring represented by the formula (QQ18) . In formula (QQ18), R 25 and R 26 are preferably a hydrogen atom.
It is also preferred that R 8a and R 9a do not form a ring.
R na4 includes 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 phenylmethyl group A group comprising a combination of a chain hydrocarbon group such as 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, phenylethyl group, phenylpropyl group and an aromatic hydrocarbon group, having 7 to 7 carbon atoms And the like. These groups may have —CO 2 — or —S (O) 2 O — , and the substituent may be an alkoxy group having 1 to 10 carbon atoms such as a methoxy group. a halogen atom such as a chlorine atom; a sulfamoyl group; hydroxy group oxycarbonyl group having a hydrocarbon group bonded having 1 to 10 carbon atoms such as a methoxycarbonyl group may have, -CO 2 - -S (O) 2 O - preferably it has.
M b + is a kind selected from the group consisting of hydrone, Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Zn 2+ , Cu 2+ , Fe 2+ , Mn 2+ , Al 3+ , Fe 3+ , Cr 3+ and Mn 4+. Preferably, hydrone is more preferable.
a is preferably an integer of 1 to 5.
　式（Ｉ）で表される化合物（Ｂ）の第４態様に係る式（ＩＢ）で表される化合物において、Ｒ１ｂ～Ｒ７ｂ、Ｒ１７ｂ～Ｒ１８ｂ、Ｒｎｂ１、Ｒｎｂ６は、以下のとおりであることが好ましい。
　Ｒ１ｂとしては、水素原子が好ましい。
　Ｒ２ｂ～Ｒ５ｂとしては、水素原子；ブチル基等の炭素数１～１０のアルキル基；メトキシ基等の炭素数１～１０のアルコキシ基；トリフルオロメチル基等のアルキル基に含まれる水素原子の全てがフッ素原子に置き換わった基；塩素原子、臭素原子等のハロゲン原子；ニトロ基等が好ましい。
　Ｒ６ｂとしては、－ＣＯ－ＯＲｎｂ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ１）、－ＣＯ－Ｎ（Ｒｎｂ１）２又は－ＣＯ－Ｒｎｂ１が好ましい。
　Ｒ７ｂとしては、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、ニトロ基、－ＣＯ２ －又は－Ｓ（Ｏ）２Ｏ－が好ましく、シアノ基がより好ましい。
　Ｒ１７ｂ及びＲ１８ｂが、各々が結合する炭素原子と一緒になって環を形成しない場合、Ｒ１７ｂとしては、－ＣＯ－ＯＲｎｂ６、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ６）、－ＣＯ－Ｎ（Ｒｎｂ６）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎｂ６又は－Ｓ（Ｏ）２－Ｒｎｂ６が好ましく、－ＣＯ－ＯＲｎｂ６、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ６）、－ＣＯ－Ｎ（Ｒｎｂ６）２又は－ＣＯ－Ｒｎｂ６がより好ましく、Ｒ１８ｂとしては、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が好ましく、シアノ基がより好ましい。この場合、Ｒ６ｂとＲ１７ｂとは、同一の基であることが好ましい。
　Ｒｎｂ６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－ＮＲｎｂ１０－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。Ｒｎｂ６の具体例及び好ましい例は、Ｒｎｂ１と同様である。Ｒｎｂ６が複数個存在する場合、これらは同一であってもよく、異なっていてもよい。
　Ｒ１７ｂ及びＲ１８ｂが、各々が結合する炭素原子と一緒になって環を形成する場合、群Ｃの構造を形成するものが好ましく、式（２ａ）で表される環を形成することがより好ましい。式（２ａ）において、Ｒ１９ｂ及びＲ２０ｂとしては、水素原子が好ましい。
　Ｒ１７ｂ及びＲ１８ｂは、環を形成しないことも好ましい。
　Ｒｎｂ１、Ｒｎｂ６としては、メチル基、エチル基、ブチル基等の炭素数１～１０のアルキル基；フェニル基、トルイル基、エチルフェニル基等の炭素数６～１０の芳香族炭化水素基；フェニルメチル基、２－メチルベンジル基、３－メチルベンジル基、４－メチルベンジル基、フェニルエチル基、フェニルプロピル基等の鎖状炭化水素基と芳香族炭化水素基を組み合わせた基であって炭素数７～１５の基；等が好ましく、これらの基は、置換基として、メトキシ基等の炭素数１～１０のアルコキシ基；メトキシカルボニル基等の炭素数１～１０の炭化水素基が結合したオキシカルボニル基；スルファモイル基；ヒドロキシ基；塩素原子等のハロゲン原子；を有していてもよい。 In the compound represented by the formula (IB) according to the fourth embodiment of the compound (B) represented by the formula (I), R 1b to R 7b , R 17b to R 18b , R nb1 , R nb6 are the following: It is preferable that it is as follows.
R 1b is preferably a hydrogen atom.
R 2b to R 5b are each a hydrogen atom; a C 1-10 alkyl group such as a butyl group; a C 1-10 alkoxy group such as a methoxy group; a hydrogen atom contained in an alkyl group such as a trifluoromethyl group Are preferably groups in which all of the above are replaced by fluorine atoms; halogen atoms such as chlorine atoms and bromine atoms; nitro groups and the like.
R 6b is preferably —CO—OR nb1 , —CO—NH 2 , —CO—NH (R nb1 ), —CO—N (R nb1 ) 2 or —CO—R nb1 .
R 7b includes 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) 2 O — is preferable, and a cyano group is more preferable.
When R 17b and R 18b do not form a ring together with the carbon atom to which each is bonded, R 17b includes —CO—OR nb6 , —CO—NH 2 , —CO—NH (R nb6 ), —CO—N (R nb6 ) 2 , —CO—H, —CO—R nb6 or —S (O) 2 —R nb6 are preferred, —CO—OR nb6 , —CO—NH 2 , —CO—NH ( R nb6 ), —CO—N (R nb6 ) 2 or —CO—R nb6 is more preferred, and R 18b is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a substituent. An optionally substituted heterocyclic group, a hydrogen atom, a halogen atom, a cyano group or a nitro group is preferable, and a cyano group is more preferable. In this case, R 6b and R 17b are preferably the same group.
R nb6 represents an optionally substituted hydrocarbon group having 1 to 35 carbon atoms or an optionally substituted heterocyclic group, and —CH 2 — contained in the hydrocarbon group. and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR NB 10 - be replaced in Good. However, —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —. Specific examples and preferred examples of R nb6 is the same as R nb1. When two or more Rnb6 exists, these may be the same and may differ.
When R 17b and R 18b together with the carbon atom to which each is bonded form a ring, those that form the structure of group C are preferred, and more preferably form the ring represented by formula (2a) preferable. In the formula (2a), R 19b and R 20b are preferably hydrogen atoms.
It is also preferred that R 17b and R 18b do not form a ring.
R nb1 and R nb6 are alkyl groups having 1 to 10 carbon atoms such as methyl group, ethyl group and butyl group; aromatic hydrocarbon groups having 6 to 10 carbon atoms such as phenyl group, toluyl group and ethylphenyl group; A group comprising a chain hydrocarbon group such as phenylmethyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, phenylethyl group, phenylpropyl group, etc., and an aromatic hydrocarbon group. These groups are preferably substituted with a C 1-10 alkoxy group such as a methoxy group; a C 1-10 hydrocarbon group such as a methoxycarbonyl group as a substituent. An oxycarbonyl group; a sulfamoyl group; a hydroxy group; and a halogen atom such as a chlorine atom.
　－ＣＯ－ＯＲｎａ１、－ＣＯ－ＯＲｎａ２、－ＣＯ－ＯＲｎｂ１、－ＣＯ－ＯＲｎｂ５、－ＣＯ－ＯＲｎａ４、－ＣＯ－ＯＲｎｂ６としては、メトキシカルボニル基、エトキシカルボニル基等のアルキル基の炭素数が１～１０の炭化水素基（特にアルキル基）が結合したオキシカルボニル基が好ましい。 -CO-OR na1 , -CO-OR na2 , -CO-OR nb1 , -CO-OR nb5 , -CO-OR na4 , -CO-OR nb6 are alkyl groups such as methoxycarbonyl group and ethoxycarbonyl group. An oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms (particularly an alkyl group) is bonded is preferred.
　－ＣＯ－Ｒｎａ１、－ＣＯ－Ｒｎａ２、－ＣＯ－Ｒｎｂ１、－ＣＯ－Ｒｎｂ５、－ＣＯ－Ｒｎａ４、－ＣＯ－Ｒｎｂ６としては、ベンゾイル基等の炭素数６～１０の芳香族環が結合したカルボニル基；エチルカルボニル基、ブチルカルボニル基等の炭素数１～１０のアルキル基が結合したカルボニル基；フェニルメチル基、フェニルエチル基、フェニルプロピル基等の炭素数１～１０の芳香族環が結合した炭素数１～１０のアルキル基が結合したカルボニル基が好ましい。
　－ＣＯ－Ｒｎａ１、－ＣＯ－Ｒｎａ２、－ＣＯ－Ｒｎａ４、のＲｎａ１、Ｒｎａ２、Ｒｎａ４は、－ＣＯ２ －又は－Ｓ（Ｏ）２Ｏ－を有していてもよく、置換基として、メトキシ基等の炭素数１～１０のアルコキシ基；メトキシカルボニル基等の炭素数１～１０の炭化水素基が結合したオキシカルボニル基；スルファモイル基；ヒドロキシ基；塩素原子等のハロゲン原子；を有していてもよく、該芳香族環が結合したカルボニル基；アルキル基が結合したカルボニル基；芳香族環が結合したアルキル基が結合したカルボニル基等の炭素原子には、－ＣＯ２ －；－Ｓ（Ｏ）２Ｏ－；メトキシ基等の炭素数１～１０のアルコキシ基；メトキシカルボニル基等の炭素数１～１０の炭化水素基が結合したオキシカルボニル基；スルファモイル基；ヒドロキシ基；塩素原子等のハロゲン原子；等が結合していてもよい。 —CO—R na1 , —CO—R na2 , —CO—R nb1 , —CO—R nb5 , —CO—R na4 , —CO—R nb6 are aromatics having 6 to 10 carbon atoms such as a benzoyl group. A carbonyl group to which a ring is bonded; a carbonyl group to which an alkyl group having 1 to 10 carbon atoms such as ethylcarbonyl group and butylcarbonyl group is bonded; an aromatic having 1 to 10 carbon atoms such as phenylmethyl group, phenylethyl group and phenylpropyl group A carbonyl group to which an alkyl group having 1 to 10 carbon atoms to which an aromatic ring is bonded is bonded is preferred.
-CO-R na1, -CO-R na2, -CO-R na4, the R na1, R na2, R na4 is, -CO 2 - or -S (O) 2 O - may have, As a substituent, an alkoxy group having 1 to 10 carbon atoms such as a methoxy group; an oxycarbonyl group bonded with a hydrocarbon group having 1 to 10 carbon atoms such as a methoxycarbonyl group; a sulfamoyl group; a hydroxy group; a halogen atom such as a chlorine atom A carbon atom such as a carbonyl group to which the aromatic ring is bonded; a carbonyl group to which an alkyl group is bonded; a carbonyl group to which an alkyl group to which an aromatic ring is bonded is bonded to —CO 2 -; -S (O) 2 O -; oxycarbonyl group is a hydrocarbon group having 1 to 10 carbon atoms such as methoxycarbonyl group attached; alkoxy group having 1 to 10 carbon atoms such as a methoxy group Sulf Sulfamoyl group; a halogen atom such as a chlorine atom; hydroxy group may be bonded.
　－ＣＯ－ＮＨ（Ｒｎａ１）、－ＣＯ－ＮＨ（Ｒｎａ２）、－ＣＯ－ＮＨ（Ｒｎｂ１）、－ＣＯ－ＮＨ（Ｒｎｂ５）、－ＣＯ－ＮＨ（Ｒｎａ４）、－ＣＯ－ＮＨ（Ｒｎｂ６）としては、メチルアミノカルボニル基等の炭素数１～１０のアルキル基が結合したアミノカルボニル基が好ましい。また、該アルキル基が結合したアミノカルボニル基、芳香族炭化水素環が結合したアミノカルボニル基等の炭素原子には、－ＣＯ２ －が結合していてもよい。 -CO-NH (R na1), - CO-NH (R na2), - CO-NH (R nb1), - CO-NH (R nb5), - CO-NH (R na4), - CO-NH ( R nb6 ) is preferably an aminocarbonyl group to which an alkyl group having 1 to 10 carbon atoms such as a methylaminocarbonyl group is bonded. In addition, —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（Ｒｎａ１）２、－ＣＯ－Ｎ（Ｒｎａ２）２、－ＣＯ－Ｎ（Ｒｎｂ１）２、－ＣＯ－Ｎ（Ｒｎｂ５）２、－ＣＯ－Ｎ（Ｒｎａ４）２、－ＣＯ－Ｎ（Ｒｎｂ６）２としては、ジメチルアミノカルボニル基等の炭素数１～１０のアルキル基が２つ結合したアミノカルボニル基が好ましい。 -CO-N (R na1 ) 2 , -CO-N (R na2 ) 2 , -CO-N (R nb1 ) 2 , -CO-N (R nb5 ) 2 , -CO-N (R na4 ) 2 , —CO—N (R nb6 ) 2 is preferably an aminocarbonyl group in which two alkyl groups having 1 to 10 carbon atoms such as a dimethylaminocarbonyl group are bonded.
　〔２－６〕式（Ｉ）で表される化合物（Ｂ）の具体例
　式（Ｉ）で表される化合物（Ｂ）の好ましい態様の一つは、上記〔２－３〕で述べた第３態様である。第３態様において、好ましくは、式（ＩＡ）におけるａａは２であり、Ｒ１ａは水素原子であり、Ｒ６ａ及びＲ７ａの一方がシアノ基であり、Ｒ８ａ及びＲ９ａの一方がシアノ基であり、Ｍｂ＋はヒドロンであり、ｂは１であり、ｍａは２であり、ｎａは１である。
　式（Ｉ）で表される化合物（Ｂ）のより好ましい一例は、式（Ｐ）で表される化合物である。 [2-6] Specific Example of Compound (B) Represented by Formula (I) One preferred embodiment of the compound (B) represented by formula (I) is the compound described in [2-3] above. There are three modes. In the third aspect, preferably, aa in formula (IA) is 2, R 1a is a hydrogen atom, one of R 6a and R 7a is a cyano group, and one of R 8a and R 9a is a cyano group M b + is hydrone, b is 1, ma is 2, and na is 1.
A more preferable example of the compound (B) represented by the formula (I) is a compound represented by the formula (P).
Figure JPOXMLDOC01-appb-I000026
Figure JPOXMLDOC01-appb-I000026
［式（Ｐ）中、Ｌ４及びＬ５は、互いに独立に、炭素数１～１０の２価の炭化水素基を表し、該炭化水素基が－ＣＨ２－を含む場合、該－ＣＨ２－は、－ＮＨ－に置き換わっていてもよい。Ｒｐは、水素原子又は置換基を表し、ｐは１～４のいずれかの整数を表す。波線は、Ｅ体、Ｚ体、又はこれらの双方を表す。］
　上記２価の炭化水素基としては、例えば、アルキレン基、アリーレン基（例えばフェニレン基）が挙げられる。 Wherein (P), L 4 and L 5, independently of one another, represents a divalent hydrocarbon group having 1 to 10 carbon atoms, the hydrocarbon group is -CH 2 - if it contains, the -CH 2 -May be replaced by -NH-. R p represents a hydrogen atom or a substituent, and p represents any integer of 1 to 4. The wavy line represents the E body, the Z body, or both. ]
Examples of the divalent hydrocarbon group include an alkylene group and an arylene group (for example, a phenylene group).
　式（Ｉ）で表される化合物（Ｂ）のより好ましい他の一例は、式（Ｐ）において、２つのＣＯＯＨ基が－Ｓ（Ｏ）２ＯＨ基に置き換わった化合物である。 Another more preferable example of the compound (B) represented by the formula (I) is a compound in which two COOH groups are replaced by —S (O) 2 OH groups in the formula (P).
　式（Ｉ）、式（ＩＡ）、式（ＩＢ）又は式（ＩＩＢ）で表される化合物の具体例としては、例えば、
　下記式（Ｉａ）で表される化合物において、Ｒ３１、Ｌ１、Ｌ２、Ｒ３２、Ｂ１Ｂ２、ｎ、ｍ及びＭｂ＋の組み合わせが表１～表４に記載のいずれかである化合物、並びに、
　下記式（Ｉｂ）で表される化合物において、Ｒ３３、Ｌ３、Ｂ１Ｂ２、ｎ、ｍ及びＭｂ＋の組み合わせが表５～表６に記載のいずれかである化合物
が挙げられる。
　なお、Ｒ３１、Ｒ３２、Ｒ３３は、式（ＨＨ１）～式（ＨＨ１８）で表されるいずれかの部分構造を表す。Ｂ１Ｂ２は、式（ＢＢ１）～式（ＢＢ９）で表されるいずれかの部分構造を表す。 Specific examples of the compound represented by formula (I), formula (IA), formula (IB) or formula (IIB) include, for example,
In the compound represented by the following formula (Ia), a combination of R 31 , L 1 , L 2 , R 32 , B 1 B 2 , n, m and M b + is any of Tables 1 to 4 A compound, and
Examples of the compound represented by the following formula (Ib) include compounds in which the combination of R 33 , L 3 , B 1 B 2 , n, m and M b + is any one of those shown in Tables 5 to 6.
Note that R 31 , R 32 , and R 33 each represent a partial structure represented by the formula (HH1) to the formula (HH18). B 1 B 2 represents any one of the partial structures represented by the formulas (BB1) to (BB9).
Figure JPOXMLDOC01-appb-I000027
［式中、波線は、Ｅ体、Ｚ体、又はこれらの双方を表す。］
Figure JPOXMLDOC01-appb-I000027
[Wherein the wavy line represents E-form, Z-form, or both. ]
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-I000034
Figure JPOXMLDOC01-appb-I000034
Figure JPOXMLDOC01-appb-I000035
Figure JPOXMLDOC01-appb-I000035
　表に示した化合物のうち、化合物番号２８～３１、３７～４０、４６～４９、５５～５８、７３～７６、８２～８５、９１～９４、１３６～１３９、１５４～１５７、１９０～１９３、１９９～２０２、２０８～２１１、２４４～２４７、２９８～３０１の化合物が好ましい。 Of the compounds shown in the table, compound numbers 28-31, 37-40, 46-49, 55-58, 73-76, 82-85, 91-94, 136-139, 154-157, 190-193, Compounds of 199 to 202, 208 to 211, 244 to 247, and 298 to 301 are preferred.
　〔２－７〕式（Ｉ）で表される化合物（Ｂ）の製造方法
　式（Ｉ）で表される化合物（Ｂ）は、Ｒ１が水素原子のとき、式（ｐｔ１）で表される化合物（以下、フタロニトリル化合物ということがある。）を式（ｐｔ２）で表される化合物（以下、アルコキシド化合物ということがある。）と反応させた後、式（ｐｔ３）で表される化合物（以下、化合物（ｐｔ３）ということがある。）と式（ｐｔ４）で表される化合物（以下、化合物（ｐｔ４）ということがある。）とをさらに酸の存在下で反応させることで製造できる。 [2-7] Method for producing compound (B) represented by formula (I) Compound (B) represented by formula (I) is represented by formula (pt1) when R 1 is a hydrogen atom. After reacting a compound (hereinafter sometimes referred to as a phthalonitrile compound) with a compound represented by formula (pt2) (hereinafter sometimes referred to as an alkoxide compound), a compound represented by formula (pt3) ( Hereinafter, the compound (sometimes referred to as “pt3”) and the compound represented by the formula (pt4) (hereinafter sometimes referred to as “compound (pt4)”) can be further reacted in the presence of an acid.
Figure JPOXMLDOC01-appb-I000036
Figure JPOXMLDOC01-appb-I000036
［式（ｐｔ１）～式（ｐｔ８）及び式（１）中、
　Ｒ１～Ｒ７、Ｘ、Ｍｂ＋、ａ、ｍ、及びｎは、前記と同じ意味を表す。
　Ｒ４１及びＲ４２は、互いに独立に、水素原子又は炭素数１～２０のアルキル基を表す。
　Ｍ１及びＭ２は、アルカリ金属原子を表す。
　ＬＧ１及びＬＧ２は、互いに独立に、ハロゲン原子、メタンスルホニルオキシ基、クロロメチルスルホニルオキシ基、トルエンスルホニルオキシ基又はトリフルオロメタンスルホニルオキシ基を表す。
　Ｍは、金属原子を表す。］ [In Formula (pt1) to Formula (pt8) and Formula (1),
R 1 to R 7 , X, M b + , a, m, and n represent the same meaning as described above.
R 41 and R 42 each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
M 1 and M 2 represent an alkali metal atom.
LG 1 and LG 2 each independently represent a halogen atom, a methanesulfonyloxy group, a chloromethylsulfonyloxy group, a toluenesulfonyloxy group, or a trifluoromethanesulfonyloxy group.
M represents a metal atom. ]
　Ｒ４１、Ｒ４２で表される炭素数１～２０のアルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基及びｔｅｒｔ－ブチル基等が挙げられ、好ましくは炭素数１～６のアルキル基が挙げられる。
　Ｍ１、Ｍ２で表されるアルカリ金属原子としては、リチウム原子、ナトリウム原子及びカリウム原子が挙げられる。 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. 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.
　式（ｐｔ２）で表されるアルコキシド化合物の使用量は、式（ｐｔ１）で表されるフタロニトリル化合物１モルに対して、通常、０．１モル以上１０モル以下であり、好ましくは０．２モル以上５モル以下であり、より好ましくは０．３モル以上３モル以下であり、さらに好ましくは０．４モル以上２モル以下である。 The amount of the alkoxide compound represented by the formula (pt2) is usually 0.1 mol or more and 10 mol or less, preferably 0.2 mol, relative to 1 mol of the phthalonitrile compound represented by the formula (pt1). The number of moles is 5 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles.
　化合物（ｐｔ３）及び化合物（ｐｔ４）の使用量の合計は、式（ｐｔ１）で表されるフタロニトリル化合物１モルに対して、通常、２モル以上２０モル以下であり、好ましくは２モル以上１０モル以下であり、より好ましくは２モル以上６モル以下であり、さらに好ましくは２モル以上４モル以下である。なお化合物（ｐｔ３）と化合物（ｐｔ４）は、同じ化合物であってもよい。 The total amount of compound (pt3) and compound (pt4) used is usually 2 mol or more and 20 mol or less, preferably 2 mol or more and 10 mol, per 1 mol of the phthalonitrile compound represented by formula (pt1). The amount is 2 mol or less, more preferably 2 mol or more and 6 mol or less, and further preferably 2 mol or more and 4 mol or less. The compound (pt3) and the compound (pt4) may be the same compound.
　酸としては、塩酸、臭化水素酸、ヨウ化水素酸、硫酸、硝酸、フルオロスルホン酸、リン酸等の無機酸；メタンスルホン酸、トリフルオロメタンスルホン酸及びｐ－トルエンスルホン酸等のスルホン酸；酢酸、クエン酸、ギ酸、グルコン酸、乳酸、シュウ酸及び酒石酸等のカルボン酸が挙げられ、好ましくは、塩酸、臭化水素酸、硫酸、メタンスルホン酸、トリフルオロメタンスルホン酸、ｐ－トルエンスルホン酸及びカルボン酸が挙げられ、より好ましくは酢酸が挙げられる。
　酸の使用量は、フタロニトリル化合物１モルに対して、通常１モル以上２０モル以下であり、好ましくは１モル以上１０モル以下であり、より好ましくは１モル以上８モル以下であり、さらに好ましくは１モル以上６モル以下である。 Examples of acids include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; Examples thereof include carboxylic acids such as acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid and tartaric acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid And carboxylic acid, more preferably acetic acid.
The amount of the acid used is usually 1 mol or more and 20 mol or less, preferably 1 mol or more and 10 mol or less, more preferably 1 mol or more and 8 mol or less, more preferably 1 mol per mol of the phthalonitrile compound. Is 1 mol or more and 6 mol or less.
　フタロニトリル化合物、アルコキシド化合物、化合物（ｐｔ３）及び化合物（ｐｔ４）の反応は、通常、溶媒の存在下に実施される。
　溶媒としては、水；アセトニトリル等のニトリル溶媒；メタノール、エタノール、２－プロパノール、１－ブタノール、１－ペンタノール及び１－オクタノール等のアルコール溶媒；テトラヒドロフラン等のエーテル溶媒；アセトン等のケトン溶媒；酢酸エチル等のエステル溶媒；ヘキサン等の脂肪族炭化水素溶媒；トルエン等の芳香族炭化水素溶媒；塩化メチレン及びクロロホルム等のハロゲン化炭化水素溶媒；Ｎ，Ｎ－ジメチルホルムアルデヒド及びＮ－メチルピロリドン等のアミド溶媒；ジメチルスルホキシド等のスルホキシド溶媒が挙げられ、好ましくは、水、ニトリル溶媒、アルコール溶媒、エーテル溶媒、ケトン溶媒、エステル溶媒、芳香族炭化水素溶媒、ハロゲン化炭化水素溶媒、アミド溶媒及びスルホキシド溶媒が挙げられ、より好ましくは、水、アセトニトリル、メタノール、エタノール、２－プロパノール、１－ブタノール、１－ペンタノール、１－オクタノール、テトラヒドロフラン、アセトン、酢酸エチル、トルエン、塩化メチレン、クロロホルム、Ｎ，Ｎ－ジメチルホルムアルデヒド、Ｎ－ジメチルアセトアルデヒド、Ｎ－メチルピロリドン、１，３－ジメチル－２－イミダゾリジノン及び１，３－ジメチル－３，４，５，６－テトラヒドロ－２（１Ｈ）－ピリミジノン及びジメチルスルホキシドが挙げられ、さらに好ましくは、水、アセトニトリル、メタノール、エタノール、２－プロパノール、１－ブタノール、１－ペンタノール、１－オクタノール、アセトン、塩化メチレン、クロロホルム、Ｎ，Ｎ－ジメチルホルムアルデヒド、Ｎ－ジメチルアセトアルデヒド、１，３－ジメチル－２－イミダゾリジノン及び１，３－ジメチル－３，４，５，６－テトラヒドロ－２（１Ｈ）－ピリミジノンＮ－メチルピロリドン及びジメチルスルホキシドが挙げられ、とりわけ好ましくは、水、アセトニトリル、メタノール、エタノール、２－プロパノール、Ｎ－メチルピロリドン及びジメチルスルホキシドが挙げられる。
　溶媒の使用量は、フタロニトリル化合物１質量部に対して、通常１質量部以上１０００質量部以下である。 The reaction of the phthalonitrile compound, alkoxide compound, compound (pt3) and compound (pt4) is usually carried out in the presence of a solvent.
Solvents include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; 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 Solvent; sulfoxide solvents such as dimethyl sulfoxide are mentioned, preferably water, nitrile solvent, alcohol solvent, ether solvent, ketone solvent, ester solvent, aromatic hydrocarbon solvent, halogenated hydrocarbon solvent, amide solvent and sulfoxide solvent. Cited 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 dimethyl sulfoxide More preferably, water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, methylene chloride, chloroform, N, N-dimethylformaldehyde, N-dimethyla Examples include toaldehyde, 1,3-dimethyl-2-imidazolidinone and 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone N-methylpyrrolidone and dimethyl sulfoxide, particularly preferred Includes water, acetonitrile, methanol, ethanol, 2-propanol, N-methylpyrrolidone and dimethyl sulfoxide.
The usage-amount of a solvent is 1 mass part or more and 1000 mass parts or less normally with respect to 1 mass part of phthalonitrile compounds.
　フタロニトリル化合物、アルコキシド化合物、化合物（ｐｔ３）及び化合物（ｐｔ４）の反応温度は、通常０℃以上２００℃以下であり、好ましくは０℃以上１００℃以下であり、より好ましくは０℃以上５０℃以下である。反応時間は、通常０．５時間以上３００時間以下である。 The reaction temperature of the phthalonitrile compound, alkoxide compound, compound (pt3) and compound (pt4) is usually 0 ° C. or higher and 200 ° C. or lower, preferably 0 ° C. or higher and 100 ° C. or lower, more preferably 0 ° C. or higher and 50 ° C. or lower. It is as follows. The reaction time is usually 0.5 hours or more and 300 hours or less.
　さらに化合物（ｐｔ６）を反応させることにより、Ｒ１が水素原子でない式（Ｉ）で表される化合物（Ｂ）を得ることができる。化合物（ｐｔ６）の使用量は、Ｒ１が水素原子である式（Ｉ）で表される化合物（Ｂ）１モルに対し、通常、１モル以上１０モル以下であり、好ましくは１モル以上５モル以下であり、より好ましくは１モル以上３モル以下であり、さらに好ましくは１モル以上２モル以下である。 Further, by reacting the compound (pt6), the compound (B) represented by the formula (I) in which R 1 is not a hydrogen atom can be obtained. The amount of compound (pt6) to be used is generally 1 mol to 10 mol, preferably 1 mol to 5 mol, per 1 mol of compound (B) represented by formula (I) wherein R 1 is a hydrogen atom. It is 1 mol or less, More preferably, it is 1 mol or more and 3 mol or less, More preferably, it is 1 mol or more and 2 mol or less.
　化合物（ｐｔ６）を反応させる場合、塩基を共存させることが好ましい。塩基としては、トリエチルアミン、４－（Ｎ，Ｎ－ジメチルアミノ）ピリジン、ピリジン、ピペリジン等の有機塩基；ナトリウムメトキシド、ナトリウムエトキシド、ナトリウムｔｅｒｔ－ブトキシド、カリウムｔｅｒｔ－ブトキシド等の金属アルコキシド；ブチルリチウム、ｔｅｒｔ－ブチルリチウム及びフェニルリチウム等の有機金属化合物；水酸化リチウム、水酸化ナトリウム及び水酸化カリウム等の無機塩基が挙げられる。 When reacting the compound (pt6), it is preferable to coexist with a base. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, pyridine and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide; butyllithium Organic metal compounds such as tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
　塩基の使用量は、Ｒ１が水素原子である式（Ｉ）で表される化合物（Ｂ）１モルに対し、通常１モル以上１０モル以下であり、好ましくは１モル以上５モル以下であり、より好ましくは１モル以上３モル以下であり、さらに好ましくは１モル以上２モル以下である。 The amount of the base used is usually 1 mol or more and 10 mol or less, preferably 1 mol or more and 5 mol or less, relative to 1 mol of the compound (B) represented by the formula (I) in which R 1 is a hydrogen atom. More preferably, it is 1 mol or more and 3 mol or less, More preferably, it is 1 mol or more and 2 mol or less.
　また化合物（ｐｔ６）の反応は、通常、溶媒の存在下に実施される。溶媒は、前記と同じ範囲から選択できる。 The reaction of the compound (pt6) is usually carried out in the presence of a solvent. The solvent can be selected from the same range as described above.
　溶媒の使用量は、Ｒ１が水素原子ではない式（Ｉ）で表される化合物（Ｂ）１質量部に対して、通常１質量部以上１０００質量部以下である。化合物（ｐｔ６）との反応温度は、通常－９０℃以上２００℃以下であり、好ましくは－８０℃以上１００℃以下であり、より好ましくは０℃以上５０℃以下である。反応時間は、通常０．５時間以上３００時間以下である。 The amount of the solvent used is usually 1 part by mass or more and 1000 parts by mass or less with respect to 1 part by mass of the compound (B) represented by the formula (I) in which R 1 is not a hydrogen atom. The reaction temperature with the compound (pt6) is usually −90 ° C. or higher and 200 ° C. or lower, preferably −80 ° C. or higher and 100 ° C. or lower, more preferably 0 ° C. or higher and 50 ° C. or lower. The reaction time is usually 0.5 hours or more and 300 hours or less.
　式（Ｉ）で表される化合物（Ｂ）がスルホ基を有していない場合、式（Ｉ）で表される化合物（Ｂ）と発煙硫酸又はクロロスルホン酸等のスルホ化剤とを反応させることによって、スルホ基を導入することができる。 When the compound (B) represented by the formula (I) does not have a sulfo group, the compound (B) represented by the formula (I) is reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid. Thus, a sulfo group can be introduced.
　発煙硫酸中のＳＯ３の使用量は、式（Ｉ）で表される化合物（Ｂ）１モルに対し、通常１モル以上５０モル以下であり、好ましくは５モル以上４０モル以下であり、より好ましくは５モル以上３０モル以下であり、さらに好ましくは５モル以上２５モル以下である。発煙硫酸中の硫酸の使用量は、式（Ｉ）で表される化合物（Ｂ）１モルに対し、通常１モル以上２００モル以下であり、好ましくは１０モル以上１００モル以下であり、より好ましくは１０モル以上７５モル以下であり、さらに好ましくは１０モル以上５０モル以下である。 The amount of SO 3 used in the fuming sulfuric acid is usually 1 mol or more and 50 mol or less, preferably 5 mol or more and 40 mol or less, based on 1 mol of the compound (B) represented by the formula (I). Preferably they are 5 mol or more and 30 mol or less, More preferably, they are 5 mol or more and 25 mol or less. The amount of sulfuric acid used in the fuming sulfuric acid is usually 1 mol to 200 mol, preferably 10 mol to 100 mol, and more preferably 1 mol of the compound (B) represented by the formula (I). Is from 10 mol to 75 mol, more preferably from 10 mol to 50 mol.
　クロロスルホン酸の使用量は、式（Ｉ）で表される化合物（Ｂ）１モルに対し、通常１モル以上５００モル以下であり、好ましくは１０モル以上３００モル以下であり、より好ましくは１０モル以上２００モル以下であり、さらに好ましくは１０モル以上１５０モル以下である。 The amount of chlorosulfonic acid used is usually 1 mol or more and 500 mol or less, preferably 10 mol or more and 300 mol or less, more preferably 10 mol, per 1 mol of the compound (B) represented by the formula (I). It is more than mol and 200 mol or less, More preferably, it is 10 mol or more and 150 mol or less.
　スルホ化の反応温度は、通常－２０℃以上２００℃以下であり、好ましくは－１０℃以上１００℃以下であり、より好ましくは０℃以上５０℃以下である。反応時間は、通常０．５時間以上３００時間以下である。 The reaction temperature of sulfonation is usually −20 ° C. or higher and 200 ° C. or lower, preferably −10 ° C. or higher and 100 ° C. or lower, more preferably 0 ° C. or higher and 50 ° C. or lower. The reaction time is usually 0.5 hours or more and 300 hours or less.
　式（Ｉ）で表される化合物（Ｂ）が、カルボキシ基又はスルホ基を有する場合、化合物（ｐｔ７）と化合物（ｐｔ８）とを反応させて、金属イオンＭｂ＋を含む式（Ｉ）で表される化合物（Ｂ）を製造してもよい。 When the compound (B) represented by the formula (I) has a carboxy group or a sulfo group, the compound (pt7) and the compound (pt8) are reacted with each other to represent the compound represented by the formula (I) containing the metal ion M b +. Compound (B) may be produced.
　反応混合物から、式（Ｉ）で表される化合物（Ｂ）を取り出す方法は特に限定されず、公知の種々の方法で取り出すことができる。例えば、反応終了後、反応混合物をろ過することによって式（Ｉ）で表される化合物（Ｂ）を取り出すことができる。また、ろ過した後、得られた残渣を溶媒で洗浄してもよい。また、ろ過した後、カラムクロマトグラフィー、再結晶又は昇華精製してもよい。 The method for taking out the compound (B) represented by the formula (I) from the reaction mixture is not particularly limited, and it can be taken out by various known methods. For example, after completion of the reaction, the compound (B) represented by the formula (I) can be taken out by filtering the reaction mixture. Further, after filtration, the obtained residue may be washed with a solvent. Further, after filtration, column chromatography, recrystallization, or sublimation purification may be performed.
　〔３〕Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）と、式（Ｉ）で表される化合物（Ｂ）との共分散物、及びこれを含む着色剤分散液
　着色剤分散液は、主成分としてのＣ．Ｉ．ピグメントイエロー１３８（Ａ）と、式（Ｉ）で表される化合物（Ｂ）との共分散物を含む。該共分散物を含む着色剤分散液によれば、例えば、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）の分散液と、式（Ｉ）で表される化合物（Ｂ）の分散液とを別途に調製し、これらを混合してなる着色剤分散液に比べて、有意にコントラストを向上させることができる。
　主成分とは、着色剤分散液に含まれる着色剤のうち、含有率（質量基準）が最も高い成分をいう。
　着色剤とは、顔料及び染料に代表される色素の総称をいう。 [3] C.I. I. Pigment Yellow 138 (A) and a co-dispersion of the compound (B) represented by the formula (I), and a colorant dispersion containing the same. I. Pigment Yellow 138 (A) and a compound (B) represented by the formula (I) are included. According to the colorant dispersion containing the co-dispersion, for example, C.I. I. Pigment Yellow 138 (A) dispersion and a compound (B) dispersion represented by formula (I) are prepared separately, and compared with a colorant dispersion obtained by mixing them. Can be improved.
A main component means a component with the highest content rate (mass basis) among the colorants contained in a colorant dispersion.
The colorant is a general term for pigments represented by pigments and dyes.
　共分散物は、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）とともに式（Ｉ）で表される化合物（Ｂ）を、必要に応じて分散剤の共存下に、あるいはさらに必要に応じて樹脂の共存下に、溶剤中に分散させることにより調製できる。
　分散剤としては、例えば、カチオン系、アニオン系、ノニオン系、両性、ポリエステル系、ポリアミン系、アクリル系等の界面活性剤等が挙げられる。これらの分散剤は、単独で用いてもよいし、２種以上を組み合わせて用いてもよい。
　樹脂は、後述する樹脂（Ｄ）から選択されてもよい。溶剤は、後述する溶剤（Ｇ）から選択されてもよい。
　共分散物は、例えば、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）を溶剤（Ｇ）の一部又は全部と混合し、必要に応じて分散剤の共存下に、あるいはさらに必要に応じて樹脂（Ｄ）の一部又は全部の共存下に、着色剤の平均粒子径が０．２μｍ以下程度となるまで、ビーズミル等を用いて分散させることによって調製することができる。 The co-dispersion is C.I. I. The compound (B) represented by the formula (I) together with CI Pigment Yellow 138 (A) is dispersed in a solvent in the presence of a dispersant as necessary or in the presence of a resin as necessary. Can be prepared.
Examples of the dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more.
The resin may be selected from the resin (D) described later. The solvent may be selected from the solvent (G) described later.
The co-dispersion is, for example, C.I. I. Pigment Yellow 138 (A) and the compound (B) represented by the formula (I) are mixed with a part or all of the solvent (G), and optionally in the presence of a dispersant, or further as necessary. The resin (D) can be prepared by dispersing it using a bead mill or the like until the average particle diameter of the colorant is about 0.2 μm or less in the presence of part or all of the resin (D).
　分散剤を用いる場合、その使用量は、着色剤の総量に対して、好ましくは１質量％以上１００質量％以下であり、より好ましくは５質量％以上８０質量％以下である。分散剤の使用量が上記の範囲にあると、均一な分散状態の共分散物が得られやすい傾向にある。
　樹脂を用いる場合、その使用量は、着色剤の総量に対して、好ましくは１質量％以上１００質量％以下であり、より好ましくは５質量％以上８０質量％以下である。樹脂の使用量が上記の範囲にあると、均一な分散状態の共分散物が得られやすい傾向にある。 When the dispersant is used, the amount used is preferably 1% by mass or more and 100% by mass or less, and more preferably 5% by mass or more and 80% by mass or less, with respect to the total amount of the colorant. When the amount of the dispersant used is in the above range, a co-dispersed product in a uniform dispersion state tends to be obtained.
When using resin, the usage-amount is with respect to the total amount of a coloring agent, Preferably it is 1 to 100 mass%, More preferably, it is 5 to 80 mass%. When the amount of the resin used is in the above range, a co-dispersed material in a uniform dispersion state tends to be obtained.
　共分散物及び着色剤分散液において、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）の含有量は、コントラストを高める観点から、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）の合計量１００質量部中、好ましくは５０．１質量部以上９９．９質量部以下であり、より好ましくは６０質量部以上９９質量部以下であり、さらに好ましくは８５質量部以上９９質量部以下である。
　共分散物及び着色剤分散液において、式（Ｉ）で表される化合物（Ｂ）の含有量は、コントラストを高める観点から、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）の合計量１００質量部中、好ましくは０．１質量部以上４９．９質量部以下であり、より好ましくは１質量部以上４０質量部以下であり、さらに好ましくは１質量部以上１５質量部以下である。 In the co-dispersion and colorant dispersion, C.I. I. The content of Pigment Yellow 138 (A) is C.I. I. Pigment Yellow 138 (A) and Compound (B) represented by Formula (I) in a total amount of 100 parts by mass, preferably 50.1 parts by mass to 99.9 parts by mass, more preferably 60 parts by mass. It is 99 mass parts or less, More preferably, it is 85 mass parts or more and 99 mass parts or less.
In the co-dispersion and the colorant dispersion, the content of the compound (B) represented by the formula (I) is C.I. I. Pigment Yellow 138 (A) and Compound (B) represented by Formula (I) in a total amount of 100 parts by mass, preferably 0.1 parts by mass or more and 49.9 parts by mass or less, more preferably 1 part by mass. It is 40 mass parts or less, More preferably, it is 1 mass part or more and 15 mass parts or less.
　共分散物及び着色剤分散液は、それぞれ、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）以外の他の成分を含むことができる。
　他の成分としては、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）以外の他の着色剤（顔料、染料）、溶剤、分散剤、樹脂、脂肪族カルボン酸金属塩（Ｃ）等が挙げられる。脂肪族カルボン酸金属塩（Ｃ）については後述する。
　共分散物及び着色剤分散液は、それぞれ、他の成分を１種のみ含んでいてもよいし、２種以上含んでいてもよい。 The co-dispersion and the colorant dispersion are respectively C.I. I. Other components than the pigment yellow 138 (A) and the compound (B) represented by the formula (I) can be included.
Other components include C.I. I. Pigment Yellow 138 (A) and other colorants (pigments, dyes) other than the compound (B) represented by Formula (I), solvents, dispersants, resins, aliphatic carboxylic acid metal salts (C), and the like. It is done. The aliphatic carboxylic acid metal salt (C) will be described later.
Each of the co-dispersion and the colorant dispersion may contain only one type of other component, or may contain two or more types.
　他の顔料としては、特に限定されず公知の顔料を使用することができ、例えば、カラーインデックス（The Society of Dyers and Colourists出版）でピグメントに分類されている顔料が挙げられる。
　顔料としては、例えば、
　Ｃ．Ｉ．ピグメントイエロー１、３、１２、１３、１４、１５、１６、１７、２０、２４、３１、５３、８３、８６、９３、９４、１０９、１１０、１１７、１２５、１２８、１３７、１３９、１４７、１４８、１５０、１５３、１５４、１６６、１７３、１８５、１９４、２１４等の黄色顔料；
　Ｃ．Ｉ．ピグメントオレンジ１３、３１、３６、３８、４０、４２、４３、５１、５５、５９、６１、６４、６５、７１、７３等のオレンジ色顔料；
　Ｃ．Ｉ．ピグメントレッド９、９７、１０５、１２２、１２３、１４４、１４９、１６６、１６８、１７６、１７７、１８０、１９２、２０９、２１５、２１６、２２４、２４２、２５４、２５５、２６４、２６５等の赤色顔料；
　Ｃ．Ｉ．ピグメントブルー１５、１５：３、１５：４、１５：６、６０等の青色顔料；
　Ｃ．Ｉ．ピグメントバイオレット１、１９、２３、２９、３２、３６、３８等のバイオレット色顔料；
　Ｃ．Ｉ．ピグメントグリーン７、３６、５８、５９等の緑色顔料；
　Ｃ．Ｉ．ピグメントブラウン２３、２５等のブラウン色顔料；
　Ｃ．Ｉ．ピグメントブラック１、７等の黒色顔料；
等が挙げられる。 Other pigments are not particularly limited, and publicly known pigments can be used. Examples thereof include pigments classified as pigments according to the color index (published by The Society of Dyers and Colorists).
As a pigment, for example,
C. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 139, 147, Yellow pigments such as 148, 150, 153, 154, 166, 173, 185, 194, 214;
C. I. Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
C. I. Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265;
C. I. Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60;
C. I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38;
C. I. Green pigments such as CI Pigment Green 7, 36, 58, 59;
C. I. Brown pigments such as CI Pigment Brown 23 and 25;
C. I. Black pigments such as CI Pigment Black 1 and 7;
Etc.
　他の顔料は、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）ともに共分散物中に共分散されていてもよいし、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）を含む共分散物に添加されて着色剤分散液に含まれていてもよい。 Other pigments are C.I. I. Pigment Yellow 138 (A) and the compound (B) represented by the formula (I) may be co-dispersed in the co-dispersion, or C.I. I. Pigment Yellow 138 (A) and the co-dispersion containing the compound (B) represented by the formula (I) may be added to the colorant dispersion.
　Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）、式（Ｉ）で表される化合物（Ｂ）及び他の顔料は、必要に応じて、ロジン処理、酸性基又は塩基性基が導入された顔料誘導体等を用いた表面処理、高分子化合物等による顔料表面へのグラフト処理、硫酸微粒化法等による微粒化処理、又は不純物を除去するための有機溶剤や水等による洗浄処理、イオン性不純物のイオン交換法等による除去処理等が施されていてもよい。 C. I. Pigment Yellow 138 (A), the compound (B) represented by the formula (I), and other pigments, if necessary, a surface using a rosin treatment, a pigment derivative having an acidic group or a basic group introduced, or the like Treatment, grafting to the pigment surface with polymer compounds, atomization by sulfuric acid atomization method, etc., washing treatment with organic solvent or water to remove impurities, removal of ionic impurities by ion exchange method, etc. Processing etc. may be given.
　染料としては、特に限定されず公知の染料を使用することができ、例えば、溶剤染料、酸性染料、直接染料、媒染染料等が挙げられる。
　染料としては、例えば、カラーインデックス（The Society of Dyers and Colourists出版）及び染色ノート（色染社）に記載されている公知の染料が挙げられる。
　また、化学構造によれば、染料としては、アゾ染料、シアニン染料、トリフェニルメタン染料、キサンテン染料、フタロシアニン染料、アントラキノン染料、ナフトキノン染料、キノンイミン染料、メチン染料、アゾメチン染料、スクアリリウム染料、アクリジン染料、スチリル染料、クマリン染料、キノリン染料及びニトロ染料等が挙げられる。これらのうち、有機溶剤可溶性染料が好ましい。
　染料は、共分散物に含まれていてもよいし、共分散物に添加されて着色剤分散液に含まれていてもよい。 It does not specifically limit as a dye, A well-known dye can be used, For example, a solvent dye, an acid dye, a direct dye, a mordant dye etc. are mentioned.
Examples of the dye include known dyes described in Color Index (published by The Society of Dyers and Colorists) and dyeing notes (Color Dyeing).
In addition, according to the chemical structure, the dyes include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, Examples include styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Of these, organic solvent-soluble dyes are preferred.
The dye may be contained in the co-dispersion, or may be added to the co-dispersion and contained in the colorant dispersion.
　樹脂は、後述する樹脂（Ｄ）から選択されてもよい。溶剤は、後述する溶剤（Ｇ）から選択されてもよい。 Resin may be selected from the resin (D) described below. The solvent may be selected from the solvent (G) described later.
　Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）の合計含有量は、共分散物又は着色剤分散液に含まれる着色剤１００質量部中、好ましくは５質量部以上であり、より好ましくは１０質量部以上であり、さらに好ましくは３０質量部以上であり、よりさらに好ましくは５０質量部以上であり、とりわけ好ましくは８０質量部以上であり、最も好ましくは９０質量部以上である。上記合計含有量は、共分散物又は着色剤分散液に含まれる着色剤１００質量部中、１００質量部であってもよい。 C. I. The total content of the pigment yellow 138 (A) and the compound (B) represented by the formula (I) is preferably 5 parts by mass or more in 100 parts by mass of the colorant contained in the co-dispersion or the colorant dispersion. More preferably 10 parts by mass or more, still more preferably 30 parts by mass or more, still more preferably 50 parts by mass or more, particularly preferably 80 parts by mass or more, and most preferably 90 parts by mass or more. It is. The total content may be 100 parts by mass in 100 parts by mass of the colorant contained in the co-dispersion or the colorant dispersion.
　Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）の合計含有量は、共分散物又は着色剤分散液に含まれる固形分の総量１００質量部中、好ましくは１０質量部以上９０質量部以下であり、より好ましくは１５質量部以上８０質量部以下であり、さらに好ましくは２０質量部以上７０質量部以下である。
　本明細書において、共分散物、着色剤分散液又は着色硬化性樹脂組成物に含まれる「固形分の総量」とは、共分散物、着色剤分散液又は着色硬化性樹脂組成物の総量から溶剤の含有量を除いた量のことをいう。固形分の総量及びこれに対する各成分の含有量は、例えば、液体クロマトグラフィー又はガスクロマトグラフィー等の公知の分析手段で測定することができる。 C. I. The total content of Pigment Yellow 138 (A) and the compound (B) represented by the formula (I) is preferably 10 parts by mass in the total amount of solids contained in the co-dispersion or the colorant dispersion. It is 90 parts by mass or less, more preferably 15 parts by mass or more and 80 parts by mass or less, and further preferably 20 parts by mass or more and 70 parts by mass or less.
In the present specification, the “total amount of solids” contained in the co-dispersion, colorant dispersion or colored curable resin composition refers to the total amount of the co-dispersion, colorant dispersion or colored curable resin composition. The amount excluding the solvent content. The total amount of solids and the content of each component relative thereto can be measured by known analytical means such as liquid chromatography or gas chromatography, for example.
　〔４〕脂肪族カルボン酸金属塩（Ｃ）
　着色剤分散液は、上記他の成分として、脂肪族カルボン酸金属塩（Ｃ）を含むことができる。脂肪族カルボン酸金属塩（Ｃ）をさらに含有させることは、コントラスト向上に有利となる。
　脂肪族カルボン酸金属塩（Ｃ）は、共分散物に含まれていてもよいし、共分散物に添加されて着色剤分散液に含まれていてもよい。 [4] Aliphatic carboxylic acid metal salt (C)
The colorant dispersion may contain an aliphatic carboxylic acid metal salt (C) as the other component. Further inclusion of the aliphatic carboxylic acid metal salt (C) is advantageous for improving the contrast.
The aliphatic carboxylic acid metal salt (C) may be contained in the co-dispersion, or may be added to the co-dispersion and contained in the colorant dispersion.
　脂肪族カルボン酸金属塩（Ｃ）は、金属カチオンと、ヒドロキシ基を有する炭素数１～４０の脂肪族カルボン酸のアニオンとからなる塩である。以下、ヒドロキシ基を有する炭素数１～４０の脂肪族カルボン酸を「脂肪族カルボン酸（Ｘ）」ともいう。
　本明細書において「脂肪族カルボン酸」とは、芳香環を有さないカルボン酸を意味する。
　本発明の着色硬化性樹脂組成物は、脂肪族カルボン酸金属塩（Ｃ）を１種のみ含んでいてもよいし、２種以上含んでいてもよい。 The aliphatic carboxylic acid metal salt (C) is a salt composed of a metal cation and an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms having a hydroxy group. Hereinafter, the aliphatic carboxylic acid having 1 to 40 carbon atoms having a hydroxy group is also referred to as “aliphatic carboxylic acid (X)”.
As used herein, “aliphatic carboxylic acid” means a carboxylic acid having no aromatic ring.
The colored curable resin composition of the present invention may contain only one type of aliphatic carboxylic acid metal salt (C), or may contain two or more types.
　脂肪族カルボン酸（Ｘ）は、カルボキシ基の炭素も含めた炭素数が１～４０であり、直鎖状であってもよいし、分岐鎖状であってもよいし、環状であってもよく、直鎖状構造、分岐鎖構造及び環状構造からなる群より選択される２種以上の構造を組み合わせたものであってもよい。
　脂肪族カルボン酸（Ｘ）は不飽和結合を含んでいてもよい。 The aliphatic carboxylic acid (X) has 1 to 40 carbon atoms including carbon of the carboxy group, and may be linear, branched or cyclic. It may be a combination of two or more structures selected from the group consisting of a linear structure, a branched chain structure and a cyclic structure.
The aliphatic carboxylic acid (X) may contain an unsaturated bond.
　脂肪族カルボン酸（Ｘ）は、分子内にヒドロキシ基を１以上有する。
　脂肪族カルボン酸（Ｘ）は、分子内にカルボキシ基を１以上有する。カルボキシ基の数は、通常１０以下である。 The aliphatic carboxylic acid (X) has one or more hydroxy groups in the molecule.
The aliphatic carboxylic acid (X) has one or more carboxy groups in the molecule. The number of carboxy groups is usually 10 or less.
　脂肪族カルボン酸（Ｘ）の炭素数は、コントラストを高める観点から、１～４０であり、好ましくは１０～３６であり、より好ましくは１２～２４である。 The carbon number of the aliphatic carboxylic acid (X) is from 1 to 40, preferably from 10 to 36, more preferably from 12 to 24, from the viewpoint of enhancing the contrast.
　脂肪族カルボン酸金属塩（Ｃ）は、脂肪族カルボン酸（Ｘ）のアニオンを少なくとも１つ有していればよい。脂肪族カルボン酸金属塩（Ｃ）が有する金属カチオンの価数が２以上である場合、脂肪族カルボン酸金属塩（Ｃ）は、２種以上の脂肪族カルボン酸（Ｘ）のアニオンを有していてもよく、脂肪族カルボン酸（Ｘ）のアニオンと、脂肪族カルボン酸（Ｘ）のアニオン以外の他のアニオンとを有していてもよい。
　上記他のアニオンとしては特に制限されず、ハロゲンイオン、硝酸イオン、硫酸イオン等であってもよいが、好ましくは脂肪族カルボン酸（Ｘ）以外の脂肪族カルボン酸のアニオンである。
　脂肪族カルボン酸（Ｘ）以外の脂肪族カルボン酸とは、ヒドロキシ基を有さない脂肪族カルボン酸を意味し、例えば、ヒドロキシ基を有しない以外は、脂肪族カルボン酸（Ｘ）と同様の構造を有するものが挙げられる。
　脂肪族カルボン酸金属塩（Ｃ）が有するアニオンは、脂肪族カルボン酸（Ｘ）のアニオンのみから構成されることが好ましい。 The aliphatic carboxylic acid metal salt (C) only needs to have at least one anion of the aliphatic carboxylic acid (X). When the valence of the metal cation of the aliphatic carboxylic acid metal salt (C) is 2 or more, the aliphatic carboxylic acid metal salt (C) has two or more kinds of anions of the aliphatic carboxylic acid (X). It may have an anion of aliphatic carboxylic acid (X) and an anion other than the anion of aliphatic carboxylic acid (X).
The other anion is not particularly limited and may be a halogen ion, a nitrate ion, a sulfate ion, or the like, but is preferably an anion of an aliphatic carboxylic acid other than the aliphatic carboxylic acid (X).
The aliphatic carboxylic acid other than the aliphatic carboxylic acid (X) means an aliphatic carboxylic acid having no hydroxy group. For example, the aliphatic carboxylic acid (X) is the same as the aliphatic carboxylic acid (X) except having no hydroxy group. The thing which has a structure is mentioned.
The anion contained in the aliphatic carboxylic acid metal salt (C) is preferably composed only of the anion of the aliphatic carboxylic acid (X).
　脂肪族カルボン酸金属塩（Ｃ）が有する金属カチオンは、コントラストを高める観点から、２価以上１０価以下の金属カチオンであることが好ましい。２価以上の金属カチオンとしては、元素の周期律表の２族～１５族に属する金属のカチオンが挙げられる。金属カチオンは、好ましくは２価以上６価以下の金属カチオンである。
　金属カチオンは、
　より好ましくは、Ｍｇ２＋、Ｃａ２＋、Ｓｒ２＋、Ｂａ２＋、Ｃｄ２＋、Ｎｉ２＋、Ｚｎ２＋、Ｃｕ２＋、Ｈｇ２＋、Ｆｅ２＋、Ｃｏ２＋、Ｓｎ２＋、Ｐｂ２＋及びＭｎ２＋等の２価の金属カチオン;Ａｌ３＋、Ｆｅ３＋、Ｃｏ３＋及びＣｒ３＋等の３価の金属カチオン；Ｓｎ４＋及びＭｎ４＋等の４価の金属カチオンであり、
　さらに好ましくは、Ｍｇ２＋、Ｃａ２＋、Ｓｒ２＋、Ｂａ２＋、Ｎｉ２＋、Ｚｎ２＋、Ｃｕ２＋、Ｆｅ２＋、Ｃｏ２＋、Ｓｎ２＋、Ｍｎ２＋、Ａｌ３＋、Ｆｅ３＋、Ｃｏ３＋、Ｃｒ３＋、Ｓｎ４＋及びＭｎ４＋であり、
　とりわけ好ましくは、Ｍｇ２＋、Ｃａ２＋、Ｓｒ２＋、Ｂａ２＋、Ｎｉ２＋、Ｚｎ２＋、Ｃｕ２＋、Ｆｅ２＋、Ｃｏ２＋、Ｍｎ２＋、Ａｌ３＋、Ｆｅ３＋、Ｃｏ３＋、Ｃｒ３＋及びＭｎ４＋であり、
　一層好ましくは、Ｆｅ２＋、Ｃｏ２＋、Ｆｅ３＋及びＣｏ３＋である。
　脂肪族カルボン酸金属塩（Ａ）は、２種以上の金属カチオンを有していてもよい。 The metal cation possessed by the aliphatic carboxylic acid metal salt (C) is preferably a metal cation having a valence of not less than 10 and not more than 10 from the viewpoint of enhancing contrast. Examples of the bivalent or higher metal cation include cations of metals belonging to Groups 2 to 15 of the periodic table of elements. The metal cation is preferably a divalent to hexavalent metal cation.
Metal cations are
More preferably, divalent such as Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Cd 2+ , Ni 2+ , Zn 2+ , Cu 2+ , Hg 2+ , Fe 2+ , Co 2+ , Sn 2+ , Pb 2+ and Mn 2+. A metal cation; a trivalent metal cation such as Al 3+ , Fe 3+ , Co 3+ and Cr 3+ ; a tetravalent metal cation such as Sn 4+ and Mn 4+ ,
More preferably, Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Ni 2+ , Zn 2+ , Cu 2+ , Fe 2+ , Co 2+ , Sn 2+ , Mn 2+ , Al 3+ , Fe 3+ , Co 3+ , Cr 3+ , Sn 4+ and Mn 4+ ,
Especially preferred are Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Ni 2+ , Zn 2+ , Cu 2+ , Fe 2+ , Co 2+ , Mn 2+ , Al 3+ , Fe 3+ , Co 3+ , Cr 3+ and Mn 4+ . ,
More preferred are Fe 2+ , Co 2+ , Fe 3+ and Co 3+ .
The aliphatic carboxylic acid metal salt (A) may have two or more kinds of metal cations.
　脂肪族カルボン酸金属塩（Ｃ）は、具体的には、以下の式（Ａａ）で表される化合物であってよい。 Specifically, the aliphatic carboxylic acid metal salt (C) may be a compound represented by the following formula (Aa).
Figure JPOXMLDOC01-appb-I000037
Figure JPOXMLDOC01-appb-I000037
［式（Ａａ）中、
　Ｄは、ヒドロキシ基を有する脂肪族炭化水素を表す。
　ａは、１～１０のいずれかの整数を表し、好ましくは１～３のいずれかの整数である。ａが複数存在するとき、それらは互いに同じであってもよく、異なっていてもよい。
　Ｄの炭素数＋ａは、１～４０のいずれかの整数である。
　ｂは、１以上のいずれかの整数を表す。ｂが２以上のいずれかの整数を表すとき、『［Ｄ］－（ＣＯ２ －）ａ』は互いに同じであってもよく、異なっていてもよい。
　Ｊｋ－は、『［Ｄ］－（ＣＯ２ －）ａ』以外のアニオンを表す。
　ｋは、１～１０のいずれかの整数を表し、好ましくは１～６のいずれかの整数である。
　ｍは、０以上のいずれかの整数を表す。ｍが２以上のいずれかの整数を表すとき、『Ｊｋ－』は互いに同じであってもよく、異なっていてもよい。
　Ａｃ＋は、ｃ価の金属カチオンを表し、具体例は上述のとおりである。
　ｃは、２～１０のいずれかの整数を表し、好ましくは２～６のいずれかの整数である。
　ｄは、１以上のいずれかの整数を表す。ｄが２以上のいずれかの整数を表すとき、『Ａｃ＋』は互いに同じであってもよく、異なっていてもよい。
　ただし、
Figure JPOXMLDOC01-appb-I000038
及び
Figure JPOXMLDOC01-appb-I000039
の合計の価数と、
Figure JPOXMLDOC01-appb-I000040
の価数とは等しい。］ [In the formula (Aa),
D represents an aliphatic hydrocarbon having a hydroxy group.
a represents an integer of 1 to 10, and preferably an integer of 1 to 3. When a plurality are present, they may be the same as or different from each other.
The carbon number + a of D is an integer of 1 to 40.
b represents any integer of 1 or more. When b represents any integer of 2 or more, “[D]-(CO 2 − ) a ” may be the same as or different from each other.
J k- represents an anion other than “[D]-(CO 2 − ) a ”.
k represents an integer of 1 to 10, preferably an integer of 1 to 6.
m represents any integer of 0 or more. When m represents any integer of 2 or more, “J k− ” may be the same as or different from each other.
A c + represents a c-valent metal cation, and specific examples thereof are as described above.
c represents an integer of 2 to 10, preferably an integer of 2 to 6.
d represents any integer of 1 or more. When d represents any integer of 2 or more, “A c + ” may be the same as or different from each other.
However,
Figure JPOXMLDOC01-appb-I000038
as well as
Figure JPOXMLDOC01-appb-I000039
And the total valence of
Figure JPOXMLDOC01-appb-I000040
Is equal to the valence of. ]
　脂肪族カルボン酸金属塩（Ｃ）は、例えば、脂肪族カルボン酸（Ｘ）をアルカリ水溶液に溶解させた後、金属カチオンを有する塩（例えばハロゲン化物等）を添加することによって生じる沈殿物として得ることができる。得られた脂肪族カルボン酸金属塩（Ｃ）は、必要に応じて、洗浄等の精製処理に供されてもよい。 The aliphatic carboxylic acid metal salt (C) is obtained, for example, as a precipitate generated by dissolving the aliphatic carboxylic acid (X) in an alkaline aqueous solution and then adding a salt having a metal cation (such as a halide). be able to. The obtained aliphatic carboxylic acid metal salt (C) may be subjected to purification treatment such as washing, if necessary.
　脂肪族カルボン酸金属塩（Ｃ）としては、具体的には、例えば、下記の式（ＡＡ）において、Ｍ、Ｌ、ｐ及びｑが各々、下記の［表Ａ］で表される化合物、［表Ａ］の化合物ＡＡ１～ＡＡ２２において、ＭがＦｅ２＋の代わりにＭｇ２＋、Ｃａ２＋、Ｓｒ２＋、Ｂａ２＋、Ｃｄ２＋、Ｎｉ２＋、Ｚｎ２＋、Ｃｕ２＋、Ｈｇ２＋、Ｃｏ２＋、Ｓｎ２＋、Ｐｂ２＋、又はＭｎ２＋である化合物、［表Ｂ］で表される化合物、［表Ｂ］の化合物ＡＡ２３～ＡＡ４４において、ＭがＦｅ３＋の代わりにＡｌ３＋、Ｃｏ３＋又はＣｒ３＋である化合物、及び［表Ｃ］で表される化合物が挙げられる。
　　　　ＭｐＬｑ　　　（ＡＡ） Specifically, as the aliphatic carboxylic acid metal salt (C), for example, in the following formula (AA), M, L, p and q are each a compound represented by the following [Table A], [ in the compounds AA1 ~ AA22 Table a], Mg 2+ instead of M is Fe 2+, Ca 2+, Sr 2+ , Ba 2+, Cd 2+, Ni 2+, Zn 2+, Cu 2+, Hg 2+, Co 2+, Sn 2+, A compound represented by Pb 2+ or Mn 2+ , a compound represented by [Table B], a compound AA23 to AA44 of [Table B], wherein M is Al 3+ , Co 3+ or Cr 3+ instead of Fe 3+ , And compounds represented by [Table C].
M p L q (AA)
Figure JPOXMLDOC01-appb-I000041
Figure JPOXMLDOC01-appb-I000041
Figure JPOXMLDOC01-appb-I000042
Figure JPOXMLDOC01-appb-I000042
Figure JPOXMLDOC01-appb-I000043
Figure JPOXMLDOC01-appb-I000043
Figure JPOXMLDOC01-appb-I000044
Figure JPOXMLDOC01-appb-I000044
　また、脂肪族カルボン酸（Ｘ）のアニオンと、脂肪族カルボン酸（Ｘ）のアニオン以外の他のアニオンとを有する脂肪族カルボン酸金属塩（Ｃ）としては、例えば下記式で表される塩が挙げられる。 Examples of the aliphatic carboxylic acid metal salt (C) having an anion of the aliphatic carboxylic acid (X) and an anion other than the anion of the aliphatic carboxylic acid (X) include, for example, a salt represented by the following formula: Is mentioned.
Figure JPOXMLDOC01-appb-I000045
Figure JPOXMLDOC01-appb-I000045
　共分散物又は着色剤分散液が脂肪族カルボン酸金属塩（Ｃ）を含む場合、脂肪族カルボン酸金属塩（Ｃ）の含有量は、共分散物又は着色剤分散液に含まれる固形分の総量１００質量部中、好ましくは０．０１質量部以上２５質量部以下であり、より好ましくは０．１質量部以上２０質量部以下であり、さらに好ましくは０．２質量部以上１５質量部以下であり、とりわけ好ましくは０．３質量部以上１０質量部以下である。脂肪族カルボン酸金属塩（Ｃ）の含有量が上記の範囲内にあると、コントラストを有意に向上させることができる。
　また、脂肪族カルボン酸金属塩（Ｃ）の含有量は、Ｃ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）の合計量１００質量部に対して、好ましくは０．１質量部以上２０質量部以下であり、より好ましくは０．３質量部以上１５質量部以下であり、さらに好ましくは０．５質量部以上１３質量部以下である。 When the co-dispersion or the colorant dispersion contains the aliphatic carboxylic acid metal salt (C), the content of the aliphatic carboxylic acid metal salt (C) is the solid content contained in the co-dispersion or the colorant dispersion. The total amount is 100 parts by mass, preferably 0.01 parts by mass or more and 25 parts by mass or less, more preferably 0.1 parts by mass or more and 20 parts by mass or less, and further preferably 0.2 parts by mass or more and 15 parts by mass or less. Especially preferably, it is 0.3 mass part or more and 10 mass parts or less. When the content of the aliphatic carboxylic acid metal salt (C) is within the above range, the contrast can be significantly improved.
The content of the aliphatic carboxylic acid metal salt (C) is C.I. I. Preferably they are 0.1 mass part or more and 20 mass parts or less with respect to 100 mass parts of total amounts of the compound (B) represented by pigment yellow 138 (A) and Formula (I), More preferably, it is 0.3. It is not less than 15 parts by mass and more preferably not less than 0.5 parts by mass and not more than 13 parts by mass.
　＜着色硬化性樹脂組成物＞
　着色硬化性樹脂組成物は、上記着色剤分散液と、樹脂（Ｄ）とを含む。
　着色硬化性樹脂組成物は、重合性化合物（Ｅ）及び重合開始剤（Ｆ）をさらに含むことが好ましく、重合性化合物（Ｅ）、重合開始剤（Ｆ）及び溶剤（Ｇ）をさらに含むことがより好ましい。
　着色硬化性樹脂組成物は、重合開始助剤（Ｆ１）及び／又はレベリング剤（Ｈ）をさらに含んでいてもよい。
　上記着色硬化性樹脂組成物によれば、それから形成されるカラーフィルタ及びそれを用いた表示装置のコントラストを良好なものとすることができる。
　以下、各成分として例示する化合物は、特に断りのない限り、単独で又は複数種を組み合わせて使用することができる。 <Colored curable resin composition>
The colored curable resin composition contains the colorant dispersion and the resin (D).
The colored curable resin composition preferably further includes a polymerizable compound (E) and a polymerization initiator (F), and further includes a polymerizable compound (E), a polymerization initiator (F), and a solvent (G). Is more preferable.
The colored curable resin composition may further contain a polymerization initiation assistant (F1) and / or a leveling agent (H).
According to the said colored curable resin composition, the color filter formed from it and the contrast of a display apparatus using the same can be made favorable.
Hereinafter, unless otherwise indicated, the compound illustrated as each component can be used individually or in combination of multiple types.
　〔１〕着色硬化性樹脂組成物における着色剤分散液の含有量
　明度の観点から、着色剤分散液は、それに含まれる着色剤の含有量（又はＣ．Ｉ．ピグメントイエロー１３８（Ａ）及び式（Ｉ）で表される化合物（Ｂ）の合計含有量）が、着色硬化性樹脂組成物の固形分の総量１００質量部中、好ましくは０．１質量部以上９０質量部以下、より好ましくは０．５質量部以上８０質量部以下、さらに好ましくは１質量部以上７０質量部以下となるように、着色硬化性樹脂組成物に含有される。 [1] Content of Colorant Dispersion in Colored Curable Resin Composition From the viewpoint of lightness, the colorant dispersion contains the content of the colorant contained therein (or CI Pigment Yellow 138 (A) and the formula The total content of the compound (B) represented by (I)) is preferably 100 parts by mass or more and more preferably 90 parts by mass or less, more preferably 100 parts by mass or less, more preferably 100 parts by mass of the solid content of the colored curable resin composition. It is contained in the colored curable resin composition so as to be 0.5 parts by mass or more and 80 parts by mass or less, more preferably 1 part by mass or more and 70 parts by mass or less.
　〔２〕樹脂（Ｄ）
　樹脂（Ｄ）は、特に限定されないが、アルカリ可溶性樹脂であることが好ましく、不飽和カルボン酸及び不飽和カルボン酸無水物からなる群より選ばれる少なくとも一種（ａ）（以下「（ａ）」ということがある。）に由来する構造単位を有する樹脂がより好ましい。
　樹脂（Ｄ）は、さらに、炭素数２～４の環状エーテル構造とエチレン性不飽和結合とを有する単量体（ｂ）（以下「（ｂ）」ということがある。）に由来する構造単位、（ａ）と共重合可能な単量体（ｃ）（ただし、（ａ）及び（ｂ）とは異なる。）（以下「（ｃ）」ということがある。）に由来する構造単位、並びに、側鎖にエチレン性不飽和結合を有する構造単位からなる群より選ばれる少なくとも一種の構造単位を有することが好ましい。 [2] Resin (D)
The resin (D) is not particularly limited, but is preferably an alkali-soluble resin, and is at least one selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride (hereinafter referred to as “(a)”). A resin having a structural unit derived from (.
The resin (D) further includes a structural unit derived from the monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”). , (A) a copolymerizable monomer (c) (however, different from (a) and (b)) (hereinafter sometimes referred to as “(c)”), and It is preferable to have at least one structural unit selected from the group consisting of structural units having an ethylenically unsaturated bond in the side chain.
　（ａ）としては、例えば、アクリル酸、メタクリル酸、無水マレイン酸、イタコン酸無水物、３，４，５，６－テトラヒドロフタル酸無水物、こはく酸モノ〔２－（メタ）アクリロイルオキシエチル〕等が挙げられ、好ましくは、アクリル酸、メタクリル酸、無水マレイン酸である。 Examples of (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and succinic acid mono [2- (meth) acryloyloxyethyl]. Among them, acrylic acid, methacrylic acid, and maleic anhydride are preferable.
　（ｂ）は、炭素数２～４の環状エーテル構造（例えば、オキシラン環、オキセタン環及びテトラヒドロフラン環からなる群より選ばれる少なくとも一種）と（メタ）アクリロイルオキシ基とを有する単量体であることが好ましい。
　なお、本明細書において、「（メタ）アクリル酸」とは、アクリル酸及びメタクリル酸からなる群より選ばれる少なくとも一種を表す。「（メタ）アクリロイル」及び「（メタ）アクリレート」等の表記も、同様の意味を有する。
　（ｂ）としては、例えば、グリシジル（メタ）アクリレート、ビニルベンジルグリシジルエーテル、３，４－エポキシトリシクロ［５．２．１．０２，６］デシル（メタ）アクリレート、３－エチル－３－（メタ）アクリロイルオキシメチルオキセタン、テトラヒドロフルフリル（メタ）アクリレート等が挙げられ、好ましくは、グリシジル（メタ）アクリレート、３，４－エポキシトリシクロ［５．２．１．０２，６］デシル（メタ）アクリレート、３－エチル－３－（メタ）アクリロイルオキシメチルオキセタンである。 (B) is a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and a (meth) acryloyloxy group. Is preferred.
In the present specification, “(meth) acrylic acid” represents at least one selected from the group consisting of acrylic acid and methacrylic acid. Notations such as “(meth) acryloyl” and “(meth) acrylate” have the same meaning.
Examples of (b) include glycidyl (meth) acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl (meth) acrylate, 3-ethyl-3- (Meth) acryloyloxymethyloxetane, tetrahydrofurfuryl (meth) acrylate, and the like can be mentioned. Preferably, glycidyl (meth) acrylate, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decyl ( (Meth) acrylate, 3-ethyl-3- (meth) acryloyloxymethyloxetane.
　（ｃ）としては、例えば、メチル（メタ）アクリレート、ブチル（メタ）アクリレートシクロヘキシル（メタ）アクリレート、２－メチルシクロヘキシル（メタ）アクリレート、トリシクロ［５．２．１．０２，６］デカン－８－イル（メタ）アクリレート、ベンジル（メタ）アクリレート、２－ヒドロキシエチル（メタ）アクリレート、Ｎ－フェニルマレイミド、Ｎ－シクロヘキシルマレイミド、Ｎ－ベンジルマレイミド、スチレン、ビニルトルエン等が挙げられ、好ましくは、スチレン、ビニルトルエン、２－ヒドロキシエチル（メタ）アクリレート、Ｎ－フェニルマレイミド、Ｎ－シクロヘキシルマレイミド、Ｎ－ベンジルマレイミド等が好ましい。 Examples of (c) include methyl (meth) acrylate, butyl (meth) acrylate cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, and tricyclo [5.2.1.0 2,6 ] decane-8. -Yl (meth) acrylate, benzyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene, etc., preferably styrene Vinyl toluene, 2-hydroxyethyl (meth) acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide and the like are preferable.
　側鎖にエチレン性不飽和結合を有する構造単位を有する樹脂は、（ａ）と（ｃ）との共重合体に（ｂ）を付加させるか、（ｂ）と（ｃ）との共重合体に（ａ）を付加させることにより製造することができる。該樹脂は、（ｂ）と（ｃ）との共重合体に（ａ）を付加させさらにカルボン酸無水物を反応させた樹脂であってもよい。 A resin having a structural unit having an ethylenically unsaturated bond in the side chain is obtained by adding (b) to a copolymer of (a) and (c) or a copolymer of (b) and (c) It can be produced by adding (a) to. The resin may be a resin obtained by adding (a) to a copolymer of (b) and (c) and further reacting with a carboxylic acid anhydride.
　樹脂（Ｄ）のポリスチレン換算の重量平均分子量は、好ましくは３０００以上１０００００以下であり、より好ましくは５０００以上５００００以下であり、さらに好ましくは５０００以上３００００以下である。
　樹脂（Ｄ）の分散度［重量平均分子量（Ｍｗ）／数平均分子量（Ｍｎ）］は、好ましくは１．１以上６以下であり、より好ましくは１．２以上４以下である。 The polystyrene equivalent weight average molecular weight of the resin (D) is preferably 3000 or more and 100,000 or less, more preferably 5000 or more and 50000 or less, and further preferably 5000 or more and 30000 or less.
The dispersity [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (D) is preferably 1.1 or more and 6 or less, more preferably 1.2 or more and 4 or less.
　樹脂（Ｄ）の酸価は、固形分換算で、好ましくは２０ｍｇ－ＫＯＨ／ｇ以上１７０ｍｇ－ＫＯＨ／ｇ以下であり、より好ましくは３０ｍｇ－ＫＯＨ／ｇ以上１５０ｍｇ－ＫＯＨ／ｇ以下、さらに好ましくは４０ｍｇ－ＫＯＨ／ｇ以上１３５ｍｇ－ＫＯＨ／ｇ以下である。
　酸価は、樹脂（Ｄ）１ｇを中和するために必要な水酸化カリウムの量（ｍｇ）として測定される値であり、例えば水酸化カリウム水溶液を用いて滴定することにより求めることができる。 The acid value of the resin (D) is preferably 20 mg-KOH / g or more and 170 mg-KOH / g or less, more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, more preferably in terms of solid content. It is 40 mg-KOH / g or more and 135 mg-KOH / g or less.
The acid value is a value measured as the amount (mg) of potassium hydroxide necessary to neutralize 1 g of the resin (D), and can be determined by titration with an aqueous potassium hydroxide solution, for example.
　樹脂（Ｄ）の含有量は、着色硬化性樹脂組成物の固形分の総量１００質量部中、好ましくは７質量部以上６５質量部以下であり、より好ましくは１３質量部以上６０質量部以下であり、さらに好ましくは１７質量部以上５５質量部以下である。 The content of the resin (D) is preferably 7 parts by mass or more and 65 parts by mass or less, more preferably 13 parts by mass or more and 60 parts by mass or less, in a total amount of 100 parts by mass of the solid content of the colored curable resin composition. Yes, more preferably 17 parts by mass or more and 55 parts by mass or less.
　〔３〕重合性化合物（Ｅ）
　重合性化合物（Ｅ）は、重合開始剤（Ｆ）から発生した活性ラジカル及び／又は酸によって重合し得る化合物であり、例えば、重合性のエチレン性不飽和結合を有する化合物等が挙げられ、好ましくは（メタ）アクリル酸エステル化合物である。 [3] Polymerizable compound (E)
The polymerizable compound (E) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (F), and examples thereof include a compound having a polymerizable ethylenically unsaturated bond. Is a (meth) acrylic acid ester compound.
　中でも、重合性化合物（Ｅ）は、エチレン性不飽和結合を３つ以上有する重合性化合物であることが好ましい。このような重合性化合物としては、例えば、トリメチロールプロパントリ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、ジペンタエリスリトールペンタ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレート等が挙げられる。 Of these, the polymerizable compound (E) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa ( And (meth) acrylate.
　重合性化合物（Ｅ）の重量平均分子量は、好ましくは１５０以上２９００以下、より好ましくは２５０以上１５００以下である。 The weight average molecular weight of the polymerizable compound (E) is preferably 150 or more and 2900 or less, more preferably 250 or more and 1500 or less.
　重合性化合物（Ｅ）の含有量は、着色硬化性樹脂組成物の固形分の総量１００質量部中、好ましくは７質量部以上６５質量部以下であり、より好ましくは１３質量部以上６０質量部以下であり、さらに好ましくは１５質量部以上５５質量部以下である。 The content of the polymerizable compound (E) is preferably 7 parts by weight or more and 65 parts by weight or less, more preferably 13 parts by weight or more and 60 parts by weight or less, in a total amount of 100 parts by weight of the solid content of the colored curable resin composition. Or less, more preferably 15 parts by mass or more and 55 parts by mass or less.
　〔４〕重合開始剤（Ｆ）
　重合開始剤（Ｆ）は、光や熱の作用により活性ラジカル、酸等を発生し、重合を開始し得る化合物であれば特に限定されることなく、公知の重合開始剤を用いることができる。活性ラジカルを発生する重合開始剤としては、例えば、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、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、２－メチル－２－モルホリノ－１－（４－メチルスルファニルフェニル）プロパン－１－オン、２－ジメチルアミノ－１－（４－モルホリノフェニル）－２－ベンジルブタン－１－オン、１－ヒドロキシシクロヘキシルフェニルケトン、２，４－ビス（トリクロロメチル）－６－ピペロニル－１，３，５－トリアジン、２，４，６－トリメチルベンゾイルジフェニルホスフィンオキサイド、２，２’－ビス（２－クロロフェニル）－４，４’，５，５’－テトラフェニルビイミダゾール等が挙げられる。 [4] Polymerization initiator (F)
The polymerization initiator (F) is not particularly limited as long as it is a compound capable of generating an active radical, an acid or the like by the action of light or heat and starting polymerization, and a known polymerization initiator can be used. Examples of polymerization initiators that generate active radicals include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) ) Octane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine, 2-methyl-2-morpholino-1- ( 4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,4-bis (trichloromethyl) ) -6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoy Diphenyl phosphine oxide, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole.
　重合開始剤（Ｆ）の含有量は、樹脂（Ｄ）及び重合性化合物（Ｅ）の合計量１００質量部に対して、好ましくは０．１質量部以上３０質量部以下であり、より好ましくは１質量部以上２０質量部以下である。重合開始剤（Ｆ）の含有量が、上記の範囲内にあると、高感度化して露光時間が短縮される傾向があるためカラーフィルタの生産性が向上する。 The content of the polymerization initiator (F) is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 100 parts by mass of the total amount of the resin (D) and the polymerizable compound (E). 1 to 20 parts by mass. When the content of the polymerization initiator (F) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, so the productivity of the color filter is improved.
　〔５〕重合開始助剤（Ｆ１）
　重合開始助剤（Ｆ１）は、重合開始剤（Ｆ）によって重合が開始された重合性化合物（Ｅ）の重合を促進するために用いられる化合物、もしくは増感剤である。重合開始助剤（Ｆ１）を含む場合、通常、重合開始剤（Ｆ）と組み合わせて用いられる。
　重合開始助剤（Ｆ１）としては、４，４’－ビス（ジメチルアミノ）ベンゾフェノン（通称ミヒラーズケトン）、４，４’－ビス（ジエチルアミノ）ベンゾフェノン、９，１０－ジメトキシアントラセン、２，４－ジエチルチオキサントン、Ｎ－フェニルグリシン等が挙げられる。 [5] Polymerization initiation assistant (F1)
The polymerization initiation assistant (F1) is a compound or a sensitizer used for accelerating the polymerization of the polymerizable compound (E) that has been polymerized by the polymerization initiator (F). When the polymerization initiation assistant (F1) is contained, it is usually used in combination with the polymerization initiator (F).
As polymerization initiation assistant (F1), 4,4′-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4′-bis (diethylamino) benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone N-phenylglycine and the like.
　重合開始助剤（Ｆ１）を用いる場合、その含有量は、樹脂（Ｄ）及び重合性化合物（Ｆ）の合計量１００質量部に対して、好ましくは０．１～３０質量部、より好ましくは１～２０質量部である。重合開始助剤（Ｆ１）の量がこの範囲内にあると、さらに高感度で着色パターンを形成することができ、カラーフィルタの生産性が向上する傾向にある。 When the polymerization initiation assistant (F1) is used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 100 parts by mass of the total amount of the resin (D) and the polymerizable compound (F). 1 to 20 parts by mass. When the amount of the polymerization initiation assistant (F1) is within this range, a colored pattern can be formed with higher sensitivity and the productivity of the color filter tends to be improved.
　〔６〕溶剤（Ｇ）
　溶剤（Ｇ）は、特に限定されず、当該分野で通常使用される溶剤を用いることができる。例えば、エステル溶剤（分子内に－ＣＯＯ－を含み、－Ｏ－を含まない溶剤）、エーテル溶剤（分子内に－Ｏ－を含み、－ＣＯＯ－を含まない溶剤）、エーテルエステル溶剤（分子内に－ＣＯＯ－と－Ｏ－とを含む溶剤）、ケトン溶剤（分子内に－ＣＯ－を含み、－ＣＯＯ－を含まない溶剤）、アルコール溶剤（分子内にＯＨを含み、－Ｏ－、－ＣＯ－及び－ＣＯＯ－を含まない溶剤）、芳香族炭化水素溶剤、アミド溶剤、ジメチルスルホキシド等が挙げられる。 [6] Solvent (G)
A solvent (G) is not specifically limited, The solvent normally used in the said field | area can be used. For example, ester solvents (solvents containing —COO— in the molecule and not containing —O—), ether solvents (solvents containing —O— in the molecule and not containing —COO—), ether ester solvents (intramolecular Solvent containing -COO- and -O-), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (containing OH in the molecule, -O-,- Solvent containing no CO- and -COO-), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide and the like.
　溶剤（Ｇ）としては、
　乳酸エチル、乳酸ブチル、２－ヒドロキシイソブタン酸メチル、酢酸ｎ－ブチル、酪酸エチル、酪酸ブチル、ピルビン酸エチル、アセト酢酸メチル、シクロヘキサノールアセテート及びγ－ブチロラクトン等のエステル溶剤（分子内に－ＣＯＯ－を含み、－Ｏ－を含まない溶剤）；
　エチレングリコールモノブチルエーテル、ジエチレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテル、３－メトキシ－１－ブタノール、ジエチレングリコールジメチルエーテル、ジエチレングリコールメチルエチルエーテル等のエーテル溶剤（分子内に－Ｏ－を含み、－ＣＯＯ－を含まない溶剤）；
　３－メトキシプロピオン酸メチル、３－エトキシプロピオン酸エチル、３－メトキシブチルアセテート、プロピレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート等のエーテルエステル溶剤（分子内に－ＣＯＯ－と－Ｏ－とを含む溶剤）；
　４－ヒドロキシ－４－メチル－２－ペンタノン、ヘプタノン、４－メチル－２－ペンタノン、シクロヘキサノン等のケトン溶剤（分子内に－ＣＯ－を含み、－ＣＯＯ－を含まない溶剤）；
　ブタノール、シクロヘキサノール、プロピレングリコール等のアルコール溶剤（分子内にＯＨを含み、－Ｏ－、－ＣＯ－及び－ＣＯＯ－を含まない溶剤）；
　Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド及びＮ－メチルピロリドン等のアミド溶剤；等が挙げられる。
　溶剤（Ｇ）としては、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテル、乳酸エチル、３－エトキシプロピオン酸エチル及び４－ヒドロキシ－４－メチル－２－ペンタノンがより好ましい。 As the solvent (G),
Ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate and γ-butyrolactone (within the molecule -COO- Containing -O--free solvent);
Ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether (solvents containing —O— in the molecule and not —COO—) );
Ether ester solvents such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate (with -COO- in the molecule) And a solvent containing -O-);
Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone, cyclohexanone (solvents containing —CO— in the molecule and not —COO—);
Alcohol solvents such as butanol, cyclohexanol, propylene glycol, etc. (solvents containing OH in the molecule but not -O-, -CO- and -COO-);
And amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone;
As the solvent (G), propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate and 4-hydroxy-4-methyl-2-pentanone are more preferable.
　溶剤（Ｇ）を含む場合、溶剤（Ｇ）の含有量は、着色硬化性樹脂組成物の総量１００質量部中、好ましくは７０質量部以上９５質量部以下であり、より好ましくは７５質量部以上９２質量部以下である。言い換えると、着色硬化性樹脂組成物の固形分の総量は、着色硬化性樹脂組成物の総量１００質量部中、好ましくは５質量部以上３０質量部以下、より好ましくは８質量部以上２５質量部以下である。
　溶剤（Ｇ）の含有量が上記の範囲内にあると、塗布時の平坦性が良好になり、またカラーフィルタを形成した際に色濃度が不足しないために表示特性が良好となる傾向がある。 When the solvent (G) is contained, the content of the solvent (G) is preferably 70 parts by mass or more and 95 parts by mass or less, more preferably 75 parts by mass or more, in a total amount of 100 parts by mass of the colored curable resin composition. 92 parts by mass or less. In other words, the total amount of the solid content of the colored curable resin composition is preferably 5 parts by mass or more and 30 parts by mass or less, more preferably 8 parts by mass or more and 25 parts by mass in the total amount of the colored curable resin composition of 100 parts by mass. It is as follows.
When the content of the solvent (G) is within the above range, the flatness at the time of coating is good, and when the color filter is formed, the color density does not become insufficient and the display characteristics tend to be good. .
　〔７〕レベリング剤（Ｈ）
　レベリング剤（Ｈ）としては、シリコーン系界面活性剤、フッ素系界面活性剤及びフッ素原子を有するシリコーン系界面活性剤等が挙げられる。これらは、側鎖に重合性基を有していてもよい。
　シリコーン系界面活性剤としては、分子内にシロキサン結合を有する界面活性剤等が挙げられる。具体的には、トーレシリコーンＤＣ３ＰＡ、同ＳＨ７ＰＡ、同ＤＣ１１ＰＡ、同ＳＨ２１ＰＡ、同ＳＨ２８ＰＡ、同ＳＨ２９ＰＡ、同ＳＨ３０ＰＡ、同ＳＨ８４００（商品名：東レ・ダウコーニング（株）製）、ＫＰ３２１、ＫＰ３２２、ＫＰ３２３、ＫＰ３２４、ＫＰ３２６、ＫＰ３４０、ＫＰ３４１（信越化学工業（株）製）、ＴＳＦ４００、ＴＳＦ４０１、ＴＳＦ４１０、ＴＳＦ４３００、ＴＳＦ４４４０、ＴＳＦ４４４５、ＴＳＦ４４４６、ＴＳＦ４４５２及びＴＳＦ４４６０（モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社製）等が挙げられる。 [7] Leveling agent (H)
Examples of the leveling agent (H) include silicone surfactants, fluorine surfactants, and silicone surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
Examples of the silicone surfactant include a surfactant having a siloxane bond in the molecule. Specifically, Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade names: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (made by Momentive Performance Materials Japan GK) .
　フッ素系界面活性剤としては、分子内にフルオロカーボン鎖を有する界面活性剤等が挙げられる。具体的には、フロラード（登録商標）ＦＣ４３０、同ＦＣ４３１（住友スリーエム（株）製）、メガファック（登録商標）Ｆ１４２Ｄ、同Ｆ１７１、同Ｆ１７２、同Ｆ１７３、同Ｆ１７７、同Ｆ１８３、同Ｆ５５４、同Ｒ３０、同ＲＳ－７１８－Ｋ（ＤＩＣ（株）製）、エフトップ（登録商標）ＥＦ３０１、同ＥＦ３０３、同ＥＦ３５１、同ＥＦ３５２（三菱マテリアル電子化成（株）製）、サーフロン（登録商標）Ｓ３８１、同Ｓ３８２、同ＳＣ１０１、同ＳＣ１０５（旭硝子（株）製）及びＥ５８４４（（株）ダイキンファインケミカル研究所製）等が挙げられる。 Examples of the fluorosurfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), MegaFac (registered trademark) F142D, F171, F172, F173, F177, F183, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), EFTOP (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals), Surflon (registered trademark) S381, S382, SC101, SC105 (Asahi Glass Co., Ltd.) and E5844 (Daikin Fine Chemical Laboratory Co., Ltd.).
　フッ素原子を有するシリコーン系界面活性剤としては、分子内にシロキサン結合及びフルオロカーボン鎖を有する界面活性剤等が挙げられる。具体的には、メガファック（登録商標）Ｒ０８、同ＢＬ２０、同Ｆ４７５、同Ｆ４７７及び同Ｆ４４３（ＤＩＣ（株）製）等が挙げられる。 Examples of the silicone surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, Megafac (registered trademark) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation), and the like can be given.
　レベリング剤（Ｈ）を含む場合、レベリング剤（Ｆ）の含有量は、着色硬化性樹脂組成物の総量１００質量部中、好ましくは０．００１質量部以上０．２質量部以下であり、より好ましくは０．００２質量部以上０．１質量部以下である。なお、この含有量に、分散剤の含有量は含まれない。レベリング剤（Ｈ）の含有量が上記の範囲内にあると、カラーフィルタの平坦性を良好にすることができる。 When the leveling agent (H) is included, the content of the leveling agent (F) is preferably 1001 parts by mass or more and 0.2 parts by mass or less, more preferably in a total amount of 100 parts by mass of the colored curable resin composition. Preferably they are 0.002 mass part or more and 0.1 mass part or less. This content does not include the content of the dispersant. When the content of the leveling agent (H) is in the above range, the flatness of the color filter can be improved.
　〔８〕その他の成分
　着色硬化性樹脂組成物は、必要に応じて、充填剤、他の高分子化合物、密着促進剤、酸化防止剤、光安定剤、連鎖移動剤等、当該技術分野で公知の添加剤を含んでもよい。
　該添加剤は、上記着色剤分散液又は共分散物に含まれていてもよい。 [8] Other components The colored curable resin composition is known in the art as necessary, such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, etc. The additive may be included.
The additive may be contained in the colorant dispersion or co-dispersion.
　〔９〕着色硬化性樹脂組成物の製造方法
　着色硬化性樹脂組成物は、着色剤分散液及び樹脂（Ｄ）、並びに必要に応じて用いられる重合性化合物（Ｅ）、重合開始剤（Ｆ）、溶剤（Ｇ）、重合開始助剤（Ｆ１）、レベリング剤（Ｈ）及びその他の成分を混合することにより調製できる。 [9] Method for producing colored curable resin composition The colored curable resin composition comprises a colorant dispersion, a resin (D), and a polymerizable compound (E) and a polymerization initiator (F) used as necessary. , Solvent (G), polymerization initiation assistant (F1), leveling agent (H) and other components can be mixed.
　＜カラーフィルタの製造方法＞
　着色剤分散液又は着色硬化性樹脂組成物から着色パターンを製造する方法としては、フォトリソグラフ法、インクジェット法、印刷法等が挙げられる。中でも、フォトリソグラフ法が好ましい。 <Color filter manufacturing method>
Examples of the method for producing a colored pattern from the colorant dispersion or the colored curable resin composition include a photolithographic method, an ink jet method, and a printing method. Of these, the photolithographic method is preferable.
　着色剤分散液又は着色硬化性樹脂組成物が、上記共分散物を含むことにより、コントラストに優れたカラーフィルタを作製することができる。該カラーフィルタは、表示装置（例えば、液晶表示装置、有機ＥＬ装置、電子ペーパー等）及び固体撮像素子に用いられるカラーフィルタとして有用である。 When the colorant dispersion or the colored curable resin composition contains the above-mentioned co-dispersion, a color filter having excellent contrast can be produced. The color filter is useful as a color filter used in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors.
　以下、実施例によって本発明について、より詳細に説明する。例中の「％」及び「部」は、特記ない限り、質量％及び質量部である。 Hereinafter, the present invention will be described in more detail by way of examples. Unless otherwise specified, “%” and “part” in the examples are mass% and part by mass.
　＜合成例１：化合物（Ｉ）の調製＞
　フタロニトリル（東京化成工業（株）製）３部とメタノール３００部を混合した。得られた混合物の温度を５℃以下に保ちながら、２８％ナトリウムメトキシドメタノール溶液（和光純薬工業（株）製）２．７１部を、３０分かけて滴下し、５℃で６時間撹拌した。得られた混合物の温度を５℃以下に保ちながら、酢酸１４部を加えた。得られた混合物に、４－（２－シアノアセチル）安息香酸（ＵＳ２６８０７３１に記載の方法に準じて合成）１４部を加え、４５℃で２６時間撹拌した。得られた混合物をろ過し、残渣を水３００部、メタノール３００部、Ｎ，Ｎ－ジメチルホルムアミド１５部の順で洗浄した。得られた残渣を６０℃で減圧乾燥して、下記式で表される化合物（Ｉ）を１０部得た（収率８３％）。 <Synthesis Example 1: Preparation of Compound (I)>
3 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 300 parts of methanol were mixed. While maintaining the temperature of the obtained mixture at 5 ° C. or lower, 2.71 parts of 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise over 30 minutes and stirred at 5 ° C. for 6 hours. did. While maintaining the temperature of the obtained mixture at 5 ° C. or lower, 14 parts of acetic acid was added. To the obtained mixture, 14 parts of 4- (2-cyanoacetyl) benzoic acid (synthesized according to the method described in US2680731) 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 10 parts of compound (I) represented by the following formula (yield 83%).
Figure JPOXMLDOC01-appb-I000046
Figure JPOXMLDOC01-appb-I000046
　［化合物（Ｉ）の同定］
（質量分析）イオン化モード＝ＥＳＩ＋：　ｍ／ｚ＝[Ｍ＋Ｈ]＋　４９０
　　　　　　　　　　　　　　Ｅｘａｃｔ　Ｍａｓｓ：　４８９ [Identification of Compound (I)]
(Mass spectrometry) ionization mode = ESI +: m / z = [M + H] + 490
Exact Mass: 489
　＜合成例２：化合物（ＩＩ）の調製＞
　フタロニトリル（東京化成工業（株）製）７．０２部とメタノール６１．６部を混合した。得られた混合物の温度を２℃に保ちながら、２８％ナトリウムメトキシドメタノール溶液（和光純薬工業（株）製）８．２０部とメタノール７４．６部との混合物を、１時間３０分かけて滴下した。得られた混合物を、２℃で６時間１５分撹拌した。得られた混合物の温度を４℃以下に保ちながら、酢酸１０．７部を加えた。得られた混合物に、ベンゾイルアセトニトリル（東京化成工業（株）製）１７．６部を加え、室温で４４時間撹拌した。得られた混合物をろ過し、残渣をメタノール８００部で洗浄した。得られた残渣を６０℃で減圧乾燥して、下記式で表される化合物（ＩＩａ）を１８．０部得た。 <Synthesis Example 2: Preparation of Compound (II)>
7.02 parts of phthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) and 61.6 parts of methanol were mixed. While maintaining the temperature of the obtained mixture at 2 ° C., a mixture of 8.20 parts of 28% sodium methoxide methanol solution (manufactured by Wako Pure Chemical Industries, Ltd.) and 74.6 parts of methanol was taken over 1 hour 30 minutes. And dripped. The resulting mixture was stirred at 2 ° C. for 6 hours and 15 minutes. While maintaining the temperature of the resulting mixture at 4 ° C. or lower, 10.7 parts of acetic acid was added. 17.6 parts of benzoylacetonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the resulting mixture and stirred at room temperature for 44 hours. The resulting mixture was filtered and the residue was washed with 800 parts of methanol. The obtained residue was dried at 60 ° C. under reduced pressure to obtain 18.0 parts of compound (IIa) represented by the following formula.
Figure JPOXMLDOC01-appb-I000047
Figure JPOXMLDOC01-appb-I000047
　［化合物（ＩＩａ）の同定］
（質量分析）イオン化モード＝ＥＳＩ＋：　ｍ／ｚ＝[Ｍ＋Ｈ]＋　４０２
　　　　　　　　　　　　　　Ｅｘａｃｔ　Ｍａｓｓ：　４０１ [Identification of Compound (IIa)]
(Mass spectrometry) Ionization mode = ESI +: m / z = [M + H] + 402
Exact Mass: 401
　次に、３℃の発煙硫酸（２５％）（和光純薬工業（株）製）７．６部を撹拌しながら、上で得られた化合物（ＩＩａ）０．５１３部を加えた。得られた混合物に発煙硫酸（２５％）（和光純薬工業（株）製）３．８部を加えた。得られた混合物を撹拌しながら、３時間３０分かけて１５℃まで上げた。得られた混合物に氷水１３９部を加え、さらに塩化ナトリウム３８．２部を加えた。得られた混合物をろ過し、得られた残渣を２１．５％塩化ナトリウム水溶液６４部で洗浄した。得られた残渣を６０℃で減圧乾燥して、下記式で表される化合物（ＩＩ）（化合物（ＩＩａ）に２個のスルホ基が結合された化合物）１．０２部を得た。 Next, 0.513 parts of the compound (IIa) obtained above was added while stirring 7.6 parts of fuming sulfuric acid (25%) (manufactured by Wako Pure Chemical Industries, Ltd.) at 3 ° C. Fuming sulfuric acid (25%) (manufactured by Wako Pure Chemical Industries, Ltd.) 3.8 parts was added to the obtained mixture. The resulting mixture was raised to 15 ° C. over 3 hours 30 minutes with stirring. 139 parts of ice water was added to the resulting mixture, and 38.2 parts of sodium chloride was further added. The resulting mixture was filtered, and the resulting residue was washed with 64 parts of a 21.5% aqueous sodium chloride solution. The obtained residue was dried at 60 ° C. under reduced pressure to obtain 1.02 parts of compound (II) represented by the following formula (compound in which two sulfo groups were bonded to compound (IIa)).
Figure JPOXMLDOC01-appb-I000048
Figure JPOXMLDOC01-appb-I000048
　［化合物（ＩＩ）の同定］
（質量分析）イオン化モード＝ＥＳＩ－：　ｍ／ｚ＝[Ｍ－Ｈ]－　５６０
　　　　　　　　　　　　　　Ｅｘａｃｔ　Ｍａｓｓ：　５６１ [Identification of Compound (II)]
(Mass spectrometry) Ionization mode = ESI−: m / z = [MH] − 560
Exact Mass: 561
　＜合成例３：樹脂（Ｄ）の調製＞
　還流冷却器、滴下ロート及び攪拌機を備えたフラスコ内に窒素を適量流して窒素雰囲気とし、プロピレングリコールモノメチルエーテルアセテート２８０部を入れ、攪拌しながら８０℃まで加熱した。次いで、該フラスコ内に、アクリル酸３８部、３，４－エポキシトリシクロ［５．２．１．０２，６］デカン－８－イルアクリレート及び３，４－エポキシトリシクロ［５．２．１．０２，６］デカン－９－イルアクリレートの混合物（含有率は１：１）２８９部をプロピレングリコールモノメチルエーテルアセテート１２５部に溶解した溶液を滴下ポンプを用いて約５時間かけて滴下した。一方、重合開始剤２，２－アゾビス（２，４－ジメチルバレロニトリル）３３部をプロピレングリコールモノメチルエーテルアセテート２３５部に溶解した溶液を別の滴下ポンプを用いて約６時間かけてフラスコ内に滴下した。滴下終了後、４時間同温度で保持した後、室温まで冷却して、固形分３５．１％の共重合体（樹脂（Ｄ））溶液を得た。生成した共重合体の重量平均分子量Ｍｗは９２００、分散度は２．０８、固形分換算の酸価は７７ｍｇ－ＫＯＨ／ｇであった。樹脂（Ｄ）は下記構造単位を有する。 <Synthesis Example 3: Preparation of Resin (D)>
An appropriate amount of nitrogen was passed through a flask equipped with a reflux condenser, a dropping funnel and a stirrer to create a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80 ° C. with stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 2,6 ] decan-8-yl acrylate and 3,4-epoxytricyclo [5.2. A solution of 289 parts of a mixture of 1.0 2,6 ] decan-9-yl acrylate (content is 1: 1) in 125 parts of propylene glycol monomethyl ether acetate was added dropwise over about 5 hours using a dropping pump. . Meanwhile, a solution prepared by dissolving 33 parts of polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was dropped into the flask over another 6 hours using another dropping pump. did. After completion of the dropwise addition, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (D)) solution having a solid content of 35.1%. The resulting copolymer had a weight average molecular weight Mw of 9,200, a dispersity of 2.08, and an acid value in terms of solid content of 77 mg-KOH / g. Resin (D) has the following structural units.
Figure JPOXMLDOC01-appb-I000049
Figure JPOXMLDOC01-appb-I000049
　樹脂の重量平均分子量（Ｍｗ）及び数平均分子量（Ｍｎ）の測定は、ＧＰＣ法を用いて、以下の条件で行った。
　装置；Ｋ２４７９（（株）島津製作所製）
　カラム；ＳＨＩＭＡＤＺＵ　Ｓｈｉｍ－ｐａｃｋ　ＧＰＣ－８０Ｍ
　カラム温度；４０℃
　溶媒；テトラヒドロフラン（ＴＨＦ）
　流速；１．０ｍＬ／ｍｉｎ
　検出器；ＲＩ
　校正用標準物質　；ＴＳＫ　ＳＴＡＮＤＡＲＤ　ＰＯＬＹＳＴＹＲＥＮＥ　Ｆ－４０、Ｆ－４、Ｆ－２８８、Ａ－２５００、Ａ－５００（東ソー（株）製） The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured using the GPC method under the following conditions.
Apparatus; K2479 (manufactured by Shimadzu Corporation)
Column; SHIMADZU Shim-pack GPC-80M
Column temperature: 40 ° C
Solvent; tetrahydrofuran (THF)
Flow rate: 1.0 mL / min
Detector; RI
Standard material for calibration: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
　上記で得られたポリスチレン換算の重量平均分子量（Ｍｗ）と数平均分子量（Ｍｎ）との比（Ｍｗ／Ｍｎ）を分散度とした。 The ratio (Mw / Mn) between the weight average molecular weight (Mw) in terms of polystyrene and the number average molecular weight (Mn) obtained above was defined as the dispersity.
　＜合成例４：脂肪族カルボン酸金属塩（Ｃ）分散液（分散液（Ｃ））の調製＞
　（脂肪族カルボン酸金属塩（Ｃ）の合成）
　ビーカーに１００部の純水及び５部の１２－ヒドロキシステアリン酸（東京化成工業（株）製）を混合した。この混合物に、７０℃で１％水酸化ナトリウム水溶液６５部を加えた。これを７０℃～７５℃を保ちながら、硝酸鉄（ＩＩＩ）九水和物（和光純薬工業（株）製）２部と水４０部の混合物を約２時間３０分かけて滴下した。この混合物を７０℃～７５℃に保ちながら約１時間撹拌した。この混合物を３５℃まで冷却し、ろ過した。
　得られた残渣を水２４５部で３回洗浄し、６０℃で減圧乾燥して、アニオン成分として１２－ヒドロキシステアリン酸アニオンを含むカルボン酸鉄（ＩＩＩ）塩（下記式（ｃ）で表される塩）を得た。以下、この塩を脂肪族カルボン酸金属塩（Ｃ）という。 <Synthesis Example 4: Preparation of Aliphatic Carboxylic Acid Metal Salt (C) Dispersion (Dispersion (C))>
(Synthesis of aliphatic carboxylic acid metal salt (C))
In a beaker, 100 parts of pure water and 5 parts of 12-hydroxystearic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed. To this mixture was added 65 parts of a 1% aqueous sodium hydroxide solution at 70 ° C. While maintaining this at 70 ° C. to 75 ° C., a mixture of 2 parts of iron (III) nitrate nonahydrate (manufactured by Wako Pure Chemical Industries, Ltd.) and 40 parts of water was added dropwise over about 2 hours 30 minutes. The mixture was stirred for about 1 hour while maintaining at 70 ° C to 75 ° C. The mixture was cooled to 35 ° C. and filtered.
The obtained residue was washed 3 times with 245 parts of water, dried under reduced pressure at 60 ° C., and an iron (III) carboxylate salt containing 12-hydroxystearate anion as an anion component (represented by the following formula (c)) Salt). Hereinafter, this salt is referred to as an aliphatic carboxylic acid metal salt (C).
Figure JPOXMLDOC01-appb-I000050
Figure JPOXMLDOC01-appb-I000050
　（分散液（Ｃ）の調製）
　脂肪族カルボン酸金属塩（Ｃ）　　　　　　　　２．５０部；
　分散剤１　　　　　　　　　　　　　　　　　　４．００部；
　溶剤（Ｇ）：ＰＧＭＥＡ　　　　　　　　　　　６８．５０部；及び
　溶剤（Ｇ）：ＤＡＡ　　　　　　　　　　　　　２５．００部；
を混合して、脂肪族カルボン酸金属塩（Ｃ）を分散させることにより、分散液（Ｃ）を得た。
　配合成分の詳細は次のとおりである。
　〔１〕脂肪族カルボン酸金属塩（Ｃ）：合成例４で得られた脂肪族カルボン酸金属塩（Ｃ）
　〔２〕分散剤１：分散剤（ＤＩＳＰＥＲＢＹＫ－１１１；ビックケミー・ジャパン（株）製）
　〔３〕ＰＧＭＥＡ：プロピレングリコールモノメチルエーテルアセテート
　〔４〕ＤＡＡ：ジアセトンアルコール（４－ヒドロキシ－４－メチル－２－ペンタノン） (Preparation of dispersion (C))
Aliphatic carboxylic acid metal salt (C) 2.50 parts;
Dispersant 1 4.00 parts;
Solvent (G): PGMEA 68.50 parts; and Solvent (G): DAA 25.00 parts;
Were mixed to disperse the aliphatic carboxylic acid metal salt (C) to obtain a dispersion (C).
The details of the ingredients are as follows.
[1] Aliphatic carboxylic acid metal salt (C): Aliphatic carboxylic acid metal salt (C) obtained in Synthesis Example 4
[2] Dispersant 1: Dispersant (DISPERBYK-111; manufactured by Big Chemie Japan Co., Ltd.)
[3] PGMEA: Propylene glycol monomethyl ether acetate [4] DAA: Diacetone alcohol (4-hydroxy-4-methyl-2-pentanone)
　＜実施例１～７、比較例１～５：着色剤分散液の調製＞
　表７に示す着色剤、分散剤２、合成例３で得られた樹脂（Ｄ）溶液、合成例４で得られた分散液（Ｃ）〔使用しない例あり〕、及び表７に示す溶剤（Ｇ）を混合し、ビーズミルを用いて、各着色剤分散液を得た。
　実施例１、実施例４、実施例６及び比較例２の着色剤分散液は、２種の着色剤の共分散物を含む。実施例２、実施例３、実施例５、実施例７、比較例３及び比較例４の着色剤分散液は、２種の着色剤の共分散物及び分散液（Ｃ）（脂肪族カルボン酸金属塩（Ｃ）分散液）を含む。
　各実施例、比較例で得られた着色剤分散液の組成を表７に示す。表７の数値の単位は、質量部である。表７における溶剤（Ｇ）には、樹脂（Ｄ）溶液中及び分散液（Ｃ）中の溶剤が含まれている。 <Examples 1 to 7, Comparative Examples 1 to 5: Preparation of colorant dispersion>
Colorant shown in Table 7, Dispersant 2, Resin (D) solution obtained in Synthesis Example 3, Dispersion liquid (C) obtained in Synthesis Example 4 [There are some examples not used], and Solvents shown in Table 7 ( G) was mixed, and each colorant dispersion was obtained using a bead mill.
The colorant dispersions of Example 1, Example 4, Example 6, and Comparative Example 2 contain a co-dispersion of two colorants. The colorant dispersions of Example 2, Example 3, Example 5, Example 7, Comparative Example 3 and Comparative Example 4 are co-dispersions of two colorants and dispersion (C) (aliphatic carboxylic acid). Metal salt (C) dispersion).
Table 7 shows the compositions of the colorant dispersions obtained in each Example and Comparative Example. The unit of numerical values in Table 7 is parts by mass. The solvent (G) in Table 7 contains the solvent in the resin (D) solution and the dispersion liquid (C).
Figure JPOXMLDOC01-appb-T000051
Figure JPOXMLDOC01-appb-T000051
　着色剤分散液に含まれる配合成分の詳細は次のとおりである。
　〔１〕Ｙ１３８：Ｃ．Ｉ．ピグメントイエロー１３８
　〔２〕Ｙ１８５：Ｃ．Ｉ．ピグメントイエロー１８５
　〔３〕化合物（Ｉ）：合成例１で得られた化合物（Ｉ）
　〔４〕化合物（ＩＩ）：合成例２で得られた化合物（ＩＩ）
　〔５〕脂肪族カルボン酸金属塩（Ｃ）：合成例４で得られた脂肪族カルボン酸金属塩（Ｃ）
　〔６〕分散剤２：分散剤（ＢＹＫ－ＬＰ　Ｎ　６９１９；ビックケミー・ジャパン（株）製）
　〔７〕樹脂（Ｄ）：合成例３で得られた樹脂（Ｄ）溶液中に含まれる樹脂（Ｄ）
　〔８〕ＰＧＭＥＡ：プロピレングリコールモノメチルエーテルアセテート
　〔９〕ＤＡＡ：ジアセトンアルコール（４－ヒドロキシ－４－メチル－２－ペンタノン） Details of the blending components contained in the colorant dispersion are as follows.
[1] Y138: C.I. I. Pigment Yellow 138
[2] Y185: C.I. I. Pigment Yellow 185
[3] Compound (I): Compound (I) obtained in Synthesis Example 1
[4] Compound (II): Compound (II) obtained in Synthesis Example 2
[5] Aliphatic carboxylic acid metal salt (C): Aliphatic carboxylic acid metal salt (C) obtained in Synthesis Example 4
[6] Dispersant 2: Dispersant (BYK-LP N 6919; manufactured by Big Chemie Japan Co., Ltd.)
[7] Resin (D): Resin (D) contained in the resin (D) solution obtained in Synthesis Example 3
[8] PGMEA: Propylene glycol monomethyl ether acetate [9] DAA: Diacetone alcohol (4-hydroxy-4-methyl-2-pentanone)
　＜実施例８～１６、比較例６～１０＞
　（１）着色硬化性樹脂組成物の調製
　実施例８～１４及び比較例６～１０においては、それぞれ実施例１～７、比較例１～５の着色剤分散液と、樹脂（Ｄ）溶液、重合性化合物（Ｅ）、重合開始剤（Ｆ）及びレベリング剤（Ｈ）とを混合して着色硬化性樹脂組成物を得た。
　実施例１５及び１６においては、実施例１の着色剤分散液と、合成例４で得られた分散液（Ｃ）と、樹脂（Ｄ）溶液、重合性化合物（Ｅ）、重合開始剤（Ｆ）及びレベリング剤（Ｈ）とを混合して着色硬化性樹脂組成物を得た。
　なお、着色硬化性樹脂組成物の調製にあたり、着色硬化性樹脂組成物の固形分が２０質量％となるように、プロピレングリコールモノメチルエーテルアセテート（ＰＧＭＥＡ）を添加した。
　各実施例、比較例で使用した着色剤分散液、及び、各実施例、比較例で得られた着色硬化性樹脂組成物における溶剤（Ｇ）を除く組成を表８及び表９に示す。表８及び表９における各成分の配合量の単位は、質量部である。 <Examples 8 to 16, Comparative Examples 6 to 10>
(1) Preparation of colored curable resin composition In Examples 8 to 14 and Comparative Examples 6 to 10, the colorant dispersions of Examples 1 to 7 and Comparative Examples 1 to 5, the resin (D) solution, A polymerizable compound (E), a polymerization initiator (F), and a leveling agent (H) were mixed to obtain a colored curable resin composition.
In Examples 15 and 16, the colorant dispersion of Example 1, the dispersion (C) obtained in Synthesis Example 4, the resin (D) solution, the polymerizable compound (E), and the polymerization initiator (F ) And a leveling agent (H) were mixed to obtain a colored curable resin composition.
In preparing the colored curable resin composition, propylene glycol monomethyl ether acetate (PGMEA) was added so that the solid content of the colored curable resin composition was 20% by mass.
Tables 8 and 9 show the compositions excluding the colorant dispersion used in each Example and Comparative Example and the solvent (G) in the colored curable resin composition obtained in each Example and Comparative Example. The unit of the blending amount of each component in Table 8 and Table 9 is part by mass.
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000053
　重合性化合物（Ｅ）、重合開始剤（Ｆ）及びレベリング剤（Ｈ）の詳細は次のとおりである。
　〔１〕重合性化合物（Ｅ）：ジペンタエリスリトールヘキサアクリレート（ＫＡＹＡＲＡＤ　ＤＰＨＡ；日本化薬（株）製）
　〔２〕重合開始剤（Ｆ）：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（イルガキュア（登録商標）ＯＸＥ－０１；ＢＡＳＦジャパン社製）
　〔３〕レベリング剤（Ｈ）：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） Details of the polymerizable compound (E), the polymerization initiator (F), and the leveling agent (H) are as follows.
[1] Polymerizable compound (E): dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
[2] Polymerization initiator (F): N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF Japan)
[3] Leveling agent (H): polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)
　（２）着色塗膜の作製
　５ｃｍ角のガラス基板（イーグル２０００；コーニング社製）上に、着色硬化性樹脂組成物をスピンコート法で塗布した後、１００℃で３分間プリベークして着色組成物層を形成した。放冷後、露光機（ＴＭＥ－１５０ＲＳＫ；トプコン（株）製）を用いて、大気雰囲気下、１５０ｍＪ／ｃｍ２の露光量（３６５ｎｍ基準）で光照射した。光照射後の着色組成物層を、非イオン系界面活性剤０．１２％と水酸化カリウム０．０４％を含む水系現像液に２４℃で１０秒間浸漬現像し、水洗後、オーブン中、２３０℃で３０分間ポストベークを行い、着色塗膜を得た。 (2) Preparation of colored coating film A colored curable resin composition was applied by spin coating on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning), and then pre-baked at 100 ° C for 3 minutes. A layer was formed. After allowing to cool, light exposure was performed using an exposure machine (TME-150RSK; manufactured by Topcon Corporation) at an exposure amount of 150 mJ / cm 2 (based on 365 nm) in an air atmosphere. The colored composition layer after light irradiation is immersed and developed in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 24 ° C. for 10 seconds, washed with water, Post-baking was carried out at 30 ° C. for 30 minutes to obtain a colored coating film.
　（３）膜厚測定
　上記（２）で得られた着色塗膜について、膜厚を、膜厚測定装置（ＤＥＫＴＡＫ３；日本真空技術（株）製））を用いて測定した。
　得られた着色塗膜の膜厚は、いずれの実施例及び比較例においても２．０μｍであった。 (3) Film thickness measurement About the colored coating film obtained by said (2), the film thickness was measured using the film thickness measuring apparatus (DEKTAK3; Nippon Vacuum Technology Co., Ltd. product).
The film thickness of the obtained colored coating film was 2.0 μm in all examples and comparative examples.
　（４）色度評価
　上記（２）で得られた着色塗膜について、測色機（ＯＳＰ－ＳＰ－２００；オリンパス（株）製）を用いて分光を測定し、Ｃ光源の特性関数を用いてＣＩＥのＸＹＺ表色系におけるｘｙ色度座標（ｘ、ｙ）を測定した。結果を表８及び表９に示す。 (4) Chromaticity evaluation The color coating film obtained in (2) above was measured for spectroscopy using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the characteristic function of the C light source was used. The xy chromaticity coordinates (x, y) in the CIE XYZ color system were measured. The results are shown in Table 8 and Table 9.
　（５）コントラスト評価
　上記（２）で得られた着色塗膜について、コントラスト計（ＣＴ－１；壺坂電機社製、色彩色差計ＢＭ－５Ａ；トプコン社製、光源；Ｆ－１０、偏光フィルム；壷坂電機（株）製）を用いて、ブランク値を３００００としてコントラストを測定した。結果を表８及び表９に示す。着色塗膜におけるコントラストが高ければ、着色パターンにおいても同様に高コントラストであるといえる。 (5) Contrast Evaluation Concerning the colored coating film obtained in the above (2), a contrast meter (CT-1; manufactured by Aisaka Electric Co., Ltd., color / color difference meter BM-5A; manufactured by Topcon Co., Ltd., light source; F-10, polarizing film) A contrast value was measured using a blank value of 30000. The results are shown in Table 8 and Table 9. If the contrast in the colored coating film is high, it can be said that the color pattern has the same high contrast.
　本発明によれば、コントラストの改善されたカラーフィルタ、及びそれを含む表示装置を提供することができる。 According to the present invention, it is possible to provide a color filter with improved contrast and a display device including the same.

Claims (8)

  1. 　主成分としてのＣ．Ｉ．ピグメントイエロー１３８（Ａ）と、式（Ｉ）で表される化合物（Ｂ）との共分散物を含む、着色剤分散液。
    Figure JPOXMLDOC01-appb-I000001
    ［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、０～１０のいずれかの整数である。
    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－ＮＲｎａ－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－からなる群より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－ＮＲｎａ－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－からなる群より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からなる群より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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
    　Ｒｎａ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－からなる群より選ばれる少なくとも一種を有していてもよい。Ｒｎａが複数個存在する場合、これらは同一でもよく、異なっていてもよい。
    　Ｍｂ＋は、ヒドロン又はｂ価の金属イオンを表す。Ｍｂ＋が複数個存在する場合、これらは同一でもよく、異なっていてもよい。Ｍｂ＋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、Ｍｂ＋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－ＮＲｎｂ－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－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－ＮＲｎｂ－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からなる群より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－ＮＲｎｂ－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－ＯＲｎｂ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎｂ１）、－ＣＯ－Ｎ（Ｒｎｂ１）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎｂ１又は－Ｓ（Ｏ）２－Ｒｎｂ１を表す。
    　ただし、Ｒ６が－ＣＯ－ＮＨ（Ｒｎｂ１）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－ＮＲｎｂ－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からなる群より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－ＮＲｎｂ－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－ＮＲｎｂ－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－ＮＲｎｂ－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。
    Figure JPOXMLDOC01-appb-I000002
    ［式（１ａ）中、
    　Ｒ１７ｂ及びＲ１８ｂ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－ＮＲｎｂ－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。
    　Ｒ１７ｂとＲ１８ｂ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－ＮＲｎｂ－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。］
    　Ｒｎｂ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。Ｒｎｂが複数個存在する場合、これらは同一でもよく、異なっていてもよい。
    　Ｒｎｂ１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－ＮＲｎｂ１０－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。Ｒｎｂ１が複数個存在する場合、これらは同一でもよく、異なっていてもよい。
    　Ｒｎｂ１０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。Ｒｎｂ１０が複数個存在する場合、これらは同一でもよく、異なっていてもよい。］     C. as a main component. I. A colorant dispersion containing a co-dispersion of CI Pigment Yellow 138 (A) and the compound (B) represented by the formula (I).
    Figure JPOXMLDOC01-appb-I000001
    [In the formula (I),
    a represents the total number of —CO 2 — and —S (O) 2 O — contained in the compound represented by the formula (I), and is an integer of 0 to 10.
    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 which may have a substituent or a hydrogen atom, and —CH contained in the hydrocarbon group 2 - the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO -, - S (O) 2 - or -NR na - to have replaced May be. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 each independently 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, cyano. group, a nitro group, -CO 2 - or -S (O) 2 O - represents, -CH 2 - contained in the hydrocarbon group when including - and said heterocyclic group is -CH 2 does not constitute a ring The —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 —, or —NR na —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 selected from the group consisting 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 combined with the carbon atom to which each is bonded. To form an optionally substituted ring, and when the ring contains —CH 2 — that does not form a ring, —CH 2 — represents —O—, —CO—, —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 a plurality of R na are present, these may be the same or different.
    M b + represents hydron or a b-valent metal ion. When a plurality of M b + are present, these may be the same or different. When M b + is hydrone, the hydrone is present 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 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 which may have a substituent or a hydrogen atom, and —CH contained in the hydrocarbon group 2 - the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO -, - S (O) 2 - or -NR nb - to have replaced May be. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
    R 2 to R 5 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
    At least one selected from the group consisting of R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may have a substituent together with the carbon atom to which each is bonded. A ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR nb — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
    R 6 represents —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 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
    (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 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR nb- may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. R 2 to R 5 which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, —O—, —CO—, —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
    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, -CH 2 - contained in the hydrocarbon group and -CH 2 where the heterocyclic group does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 -Or -NR nb- may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. R 7 may be combined with the carbon atom to which R 6 and R 7 are bonded to form a ring.
    X represents a group represented by the formula (1a).
    Figure JPOXMLDOC01-appb-I000002
    [In Formula (1a),
    R 17b and R 18b each independently represent 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR nb — may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
    R 17b and R 18b may form a ring optionally having a substituent together with the carbon atom to which each is bonded, and when the ring contains —CH 2 — that does not form a ring, The —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR nb —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
    * 1 represents a bond to the 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 two or more Rnb exists, these may be the same and may differ.
    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 —CH 2 — contained in the hydrocarbon group and it is, -O - - the -CH 2 when including - heterocyclic group -CH 2 that does not constitute a ring, - CO -, - S ( O) 2 - or -NR NB 10 - may be replaced by . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. When two or more Rnb1 exists, these may be the same and may differ.
    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 two or more Rnb10 exists, these may be the same and may differ. ]
  2. 　式（１ａ）で表される基が、式（２ａ）で表される基である、請求項１に記載の着色剤分散液。
    Figure JPOXMLDOC01-appb-I000003
    ［式（２ａ）中、
    　Ｒ１９ｂ及びＲ２０ｂ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－ＮＲｎｂ－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。
    　Ｒｎｂ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。］     The colorant dispersion according to claim 1, wherein the group represented by the formula (1a) is a group represented by the formula (2a).
    Figure JPOXMLDOC01-appb-I000003
    [In Formula (2a),
    R 19b and R 20b each independently represent 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, the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring - -CH 2 contained in the hydrogen group, -O -, - CO -, - S (O) 2 - or -NR nb- may be substituted . However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —.
    R nb represents the same meaning as described above.
    * 2 represents a bond to the isoindoline ring. ]
  3. 　式（Ｉ）中、
    ａ）ａが１～１０のいずれかの整数である場合、
    　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－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－ＮＲｎａ－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－からなる群より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、及び、Ｒ４とＲ５からなる群より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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
    　Ｒ６は、－ＣＯ－ＯＲｎａ１、－ＣＯ－ＮＨ２、－ＣＯ－ＮＨ（Ｒｎａ１）、－ＣＯ－Ｎ（Ｒｎａ１）２、－ＣＯ－Ｈ、－ＣＯ－Ｒｎａ１又は－Ｓ（Ｏ）２－Ｒｎａ１を表す。
    　ただし、Ｒ６が－ＣＯ－ＮＨ（Ｒｎａ１）を表す場合、Ｒ２～Ｒ５は、（ｉａ）及び（ｉｉａ）の少なくとも一方を充足する。
    　（ｉａ）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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
    　（ｉｉａ）Ｒ２とＲ３、Ｒ３とＲ４、及び、Ｒ４とＲ５からなる群より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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
    　Ｒ７は、シアノ基を表す。
    　Ｘは、式（１ａ－ｘ）で表される基を表す。
    Figure JPOXMLDOC01-appb-I000004
    ［式（１ａ－ｘ）中、
    　Ｒ２１及び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－ＮＲｎａ－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－からなる群より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、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－ＮＲｎａ－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－からなる群より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。］
    　Ｒｎａは、前記と同じ意味を表す。
    　Ｒｎａ１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－ＮＲｎａ１０－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。該炭化水素基及び該複素環基は、－ＣＯ２ －及び－Ｓ（Ｏ）２Ｏ－からなる群より選ばれる少なくとも一種を有していてもよい。Ｒｎａ１が複数個存在する場合、これらは同一でもよく、異なっていてもよい。
    　Ｒｎａ１０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、Ｒｎａ１０が複数個存在する場合、これらは同一でもよく、異なっていてもよい。
    ｂ）ａが０である場合、
    　Ｒ７は、シアノ基を表す、請求項１又は２に記載の着色剤分散液。     In formula (I),
    a) When a is an integer of 1 to 10,
    R 2 to R 5 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 selected from the group consisting of R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may have a substituent together with the carbon atom to which each is bonded. A ring may be formed, and when —CH 2 —, which does not form a ring, contains —CH 2 —, —O—, —CO—, —S (O) 2 — or —NR na — May be replaced. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. The ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
    R 6 represents —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 6 represents —CO—NH (R na1 ), R 2 to R 5 satisfy at least one of (ia) and (ia).
    (Ia) At least one of R 2 to R 5 may have a substituent, a hydrocarbon group having 1 to 40 carbon atoms, a heterocyclic group that may have a substituent, a halogen atom, a cyano group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO-, —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 — .
    (Iii) 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 has a substituent together with the carbon atom to which each is bonded. and forms a ring which may, -CH 2 that said ring does not constitute a ring - is, -O - - the -CH 2 when containing, - CO -, - S ( O) 2 - or -NR It may be replaced with na-. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. The ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — . R 2 to R 5 which do not form a ring are each independently 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, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, It may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 7 represents a cyano group.
    X represents a group represented by the formula (1a-x).
    Figure JPOXMLDOC01-appb-I000004
    [In the formula (1a-x),
    R 21 and R 22 are each independently 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, cyano. represents a group or a nitro group, -CH 2 - contained in the hydrocarbon group the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring, -O -, - CO- , —S (O) 2 — or —NR na — may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 together with the carbon atom to which each is bonded may form a ring that may have a substituent, and when the ring contains —CH 2 — that does not form a ring The —CH 2 — may be replaced by —O—, —CO—, —S (O) 2 — or —NR na —. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. The ring may have at least one selected from the group consisting of —CO 2 — and —S (O) 2 O — .
    * 1 represents a bond to the isoindoline ring. ]
    R na represents 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 —CH 2 — contained in the hydrocarbon group and it is, -O - - the -CH 2 when including - heterocyclic group -CH 2 that does not constitute a ring, - CO -, - S ( O) 2 - or -NR NA 10 - may be replaced by . However, —COOH and —S (O) 2 OH are not formed by replacing —CH 2 —. 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 a plurality of R na1 are present, these may be the same or different.
    R na10 represents an optionally substituted hydrocarbon group having 1 to 35 carbon atoms or an optionally substituted heterocyclic group, and when there are a plurality of Rna10 , these are the same. But it may be different.
    b) If a is 0,
    The colorant dispersion according to claim 1 or 2, wherein R 7 represents a cyano group.
  4. 　式（１ａ－ｘ）で表される基が、式（２ａ－ｘ）で表される基である、請求項３に記載の着色剤分散液。
    Figure JPOXMLDOC01-appb-I000005
    ［式（２ａ－ｘ）中、
    　Ｒ２３及び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－ＮＲｎａ－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－からなる群より選ばれる少なくとも一種を有していてもよい。
    　Ｒｎａ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。］     The colorant dispersion according to claim 3, wherein the group represented by the formula (1a-x) is a group represented by the formula (2a-x).
    Figure JPOXMLDOC01-appb-I000005
    [In the formula (2a-x)
    R 23 and R 24 each independently represent 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, the -CH 2 when including - - and heterocyclic group is -CH 2 does not constitute a ring - -CH 2 contained in the hydrogen group, -O -, - CO -, - S (O) 2 - or -NR na- may be substituted. However, —COOH or —S (O) 2 OH is not formed by replacing —CH 2 —. 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 represents the same meaning as described above.
    * 2 represents a bond to the isoindoline ring. ]
  5. 　ヒドロキシ基を有する炭素数１～４０の脂肪族カルボン酸のアニオンを有する金属塩（Ｃ）をさらに含む、請求項１～４のいずれか１項に記載の着色剤分散液。 The colorant dispersion according to any one of claims 1 to 4, further comprising a metal salt (C) having an anion of an aliphatic carboxylic acid having 1 to 40 carbon atoms having a hydroxy group.
  6. 　請求項１～５のいずれか１項に記載の着色剤分散液と、樹脂（Ｄ）とを含む、着色硬化性樹脂組成物。 A colored curable resin composition comprising the colorant dispersion according to any one of claims 1 to 5 and a resin (D).
  7. 　請求項１～５のいずれか１項に記載の着色剤分散液又は請求項６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。 A color filter formed from the colorant dispersion according to any one of claims 1 to 5 or the colored curable resin composition according to claim 6.
  8. 　請求項７に記載のカラーフィルタを含む、表示装置。 A display device comprising the color filter according to claim 7.
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