WO2019171999A1 - Dispersion liquide de colorant, composition de résine durcissable colorée, filtre coloré, et dispositif d'affichage - Google Patents

Dispersion liquide de colorant, composition de résine durcissable colorée, filtre coloré, et dispositif d'affichage 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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English (en)
Japanese (ja)
Inventor
学 栂井
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住友化学株式会社
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Priority to KR1020207028203A priority Critical patent/KR102637673B1/ko
Priority to CN201980016992.8A priority patent/CN111836859B/zh
Publication of WO2019171999A1 publication Critical patent/WO2019171999A1/fr

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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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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Optics & Photonics (AREA)
  • Theoretical Computer Science (AREA)
  • Structural Engineering (AREA)
  • Architecture (AREA)
  • Optical Filters (AREA)
  • Materials For Photolithography (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une dispersion liquide de colorant qui contient un C. I. Pigment Jaune 138, et qui permet de former un filtre coloré présentant un contraste satisfaisant. L'invention concerne également une composition de résine durcissable colorée contenant cette dispersion liquide de colorant, le filtre coloré formé à partir de cette dispersion liquide de colorant ou de cette composition de résine durcissable colorée, et un dispositif d'affichage contenant un filtre coloré. Ainsi, à l'aide de la dispersion liquide de colorant contenant en tant que principaux composants le C. I. Pigment Jaune 138 (A) et un composé (B) représenté par la formule (I), et de la composition de résine durcissable colorée contenant cette dispersion liquide de colorant, il est possible de fournir un filtre coloré présentant un contraste satisfaisant, et un dispositif d'affichage contenant celui-ci.
PCT/JP2019/006984 2018-03-06 2019-02-25 Dispersion liquide de colorant, composition de résine durcissable colorée, filtre coloré, et dispositif d'affichage WO2019171999A1 (fr)

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CN201980016992.8A CN111836859B (zh) 2018-03-06 2019-02-25 着色剂分散液、着色固化性树脂组合物、滤色器和显示装置

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JP2017137490A (ja) * 2016-02-01 2017-08-10 住友化学株式会社 化合物及び着色組成物
JP2018012834A (ja) * 2016-07-07 2018-01-25 住友化学株式会社 顔料組成物、着色組成物及び着色硬化性組成物
KR20180014306A (ko) * 2016-07-28 2018-02-08 엘지디스플레이 주식회사 착색제, 이를 포함하는 착색 수지 조성물 및 컬러필터

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JP5334624B2 (ja) * 2008-03-17 2013-11-06 富士フイルム株式会社 着色硬化性組成物、カラーフィルタ、及びカラーフィルタの製造方法
JP5728336B2 (ja) 2011-08-31 2015-06-03 富士フイルム株式会社 カラーフィルタの製造方法、及び固体撮像素子の製造方法
KR102092910B1 (ko) * 2015-06-30 2020-03-24 동우 화인켐 주식회사 착색 경화성 수지 조성물, 컬러 필터 및 표시 장치
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KR102378450B1 (ko) * 2016-03-31 2022-03-23 스미또모 가가꾸 가부시끼가이샤 착색 경화성 수지 조성물

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JP2012236882A (ja) * 2011-05-10 2012-12-06 Dainippon Printing Co Ltd 黄色顔料分散液、カラーフィルタ用黄色感光性樹脂組成物、カラーフィルタ、液晶表示装置及び有機発光表示装置
JP2017137490A (ja) * 2016-02-01 2017-08-10 住友化学株式会社 化合物及び着色組成物
JP2018012834A (ja) * 2016-07-07 2018-01-25 住友化学株式会社 顔料組成物、着色組成物及び着色硬化性組成物
KR20180014306A (ko) * 2016-07-28 2018-02-08 엘지디스플레이 주식회사 착색제, 이를 포함하는 착색 수지 조성물 및 컬러필터

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KR20200130344A (ko) 2020-11-18
JP7241566B2 (ja) 2023-03-17
TWI790354B (zh) 2023-01-21
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