CN113376963A - Coloring composition and compound - Google Patents

Coloring composition and compound Download PDF

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CN113376963A
CN113376963A CN202110682591.5A CN202110682591A CN113376963A CN 113376963 A CN113376963 A CN 113376963A CN 202110682591 A CN202110682591 A CN 202110682591A CN 113376963 A CN113376963 A CN 113376963A
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carbon atoms
substituent
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compound
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织田胜成
栂井学
滨木裕史
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Sumitomo Chemical Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00Other synthetic dyes of known constitution
    • C09B57/04Isoindoline dyes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44Iso-indoles; Hydrogenated iso-indoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/004Mixtures of two or more reactive dyes
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/20Filters
    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1335Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509Filters, e.g. light shielding masks
    • G02F1/133514Colour filters
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007Filters, e.g. additive colour filters; Components for display devices
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds

Abstract

The present invention relates to a coloring composition and a compound. The present invention provides a coloring composition comprising: a compound represented by formula (IZ3), and an alkali-soluble resin.

Description

Coloring composition and compound
The present application is a divisional application of an invention application having an application date of 2017, 8/31/2017, an application number of 201710776175.5, and an invention name of "coloring composition and compound".
Technical Field
The present invention relates to a coloring composition and a compound.
Background
The colored curable composition has been used for producing a color filter (color filter) that can be used in a display device such as a liquid crystal display device or an electroluminescence display device. As a colorant contained in this colored curable composition, c.i. pigment yellow 185 is known (japanese patent laid-open No. 2016-66020).
Figure BDA0003121580680000011
Disclosure of Invention
The present invention includes the following inventions.
[1] A coloring composition comprising:
at least one selected from the group consisting of a compound represented by the formula (IZ1), a compound represented by the formula (IZ2), a compound represented by the formula (IZ3), a compound represented by the formula (IZ4), a compound represented by the formula (IZ5) and a compound represented by the formula (IZ6), and
at least one of a resin and a solvent.
Figure BDA0003121580680000012
[ formula (IZ1), R O1Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1Each of which may be bonded to each other to form a ring.
R101Z1The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
R102Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents a hydrogen atom or an alkali metal atom.
R101Z1、R102Z1And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
Figure BDA0003121580680000021
[ formula (IZ2), RCO1Z2And RCO2Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2。RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2And R5Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2Each of which may be bonded to each other to form a ring.
R101Z2The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R O1Z2And R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
Figure BDA0003121580680000031
[ formula (IZ3), R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3Each of which may be bonded to each other to form a ring. R101Z3The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z3Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z3、R102Z3And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
Figure BDA0003121580680000032
[ formula (IZ4), RN1Z4And RN2Z4Independently of one another represent-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4And R7Z4Independently of one another, represents a hydrogen atom, -CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4Each of which may be bonded to each other to form a ring. R101Z4The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z4Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z4、R102Z4And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
Figure BDA0003121580680000041
[ formula (IZ5), RN1Z5represents-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M, optionally substituted carbon atomA hydrocarbon group or a heterocyclic group which may have a substituent, wherein the number of the hydrocarbon groups is 1 to 40.
R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5And R7Z5Independently of one another, represents a hydrogen atom, -CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Each of which may be bonded to each other to form a ring, R2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R 102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5At least one group of them is bonded to form a ring.
R101Z5The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
R102Z5Represents a hydrogen atom, may haveThe substituent is a hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
R101Z5、R102Z5And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
Figure BDA0003121580680000051
Figure BDA0003121580680000052
Figure BDA0003121580680000053
[ in the formula (IZ6), D represents a structure having an isoindoline skeleton. Z represents-SO3 -or-CO2 -。Ac+Represents a metal cation having a valence of c. a represents an integer of 1 to 10.
b represents an integer of 1 or more. c represents an integer of 2 to 10. d represents an integer of 1 or more. D. Z, a or Ac+When there are a plurality of them, they may be the same or different. The formula (I 'Z6) and the formula (I' Z6) respectively represent partial structures of the formula (IZ6), D, Z, Ac+A, b, c and d represent the same meanings as the corresponding symbols in formula (IZ 6).
The partial structure represented by the formula (I' Z6) has the same negative valence as the partial structure represented by the formula (I "Z6) has the same positive valence in absolute value. ]
[2] A colored curable composition comprising a polymerizable compound and the colored composition according to [1 ].
[3] A color filter comprising the colored composition according to [1] or the colored curable composition according to [2] or [11 ].
[4] A liquid crystal display device comprising the color filter according to [3 ].
[5] A compound represented by the formula (Z1-B).
Figure BDA0003121580680000061
[ formula (IZ1-B) wherein RO11Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
R1Z1、R21Z1、R31Z1、R41Z1、R51Z1、R61Z1And R71Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R21Z1And R31Z1、R31Z1And R41Z1And R41Z1And R51Z1Each of which may be bonded to each other to form a ring. Wherein R is21Z1、R31Z1、R41Z1And R51Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a C1-40 hydrocarbon group which may have a substituent or may have a substituentA heterocyclic radical of a substituent, or, R21Z1And R31Z1、R31Z1And R41Z1And R41Z1And R51Z1At least one group of them is bonded to form a ring. R101Z1The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
R102Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom.
R101Z1、R102Z1And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[6] A compound represented by the formula (IZ 2-B).
Figure BDA0003121580680000071
[ formula (IZ2-B) wherein RCO11Z2And RCO21Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2,RCO11Z2And RCO21Z2At least one of which is-NRN1Z2RN2Z2
RN1Z2、RN2Z2、R1Z2、R21Z2、R31Z2、R41Z2And R51Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2Each of which may be bonded to each other to form a ring, R21Z2、R31Z2、R41Z2And R51Z2At least one of which is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2At least one group of them is bonded to form a ring.
R101Z2The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
RO1Z2And R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents a hydrogen atom or an alkali metal atom.
RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[7] A compound represented by the formula (IZ 3-B).
Figure BDA0003121580680000081
[ formula (IZ3-B) wherein R1Z3、R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Independently of one another represent hydrogen atomSon, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3Each of which may be bonded to each other to form a ring.
Wherein R is21Z3、R31Z3、R41Z3And R51Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3At least one group of them is bonded to form a ring. R101Z3The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z3Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom.
R101Z3、R102Z3And in the case where there are a plurality of M,they may be the same or different. The wavy line indicates the E-body or the Z-body. ]
[8] A compound represented by the formula (IZ 4).
Figure BDA0003121580680000091
[ formula (IZ4), RN1Z4And RN2Z4Independently of one another represent-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4And R7Z4Independently of one another, represents a hydrogen atom, -CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4Each of which may be bonded to each other to form a ring. R101Z4The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z4Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z4、R102Z4And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[9] A compound represented by the formula (IZ 5).
Figure BDA0003121580680000101
[ formula (IZ5), RN1Z5represents-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5And R 7Z5Independently of one another, represents a hydrogen atom, -CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Each of which may be bonded to each other to form a ring, R2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5At least one group of them is bonded to form a ring.
R101Z5The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z5Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z5、R102Z5And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[10] A compound represented by the formula (IZ 6).
Figure BDA0003121580680000111
Figure BDA0003121580680000112
Figure BDA0003121580680000113
[ formula (IZ6)Wherein D represents a structure having an isoindoline skeleton. Z represents-SO3 -or-CO2 -。Ac+Represents a metal cation having a valence of c. a represents an integer of 1 to 10.
b represents an integer of 1 or more. c represents an integer of 2 to 10.
d represents an integer of 1 or more. D. Z, a or Ac+When there are a plurality of them, they may be the same or different. The formula (I 'Z6) and the formula (I' Z6) respectively represent partial structures of the formula (IZ6), D, Z, Ac+A, b, c and d represent the same meanings as the corresponding symbols in formula (IZ 6).
The partial structure represented by the formula (I' Z6) has the same negative valence as the partial structure represented by the formula (I "Z6) has the same positive valence in absolute value. ]
[11] The colored curable composition according to [2], further comprising a polymerization initiator.
The invention also includes:
1. a coloring composition comprising:
at least one of a resin and a solvent, and
1 or more selected from the group consisting of a compound represented by formula (IZ1), a compound represented by formula (IZ2), a compound represented by formula (IZ3), a compound represented by formula (IZ4), a compound represented by formula (IZ5), and a compound represented by formula (IZ 6);
Figure BDA0003121580680000114
in the formula (IZ1), RO1Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1and R7Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1May be bonded to each other to form a ring;
R101Z1represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z1represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z1、R102Z1and when there are a plurality of M, they may be the same or different; the wavy line represents the E or Z body;
Figure BDA0003121580680000121
in the formula (IZ2), RCO1Z2And RCO2Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2;RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2And R5Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z2and R3Z2、R3Z2And R4Z2And R4Z2And R5Z2May be bonded to each other to form a ring;
R101Z2represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
RO1Z2and R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2and when there are a plurality of M, they may be the same or different; the wavy line represents the E or Z body;
Figure BDA0003121580680000131
In the formula (IZ3), R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z3and R3Z3、R3Z3And R4Z3And R4Z3And R5Z3May be bonded to each other to form a ring;
R101Z3represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z3represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z3、R102Z3and when there are a plurality of M, they may be the same or different; the wavy line represents the E or Z body;
Figure BDA0003121580680000141
in the formula (IZ4), RN1Z4And RN2Z4Independently of one another represent-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4and R7Z4Independently of one another, represents a hydrogen atom, -CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z4and R3Z4、R3Z4And R4Z4And R4Z4And R5Z4May be bonded to each other to form a ring;
R101Z4Represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z4represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z4、R102Z4and when there are a plurality of M, they may be the same or different; the wavy line represents the E or Z body;
Figure BDA0003121580680000151
in the formula (IZ5), RN1Z5represents-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5and R7Z5Independently of one another, represents a hydrogen atom, -CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Each of which may be bonded to each other to form a ring, R2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5At least one group of them is bonded to form a ring;
R101Z5represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z5Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z5、R102Z5and when there are a plurality of M, they may be the same or different; the wavy line represents the E or Z body;
Figure BDA0003121580680000161
Figure BDA0003121580680000162
Figure BDA0003121580680000163
in the formula (IZ6), D represents a structure having an isoindoline skeleton; z represents-SO3 -or-CO2 -;Ac+A metal cation representing a valence of c; a represents an integer of 1 to 10;
b represents an integer of 1 or more; c represents an integer of 2 to 10; d represents an integer of 1 or more; D. z, a or Ac+When there are plural, they may be the same or different; the formula (I 'Z6) and the formula (I' Z6) respectively represent partial structures of the formula (IZ6), D, Z, Ac+A, b, c and d represent the same meanings as the corresponding symbols in formula (IZ 6);
the partial structure represented by the formula (I' Z6) has the same negative valence as the partial structure represented by the formula (I "Z6) has the same positive valence in absolute value.
2. The coloring composition as described in the above 1, which comprises: a compound represented by the formula (IZ1), a compound represented by the formula (IZ2), or a compound represented by the formula (IZ3), and a resin.
3. The coloring composition as described in the above 1, which comprises: a compound represented by formula (IZ4), a compound represented by formula (IZ5), or a compound represented by formula (IZ6), and a solvent.
4. The coloring composition according to the above 1 or 2, comprising a compound represented by the formula (IZ1) wherein R is1Z1、R6Z1And R7Z1Is a hydrogen atom.
5. The coloring composition according to 1 to 2 or 4, wherein the coloring composition comprises a compound represented by the formula (IZ1) wherein RO1Z1Is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
6. The coloring composition according to 1 to 2, 4 or 5, wherein the coloring composition comprises a compound represented by the formula (IZ1) wherein R is2Z1、R3Z1、R4Z1And R5Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1At least one group of them is bonded to form a ring.
7. The coloring composition according to any one of the above 1 to 2 or 4 to 6, which comprises a compound represented by the formula (IZ1) wherein R2Z1、R3Z1、R4Z1And R5Z1At least one of which is nitro or tert-butyl.
8. The coloring composition according to the above 1 or 2, comprising a compound represented by the formula (IZ2) wherein R isO1Z2、RN1Z2And RN2Z2Independently of each other, a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
9. The coloring composition according to 1 to 2 or 8, wherein the coloring composition comprises a compound represented by the formula (IZ2) wherein R1Z2Is a hydrogen atom.
10. 1 to 2, 8 orThe coloring composition according to 9, which comprises a compound represented by the formula (IZ2) wherein R is2Z2、R3Z2、R4Z2And R5Z2At least one of which is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2At least one group of them is bonded to form a ring.
11. The coloring composition according to any one of the above 1 to 2 or 8 to 10, which comprises a compound represented by the formula (IZ2) wherein R is2Z2、R3Z2、R4Z2And R5Z2At least one of which is nitro or tert-butyl.
12. The coloring composition according to the above 1 or 2, comprising a compound represented by the formula (IZ3) wherein R is1Z3、R6Z3And R7Z3Is a hydrogen atom.
13. The coloring composition according to 1 to 2 or 12, wherein the coloring composition comprises a compound represented by the formula (IZ3) wherein R2Z3、R3Z3、R4Z3And R5Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is 2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3At least one group of them is bonded to form a ring.
14. The coloring composition according to 1 to 2, 12 or 13, wherein the coloring composition comprises a compound represented by the formula (IZ3) wherein R is2Z3、R3Z3、R4Z3And R5Z3At least one of which is nitro or tert-butyl.
15. The coloring composition according to any one of the above 1 to 14, which comprises both a resin and a solvent.
16. The coloring composition according to any one of the above 1 to 15, further comprising a yellow coloring agent or a green coloring agent.
17. A colored curable composition comprising a polymerizable compound and the colored composition according to any one of 1 to 16.
18. The colored curable composition according to claim 17, further comprising a polymerization initiator.
19. A color filter comprising the colored composition according to any one of 1 to 16 or the colored curable composition according to 17 or 18.
20. A liquid crystal display device comprising the color filter according to 19.
21. A compound represented by the formula (IZ 1-B);
Figure BDA0003121580680000181
in the formula (IZ1-B),
RO11Z1represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R1Z1、R21Z1、R31Z1、R41Z1、R51Z1、R61Z1And R71Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R21Z1and R31Z1、R31Z1And R41Z1And R41Z1And R51Z1May be bonded to each other to form a ring;
wherein R is21Z1、R31Z1、R41Z1And R51Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z1And R31Z1、R31Z1And R41Z1And R41Z1And R51Z1At least one group of them is bonded to form a ring;
R101Z1represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z1representing a hydrogen atom which may have a substituentA hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic group which may have a substituent;
m represents a hydrogen atom or an alkali metal atom;
R101Z1、R102Z1and when there are a plurality of M, they may be the same or different;
the wavy line indicates the E-body or the Z-body.
22. The compound according to claim 21, wherein R1Z1、R61Z1And R71Z1Is a hydrogen atom.
23. The compound according to 21 or 22, wherein RO11Z1Is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
24. The compound according to any one of the above 21 to 23, wherein R21Z1、R31Z1、R41Z1And R51Z1At least one of which is nitro or tert-butyl.
25. A compound represented by the formula (IZ 2-B);
Figure BDA0003121580680000201
in the formula (IZ2-B), RCO11Z2And RCO21Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2,RCO11Z2And RCO21Z2At least one of which is-NRN1Z2RN2Z2
RN1Z2、RN2Z2、R1Z2、R21Z2、R31Z2、R41Z2And R51Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2A halogen atom,Cyano, nitro, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2Each of which may be bonded to each other to form a ring,
R21Z2、R31Z2、R41Z2and R51Z2At least one of which is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2At least one group of them is bonded to form a ring;
R101Z2represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
RO1Z2and R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2and when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
26. The compound of claim 25, wherein RO1Z2、RN1Z2And RN2Z2Is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
27. The compound according to claim 25 or 26, wherein R1Z2Is a hydrogen atom.
28. The compound according to any one of the above 25 to 27, wherein R21Z2、R31Z2、R41Z2And R51Z2At least one of which is nitro or tert-butyl.
29. A compound represented by the formula (IZ 3-B);
Figure BDA0003121580680000211
in the formula (IZ3-B), R1Z3、R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R21Z3and R31Z3、R31Z3And R41Z3And R41Z3And R51Z3May be bonded to each other to form a ring;
wherein R is21Z3、R31Z3、R41Z3And R51Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3At least one group of them is bonded to form a ring;
R101Z3represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z3represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
M represents a hydrogen atom or an alkali metal atom;
R101Z3、R102Z3and when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
30. The compound of claim 29, wherein R1Z3、R61Z3And R71Z3Is a hydrogen atom.
31. The compound according to claim 29 or 30, wherein R21Z3、R31Z3、R41Z3And R51Z3At least one of which is nitro or tert-butyl.
32. A compound represented by formula (IZ 4);
Figure BDA0003121580680000221
in the formula (IZ4), RN1Z4And RN2Z4Independently of one another represent-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4and R7Z4Independently of one another, represents a hydrogen atom, -CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z4and R3Z4、R3Z4And R4Z4And R4Z4And R5Z4May be bonded to each other to form a ring; r101Z4Represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z4represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z4、R102Z4And when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
33. The compound of 32, wherein R1Z4、R6Z4And R7Z4Is a hydrogen atom.
34. The compound according to the above 32 or 33, wherein RN1Z4And RN2Z4Independently of each other, a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
35. The compound according to any one of the above 32 to 34, wherein R2Z4、R3Z4、R4Z4And R5Z4At least one of which is-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4At least one group of them is bonded to form a ring.
36. The compound according to any one of the above 32 to 35, wherein R2Z4、R3Z4、R4Z4And R5Z4At least one of which is nitro or tert-butyl.
37. A compound represented by formula (IZ 5);
Figure BDA0003121580680000231
in the formula (IZ5), RN1Z5represents-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5and R7Z5Independently of one another, represents a hydrogen atom, -CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is 2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Each of which may be bonded to each other to form a ring, R2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5At least one group of them is bonded to form a ring;
R101Z5represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group; r102Z5Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z5、R102Z5and when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
38. The compound of claim 37, wherein RN1Z5The hydrocarbon group may have a substituent and has 1 to 10 carbon atoms.
39. The compound according to 37 or 38, wherein R1Z5、R6Z5And R7Z5Is a hydrogen atom.
40. The compound according to any one of claims 37 to 39, wherein R2Z5、R3Z5、R4Z5And R5Z5At least one of which is nitro or tert-butyl.
41. A compound represented by formula (IZ 6);
Figure BDA0003121580680000251
Figure BDA0003121580680000252
Figure BDA0003121580680000253
in the formula (IZ6), D represents a structure having an isoindoline skeleton; z represents-SO 3 -or-CO2 -;Ac+A metal cation representing a valence of c; a represents an integer of 1 to 10;
b represents an integer of 1 or more; c represents an integer of 2 to 10;
d represents an integer of 1 or more; D. z, a or Ac+When there are plural, they may be the same or different; the formula (I 'Z6) and the formula (I' Z6) respectively represent partial structures of the formula (IZ6), D, Z, Ac+A, b, c and d represent the same meanings as the corresponding symbols in formula (IZ 6);
the partial structure represented by the formula (I' Z6) has the same negative valence as the partial structure represented by the formula (I "Z6) has the same positive valence in absolute value.
42. The compound according to 41, wherein the compound represented by formula (IZ6) is a compound represented by formula (IZ 6-A);
Figure BDA0003121580680000254
Figure BDA0003121580680000255
Figure BDA0003121580680000256
in the formula (IZ6-A), Ac+B, c and d are as defined above;
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6and R13AZ6Independently of one another, represents a hydrogen atom, -CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -A C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R2AZ6and R3AZ6、R3AZ6And R4AZ6、R4AZ6And R5AZ6、RAA1Z6And RAA2Z6And R12AZ6And R13AZ6May be bonded to each other to form a ring;
R101AZ6independently represent a C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R102AZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
the formula (IZ6-A ') and the formula (IZ 6-A') each represent a partial structure of the formula (IZ6-A), Ac+、b、c、d、R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Represents the same meaning as the corresponding symbol in formula (IZ 6-A);
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6、R102AZ6m, c or Ac+When there are plural, they may be the same or different;
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6and R102AZ6Satisfies at least 1 of (ra-i) to (ra-iii), R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6having-SO of3 -or-CO2 -The total number of (a);
(ra-i)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6and R13AZ6At least one of which is-SO3 -or-CO2 -
(ra-ii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is-CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6or-OCON (R)102AZ6)2R is a hydrogen atom101AZ6And R102AZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
(ra-iii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6and R13AZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group and the heterocyclic group may have-SO3 -or-CO2 -A substituent other than;
a represents the same meaning as the symbol in formula (IZ 6); when a plurality of a exist, they may be the same or different;
The negative valence number of the partial structure represented by the formula (IZ 6-A') is the same as the absolute value of the positive valence number of the partial structure represented by the formula (IZ6-A ");
the wavy line indicates the E-body or the Z-body.
43. The compound according to item 42, wherein the compound represented by formula (IZ6-A) is a compound represented by formula (IZ 6-B);
Figure BDA0003121580680000271
Figure BDA0003121580680000272
Figure BDA0003121580680000273
in the formula (IZ6-B), Ac+B, c, d and the wavy line have the same meanings as described above; l is1represents-CO-or-SO2-;
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6Independently of one another, represents a hydrogen atom, -CO-R102BZ6、-COO-R101BZ6、-OCO-R102BZ6、-COCO-R102BZ6、-O-R102BZ6、-SO2-R101BZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102BZ6、-NHCO-N(R102AZ6)2、-NHCOOR102BZ6、-OCON(R102AZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -A C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R2BZ6and R3BZ6、R3BZ6And R4BZ6、R4BZ6And R5BZ6And R12BZ6And R13BZ6May be bonded to each other to form a ring;
R101BZ6independently of each other, the number of carbon atoms which may have a substituent1 to 40 hydrocarbon groups or heterocyclic groups which may have substituents;
R102BZ6independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
the formula (IZ6-B ') and the formula (IZ 6-B') each represent a partial structure of the formula (IZ6-B), Ac+、b、c、d、R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6And L1Represents the same meaning as the corresponding symbol in formula (IZ 6-B);
m represents the same meaning as described above;
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6、R102BZ6、L1M, c or Ac+When there are plural, they may be the same or different;
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6and R102BZ6Satisfies at least 1 of (rb-i) to (rb-iii), R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6having-SO of3 -or-CO2 -The total number of (a);
(rb-i)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6and R13BZ6At least one of which is-SO3 -or-CO2 -
(rb-ii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is-CO-R102BZ6、-COO-R101BZ6、-OCO-R102BZ6、-COCO-R102BZ6、-O-R102BZ6、-SO2-R101BZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102BZ6、-NHCO-N(R102AZ6)2、-NHCOOR102BZ6or-OCON (R)102AZ6)2
The R is101BZ6And R102BZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
(rb-iii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6and R13BZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
a represents the same meaning as the symbol in the formula (IZ 6-A); when a plurality of a exist, they may be the same or different;
the partial structure represented by the formula (IZ6-B ') has the same negative valence as the partial structure represented by the formula (IZ 6-B') has the same positive valence in absolute value.
44. The compound of 43, wherein L1is-CO-.
45. The compound according to 43 or 44, wherein R11BZ6An optionally substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an optionally substituted phenyl group, an optionally substituted naphthyl group, an optionally substituted tetrahydronaphthyl group A thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent.
46. The compound according to 43, wherein the compound represented by the formula (IZ6-B) is a compound represented by the formula (IZ 6-C);
Figure BDA0003121580680000291
Figure BDA0003121580680000292
Figure BDA0003121580680000293
in the formula (IZ6-C), Ac+、b、c、d、L1And the wavy line means the same as above;
L2represents-CO-or-SO2-;
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6Independently of one another, represents a hydrogen atom, -CO-R102CZ6、-COO-R101CZ6、-OCO-R102CZ6、-COCO-R102CZ6、-O-R102CZ6、-SO2-R101CZ6、-SO2N(R102CZ6)2、-CON(R102CZ6)2、-N(R102CZ6)2、-NHCO-R102CZ6、-NHCO-N(R102CZ6)2、-NHCOOR102CZ6、-OCON(R102CZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -A C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R2CZ6and R3CZ6、R3CZ6And R4CZ6And R4CZ6And R5CZ6Respectively can beBonded to each other to form a ring;
R101CZ6independently represent a C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R102CZ6independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents the same meaning as described above;
the formula (IZ6-C ') and the formula (IZ 6-C') each represent a partial structure of the formula (IZ6-C), Ac+、b、c、d、R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、L1And L2Represents the same meaning as the corresponding symbol in formula (IZ 6-C);
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6、R102CZ6、L1、L2m, c or Ac+When there are plural, they may be the same or different;
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6Satisfies at least 1 of (rc-i) to (rc-iii), R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6having-SO of3 -or-CO2 -The total number of (a);
(rc-i)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6and R14CZ6At least one of which is-SO3 -or-CO2 -
(rc-ii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is-CO-R102CZ6、-COO-R101CZ6、-OCO-R102CZ6、-COCO-R102CZ6、-O-R102CZ6、-SO2-R101CZ6、-SO2N(R102CZ6)2、-CON(R102CZ6)2、-N(R102CZ6)2、-NHCO-R102CZ6、-NHCO-N(R102CZ6)2、-NHCOOR102CZ6or-OCON (R)102CZ6)2R is a hydrogen atom101CZ6And R102CZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
(rc-iii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6and R14CZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
a represents the same meaning as the symbol in the formula (IZ 6-B); when a plurality of a exist, they may be the same or different;
the partial structure represented by the formula (IZ 6-C') has the same negative valence as the partial structure represented by the formula (IZ6-C ") has the same positive valence in absolute value.
47. The compound of 46, wherein R11CZ6And R14CZ6Are identical radicals, L1And L2Are the same group.
48. The compound of claim 46 or 47, wherein L1And L2is-CO-.
49. Any one of the above 46 to 48A compound of formula (I) wherein R 11CZ6And R14CZ6The alkyl group is an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent.
50. The compound according to 43, wherein the compound represented by the formula (IZ6-B) is a compound represented by the formula (IZ 6-D);
Figure BDA0003121580680000321
Figure BDA0003121580680000322
Figure BDA0003121580680000323
in the formula (IZ6-D), Ac+、b、c、d、L1And the wavy line means the same as above; r20DZ6And R30DZ6Bonded to form a ring Q; the ring Q may have a substituent, and is a ring having 5 to 7 constitutional elements of the ring, and the ring Q may be a hydrocarbon ring or a heterocyclic ring; the following rings may be fused/condensed on ring Q: a monocyclic ring which is selected from hydrocarbon rings and hetero rings and which may have a substituent, wherein the number of constituent elements of the ring is 5 to 7; or a condensed ring in which at least 2 of the monocyclic rings are condensed;
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6and R11DZ6Independently of one another, represents a hydrogen atom, -CO-R102DZ6、-COO-R101DZ6、-OCO-R102DZ6、-COCO-R102DZ6、-O-R102DZ6、-SO2-R101DZ6、-SO2N(R102DZ6)2、-CON(R102DZ6)2、-N(R102DZ6)2、-NHCO-R102DZ6、-NHCO-N(R102DZ6)2、-NHCOOR102DZ6、-OCON(R102DZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -A C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R2DZ6and R3DZ6、R3DZ6And R4DZ6And R4DZ6And R5DZ6May be bonded to each other to form a ring;
R101DZ6Independently represent a C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R102DZ6independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents the same meaning as described above;
the formulae (IZ 6-D') and (IZ6-D ") each represent a partial structure of the formula (IZ6-D), Ac+、b、c、d、R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R20DZ6、R30DZ6And L1Represents the same meaning as the corresponding symbol in the formula (IZ 6-D);
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6、L1、M、R20DZ6、R30DZ6ring Q, c or Ac+When there are plural, they may be the same or different;
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6and ring Q satisfies at least 1 of (rd-i) to (rd-iv), R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6And ring Q hasis-SO of3 -or-CO2 -The total number of (a);
(rd-i)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6and R11DZ6At least one of which is-SO3 -or-CO2 -
(rd-ii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is-CO-R102DZ6、-COO-R101DZ6、-OCO-R102DZ6、-COCO-R102DZ6、-O-R102DZ6、-SO2-R101DZ6、-SO2N(R102DZ6)2、-CON(R102DZ6)2、-N(R102DZ6)2、-NHCO-R102DZ6、-NHCO-N(R102DZ6)、-NHCOOR102DZ6or-OCON (R)102DZ6)2R is a hydrogen atom101DZ6And R102DZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
(rd-iii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6and R11DZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO 2 -A substituent other than;
(rd-iv) Ring Q has-SO3 -or-CO2 -
a represents the same meaning as the symbol in the formula (IZ 6-B); when a plurality of a exist, they may be the same or different;
the partial structure represented by the formula (IZ 6-D') has the same negative valence as the partial structure represented by the formula (IZ6-D ") has the same positive valence in absolute value.
51. A compound as claimed in 50 above, wherein L1is-CO-.
52. The compound according to 50 or 51, wherein R11DZ6The alkyl group is an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent.
53. The compound according to 50, wherein the compound represented by the formula (IZ6-D) is a compound represented by the formula (IZ 6-E);
Figure BDA0003121580680000341
Figure BDA0003121580680000342
Figure BDA0003121580680000343
in the formula (IZ6-E), Ac+、b、c、d、L1And the wavy line means the same as above;
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6and R11EZ6Independently of one another, represents a hydrogen atom, -CO-R102EZ6、-COO-R101EZ6、-OCO-R102EZ6、-COCO-R102EZ6、-O-R102EZ6、-SO2-R101EZ6、-SO2N(R102EZ6)2、-CON(R102EZ6)2、-N(R102EZ6)2、-NHCO-R102EZ6、-NHCO-N(R102EZ6)2、-NHCOOR102EZ6、-OCON(R102EZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -A C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent; r 2EZ6And R3EZ6、R3EZ6And R4EZ6And R4EZ6And R5EZ6May be bonded to each other to form a ring;
R101EZ6independently represent a C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R102EZ6independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group; m represents the same meaning as described above;
the formulae (IZ6-E ') and (IZ 6-E') each represent a partial structure of the formula (IZ6-E), Ac+、b、c、d、R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6And L1Represents the same meaning as the corresponding symbol in formula (IZ 6-E);
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6、R102EZ6、L1m, c or Ac+When there are plural, they may be the same or different;
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6and R102EZ6Satisfies at least 1 of (re-i) to (re-iii), R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6having-SO of3 -or-CO2 -The total number of (a);
(re-i)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6and R11EZ6At least one of which is-SO3 -or-CO2 -
(re-ii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is-CO-R102EZ6、-COO-R101EZ6、-OCO-R102EZ6、-COCO-R102EZ6、-O-R102EZ6、-SO2-R101EZ6、-SO2N(R102EZ6)2、-CON(R102EZ6)2、-N(R102EZ6)2、-NHCO-R102EZ6、-NHCO-N(R102EZ6)2、-NHCOOR102EZ6or-OCON (R)102EZ6)2R is a hydrogen atom101EZ6And R102EZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
(re-iii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6and R11EZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO 3 -and-CO2 -A substituent other than;
a represents the same meaning as the symbol in the formula (IZ 6-D); when a plurality of a exist, they may be the same or different;
the partial structure represented by the formula (IZ6-E ') has the same negative valence as the partial structure represented by the formula (IZ 6-E') has the same positive valence in absolute value.
54. A compound as described in 53 above, wherein L1is-CO-.
55. The compound according to 53 or 54 above, wherein R11EZ6The alkyl group is an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent.
Detailed Description
The coloring composition of the present invention comprises: at least one of a resin (hereinafter, sometimes referred to as a resin (B)) and a solvent (hereinafter, sometimes referred to as a solvent (E)), and at least one selected from the group consisting of a compound represented by formula (IZ1) (hereinafter, sometimes referred to as a compound IZ 1)), a compound represented by formula (IZ2) (hereinafter, sometimes referred to as a compound IZ 2)), a compound represented by formula (IZ3) (hereinafter, sometimes referred to as a compound IZ3), a compound represented by formula (IZ4) (hereinafter, sometimes referred to as a compound IZ4), a compound represented by formula (IZ5) (hereinafter, sometimes referred to as a compound IZ5), and a compound represented by formula (IZ6) (hereinafter, sometimes referred to as a compound IZ6) (hereinafter, sometimes referred to as a compound Z).
The compound IZ1, the compound IZ2, the compound IZ3, the compound IZ4, the compound IZ5 and the compound IZ6 include tautomers thereof and salts thereof, respectively.
The above compounds can be used as colorants, respectively.
The coloring composition of the present invention may contain 1 or 2 or more compounds IZ1, may contain 1 or 2 or more compounds IZ2, may contain 1 or 2 or more compounds IZ3, may contain 1 or 2 or more compounds IZ4, may contain 1 or 2 or more compounds IZ5, and may contain 1 or 2 or more compounds IZ 6.
When the coloring composition of the present invention contains 1 or more selected from the group consisting of the compound IZ1, the compound IZ2, and the compound IZ3, it is preferable that the coloring composition contains the resin (B) as an essential component.
When the coloring composition of the present invention contains 1 or more selected from the group consisting of the compound IZ4, the compound IZ5, and the compound IZ6, it is preferable that the coloring composition contains the solvent (E) as an essential component.
When the coloring composition of the present invention contains a solvent, the compound IZ1, the compound IZ2, the compound IZ3, the compound IZ4, the compound IZ5, and the compound IZ6 are preferably dispersed in the solvent (E).
When the coloring composition of the present invention contains the compound IZ1, the coloring composition may further contain a colorant other than the compound IZ1 (hereinafter, sometimes referred to as the colorant a1z1. also, hereinafter, sometimes the compound IZ1 and the colorant A1Z1 are collectively referred to as the "colorant AZ 1"). The colorant A1Z1 may contain 1 or 2 or more colorants.
When the coloring composition of the present invention contains the compound IZ2, the coloring composition may further contain a colorant other than the compound IZ2 (hereinafter, sometimes referred to as a colorant a1z2. also, hereinafter, sometimes the compound IZ2 and the colorant A1Z2 are collectively referred to as a "colorant AZ 2"). The colorant A1Z2 may contain 1 or 2 or more colorants.
When the coloring composition of the present invention contains the compound IZ3, the coloring composition may further contain a colorant other than the compound IZ3 (hereinafter, sometimes referred to as a colorant a1z3. also, hereinafter, sometimes the compound IZ3 and the colorant A1Z3 are collectively referred to as a "colorant AZ 3"). The colorant A1Z3 may contain 1 or 2 or more colorants.
When the coloring composition of the present invention contains the compound IZ4, the coloring composition may further contain a colorant other than the compound IZ4 (hereinafter, sometimes referred to as a colorant a1z4. also, hereinafter, sometimes the compound IZ4 and the colorant A1Z4 are collectively referred to as a "colorant AZ 4"). The colorant A1Z4 may contain 1 or 2 or more colorants.
When the coloring composition of the present invention contains the compound IZ5, the coloring composition may further contain a colorant other than the compound IZ5 (hereinafter, sometimes referred to as a colorant a1z5. furthermore, hereinafter, sometimes the compound IZ5 and the colorant A1Z5 are collectively referred to as a "colorant AZ 5"). The colorant A1Z5 may contain 1 or 2 or more colorants.
When the coloring composition of the present invention contains the compound IZ6, the coloring composition may further contain a colorant other than the compound IZ6 (hereinafter, sometimes referred to as a colorant a1z6. furthermore, the compound IZ6 and the colorant A1Z6 are sometimes collectively referred to as a "colorant AZ 6"). The colorant A1Z6 may contain 1 or 2 or more colorants.
Hereinafter, 1 or more selected from the group consisting of the colorant A1Z1, the colorant A1Z2, the colorant A1Z3, the colorant A1Z4, the colorant A1Z5, and the colorant A1Z6 are collectively referred to as the colorant ZZ. The colorant ZZ preferably comprises a yellow colorant or a green colorant.
Hereinafter, 1 or more selected from the colorant AZ1, the colorant AZ2, the colorant AZ3, the colorant AZ4, the colorant AZ5, and the colorant AZ6 will be collectively referred to as a colorant ZZZ.
The coloring composition of the present invention preferably contains both the resin (B) and the solvent (E).
Further, the colored curable composition of the present invention comprises:
at least one selected from the group consisting of a compound represented by the formula (IZ1), a compound represented by the formula (IZ2), a compound represented by the formula (IZ3), a compound represented by the formula (IZ4), a compound represented by the formula (IZ5) and a compound represented by the formula (IZ6), and
at least one of resin (B) and solvent (E), and
A polymerizable compound (C).
In other words, the colored curable composition of the present invention comprises a colored composition and a polymerizable compound (C).
The colored curable composition of the invention may contain a polymerization initiator (D).
The colored curable composition of the invention may contain a polymerization initiation aid (D1).
The coloring composition of the present invention may further comprise a leveling agent (F) and an antioxidant.
< Compound IZ1 >)
Compound IZ1 is a compound represented by formula (IZ 1).
Figure BDA0003121580680000381
[ formula (IZ1), RO1Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1Each of which may be bonded to each other to form a ring. R101Z1The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R 101Z1、R102Z1And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The number of carbon atoms of the hydrocarbon group is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10。
RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, further more preferably 1 to 8, and particularly preferably 1 to 5. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable, and a methyl group, an ethyl group, and a tert-butyl group are particularly preferable.
As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and 1-methylcyclohexyl2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1, 2-dimethylcyclohexyl group, 1, 3-dimethylcyclohexyl group, 1, 4-dimethylcyclohexyl group, 2, 3-dimethylcyclohexyl group, 2, 4-dimethylcyclohexyl group, 2, 5-dimethylcyclohexyl group, 2, 6-dimethylcyclohexyl group, 3, 4-dimethylcyclohexyl group, 3, 5-dimethylcyclohexyl group, 2-dimethylcyclohexyl group, 3-dimethylcyclohexyl group, 4-dimethylcyclohexyl group, cyclooctyl group, 2,4, 6-trimethylcyclohexyl group, 2,6, 6-tetramethylcyclohexyl group, 3,5, 5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 3, 4-octylcyclohexyl group, 1, 3-dimethylcyclohexyl group, 2, 4-dimethylcyclohexyl group, 3, 5-dimethylcyclohexyl group, 3-dimethylcyclohexyl group, 4-dimethylcyclohexyl group, 3, 4-dimethylcyclohexyl group, 2, 6-dimethylcyclohexyl group, 2,3, 5-dimethylcyclohexyl group, 4-dimethylcyclohexyl group, 3, 4-dimethylcyclohexyl group, 2,3, 2, 4-dimethylcyclohexyl group, 2,3, 4-dimethylcyclohexyl group, 2, 4-dimethylcyclohexyl group, 3, 2,3, 2,3, 4-dimethylcyclohexyl group, 2,6, 2,3, 2,6, 2,3, 6, 3, 2,6, and the like, Cycloalkyl groups such as 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl are particularly preferable.
As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1、R101Z1And R102Z1The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a mesityl (mesityl group), a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 4-pentylphenyl group, a, Aromatic hydrocarbon groups such as 2-naphthyl, 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracyl, pyrenyl and the like; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1Examples of the group represented by the above-mentioned groups, which are a combination of the above-mentioned hydrocarbon groups (e.g., chain hydrocarbon groups and alicyclic hydrocarbon groups), include alkyl groups to which 1 or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl groups, cyclopropylethyl groups, cyclobutylmethyl groups, cyclobutylethyl groups, cyclopentylmethyl groups, cyclopentylethyl groups, cyclohexylmethyl groups, 2-methylcyclohexylmethyl groups, cyclohexylethyl groups, and adamantylmethyl groups.
The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbon group represented may have a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
Figure BDA0003121580680000421
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl;
a formyl group;
a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
Figure BDA0003121580680000431
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
Figure BDA0003121580680000432
Figure BDA0003121580680000441
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formula);
Figure BDA0003121580680000451
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, N-phenylmethylsulfamoyl, and the like, and groups represented by the following chemical formulae);
Figure BDA0003121580680000461
Figure BDA0003121580680000471
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
Figure BDA0003121580680000472
Figure BDA0003121580680000481
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is an alkali metal, preferably lithium, sodium, potassium); a nitro group; a cyano group; a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
Figure BDA0003121580680000482
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
Figure BDA0003121580680000491
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
Figure BDA0003121580680000501
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, or a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3、-CO-S-CH2-CH2-CH2-CH3a thio group bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms)Carbonyl (thiocarbonyl), -CO-S-C 6H5A thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms;
a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
Figure BDA0003121580680000511
-NRCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
Figure BDA0003121580680000521
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
Figure BDA0003121580680000531
A group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
Figure BDA0003121580680000541
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR3(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring); and so on.
Examples of the substituent having a valence of 2 include an oxo (oxo) group, a thioxo (thioxo) group, an imino group, and a group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms)And imino groups substituted with an aryl group having 6 to 20 carbon atoms. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof; a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom; -CO 2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; oxo radical。
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
An amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a hydroxyl group; fluorine atom, chlorine atom, bromine atom;
-CO2m (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent;
a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbyl group having 1 to 40 carbon atoms which is a substituent represented by the formula (I) includes those having 1 to 40 carbon atoms which are substituents having a valence of 1 or 2The hydrocarbon group is preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, or a group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which is a combination of hydrocarbon groups,
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups having 1 to 20 carbon atoms having a substituent of group s1,
particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 1 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The heterocyclic group represented by (a) may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include:
monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine;
five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole;
a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine;
a fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine;
Condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane; bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone-based heterocycles such as α -acetolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone;
five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran; fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole (benzodioxole), chroman and isochroman; fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include a five-membered ring system saturated heterocyclic ring such as dithiolane; saturated heterocycles with six-membered ring systems, such as thiacyclohexane (thiane), 1, 3-dithiane, 2-methyl-1, 3-dithiane; a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran); fused bicyclic heterocycles such as benzothiophene;
Fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include:
monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone;
a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole); fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
Figure BDA0003121580680000581
The above heterocyclic group may be R1Z1~R5Z12 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1Z1~R5Z1The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
Figure BDA0003121580680000591
The bonding position of the heterocycle is a portion where any hydrogen atom contained in each ring is removed.
RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The heterocyclic group represented may have a substituent. As the substituent, there may be mentionedAre mentioned with RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbon group may have the same substituent as the substituent. In addition, in the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom.
Preferred examples of the substituent includeO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The preferable examples of the substituents which the hydrocarbon group may have are the same. As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The heterocyclic group having a substituent represented by the formula (i) includes a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s 2.
The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1Of (a) is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, -SO3M、-CO2M is explained.
as-CO-R102Z1Examples thereof include a formyl group; acetyl, propionyl, butyryl, 2-dimethylpropionyl, pentanoyl, hexanoyl, (2-ethyl) hexanoyl, heptanoyl, examples of the carbonyl group include a carbonyl group (in the case where the carbonyl group is an acyl group, the number of carbon atoms is 2 to 41) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyl group, a nonanoyl group, a decanoyl group, a undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group, and the compounds shown in tables 1Z1 to 7Z1 and 10Z1 to 13Z1 correspond to — CO — R.102Z1Preferable examples of the group(s) include a carbonyl group (more preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to-CO-R 102Z1And the like.
as-COO-R101Z1Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl and heptyloxycarbonyl, an oxycarbonyl group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group, an eicosyloxycarbonyl group and the like, and the groups represented by the above chemical formulae, and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to-COO-R.101Z1Preferred examples of the group (b) include oxycarbonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 which correspond to-COO-R101Z1And the like.
as-OCO-R102Z1Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy and the like, carbonyloxy (carbon number 2 to 41 in the case where the carbonyloxy group is an acyloxy group), carbonyloxy group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as the group represented by the above chemical formula, and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to-OCO- R 102Z1Preferable examples of the group(s) include a carbonyloxy group (more preferably 2 to 12 carbon atoms in the case where the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 corresponds to-OCO-R102Z1And the like.
as-COCO-R102Z1Examples thereof include a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof bonded (for example, via a carboxyl group, a sulfo group, a nitro group, a carboxyl group, a sulfo group, a carboxyl group, a nitro group, a carboxyl group, a sulfo group, a pentyl group, a hexyl group, a (2-ethyl) hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, an eicosyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a tolyl group, a p-tolyl group and the likeOxalyl groups derived from a hydroxyl group, a halogen (preferably chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like), and compounds represented by tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1, wherein the oxalyl groups correspond to-COCO-R 102Z1And the like.
as-O-R102Z1There may be mentioned a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 5-dimethylphenyloxy, 2, 6-dimethylphenyloxy, 3, 4-dimethylphenyloxy, 3, 5-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 3-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 4-di-yloxy, 2-di-methyl-1-phenylethoxy, 2, 4-di-methyl, and mixtures thereof, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, examples of the oxygen group include an oxygen group having a hydrocarbyl group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like bonded thereto, such as a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or the like, and a group represented by the above chemical formulae), and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to — O — R. 102Z1Preferred examples of the group (b) include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1, which correspond to-O-R102Z1And the like.
as-SO2-R101Z1Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl) hexylsulfonyl, and heptylsulfonylSulfonyl groups in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a alkylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, and the like, and a group represented by the above chemical formulae (i) and (ii) are bonded, and (ii) compounds corresponding to-SO in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 are listed2-R101Z1Preferable examples of the group (b) include sulfonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds represented by tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1, which correspond to-SO 2-R101Z1And the like.
as-SO2N(R102Z1)2Examples thereof include:
a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl, N-phenylsulfamoyl, etc., and a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula, or a derivative thereof Sulfamoyl substituted with a raw group (e.g., a group derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), etc.), and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1, which correspond to-SO2NH(R102Z1X)(R102Z1XIs not a hydrogen atom, other than, and R102Z1The same as defined above), etc.;
N, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylsulfamoyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diethylsulfamoyl, N, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylmethylsulfamoyl, N-phenylmethylsulfamoyl, N-diphenylsulfamoyl and the like, and sulfamoyl groups represented by the above chemical formulae and the like substituted with a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl) and the like), and sulfamoyl groups shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 Corresponding to-SO in the compound 2N(R102Z1X)2(wherein, R102Z1XIs not a hydrogen atom, other than, and R102Z1The same as defined above) and the like,
preferred examples thereof include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof, and compounds represented by tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1, which correspond to-SO2N(R102Z1)2And the like.
as-CON (R)102Z1)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoylCarbamoyl groups such as carbamoyl, N- (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-decylcarbamoyl, N-undecylcarbamoyl, N-dodecylcarbamoyl, N-eicosylcarbamoyl, N-phenylcarbamoyl and the like, and carbamoyl groups represented by the above chemical formulae which are substituted with a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) and the like), and also, in tables 1Z1 to 7Z1 and 10Z1 to the compounds shown in Table 13Z1 correspond to-CONH (R) 102Z1X) (wherein, R102Z1XIs not a hydrogen atom, other than, and R102Z1The same as defined above), etc.;
n, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-tert-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-diethylcarbamoyl group, N-diisopropylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-isobutylcarbamoyl group, N-di (s-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-di-N-butylcarbamoyl group, N, a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, an N, N-di (2-ethyl) hexylcarbamoyl group, an N, N-diheptylcarbamoyl group, an N, N-octylmethylcarbamoyl group, an N, N-dinonylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, an N, N-diphenylcarbamoyl group, etc., and a group represented by the above chemical formula, Nitro, hydroxy, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group), and the like) and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to-CON (R)102Z1X)2(wherein, R102Z1XIs not a hydrogen atom, other than, and R102Z1The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z1 to 7Z1 and 10Z1 to 13Z1 which corresponds to-CON (R)102Z1)2And the like.
as-N (R)102Z1)2Examples thereof include:
an amino group; a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom)), such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, an N-tert-butylamino group, an N-pentylamino group, an N-hexylamino group, an N- (2-ethyl) hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-undecylamino group, an N-dodecylamino group, an N-eicosylamino group, an N-phenylamino group, and the like, and a group represented by the above chemical formula, A group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like) and a compound shown in tables 1Z1 to 7Z1 and 10Z1 to 13Z1, wherein the compound corresponds to-NH (R 102Z1X) (wherein, R102Z1XIs not a hydrogen atom, other than, and R102Z1The same as defined above), etc.;
n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-dipentylamino group, N-bis (1-ethylpropyl) amino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di (1-ethylpropyl) amino group, N-di (tert-butylamino group, N-dibutylamino group, N-dipentylamino group, N-di (1-ethylpropyl) amino group, N-di (i-butylamino group, N-butylamino group, N-butylamino group, N-butylamino group, N-butylamino, N, or the like, N, or the like, N,an amino group substituted with a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like, and a compound shown in tables 1Z1 to 7Z1 and tables 10Z 35 1 to 13Z1, such as a compound shown in tables 1Z 8932 and tables 10Z 353925 Is equivalent to-N (R) 102Z1X)2And the like,
preferred examples thereof include amino groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 which correspond to-N (R)102Z1)2And the like.
as-NHCO-R102Z1Examples thereof include formylamino; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecanoylamino, dodecanoylamino, heneicosanoylamino, benzoylamino and the like, carbonylamino (carbon number 1 to 40 in the case of carbonylamino being an acylamino group, carbon number 1 to 40 in the case of carbonylamino), carbonylamino to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 in the case of carbonylamino being a carbonylamino group) or a derivative thereof (for example, a derivative thereof such as a hydrocarbon group having 1 to 10 carbon atoms (preferably a C1 to 10 alkylsulfamoyl group) is bonded such as a group represented by the above formula, and compounds represented by tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to-NHCO- R 102Z1And the like,
preferably, the carbonyl amino group (in which the carbonyl amino group is an alkanoylamino group) to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bondedIn the case where the number of carbon atoms is more preferably 1 to 10), and the compounds shown in Table 1Z1 to Table 7Z1 and Table 10Z1 to Table 13Z1 correspond to-NHCO-R102Z1And the like.
as-NHCON (R)102Z1)2Examples thereof include the groups listed above and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 which correspond to-NHCON (R)102Z1)2And the like.
as-NHCOOR102Z1Examples thereof include those corresponding to-NHCOOR among the above-mentioned groups and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1102Z1And the like.
as-OCON (R)102Z1)2Examples thereof include those corresponding to-OCON (R) among the above-mentioned groups and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1102Z1)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M in M is a hydrogen atom; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102Z1、-COO-R102Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R102Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCON(R102Z)2、-NHCOOR102Z1、-OCON(R102Z1)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 1). As R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene (biphenylene), indacene (indacene), acenaphthylene, fluorene, phenalene (phenalene), phenanthrene, anthracene, fluoranthene, acephenanthrylene (aceanthrylene), aceanthrylene (aceanthrylene), and benzo [9,10 ] benzo]Phenanthrene (triphenylene), pyrene,
Figure BDA0003121580680000671
Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide, and tetracene, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, and the like); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,
Figure BDA0003121580680000672
Nitrogen-containing fused heterocycles such as pyridine, phenanthroline, and phenazine, and partial reductants thereof; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1In the case of forming a ring, the ring may have a substituent. Examples of the substituent includeO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent includeO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3Z1And R4Z1When forming a ring, as R2Z1And R5Z1Independently of one another, hydrogen atoms, amino groups and hydroxyl groups are preferred.
R2Z1And R3Z1When a ring is formed, R is preferably4Z1And R5Z1Does not form a ring, more preferably R4Z1And R5Z1Is a hydrogen atom.
In addition, R4Z1And R5Z1When a ring is formed, R is preferably2Z1And R3Z1Does not form a ring, more preferably R2Z1And R3Z1Is a hydrogen atom.
In the present invention, R1Z1、R6Z1And R7Z1Preferably a hydrogen atom.
In the present invention, RO1Z1The hydrocarbon group is preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, particularly preferably a hydrogen atom, a methyl group, an ethyl group or a phenyl group, and most preferably a hydrogen atom, a methyl group or an ethyl group.
From the viewpoint of reducing the retardation value of a color filter made of the colored composition, R is preferably2Z1、R3Z1、R4Z1And R5Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、A hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent,
more preferably a C1-40 hydrocarbon group which may have a substituent, a halogen atom, or-N (R)102Z1)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z1、-O-R102Z1、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Alternatively, R is preferred2Z1And R3Z1、R3Z1And R4Z1Or R4Z1And R5Z1Form a ring.
Compound IZ1 is preferably the following compound: r2Z1、R3Z1、R4Z1And R5Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1At least one group of the compounds (hereinafter, this compound may be referred to as "compound IZ 1-B") is bonded to form a ring. When the compound IZ1 is the compound IZ1-B, the retardation value of the color filter produced from the colored composition becomes small.
From the viewpoint of reducing the retardation value of a color filter made of the colored composition, R is preferably2Z1、R3Z1、R4Z1And R5Z1At least one of the above (B) is a C1-4 carbon atom which may have a substituent0 hydrocarbyl group, halogen atom, -N (R)102Z1)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z1、-O-R102Z1、-SO3M or-CO2M,
More preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. It is especially preferred that R3Z1Is nitro or tert-butyl, R2Z1、R4Z1And R5Z1Is a hydrogen atom; or, R2Z1、R3Z1And R5Z1Is a hydrogen atom, R4Z1Is nitro or tert-butyl.
When the above compound IZ1-B is defined by a chemical formula, it is as follows.
Figure BDA0003121580680000691
[ formula (IZ1-B) wherein RO11Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. R1Z1、R21Z1、R31Z1、R41Z1、R51Z1、R61Z1And R71Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R21Z1And R31Z1、R31Z1And R41Z1And R41Z1And R51Z1Can be bonded to each other to form a ring。
Wherein R is21Z1、R31Z1、R41Z1And R 51Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z1And R31Z1、R31Z1And R41Z1And R41Z1And R51Z1At least one group of them is bonded to form a ring. R101Z1The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z1、R102Z1And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
With respect to R in the formula (IZ1-B)O11Z1、R21Z1、R31Z1、R41Z1、R51Z1、R61Z1And R71Z1Respectively, R in the formula (IZ1)O1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1The same example.
With respect to the preferred R in the formula (IZ1-B)O11Z1、R21Z1、R31Z1、R41Z1、R51Z1、R61Z1And R71Z1Respectively, R in the formula (IZ1)O1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1Is superior toThe same example was chosen.
In the formula (IZI-B), (mode 1) R1Z1、R61Z1And R71Z1Is preferably a hydrogen atom. In addition, (mode 2) RO11Z1It is also preferable that the hydrocarbon group is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. Further, (mode 3) R21Z1、R31Z1、R41Z1And R51Z1It is also preferred that at least one of them is nitro or tert-butyl. The above-mentioned modes 1 to 3 can be adopted individually, or they can be combined appropriately.
Specific examples of the compound IZ1 include compounds IZ1-1 to IZ1-529 and alkali metal salts thereof having a substituent shown in table 1Z1, table 2Z1, table 3Z1, table 4Z1, table 5Z1, table 6Z1, table 7Z1, table 10Z1, table 11Z1, table 12Z1 and table 13Z1 in formula (IZ 1-aa).
Ba1Z1Ba2Z1The partial structure represented by any one of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) is shown. As Ba1Z1Ba2Z1Formula (BB1), formula (BB6), formula (BB8), formula (BB11), formula (BB14), formula (BB19), formula (BB37), formula (BB58), formula (BBJ2), formula (BBO8), and formula (BBO10) are preferable, and formula (BB1), formula (BB6), and formula (BB19) are more preferable.
Figure BDA0003121580680000711
Each symbol in table 1Z1, table 2Z1, table 3Z1, table 4Z1, table 5Z1, table 6Z1, table 7Z1, table 10Z1, table 11Z1, table 12Z1, and table 13Z1 represents the following partial structure. In the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group,
"TBu" means t-butyl, "Hex" means hexyl, "Oct" means octyl,
"2 EH" represents 2-ethylhexyl, "CHM" represents cyclohexylmethyl, "CH" represents cyclohexyl, "PH" represents phenyl, "BZ" represents benzyl, "NPR" represents propyl,
"IPR" represents isopropyl, "IBu" represents isobutyl, and "EOE" represents-CH2CH2OCH2CH3"ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents-CO-CH3And "COE" represents-COO-CH2CH3And "OCM" represents-OCO-CH3And "OME" represents-O-CH3"SOT" represents a tosyl group, and "SNH" represents-SO2NH-CH2CH(CH2CH3)((CH2)3CH3) "SN 2" represents-SO2N(CH3)((CH2)7CH3) "CNM" represents-CONHCH3And "CN 2" represents-CON (CH)3)C6H5And "NPH" represents-NHC6H5
"NOT" means-N ((CH)2)7CH3)2And "NCO" represents-NHCO ((CH)2)4CH3) "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO 2" represents a nitro group, and "SUA" represents-SO3H, "CBA" means-CO2H, "CHO" means-CHO, "OCH" means-OCOH, "OH" means-OH, "SFM" means-SO2NH2"CBM" represents-CONH2"NH 2" means-NH2"NCH" represents-nhcooh, and represents a chemical bond.
Figure BDA0003121580680000721
Figure BDA0003121580680000731
Figure BDA0003121580680000741
Ba1Z1And Ba2Z1Each represents a chemical bond, Ba1Z1Is as follows B1When a chemical bond of (A) is present, Ba2Z1B is as follows2The chemical bond of (a); b isa1Z1Is as follows B2When a chemical bond of (A) is present, Ba2Z1B is as follows1The chemical bond of (1).
Figure BDA0003121580680000751
Figure BDA0003121580680000761
Figure BDA0003121580680000771
[ Table 1Z1]
TABLE 1Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-1 H BB1 H H H
IZ1-2 Me BB1 H H H
IZ1-3 Et BB1 H H H
IZ1-4 Bu BB1 H H H
IZ1-5 TBu BB1 H H H
IZ1-6 Hex BB1 H H H
IZ1-7 Oct BB1 H H H
IZ1-8 2EH BB1 H H H
IZ1-9 CHM BB1 H H H
IZ1-10 CH BB1 H H H
IZ1-11 PH BB1 H H H
IZ1-12 BZ BB1 H H H
IZ1-13 NPR BB1 H H H
IZ1-14 IPR BB1 H H H
IZ1-15 IBu BB1 H H H
IZ1-16 EOE BB1 H H H
IZ1-17 ALL BB1 H H H
IZ1-18 HYE BB1 H H H
IZ1-19 H BB6 H H H
IZ1-20 Me BB6 H H H
IZ1-21 Et BB6 H H H
IZ1-22 Bu BB6 H H H
IZ1-23 TBu BB6 H H H
IZ1-24 Hex BB6 H H H
IZ1-25 Oct BB6 H H H
IZ1-26 2EH BB6 H H H
IZ1-27 CHM BB6 H H H
IZ1-28 CH BB6 H H H
IZ1-29 PH BB6 H H H
IZ1-30 BZ BB6 H H H
IZ1-31 NPR BB6 H H H
IZ1-32 IPR BB6 H H H
IZ1-33 IBu BB6 H H H
IZ1-34 EOE BB6 H H H
IZ1-35 ALL BB6 H H H
IZ1-36 HYE BB6 H H H
IZ1-37 H BB19 H H H
IZ1-38 Me BB19 H H H
IZ1-39 Et BB19 H H H
IZ1-40 Bu BB19 H H H
[ Table 2Z1]
TABLE 2Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-41 TBu BB19 H H H
IZ1-42 Hex BB19 H H H
IZ1-43 Oct BB19 H H H
IZ1-44 2EH BB19 H H H
IZ1-45 CHM BB19 H H H
IZ1-46 CH BB19 H H H
IZ1-47 PH BB19 H H H
IZ1-48 BZ BB19 H H H
IZ1-49 NPR BB19 H H H
IZ1-50 IPR BB19 H H H
IZ1-51 IBu BB19 H H H
IZ1-52 EOE BB19 H H H
IZ1-53 ALL BB19 H H H
IZ1-54 HYE BB19 H H H
IZ1-55 H BB2 H H H
IZ1-56 Me BB3 H H H
IZ1-57 Et BB4 H H H
IZ1-58 Bu BB5 H H H
IZ1-59 TBu BB7 H H H
IZ1-60 Hex BB8 H H H
IZ1-61 Oct BB9 H H H
IZ1-62 2EH BB10 H H H
IZ1-63 CHM BB11 H H H
IZ1-64 CH BB12 H H H
IZ1-65 PH BB13 H H H
IZ1-66 BZ BB14 H H H
IZ1-67 NPR BB15 H H H
IZ1-68 IPR BB16 H H H
IZ1-69 IBu BB17 H H H
IZ1-70 EOE BB18 H H H
IZ1-71 ALL BB20 H H H
IZ1-72 HYE BB21 H H H
IZ1-73 H BB22 H H H
IZ1-74 Me BB23 H H H
IZ1-75 Et BB24 H H H
IZ1-76 Bu BB25 H H H
IZ1-77 TBu BB26 H H H
IZ1-78 Hex BB27 H H H
IZ1-79 Oct BB28 H H H
IZ1-80 2EH BB29 H H H
[ Table 3Z1]
TABLE 3Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-81 CHM BB30 H H H
IZ1-82 CH BB31 H H H
IZ1-83 PH BB32 H H H
IZ1-84 BZ BB33 H H H
IZ1-85 NPR BB34 H H H
IZ1-86 IPR BB35 H H H
IZ1-87 IBu BB36 H H H
IZ1-88 EOE BB37 H H H
IZ1-89 ALL BB38 H H H
IZ1-90 HYE BB39 H H H
IZ1-91 H BB40 H H H
IZ1-92 Me BB41 H H H
IZ1-93 Et BB42 H H H
IZ1-94 Bu BB43 H H H
IZ1-95 TBu BB44 H H H
IZ1-96 Hex BB45 H H H
IZ1-97 Oct BB46 H H H
IZ1-98 2EH BB47 H H H
IZ1-99 CHM BB48 H H H
IZ1-100 CH BB49 H H H
IZ1-101 PH BB50 H H H
IZ1-102 BZ BB51 H H H
IZ1-103 NPR BB52 H H H
IZ1-104 IPR BB53 H H H
IZ1-105 IBu BB54 H H H
IZ1-106 EOE BB55 H H H
IZ1-107 ALL BB56 H H H
IZ1-108 HYE BB57 H H H
IZ1-109 H BB58 H H H
IZ1-110 Me BB59 H H H
IZ1-111 Et BB60 H H H
IZ1-112 Et BB1 H Me Me
IZ1-113 Bu BB2 H CH CH
IZ1-114 TBu BB3 H BZ H
IZ1-115 Hex BB4 Me Me Me
IZ1-116 H BB5 Et CH CH
IZ1-117 Me BB6 H Et Et
IZ1-118 Et BB7 H Bu Bu
IZ1-119 Bu BB8 H TBu TBu
IZ1-120 TBu BB9 H Hex Hex
[ Table 4Z1]
TABLE 4Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-121 Hex BB10 H Oct Oct
IZ1-122 Oct BB11 H 2EH 2EH
IZ1-123 2EH BB12 H CHM CHM
IZ1-124 CHM BB13 H PH PH
IZ1-125 CH BB14 H BZ BZ
IZ1-126 PH BB15 H NPR NPR
IZ1-127 BZ BB16 H IPR IPR
IZ1-128 NPR BB17 H IBu IBu
IZ1-129 IPR BB18 H EOE EOE
IZ1-130 IBu BB19 H ALL ALL
IZ1-131 EOE BB20 H NH2 NH2
IZ1-132 ALL BB21 H CBM CBM
IZ1-133 HYE BB22 H COM COM
IZ1-134 H BB23 H COE COE
IZ1-135 Me BB24 H CBA CBA
IZ1-136 Et BB25 H HYE HYE
IZ1-137 Bu BB26 H Me Me
IZ1-138 TBu BB27 H CH CH
IZ1-139 Hex BB28 H BZ H
IZ1-140 Oct BB29 Me Me Me
IZ1-141 2EH BB30 Et CH CH
IZ1-142 CHM BB31 H Et Et
IZ1-143 CH BB32 H Bu Bu
IZ1-144 PH BB33 H TBu TBu
IZ1-145 BZ BB34 H Hex Hex
IZ1-146 NPR BB35 H Oct Oct
IZ1-147 IPR BB36 H 2EH 2EH
IZ1-148 IBu BB37 H CHM CHM
IZ1-149 EOE BB38 H PH PH
IZ1-150 ALL BB39 H BZ BZ
IZ1-151 HYE BB40 H NPR NPR
IZ1-152 H BB41 H IPR IPR
IZ1-153 Me BB42 H IBu IBu
IZ1-154 Et BB43 H EOE EOE
IZ1-155 Bu BB44 H ALL ALL
IZ1-156 TBu BB45 H NH2 NH2
IZ1-157 Hex BB46 H CBM CBM
IZ1-158 Oct BB47 H COM COM
IZ1-159 2EH BB48 H COE COE
IZ1-160 CHM BB49 H CBA CBA
[ Table 5Z1]
TABLE 5Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-161 CH BB50 H HYE HYE
IZ1-162 PH BB51 H Me Me
IZ1-163 BZ BB52 H CH CH
IZ1-164 NPR BB53 H BZ H
IZ1-165 IPR BB54 Me Me Me
IZ1-166 IBu BB55 Et CH CH
IZ1-167 EOE BB56 H Et Et
IZ1-168 ALL BB57 H Bu Bu
IZ1-169 HYE BB58 H TBu TBu
IZ1-170 H BB59 H Hex Hex
IZ1-171 Me BB60 H Oct Oct
IZ1-172 CHM BB1 Me H H
IZ1-173 CH BB2 COM H H
IZ1-174 PH BB3 COE H H
IZ1-175 BZ BB4 Et H H
IZ1-176 NPR BB5 OCM H H
IZ1-177 IPR BB6 OME H H
IZ1-178 IBu BB7 Bu H H
IZ1-179 EOE BB8 SOT H H
IZ1-180 ALL BB9 SNH H H
IZ1-181 HYE BB10 TBu H H
IZ1-182 H BB11 SN2 H H
IZ1-183 Me BB12 CNM H H
IZ1-184 Et BB13 Hex H H
IZ1-185 Bu BB14 CN2 H H
IZ1-186 TBu BB15 NPH H H
IZ1-187 Hex BB16 Oct H H
IZ1-188 Oct BB17 NOT H H
IZ1-189 2EH BB18 NCO H H
IZ1-190 CHM BB19 2EH H H
IZ1-191 CH BB20 F H H
IZ1-192 PH BB21 Cl H H
IZ1-193 BZ BB22 CHM H H
IZ1-194 NPR BB23 Br H H
IZ1-195 IPR BB24 CN H H
IZ1-196 IBu BB25 CH H H
IZ1-197 EOE BB26 NO2 H H
IZ1-198 ALL BB27 SUA H H
IZ1-199 HYE BB28 PH H H
IZ1-200 H BB29 CBA H H
[ Table 6Z1]
TABLE 6Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-201 Me BB30 CHO H H
IZ1-202 Et BB31 BZ H H
IZ1-203 Bu BB32 OCH H H
IZ1-204 TBu BB33 NPR H H
IZ1-205 Hex BB34 OH H H
IZ1-206 Oct BB35 IPR H H
IZ1-207 2EH BB36 SFM H H
IZ1-208 CHM BB37 IBu H H
IZ1-209 CH BB38 CBM H H
IZ1-210 PH BB39 EOE H H
IZ1-211 BZ BB40 NH2 H H
IZ1-212 NPR BB41 ALL H H
IZ1-213 IPR BB42 NCH H H
IZ1-214 IBu BB43 HYE H H
IZ1-215 EOE BB44 H Me H
IZ1-216 ALL BB45 H H COM
IZ1-217 HYE BB46 H COE H
IZ1-218 H BB47 H H Et
IZ1-219 Me BB48 H OCM H
IZ1-220 Et BB49 H H OME
IZ1-221 Bu BB50 H Bu H
IZ1-222 TBu BB51 H H SOT
IZ1-223 Hex BB52 H SNH H
IZ1-224 Oct BB53 H H TBu
IZ1-225 2EH BB54 H SN2 H
IZ1-226 CHM BB55 H H CNM
IZ1-227 CH BB56 H Hex H
IZ1-228 PH BB57 H H CN2
IZ1-229 BZ BB58 H NPH H
IZ1-230 NPR BB59 H H Oct
IZ1-231 IPR BB60 H NOT H
IZ1-232 IBu BB1 H H NCO
IZ1-233 EOE BB2 H 2EH H
IZ1-234 ALL BB3 H H F
IZ1-235 HYE BB4 H Cl H
IZ1-236 H BB5 H H CHM
IZ1-237 Me BB6 H Br H
IZ1-238 Et BB7 H H CN
IZ1-239 Bu BB8 H CH H
IZ1-240 TBu BB9 H H NO2
[ Table 7Z1]
TABLE 7Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-241 Hex BB10 H SUA H
IZ1-242 Oct BB11 H H PH
IZ1-243 2EH BB12 H CBA H
IZ1-244 CHM BB13 H H CHO
IZ1-245 CH BB14 H BZ BZ
IZ1-246 PH BB15 H H OCH
IZ1-247 BZ BB16 H NPR H
IZ1-248 NPR BB17 H H OH
IZ1-249 IPR BB18 H IPR H
IZ1-250 IBu BB19 H H SFM
IZ1-251 EOE BB20 H IBu H
IZ1-252 ALL BB21 H H CBM
IZ1-253 HYE BB22 H EOE H
IZ1-254 H BB23 H H NH2
IZ1-255 Me BB24 H ALL H
IZ1-256 Et BB25 H H NCH
IZ1-257 Bu BB26 H HYE H
IZ1-258 Me BB8 H H H
[ Table 10Z1]
TABLE 10Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1 RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-259 NA1 BB1 H H H IZ1-299 H BB11 H H H
IZ1-260 HHk8 BB1 H H H IZ1-300 Me BB11 H H H
IZ1-261 NA2 BB1 H H H IZ1-301 Et BB11 H H H
IZ1-262 HHk7 BB1 H H H IZ1-302 Bu BB11 H H H
IZ1-263 HH37 BB1 H H H IZ1-303 TBu BB11 H H H
IZ1-264 HHk6 BB1 H H H IZ1-304 Hex BB11 H H H
IZ1-265 NA3 BB1 H H H IZ1-305 Oct BB11 H H H
IZ1-266 HHJ2 BB1 H H H IZ1-306 2EH BB11 H H H
IZ1-267 HHk11 BB1 H H H IZ1-307 CH BB11 H H H
IZ1-268 NA1 BB6 H H H IZ1-308 PH BB11 H H H
IZ1-269 HHk8 BB6 H H H IZ1-309 BZ BB11 H H H
IZ1-270 NA2 BB6 H H H IZ1-310 EOE BB11 H H H
IZ1-271 HHk7 BB6 H H H IZ1-311 ALL BB11 H H H
IZ1-272 HH37 BB6 H H H IZ1-312 HYE BB11 H H H
IZ1-273 HHk6 BB6 H H H IZ1-313 NA1 BB11 H H H
IZ1-274 NA3 BB6 H H H IZ1-314 HHk8 BB11 H H H
IZ1-275 HHJ2 BB6 H H H IZ1-315 NA2 BB11 H H H
IZ1-276 HHk11 BB6 H H H IZ1-316 HHk7 BB11 H H H
IZ1-277 H BB8 H H H IZ1-317 HH37 BB11 H H H
IZ1-278 Et BB8 H H H IZ1-318 HHk6 BB11 H H H
IZ1-279 Bu BB8 H H H IZ1-319 NA3 BB11 H H H
IZ1-280 TBu BB8 H H H IZ1-320 HHJ2 BB11 H H H
IZ1-281 Oct BB8 H H H IZ1-321 HHk11 BB11 H H H
IZ1-282 2EH BB8 H H H IZ1-322 H BB14 H H H
IZ1-283 CHM BB8 H H H IZ1-323 Me BB14 H H H
IZ1-284 CH BB8 H H H IZ1-324 Et BB14 H H H
IZ1-285 PH BB8 H H H IZ1-325 Bu BB14 H H H
IZ1-286 BZ BB8 H H H IZ1-326 TBu BB14 H H H
IZ1-287 EOE BB8 H H H IZ1-327 Hex BB14 H H H
IZ1-288 ALL BB8 H H H IZ1-328 Oct BB14 H H H
IZ1-289 HYE BB8 H H H IZ1-329 2EH BB14 H H H
IZ1-290 NA1 BB8 H H H IZ1-330 CHM BB14 H H H
IZ1-291 HHk8 BB8 H H H IZ1-331 CH BB14 H H H
IZ1-292 NA2 BB8 H H H IZ1-332 PH BB14 H H H
IZ1-293 HHk7 BB8 H H H IZ1-333 EOE BB14 H H H
IZ1-294 HH37 BB8 H H H IZ1-334 ALL BB14 H H H
IZ1-295 HHk6 BB8 H H H IZ1-335 HYE BB14 H H H
IZ1-296 NA3 BB8 H H H IZ1-336 NA1 BB14 H H H
IZ1-297 HHJ2 BB8 H H H IZ1-337 HHk8 BB14 H H H
IZ1-298 HHk11 BB8 H H H IZ1-338 NA2 BB14 H H H
[ Table 11Z1]
TABLE 11Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1 RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-339 HHk7 BB14 H H H IZ1-379 Bu BB58 H H H
IZ1-340 HH37 BB14 H H H IZ1-380 TBu BB58 H H H
IZ1-341 HHk6 BB14 H H H IZ1-381 Hex BB58 H H H
IZ1-342 NA3 BB14 H H H IZ1-382 Oct BB58 H H H
IZ1-343 HHJ2 BB14 H H H IZ1-383 2EH BB58 H H H
IZ1-344 HHk11 BB14 H H H IZ1-384 CHM BB58 H H H
IZ1-345 NA1 BB19 H H H IZ1-385 CH BB58 H H H
IZ1-346 HHk8 BB19 H H H IZ1-386 PH BB58 H H H
IZ1-347 NA2 BB19 H H H IZ1-387 BZ BB58 H H H
IZ1-348 HHk7 BB19 H H H IZ1-388 EOE BB58 H H H
IZ1-349 HH37 BB19 H H H IZ1-389 ALL BB58 H H H
IZ1-350 HHk6 BB19 H H H IZ1-390 HYE BB58 H H H
IZ1-351 NA3 BB19 H H H IZ1-391 NA1 BB58 H H H
IZ1-352 HHJ2 BB19 H H H IZ1-392 HHk8 BB58 H H H
IZ1-353 HHk11 BB19 H H H IZ1-393 NA2 BB58 H H H
IZ1-354 H BB37 H H H IZ1-394 HHk7 BB58 H H H
IZ1-355 Me BB37 H H H IZ1-395 HH37 BB58 H H H
IZ1-356 Et BB37 H H H IZ1-396 HHk6 BB58 H H H
IZ1-357 Bu BB37 H H H IZ1-397 NA3 BB58 H H H
IZ1-358 TBu BB37 H H H IZ1-398 HHJ2 BB58 H H H
IZ1-359 Hex BB37 H H H IZ1-399 HHk11 BB58 H H H
IZ1-360 Oct BB37 H H H IZ1-400 H BBJ2 H H H
IZ1-361 2EH BB37 H H H IZ1-401 Me BBJ2 H H H
IZ1-362 CHM BB37 H H H IZ1-402 Et BBJ2 H H H
IZ1-363 CH BB37 H H H IZ1-403 Bu BBJ2 H H H
IZ1-364 PH BB37 H H H IZ1-404 TBu BBJ2 H H H
IZ1-365 BZ BB37 H H H IZ1-405 Hex BBJ2 H H H
IZ1-366 ALL BB37 H H H IZ1-406 Oct BBJ2 H H H
IZ1-367 HYE BB37 H H H IZ1-407 2EH BBJ2 H H H
IZ1-368 NA1 BB37 H H H IZ1-408 CHM BBJ2 H H H
IZ1-369 HHk8 BB37 H H H IZ1-409 CH BBJ2 H H H
IZ1-370 NA2 BB37 H H H IZ1-410 PH BBJ2 H H H
IZ1-371 HHk7 BB37 H H H IZ1-411 BZ BBJ2 H H H
IZ1-372 HH37 BB37 H H H IZ1-412 EOE BBJ2 H H H
IZ1-373 HHk6 BB37 H H H IZ1-413 ALL BBJ2 H H H
IZ1-374 NA3 BB37 H H H IZ1-414 HYE BBJ2 H H H
IZ1-375 HHJ2 BB37 H H H IZ1-415 NA1 BBJ2 H H H
IZ1-376 HHk11 BB37 H H H IZ1-416 HHk8 BBJ2 H H H
IZ1-377 Me BB58 H H H IZ1-417 NA2 BBJ2 H H H
IZ1-378 Et BB58 H H H IZ1-418 HHk7 BBJ2 H H H
[ Table 12Z1]
TABLE 12Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1 RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-419 HH37 BBJ2 H H H IZ1-459 BZ BBO10 H H H
IZ1-420 HHk6 BBJ2 H H H IZ1-460 EOE BBO10 H H H
IZ1-421 NA3 BBJ2 H H H IZ1-461 ALL BBO10 H H H
IZ1-422 HHJ2 BBJ2 H H H IZ1-462 HYE BBO10 H H H
IZ1-423 HHk11 BBJ2 H H H IZ1-463 NA1 BBO10 H H H
IZ1-424 H BBO8 H H H IZ1-464 HHk8 BBO10 H H H
IZ1-425 Me BBO8 H H H IZ1-465 NA2 BBO10 H H H
IZ1-426 Et BBO8 H H H IZ1-466 HHk7 BBO10 H H H
IZ1-427 Bu BBO8 H H H IZ1-467 HH37 BBO10 H H H
IZ1-428 TBu BBO8 H H H IZ1-468 HHk6 BBO10 H H H
IZ1-429 Hex BBO8 H H H IZ1-469 NA3 BBO10 H H H
IZ1-430 Oct BBO8 H H H IZ1-470 HHJ2 BBO10 H H H
IZ1-431 2EH BBO8 H H H IZ1-471 HHk11 BBO10 H H H
IZ1-432 CHM BBO8 H H H IZ1-472 HH9 BB2 H H H
IZ1-433 CH BBO8 H H H IZ1-473 HHk7 BB3 H H H
IZ1-434 PH BBO8 H H H IZ1-474 HHk8 BB4 H H H
IZ1-435 BZ BBO8 H H H IZ1-475 HHe4 BB5 H H H
IZ1-436 EOE BBO8 H H H IZ1-476 HHa2 BB7 H H H
IZ1-437 ALL BBO8 H H H IZ1-477 HHj10 BB9 H H H
IZ1-438 HYE BBO8 H H H IZ1-478 HH46 BB10 H H H
IZ1-439 NA1 BBO8 H H H IZ1-479 HHh8 BB12 H H H
IZ1-440 HHk8 BBO8 H H H IZ1-480 HHf5 BB13 H H H
IZ1-441 NA2 BBO8 H H H IZ1-481 HH81 BB15 H H H
IZ1-442 HHk7 BBO8 H H H IZ1-482 HHJ2 BB16 H H H
IZ1-443 HH37 BBO8 H H H IZ1-483 HHk5 BB17 H H H
IZ1-444 HHk6 BBO8 H H H IZ1-484 HH76 BB18 H H H
IZ1-445 NA3 BBO8 H H H IZ1-485 HHJ10 BB20 H H H
IZ1-446 HHJ2 BBO8 H H H IZ1-486 HH13 BB21 H H H
IZ1-447 HHk11 BBO8 H H H IZ1-487 HHJ3 BB22 H H H
IZ1-448 H BBO10 H H H IZ1-488 HHj19 BB23 H H H
IZ1-449 Me BBO10 H H H IZ1-489 NA1 BB24 H H H
IZ1-450 Et BBO10 H H H IZ1-490 HH36 BB25 H H H
IZ1-451 Bu BBO10 H H H IZ1-491 HH49 BB26 H H H
IZ1-452 TBu BBO10 H H H IZ1-492 HH40 BB27 H H H
IZ1-453 Hex BBO10 H H H IZ1-493 NA5 BB28 H H H
IZ1-454 Oct BBO10 H H H IZ1-494 HH37 BB29 H H H
IZ1-455 2EH BBO10 H H H IZ1-495 HH65 BB30 H H H
IZ1-456 CHM BBO10 H H H IZ1-496 HHj17 BB31 H H H
IZ1-457 CH BBO10 H H H IZ1-497 HH35 BB32 H H H
IZ1-458 PH BBO10 H H H IZ1-498 HH43 BB33 H H H
[ Table 13Z1]
TABLE 13Z1
RO1Z1 Ba1Z1Ba2Z1 R1Z1 R6Z1 R7Z1
IZ1-499 HHg2 BB34 H H H
IZ1-500 HHJ4 BB35 H H H
IZ1-501 NA4 BB36 H H H
IZ1-502 HHc1 BB38 H H H
IZ1-503 HHk4 BB39 H H H
IZ1-504 HHk1 BB40 H H H
IZ1-505 HHk3 BB41 H H H
IZ1-506 HHf14 BB42 H H H
IZ1-507 HH34 BB43 H H H
IZ1-508 HHi11 BB44 H H H
IZ1-509 HHh1 BB45 H H H
IZ1-510 HH83 BB46 H H H
IZ1-511 HH78 BB47 H H H
IZ1-512 NA2 BB48 H H H
IZ1-513 HHd6 BB49 H H H
IZ1-514 HH61 BB50 H H H
IZ1-515 HH80 BB51 H H H
IZ1-516 HH28 BB52 H H H
IZ1-517 NA3 BB53 H H H
IZ1-518 HHf11 BB54 H H H
IZ1-519 HH55 BB55 H H H
IZ1-520 HH69 BB56 H H H
IZ1-521 HHk11 BB57 H H H
IZ1-522 HHh4 BB59 H H H
IZ1-523 HHk6 BB60 H H H
IZ1-524 HHb3 BBI1 H H H
IZ1-525 HH58 BBD1 H H H
IZ1-526 HHf1 BBK2 H H H
IZ1-527 HH22 BBK3 H H H
IZ1-528 HHg1 BBK4 H H H
IZ1-529 HHg5 BBK14 H H H
For example, the compound IZ1-1 is a compound represented by the formula (IZ 1-1).
Figure BDA0003121580680000881
As a compound of formula (I) Z1,
preferably a compound IZ1-1 to a compound IZ1-171, a compound IZ1-258 to a compound IZ1-529, more preferably a compound IZ1-1 to a compound IZ1-171, a compound IZ1-258 to a compound IZ1-471,
the compound IZ1-1 to the compound IZ1-171 are more preferable, the compound IZ1-1 to the compound IZ1-111 are still more preferable, the compound IZ1-1 to the compound IZ1-54 are particularly preferable, and the compound IZ1-2 to the compound IZ1-3, the compound IZ1-20 to the compound IZ1-21 and the compound IZ1-38 to the compound IZ1-39 are particularly preferable.
Specific examples of the compound IZ1 include compounds represented by table 1Z1, table 2Z1, table 3Z1, table 4Z1, table 5Z1, table 6Z1, table 7Z1, table 10Z1, table 11Z1, table 12Z1, and table 13Z1 in which 1 to 3 hydrogen atoms contained in the compound are replaced by — SO3M or-CO2M is substituted. For example, compounds having 1 to 3 sulfo groups bonded to the compound IZ1-1 of Table 1Z1 are represented by the following structures. Wherein, in the formula, - (SO)3H) Represents a compound in which any hydrogen atom in compound IZ1-1 of Table 1Z1 is substituted.
Figure BDA0003121580680000891
In the present invention, it is preferable that 1 to 3-SO groups are bonded to the compound IZ1-1 to the compound IZ1-171, the compound IZ1-258 to the compound IZ1-5293M or-CO2More preferably, the compound of M is a compound in which 1 to 3-SO groups are bonded to the compound IZ1-1 to the compound IZ1-171, the compound IZ1-258 to the compound IZ1-4313M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ1-1 to the compound IZ1-1713M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ1-1 to the compound IZ1-1113M or-CO2A compound formed by the reaction of M,
particularly preferably, 1 to 3-SO groups are bonded to the compound IZ1-1 to the compound IZ1-543M or-CO2A compound formed by the reaction of M,
particularly preferably, 1 to 3-SO groups are bonded to the compound IZ1-2 to the compound IZ1-3, the compound IZ1-20 to the compound IZ1-21, and the compound IZ1-38 to the compound IZ1-393M or-CO2M, or a salt thereof.
Figure BDA0003121580680000892
As the compound (IZ1), the following compounds are preferable: in the formula (IZ1), RO1Z1Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R1Z1Is a hydrogen atom and may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO 3M or-CO2M,R2Z1~R5Z1Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z1)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z1、-O-R102Z1、-SO3M or-CO2M,
R6Z1And R7Z1Independently of one another, a hydrogen atom, may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,
R102Z1Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 20 carbon atoms as a substituent in the group consisting of M,
a compound in which M is a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
RO1Z1is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1Z1is a hydrogen atom, and is a hydrogen atom,
R2Z1~R5Z1each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z1)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z1、-O-R102Z1、-SO3M or-CO2M,
R6Z1And R7Z1Are the same radicals, are hydrogenAtoms, or may have radicals selected from-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R102Z1is a hydrogen atom, or may have a radical selected from the group consisting of-SO 3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
a compound in which M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
RO1Z1is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1Z1is a hydrogen atom, and is a hydrogen atom,
R2Z1~R5Z1each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z1)2Nitro, trifluoromethyl, -O-R102Z1、-SO3M or-CO2M,
R6Z1And R7Z1The same group is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms,
R102Z1is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
m is a hydrogen atom or an alkali metal atom.
For compound IZ1, R1Z1In the case of a hydrogen atom, the compound represented by the formula (pt1Z1) (hereinafter, may be referred to as phthalonitrile (phthalonitrile) compound) may be reacted with the compound represented by the formula (pt2Z1) (hereinafter, may be referred to as alkoxide (alkoxide) compound), and then, the compound represented by the formula (pt3Z1) and the compound represented by the formula (pt4Z1) may be further reacted in the presence of an acid. In addition, R1Z1When not a hydrogen atom, the compound is further reacted with a compound represented by the formula (pt5Z1) to produce a compound IZ 1.
Figure BDA0003121580680000911
In [ formula (pt1Z1), formula (pt2Z1), formula (pt3Z1), formula (pt4Z1), formula (pt5Z1) and formula (IZ1), RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1The same meanings as described above are indicated. R14Z1Represents an alkyl group having 1 to 20 carbon atoms. M1Z1Represents an alkali metal atom. LG represents a halogen atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group.]
As R14Z1Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z1Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z1 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z1 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z1, and the compound pt4Z1 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; 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 acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound.
The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z1 used, relative to R1Z1The amount of the compound IZ11 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
In addition, when the compound pt5Z1 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1Z1The amount of the compound IZ11 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
In addition, the reaction of the compound pt5Z1 can be generally carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1Z1The amount of the compound IZ 11 is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z1 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound IZ1 having no sulfo group or-SO3M22In the case of (3), the compound IZ1 can be reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to introduce a sulfo group or-SO3M2
M22Represents an alkali metal atom.
As M22Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
With respect to SO in oleum3The amount of (b) is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and still more preferably 5 to 25 mol based on 11 mol of the compound IZ.
The amount of sulfuric acid used in the oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on 11 moles of the compound IZ.
The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on 11 moles of the compound IZ.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound IZ1 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is filtered to extract the compound IZ 1. Further, the residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After the completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
< Compound IZ2 >)
Compound IZ2 is a compound represented by formula (IZ 2).
Figure BDA0003121580680000941
[ in the formula (IZ2),
RCO1Z2and RCO2Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2
RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2And R5Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2Each of which may be bonded to each other to form a ring. R101Z2The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. RO1Z2And R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom.
RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The number of carbon atoms of the optionally substituted hydrocarbon group is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and particularly preferably 1 to 5.
RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentylBranched alkyl groups such as a tert-pentyl group, a (1-methyl) pentyl group, a (2-methyl) pentyl group, a (1-ethyl) pentyl group, a (3-ethyl) pentyl group, an isohexyl group, a (5-methyl) hexyl group, a (2-ethyl) hexyl group, and a (3-ethyl) heptyl group; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, further more preferably 1 to 8, and particularly preferably 1 to 5. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable, and a methyl group, an ethyl group, and a tert-butyl group are particularly preferable.
As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, and, Cycloalkyl groups such as 2,2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl group, and the like are particularly preferable, Cyclohexyl, cycloheptyl, cyclooctyl.
As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a mesityl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a, Aromatic hydrocarbon groups such as 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracyl, pyrenyl and the like; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2As the group represented, a group obtained by combining the above-mentioned hydrocarbon groups (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group) may be mentionedExamples of the alkyl group include an alkyl group to which 1 or more alicyclic hydrocarbon groups are bonded, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, and an adamantylmethyl group.
The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group represented may have a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, and a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
Figure BDA0003121580680000981
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl;
a formyl group;
a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
Figure BDA0003121580680000991
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
Figure BDA0003121580680000992
Figure BDA0003121580680001001
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formulae;
Figure BDA0003121580680001011
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, and N, N-phenylmethylsulfamoyl);
Figure BDA0003121580680001021
Figure BDA0003121580680001031
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
Figure BDA0003121580680001032
Figure BDA0003121580680001041
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is an alkali metal, preferably lithium, sodium, potassium); a nitro group; a cyano group;
a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
Figure BDA0003121580680001042
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
Figure BDA0003121580680001051
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
Figure BDA0003121580680001061
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, and a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3and-CO-S-CH2-CH2-CH2-CH3Or a thiocarbonyl group, -CO-S-C, bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) 6H5A thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms;
a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
Figure BDA0003121580680001071
-NRCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereofA group derived from a percarboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like), wherein R's may be the same or different from each other, and may be bonded to each other to form a ring);
Figure BDA0003121580680001081
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
Figure BDA0003121580680001091
A group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
Figure BDA0003121580680001101
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereofA group derived from a percarboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like), wherein R's may be the same or different from each other, and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR3(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring); and so on.
Examples of the substituent having a valence of 2 include an oxo group, a thioxo 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. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom;
-CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms;
a hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
An amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof;
a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
a hydroxyl group; fluorine atom, chlorine atom, bromine atom;
-CO2m (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom);
-SO3m (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group;
a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group having 1 to 40 carbon atoms and having a substituent represented by the formula (I) includes a hydrocarbon group having 1 to 40 carbon atoms and having a substituent having a valence of 1 or 2, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, and a group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which are a combination of hydrocarbon groups,
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups having 1 to 20 carbon atoms having a substituent of group s1,
particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 1 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The heterocyclic group represented by (a) may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like. The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include:
monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole;
a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine;
a fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane; bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone; five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran; fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole, chroman and isochroman; fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include:
five-membered ring system saturated heterocycles such as dithiolane;
saturated heterocyclic rings of six-membered ring systems such as thiacyclohexane, 1, 3-dithiane, 2-methyl-1, 3-dithiane and the like;
a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran);
fused bicyclic heterocycles such as benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include:
monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone; a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole);
fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a group obtained by combining the hydrocarbon groups listed above, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
Figure BDA0003121580680001141
The above heterocyclic group may be R1Z2~R5Z22 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1Z2~R5Z2The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
Figure BDA0003121580680001151
The bonding position of the heterocycle is a portion where any hydrogen atom contained in each ring is removed.
RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The heterocyclic group represented may have a substituent. Examples of the substituent includeO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group may have the same substituent as the substituent. In addition, in the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom.
Preferred examples of the substituent includeO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The preferable examples of the substituents which the hydrocarbon group may have are the same. As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The heterocyclic group having a substituent represented by the formula (i) includes a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s 2.
The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2Of (a) is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, -SO3M、-CO2M is explained.
as-CO-R102Z2Examples thereof include a formyl group; a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, or a halogen group (preferably 1 to 20 carbon atoms) is bonded to a group represented by the above formula or the like (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, or a halogen group is bonded to a group represented by the above formula)Chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like) and a carbonyl group (having 2 to 41 carbon atoms when the carbonyl group is an acyl group) corresponding to-CO-R in the compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2102Z2Preferable examples of the group(s) include a carbonyl group (more preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and compounds shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2 correspond to-CO-R 102Z2And the like.
as-COO-R101Z2Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl and heptyloxycarbonyl, an oxycarbonyl group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group, an eicosyloxycarbonyl group and the like, and the groups represented by the above chemical formulae, and the compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 correspond to-COO-R.101Z2Preferred examples of the group (b) include oxycarbonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 which correspond to-COO-R101Z2And the like.
as-OCO-R102Z2Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy A carbonyloxy group (having 2 to 41 carbon atoms when the carbonyloxy group is an acyloxy group) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded to a group represented by the above chemical formula, or the like, and a compound represented by table 1Z2 to table 22Z2 and table 27Z2 to table 37Z2 corresponds to-OCO-R102Z2Preferable examples of the group(s) include a carbonyloxy group (more preferably 2 to 12 carbon atoms when the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 corresponds to-OCO-R102Z2And the like.
as-COCO-R102Z2Examples thereof include methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) hexyloxalyl, heptyloxalyl, octyloxalyl, nonyloxalyl, an oxalyl group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) is bonded, such as decyl oxalyl group, undecyloxalyl group, dodecyl oxalyl group, eicosyl oxalyl group, cyclopentyl oxalyl group, cyclohexyl oxalyl group, phenyl oxalyl group, p-tolyloxalyl group, and the group represented by the above chemical formula), and compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 correspond to — COCO — R. 102Z2And the like.
as-O-R102Z2Examples of the group include a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxyA group, an eicosyloxy group, a 1-phenylethoxy group, a 1-methyl-1-phenylethoxy group, a phenyloxy group, a 2, 3-dimethylphenyloxy group, a 2, 4-dimethylphenyloxy group, a 2, 5-dimethylphenyloxy group, a 2, 6-dimethylphenyloxy group, a 3, 4-dimethylphenyloxy group, a 3, 5-dimethylphenyloxy group, a 2, 2-dicyanophenyloxy group, a 2, 3-dicyanophenyloxy group, a 2, 4-dicyanophenyloxy group, a 2, 5-dicyanophenyloxy group, a 2, 6-dicyanophenyloxy group, a 3, 4-dicyanophenyloxy group, a 3, 5-dicyanophenyloxy group, a 4-methoxyphenyloxy group, a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a, An oxy group having a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the above chemical formula, and compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2, which correspond to-O-R 102Z2Preferred examples of the group (b) include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2, which correspond to-O-R102Z2And the like.
as-SO2-R101Z2Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl) hexylsulfonyl, heptylsulfonyl, octylsulfonyl, nonyl sulfonyl group, decyl sulfonyl group, undecyl sulfonyl group, dodecyl sulfonyl group, eicosyl sulfonyl group, phenyl sulfonyl group, p-tolyl sulfonyl group, and the like, and sulfonyl groups in which a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (a derivative thereof such as carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octyl sulfamoyl group) is bonded, such as the group represented by the above chemical formula), and-SO corresponds to the compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z 2.2-R101Z2Preferable examples of the group (b) include sulfonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds represented by tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2, which correspond to-SO 2-R101Z2And the like.
as-SO2N(R102Z2)2Examples thereof include: a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl, N-phenylsulfamoyl, etc., and a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula, or a derivative thereof Sulfamoyl substituted with a raw group (e.g., a group derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), etc.), and compounds represented by tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2, which correspond to-SO2NH(R102Z2X)(R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above), etc.; n, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylsulfamoyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diethylsulfamoyl, N, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl Sulfamoyl groups substituted with 2 hydrocarbon groups having 1 to 40 (preferably 1 to 20) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl groups, sulfo groups, nitro groups, hydroxyl groups, halogens (preferably chlorine atoms), alkylsulfamoyl groups having 1 to 10 carbon atoms (preferably octylsulfamoyl groups), and the like, such as a group represented by the above chemical formula, N-undecylmethylsulfamoyl group, N-dodecylmethylsulfamoyl group, N-eicosylmethylsulfamoyl group, N-phenylmethylsulfamoyl group, N-diphenylsulfamoyl group, and the like, and the sulfamoyl groups corresponding to-SO-in the compounds represented by tables 1Z2 to 22Z2 and 27Z2 to 37Z2, and the like2N(R102Z2X)2(wherein, R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above) and the like,
preferred examples thereof include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof, and compounds represented by tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2, which correspond to-SO2N(R102Z2)2And the like.
as-CON (R)102Z2)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-decylcarbamoyl, N-undecylcarbamoyl, N-dodecylcarbamoyl, N-eicosylcarbamoyl, N-phenylcarbamoyl and the like, Carbamoyl groups substituted with a 1-40 (preferably 1-20) carbon hydrocarbon group or a derivative thereof (e.g., a derivative derived from a carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), 1-10 carbon alkylsulfamoyl group (preferably octylsulfamoyl group)), such as the group represented by the above formula, and The compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 correspond to-CONH (R)102Z2X) (wherein, R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above), etc.;
n, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-tert-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-diethylcarbamoyl group, N-diisopropylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-isobutylcarbamoyl group, N-di (s-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-di-N-butylcarbamoyl group, N, a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, an N, N-di (2-ethyl) hexylcarbamoyl group, an N, N-diheptylcarbamoyl group, an N, N-octylmethylcarbamoyl group, an N, N-dinonylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, an N, N-diphenylcarbamoyl group, etc., and a group represented by the above chemical formula, A carbamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and a compound represented by any one of tables 1Z2 to 22Z2, 27Z2 to 37Z2, wherein-CON (R) is the equivalent of 102Z2X)2(wherein, R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z2 to 22Z2 and 27Z2 to 37Z2 which corresponds to-CON (R)102Z2)2And the like.
as-N (R)102Z2)2Examples thereof include:
an amino group;
a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom)), such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, an N-tert-butylamino group, an N-pentylamino group, an N-hexylamino group, an N- (2-ethyl) hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-undecylamino group, an N-dodecylamino group, an N-eicosylamino group, an N-phenylamino group, and the like, and a group represented by the above chemical formula, A group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like) and a compound shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2, wherein the compound corresponds to-NH (R 102Z2X) (wherein, R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above), etc.;
n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-dipentylamino group, N-bis (1-ethylpropyl) amino group, N-dihexylamino group, N-bis (2-ethyl) hexylamino group, N-diheptylamino group, N-dioctylamino group, N, amino groups substituted with 2 hydrocarbon groups having 1 to 40 (preferably 1 to 20) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl) and the like), such as N-dinonylamino, N-decylmethylamino, N-undecylmethylamino, N-dodecylmethylamino, N-eicosylmethylamino, N-phenylmethylamino, N-diphenylamino and the like, and groups represented by the above chemical formulae, and amino groups represented by the above formulae, and tables 1Z2 to 22Z2 and 27Z 2 2 to the compounds shown in Table 37Z2 corresponding to-N (R)102Z2X)2(wherein, R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above) and the like,
preferred examples thereof include amino groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2, which correspond to-N (R)102Z2)2And the like.
as-NHCO-R102Z2Examples thereof include formylamino; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecanoylamino, dodecanoylamino, heneicosanoylamino, benzoylamino and the like, carbonylamino (for example, in the case where the carbonylamino is an acylamino group, the carbon number is 1 to 40), carbonylamino to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as a group represented by the above formula) and carbonylamino groups having 1 to 40 carbon atoms among the compounds represented by tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 correspond to-NHCO- R 102Z2And the like,
preferred examples thereof include carbonylamino groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded (in the case where the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10), and compounds represented by tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2, which correspond to-NHCO-R102Z2And the like.
as-NHCON (R)102Z2)2Examples thereof include the groups listed above and the compounds shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2 which correspond to-NHCON (R)102Z2)2And the like.
as-NHCOOR102Z2Examples thereof include the groups listed above and those shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2Corresponding to-NHCOOR in the compound102Z2And the like.
as-OCON (R)102Z2)2Examples thereof include those corresponding to-OCON (R) among the above-mentioned groups and the compounds shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2102Z2)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M in M is a hydrogen atom; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102Z2、-COO-R102Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R102Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCON(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
R2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 2). As R2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, and benzo [9,10 ] ene]Phenanthrene, pyrene,
Figure BDA0003121580680001231
Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide and butachlor, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, etc.); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,
Figure BDA0003121580680001232
Nitrogen-containing fused heterocycles such as pyridine, phenanthroline, and phenazine, and partial reductants thereof; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2In the case of forming a ring, the ring may have a substituent. Examples of the substituent include O1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent includeO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3Z2And R4Z2When forming a ring, as R2Z2And R5Z2Independently of one another, hydrogen atoms, amino groups and hydroxyl groups are preferred.
R2Z2And R3Z2When a ring is formed, R is preferably4Z2And R5Z2Does not form a ring, more preferably R4Z2And R5Z2Is a hydrogen atom.
R4Z2And R5Z2When a ring is formed, R is preferably2Z2And R3Z2Does not form a ring, more preferably R2Z2And R3Z2Is a hydrogen atom. R1Z2Preferably a hydrogen atom. RO1Z2The hydrocarbon group is preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, and particularly preferably a hydrogen atom, a methyl group or an ethyl group.
RN1Z2And RN2Z2Preferably a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-CON(R102Z2)2、-N(R102Z2)2、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, still more particularly preferably a hydrogen atom, a methyl group, an ethyl group or a phenyl group, and most preferably a hydrogen atom, a methyl group or an ethyl group. In addition, R N1Z2And RN2Z2The groups may be the same or different, but preferably the same.
From the viewpoint of reducing the retardation value of the color filter formed from the colored composition, R is preferable2Z2、R3Z2、R4Z2、R5Z2At least one of which is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, more preferably a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a halogen atom, -N (R)102Z2)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z2、-O-R102Z2、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Alternatively, R is preferred2Z2And R3Z2、R3Z2And R4Z2Or R4Z2And R5Z2Form a ring.
From the viewpoint of reducing the retardation value of the color filter formed from the colored composition, R is preferable2Z2、R3Z2、R4Z2、R5Z2At least one of which is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, or-N (R)102Z2)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102Z2、-O-R102Z2、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and further preferably a nitro group or a tert-butyl group. Among them, R is more preferable3Z2Is nitro or tert-butyl, R2Z2、R4Z2And R5Z2Is a hydrogen atom; or, R2Z2、R3Z2And R5Z2Is a hydrogen atom, R4Z2Is nitro or tert-butyl.
The compound IZ2 is preferably a compound represented by the formula (IZ2-B) (hereinafter, may be referred to as a compound IZ 2-B.). When the compound IZ2 is the compound IZ2-B, the phase difference value of the color filter formed from the colored composition containing the compound IZ2-B becomes smaller.
Figure BDA0003121580680001251
[ formula (IZ2-B) wherein RCO11Z2And RCO21Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2,RCO11Z2And RCO21Z2At least one of which is-NRN1Z2RN2Z2
RN1Z2、RN2Z2、R1Z2、R21Z2、R31Z2、R41Z2、R51Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2Each of which may be bonded to each other to form a ring, R21Z2、R31Z2、R41Z2And R51Z2At least one of which is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2At least one group of them is bonded to form a ring.
R101Z2The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. RO1Z2And R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom.
RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
As R in the formula (IZ2-B)CO11Z2、RCO21Z2、R21Z2、R31Z2、R41Z2And R51Z2Examples thereof include the compounds represented by the formula (IZ2) and RCO1Z2、RCO2Z2、R2Z2、R3Z2、R4Z2And R5Z2The same example.
As preferred R in the formula (IZ2-B)CO11Z2、RCO21Z2、R21Z2、R31Z2、R41Z2And R51Z2Examples thereof include the compounds represented by the formula (IZ2) and RCO1Z2、RCO2Z2、R2Z2、R3Z2、R4Z2And R5Z2The same preferred examples as those of (1).
In the formula (IZ2-B), R is1Z2Preferably a hydrogen atom.
In the formula (IZ2-B), RO1Z2The hydrocarbon group is preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, and particularly preferably a hydrogen atom, a methyl group or an ethyl group.
RN1Z2And RN2Z2Preferably a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-CON(R102Z2)2、-N(R102Z2)2、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, still more particularly preferably a hydrogen atom, a methyl group, an ethyl group or a phenyl group, and most preferably a hydrogen atom, a methyl group or an ethyl group. In addition, RN1Z2And RN2Z2The groups may be the same or different, but preferably the same.
In the formula (IZ2-B), R is preferably R from the viewpoint of reducing the retardation value of the color filter formed of the colored composition21Z2、R31Z2、R41Z2And R51Z2At least one of which is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, or-N (R)102Z2)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102Z2、-O-R102Z2、-SO3M or-CO2M,
More preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Among them, R is more preferable31Z2Is nitro or tert-butyl, R21Z2、R41Z2And R51Z2Is a hydrogen atom; or, R21Z2、R31Z2And R51Z2Is a hydrogen atom, R41Z2Is nitro or tert-butyl.
Specific examples of the compound IZ2 include, for example,
examples of the compound of formula (IaZ2) include compounds IaZ2-1 to IaZ2-494 and alkali metal salts thereof each having a substituent shown in table 1Z2, table 2Z2, table 3Z2, table 4Z2, table 5Z2, table 6Z2, table 27Z2, table 28Z2, table 29Z2 and table 30Z 2;
in formula (IbZ2), examples of compounds IbZ2-1 to IbZ2-840 or alkali metal salts thereof having a substituent shown in table 7Z2, table 8Z2, table 9Z2, table 10Z2, table 11Z2, table 12Z2, table 13Z2, table 14Z2, table 31Z2, table 32Z2, table 33Z2, table 34Z2, table 35Z2, table 36Z2, and table 37Z 2;
in formula (IcZ2), compounds IcZ2-1 to IcZ2-296 having a substituent shown in table 15Z2, table 16Z2, table 17Z2, table 18Z2, table 19Z2, table 20Z2, table 21Z2, and table 22Z2, or an alkali metal salt thereof are mentioned.
Ba1Z2Ba2Z2The partial structure represented by any one of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) is shown. The formulae (BB1) to (BB60), (BBK2), (BBK3), (BBK4), (BBK14), (BBI1), (BBO8), (BBO10), (BBD1) and (BBJ2) are the same as B representing formula (IZ1-aa) a1Z1Ba2Z1The same structures as (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) described above. B isa1Z2And Ba2Z2Each represents a chemical bond, Ba1Z2B of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2)1When a chemical bond of (A) is present, Ba2Z2To be B2The chemical bond of (a); b isa1Z2B of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2)2When a chemical bond of (A) is present, Ba2Z2To be B1The chemical bond of (1).
As Ba1Z2Ba2Z2Formula (BB1), formula (BB6), formula (BB8), formula (BB11), formula (BB14), formula (BB19), formula (BB37), formula (BB58), formula (BBJ2), formula (BBO8), and formula (BBO10) are preferable, and formula (BB1), formula (BB6), and formula (BB19) are more preferable.
Figure BDA0003121580680001281
Each symbol in table 1Z2, table 2Z2, table 3Z2, table 4Z2, table 5Z2, table 6Z2, table 7Z2, table 8Z2, table 9Z2, table 10Z2, table 11Z2, table 12Z2, table 13Z2, table 14Z2, table 15Z2, table 16Z2, table 17Z2, table 18Z2, table 19Z2, table 20Z2, table 21Z2, table 22Z2, table 27Z2, table 28Z2, table 29Z2, table 30Z2, table 31Z2, table 32Z2, table 33Z2, table 34Z2, table 35Z2, table 36Z2, and table 37Z2 represents a partial structure below. In the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group, "Hex" represents a hexyl group, "Oct" represents an octyl group, "2 EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group, "CH" represents a cyclohexyl group, "PH" represents a phenyl group, "BZ" represents a benzyl group, "NPR" represents a propyl group, "IPR" represents an isopropyl group, "IBu" represents an isobutyl group, and "EOE" represents a-CH group 2CH2OCH2CH3"ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents-CO-CH3And "COE" represents-COO-CH2CH3"CBA" means-CO2H, "CBM" denotes-CONH2"NH 2" means-NH2Denotes a bond.
In the table, a partial structure represented by the following formula is represented by a symbol.
Figure BDA0003121580680001291
Figure BDA0003121580680001301
Figure BDA0003121580680001311
[ Table 1Z2]
TABLE 1Z2
RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2
IaZ2-1 H H BB1 H
IaZ2-2 Me Me BB1 H
IaZ2-3 Et Et BB1 H
IaZ2-4 Bu Bu BB1 H
IaZ2-5 TBu TBu BB1 H
IaZ2-6 Hex Hex BB1 H
IaZ2-7 Oct Oct BB1 H
IaZ2-8 2EH 2EH BB1 H
IaZ2-9 CHM CHM BB1 H
IaZ2-10 CH CH BB1 H
IaZ2-11 PH PH BB1 H
IaZ2-12 BZ BZ BB1 H
IaZ2-13 NPR NPR BB1 H
IaZ2-14 IPR IPR BB1 H
IaZ2-15 IBu IBu BB1 H
IaZ2-16 EOE EOE BB1 H
IaZ2-17 ALL ALL BB1 H
IaZ2-18 HYE HYE BB1 H
IaZ2-19 H H BB6 H
IaZ2-20 Me Me BB6 H
IaZ2-21 Et Et BB6 H
IaZ2-22 Bu Bu BB6 H
IaZ2-23 TBu TBu BB6 H
IaZ2-24 Hex Hex BB6 H
IaZ2-25 Oct Oct BB6 H
IaZ2-26 2EH 2EH BB6 H
IaZ2-27 CHM CHM BB6 H
IaZ2-28 CH CH BB6 H
IaZ2-29 PH PH BB6 H
IaZ2-30 BZ BZ BB6 H
IaZ2-31 NPR NPR BB6 H
IaZ2-32 IPR IPR BB6 H
IaZ2-33 IBu IBu BB6 H
IaZ2-34 EOE EOE BB6 H
IaZ2-35 ALL ALL BB6 H
IaZ2-36 HYE HYE BB6 H
IaZ2-37 H H BB19 H
IaZ2-38 Me Me BB19 H
IaZ2-39 Et Et BB19 H
IaZ2-40 Bu Bu BB19 H
[ Table 2Z2]
TABLE 2Z2
RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2
IaZ2-41 TBu TBu BB19 H
IaZ2-42 Hex Hex BB19 H
IaZ2-43 Oct Oct BB19 H
IaZ2-44 2EH 2EH BB19 H
IaZ2-45 CHM CHM BB19 H
IaZ2-46 CH CH BB19 H
IaZ2-47 PH PH BB19 H
IaZ2-48 BZ BZ BB19 H
IaZ2-49 NPR NPR BB19 H
IaZ2-50 IPR IPR BB19 H
IaZ2-51 IBu IBu BB19 H
IaZ2-52 EOE EOE BB19 H
IaZ2-53 ALL ALL BB19 H
IaZ2-54 HYE HYE BB19 H
IaZ2-55 H H BB2 H
IaZ2-56 Me Me BB3 H
IaZ2-57 Et Et BB4 H
IaZ2-58 Bu Bu BB5 H
IaZ2-59 TBu TBu BB7 H
IaZ2-60 Hex Hex BB8 H
IaZ2-61 Oct Oct BB9 H
IaZ2-62 2EH 2EH BB10 H
IaZ2-63 CHM CHM BB11 H
IaZ2-64 CH CH BB12 H
IaZ2-65 PH PH BB13 H
IaZ2-66 BZ BZ BB14 H
IaZ2-67 NPR NPR BB15 H
IaZ2-68 IPR IPR BB16 H
IaZ2-69 IBu IBu BB17 H
IaZ2-70 EOE EOE BB18 H
IaZ2-71 ALL ALL BB20 H
IaZ2-72 HYE HYE BB21 H
IaZ2-73 H H BB22 H
IaZ2-74 Me Me BB23 H
IaZ2-75 Et Et BB24 H
IaZ2-76 Bu Bu BB25 H
IaZ2-77 TBu TBu BB26 H
IaZ2-78 Hex Hex BB27 H
IaZ2-79 Oct Oct BB28 H
IaZ2-80 2EH 2EH BB29 H
[ Table 3Z2]
TABLE 3Z2
RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2
IaZ2-81 CHM CHM BB30 H
IaZ2-82 CH CH BB31 H
IaZ2-83 PH PH BB32 H
IaZ2-84 BZ BZ BB33 H
IaZ2-85 NPR NPR BB34 H
IaZ2-86 IPR IPR BB35 H
IaZ2-87 IBu IBu BB36 H
IaZ2-88 EOE EOE BB37 H
IaZ2-89 ALL ALL BB38 H
IaZ2-90 HYE HYE BB39 H
IaZ2-91 H H BB40 H
IaZ2-92 Me Me BB41 H
IaZ2-93 Et Et BB42 H
IaZ2-94 Bu Bu BB43 H
IaZ2-95 TBu TBu BB44 H
IaZ2-96 Hex Hex BB45 H
IaZ2-97 Oct Oct BB46 H
IaZ2-98 2EH 2EH BB47 H
IaZ2-99 CHM CHM BB48 H
IaZ2-100 CH CH BB49 H
IaZ2-101 PH PH BB50 H
IaZ2-102 BZ BZ BB51 H
IaZ2-103 NPR NPR BB52 H
IaZ2-104 IPR IPR BB53 H
IaZ2-105 IBu IBu BB54 H
IaZ2-106 EOE EOE BB55 H
IaZ2-107 ALL ALL BB56 H
IaZ2-108 HYE HYE BB57 H
IaZ2-109 H H BB58 H
IaZ2-110 Me Me BB59 H
IaZ2-111 Et Et BB60 H
IaZ2-112 H HYE BB1 H
IaZ2-113 Me H BB1 H
IaZ2-114 Et Me BB1 H
IaZ2-115 Bu Et BB1 H
IaZ2-116 TBu Bu BB1 H
IaZ2-117 Hex TBu BB1 H
IaZ2-118 Oct Hex BB1 H
IaZ2-119 2EH Oct BB1 H
IaZ2-120 CHM 2EH BB1 H
[ Table 4Z2]
TABLE 4Z2
RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2
IaZ2-121 CH CHM BB1 H
IaZ2-122 PH CH BB1 H
IaZ2-123 BZ PH BB1 H
IaZ2-124 NPR BZ BB1 H
IaZ2-125 IPR NPR BB1 H
IaZ2-126 IBu IPR BB1 H
IaZ2-127 EOE IBu BB1 H
IaZ2-128 ALL EOE BB1 H
IaZ2-129 HYE ALL BB1 H
IaZ2-130 H BZ BB6 H
IaZ2-131 Me NPR BB6 H
IaZ2-132 Et Me BB6 H
IaZ2-133 Bu IBu BB6 H
IaZ2-134 TBu EOE BB6 H
IaZ2-135 Hex ALL BB6 H
IaZ2-136 Oct HYE BB6 H
IaZ2-137 2EH H BB6 H
IaZ2-138 CHM IPR BB6 H
IaZ2-139 CH Et BB6 H
IaZ2-140 PH Bu BB6 H
IaZ2-141 BZ TBu BB6 H
IaZ2-142 NPR Hex BB6 H
IaZ2-143 IPR Oct BB6 H
IaZ2-144 IBu 2EH BB6 H
IaZ2-145 EOE CHM BB6 H
IaZ2-146 ALL CH BB6 H
IaZ2-147 HYE PH BB6 H
IaZ2-148 H Oct BB19 H
IaZ2-149 Me Et BB19 H
IaZ2-150 Et CHM BB19 H
IaZ2-151 Bu CH BB19 H
IaZ2-152 TBu PH BB19 H
IaZ2-153 Hex BZ BB19 H
IaZ2-154 Oct 2EH BB19 H
IaZ2-155 2EH IPR BB19 H
IaZ2-156 CHM IBu BB19 H
IaZ2-157 CH EOE BB19 H
IaZ2-158 PH ALL BB19 H
IaZ2-159 BZ HYE BB19 H
IaZ2-160 NPR H BB19 H
[ Table 5Z2]
TABLE 5Z2
RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2
IaZ2-161 IPR Me BB19 H
IaZ2-162 IBu NPR BB19 H
IaZ2-163 EOE Bu BB19 H
IaZ2-164 ALL TBu BB19 H
IaZ2-165 HYE Hex BB19 H
IaZ2-166 H EOE BB2 H
IaZ2-167 Me ALL BB3 H
IaZ2-168 Et HYE BB4 H
IaZ2-169 Bu H BB5 H
IaZ2-170 TBu Me BB7 H
IaZ2-171 Hex Et BB8 H
IaZ2-172 Oct Bu BB9 H
IaZ2-173 2EH TBu BB10 H
IaZ2-174 CHM Hex BB11 H
IaZ2-175 CH Oct BB12 H
IaZ2-176 PH 2EH BB13 H
IaZ2-177 BZ CHM BB14 H
IaZ2-178 NPR CH BB15 H
IaZ2-179 IPR PH BB16 H
IaZ2-180 IBu BZ BB17 H
IaZ2-181 EOE NPR BB18 H
IaZ2-182 ALL IPR BB20 H
IaZ2-183 HYE IBu BB21 H
IaZ2-184 H TBu BB22 H
IaZ2-185 Me Hex BB23 H
IaZ2-186 Et Oct BB24 H
IaZ2-187 Bu 2EH BB25 H
IaZ2-188 TBu CHM BB26 H
IaZ2-189 Hex CH BB27 H
IaZ2-190 Oct PH BB28 H
IaZ2-191 2EH BZ BB29 H
IaZ2-192 CHM NPR BB30 H
IaZ2-193 CH IPR BB31 H
IaZ2-194 PH IBu BB32 H
IaZ2-195 BZ EOE BB33 H
IaZ2-196 NPR ALL BB34 H
IaZ2-197 IPR HYE BB35 H
IaZ2-198 IBu H BB36 H
IaZ2-199 EOE Me BB37 H
IaZ2-200 ALL Et BB38 H
[ Table 6Z2]
TABLE 6Z2
RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2
IaZ2-201 HYE Bu BB39 H
IaZ2-202 H CHM BB40 H
IaZ2-203 Me CH BB41 H
IaZ2-204 Et PH BB42 H
IaZ2-205 Bu BZ BB43 H
IaZ2-206 TBu NPR BB44 H
IaZ2-207 Hex IPR BB45 H
IaZ2-208 Oct IBu BB46 H
IaZ2-209 2EH EOE BB47 H
IaZ2-210 CHM ALL BB48 H
IaZ2-211 CH HYE BB49 H
IaZ2-212 PH H BB50 H
IaZ2-213 BZ Me BB51 H
IaZ2-214 NPR Et BB52 H
IaZ2-215 IPR Bu BB53 H
IaZ2-216 IBu TBu BB54 H
IaZ2-217 EOE Hex BB55 H
IaZ2-218 ALL Oct BB56 H
IaZ2-219 HYE 2EH BB57 H
IaZ2-220 H Me BB58 H
IaZ2-221 Me Et BB59 H
IaZ2-222 Et Bu BB60 H
IaZ2-223 Me Me BB14 H
[ Table 7Z2]
TABLE 7Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-1 H H H H BB1 H
IbZ2-2 Me H Me H BB1 H
IbZ2-3 Et H Et H BB1 H
IbZ2-4 PH H PH H BB1 H
IbZ2-5 Bu H Bu H BB1 H
IbZ2-6 TBu H TBu H BB1 H
IbZ2-7 Hex H Hex H BB1 H
IbZ2-8 Oct H Oct H BB1 H
IbZ2-9 2EH H 2EH H BB1 H
IbZ2-10 CHM H CHM H BB1 H
IbZ2-11 CH H CH H BB1 H
IbZ2-12 BZ H BZ H BB1 H
IbZ2-13 NPR H NPR H BB1 H
IbZ2-14 IPR H IPR H BB1 H
IbZ2-15 IBu H IBu H BB1 H
IbZ2-16 EOE H EOE H BB1 H
IbZ2-17 ALL H ALL H BB1 H
IbZ2-18 NH2 H NH2 H BB1 H
IbZ2-19 CBM H CBM H BB1 H
IbZ2-20 COM H COM H BB1 H
IbZ2-21 COE H COE H BB1 H
IbZ2-22 CBA H CBA H BB1 H
IbZ2-23 HYE H HYE H BB1 H
IbZ2-24 Me Me Me Me BB1 H
IbZ2-25 Et Et Et Et BB1 H
IbZ2-26 PH PH PH PH BB1 H
IbZ2-27 Bu Me Bu Me BB1 H
IbZ2-28 TBu Et TBu Et BB1 H
IbZ2-29 Hex NPR Hex NPR BB1 H
IbZ2-30 Oct IPR Oct IPR BB1 H
IbZ2-31 2EH HYE 2EH HYE BB1 H
IbZ2-32 CHM ALL CHM ALL BB1 H
IbZ2-33 CH COM CH COM BB1 H
IbZ2-34 BZ Me BZ Me BB1 H
IbZ2-35 NPR Et NPR Et BB1 H
IbZ2-36 IPR NPR IPR NPR BB1 H
IbZ2-37 IBu IPR IBu IPR BB1 H
IbZ2-38 EOE HYE EOE HYE BB1 H
IbZ2-39 ALL ALL ALL ALL BB1 H
IbZ2-40 NH2 COM NH2 COM BB1 H
[ Table 8Z2]
TABLE 8Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-41 CBM Me CBM Me BB1 H
IbZ2-42 COM Et COM Et BB1 H
IbZ2-43 COE NPR COE NPR BB1 H
IbZ2-44 CBA IPR CBA IPR BB1 H
IbZ2-45 HYE HYE HYE HYE BB1 H
IbZ2-46 Bu Bu Bu Bu BB1 H
IbZ2-47 TBu TBu TBu TBu BB1 H
IbZ2-48 Hex Hex Hex Hex BB1 H
IbZ2-49 Oct Oct Oct Oct BB1 H
IbZ2-50 2EH 2EH 2EH 2EH BB1 H
IbZ2-51 CHM CHM CHM CHM BB1 H
IbZ2-52 CH CH CH CH BB1 H
IbZ2-53 BZ BZ BZ BZ BB1 H
IbZ2-54 NPR NPR NPR NPR BB1 H
IbZ2-55 IPR IPR IPR IPR BB1 H
IbZ2-56 IBu IBu IBu IBu BB1 H
IbZ2-57 EOE EOE EOE EOE BB1 H
IbZ2-58 NH2 NH2 NH2 NH2 BB1 H
IbZ2-59 CBM CBM CBM CBM BB1 H
IbZ2-60 COM COM COM COM BB1 H
IbZ2-61 COE COE COE COE BB1 H
IbZ2-62 CBA CBA CBA CBA BB1 H
IbZ2-63 H H H H BB6 H
IbZ2-64 Me H Me H BB6 H
IbZ2-65 Et H Et H BB6 H
IbZ2-66 PH H PH H BB6 H
IbZ2-67 Bu H Bu H BB6 H
IbZ2-68 TBu H TBu H BB6 H
IbZ2-69 Hex H Hex H BB6 H
IbZ2-70 Oct H Oct H BB6 H
IbZ2-71 2EH H 2EH H BB6 H
IbZ2-72 CHM H CHM H BB6 H
IbZ2-73 CH H CH H BB6 H
IbZ2-74 BZ H BZ H BB6 H
IbZ2-75 NPR H NPR H BB6 H
IbZ2-76 IPR H IPR H BB6 H
IbZ2-77 IBu H IBu H BB6 H
IbZ2-78 EOE H EOE H BB6 H
IbZ2-79 ALL H ALL H BB6 H
IbZ2-80 NH2 H NH2 H BB6 H
[ Table 9Z2]
TABLE 9Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-81 CBM H CBM H BB6 H
IbZ2-82 COM H COM H BB6 H
IbZ2-83 COE H COE H BB6 H
IbZ2-84 CBA H CBA H BB6 H
IbZ2-85 HYE H HYE H BB6 H
IbZ2-86 Me Me Me Me BB6 H
IbZ2-87 Et Et Et Et BB6 H
IbZ2-88 PH PH PH PH BB6 H
IbZ2-89 Bu Me Bu Me BB6 H
IbZ2-90 TBu Et TBu Et BB6 H
IbZ2-91 Hex NPR Hex NPR BB6 H
IbZ2-92 Oct IPR Oct IPR BB6 H
IbZ2-93 2EH HYE 2EH HYE BB6 H
IbZ2-94 CHM ALL CHM ALL BB6 H
IbZ2-95 CH COM CH COM BB6 H
IbZ2-96 BZ Me BZ Me BB6 H
IbZ2-97 NPR Et NPR Et BB6 H
IbZ2-98 IPR NPR IPR NPR BB6 H
IbZ2-99 IBu IPR IBu IPR BB6 H
IbZ2-100 EOE HYE EOE HYE BB6 H
IbZ2-101 ALL ALL ALL ALL BB6 H
IbZ2-102 NH2 COM NH2 COM BB6 H
IbZ2-103 CBM Me CBM Me BB6 H
IbZ2-104 COM Et COM Et BB6 H
IbZ2-105 COE NPR COE NPR BB6 H
IbZ2-106 CBA IPR CBA IPR BB6 H
IbZ2-107 HYE HYE HYE HYE BB6 H
IbZ2-108 Bu Bu Bu Bu BB6 H
IbZ2-109 TBu TBu TBu TBu BB6 H
IbZ2-110 Hex Hex Hex Hex BB6 H
IbZ2-111 Oct Oct Oct Oct BB6 H
IbZ2-112 2EH 2EH 2EH 2EH BB6 H
IbZ2-113 CHM CHM CHM CHM BB6 H
IbZ2-114 CH CH CH CH BB6 H
IbZ2-115 BZ BZ BZ BZ BB6 H
IbZ2-116 NPR NPR NPR NPR BB6 H
IbZ2-117 IPR IPR IPR IPR BB6 H
IbZ2-118 IBu IBu IBu IBu BB6 H
IbZ2-119 EOE EOE EOE EOE BB6 H
IbZ2-120 NH2 NH2 NH2 NH2 BB6 H
[ Table 10Z2]
TABLE 10Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-121 CBM CBM CBM CBM BB6 H
IbZ2-122 COM COM COM COM BB6 H
IbZ2-123 COE COE COE COE BB6 H
IbZ2-124 CBA CBA CBA CBA BB6 H
IbZ2-125 H H H H BB19 H
IbZ2-126 Me H Me H BB19 H
IbZ2-127 Et H Et H BB19 H
IbZ2-128 PH H PH H BB19 H
IbZ2-129 Bu H Bu H BB19 H
IbZ2-130 TBu H TBu H BB19 H
IbZ2-131 Hex H Hex H BB19 H
IbZ2-132 Oct H Oct H BB19 H
IbZ2-133 2EH H 2EH H BB19 H
IbZ2-134 CHM H CHM H BB19 H
IbZ2-135 CH H CH H BB19 H
IbZ2-136 BZ H BZ H BB19 H
IbZ2-137 NPR H NPR H BB19 H
IbZ2-138 IPR H IPR H BB19 H
IbZ2-139 IBu H IBu H BB19 H
IbZ2-140 EOE H EOE H BB19 H
IbZ2-141 ALL H ALL H BB19 H
IbZ2-142 NH2 H NH2 H BB19 H
IbZ2-143 CBM H CBM H BB19 H
IbZ2-144 COM H COM H BB19 H
IbZ2-145 COE H COE H BB19 H
IbZ2-146 CBA H CBA H BB19 H
IbZ2-147 HYE H HYE H BB19 H
IbZ2-148 Me Me Me Me BB19 H
IbZ2-149 Et Et Et Et BB19 H
IbZ2-150 PH PH PH PH BB19 H
IbZ2-151 Bu Me Bu Me BB19 H
IbZ2-152 TBu Et TBu Et BB19 H
IbZ2-153 Hex NPR Hex NPR BB19 H
IbZ2-154 Oct IPR Oct IPR BB19 H
IbZ2-155 2EH HYE 2EH HYE BB19 H
IbZ2-156 CHM ALL CHM ALL BB19 H
IbZ2-157 CH COM CH COM BB19 H
IbZ2-158 BZ Me BZ Me BB19 H
IbZ2-159 NPR Et NPR Et BB19 H
IbZ2-160 IPR NPR IPR NPR BB19 H
[ Table 11Z2]
TABLE 11Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-161 IBu IPR IBu IPR BB19 H
IbZ2-162 EOE HYE EOE HYE BB19 H
IbZ2-163 ALL ALL ALL ALL BB19 H
IbZ2-164 NH2 COM NH2 COM BB19 H
IbZ2-165 CBM Me CBM Me BB19 H
IbZ2-166 COM Et COM Et BB19 H
IbZ2-167 COE NPR COE NPR BB19 H
IbZ2-168 CBA IPR CBA IPR BB19 H
IbZ2-169 HYE HYE HYE HYE BB19 H
IbZ2-170 Bu Bu Bu Bu BB19 H
IbZ2-171 TBu TBu TBu TBu BB19 H
IbZ2-172 Hex Hex Hex Hex BB19 H
IbZ2-173 Oct Oct Oct Oct BB19 H
IbZ2-174 2EH 2EH 2EH 2EH BB19 H
IbZ2-175 CHM CHM CHM CHM BB19 H
IbZ2-176 CH CH CH CH BB19 H
IbZ2-177 BZ BZ BZ BZ BB19 H
IbZ2-178 NPR NPR NPR NPR BB19 H
IbZ2-179 IPR IPR IPR IPR BB19 H
IbZ2-180 IBu IBu IBu IBu BB19 H
IbZ2-181 EOE EOE EOE EOE BB19 H
IbZ2-182 NH2 NH2 NH2 NH2 BB19 H
IbZ2-183 CBM CBM CBM CBM BB19 H
IbZ2-184 COM COM COM COM BB19 H
IbZ2-185 COE COE COE COE BB19 H
IbZ2-186 CBA CBA CBA CBA BB19 H
IbZ2-187 H H H H BB2 H
IbZ2-188 HYE HYE HYE HYE BB3 H
IbZ2-189 BZ BZ BZ BZ BB4 H
IbZ2-190 Me H Me H BB5 H
IbZ2-191 CBA IPR CBA IPR BB7 H
IbZ2-192 NPR NPR NPR NPR BB8 H
IbZ2-193 Et H Et H BB9 H
IbZ2-194 COE NPR COE NPR BB10 H
IbZ2-195 CH CH CH CH BB11 H
IbZ2-196 PH H PH H BB12 H
IbZ2-197 COM Et COM Et BB13 H
IbZ2-198 IPR IPR IPR IPR BB14 H
IbZ2-199 Bu H Bu H BB15 H
IbZ2-200 CBM Me CBM Me BB16 H
[ Table 12Z2]
TABLE 12Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-201 IBu IBu IBu IBu BB17 H
IbZ2-202 TBu H TBu H BB18 H
IbZ2-203 NH2 COM NH2 COM BB20 H
IbZ2-204 CHM CHM CHM CHM BB21 H
IbZ2-205 Hex H Hex H BB22 H
IbZ2-206 ALL ALL ALL ALL BB23 H
IbZ2-207 EOE EOE EOE EOE BB24 H
IbZ2-208 Oct H Oct H BB25 H
IbZ2-209 EOE HYE EOE HYE BB26 H
IbZ2-210 2EH 2EH 2EH 2EH BB27 H
IbZ2-211 2EH H 2EH H BB28 H
IbZ2-212 IBu IPR IBu IPR BB29 H
IbZ2-213 NH2 NH2 NH2 NH2 BB30 H
IbZ2-214 CHM H CHM H BB31 H
IbZ2-215 IPR NPR IPR NPR BB32 H
IbZ2-216 Oct Oct Oct Oct BB33 H
IbZ2-217 CH H CH H BB34 H
IbZ2-218 NPR Et NPR Et BB35 H
IbZ2-219 CBM CBM CBM CBM BB36 H
IbZ2-220 BZ H BZ H BB37 H
IbZ2-221 BZ Me BZ Me BB38 H
IbZ2-222 Hex Hex Hex Hex BB39 H
IbZ2-223 HYE H HYE H BB40 H
IbZ2-224 CH COM CH COM BB41 H
IbZ2-225 COM COM COM COM BB42 H
IbZ2-226 NPR H NPR H BB43 H
IbZ2-227 2EH HYE 2EH HYE BB44 H
IbZ2-228 IPR H IPR H BB45 H
IbZ2-229 CHM ALL CHM ALL BB46 H
IbZ2-230 COE COE COE COE BB47 H
IbZ2-231 IBu H IBu H BB48 H
IbZ2-232 Hex NPR Hex NPR BB49 H
IbZ2-233 EOE H EOE H BB50 H
IbZ2-234 Oct IPR Oct IPR BB51 H
IbZ2-235 TBu TBu TBu TBu BB52 H
IbZ2-236 ALL H ALL H BB53 H
IbZ2-237 TBu Et TBu Et BB54 H
IbZ2-238 NH2 H NH2 H BB55 H
IbZ2-239 Bu Bu Bu Bu BB56 H
IbZ2-240 CBM H CBM H BB57 H
[ Table 13Z2]
TABLE 13Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-241 PH PH PH PH BB58 H
IbZ2-242 COM H COM H BB59 H
IbZ2-243 Bu Me Bu Me BB60 H
IbZ2-244 CBA CBA CBA CBA BB2 H
IbZ2-245 COE H COE H BB3 H
IbZ2-246 Me Me Me Me BB4 H
IbZ2-247 CBA H CBA H BB5 H
IbZ2-248 Et Et Et Et BB7 H
IbZ2-249 H H NPR Et BB1 H
IbZ2-250 HYE HYE CBM CBM BB2 H
IbZ2-251 BZ BZ BZ H BB3 H
IbZ2-252 Me H BZ Me BB4 H
IbZ2-253 CBA IPR Hex Hex BB5 H
IbZ2-254 NPR NPR HYE H BB6 H
IbZ2-255 Et H CH COM BB7 H
IbZ2-256 COE NPR COM COM BB8 H
IbZ2-257 CH CH NPR H BB9 H
IbZ2-258 PH H 2EH HYE BB10 H
IbZ2-259 COM Et IPR H BB11 H
IbZ2-260 IPR IPR CHM ALL BB12 H
IbZ2-261 Bu H COE COE BB13 H
IbZ2-262 CBM Me IBu H BB14 H
IbZ2-263 IBu IBu Hex NPR BB15 H
IbZ2-264 TBu H EOE H BB16 H
IbZ2-265 NH2 COM Oct IPR BB17 H
IbZ2-266 CHM CHM TBu TBu BB18 H
IbZ2-267 Hex H ALL H BB19 H
IbZ2-268 ALL ALL TBu Et BB20 H
IbZ2-269 EOE EOE NH2 H BB21 H
IbZ2-270 Oct H Bu Bu BB22 H
IbZ2-271 EOE HYE CBM H BB23 H
IbZ2-272 2EH 2EH PH PH BB24 H
IbZ2-273 2EH H COM H BB25 H
IbZ2-274 IBu IPR Bu Me BB26 H
IbZ2-275 NH2 NH2 CBA CBA BB27 H
IbZ2-276 CHM H COE H BB28 H
IbZ2-277 IPR NPR Me Me BB29 H
IbZ2-278 Oct Oct CBA H BB30 H
IbZ2-279 CH H Et Et BB31 H
IbZ2-280 NPR Et H H BB32 H
[ Table 14Z2]
TABLE 14Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-281 CBM CBM HYE HYE BB33 H
IbZ2-282 BZ H BZ BZ BB34 H
IbZ2-283 BZ Me Me H BB35 H
IbZ2-284 Hex Hex CBA IPR BB36 H
IbZ2-285 HYE H NPR NPR BB37 H
IbZ2-286 CH COM Et H BB38 H
IbZ2-287 COM COM COE NPR BB39 H
IbZ2-288 NPR H CH CH BB40 H
IbZ2-289 2EH HYE PH H BB41 H
IbZ2-290 IPR H COM Et BB42 H
IbZ2-291 CHM ALL IPR IPR BB43 H
IbZ2-292 COE COE Bu H BB44 H
IbZ2-293 IBu H CBM Me BB45 H
IbZ2-294 Hex NPR IBu IBu BB46 H
IbZ2-295 EOE H TBu H BB47 H
IbZ2-296 Oct IPR NH2 COM BB48 H
IbZ2-297 TBu TBu CHM CHM BB49 H
IbZ2-298 ALL H Hex H BB50 H
IbZ2-299 TBu Et ALL ALL BB51 H
IbZ2-300 NH2 H EOE EOE BB52 H
IbZ2-301 Bu Bu Oct H BB53 H
IbZ2-302 CBM H EOE HYE BB54 H
IbZ2-303 PH PH 2EH 2EH BB55 H
IbZ2-304 COM H 2EH H BB56 H
IbZ2-305 Bu Me IBu IPR BB57 H
IbZ2-306 CBA CBA NH2 NH2 BB58 H
IbZ2-307 COE H CHM H BB59 H
IbZ2-308 Me Me IPR NPR BB60 H
IbZ2-309 CBA H Oct Oct BB1 H
IbZ2-310 Et Et CH H BB19 H
IbZ2-311 NA1 H NA1 H BB1 H
IbZ2-312 NA1 H NA1 H BB19 H
IbZ2-313 NA2 H NA2 H BB1 H
IbZ2-314 NA2 H NA2 H BB19 H
IbZ2-315 NA1 H NA1 H BBO8 H
IbZ2-316 NA1 H NA1 H BB8 H
[ Table 15Z2]
TABLE 15Z2
RO13Z2 RN13Z2 RN23Z2 Ba1Z2Ba2Z2 R1Z2
IcZ2-1 H H H BB1 H
IcZ2-2 H Me H BB1 H
IcZ2-3 H Et H BB1 H
IcZ2-4 H PH H BB1 H
IcZ2-5 H NPR H BB1 H
IcZ2-6 H NH2 H BB1 H
IcZ2-7 H CBM H BB1 H
IcZ2-8 H COM H BB1 H
IcZ2-9 H HYE H BB1 H
IcZ2-10 H Me Me BB1 H
IcZ2-11 H Et Et BB1 H
IcZ2-12 H PH PH BB1 H
IcZ2-13 H HYE HYE BB1 H
IcZ2-14 Me H H BB1 H
IcZ2-15 Me Me H BB1 H
IcZ2-16 Me Et H BB1 H
IcZ2-17 Me PH H BB1 H
IcZ2-18 Me NPR H BB1 H
IcZ2-19 Me NH2 H BB1 H
IcZ2-20 Me CBM H BB1 H
IcZ2-21 Me COM H BB1 H
IcZ2-22 Me HYE H BB1 H
IcZ2-23 Me Me Me BB1 H
IcZ2-24 Me Et Et BB1 H
IcZ2-25 Me PH PH BB1 H
IcZ2-26 Me HYE HYE BB1 H
IcZ2-27 Et H H BB1 H
IcZ2-28 Et Me H BB1 H
IcZ2-29 Et Et H BB1 H
IcZ2-30 Et PH H BB1 H
IcZ2-31 Et NPR H BB1 H
IcZ2-32 Et NH2 H BB1 H
IcZ2-33 Et CBM H BB1 H
IcZ2-34 Et COM H BB1 H
IcZ2-35 Et HYE H BB1 H
IcZ2-36 Et Me Me BB1 H
IcZ2-37 Et Et Et BB1 H
IcZ2-38 Et PH PH BB1 H
IcZ2-39 Et HYE HYE BB1 H
IcZ2-40 PH H H BB1 H
[ Table 16Z2]
TABLE 16Z2
RO13Z2 RN13Z2 RN23Z2 Ba1Z2Ba2Z2 R1Z2
IcZ2-41 PH Me H BB1 H
IcZ2-42 PH Et H BB1 H
IcZ2-43 PH PH H BB1 H
IcZ2-44 PH NPR H BB1 H
IcZ2-45 PH NH2 H BB1 H
IcZ2-46 PH CBM H BB1 H
IcZ2-47 PH COM H BB1 H
IcZ2-48 PH HYE H BB1 H
IcZ2-49 PH Me Me BB1 H
IcZ2-50 PH Et Et BB1 H
IcZ2-51 PH PH PH BB1 H
IcZ2-52 PH HYE HYE BB1 H
IcZ2-53 NPR H H BB1 H
IcZ2-54 NPR Me H BB1 H
IcZ2-55 NPR Et H BB1 H
IcZ2-56 NPR PH H BB1 H
IcZ2-57 NPR NPR H BB1 H
IcZ2-58 NPR NH2 H BB1 H
IcZ2-59 NPR CBM H BB1 H
IcZ2-60 NPR COM H BB1 H
IcZ2-61 NPR HYE H BB1 H
IcZ2-62 NPR Me Me BB1 H
IcZ2-63 NPR Et Et BB1 H
IcZ2-64 NPR PH PH BB1 H
IcZ2-65 NPR HYE HYE BB1 H
IcZ2-66 HYE H H BB1 H
IcZ2-67 HYE Me H BB1 H
IcZ2-68 HYE Et H BB1 H
IcZ2-69 HYE PH H BB1 H
IcZ2-70 HYE NPR H BB1 H
IcZ2-71 HYE NH2 H BB1 H
IcZ2-72 HYE CBM H BB1 H
IcZ2-73 HYE COM H BB1 H
IcZ2-74 HYE HYE H BB1 H
IcZ2-75 HYE Me Me BB1 H
IcZ2-76 HYE Et Et BB1 H
IcZ2-77 HYE PH PH BB1 H
IcZ2-78 HYE HYE HYE BB1 H
IcZ2-79 H H H BB6 H
IcZ2-80 H Me H BB6 H
[ Table 17Z2]
TABLE 17Z2
RO13Z2 RN13Z2 RN23Z2 Ba1Z2Ba2Z2 R1Z2
IcZ2-81 H Et H BB6 H
IcZ2-82 H PH H BB6 H
IcZ2-83 H NPR H BB6 H
IcZ2-84 H NH2 H BB6 H
IcZ2-85 H CBM H BB6 H
IcZ2-86 H COM H BB6 H
IcZ2-87 H HYE H BB6 H
IcZ2-88 H Me Me BB6 H
IcZ2-89 H Et Et BB6 H
IcZ2-90 H PH PH BB6 H
IcZ2-91 H HYE HYE BB6 H
IcZ2-92 Me H H BB6 H
IcZ2-93 Me Me H BB6 H
IcZ2-94 Me Et H BB6 H
IcZ2-95 Me PH H BB6 H
IcZ2-96 Me NPR H BB6 H
IcZ2-97 Me NH2 H BB6 H
IcZ2-98 Me CBM H BB6 H
IcZ2-99 Me COM H BB6 H
IcZ2-100 Me HYE H BB6 H
IcZ2-101 Me Me Me BB6 H
IcZ2-102 Me Et Et BB6 H
IcZ2-103 Me PH PH BB6 H
IcZ2-104 Me HYE HYE BB6 H
IcZ2-105 Et H H BB6 H
IcZ2-106 Et Me H BB6 H
IcZ2-107 Et Et H BB6 H
IcZ2-108 Et PH H BB6 H
IcZ2-109 Et NPR H BB6 H
IcZ2-110 Et NH2 H BB6 H
IcZ2-111 Et CBM H BB6 H
IcZ2-112 Et COM H BB6 H
IcZ2-113 Et HYE H BB6 H
IcZ2-114 Et Me Me BB6 H
IcZ2-115 Et Et Et BB6 H
IcZ2-116 Et PH PH BB6 H
IcZ2-117 Et HYE HYE BB6 H
IcZ2-118 PH H H BB6 H
IcZ2-119 PH Me H BB6 H
IcZ2-120 PH Et H BB6 H
[ Table 18Z2]
TABLE 18Z2
RO13Z2 RN13Z2 RN23Z2 Ba1Z2Ba2Z2 R1Z2
IcZ2-121 PH PH H BB6 H
IcZ2-122 PH NPR H BB6 H
IcZ2-123 PH NH2 H BB6 H
IcZ2-124 PH CBM H BB6 H
IcZ2-125 PH COM H BB6 H
IcZ2-126 PH HYE H BB6 H
IcZ2-127 PH Me Me BB6 H
IcZ2-128 PH Et Et BB6 H
IcZ2-129 PH PH PH BB6 H
IcZ2-130 PH HYE HYE BB6 H
IcZ2-131 NPR H H BB6 H
IcZ2-132 NPR Me H BB6 H
IcZ2-133 NPR Et H BB6 H
IcZ2-134 NPR PH H BB6 H
IcZ2-135 NPR NPR H BB6 H
IcZ2-136 NPR NH2 H BB6 H
IcZ2-137 NPR CBM H BB6 H
IcZ2-138 NPR COM H BB6 H
IcZ2-139 NPR HYE H BB6 H
IcZ2-140 NPR Me Me BB6 H
IcZ2-141 NPR Et Et BB6 H
IcZ2-142 NPR PH PH BB6 H
IcZ2-143 NPR HYE HYE BB6 H
IcZ2-144 HYE H H BB6 H
IcZ2-145 HYE Me H BB6 H
IcZ2-146 HYE Et H BB6 H
IcZ2-147 HYE PH H BB6 H
IcZ2-148 HYE NPR H BB6 H
IcZ2-149 HYE NH2 H BB6 H
IcZ2-150 HYE CBM H BB6 H
IcZ2-151 HYE COM H BB6 H
IcZ2-152 HYE HYE H BB6 H
IcZ2-153 HYE Me Me BB6 H
IcZ2-154 HYE Et Et BB6 H
IcZ2-155 HYE PH PH BB6 H
IcZ2-156 HYE HYE HYE BB6 H
IcZ2-157 H H H BB19 H
IcZ2-158 H Me H BB19 H
IcZ2-159 H Et H BB19 H
IcZ2-160 H PH H BB19 H
[ Table 19Z2]
TABLE 19Z2
RO13Z2 RN13Z2 RN23Z2 Ba1Z2Ba2Z2 R1Z2
IcZ2-161 H NPR H BB19 H
IcZ2-162 H NH2 H BB19 H
IcZ2-163 H CBM H BB19 H
IcZ2-164 H COM H BB19 H
IcZ2-165 H HYE H BB19 H
IcZ2-166 H Me Me BB19 H
IcZ2-167 H Et Et BB19 H
IcZ2-168 H PH PH BB19 H
IcZ2-169 H HYE HYE BB19 H
IcZ2-170 Me H H BB19 H
IcZ2-171 Me Me H BB19 H
IcZ2-172 Me Et H BB19 H
IcZ2-173 Me PH H BB19 H
IcZ2-174 Me NPR H BB19 H
IcZ2-175 Me NH2 H BB19 H
IcZ2-176 Me CBM H BB19 H
IcZ2-177 Me COM H BB19 H
IcZ2-178 Me HYE H BB19 H
IcZ2-179 Me Me Me BB19 H
IcZ2-180 Me Et Et BB19 H
IcZ2-181 Me PH PH BB19 H
IcZ2-182 Me HYE HYE BB19 H
IcZ2-183 Et H H BB19 H
IcZ2-184 Et Me H BB19 H
IcZ2-185 Et Et H BB19 H
IcZ2-186 Et PH H BB19 H
IcZ2-187 Et NPR H BB19 H
IcZ2-188 Et NH2 H BB19 H
IcZ2-189 Et CBM H BB19 H
IcZ2-190 Et COM H BB19 H
IcZ2-191 Et HYE H BB19 H
IcZ2-192 Et Me Me BB19 H
IcZ2-193 Et Et Et BB19 H
IcZ2-194 Et PH PH BB19 H
IcZ2-195 Et HYE HYE BB19 H
IcZ2-196 PH H H BB19 H
IcZ2-197 PH Me H BB19 H
IcZ2-198 PH Et H BB19 H
IcZ2-199 PH PH H BB19 H
IcZ2-200 PH NPR H BB19 H
[ Table 20Z2]
TABLE 20Z2
RO13Z2 RN13Z2 RN23Z2 Ba1Z2Ba2Z2 R1Z2
IcZ2-201 PH NH2 H BB19 H
IcZ2-202 PH CBM H BB19 H
IcZ2-203 PH COM H BB19 H
IcZ2-204 PH HYE H BB19 H
IcZ2-205 PH Me Me BB19 H
IcZ2-206 PH Et Et BB19 H
IcZ2-207 PH PH PH BB19 H
IcZ2-208 PH HYE HYE BB19 H
IcZ2-209 NPR H H BB19 H
IcZ2-210 NPR Me H BB19 H
IcZ2-211 NPR Et H BB19 H
IcZ2-212 NPR PH H BB19 H
IcZ2-213 NPR NPR H BB19 H
IcZ2-214 NPR NH2 H BB19 H
IcZ2-215 NPR CBM H BB19 H
IcZ2-216 NPR COM H BB19 H
IcZ2-217 NPR HYE H BB19 H
IcZ2-218 NPR Me Me BB19 H
IcZ2-219 NPR Et Et BB19 H
IcZ2-220 NPR PH PH BB19 H
IcZ2-221 NPR HYE HYE BB19 H
IcZ2-222 HYE H H BB19 H
IcZ2-223 HYE Me H BB19 H
IcZ2-224 HYE Et H BB19 H
IcZ2-225 HYE PH H BB19 H
IcZ2-226 HYE NPR H BB19 H
IcZ2-227 HYE NH2 H BB19 H
IcZ2-228 HYE CBM H BB19 H
IcZ2-229 HYE COM H BB19 H
IcZ2-230 HYE HYE H BB19 H
IcZ2-231 HYE Me Me BB19 H
IcZ2-232 HYE Et Et BB19 H
IcZ2-233 HYE PH PH BB19 H
IcZ2-234 HYE HYE HYE BB19 H
IcZ2-235 H Hex H BB1 H
IcZ2-236 Me ALL ALL BB2 H
IcZ2-237 Et EOE EOE BB3 H
IcZ2-238 PH Oct H BB4 H
IcZ2-239 NPR EOE HYE BB5 H
IcZ2-240 HYE 2EH 2EH BB6 H
[ Table 21Z2]
TABLE 21Z2
RO13Z2 RN13Z2 RN23Z2 Ba1Z2Ba2Z2 R1Z2
IcZ2-241 Me 2EH H BB7 H
IcZ2-242 Et IBu IPR BB8 H
IcZ2-243 H NH2 NH2 BB9 H
IcZ2-244 Me CHM H BB10 H
IcZ2-245 Et IPR NPR BB11 H
IcZ2-246 Bu Oct Oct BB12 H
IcZ2-247 TBu CH H BB13 H
IcZ2-248 Hex NPR Et BB14 H
IcZ2-249 Oct CBM CBM BB15 H
IcZ2-250 2EH BZ H BB16 H
IcZ2-251 CHM BZ Me BB17 H
IcZ2-252 CH Hex Hex BB18 H
IcZ2-253 PH HYE H BB19 H
IcZ2-254 BZ CH COM BB20 H
IcZ2-255 NPR COM COM BB21 H
IcZ2-256 IPR NPR H BB22 H
IcZ2-257 IBu 2EH HYE BB23 H
IcZ2-258 EOE IPR H BB24 H
IcZ2-259 ALL CHM ALL BB25 H
IcZ2-260 HYE COE COE BB26 H
IcZ2-261 H IBu H BB27 H
IcZ2-262 Me Hex NPR BB28 H
IcZ2-263 Et EOE H BB29 H
IcZ2-264 Bu Oct IPR BB30 H
IcZ2-265 TBu TBu TBu BB31 H
IcZ2-266 Hex ALL H BB32 H
IcZ2-267 Oct TBu Et BB33 H
IcZ2-268 2EH NH2 H BB34 H
IcZ2-269 CHM Bu Bu BB35 H
IcZ2-270 CH CBM H BB36 H
IcZ2-271 PH PH PH BB37 H
IcZ2-272 BZ COM H BB38 H
IcZ2-273 NPR Bu Me BB39 H
IcZ2-274 IPR CBA CBA BB40 H
IcZ2-275 IBu COE H BB41 H
IcZ2-276 EOE Me Me BB42 H
IcZ2-277 ALL CBA H BB43 H
IcZ2-278 HYE Et Et BB44 H
IcZ2-279 H H H BB45 H
IcZ2-280 Me HYE HYE BB46 H
[ Table 22Z2]
TABLE 22Z2
RO13Z2 RN13Z2 RN23Z2 Ba1Z2Ba2Z2 R1Z2
IcZ2-281 Et BZ BZ BB47 H
IcZ2-282 Bu Me H BB48 H
IcZ2-283 TBu CBA IPR BB49 H
IcZ2-284 Hex NPR NPR BB50 H
IcZ2-285 Oct Et H BB51 H
IcZ2-286 2EH COE NPR BB52 H
IcZ2-287 CHM CH CH BB53 H
IcZ2-288 CH PH H BB54 H
IcZ2-289 PH COM Et BB55 H
IcZ2-290 BZ IPR IPR BB56 H
IcZ2-291 NPR Bu H BB57 H
IcZ2-292 IPR CBM Me BB58 H
IcZ2-293 IBu IBu IBu BB59 H
IcZ2-294 EOE TBu H BB60 H
IcZ2-295 ALL NH2 COM BB1 H
IcZ2-296 HYE CHM CHM BB19 H
[ Table 27Z2]
TABLE 27Z2
RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2 RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2
IaZ2-224 NA1 NA1 BB1 H IaZ2-264 HHk11 HHk11 BB8 H
IaZ2-225 HHk8 HHk8 BB1 H IaZ2-265 H H BB11 H
IaZ2-226 NA2 NA2 BB1 H IaZ2-266 Me Me BB11 H
IaZ2-227 HHk7 HHk7 BB1 H IaZ2-267 Et Et BB11 H
IaZ2-228 HH37 HH37 BB1 H IaZ2-268 Bu Bu BB11 H
IaZ2-229 HHk6 HHk6 BB1 H IaZ2-269 TBu TBu BB11 H
IaZ2-230 NA3 NA3 BB1 H IaZ2-270 Hex Hex BB11 H
IaZ2-231 HHJ2 HHJ2 BB1 H IaZ2-271 Oct Oct BB11 H
IaZ2-232 HHk11 HHk11 BB1 H IaZ2-272 2EH 2EH BB11 H
IaZ2-233 NA1 NA1 BB6 H IaZ2-273 CH CH BB11 H
IaZ2-234 HHk8 HHk8 BB6 H IaZ2-274 PH PH BB11 H
IaZ2-235 NA2 NA2 BB6 H IaZ2-275 BZ BZ BB11 H
IaZ2-236 HHk7 HHk7 BB6 H IaZ2-276 EOE EOE BB11 H
IaZ2-237 HH37 HH37 BB6 H IaZ2-277 ALL ALL BB11 H
IaZ2-238 HHk6 HHk6 BB6 H IaZ2-278 HYE HYE BB11 H
IaZ2-239 NA3 NA3 BB6 H IaZ2-279 NA1 NA1 BB11 H
IaZ2-240 HHJ2 HHJ2 BB6 H IaZ2-280 HHk8 HHk8 BB11 H
IaZ2-241 HHk11 HHk11 BB6 H IaZ2-281 NA2 NA2 BB11 H
IaZ2-242 H H BB8 H IaZ2-282 HHk7 HHk7 BB11 H
IaZ2-243 Me Me BB8 H IaZ2-283 HH37 HH37 BB11 H
IaZ2-244 Et Et BB8 H IaZ2-284 HHk6 HHk6 BB11 H
IaZ2-245 Bu Bu BB8 H IaZ2-285 NA3 NA3 BB11 H
IaZ2-246 TBu TBu BB8 H IaZ2-286 HHJ2 HHJ2 BB11 H
IaZ2-247 Oct Oct BB8 H IaZ2-287 HHk11 HHk11 BB11 H
IaZ2-248 2EH 2EH BB8 H IaZ2-288 H H BB14 H
IaZ2-249 CHM CHM BB8 H IaZ2-289 Et Et BB14 H
IaZ2-250 CH CH BB8 H IaZ2-290 Bu Bu BB14 H
IaZ2-251 PH PH BB8 H IaZ2-291 TBu TBu BB14 H
IaZ2-252 BZ BZ BB8 H IaZ2-292 Hex Hex BB14 H
IaZ2-253 EOE EOE BB8 H IaZ2-293 Oct Oct BB14 H
IaZ2-254 ALL ALL BB8 H IaZ2-294 2EH 2EH BB14 H
IaZ2-255 HYE HYE BB8 H IaZ2-295 CHM CHM BB14 H
IaZ2-256 NA1 NA1 BB8 H IaZ2-296 CH CH BB14 H
IaZ2-257 HHk8 HHk8 BB8 H IaZ2-297 PH PH BB14 H
IaZ2-258 NA2 NA2 BB8 H IaZ2-298 EOE EOE BB14 H
IaZ2-259 HHk7 HHk7 BB8 H IaZ2-299 ALL ALL BB14 H
IaZ2-260 HH37 HH37 BB8 H IaZ2-300 HYE HYE BB14 H
IaZ2-261 HHk6 HHk6 BB8 H IaZ2-301 NA1 NA1 BB14 H
IaZ2-262 NA3 NA3 BB8 H IaZ2-302 HHk8 HHk8 BB14 H
IaZ2-263 HHJ2 HHJ2 BB8 H IaZ2-303 NA2 NA2 BB14 H
[ Table 28Z2]
TABLE 28Z2
RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2 RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2
IaZ2-304 HHk7 HHk7 BB14 H IaZ2-344 Bu Bu BB58 H
IaZ2-305 HH37 HH37 BB14 H IaZ2-345 TBu TBu BB58 H
IaZ2-306 HHk6 HHk6 BB14 H IaZ2-346 Hex Hex BB58 H
IaZ2-307 NA3 NA3 BB14 H IaZ2-347 Oct Oct BB58 H
IaZ2-308 HHJ2 HHJ2 BB14 H IaZ2-348 2EH 2EH BB58 H
IaZ2-309 HHk11 HHk11 BB14 H IaZ2-349 CHM CHM BB58 H
IaZ2-310 NA1 NA1 BB19 H IaZ2-350 CH CH BB58 H
IaZ2-311 HHk8 HHk8 BB19 H IaZ2-351 PH PH BB58 H
IaZ2-312 NA2 NA2 BB19 H IaZ2-352 BZ BZ BB58 H
IaZ2-313 HHk7 HHk7 BB19 H IaZ2-353 EOE EOE BB58 H
IaZ2-314 HH37 HH37 BB19 H IaZ2-354 ALL ALL BB58 H
IaZ2-315 HHk6 HHk6 BB19 H IaZ2-355 HYE HYE BB58 H
IaZ2-316 NA3 NA3 BB19 H IaZ2-356 NA1 NA1 BB58 H
IaZ2-317 HHJ2 HHJ2 BB19 H IaZ2-357 HHk8 HHk8 BB58 H
IaZ2-318 HHk11 HHk11 BB19 H IaZ2-358 NA2 NA2 BB58 H
IaZ2-319 H H BB37 H IaZ2-359 HHk7 HHk7 BB58 H
IaZ2-320 Me Me BB37 H IaZ2-360 HH37 HH37 BB58 H
IaZ2-321 Et Et BB37 H IaZ2-361 HHk6 HHk6 BB58 H
IaZ2-322 Bu Bu BB37 H IaZ2-362 NA3 NA3 BB58 H
IaZ2-323 TBu TBu BB37 H IaZ2-363 HHJ2 HHJ2 BB58 H
IaZ2-324 Hex Hex BB37 H IaZ2-364 HHk11 HHk11 BB58 H
IaZ2-325 Oct Oct BB37 H IaZ2-365 H H BBJ2 H
IaZ2-326 2EH 2EH BB37 H IaZ2-366 Me Me BBJ2 H
IaZ2-327 CHM CHM BB37 H IaZ2-367 Et Et BBJ2 H
IaZ2-328 CH CH BB37 H IaZ2-368 Bu Bu BBJ2 H
IaZ2-329 PH PH BB37 H IaZ2-369 TBu TBu BBJ2 H
IaZ2-330 BZ BZ BB37 H IaZ2-370 Hex Hex BBJ2 H
IaZ2-331 ALL ALL BB37 H IaZ2-371 Oct Oct BBJ2 H
IaZ2-332 HYE HYE BB37 H IaZ2-372 2EH 2EH BBJ2 H
IaZ2-333 NA1 NA1 BB37 H IaZ2-373 CHM CHM BBJ2 H
IaZ2-334 HHk8 HHk8 BB37 H IaZ2-374 CH CH BBJ2 H
IaZ2-335 NA2 NA2 BB37 H IaZ2-375 PH PH BBJ2 H
IaZ2-336 HHk7 HHk7 BB37 H IaZ2-376 BZ BZ BBJ2 H
IaZ2-337 HH37 HH37 BB37 H IaZ2-377 EOE EOE BBJ2 H
IaZ2-338 HHk6 HHk6 BB37 H IaZ2-378 ALL ALL BBJ2 H
IaZ2-339 NA3 NA3 BB37 H IaZ2-379 HYE HYE BBJ2 H
IaZ2-340 HHJ2 HHJ2 BB37 H IaZ2-380 NA1 NA1 BBJ2 H
IaZ2-341 HHk11 HHk11 BB37 H IaZ2-381 HHk8 HHk8 BBJ2 H
IaZ2-342 Me Me BB58 H IaZ2-382 NA2 NA2 BBJ2 H
IaZ2-343 Et Et BB58 H IaZ2-383 HHk7 HHk7 BBJ2 H
[ Table 29Z2]
TABLE 29Z2
RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2 RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2
IaZ2-384 HH37 HH37 BBJ2 H IaZ2-424 BZ BZ BBO10 H
IaZ2-385 HHk6 HHk6 BBJ2 H IaZ2-425 EOE EOE BBO10 H
IaZ2-386 NA3 NA3 BBJ2 H IaZ2-426 ALL ALL BBO10 H
IaZ2-387 HHJ2 HHJ2 BBJ2 H IaZ2-427 HYE HYE BBO10 H
IaZ2-388 HHk11 HHk11 BBJ2 H IaZ2-428 NA1 NA1 BBO10 H
IaZ2-389 H H BBO8 H IaZ2-429 HHk8 HHk8 BBO10 H
IaZ2-390 Me Me BBO8 H IaZ2-430 NA2 NA2 BBO10 H
IaZ2-391 Et Et BBO8 H IaZ2-431 HHk7 HHk7 BBO10 H
IaZ2-392 Bu Bu BBO8 H IaZ2-432 HH37 HH37 BBO10 H
IaZ2-393 TBu TBu BBO8 H IaZ2-433 HHk6 HHk6 BBO10 H
IaZ2-394 Hex Hex BBO8 H IaZ2-434 NA3 NA3 BBO10 H
IaZ2-395 Oct Oct BBO8 H IaZ2-435 HHJ2 HHJ2 BBO10 H
IaZ2-396 2EH 2EH BBO8 H IaZ2-436 HHk11 HHk11 BBO10 H
IaZ2-397 CHM CHM BBO8 H IaZ2-437 HHf1 HHf1 BB2 H
IaZ2-398 CH CH BBO8 H IaZ2-438 HH55 HH55 BB3 H
IaZ2-399 PH PH BBO8 H IaZ2-439 HHh8 HHh8 BB4 H
IaZ2-400 BZ BZ BBO8 H IaZ2-440 HHf5 HHf5 BB5 H
IaZ2-401 EOE EOE BBO8 H IaZ2-441 HH83 HH83 BB7 H
IaZ2-402 ALL ALL BBO8 H IaZ2-442 HH58 HH58 BB9 H
IaZ2-403 HYE HYE BBO8 H IaZ2-443 HHf11 HHf11 BB10 H
IaZ2-404 NA1 NA1 BBO8 H IaZ2-444 HH34 HH34 BB12 H
IaZ2-405 HHk8 HHk8 BBO8 H IaZ2-445 HH80 HH80 BB13 H
IaZ2-406 NA2 NA2 BBO8 H IaZ2-446 HHb3 HHb3 BB15 H
IaZ2-407 HHk7 HHk7 BBO8 H IaZ2-447 HH13 HH13 BB16 H
IaZ2-408 HH37 HH37 BBO8 H IaZ2-448 HH81 HH81 BB17 H
IaZ2-409 HHk6 HHk6 BBO8 H IaZ2-449 HH49 HH49 BB18 H
IaZ2-410 NA3 NA3 BBO8 H IaZ2-450 HHk6 HHk6 BB20 H
IaZ2-411 HHJ2 HHJ2 BBO8 H IaZ2-451 HHk7 HHk7 BB21 H
IaZ2-412 HHk11 HHk11 BBO8 H IaZ2-452 HHJ2 HHJ2 BB22 H
IaZ2-413 H H BBO10 H IaZ2-453 HH28 HH28 BB23 H
IaZ2-414 Me Me BBO10 H IaZ2-454 HHd6 HHd6 BB24 H
IaZ2-415 Et Et BBO10 H IaZ2-455 HH37 HH37 BB25 H
IaZ2-416 Bu Bu BBO10 H IaZ2-456 HH43 HH43 BB26 H
IaZ2-417 TBu TBu BBO10 H IaZ2-457 NA4 NA4 BB27 H
IaZ2-418 Hex Hex BBO10 H IaZ2-458 HH40 HH40 BB28 H
IaZ2-419 Oct Oct BBO10 H IaZ2-459 HHg5 HHg5 BB29 H
IaZ2-420 2EH 2EH BBO10 H IaZ2-460 HHk3 HHk3 BB30 H
IaZ2-421 CHM CHM BBO10 H IaZ2-461 HHk5 HHk5 BB31 H
IaZ2-422 CH CH BBO10 H IaZ2-462 HH76 HH76 BB32 H
IaZ2-423 PH PH BBO10 H IaZ2-463 HH78 HH78 BB33 H
[ Table 30Z2]
TABLE 30Z2
RO11Z2 RO12Z2 Ba1Z2Ba2Z2 R1Z2
IaZ2-464 HHJ10 HHJ10 BB34 H
IaZ2-465 HHJ3 HHJ3 BB35 H
IaZ2-466 HHk4 HHk4 BB36 H
IaZ2-467 HHc1 HHc1 BB38 H
IaZ2-468 HH61 HH61 BB39 H
IaZ2-469 HH65 HH65 BB40 H
IaZ2-470 HHg2 HHg2 BB41 H
IaZ2-471 HH69 HH69 BB42 H
IaZ2-472 HHJ4 HHJ4 BB43 H
IaZ2-473 HHi11 HHi11 BB44 H
IaZ2-474 NA2 NA2 BB45 H
IaZ2-475 HHk8 HHk8 BB46 H
IaZ2-476 NA3 NA3 BB47 H
IaZ2-477 HHe4 HHe4 BB48 H
IaZ2-478 HHk1 HHk1 BB49 H
IaZ2-479 HHh1 HHh1 BB50 H
IaZ2-480 HHj19 HHj19 BB51 H
IaZ2-481 HHk11 HHk11 BB52 H
IaZ2-482 HHh4 HHh4 BB53 H
IaZ2-483 HH22 HH22 BB54 H
IaZ2-484 HHj10 HHj10 BB55 H
IaZ2-485 HH36 HH36 BB56 H
IaZ2-486 NA5 NA5 BB57 H
IaZ2-487 NA1 NA1 BB59 H
IaZ2-488 HHf14 HHf14 BB60 H
IaZ2-489 HH35 HH35 BBI1 H
IaZ2-490 HHg1 HHg1 BBD1 H
IaZ2-491 HH9 HH9 BBK2 H
IaZ2-492 HHa2 HHa2 BBK3 H
IaZ2-493 HHj17 HHj17 BBK4 H
IaZ2-494 HH46 HH46 BBK14 H
[ Table 31Z2]
TABLE 31Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2 RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-317 HHk8 H HHk8 H BB1 H IbZ2-357 NA3 NA3 NA3 NA3 BB6 H
IbZ2-318 HHk7 H HHk7 H BB1 H IbZ2-358 HHJ2 HHJ2 HHJ2 HHJ2 BB6 H
IbZ2-319 HH37 H HH37 H BB1 H IbZ2-359 HHk11 HHk11 HHk11 HHk11 BB6 H
IbZ2-320 HHk6 H HHk6 H BB1 H IbZ2-360 NA1 Me NA1 Me BB6 H
IbZ2-321 NA3 H NA3 H BB1 H IbZ2-361 HHk8 Me HHk8 Me BB6 H
IbZ2-322 HHJ2 H HHJ2 H BB1 H IbZ2-362 NA2 Me NA2 Me BB6 H
IbZ2-323 HHk11 H HHk11 H BB1 H IbZ2-363 HHk7 Me HHk7 Me BB6 H
IbZ2-324 NA1 NA1 NA1 NA1 BB1 H IbZ2-364 HH37 Me HH37 Me BB6 H
IbZ2-325 HHk8 HHk8 HHk8 HHk8 BB1 H IbZ2-365 HHk6 Me HHk6 Me BB6 H
IbZ2-326 NA2 NA2 NA2 NA2 BB1 H IbZ2-366 NA3 Me NA3 Me BB6 H
IbZ2-327 HHk7 HHk7 HHk7 HHk7 BB1 H IbZ2-367 HHJ2 Me HHJ2 Me BB6 H
IbZ2-328 HH37 HH37 HH37 HH37 BB1 H IbZ2-368 HHk11 Me HHk11 Me BB6 H
IbZ2-329 HHk6 HHk6 HHk6 HHk6 BB1 H IbZ2-369 H H H H BB8 H
IbZ2-330 NA3 NA3 NA3 NA3 BB1 H IbZ2-370 Me H Me H BB8 H
IbZ2-331 HHJ2 HHJ2 HHJ2 HHJ2 BB1 H IbZ2-371 Et H Et H BB8 H
IbZ2-332 HHk11 HHk11 HHk11 HHk11 BB1 H IbZ2-372 PH H PH H BB8 H
IbZ2-333 NA1 Me NA1 Me BB1 H IbZ2-373 Bu H Bu H BB8 H
IbZ2-334 HHk8 Me HHk8 Me BB1 H IbZ2-374 TBu H TBu H BB8 H
IbZ2-335 NA2 Me NA2 Me BB1 H IbZ2-375 Hex H Hex H BB8 H
IbZ2-336 HHk7 Me HHk7 Me BB1 H IbZ2-376 Oct H Oct H BB8 H
IbZ2-337 HH37 Me HH37 Me BB1 H IbZ2-377 2EH H 2EH H BB8 H
IbZ2-338 HHk6 Me HHk6 Me BB1 H IbZ2-378 CHM H CHM H BB8 H
IbZ2-339 NA3 Me NA3 Me BB1 H IbZ2-379 CH H CH H BB8 H
IbZ2-340 HHJ2 Me HHJ2 Me BB1 H IbZ2-380 BZ H BZ H BB8 H
IbZ2-341 HHk11 Me HHk11 Me BB1 H IbZ2-381 EOE H EOE H BB8 H
IbZ2-342 NA1 H NA1 H BB6 H IbZ2-382 ALL H ALL H BB8 H
IbZ2-343 HHk8 H HHk8 H BB6 H IbZ2-383 NH2 H NH2 H BB8 H
IbZ2-344 NA2 H NA2 H BB6 H IbZ2-384 CBM H CBM H BB8 H
IbZ2-345 HHk7 H HHk7 H BB6 H IbZ2-385 COM H COM H BB8 H
IbZ2-346 HH37 H HH37 H BB6 H IbZ2-386 COE H COE H BB8 H
IbZ2-347 HHk6 H HHk6 H BB6 H IbZ2-387 CBA H CBA H BB8 H
IbZ2-348 NA3 H NA3 H BB6 H IbZ2-388 HYE H HYE H BB8 H
IbZ2-349 HHJ2 H HHJ2 H BB6 H IbZ2-389 HHk8 H HHk8 H BB8 H
IbZ2-350 HHk11 H HHk11 H BB6 H IbZ2-390 NA2 H NA2 H BB8 H
IbZ2-351 NA1 NA1 NA1 NA1 BB6 H IbZ2-391 HHk7 H HHk7 H BB8 H
IbZ2-352 HHk8 HHk8 HHk8 HHk8 BB6 H IbZ2-392 HH37 H HH37 H BB8 H
IbZ2-353 NA2 NA2 NA2 NA2 BB6 H IbZ2-393 HHk6 H HHk6 H BB8 H
IbZ2-354 HHk7 HHk7 HHk7 HHk7 BB6 H IbZ2-394 NA3 H NA3 H BB8 H
IbZ2-355 HH37 HH37 HH37 HH37 BB6 H IbZ2-395 HHJ2 H HHJ2 H BB8 H
IbZ2-356 HHk6 HHk6 HHk6 HHk6 BB6 H IbZ2-396 HHk11 H HHk11 H BB8 H
[ Table 32Z2]
TABLE 32Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2 RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-397 Me Me Me Me BB8 H IbZ2-437 NA1 H NA1 H BB11 H
IbZ2-398 PH PH PH PH BB8 H IbZ2-438 HHk8 H HHk8 H BB11 H
IbZ2-399 NA1 NA1 NA1 NA1 BB8 H IbZ2-439 NA2 H NA2 H BB11 H
IbZ2-400 HHk8 HHk8 HHk8 HHk8 BB8 H IbZ2-440 HHk7 H HHk7 H BB11 H
IbZ2-401 NA2 NA2 NA2 NA2 BB8 H IbZ2-441 HH37 H HH37 H BB11 H
IbZ2-402 HHk7 HHk7 HHk7 HHk7 BB8 H IbZ2-442 HHk6 H HHk6 H BB11 H
IbZ2-403 HH37 HH37 HH37 HH37 BB8 H IbZ2-443 NA3 H NA3 H BB11 H
IbZ2-404 HHk6 HHk6 HHk6 HHk6 BB8 H IbZ2-444 HHJ2 H HHJ2 H BB11 H
IbZ2-405 NA3 NA3 NA3 NA3 BB8 H IbZ2-445 HHk11 H HHk11 H BB11 H
IbZ2-406 HHJ2 HHJ2 HHJ2 HHJ2 BB8 H IbZ2-446 Me Me Me Me BB11 H
IbZ2-407 HHk11 HHk11 HHk11 HHk11 BB8 H IbZ2-447 PH PH PH PH BB11 H
IbZ2-408 NA1 Me NA1 Me BB8 H IbZ2-448 NA1 NA1 NA1 NA1 BB11 H
IbZ2-409 HHk8 Me HHk8 Me BB8 H IbZ2-449 HHk8 HHk8 HHk8 HHk8 BB11 H
IbZ2-410 NA2 Me NA2 Me BB8 H IbZ2-450 NA2 NA2 NA2 NA2 BB11 H
IbZ2-411 HHk7 Me HHk7 Me BB8 H IbZ2-451 HHk7 HHk7 HHk7 HHk7 BB11 H
IbZ2-412 HH37 Me HH37 Me BB8 H IbZ2-452 HH37 HH37 HH37 HH37 BB11 H
IbZ2-413 HHk6 Me HHk6 Me BB8 H IbZ2-453 HHk6 HHk6 HHk6 HHk6 BB11 H
IbZ2-414 NA3 Me NA3 Me BB8 H IbZ2-454 NA3 NA3 NA3 NA3 BB11 H
IbZ2-415 HHJ2 Me HHJ2 Me BB8 H IbZ2-455 HHJ2 HHJ2 HHJ2 HHJ2 BB11 H
IbZ2-416 HHk11 Me HHk11 Me BB8 H IbZ2-456 HHk11 HHk11 HHk11 HHk11 BB11 H
IbZ2-417 H H H H BB11 H IbZ2-457 NA1 Me NA1 Me BB11 H
IbZ2-418 Me H Me H BB11 H IbZ2-458 HHk8 Me HHk8 Me BB11 H
IbZ2-419 Et H Et H BB11 H IbZ2-459 NA2 Me NA2 Me BB11 H
IbZ2-420 PH H PH H BB11 H IbZ2-460 HHk7 Me HHk7 Me BB11 H
IbZ2-421 Bu H Bu H BB11 H IbZ2-461 HH37 Me HH37 Me BB11 H
IbZ2-422 TBu H TBu H BB11 H IbZ2-462 HHk6 Me HHk6 Me BB11 H
IbZ2-423 Hex H Hex H BB11 H IbZ2-463 NA3 Me NA3 Me BB11 H
IbZ2-424 Oct H Oct H BB11 H IbZ2-464 HHJ2 Me HHJ2 Me BB11 H
IbZ2-425 2EH H 2EH H BB11 H IbZ2-465 HHk11 Me HHk11 Me BB11 H
IbZ2-426 CHM H CHM H BB11 H IbZ2-466 H H H H BB14 H
IbZ2-427 CH H CH H BB11 H IbZ2-467 Me H Me H BB14 H
IbZ2-428 BZ H BZ H BB11 H IbZ2-468 Et H Et H BB14 H
IbZ2-429 EOE H EOE H BB11 H IbZ2-469 PH H PH H BB14 H
IbZ2-430 ALL H ALL H BB11 H IbZ2-470 Bu H Bu H BB14 H
IbZ2-431 NH2 H NH2 H BB11 H IbZ2-471 TBu H TBu H BB14 H
IbZ2-432 CBM H CBM H BB11 H IbZ2-472 Hex H Hex H BB14 H
IbZ2-433 COM H COM H BB11 H IbZ2-473 Oct H Oct H BB14 H
IbZ2-434 COE H COE H BB11 H IbZ2-474 2EH H 2EH H BB14 H
IbZ2-435 CBA H CBA H BB11 H IbZ2-475 CHM H CHM H BB14 H
IbZ2-436 HYE H HYE H BB11 H IbZ2-476 CH H CH H BB14 H
[ Table 33Z2]
TABLE 33Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2 RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-477 BZ H BZ H BB14 H IbZ2-517 HH37 H HH37 H BB19 H
IbZ2-478 EOE H EOE H BB14 H IbZ2-518 HHk6 H HHk6 H BB19 H
IbZ2-479 ALL H ALL H BB14 H IbZ2-519 NA3 H NA3 H BB19 H
IbZ2-480 NH2 H NH2 H BB14 H IbZ2-520 HHJ2 H HHJ2 H BB19 H
IbZ2-481 CBM H CBM H BB14 H IbZ2-521 HHk11 H HHk11 H BB19 H
IbZ2-482 COM H COM H BB14 H IbZ2-522 NA1 NA1 NA1 NA1 BB19 H
IbZ2-483 COE H COE H BB14 H IbZ2-523 HHk8 HHk8 HHk8 HHk8 BB19 H
IbZ2-484 CBA H CBA H BB14 H IbZ2-524 NA2 NA2 NA2 NA2 BB19 H
IbZ2-485 HYE H HYE H BB14 H IbZ2-525 HHk7 HHk7 HHk7 HHk7 BB19 H
IbZ2-486 NA1 H NA1 H BB14 H IbZ2-526 HH37 HH37 HH37 HH37 BB19 H
IbZ2-487 HHk8 H HHk8 H BB14 H IbZ2-527 HHk6 HHk6 HHk6 HHk6 BB19 H
IbZ2-488 NA2 H NA2 H BB14 H IbZ2-528 NA3 NA3 NA3 NA3 BB19 H
IbZ2-489 HHk7 H HHk7 H BB14 H IbZ2-529 HHJ2 HHJ2 HHJ2 HHJ2 BB19 H
IbZ2-490 HH37 H HH37 H BB14 H IbZ2-530 HHk11 HHk11 HHk11 HHk11 BB19 H
IbZ2-491 HHk6 H HHk6 H BB14 H IbZ2-531 NA1 Me NA1 Me BB19 H
IbZ2-492 NA3 H NA3 H BB14 H IbZ2-532 HHk8 Me HHk8 Me BB19 H
IbZ2-493 HHJ2 H HHJ2 H BB14 H IbZ2-533 NA2 Me NA2 Me BB19 H
IbZ2-494 HHk11 H HHk11 H BB14 H IbZ2-534 HHk7 Me HHk7 Me BB19 H
IbZ2-495 Me Me Me Me BB14 H IbZ2-535 HH37 Me HH37 Me BB19 H
IbZ2-496 PH PH PH PH BB14 H IbZ2-536 HHk6 Me HHk6 Me BB19 H
IbZ2-497 NA1 NA1 NA1 NA1 BB14 H IbZ2-537 NA3 Me NA3 Me BB19 H
IbZ2-498 HHk8 HHk8 HHk8 HHk8 BB14 H IbZ2-538 HHJ2 Me HHJ2 Me BB19 H
IbZ2-499 NA2 NA2 NA2 NA2 BB14 H IbZ2-539 HHk11 Me HHk11 Me BB19 H
IbZ2-500 HHk7 HHk7 HHk7 HHk7 BB14 H IbZ2-540 H H H H BB37 H
IbZ2-501 HH37 HH37 HH37 HH37 BB14 H IbZ2-541 Me H Me H BB37 H
IbZ2-502 HHk6 HHk6 HHk6 HHk6 BB14 H IbZ2-542 Et H Et H BB37 H
IbZ2-503 NA3 NA3 NA3 NA3 BB14 H IbZ2-543 PH H PH H BB37 H
IbZ2-504 HHJ2 HHJ2 HHJ2 HHJ2 BB14 H IbZ2-544 Bu H Bu H BB37 H
IbZ2-505 HHk11 HHk11 HHk11 HHk11 BB14 H IbZ2-545 TBu H TBu H BB37 H
IbZ2-506 NA1 Me NA1 Me BB14 H IbZ2-546 Hex H Hex H BB37 H
IbZ2-507 HHk8 Me HHk8 Me BB14 H IbZ2-547 Oct H Oct H BB37 H
IbZ2-508 NA2 Me NA2 Me BB14 H IbZ2-548 2EH H 2EH H BB37 H
IbZ2-509 HHk7 Me HHk7 Me BB14 H IbZ2-549 CHM H CHM H BB37 H
IbZ2-510 HH37 Me HH37 Me BB14 H IbZ2-550 CH H CH H BB37 H
IbZ2-511 HHk6 Me HHk6 Me BB14 H IbZ2-551 EOE H EOE H BB37 H
IbZ2-512 NA3 Me NA3 Me BB14 H IbZ2-552 ALL H ALL H BB37 H
IbZ2-513 HHJ2 Me HHJ2 Me BB14 H IbZ2-553 NH2 H NH2 H BB37 H
IbZ2-514 HHk11 Me HHk11 Me BB14 H IbZ2-554 CBM H CBM H BB37 H
IbZ2-515 HHk8 H HHk8 H BB19 H IbZ2-555 COM H COM H BB37 H
IbZ2-516 HHk7 H HHk7 H BB19 H IbZ2-556 COE H COE H BB37 H
[ Table 34Z2]
TABLE 34Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2 RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-557 CBA H CBA H BB37 H IbZ2-597 CHM H CHM H BB58 H
IbZ2-558 HYE H HYE H BB37 H IbZ2-598 CH H CH H BB58 H
IbZ2-559 NA1 H NA1 H BB37 H IbZ2-599 BZ H BZ H BB58 H
IbZ2-560 HHk8 H HHk8 H BB37 H IbZ2-600 EOE H EOE H BB58 H
IbZ2-561 NA2 H NA2 H BB37 H IbZ2-601 ALL H ALL H BB58 H
IbZ2-562 HHk7 H HHk7 H BB37 H IbZ2-602 NH2 H NH2 H BB58 H
IbZ2-563 HH37 H HH37 H BB37 H IbZ2-603 CBM H CBM H BB58 H
IbZ2-564 HHk6 H HHk6 H BB37 H IbZ2-604 COM H COM H BB58 H
IbZ2-565 NA3 H NA3 H BB37 H IbZ2-605 COE H COE H BB58 H
IbZ2-566 HHJ2 H HHJ2 H BB37 H IbZ2-606 CBA H CBA H BB58 H
IbZ2-567 HHk11 H HHk11 H BB37 H IbZ2-607 HYE H HYE H BB58 H
IbZ2-568 Me Me Me Me BB37 H IbZ2-608 NA1 H NA1 H BB58 H
IbZ2-569 PH PH PH PH BB37 H IbZ2-609 HHk8 H HHk8 H BB58 H
IbZ2-570 NA1 NA1 NA1 NA1 BB37 H IbZ2-610 NA2 H NA2 H BB58 H
IbZ2-571 HHk8 HHk8 HHk8 HHk8 BB37 H IbZ2-611 HHk7 H HHk7 H BB58 H
IbZ2-572 NA2 NA2 NA2 NA2 BB37 H IbZ2-612 HH37 H HH37 H BB58 H
IbZ2-573 HHk7 HHk7 HHk7 HHk7 BB37 H IbZ2-613 HHk6 H HHk6 H BB58 H
IbZ2-574 HH37 HH37 HH37 HH37 BB37 H IbZ2-614 NA3 H NA3 H BB58 H
IbZ2-575 HHk6 HHk6 HHk6 HHk6 BB37 H IbZ2-615 HHJ2 H HHJ2 H BB58 H
IbZ2-576 NA3 NA3 NA3 NA3 BB37 H IbZ2-616 HHk11 H HHk11 H BB58 H
IbZ2-577 HHJ2 HHJ2 HHJ2 HHJ2 BB37 H IbZ2-617 Me Me Me Me BB58 H
IbZ2-578 HHk11 HHk11 HHk11 HHk11 BB37 H IbZ2-618 PH PH PH PH BB58 H
IbZ2-579 NA1 Me NA1 Me BB37 H IbZ2-619 NA1 NA1 NA1 NA1 BB58 H
IbZ2-580 HHk8 Me HHk8 Me BB37 H IbZ2-620 HHk8 HHk8 HHk8 HHk8 BB58 H
IbZ2-581 NA2 Me NA2 Me BB37 H IbZ2-621 NA2 NA2 NA2 NA2 BB58 H
IbZ2-582 HHk7 Me HHk7 Me BB37 H IbZ2-622 HHk7 HHk7 HHk7 HHk7 BB58 H
IbZ2-583 HH37 Me HH37 Me BB37 H IbZ2-623 HH37 HH37 HH37 HH37 BB58 H
IbZ2-584 HHk6 Me HHk6 Me BB37 H IbZ2-624 HHk6 HHk6 HHk6 HHk6 BB58 H
IbZ2-585 NA3 Me NA3 Me BB37 H IbZ2-625 NA3 NA3 NA3 NA3 BB58 H
IbZ2-586 HHJ2 Me HHJ2 Me BB37 H IbZ2-626 HHJ2 HHJ2 HHJ2 HHJ2 BB58 H
IbZ2-587 HHk11 Me HHk11 Me BB37 H IbZ2-627 HHk11 HHk11 HHk11 HHk11 BB58 H
IbZ2-588 H H H H BB58 H IbZ2-628 NA1 Me NA1 Me BB58 H
IbZ2-589 Me H Me H BB58 H IbZ2-629 HHk8 Me HHk8 Me BB58 H
IbZ2-590 Et H Et H BB58 H IbZ2-630 NA2 Me NA2 Me BB58 H
IbZ2-591 PH H PH H BB58 H IbZ2-631 HHk7 Me HHk7 Me BB58 H
IbZ2-592 Bu H Bu H BB58 H IbZ2-632 HH37 Me HH37 Me BB58 H
IbZ2-593 TBu H TBu H BB58 H IbZ2-633 HHk6 Me HHk6 Me BB58 H
IbZ2-594 Hex H Hex H BB58 H IbZ2-634 NA3 Me NA3 Me BB58 H
IbZ2-595 Oct H Oct H BB58 H IbZ2-635 HHJ2 Me HHJ2 Me BB58 H
IbZ2-596 2EH H 2EH H BB58 H IbZ2-636 HHk11 Me HHk11 Me BB58 H
[ Table 35Z2]
TABLE 35Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2 RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-637 H H H H BBJ2 H IbZ2-677 NA1 Me NA1 Me BBJ2 H
IbZ2-638 Me H Me H BBJ2 H IbZ2-678 HHk8 Me HHk8 Me BBJ2 H
IbZ2-639 Et H Et H BBJ2 H IbZ2-679 NA2 Me NA2 Me BBJ2 H
IbZ2-640 PH H PH H BBJ2 H IbZ2-680 HHk7 Me HHk7 Me BBJ2 H
IbZ2-641 Bu H Bu H BBJ2 H IbZ2-681 HH37 Me HH37 Me BBJ2 H
IbZ2-642 TBu H TBu H BBJ2 H IbZ2-682 HHk6 Me HHk6 Me BBJ2 H
IbZ2-643 Hex H Hex H BBJ2 H IbZ2-683 NA3 Me NA3 Me BBJ2 H
IbZ2-644 Oct H Oct H BBJ2 H IbZ2-684 HHJ2 Me HHJ2 Me BBJ2 H
IbZ2-645 2EH H 2EH H BBJ2 H IbZ2-685 HHk11 Me HHk11 Me BBJ2 H
IbZ2-646 CHM H CHM H BBJ2 H IbZ2-686 H H H H BBO8 H
IbZ2-647 CH H CH H BBJ2 H IbZ2-687 Me H Me H BBO8 H
IbZ2-648 BZ H BZ H BBJ2 H IbZ2-688 Et H Et H BBO8 H
IbZ2-649 EOE H EOE H BBJ2 H IbZ2-689 PH H PH H BBO8 H
IbZ2-650 ALL H ALL H BBJ2 H IbZ2-690 Bu H Bu H BBO8 H
IbZ2-651 NH2 H NH2 H BBJ2 H IbZ2-691 TBu H TBu H BBO8 H
IbZ2-652 CBM H CBM H BBJ2 H IbZ2-692 Hex H Hex H BBO8 H
IbZ2-653 COM H COM H BBJ2 H IbZ2-693 Oct H Oct H BBO8 H
IbZ2-654 COE H COE H BBJ2 H IbZ2-694 2EH H 2EH H BBO8 H
IbZ2-655 CBA H CBA H BBJ2 H IbZ2-695 CHM H CHM H BBO8 H
IbZ2-656 HYE H HYE H BBJ2 H IbZ2-696 CH H CH H BBO8 H
IbZ2-657 NA1 H NA1 H BBJ2 H IbZ2-697 BZ H BZ H BBO8 H
IbZ2-658 HHk8 H HHk8 H BBJ2 H IbZ2-698 EOE H EOE H BBO8 H
IbZ2-659 NA2 H NA2 H BBJ2 H IbZ2-699 ALL H ALL H BBO8 H
IbZ2-660 HHk7 H HHk7 H BBJ2 H IbZ2-700 NH2 H NH2 H BBO8 H
IbZ2-661 HH37 H HH37 H BBJ2 H IbZ2-701 CBM H CBM H BBO8 H
IbZ2-662 HHk6 H HHk6 H BBJ2 H IbZ2-702 COM H COM H BBO8 H
IbZ2-663 NA3 H NA3 H BBJ2 H IbZ2-703 COE H COE H BBO8 H
IbZ2-664 HHJ2 H HHJ2 H BBJ2 H IbZ2-704 CBA H CBA H BBO8 H
IbZ2-665 HHk11 H HHk11 H BBJ2 H IbZ2-705 HYE H HYE H BBO8 H
IbZ2-666 Me Me Me Me BBJ2 H IbZ2-706 HHk8 H HHk8 H BBO8 H
IbZ2-667 PH PH PH PH BBJ2 H IbZ2-707 NA2 H NA2 H BBO8 H
IbZ2-668 NA1 NA1 NA1 NA1 BBJ2 H IbZ2-708 HHk7 H HHk7 H BBO8 H
IbZ2-669 HHk8 HHk8 HHk8 HHk8 BBJ2 H IbZ2-709 HH37 H HH37 H BBO8 H
IbZ2-670 NA2 NA2 NA2 NA2 BBJ2 H IbZ2-710 HHk6 H HHk6 H BBO8 H
IbZ2-671 HHk7 HHk7 HHk7 HHk7 BBJ2 H IbZ2-711 NA3 H NA3 H BBO8 H
IbZ2-672 HH37 HH37 HH37 HH37 BBJ2 H IbZ2-712 HHJ2 H HHJ2 H BBO8 H
IbZ2-673 HHk6 HHk6 HHk6 HHk6 BBJ2 H IbZ2-713 HHk11 H HHk11 H BBO8 H
IbZ2-674 NA3 NA3 NA3 NA3 BBJ2 H IbZ2-714 Me Me Me Me BBO8 H
IbZ2-675 HHJ2 HHJ2 HHJ2 HHJ2 BBJ2 H IbZ2-715 PH PH PH PH BBO8 H
IbZ2-676 HHk11 HHk11 HHk11 HHk11 BBJ2 H IbZ2-716 NA1 NA1 NA1 NA1 BBO8 H
[ Table 36Z2]
TABLE 36Z2
RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2 RN11Z2 RN21Z2 RN12Z2 RN22Z2 Ba1Z2Ba2Z2 R1Z2
IbZ2-717 HHk8 HHk8 HHk8 HHk8 BBO8 H IbZ2-757 HHk7 H HHk7 H BBO10 H
IbZ2-718 NA2 NA2 NA2 NA2 BBO8 H IbZ2-758 HH37 H HH37 H BBO10 H
IbZ2-719 HHk7 HHk7 HHk7 HHk7 BBO8 H IbZ2-759 HHk6 H HHk6 H BBO10 H
IbZ2-720 HH37 HH37 HH37 HH37 BBO8 H IbZ2-760 NA3 H NA3 H BBO10 H
IbZ2-721 HHk6 HHk6 HHk6 HHk6 BBO8 H IbZ2-761 HHJ2 H HHJ2 H BBO10 H
IbZ2-722 NA3 NA3 NA3 NA3 BBO8 H IbZ2-762 HHk11 H HHk11 H BBO10 H
IbZ2-723 HHJ2 HHJ2 HHJ2 HHJ2 BBO8 H IbZ2-763 Me Me Me Me BBO10 H
IbZ2-724 HHk11 HHk11 HHk11 HHk11 BBO8 H IbZ2-764 PH PH PH PH BBO10 H
IbZ2-725 NA1 Me NA1 Me BBO8 H IbZ2-765 NA1 NA1 NA1 NA1 BBO10 H
IbZ2-726 HHk8 Me HHk8 Me BBO8 H IbZ2-766 HHk8 HHk8 HHk8 HHk8 BBO10 H
IbZ2-727 NA2 Me NA2 Me BBO8 H IbZ2-767 NA2 NA2 NA2 NA2 BBO10 H
IbZ2-728 HHk7 Me HHk7 Me BBO8 H IbZ2-768 HHk7 HHk7 HHk7 HHk7 BBO10 H
IbZ2-729 HH37 Me HH37 Me BBO8 H IbZ2-769 HH37 HH37 HH37 HH37 BBO10 H
IbZ2-730 HHk6 Me HHk6 Me BBO8 H IbZ2-770 HHk6 HHk6 HHk6 HHk6 BBO10 H
IbZ2-731 NA3 Me NA3 Me BBO8 H IbZ2-771 NA3 NA3 NA3 NA3 BBO10 H
IbZ2-732 HHJ2 Me HHJ2 Me BBO8 H IbZ2-772 HHJ2 HHJ2 HHJ2 HHJ2 BBO10 H
IbZ2-733 HHk11 Me HHk11 Me BBO8 H IbZ2-773 HHk11 HHk11 HHk11 HHk11 BBO10 H
IbZ2-734 H H H H BBO10 H IbZ2-774 NA1 Me NA1 Me BBO10 H
IbZ2-735 Me H Me H BBO10 H IbZ2-775 HHk8 Me HHk8 Me BBO10 H
IbZ2-736 Et H Et H BBO10 H IbZ2-776 NA2 Me NA2 Me BBO10 H
IbZ2-737 PH H PH H BBO10 H IbZ2-777 HHk7 Me HHk7 Me BBO10 H
IbZ2-738 Bu H Bu H BBO10 H IbZ2-778 HH37 Me HH37 Me BBO10 H
IbZ2-739 TBu H TBu H BBO10 H IbZ2-779 HHk6 Me HHk6 Me BBO10 H
IbZ2-740 Hex H Hex H BBO10 H IbZ2-780 NA3 Me NA3 Me BBO10 H
IbZ2-741 Oct H Oct H BBO10 H IbZ2-781 HHJ2 Me HHJ2 Me BBO10 H
IbZ2-742 2EH H 2EH H BBO10 H IbZ2-782 HHk11 Me HHk11 Me BBO10 H
IbZ2-743 CHM H CHM H BBO10 H IbZ2-783 HHj10 H HHj10 H BB2 H
IbZ2-744 CH H CH H BBO10 H IbZ2-784 HHk1 H HHk1 H BB3 H
IbZ2-745 BZ H BZ H BBO10 H IbZ2-785 HH61 H HH61 H BB4 H
IbZ2-746 EOE H EOE H BBO10 H IbZ2-786 HH65 H HH65 H BB5 H
IbZ2-747 ALL H ALL H BBO10 H IbZ2-787 HHk5 H HHk5 H BB7 H
IbZ2-748 NH2 H NH2 H BBO10 H IbZ2-788 HHf14 H HHf14 H BB9 H
IbZ2-749 CBM H CBM H BBO10 H IbZ2-789 HHk6 H HHk6 H BB10 H
IbZ2-750 COM H COM H BBO10 H IbZ2-790 HH37 H HH37 H BB12 H
IbZ2-751 COE H COE H BBO10 H IbZ2-791 HH46 H HH46 H BB13 H
IbZ2-752 CBA H CBA H BBO10 H IbZ2-792 HHk3 H HHk3 H BB15 H
IbZ2-753 HYE H HYE H BBO10 H IbZ2-793 HH22 H HH22 H BB16 H
IbZ2-754 NA1 H NA1 H BBO10 H IbZ2-794 HHc1 H HHc1 H BB17 H
IbZ2-755 HHk8 H HHk8 H BBO10 H IbZ2-795 NA4 H NA4 H BB18 H
IbZ2-756 NA2 H NA2 H BBO10 H IbZ2-796 HH40 H HH40 H BB20 H
[ Table 37Z2]
TABLE 37Z2
Figure BDA0003121580680001641
For example, compound IaZ2-1 is a compound represented by formula (IaZ 2-1).
Figure BDA0003121580680001642
Preferably IaZ2-1 to IaZ2-165, IaZ2-223 to IaZ2-494, compound IbZ2-1 to IbZ2-248, compound IbZ2-311 to IbZ2-840, compound IcZ2-1 to IcZ2-234, more preferably IaZ2-1 to IaZ2-165, IaZ2-223 to IaZ2-436, compound IbZ2-1 to IbZ2-248, compound IbZ2-311 to IbZ2-782, compound IcZ2-1 to IcZ2-234,
More preferred are compound IaZ2-1 to compound IaZ2-165, compound IbZ2-1 to compound IbZ2-248, and compound IcZ2-1 to compound IcZ2-234, still more preferred are compound IaZ2-1 to compound IaZ2-111, compound IbZ2-1 to compound IbZ2-248, and compound IcZ2-1 to compound IcZ2-234, and particularly preferred are compound IaZ2-1 to compound IaZ2-54, and compound IbZ2-1 to compound IbZ 2-186.
Specific examples of the compound IZ2 include: tables 1Z2, 2Z2, 3Z2, 4Z2, 5Z2, 6Z2, 7Z2, 8Z2, 9Z2, 10Z2, 11Z2, 12Z2, 13Z2, 14Z2, 15Z2, 16Z2, 17Z2, 18Z2, 19Z2, 20Z2, 21Z2, 22Z2, 27Z2, 28Z2, 29Z2, 30Z2, 31Z2, 32Z2, 33Z2, 34Z2, 35Z2, 36Z2, and 37Z2 show that 1 to 3 hydrogen atoms contained in the compound are replaced with — SO3M or-CO2M is substituted. For example, a compound having 1 to 3 sulfo groups bonded to compound IaZ2-1 of table 1Z2 is represented by the following structure. Wherein, in the formula, - (SO)3H) Represents a compound IaZ2-1 in which any hydrogen atom in table 1Z2 is substituted.
Figure BDA0003121580680001651
Preferably, 1 to 3-SO groups are bonded to the compound IaZ2-1 to the compound IaZ2-165, the compound IaZ2-223 to the compound IaZ2-494, the compound IbZ2-1 to the compound IbZ2-248, the compound IbZ2-311 to the compound IbZ2-840, and the compound IcZ2-1 to the compound IcZ2-234 3M or-CO2A compound formed by the reaction of M,
more preferably, the compound is one selected from the group consisting of compounds IaZ2-1 to IaZ2-165, IaZ2-223 to IaZ2-436, and IbZ2-1 to IbZ2-248Compounds IbZ 2-311-IbZ 2-782, compounds IcZ 2-1-IcZ 2-234, to which 1-3-SO groups are bonded3M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IaZ2-1 to the compound IaZ2-165, the compound IbZ2-1 to the compound IbZ2-248, and the compound IcZ2-1 to the compound IcZ2-2343M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IaZ2-1 to the compound IaZ2-111, the compound IbZ2-1 to the compound IbZ2-248, and the compound IcZ2-1 to the compound IcZ2-2343M or-CO2A compound formed by the reaction of M,
particularly preferably, 1 to 3-SO groups are bonded to the compound IaZ2-1 to the compound IaZ2-54 and the compound IbZ2-1 to the compound IbZ2-1863M or-CO2M, or a salt thereof.
As a bond with-CO2Examples of the compound of M include compounds wherein 2-CO-CO groups are bonded to compound IbZ2-2, compound IbZ2-3, compound IbZ2-4, compound IbZ2-12, compound IbZ2-126, compound IbZ2-127, compound IbZ2-687, compound IbZ2-370, and the like2Among the compounds of H, particularly, compounds IbZ2 to 317, compounds IbZ2 to 318, compounds IbZ2 to 319, compounds IbZ2 to 320, compounds IbZ2 to 515, compounds IbZ2 to 516, compounds IbZ2 to 706, compounds IbZ2 to 389 and the like are particularly preferable.
Figure BDA0003121580680001671
As the compound (IZ2), the following compounds are preferable: in the formula (IZ2), RCO1Z2And RCO1Z2Are identical radicals, RO1Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, RN1Z2And RN2Z2Independently of one another, a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-CON(R102Z2)2Or may have a structure selected from the group consisting of-SO3M and-CO2M in the groupA substituent group of a hydrocarbon group having 1 to 20 carbon atoms, R1Z2Is a hydrogen atom and may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,R2Z2~R5Z2Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z2)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z2、-O-R102Z2、-SO3M or-CO2M,R102Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 20 carbon atoms as a substituent in the group consisting of M,
R101Z2may have a structure selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 20 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
RCO1Z2and RCO1Z2Are identical radicals, RO1Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO 3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, RN1Z2And RN2Z2Independently of one another, a hydrogen atom, -CO-R102Z2、-CON(R102Z2)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R1Z2Is a hydrogen atom, R2Z2~R5Z2Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z2)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z2、-O-R102Z2、-SO3M or-CO2M,R102Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R101Z2To be provided withIs selected from-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
RCO1Z2and RCO1Z2Are identical radicals, RO1Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, RN1Z2And RN2Z2Independently of one another, a hydrogen atom, -CO-R102Z2、-CON(R102Z2)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R 1Z2Is a hydrogen atom, R2Z2~R5Z2Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z2)2Nitro, trifluoromethyl, -O-R102Z2、-SO3M or-CO2M,R102Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R101Z2May have a structure selected from the group consisting of-SO3M and-CO2And M is a compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms and M is a hydrogen atom or an alkali metal atom.
For compound IZ2, R1Z2In the case of a hydrogen atom, the compound represented by the formula (pt1Z2) (hereinafter, may be referred to as a phthalonitrile compound) may be produced by reacting a compound represented by the formula (pt2Z2) (hereinafter, may be referred to as an alkoxide compound), and then further reacting the compound represented by the formula (pt3Z2) and the compound represented by the formula (pt4Z2) in the presence of an acid. In addition, R1Z2When not a hydrogen atom, the compound is further reacted with a compound represented by the formula (pt5Z2) to produce a compound IZ 2.
Figure BDA0003121580680001691
In [ formula (pt1Z2), formula (pt2Z2), formula (pt3Z2), formula (pt4Z2), formula (pt5Z2) and formula (IZ2), RCO1Z2、RCO2Z2、R1Z2、R2Z2、R3Z2、R4Z2And R5Z2The same meanings as described above are indicated. R14Z2Represents an alkyl group having 1 to 20 carbon atoms. M1Z2Represents an alkali metal atom.
LG represents a halogen atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group. ]
As R14Z2Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z2Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z2 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z2 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z2, and the compound pt4Z2 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; 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 acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound.
The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z2 used, relative to R1Z2The amount of the compound IZ21 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
When the compound pt5Z2 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1Z2The amount of the compound IZ21 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
The reaction of compound pt5Z2 can generally be carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1Z2The amount of the compound IZ 21 is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z2 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound IZ2 having no sulfo group or-SO3M22In the case of (3), the compound IZ2 can be reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to introduce a sulfo group or-SO3M2
M22Represents an alkali metal atom.
As M22Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
With respect to SO in oleum3The amount of (b) is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and still more preferably 5 to 25 mol based on 21 mol of the compound IZ.
The amount of sulfuric acid used in the oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on 21 moles of the compound IZ.
The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on 21 moles of the compound IZ.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound IZ2 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is filtered to extract the compound IZ 2. Further, the residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After the completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
< Compound IZ3 >)
Compound IZ3 is a compound represented by formula (IZ 3).
Figure BDA0003121580680001721
[ formula (IZ3), R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3Each of which may be bonded to each other to form a ring. R101Z3The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z3Represents a hydrogen atom or an optionally substituted carbonA hydrocarbon group having 1 to 40 atoms or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. R 101Z3、R102Z3And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The number of carbon atoms of the hydrocarbon group is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, and particularly preferably 1 to 10.
R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, further more preferably 1 to 8, and particularly preferably 1 to 5. Wherein A linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable, and a methyl group, an ethyl group, or a tert-butyl group is particularly preferable.
As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, and, Cycloalkyl groups such as 2,2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl are particularly preferable.
As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3Examples of the aromatic hydrocarbon group include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, and a homo-tert-butylphenyl groupAromatic hydrocarbon groups such as a trimethylphenyl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 5,6,7, 8-tetrahydro-1-naphthyl group, a 5,6,7, 8-tetrahydro-2-naphthyl group, a fluorenyl group, a phenanthryl group, an anthracenyl group, and a pyrenyl group; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3Examples of the group represented by the above-mentioned groups, which are a combination of the above-mentioned hydrocarbon groups (e.g., chain hydrocarbon groups and alicyclic hydrocarbon groups), include alkyl groups to which 1 or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl groups, cyclopropylethyl groups, cyclobutylmethyl groups, cyclobutylethyl groups, cyclopentylmethyl groups, cyclopentylethyl groups, cyclohexylmethyl groups, 2-methylcyclohexylmethyl groups, cyclohexylethyl groups, and adamantylmethyl groups.
The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbyl group represented may haveAnd (4) a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
Figure BDA0003121580680001761
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl;
a formyl group;
a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
Figure BDA0003121580680001771
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
Figure BDA0003121580680001772
Figure BDA0003121580680001781
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formula);
Figure BDA0003121580680001791
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, N-phenylmethylsulfamoyl, and the like, and groups represented by the following chemical formulae);
Figure BDA0003121580680001801
Figure BDA0003121580680001811
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
Figure BDA0003121580680001812
Figure BDA0003121580680001821
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is an alkali metal, preferably lithium, sodium, potassium); a nitro group; a cyano group; a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
Figure BDA0003121580680001822
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
Figure BDA0003121580680001831
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
Figure BDA0003121580680001842
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, or a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3、-CO-S-CH2-CH2-CH2-CH3or a thiocarbonyl group, -CO-S-C, bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) 6H5A thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms; a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
Figure BDA0003121580680001851
-NRCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
Figure BDA0003121580680001861
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octyl group) Sulfamoyl) and the like, and the R groups may be the same or different from each other and may be bonded to each other to form a ring);
Figure BDA0003121580680001871
a group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
Figure BDA0003121580680001872
Figure BDA0003121580680001881
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR 3(wherein R is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above)) Or a derivative thereof (e.g., a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R's may be the same or different from each other, and may be bonded to each other to form a ring); and so on.
Examples of the substituent having a valence of 2 include an oxo group, a thioxo 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. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably hydrogenAn atom. ) (ii) a A nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof;
a hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms;
A hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent;
a hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine;
an oxo group.
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a hydroxyl group; fluorine atom, chlorine atom, bromine atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
A carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbon group having 1 to 40 carbon atoms and having a substituent represented by the formula (I) includes a hydrocarbon group having 1 to 40 carbon atoms and having a substituent having a valence of 1 or 2, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, and a group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which are a combination of hydrocarbon groups,
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups having 1 to 20 carbon atoms having a substituent of group s1,
Particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 1 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The heterocyclic group may be a monocyclic or monocyclic ringAnd polycyclic, preferably heterocyclic, containing a heteroatom as a ring member. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include:
monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole;
a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine;
A fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane; bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone; five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran;
fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole, chroman and isochroman; fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include:
five-membered ring system saturated heterocycles such as dithiolane; saturated heterocyclic rings of six-membered ring systems such as thiacyclohexane, 1, 3-dithiane, 2-methyl-1, 3-dithiane and the like; a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran); fused bicyclic heterocycles such as benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include:
monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone; a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole);
fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
Figure BDA0003121580680001921
The above heterocyclic group may be R1Z3~R5Z32 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1Z3~R5Z3The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
Figure BDA0003121580680001922
The bonding position of the heterocycle is a portion where any hydrogen atom contained in each ring is removed.
R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The heterocyclic group represented may have a substituent. Examples of the substituent include1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbon group may have the same substituent as the substituent. In addition, in the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom.
Preferred examples of the substituent include1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The preferable examples of the substituents which the hydrocarbon group may have are the same. As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The heterocyclic group having a substituent represented by the formula (i) includes a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s 2.
The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. As for the above-mentioned first substituent, another substituent (second substituent) may be bonded to the hydrocarbon group contained in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3Of (a) is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, -SO3M、-CO2M is explained.
as-CO-R102Z3Examples thereof include a formyl group; a carbonyl group (e.g., a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (e.g., a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, a undecanoyl group, a dodecanoyl group, a benzoyl group, and a group represented by the above chemical formula, and the like, and the carbonyl group corresponding to-CO-R-in the compounds represented by tables 1Z3 to 6Z3 102Z3Preferable examples of the group(s) include a carbonyl group (more preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a group corresponding to-CO-R in the compounds shown in tables 1Z3 to 6Z3102Z3And the like.
as-COO-R101Z3Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl, icosyl-L-butyloxycarbonylAn alkoxycarbonyl group having a C1-40 (preferably C1-20) hydrocarbon group or a derivative thereof (e.g., a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group (preferably an octylsulfamoyl group) having C1-10) bonded thereto such as an alkyloxycarbonyl group or the like, and a group represented by the above chemical formula, and a compound corresponding to-COO-R in tables 1Z3 to 6Z3 102Z3Preferred examples of the group (b) include oxycarbonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded and compounds represented by tables 1Z3 to 6Z3 corresponding to-COO-R102Z3And the like.
as-OCO-R102Z3Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy and the like, carbonyloxy (having 2 to 41 carbon atoms in the case where the carbonyloxy group is an acyloxy group), carbonyloxy having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) bonded to a group represented by the above formula) and the like, And the compounds shown in tables 1Z3 to 6Z3 correspond to-OCO-R102Z3Preferable examples of the group(s) include a carbonyloxy group (more preferably 2 to 12 carbon atoms when the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z3 to 6Z3 corresponding to-OCO-R 102Z3And the like.
as-COCO-R102Z3Examples thereof include methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) hexyloxalyl, heptyloxalyl, octyloxalyl, nonyloxalylOxalyl groups in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as oxalyl group, decyloxyl group, undecyloxalyl group, dodecyloxalyl group, eicosanyl group, cyclopentyloxalyl group, cyclohexyloxalyl group, phenyloxalyl group, p-tolyloxalyl group, and the group represented by the above chemical formula), and compounds represented by tables 1Z3 to 6Z3 corresponding to-COCO-R102Z3And the like.
as-O-R102Z3There may be mentioned a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 5-dimethylphenyloxy, 2, 6-dimethylphenyloxy, 3, 4-dimethylphenyloxy, 3, 5-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 3-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 4-di-yloxy, 2-di-methyl-1-phenylethoxy, 2, 4-di-methyl, and mixtures thereof, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, examples of the oxygen group include an oxygen group having a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like bonded thereto, such as a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the above chemical formula), and compounds shown in tables 1Z3 to 6Z3, which correspond to — O — R. 102Z3Preferable examples of the group (b) include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded and groups shown in tables 1Z3 to 6Z3In the compounds shown, the corresponding-O-R102Z3And the like.
as-SO2-R101Z3Examples thereof include sulfonyl groups in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof by a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) is bonded, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl) hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, eicosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group, etc., and groups represented by the above chemical formulae, and sulfonyl groups corresponding to-SO-in the compounds represented by tables 1Z3 to 6Z32-R102Z3Preferable examples of the group (b) include a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded and a group corresponding to-SO in the compounds represented by tables 1Z3 to 6Z3 2-R102Z3And the like.
as-SO2N(R102Z3)2Examples thereof include: a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl, N-phenylsulfamoyl, etc., and a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula, or a derivative thereof Sulfamoyl groups substituted with a raw group (e.g., a group derived from carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group)), and the like, and the amino groups shown in tables 1Z3 to 6Z3Corresponding to-SO in the compound (A) of2NH(R102Z3X) (wherein, R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above), etc.;
N, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylsulfamoyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diethylsulfamoyl, N, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylmethylsulfamoyl, N-phenylmethylsulfamoyl, N-diphenylsulfamoyl and the like, and sulfamoyl groups represented by the above chemical formulae and the like substituted with a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl) and the like, and the compounds represented by tables 1Z3 to 6Z3 correspond to those of the compounds represented by tables 1Z3 to 6Z3 -SO 2N(R102Z3X)2(wherein, R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above) and the like,
preferred examples thereof include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds represented by tables 1Z3 to 6Z3, which correspond to-SO2N(R102Z3)2And the like.
as-CON (R)102Z3)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoylA hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, an N-isopropylcarbamoyl group, an N-butylcarbamoyl group, an N-isobutylcarbamoyl group, an N-sec-butylcarbamoyl group, an N-tert-butylcarbamoyl group, an N-pentylcarbamoyl group, an N- (1-ethylpropyl) carbamoyl group, an N-hexylcarbamoyl group, an N- (2-ethyl) hexylcarbamoyl group, an N-heptylcarbamoyl group, an N-octylcarbamoyl group, an N-nonylcarbamoyl group, an N-decylcarbamoyl group, an N-undecylcarbamoyl group, an N-dodecylcarbamoyl group, an N-eicosylcarbamoyl group, an N-phenylcarbamoyl group and the like, and a group represented by the above chemical formula, A carbamoyl group substituted with a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and a compound represented by any of tables 1Z3 to 6Z3, wherein the carbamoyl group corresponds to-CONH (R is R 102Z3X)(R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above), etc.;
n, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-tert-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-diethylcarbamoyl group, N-diisopropylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-isobutylcarbamoyl group, N-di (s-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-di-N-butylcarbamoyl group, N, n, N-dihexylcarbamoyl group, N-di (2-ethyl) hexylcarbamoyl group, N-diheptylcarbamoyl group, N-octylmethylcarbamoyl group, N-dioctylcarbamoyl group, N-dinonylcarbamoyl group, N-decylmethylcarbamoyl group, N-undecylmethylcarbamoyl group, N-dodecylmethylcarbamoyl group, N-eicosylmethylcarbamoyl group, N-phenylmethylcarbamoyl group, N-diphenylcarbamoyl group, etc., and a group represented by the above chemical formula, etc., each having 2 carbon atoms Carbamoyl groups substituted with a hydrocarbyl group having 1 to 40 (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl (preferably octylsulfamoyl) having 1 to 10 carbon atoms) and compounds shown in tables 1Z3 to 6Z3 corresponding to-CON (R102Z3X)2(R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z3 to 6Z3 corresponding to-CON (R)102Z3)2And the like.
as-N (R)102Z3)2Examples thereof include:
an amino group; a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom)), such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, an N-tert-butylamino group, an N-pentylamino group, an N-hexylamino group, an N- (2-ethyl) hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-undecylamino group, an N-dodecylamino group, an N-eicosylamino group, an N-phenylamino group, and the like, and a group represented by the above chemical formula, A group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) and the like) and a compound shown in tables 1Z3 to 6Z3 corresponding to-NH (R 102Z3X)(R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above), etc.;
n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-A group derived from a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like, such as a dipentylamino group, an N, N-di (1-ethylpropyl) amino group, an N, N-dihexylamino group, an N, N-di (2-ethyl) hexylamino group, an N, N-diheptylamino group, an N, N-dioctylamino group, an N, N-dinonylamino group, an N, N-decylmethylamino group, an N, N-undecylmethylamino group, an N, N-dodecylmethylamino group, an N, N-eicosylmethylamino group, an N, N-phenylmethylamino group, an N, N-diphenylamino group, or the like, and a group represented by the above chemical formula ) The substituted amino group and the compounds shown in tables 1Z3 to 6Z3 correspond to-N (R) 102Z3X)2(R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above), and the like, and preferably include amino groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and groups corresponding to-N (R) in the compounds shown in tables 1Z3 to 6Z3102Z3)2And the like.
as-NHCO-R102Z3Examples thereof include formylamino; a carbonylamino group (in the case where the carbonylamino group is an acylamino group, the number of carbon atoms is 1 to 40) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as an acetylamino group, a propionylamino group, a butyrylamino group, a 2, 2-dimethylpropionylamino group, a valerylamino group, a hexanoylamino group, (2-ethyl) hexanoylamino group, a heptanoylamino group, an octanoylamino group, a nonanoylamino group, a decanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, a benzoylamino group, and the like, and a group represented by the above-mentioned chemical formula, and-NHCO-R is equivalent to in the compounds shown in tables 1Z3 to 6Z3 102Z3And the like,
preferably, the carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded(in the case where the carbonylamino group is an alkanoylamino group, the number of carbon atoms is more preferably 1 to 10) and the compounds represented by tables 1Z3 to 6Z3 correspond to-NHCO-R102Z3And the like.
as-NHCON (R)102Z3)2Examples thereof include the groups listed above and the compounds shown in tables 1Z3 to 6Z3 which correspond to-NHCON (R)102Z3)2And the like.
as-NHCOOR102Z3Examples thereof include the groups listed above and the groups corresponding to-NHCOOR among the compounds shown in tables 1Z3 to 6Z3102Z3And the like.
as-OCON (R)102Z3)2Examples thereof include those corresponding to-OCON (R) in the above-mentioned groups and the compounds shown in tables 1Z3 to 6Z3102Z3)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M in M is a hydrogen atom; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102Z3、-COO-R102Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R102Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCON(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
R2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 3). As R2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, and benzo [9,10 ] ene]Phenanthrene, pyrene,
Figure BDA0003121580680002001
Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide and butachlor, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, etc.); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,
Figure BDA0003121580680002002
Nitrogen-containing fused heterocycles such as pyridine, phenanthroline, and phenazine, and partial reductants thereof; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3In the case of forming a ring, the ring may have a substituent. Examples of the substituent include1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3Z3And R4Z3When forming a ring, as R2Z3And R5Z3Independently of one another, hydrogen atoms, amino groups and hydroxyl groups are preferred.
R2Z3And R3Z3When a ring is formed, R is preferably4Z3And R5Z3Does not form a ring, more preferably R4Z3And R5Z3Is a hydrogen atom.
R4Z3And R5Z3When a ring is formed, R is preferably2Z3And R3Z3Does not form a ring, more preferably R2Z3And R3Z3Is a hydrogen atom.
In the present invention, R1Z3、R6Z3And R7Z3Preferably a hydrogen atom.
From the viewpoint of reducing the retardation value of a color filter made of the colored composition, R is preferably2Z3、R3Z3、R4Z3And R5Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, more preferably a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a halogen atom, -N (R)102Z3)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z3、-O-R102Z3、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Alternatively, R is preferred2Z3And R3Z3、R3Z3And R4Z3Or R4Z3And R5Z3Form a ring.
Compound IZ3 is preferably the following compound: r 2Z3、R3Z3、R4Z3And R5Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3At least one group of the compounds (hereinafter, this compound may be referred to as "compound IZ 3-B") is bonded to form a ring. When the compound IZ3 is the compound IZ3-B, the retardation value of the color filter produced from the colored composition becomes small.
When the above compound IZ3-B is defined by a chemical formula, it is as follows.
Figure BDA0003121580680002021
[ formula (IZ3-B) wherein R1Z3、R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3Each of which may be bonded to each other to form a ring.
Wherein R is21Z3、R31Z3、R41Z3And R5Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3At least one group of them is bonded to form a ring.
R101Z3The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
R102Z3Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents a hydrogen atom or an alkali metal atom.
R101Z3、R102Z3And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
In the formula (IZ3-B), with respect to R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Respectively, R in the formula (IZ3)2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3The same example.
In the formula (IZ3-B), with respect to preferred R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Respectively, R in the formula (IZ3)2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3The same preferred examples as those of (1).
In the formula (IZ3-B), (mode 1) R1Z3、R61Z3And R71Z3Is preferably a hydrogen atom. In addition, (mode 2) R21Z3、R31Z3、R41Z3And R51Z3It is also preferred that at least one of them is nitro or tert-butyl. Either or both of the modes 1 and 2 may be employed.
From the viewpoint of reducing the retardation value of a color filter made of the colored composition, R is preferably2Z3、R3Z3、R4Z3And R5Z3At least one of which is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, or-N (R)102Z3)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z3、-O-R102Z3、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. It is especially preferred that R 3Z3Is nitro or tert-butyl, R2Z3、R4Z3And R5Z3Is a hydrogen atom; or, R2Z3、R3Z3And R5Z3Is a hydrogen atom, R4Z3Is nitro or tert-butyl.
Specific examples of the compound IZ3 include compounds IZ3-1 to IZ3-212 having a substituent shown in table 1Z3, table 2Z3, table 3Z3, table 4Z3, table 5Z3, and table 6Z3 in formula (IZ3-aa), and alkali metal salts thereof.
Ba1Z3Ba2Z3The partial structure represented by any one of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) is shown. Formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8),Formula (BBO10), formula (BBD1) and formula (BBJ2) are the same as B representing formula (IZ1-aa)a1Z1Ba2Z1The same structures as (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) described above. B isa1Z3And Ba2Z3Each represents a chemical bond, Ba1Z3B of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2)1When a chemical bond of (A) is present, Ba2Z3To be B2The chemical bond of (a); b isa1Z3B of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) 2When a chemical bond of (A) is present, Ba2Z3To be B1The chemical bond of (1). As Ba1Z3Ba2Z3Formula (BB1), formula (BB6), formula (BB8), formula (BB11), formula (BB14), formula (BB19), formula (BB37), formula (BB58), formula (BBJ2), formula (BBO8), and formula (BBO10) are preferable, and formula (BB1), formula (BB6), and formula (BB19) are more preferable.
Figure BDA0003121580680002041
Each symbol in table 1Z3, table 2Z3, table 3Z3, table 4Z3, table 5Z3, and table 6Z3 represents the following partial structure. In the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group, "Hex" represents a hexyl group, "Oct" represents an octyl group, "2 EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group, "CH" represents a cyclohexyl group,
"PH" represents phenyl, "BZ" represents benzyl, "NPR" represents propyl, "IPR" represents isopropyl, "IBu" represents isobutyl, and "EOE" represents-CH2CH2OCH2CH3"ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents-CO-CH3And "COE" represents-COO-CH2CH3And "OCM" represents-OCO-CH3And "OME" represents-O-CH3,“SOT"represents a tosyl group," SNH "represents-SO2NH-CH2CH(CH2CH3)((CH2)3CH3) "SN 2" represents-SO2N(CH3)((CH2)7CH3) "CNM" represents-CONHCH3And "CN 2" represents-CON (CH) 3)C6H5And "NPH" represents-NHC6H5And "NOT" represents-N ((CH)2)7CH3)2And "NCO" represents-NHCO ((CH)2)4CH3) "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO 2" represents a nitro group, and "SUA" represents-SO3H, "CBA" means-CO2H, "CHO" means-CHO, "OCH" means-OCOH, "OH" means-OH, "SFM" means-SO2NH2"CBM" represents-CONH2"NH 2" means-NH2"NCH" represents-NHCOH.
[ Table 1Z3]
TABLE 1Z3
Ba1Z3Ba2Z3 R1Z3 R6Z3 R7Z3
IZ3-1 BB1 H H H
IZ3-2 BB2 H H H
IZ3-3 BB3 H H H
IZ3-4 BB4 H H H
IZ3-5 BB5 H H H
IZ3-6 BB6 H H H
IZ3-7 BB7 H H H
IZ3-8 BB8 H H H
IZ3-9 BB9 H H H
IZ3-10 BB10 H H H
IZ3-11 BB11 H H H
IZ3-12 BB12 H H H
IZ3-13 BB13 H H H
IZ3-14 BB14 H H H
IZ3-15 BB15 H H H
IZ3-16 BB16 H H H
IZ3-17 BB17 H H H
IZ3-18 BB18 H H H
IZ3-19 BB19 H H H
IZ3-20 BB20 H H H
IZ3-21 BB21 H H H
IZ3-22 BB22 H H H
IZ3-23 BB23 H H H
IZ3-24 BB24 H H H
IZ3-25 BB25 H H H
IZ3-26 BB26 H H H
IZ3-27 BB27 H H H
IZ3-28 BB28 H H H
IZ3-29 BB29 H H H
IZ3-30 BB30 H H H
IZ3-31 BB31 H H H
IZ3-32 BB32 H H H
IZ3-33 BB33 H H H
IZ3-34 BB34 H H H
IZ3-35 BB35 H H H
IZ3-36 BB36 H H H
IZ3-37 BB37 H H H
IZ3-38 BB38 H H H
IZ3-39 BB39 H H H
IZ3-40 BB40 H H H
[ Table 2Z3]
TABLE 2Z3
Ba1Z3Ba2Z3 R1Z3 R6Z3 R7Z3
IZ3-41 BB41 H H H
IZ3-42 BB42 H H H
IZ3-43 BB43 H H H
IZ3-44 BB44 H H H
IZ3-45 BB45 H H H
IZ3-46 BB46 H H H
IZ3-47 BB47 H H H
IZ3-48 BB48 H H H
IZ3-49 BB49 H H H
IZ3-50 BB50 H H H
IZ3-51 BB51 H H H
IZ3-52 BB52 H H H
IZ3-53 BB53 H H H
IZ3-54 BB54 H H H
IZ3-55 BB55 H H H
IZ3-56 BB56 H H H
IZ3-57 BB57 H H H
IZ3-58 BB58 H H H
IZ3-59 BB59 H H H
IZ3-60 BB60 H H H
IZ3-61 BB1 H EOE EOE
IZ3-62 BB2 H ALL ALL
IZ3-63 BB3 H NH2 NH2
IZ3-64 BB4 H CBM CBM
IZ3-65 BB5 H COM COM
IZ3-66 BB6 H COE COE
IZ3-67 BB7 H CBA CBA
IZ3-68 BB8 H HYE HYE
IZ3-69 BB9 H Me Me
IZ3-70 BB10 H CH CH
IZ3-71 BB11 H BZ H
IZ3-72 BB12 Me Me Me
IZ3-73 BB13 Et CH CH
IZ3-74 BB14 H Et Et
IZ3-75 BB15 H Bu Bu
IZ3-76 BB16 H TBu TBu
IZ3-77 BB17 H Hex Hex
IZ3-78 BB18 H Oct Oct
IZ3-79 BB19 H Me Me
IZ3-80 BB20 H CH CH
[ Table 3Z3]
TABLE 3Z3
Ba1Z3Ba2Z3 R1Z3 R6Z3 R7Z3
IZ3-81 BB21 H BZ H
IZ3-82 BB22 Me Me Me
IZ3-83 BB23 Et CH CH
IZ3-84 BB24 H Et Et
IZ3-85 BB25 H Bu Bu
IZ3-86 BB26 H TBu TBu
IZ3-87 BB27 H Hex Hex
IZ3-88 BB28 H Oct Oct
IZ3-89 BB29 H 2EH 2EH
IZ3-90 BB30 H CHM CHM
IZ3-91 BB31 H PH PH
IZ3-92 BB32 H BZ BZ
IZ3-93 BB33 H NPR NPR
IZ3-94 BB34 H IPR IPR
IZ3-95 BB35 H IBu IBu
IZ3-96 BB36 H EOE EOE
IZ3-97 BB37 H ALL ALL
IZ3-98 BB38 H NH2 NH2
IZ3-99 BB39 H CBM CBM
IZ3-100 BB40 H COM COM
IZ3-101 BB41 H COE COE
IZ3-102 BB42 H CBA CBA
IZ3-103 BB43 H HYE HYE
IZ3-104 BB44 H Me Me
IZ3-105 BB45 H CH CH
IZ3-106 BB46 H BZ H
IZ3-107 BB47 Me Me Me
IZ3-108 BB48 Et CH CH
IZ3-109 BB49 H Et Et
IZ3-110 BB50 H Bu Bu
IZ3-111 BB51 H TBu TBu
IZ3-112 BB52 H Hex Hex
IZ3-113 BB53 H Oct Oct
IZ3-114 BB54 H 2EH 2EH
IZ3-115 BB55 H CHM CHM
IZ3-116 BB56 H PH PH
IZ3-117 BB57 H BZ BZ
IZ3-118 BB58 H NPR NPR
IZ3-119 BB59 H IPR IPR
IZ3-120 BB60 H IBu IBu
[ Table 4Z3]
TABLE 4Z3
Ba1Z3Ba2Z3 R1Z3 R6Z3 R7Z3
IZ3-121 BB1 H Me H
IZ3-122 BB2 H H COM
IZ3-123 BB3 H COE H
IZ3-124 BB4 H H Et
IZ3-125 BB5 H OCM H
IZ3-126 BB6 H H OME
IZ3-127 BB7 H Bu H
IZ3-128 BB8 H H SOT
IZ3-129 BB9 H SNH H
IZ3-130 BB10 H H TBu
IZ3-131 BB11 H SN2 H
IZ3-132 BB12 H H CNM
IZ3-133 BB13 H Hex H
IZ3-134 BB14 H H CN2
IZ3-135 BB15 H NPH H
IZ3-136 BB16 H H Oct
IZ3-137 BB17 H NOT H
IZ3-138 BB18 H H NCO
IZ3-139 BB19 H 2EH H
IZ3-140 BB20 H H F
IZ3-141 BB21 H Cl H
IZ3-142 BB22 H H CHM
IZ3-143 BB23 H Br H
IZ3-144 BB24 H H CN
IZ3-145 BB25 H CH H
IZ3-146 BB26 H H NO2
IZ3-147 BB27 H SUA H
IZ3-148 BB28 H H PH
IZ3-149 BB29 H CBA H
IZ3-150 BB30 H H CHO
IZ3-151 BB31 H BZ BZ
IZ3-152 BB32 H H OCH
IZ3-153 BB33 H NPR H
IZ3-154 BB34 H H OH
IZ3-155 BB35 H IPR H
IZ3-156 BB36 H H SFM
IZ3-157 BB37 H IBu H
IZ3-158 BB38 H H CBM
IZ3-159 BB39 H EOE H
IZ3-160 BB40 H H NH2
[ Table 5Z3]
TABLE 5Z3
Ba1Z3Ba2Z3 R1Z3 R6Z3 R7Z3
IZ3-161 BB41 H ALL H
IZ3-162 BB42 H H NCH
IZ3-163 BB43 H HYE H
IZ3-164 BB44 Me H H
IZ3-165 BB45 COM H H
IZ3-166 BB46 COE H H
IZ3-167 BB47 Et H H
IZ3-168 BB48 OCM H H
IZ3-169 BB49 OME H H
IZ3-170 BB50 Bu H H
IZ3-171 BB51 SOT H H
IZ3-172 BB52 SNH H H
IZ3-173 BB53 TBu H H
IZ3-174 BB54 SN2 H H
IZ3-175 BB55 CNM H H
IZ3-176 BB56 Hex H H
IZ3-177 BB57 CN2 H H
IZ3-178 BB58 NPH H H
IZ3-179 BB59 Oct H H
IZ3-180 BB60 NOT H H
IZ3-181 BB1 NCO H H
IZ3-182 BB2 2EH H H
IZ3-183 BB3 F H H
IZ3-184 BB4 Cl H H
IZ3-185 BB5 CHM H H
IZ3-186 BB6 Br H H
IZ3-187 BB7 CN H H
IZ3-188 BB8 CH H H
IZ3-189 BB9 NO2 H H
IZ3-190 BB10 SUA H H
IZ3-191 BB11 PH H H
IZ3-192 BB12 CBA H H
IZ3-193 BB13 CHO H H
IZ3-194 BB14 BZ H H
IZ3-195 BB15 OCH H H
IZ3-196 BB16 NPR H H
IZ3-197 BB17 OH H H
IZ3-198 BB18 IPR H H
IZ3-199 BB19 SFM H H
IZ3-200 BB20 IBu H H
[ Table 6Z3]
TABLE 6Z3
Ba1Z3Ba2Z3 R1Z3 R6Z3 R7Z3
IZ3-201 BB21 CBM H H
IZ3-202 BB22 EOE H H
IZ3-203 BB23 NH2 H H
IZ3-204 BB24 ALL H H
IZ3-205 BB25 NCH H H
IZ3-206 BB26 HYE H H
IZ3-207 BBI1 H H H
IZ3-208 BBD1 H H H
IZ3-209 BBK2 H H H
IZ3-210 BBK3 H H H
IZ3-211 BBK4 H H H
IZ3-212 BBK14 H H H
For example, the compound IZ3-1 is a compound represented by the formula (IZ 3-1).
Figure BDA0003121580680002111
The compound IZ3 is preferably a compound IZ3-1 to a compound IZ3-120 and a compound IZ3-207 to a compound IZ3-212, more preferably a compound IZ3-1 to a compound IZ3-120, further preferably a compound IZ3-1 to a compound IZ3-60, further more preferably a compound IZ3-1 to a compound IZ3-36, a compound IZ3-37 and a compound IZ3-58,
particularly preferred are the compounds IZ3-1 to IZ3-36, particularly more preferred are the compounds IZ3-1, IZ3-6, IZ3-8, IZ3-11, IZ3-14 and IZ3-19, and particularly preferred are the compounds IZ3-1, IZ3-6 and IZ 3-19.
Specific examples of the compound IZ3 include those shown in tables 1Z3 to 6Z31 to 3 hydrogen atoms contained in the compound are replaced by-SO3M or-CO2M is substituted. For example, compounds having 1 to 3 sulfo groups bonded to the compound IZ3-1 of Table 1Z3 are represented by the following structures. Wherein, in the formula, - (SO)3H) Represents a compound in which any hydrogen atom in compound IZ3-1 of Table 1Z3 is substituted.
Figure BDA0003121580680002121
In the present invention, it is preferable that 1 to 3-SO groups are bonded to the compound IZ3-1 to the compound IZ3-120 and the compound IZ3-207 to the compound IZ3-2123M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ3-1 to the compound IZ3-1203M or-CO2M, more preferably 1 to 3-SO groups are bonded to the compound IZ3-1 to the compound IZ3-603M or-CO2More preferably, the compound of M is one in which 1 to 3-SO groups are bonded to the compound IZ3-1 to the compound IZ3-36, the compound IZ3-37 or the compound IZ3-583M or-CO2M, particularly preferably 1 to 3-SO groups are bonded to the compound IZ3-1 to the compound IZ3-363M or-CO2M, particularly preferably 1 to 3-SO groups are bonded to the compound IZ3-1, the compound IZ3-6, the compound IZ3-8, the compound IZ3-11, the compound IZ3-14 and the compound IZ3-19 3M or-CO2M, particularly preferably 1 to 3-SO groups are bonded to the compound IZ3-1, the compound IZ3-6 or the compound IZ3-193M or-CO2M, or a salt thereof.
Figure BDA0003121580680002122
As the compound (IZ3), the following compounds are preferable:
in the formula (IZ3), R1Z3Is a hydrogen atom and may have a radical selected from the group consisting of-SO3M and-CO2The number of carbon atoms of the substituent in the group consisting of M is1 to 20 hydrocarbyl groups, -SO3M or-CO2M,
R2Z3~R5Z3Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z3)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z3、-O-R102Z3、-SO3M or-CO2M,
R6Z3And R7Z3Independently of one another, a hydrogen atom, may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,R102Z3Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 20 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
R1Z3is a hydrogen atom, and is a hydrogen atom,
R2Z3~R5Z3each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z3)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102Z3、-O-R102Z3、-SO3M or-CO2M,R6Z3And R7Z3Are the same group, are hydrogen atoms, or may have a structure selected from the group consisting of3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R102Z3Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
a compound in which M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
R1Z3is a hydrogen atom, R2Z3~R5Z3Each independently a hydrogen atom, a C1-10 hydrocarbon group, a halogenAtom, -N (R)102Z3)2Nitro, trifluoromethyl, -O-R102Z3、-SO3M or-CO2M,R6Z3And R7Z3The same group is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms,
R102Z3is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
m is a hydrogen atom or an alkali metal atom.
For compound IZ3, R1Z3In the case of a hydrogen atom, the compound represented by the formula (pt1Z3) (hereinafter, may be referred to as a phthalonitrile compound) may be produced by reacting a compound represented by the formula (pt2Z3) (hereinafter, may be referred to as an alkoxide compound), and then further reacting the compound represented by the formula (pt3Z3) and the compound represented by the formula (pt4Z3) in the presence of an acid. In addition, R 1Z3When not a hydrogen atom, the compound is further reacted with a compound represented by the formula (pt5Z3) to produce a compound IZ 3.
Figure BDA0003121580680002141
In [ formula (pt1Z3), formula (pt2Z3), formula (pt3Z3), formula (pt4Z3), formula (pt5Z3) and formula (IZ3), R1Z3~R7Z3The same meanings as described above are indicated. R14Z3Represents an alkyl group having 1 to 20 carbon atoms. M1Z3Represents an alkali metal atom. LG represents a halogen atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group.]
As R14Z3Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z3Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z3 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z3 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z3, and the compound pt4Z3 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; 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 acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound.
The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z3 used, relative to R1Z3The amount of the compound IZ31 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
When the compound pt5Z3 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1Z3The amount of the compound IZ31 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
The reaction of compound pt5Z3 can generally be carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1Z3The amount of the compound IZ 31 is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z3 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound IZ3 having no sulfo group or-SO3M2In the case of (3), the compound IZ3 can be reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to introduce a sulfo group or-SO3M22
M22Represents an alkali metal atom. As M22Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
With respect to SO in oleum3The amount of (b) is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and still more preferably 5 to 25 mol based on 31 mol of the compound IZ.
The amount of sulfuric acid used in the oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on 31 moles of the compound IZ.
The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on 31 moles of the compound IZ.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound IZ3 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is filtered to extract the compound IZ 3. Further, the residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After the completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
< Compound IZ4 >)
Compound IZ4 is a compound represented by formula (IZ 4).
Figure BDA0003121580680002171
[ in the formula (IZ4),RN1Z4and RN2Z4Independently of one another represent-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4And R7Z4Independently of one another, represents a hydrogen atom, -CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4Each of which may be bonded to each other to form a ring. R 101Z4The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z4Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents a hydrogen atom or an alkali metal atom.
R101Z4、R102Z4And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The number of carbon atoms of the hydrocarbon group is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, and particularly preferably 1 to 10. RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, further more preferably 1 to 8, and particularly preferably 1 to 5. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable, and a methyl group, an ethyl group, and a tert-butyl group are particularly preferable.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, and, Cycloalkyl groups such as 2,2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl are particularly preferable.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a mesityl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, and a 2, 6-bis (2-propyl) benzeneAn aromatic hydrocarbon group such as a phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 5,6,7, 8-tetrahydro-1-naphthyl group, a 5,6,7, 8-tetrahydro-2-naphthyl group, a fluorenyl group, a phenanthryl group, an anthracyl group, or a pyrenyl group; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4Examples of the group represented by the above-mentioned groups, which are a combination of the above-mentioned hydrocarbon groups (e.g., chain hydrocarbon groups and alicyclic hydrocarbon groups), include alkyl groups to which 1 or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl groups, cyclopropylethyl groups, cyclobutylmethyl groups, cyclobutylethyl groups, cyclopentylmethyl groups, cyclopentylethyl groups, cyclohexylmethyl groups, 2-methylcyclohexylmethyl groups, cyclohexylethyl groups, and adamantylmethyl groups.
The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group represented may have a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
Figure BDA0003121580680002211
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl; a formyl group; a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
Figure BDA0003121580680002212
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
Figure BDA0003121580680002221
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formula);
Figure BDA0003121580680002231
Figure BDA0003121580680002241
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, N-phenylmethylsulfamoyl, and the like, and groups represented by the following chemical formulae);
Figure BDA0003121580680002251
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
Figure BDA0003121580680002261
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is an alkali metal, preferably lithium, sodium, potassium); a nitro group; a cyano group;
a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
Figure BDA0003121580680002271
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
Figure BDA0003121580680002273
Figure BDA0003121580680002281
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
Figure BDA0003121580680002291
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, or a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3、-CO-S-CH2-CH2-CH2-CH3or a thiocarbonyl group, -CO-S-C, bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) 6H5A thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms;
a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
Figure BDA0003121580680002301
-NRCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
Figure BDA0003121580680002302
Figure BDA0003121580680002311
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorogen) A derivative of an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), wherein R's may be the same or different and may be bonded to each other to form a ring);
Figure BDA0003121580680002312
Figure BDA0003121580680002321
a group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
Figure BDA0003121580680002322
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR3(wherein R is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms) (for exampleA hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring); and so on.
Examples of the substituent having a valence of 2 include an oxo group, a thioxo 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. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (you)Sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom. ) (ii) a A nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent;
A hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine;
an oxo group.
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a hydroxyl group; fluorine atom, chlorine atom, bromine atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; fluorine A hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are substituted with atoms; a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group having 1 to 40 carbon atoms and having a substituent represented by the formula (I) includes a hydrocarbon group having 1 to 40 carbon atoms and having a substituent having a valence of 1 or 2, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, and a group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which are a combination of hydrocarbon groups,
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups having 1 to 20 carbon atoms having a substituent of group s1,
Particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 1 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4Hetero ofThe cyclic group may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include:
monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole;
a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine;
A fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine;
condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane;
bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane;
lactone heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone;
five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran;
fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole, chroman and isochroman;
fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include:
five-membered ring system saturated heterocycles such as dithiolane;
saturated heterocyclic rings of six-membered ring systems such as thiacyclohexane, 1, 3-dithiane, 2-methyl-1, 3-dithiane and the like;
a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran);
fused bicyclic heterocycles such as benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include:
monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone; a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole);
fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
Figure BDA0003121580680002371
The above heterocyclic group may be R1Z4~R5Z42 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1Z4~R5Z4The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
Figure BDA0003121580680002372
The bonding position of the heterocyclic ring is a portion where any hydrogen atom contained in each ring is removed.
RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The heterocyclic group represented may have a substituent. Examples of the substituent includeN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group may have the same substituent as the substituent. In the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom.
Preferred examples of the substituent includeN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The preferable examples of the substituents which the hydrocarbon group may have are the same.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The heterocyclic group having a substituent(s) represented by (a) may be a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably Preferred examples thereof include heterocyclic groups having a substituent of group s 2. The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4Of (a) is-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, -SO3M、-CO2M is explained.
as-CO-R102Z4Examples thereof include a formyl group; acetyl, propionyl, butyryl, 2-dimethylpropionyl, pentanoyl, hexanoyl, (2-ethyl) hexanoyl, heptanoyl, examples of the carbonyl group include a carbonyl group (in the case where the carbonyl group is an acyl group, the number of carbon atoms is 2 to 41) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyl group, a nonanoyl group, a decanoyl group, a undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group, and the compounds shown in tables 1Z4 to 8Z4 and 11Z4 to 16Z4 correspond to — CO — R. 102Z4The group (b) preferably includes a carbonyl group (in which the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bondedIn the case, the number of carbon atoms is more preferably 2 to 12) and the compounds shown in Table 1Z4 to Table 8Z4 and Table 11Z4 to Table 16Z4 correspond to-CO-R102Z4And the like.
as-COO-R101Z4Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl and heptyloxycarbonyl, an oxycarbonyl group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group, an eicosyloxycarbonyl group and the like, and the groups represented by the above chemical formulae, and the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 correspond to-COO-R. 102Z4Preferred examples of the group (b) include oxycarbonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 which correspond to-COO-R102Z4And the like.
as-OCO-R102Z4Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, examples of the carbonyl group include a carbonyl group (in the case where the carbonyl group is an acyloxy group, the carbon number is 2 to 41) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, and a benzoyloxy group, and tables 1Z4 to 8Z4 and 11Z4 to 16Z 4.Corresponding to-OCO-R in the compound102Z4Preferable examples of the group(s) include a carbonyloxy group (more preferably 2 to 12 carbon atoms when the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 corresponds to-OCO-R 102Z4And the like.
as-COCO-R102Z4Examples thereof include methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) hexyloxalyl, heptyloxalyl, octyloxalyl, nonyloxalyl, an oxalyl group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) is bonded, such as decyl oxalyl group, undecyloxalyl group, dodecyl oxalyl group, eicosyl oxalyl group, cyclopentyl oxalyl group, cyclohexyl oxalyl group, phenyl oxalyl group, p-tolyloxalyl group, and the group represented by the above chemical formula), and compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 correspond to — COCO — R.102Z4And the like.
as-O-R102Z4There may be mentioned a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 5-dimethylphenyloxy, 2, 6-dimethylphenyloxy, 3, 4-dimethylphenyloxy, 3, 5-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 3-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 4-di-yloxy, 2-di-methyl-1-phenylethoxy, 2, 4-di-methyl, and mixtures thereof, 2, 5-dicyanophenyloxy, 2, 6-dicyanophenyloxy, 3, 4-dicyanophenyloxy, 3, 5-dicyanophenyloxy, 4-methoxyphenyloxy An oxy group having a hydrocarbyl group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as a phenylphenoxy group, a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the above chemical formula, and a group corresponding to-O-R-4 and the compounds represented by tables 1Z4 to 8Z4 and 11Z4 to 16Z4102Z4Preferred examples of the group (b) include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, which correspond to-O-R102Z4And the like.
as-SO2-R101Z4Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl) hexylsulfonyl, heptylsulfonyl, octylsulfonyl, nonyl sulfonyl, decyl sulfonyl, undecyl sulfonyl, dodecyl sulfonyl, eicosyl sulfonyl, phenyl sulfonyl, p-tolyl sulfonyl, and the like, and sulfonyl groups in which a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like is bonded, such as the group represented by the above chemical formula, and-SO corresponds to the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z 4. 2-R102Z4Preferable examples of the group (b) include sulfonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds represented by tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, which correspond to-SO2-R102Z4And the like.
as-SO2N(R102Z4)2Examples thereof include:
a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoylA hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, an N-butylsulfamoyl group, an N-sec-butylsulfamoyl group, an N-tert-butylsulfamoyl group, an N-pentylsulfamoyl group, an N- (1-ethylpropyl) sulfamoyl group, an N-hexylsulfamoyl group, an N- (2-ethyl) hexylsulfamoyl group, an N-heptylsulfamoyl group, an N-octylsulfamoyl group, an N-nonylsulfamoyl group, an N-decylsulfamoyl group, an N-undecylsulfamoyl group, an N-dodecylsulfamoyl group, an N-eicosylsulfamoyl group, an N-phenylsulfamoyl group and the like, and a group represented by the above formula, A derivative of nitro group, hydroxy group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group), or the like), and compounds represented by tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, which correspond to-SO 2NH(R102Z4X) (wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above), etc.;
n, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylsulfamoyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diethylsulfamoyl, A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a carbon atom, or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a carbon atom), and the like, such as an N, N-diheptylsulfamoyl group, an N, N-dioctylsulfamoyl group, an N, N-dinonylsulfamoyl group, an N, N-decylmethylsulfamoyl group, an N, N-undecylmethylsulfamoyl group, an N, N-dodecylmethylsulfamoyl group, an N, N-eicosylmethylsulfamoyl group, an N, N-phenylmethanesulfonyl group, an N, and an N, N-diphenylsulfamoyl group, and the like, and a group represented by the above chemical formula Groups derived from 1 to 10 alkylsulfamoyl groups (preferably octylsulfamoyl groups) and compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 correspond to-SO2N(R102Z4X)2(wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above) and the like,
preferred examples thereof include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds represented by tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, which correspond to-SO2N(R102Z4)2And the like.
as-CON (R)102Z4)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-octylcarbamoyl and N-nonylcarbamoyl, N-decylcarbamoyl, N-undecylcarbamoyl, N-dodecylcarbamoyl, N-eicosylcarbamoyl, N-phenylcarbamoyl and the like, Carbamoyl groups substituted with a 1-40 (preferably 1-20) carbon hydrocarbon group or derivative thereof (e.g., a derivative derived from carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), 1-10 carbon alkylsulfamoyl group (preferably octylsulfamoyl group)) such as the group represented by the above formula, and compounds shown in tables 1Z 4-8Z 4 and tables 11Z 4-16Z 4 corresponding to-CONH (R) 102Z4X) (wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above), etc.;
n, N-dimethylcarbamoyl, N-ethylmethylcarbamoyl, N-diethylcarbamoyl, N-propylmethylcarbamoyl, N-dipropylcarbamoylN, N-isopropylmethylcarbamoyl, N-diisopropylcarbamoyl, N-tert-butylmethylcarbamoyl, N-diisobutylcarbamoyl, N-di-sec-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-butylmethylcarbamoyl, N-dibutylcarbamoyl, N-butyloctylcarbamoyl, N-dipentylcarbamoyl, N-bis (1-ethylpropyl) carbamoyl, N-dihexylcarbamoyl, N-bis (2-ethyl) hexylcarbamoyl, N-diheptylcarbamoyl, N-octylmethylcarbamoyl, N-dioctylcarbamoyl, N-butylmethylcarbamoyl, N-dibutylcarbamoyl, N-butylmethylcarbamoyl, N-dibutylcarbamoyl, N-butylmethylcarbamoyl, N-dibutylcarbamoyl, N-butylmethylcarbamoyl, N-dibutylcarbamoyl, N-butylmethylcarbamoyl, N-butylt-butylmethylcarbamoyl, N-butylt-butylmethylcarbamoyl, N-butylt-butylmethylcarbamoyl, N-butylt-butylmethylcarbamoyl, N-butylt-butylmethylcarbamoyl, N-butylt-butyl, N, N-dinonylcarbamoyl, N-decylmethylcarbamoyl, N-undecylmethylcarbamoyl, N-dodecylmethylcarbamoyl, N-eicosylmethyl-carbamoyl, N-phenylmethylcarbamoyl, N, n-diphenylcarbamoyl and carbamoyl groups such as those represented by the above chemical formula which are substituted with 2 hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group), and the like), and the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 correspond to-CON (R). 102Z4X)2(wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z4 to 8Z4 and 11Z4 to 16Z4 which corresponds to-CON (R)102Z4)2And the like.
as-N (R)102Z4)2There may be mentioned amino groups; n-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-sec-butylamino, N-tert-butylamino, N-pentylamino, N-hexylamino, N- (2-ethyl) hexylamino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino, N-isobutylamino, N-sec-butylamino, N-pentylamino, N-hexylamino, N- (2-ethyl) hexylamino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino, N-dodecylamino, N-2-d-y-d-y-d-y-d,An amino group such as an N-phenylamino group, which is substituted with a 1-C1-40 (preferably C1-20) hydrocarbon group or a derivative thereof (e.g., a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a C1-10 alkylsulfamoyl group (preferably octylsulfamoyl group), etc.), or a group represented by the above formula, or an equivalent of-NH (R) in the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 102Z4X) (wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above), etc.; n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-dipentylamino group, N-bis (1-ethylpropyl) amino group, N-dihexylamino group, N-bis (2-ethyl) hexylamino group, N-diheptylamino group, N-dioctylamino group, N, an amino group substituted with a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc., such as an N-dinonylamino group, an N, N-decylmethylamino group, an N, N-undecylmethylamino group, an N, N-dodecylmethylamino group, an N, N-eicosylmethylamino group, an N, N-phenylmethylamino group, an N, N-diphenylamino group, etc., and a group represented by the above chemical formula, and an amino group corresponding to-N (R) in the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, respectively 102Z4X)2(wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above) and the like,
preferred examples thereof include amino groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds shown in tables 1Z4 to 8Z4 and 11Z4 to 16Z4 which correspond to-N (R)102Z4)2And the like.
as-NHCO-R102Z4Can do toTo produce formylamino; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecanoylamino, dodecanoylamino, heneicosanoylamino, benzoylamino and the like, carbonylamino (for example, in the case where the carbonylamino is an acylamino group, the carbon number is 1 to 40), carbonylamino to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as a group represented by the above-mentioned chemical formula) and carbonylamino (in the case where the carbonylamino group is an acylamino group, the carbon number is 1 to 40) corresponding to-NHCO- R 102Z4And the like,
preferred examples thereof include carbonylamino groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded (in the case where the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10), and compounds represented by tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, which correspond to-NHCO-R102Z4And the like.
as-NHCON (R)102Z4)2Examples thereof include the groups listed above and the compounds shown in tables 1Z4 to 8Z4 and 11Z4 to 16Z4 which correspond to-NHCON (R)102Z4)2A group of (a); and so on.
as-NHCOOR102Z4Examples thereof include those corresponding to-NHCOOR among the above-mentioned groups and the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4102Z4And the like.
as-OCON (R)102Z4)2Examples thereof include those corresponding to-OCON (R) among the above-mentioned groups and the compounds shown in tables 1Z4 to 8Z4 and 11Z4 to 16Z4102Z4)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M of M is hydrogen atomA seed; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102Z4、-COO-R102Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R102Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCON(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 4). As R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, and benzo [9,10 ] ene]Phenanthrene, pyrene,
Figure BDA0003121580680002451
Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide and butachlor, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, etc.); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,
Figure BDA0003121580680002452
Pyridine, phenanthroline and thiopheneNitrogen-containing fused heterocycles such as oxazines and partial reductants thereof; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4In the case of forming a ring, the ring may have a substituent. Examples of the substituent include N1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent includeN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3Z4And R4Z4When forming a ring, as R2Z4And R5Z4Independently of one another, hydrogen atoms, amino groups and hydroxyl groups are preferred.
R2Z4And R3Z4When a ring is formed, R is preferably4Z4And R5Z4Does not form a ring, more preferably R4Z4And R5Z4Is a hydrogen atom.
In addition, R4Z4And R5Z4When a ring is formed, R is preferably2Z4And R3Z4Does not form a ring, more preferably R2Z4And R3Z4Is a hydrogen atom.
In the present invention, R1Z4、R6Z4And R7Z4Preferably a hydrogen atom.
In the present invention, RN1Z4And RN2Z4Independently of one another, are preferably-CO-R102Z4、-COO-R101Z4、-CON(R102Z4)2、-N(R102Z4)2、-CO2M or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, more preferably a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, still more preferablyThe hydrocarbon group having 1 to 20 carbon atoms which may have a substituent is selected, the hydrocarbon group having 1 to 15 carbon atoms which may have a substituent is particularly preferable, the hydrocarbon group having 1 to 10 carbon atoms which may have a substituent is particularly preferable, the hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or the hydrocarbon group having 1 to 5 carbon atoms which may have a substituent is particularly preferable, the methyl group, the ethyl group or the phenyl group is further particularly preferable, and the methyl group or the ethyl group is most preferable. In addition, R N1Z4And RN2Z4The groups may be the same or different, but preferably the same.
From the viewpoint of reducing the retardation value of a color filter made of the colored composition, R is preferably2Z4、R3Z4、R4Z4And R5Z4At least one of which is-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent,
more preferably a C1-40 hydrocarbon group which may have a substituent, a halogen atom, or-N (R)102Z4)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z4、-O-R102Z4、-SO3M or-CO2M,
More preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Alternatively, R is preferred2Z4And R3Z4、R3Z4And R4Z4Or R4Z4And R5Z4Form a ring.
From coloringFrom the viewpoint of reducing the retardation value of the color filter produced from the composition, R is preferably2Z4、R3Z4、R4Z4And R5Z4At least one of which is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, or-N (R)102Z4)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102Z4、-O-R102Z4、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. It is especially preferred that R3Z4Is nitro or tert-butyl, R2Z4、R4Z4And R5Z4Is a hydrogen atom; or, R2Z4、R3Z4And R5Z4Is a hydrogen atom, R4Z4Is nitro or tert-butyl.
Specific examples of the compound IZ4 include compounds IZ4-1 to IZ4-769 having a substituent shown in table 1Z4, table 2Z4, table 3Z4, table 4Z4, table 5Z4, table 6Z4, table 7Z4, table 8Z4, and table 11Z4 to table 16Z4 in formula (IZ4-aa), and alkali metal salts thereof.
Ba1Z4Ba2Z4The partial structure represented by any one of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) is shown. The formulae (BB1) to (BB60), (BBK2), (BBK3), (BBK4), (BBK14), (BBI1), (BBO8), (BBO10), (BBD1) and (BBJ2) are the same as B representing formula (IZ1-aa)a1Z1Ba2Z1The same structures as (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) described above. B isa1Z4And Ba2Z4Each represents a chemical bond, Ba1Z4B of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) 1When a chemical bond of (A) is present, Ba2Z4To be B2The chemical bond of (a); b isa1Z4Are represented by the formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK 14)) B of the formulae (BBI1), (BBO8), (BBO10), (BBD1) and (BBJ2)2When a chemical bond of (A) is present, Ba2Z4To be B1The chemical bond of (1).
As Ba1Z4Ba2Z4Formula (BB1), formula (BB6), formula (BB8), formula (BB11), formula (BB14), formula (BB19), formula (BB37), formula (BB58), formula (BBJ2), formula (BBO8), and formula (BBO10) are preferable, and formula (BB1), formula (BB6), and formula (BB19) are more preferable.
Figure BDA0003121580680002481
Each symbol in table 1Z4, table 2Z4, table 3Z4, table 4Z4, table 5Z4, table 6Z4, table 7Z4, table 8Z4, and tables 11Z4 to 16Z4 represents the following partial structure. In the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group,
"Hex" represents a hexyl group, "Oct" represents an octyl group, "2 EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group,
"CH" represents cyclohexyl, "PH" represents phenyl, "BZ" represents benzyl, "NPR" represents propyl,
"IPR" represents isopropyl, "IBu" represents isobutyl, and "EOE" represents-CH2CH2OCH2CH3"ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents-CO-CH 3And "COE" represents-COO-CH2CH3And "OCM" represents-OCO-CH3And "OME" represents-O-CH3"SOT" represents a tosyl group, and "SNH" represents-SO2NH-CH2CH(CH2CH3)((CH2)3CH3) "SN 2" represents-SO2N(CH3)((CH2)7CH3) "CNM" represents-CONHCH3And "CN 2" represents-CON (CH)3)C6H5And "NPH" represents-NHC6H5And "NOT" represents-N ((CH)2)7CH3)2,“NCO "represents-NHCO ((CH)2)4CH3) "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO 2" represents a nitro group, and "SUA" represents-SO3H, "CBA" means-CO2H, "CHO" means-CHO, "OCH" means-OCOH, "OH" means-OH, "SFM" means-SO2NH2"CBM" represents-CONH2"NH 2" means-NH2"NCH" represents-nhcooh, and represents a chemical bond.
In the table, a part of the structure shown in the following formula is represented by a symbol denoted by the structure.
Figure BDA0003121580680002491
Figure BDA0003121580680002501
Figure BDA0003121580680002511
[ Table 1Z4]
TABLE 1Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-1 Me Me BB1 H H H
IZ4-2 Et Et BB1 H H H
IZ4-3 PH PH BB1 H H H
IZ4-4 Bu Me BB1 H H H
IZ4-5 TBu Et BB1 H H H
IZ4-6 Hex NPR BB1 H H H
IZ4-7 Oct IPR BB1 H H H
IZ4-8 2EH HYE BB1 H H H
IZ4-9 CHM ALL BB1 H H H
IZ4-10 CH COM BB1 H H H
IZ4-11 BZ Me BB1 H H H
IZ4-12 NPR Et BB1 H H H
IZ4-13 IPR NPR BB1 H H H
IZ4-14 IBu IPR BB1 H H H
IZ4-15 EOE HYE BB1 H H H
IZ4-16 ALL ALL BB1 H H H
IZ4-17 NH2 COM BB1 H H H
IZ4-18 CBM Me BB1 H H H
IZ4-19 COM Et BB1 H H H
IZ4-20 COE NPR BB1 H H H
IZ4-21 CBA IPR BB1 H H H
IZ4-22 HYE HYE BB1 H H H
IZ4-23 Bu Bu BB1 H H H
IZ4-24 TBu TBu BB1 H H H
IZ4-25 Hex Hex BB1 H H H
IZ4-26 Oct Oct BB1 H H H
IZ4-27 2EH 2EH BB1 H H H
IZ4-28 CHM CHM BB1 H H H
IZ4-29 CH CH BB1 H H H
IZ4-30 BZ BZ BB1 H H H
IZ4-31 NPR NPR BB1 H H H
IZ4-32 IPR IPR BB1 H H H
IZ4-33 IBu IBu BB1 H H H
IZ4-34 EOE EOE BB1 H H H
IZ4-35 NH2 NH2 BB1 H H H
IZ4-36 CBM CBM BB1 H H H
IZ4-37 COM COM BB1 H H H
IZ4-38 COE COE BB1 H H H
IZ4-39 CBA CBA BB1 H H H
IZ4-40 Me Me BB6 H H H
[ Table 2Z4]
TABLE 2Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-41 Et Et BB6 H H H
IZ4-42 PH PH BB6 H H H
IZ4-43 Bu Me BB6 H H H
IZ4-44 TBu Et BB6 H H H
IZ4-45 Hex NPR BB6 H H H
IZ4-46 Oct IPR BB6 H H H
IZ4-47 2EH HYE BB6 H H H
IZ4-48 CHM ALL BB6 H H H
IZ4-49 CH COM BB6 H H H
IZ4-50 BZ Me BB6 H H H
IZ4-51 NPR Et BB6 H H H
IZ4-52 IPR NPR BB6 H H H
IZ4-53 IBu IPR BB6 H H H
IZ4-54 EOE HYE BB6 H H H
IZ4-55 ALL ALL BB6 H H H
IZ4-56 NH2 COM BB6 H H H
IZ4-57 CBM Me BB6 H H H
IZ4-58 COM Et BB6 H H H
IZ4-59 COE NPR BB6 H H H
IZ4-60 CBA IPR BB6 H H H
IZ4-61 HYE HYE BB6 H H H
IZ4-62 Bu Bu BB6 H H H
IZ4-63 TBu TBu BB6 H H H
IZ4-64 Hex Hex BB6 H H H
IZ4-65 Oct Oct BB6 H H H
IZ4-66 2EH 2EH BB6 H H H
IZ4-67 CHM CHM BB6 H H H
IZ4-68 CH CH BB6 H H H
IZ4-69 BZ BZ BB6 H H H
IZ4-70 NPR NPR BB6 H H H
IZ4-71 IPR IPR BB6 H H H
IZ4-72 IBu IBu BB6 H H H
IZ4-73 EOE EOE BB6 H H H
IZ4-74 NH2 NH2 BB6 H H H
IZ4-75 CBM CBM BB6 H H H
IZ4-76 COM COM BB6 H H H
IZ4-77 COE COE BB6 H H H
IZ4-78 CBA CBA BB6 H H H
IZ4-79 Me Me BB19 H H H
IZ4-80 Et Et BB19 H H H
[ Table 3Z4]
TABLE 3Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-81 PH PH BB19 H H H
IZ4-82 Bu Me BB19 H H H
IZ4-83 TBu Et BB19 H H H
IZ4-84 Hex NPR BB19 H H H
IZ4-85 Oct IPR BB19 H H H
IZ4-86 2EH HYE BB19 H H H
IZ4-87 CHM ALL BB19 H H H
IZ4-88 CH COM BB19 H H H
IZ4-89 BZ Me BB19 H H H
IZ4-90 NPR Et BB19 H H H
IZ4-91 IPR NPR BB19 H H H
IZ4-92 IBu IPR BB19 H H H
IZ4-93 EOE HYE BB19 H H H
IZ4-94 ALL ALL BB19 H H H
IZ4-95 NH2 COM BB19 H H H
IZ4-96 CBM Me BB19 H H H
IZ4-97 COM Et BB19 H H H
IZ4-98 COE NPR BB19 H H H
IZ4-99 CBA IPR BB19 H H H
IZ4-100 HYE HYE BB19 H H H
IZ4-101 Bu Bu BB19 H H H
IZ4-102 TBu TBu BB19 H H H
IZ4-103 Hex Hex BB19 H H H
IZ4-104 Oct Oct BB19 H H H
IZ4-105 2EH 2EH BB19 H H H
IZ4-106 CHM CHM BB19 H H H
IZ4-107 CH CH BB19 H H H
IZ4-108 BZ BZ BB19 H H H
IZ4-109 NPR NPR BB19 H H H
IZ4-110 IPR IPR BB19 H H H
IZ4-111 IBu IBu BB19 H H H
IZ4-112 EOE EOE BB19 H H H
IZ4-113 NH2 NH2 BB19 H H H
IZ4-114 CBM CBM BB19 H H H
IZ4-115 COM COM BB19 H H H
IZ4-116 COE COE BB19 H H H
IZ4-117 CBA CBA BB19 H H H
IZ4-118 Me Me BB2 H H H
IZ4-119 Et Et BB3 H H H
IZ4-120 PH PH BB4 H H H
[ Table 4Z4]
TABLE 4Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-121 Bu Me BB5 H H H
IZ4-122 TBu Et BB7 H H H
IZ4-123 Hex NPR BB8 H H H
IZ4-124 Oct IPR BB9 H H H
IZ4-125 2EH HYE BB10 H H H
IZ4-126 CHM ALL BB11 H H H
IZ4-127 CH COM BB12 H H H
IZ4-128 BZ Me BB13 H H H
IZ4-129 NPR Et BB14 H H H
IZ4-130 IPR NPR BB15 H H H
IZ4-131 IBu IPR BB16 H H H
IZ4-132 EOE HYE BB17 H H H
IZ4-133 ALL ALL BB18 H H H
IZ4-134 NH2 COM BB20 H H H
IZ4-135 CBM Me BB21 H H H
IZ4-136 COM Et BB22 H H H
IZ4-137 COE NPR BB23 H H H
IZ4-138 CBA IPR BB24 H H H
IZ4-139 HYE HYE BB25 H H H
IZ4-140 Bu Bu BB26 H H H
IZ4-141 TBu TBu BB27 H H H
IZ4-142 Hex Hex BB28 H H H
IZ4-143 Oct Oct BB29 H H H
IZ4-144 2EH 2EH BB30 H H H
IZ4-145 CHM CHM BB31 H H H
IZ4-146 CH CH BB32 H H H
IZ4-147 BZ BZ BB33 H H H
IZ4-148 NPR NPR BB34 H H H
IZ4-149 IPR IPR BB35 H H H
IZ4-150 IBu IBu BB36 H H H
IZ4-151 EOE EOE BB37 H H H
IZ4-152 NH2 NH2 BB38 H H H
IZ4-153 CBM CBM BB39 H H H
IZ4-154 COM COM BB40 H H H
IZ4-155 COE COE BB41 H H H
IZ4-156 CBA CBA BB42 H H H
IZ4-157 Me Me BB43 H H H
IZ4-158 Et Et BB44 H H H
IZ4-159 PH PH BB45 H H H
IZ4-160 Bu Me BB46 H H H
[ Table 5Z4]
TABLE 5Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-161 TBu Et BB47 H H H
IZ4-162 Hex NPR BB48 H H H
IZ4-163 Oct IPR BB49 H H H
IZ4-164 2EH HYE BB50 H H H
IZ4-165 CHM ALL BB51 H H H
IZ4-166 CH COM BB52 H H H
IZ4-167 BZ Me BB53 H H H
IZ4-168 NPR Et BB54 H H H
IZ4-169 IPR NPR BB55 H H H
IZ4-170 IBu IPR BB56 H H H
IZ4-171 EOE HYE BB57 H H H
IZ4-172 ALL ALL BB58 H H H
IZ4-173 NH2 COM BB59 H H H
IZ4-174 CBM Me BB60 H H H
IZ4-175 Bu Me BB1 H Et Et
IZ4-176 TBu Et BB2 H PH PH
IZ4-177 Hex NPR BB3 H NPR NPR
IZ4-178 Oct IPR BB4 H IPR IPR
IZ4-179 2EH HYE BB5 H ALL ALL
IZ4-180 CHM ALL BB6 H Me Me
IZ4-181 CH COM BB7 H CH CH
IZ4-182 BZ Me BB8 H BZ H
IZ4-183 NPR Et BB9 Me Me Me
IZ4-184 IPR NPR BB10 Et CH CH
IZ4-185 IBu IPR BB11 H Et Et
IZ4-186 EOE HYE BB12 H Bu Bu
IZ4-187 ALL ALL BB13 H TBu TBu
IZ4-188 NH2 COM BB14 H Hex Hex
IZ4-189 CBM Me BB15 H Oct Oct
IZ4-190 COM Et BB16 H 2EH 2EH
IZ4-191 COE NPR BB17 H CHM CHM
IZ4-192 CBA IPR BB18 H PH PH
IZ4-193 Me Me BB19 H BZ BZ
IZ4-194 Et Et BB20 H NPR NPR
IZ4-195 PH PH BB21 H IPR IPR
IZ4-196 Bu Me BB22 H IBu IBu
IZ4-197 TBu Et BB23 H EOE EOE
IZ4-198 Hex NPR BB24 H ALL ALL
IZ4-199 Oct IPR BB25 H NH2 NH2
IZ4-200 2EH HYE BB26 H CBM CBM
[ Table 6Z4]
TABLE 6Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-201 CHM ALL BB27 H COM COM
IZ4-202 CH COM BB28 H COE COE
IZ4-203 BZ Me BB29 H CBA CBA
IZ4-204 NPR Et BB30 H HYE HYE
IZ4-205 IPR NPR BB31 H Me Me
IZ4-206 IBu IPR BB32 H CH CH
IZ4-207 EOE HYE BB33 H BZ H
IZ4-208 ALL ALL BB34 Me Me Me
IZ4-209 NH2 COM BB35 Et CH CH
IZ4-210 CBM Me BB36 H Et Et
IZ4-211 COM Et BB37 H Bu Bu
IZ4-212 COE NPR BB38 H TBu TBu
IZ4-213 CBA IPR BB39 H Hex Hex
IZ4-214 HYE HYE BB40 H Oct Oct
IZ4-215 Bu Bu BB41 H 2EH 2EH
IZ4-216 TBu TBu BB42 H CHM CHM
IZ4-217 Hex Hex BB43 H PH PH
IZ4-218 Oct Oct BB44 H BZ BZ
IZ4-219 2EH 2EH BB45 H NPR NPR
IZ4-220 CHM CHM BB46 H IPR IPR
IZ4-221 CH CH BB47 H IBu IBu
IZ4-222 BZ BZ BB48 H EOE EOE
IZ4-223 NPR NPR BB49 H ALL ALL
IZ4-224 IPR IPR BB50 H NH2 NH2
IZ4-225 IBu IBu BB51 H CBM CBM
IZ4-226 EOE EOE BB52 H COM COM
IZ4-227 NH2 NH2 BB53 H COE COE
IZ4-228 CBM CBM BB54 H CBA CBA
IZ4-229 COM COM BB55 H HYE HYE
IZ4-230 COE COE BB56 H Me Me
IZ4-231 CBA CBA BB57 H CH CH
IZ4-232 Me Me BB58 H BZ H
IZ4-233 Et Et BB59 Me Me Me
IZ4-234 PH PH BB60 Et CH CH
IZ4-235 Bu Me BB1 H H NO2
IZ4-236 TBu Et BB2 H SUA H
IZ4-237 Hex NPR BB3 H H PH
IZ4-238 Oct IPR BB4 H CBA H
IZ4-239 2EH HYE BB5 H H CHO
IZ4-240 Me Me BB6 H BZ BZ
[ Table 7Z4]
TABLE 7Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-241 Et Et BB7 H H OCH
IZ4-242 PH PH BB8 H NPR H
IZ4-243 Bu Me BB9 H H OH
IZ4-244 TBu Et BB10 H IPR H
IZ4-245 Hex NPR BB11 H H SFM
IZ4-246 Oct IPR BB12 H IBu H
IZ4-247 2EH HYE BB13 H H CBM
IZ4-248 CHM ALL BB14 H EOE H
IZ4-249 CH COM BB15 H H NH2
IZ4-250 BZ Me BB16 H ALL H
IZ4-251 NPR Et BB17 H H NCH
IZ4-252 IPR NPR BB18 H HYE H
IZ4-253 IBu IPR BB19 Me H H
IZ4-254 EOE HYE BB20 COM H H
IZ4-255 ALL ALL BB21 COE H H
IZ4-256 NH2 COM BB22 Et H H
IZ4-257 CBM Me BB23 OCM H H
IZ4-258 COM Et BB24 OME H H
IZ4-259 COE NPR BB25 Bu H H
IZ4-260 CBA IPR BB26 SOT H H
IZ4-261 HYE HYE BB27 SNH H H
IZ4-262 Bu Bu BB28 TBu H H
IZ4-263 TBu TBu BB29 SN2 H H
IZ4-264 Hex Hex BB30 CNM H H
IZ4-265 Oct Oct BB31 Hex H H
IZ4-266 2EH 2EH BB32 CN2 H H
IZ4-267 CHM CHM BB33 NPH H H
IZ4-268 CH CH BB34 Oct H H
IZ4-269 BZ BZ BB35 NOT H H
IZ4-270 NPR NPR BB36 NCO H H
IZ4-271 IPR IPR BB37 H Me H
IZ4-272 IBu IBu BB38 H H COM
IZ4-273 EOE EOE BB39 H COE H
IZ4-274 NH2 NH2 BB40 H H Et
IZ4-275 CBM CBM BB41 H OCM H
IZ4-276 COM COM BB42 H H OME
IZ4-277 COE COE BB43 H Bu H
IZ4-278 CBA CBA BB44 H H SOT
IZ4-279 Me Me BB45 H SNH H
IZ4-280 Et Et BB46 H H TBu
[ Table 8Z4]
TABLE 8Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-281 PH PH BB47 H SN2 H
IZ4-282 Bu Me BB48 H H CNM
IZ4-283 TBu Et BB49 H Hex H
IZ4-284 Hex NPR BB50 H H CN2
IZ4-285 Oct IPR BB51 H NPH H
IZ4-286 2EH HYE BB52 H H Oct
IZ4-287 CHM ALL BB53 H NOT H
IZ4-288 CH COM BB54 H H NCO
IZ4-289 BZ Me BB55 H 2EH H
IZ4-290 NPR Et BB56 H H F
IZ4-291 IPR NPR BB57 H Cl H
IZ4-292 IBu IPR BB58 H H CHM
IZ4-293 EOE HYE BB59 H Br H
IZ4-294 ALL ALL BB60 H H CN
IZ4-295 NH2 COM BB1 H CH H
IZ4-296 CBM Me BB2 2EH H H
IZ4-297 COM Et BB3 F H H
IZ4-298 COE NPR BB4 Cl H H
IZ4-299 CBA IPR BB5 CHM H H
IZ4-300 HYE HYE BB6 Br H H
IZ4-301 Bu Bu BB7 CN H H
IZ4-302 TBu TBu BB8 CH H H
IZ4-303 Hex Hex BB9 NO2 H H
IZ4-304 Oct Oct BB10 SUA H H
IZ4-305 2EH 2EH BB11 PH H H
IZ4-306 CHM CHM BB12 CBA H H
IZ4-307 CH CH BB13 CHO H H
IZ4-308 BZ BZ BB14 BZ H H
IZ4-309 NPR NPR BB15 OCH H H
IZ4-310 IPR IPR BB16 NPR H H
IZ4-311 IBu IBu BB17 OH H H
IZ4-312 EOE EOE BB18 IPR H H
IZ4-313 NH2 NH2 BB19 SFM H H
IZ4-314 CBM CBM BB20 IBu H H
IZ4-315 COM COM BB21 CBM H H
IZ4-316 COE COE BB22 EOE H H
IZ4-317 CBA CBA BB23 NH2 H H
IZ4-318 Me Me BB24 ALL H H
IZ4-319 Et Et BB25 NCH H H
IZ4-320 PH PH BB26 HYE H H
IZ4-321 Me Me BB8 H H H
[ Table 11Z4]
TABLE 11Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4 RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-322 NA1 NA1 BB1 H H H IZ4-362 CH Me BB6 H H H
IZ4-323 HHk8 HHk8 BB1 H H H IZ4-363 EOE Me BB6 H H H
IZ4-324 NA2 NA2 BB1 H H H IZ4-364 ALL Me BB6 H H H
IZ4-325 HHk7 HHk7 BB1 H H H IZ4-365 CBA Me BB6 H H H
IZ4-326 HH37 HH37 BB1 H H H IZ4-366 HYE Me BB6 H H H
IZ4-327 HHk6 HHk6 BB1 H H H IZ4-367 NA1 Me BB6 H H H
IZ4-328 NA3 NA3 BB1 H H H IZ4-368 HHk8 Me BB6 H H H
IZ4-329 HHJ2 HHJ2 BB1 H H H IZ4-369 NA2 Me BB6 H H H
IZ4-330 HHk11 HHk11 BB1 H H H IZ4-370 HHk7 Me BB6 H H H
IZ4-331 Et Me BB1 H H H IZ4-371 HH37 Me BB6 H H H
IZ4-332 PH Me BB1 H H H IZ4-372 HHk6 Me BB6 H H H
IZ4-333 Oct Me BB1 H H H IZ4-373 NA3 Me BB6 H H H
IZ4-334 CHM Me BB1 H H H IZ4-374 HHJ2 Me BB6 H H H
IZ4-335 CH Me BB1 H H H IZ4-375 HHk11 Me BB6 H H H
IZ4-336 EOE Me BB1 H H H IZ4-376 Et Et BB8 H H H
IZ4-337 ALL Me BB1 H H H IZ4-377 PH PH BB8 H H H
IZ4-338 CBA Me BB1 H H H IZ4-378 Oct Oct BB8 H H H
IZ4-339 HYE Me BB1 H H H IZ4-379 CHM CHM BB8 H H H
IZ4-340 NA1 Me BB1 H H H IZ4-380 CH CH BB8 H H H
IZ4-341 HHk8 Me BB1 H H H IZ4-381 BZ BZ BB8 H H H
IZ4-342 NA2 Me BB1 H H H IZ4-382 EOE EOE BB8 H H H
IZ4-343 HHk7 Me BB1 H H H IZ4-383 ALL ALL BB8 H H H
IZ4-344 HH37 Me BB1 H H H IZ4-384 CBA CBA BB8 H H H
IZ4-345 HHk6 Me BB1 H H H IZ4-385 HYE HYE BB8 H H H
IZ4-346 NA3 Me BB1 H H H IZ4-386 NA1 NA1 BB8 H H H
IZ4-347 HHJ2 Me BB1 H H H IZ4-387 HHk8 HHk8 BB8 H H H
IZ4-348 HHk11 Me BB1 H H H IZ4-388 NA2 NA2 BB8 H H H
IZ4-349 NA1 NA1 BB6 H H H IZ4-389 HHk7 HHk7 BB8 H H H
IZ4-350 HHk8 HHk8 BB6 H H H IZ4-390 HH37 HH37 BB8 H H H
IZ4-351 NA2 NA2 BB6 H H H IZ4-391 HHk6 HHk6 BB8 H H H
IZ4-352 HHk7 HHk7 BB6 H H H IZ4-392 NA3 NA3 BB8 H H H
IZ4-353 HH37 HH37 BB6 H H H IZ4-393 HHJ2 HHJ2 BB8 H H H
IZ4-354 HHk6 HHk6 BB6 H H H IZ4-394 HHk11 HHk11 BB8 H H H
IZ4-355 NA3 NA3 BB6 H H H IZ4-395 Et Me BB8 H H H
IZ4-356 HHJ2 HHJ2 BB6 H H H IZ4-396 PH Me BB8 H H H
IZ4-357 HHk11 HHk11 BB6 H H H IZ4-397 Oct Me BB8 H H H
IZ4-358 Et Me BB6 H H H IZ4-398 CHM Me BB8 H H H
IZ4-359 PH Me BB6 H H H IZ4-399 CH Me BB8 H H H
IZ4-360 Oct Me BB6 H H H IZ4-400 BZ Me BB8 H H H
IZ4-361 CHM Me BB6 H H H IZ4-401 EOE Me BB8 H H H
[ Table 12Z4]
TABLE 12Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4 RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-402 ALL Me BB8 H H H IZ4-442 CBA Me BB11 H H H
IZ4-403 CBA Me BB8 H H H IZ4-443 HYE Me BB11 H H H
IZ4-404 HYE Me BB8 H H H IZ4-444 NA1 Me BB11 H H H
IZ4-405 NA1 Me BB8 H H H IZ4-445 HHk8 Me BB11 H H H
IZ4-406 HHk8 Me BB8 H H H IZ4-446 NA2 Me BB11 H H H
IZ4-407 NA2 Me BB8 H H H IZ4-447 HHk7 Me BB11 H H H
IZ4-408 HHk7 Me BB8 H H H IZ4-448 HH37 Me BB11 H H H
IZ4-409 HH37 Me BB8 H H H IZ4-449 HHk6 Me BB11 H H H
IZ4-410 HHk6 Me BB8 H H H IZ4-450 NA3 Me BB11 H H H
IZ4-411 NA3 Me BB8 H H H IZ4-451 HHJ2 Me BB11 H H H
IZ4-412 HHJ2 Me BB8 H H H IZ4-452 HHk11 Me BB11 H H H
IZ4-413 HHk11 Me BB8 H H H IZ4-453 Me Me BB14 H H H
IZ4-414 Me Me BB11 H H H IZ4-454 Et Et BB14 H H H
IZ4-415 Et Et BB11 H H H IZ4-455 PH PH BB14 H H H
IZ4-416 PH PH BB11 H H H IZ4-456 Oct Oct BB14 H H H
IZ4-417 Oct Oct BB11 H H H IZ4-457 CHM CHM BB14 H H H
IZ4-418 CHM CHM BB11 H H H IZ4-458 CH CH BB14 H H H
IZ4-419 CH CH BB11 H H H IZ4-459 BZ BZ BB14 H H H
IZ4-420 BZ BZ BB11 H H H IZ4-460 EOE EOE BB14 H H H
IZ4-421 EOE EOE BB11 H H H IZ4-461 ALL ALL BB14 H H H
IZ4-422 ALL ALL BB11 H H H IZ4-462 CBA CBA BB14 H H H
IZ4-423 CBA CBA BB11 H H H IZ4-463 HYE HYE BB14 H H H
IZ4-424 HYE HYE BB11 H H H IZ4-464 NA1 NA1 BB14 H H H
IZ4-425 NA1 NA1 BB11 H H H IZ4-465 HHk8 HHk8 BB14 H H H
IZ4-426 HHk8 HHk8 BB11 H H H IZ4-466 NA2 NA2 BB14 H H H
IZ4-427 NA2 NA2 BB11 H H H IZ4-467 HHk7 HHk7 BB14 H H H
IZ4-428 HHk7 HHk7 BB11 H H H IZ4-468 HH37 HH37 BB14 H H H
IZ4-429 HH37 HH37 BB11 H H H IZ4-469 HHk6 HHk6 BB14 H H H
IZ4-430 HHk6 HHk6 BB11 H H H IZ4-470 NA3 NA3 BB14 H H H
IZ4-431 NA3 NA3 BB11 H H H IZ4-471 HHJ2 HHJ2 BB14 H H H
IZ4-432 HHJ2 HHJ2 BB11 H H H IZ4-472 HHk11 HHk11 BB14 H H H
IZ4-433 HHk11 HHk11 BB11 H H H IZ4-473 Et Me BB14 H H H
IZ4-434 Et Me BB11 H H H IZ4-474 PH Me BB14 H H H
IZ4-435 PH Me BB11 H H H IZ4-475 Oct Me BB14 H H H
IZ4-436 Oct Me BB11 H H H IZ4-476 CHM Me BB14 H H H
IZ4-437 CHM Me BB11 H H H IZ4-477 CH Me BB14 H H H
IZ4-438 CH Me BB11 H H H IZ4-478 BZ Me BB14 H H H
IZ4-439 BZ Me BB11 H H H IZ4-479 EOE Me BB14 H H H
IZ4-440 EOE Me BB11 H H H IZ4-480 ALL Me BB14 H H H
IZ4-441 ALL Me BB11 H H H IZ4-481 CBA Me BB14 H H H
[ Table 13Z4]
TABLE 13Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4 RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-482 HYE Me BB14 H H H IZ4-522 Oct Oct BB37 H H H
IZ4-483 NA1 Me BB14 H H H IZ4-523 CHM CHM BB37 H H H
IZ4-484 HHk8 Me BB14 H H H IZ4-524 CH CH BB37 H H H
IZ4-485 NA2 Me BB14 H H H IZ4-525 BZ BZ BB37 H H H
IZ4-486 HHk7 Me BB14 H H H IZ4-526 ALL ALL BB37 H H H
IZ4-487 HH37 Me BB14 H H H IZ4-527 CBA CBA BB37 H H H
IZ4-488 HHk6 Me BB14 H H H IZ4-528 HYE HYE BB37 H H H
IZ4-489 NA3 Me BB14 H H H IZ4-529 NA1 NA1 BB37 H H H
IZ4-490 HHJ2 Me BB14 H H H IZ4-530 HHk8 HHk8 BB37 H H H
IZ4-491 HHk11 Me BB14 H H H IZ4-531 NA2 NA2 BB37 H H H
IZ4-492 NA1 NA1 BB19 H H H IZ4-532 HHk7 HHk7 BB37 H H H
IZ4-493 HHk8 HHk8 BB19 H H H IZ4-533 HH37 HH37 BB37 H H H
IZ4-494 NA2 NA2 BB19 H H H IZ4-534 HHk6 HHk6 BB37 H H H
IZ4-495 HHk7 HHk7 BB19 H H H IZ4-535 NA3 NA3 BB37 H H H
IZ4-496 HH37 HH37 BB19 H H H IZ4-536 HHJ2 HHJ2 BB37 H H H
IZ4-497 HHk6 HHk6 BB19 H H H IZ4-537 HHk11 HHk11 BB37 H H H
IZ4-498 NA3 NA3 BB19 H H H IZ4-538 Et Me BB37 H H H
IZ4-499 HHJ2 HHJ2 BB19 H H H IZ4-539 PH Me BB37 H H H
IZ4-500 HHk11 HHk11 BB19 H H H IZ4-540 Oct Me BB37 H H H
IZ4-501 Et Me BB19 H H H IZ4-541 CHM Me BB37 H H H
IZ4-502 PH Me BB19 H H H IZ4-542 CH Me BB37 H H H
IZ4-503 Oct Me BB19 H H H IZ4-543 BZ Me BB37 H H H
IZ4-504 CHM Me BB19 H H H IZ4-544 EOE Me BB37 H H H
IZ4-505 CH Me BB19 H H H IZ4-545 ALL Me BB37 H H H
IZ4-506 EOE Me BB19 H H H IZ4-546 CBA Me BB37 H H H
IZ4-507 ALL Me BB19 H H H IZ4-547 HYE Me BB37 H H H
IZ4-508 CBA Me BB19 H H H IZ4-548 NA1 Me BB37 H H H
IZ4-509 HYE Me BB19 H H H IZ4-549 HHk8 Me BB37 H H H
IZ4-510 NA1 Me BB19 H H H IZ4-550 NA2 Me BB37 H H H
IZ4-511 HHk8 Me BB19 H H H IZ4-551 HHk7 Me BB37 H H H
IZ4-512 NA2 Me BB19 H H H IZ4-552 HH37 Me BB37 H H H
IZ4-513 HHk7 Me BB19 H H H IZ4-553 HHk6 Me BB37 H H H
IZ4-514 HH37 Me BB19 H H H IZ4-554 NA3 Me BB37 H H H
IZ4-515 HHk6 Me BB19 H H H IZ4-555 HHJ2 Me BB37 H H H
IZ4-516 NA3 Me BB19 H H H IZ4-556 HHk11 Me BB37 H H H
IZ4-517 HHJ2 Me BB19 H H H IZ4-557 Me Me BB58 H H H
IZ4-518 HHk11 Me BB19 H H H IZ4-558 Et Et BB58 H H H
IZ4-519 Me Me BB37 H H H IZ4-559 PH PH BB58 H H H
IZ4-520 Et Et BB37 H H H IZ4-560 Oct Oct BB58 H H H
IZ4-521 PH PH BB37 H H H IZ4-561 CHM CHM BB58 H H H
[ Table 14Z4]
TABLE 14Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4 RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-562 CH CH BB58 H H H IZ4-602 EOE EOE BBJ2 H H H
IZ4-563 BZ BZ BB58 H H H IZ4-603 ALL ALL BBJ2 H H H
IZ4-564 EOE EOE BB58 H H H IZ4-604 CBA CBA BBJ2 H H H
IZ4-565 CBA CBA BB58 H H H IZ4-605 HYE HYE BBJ2 H H H
IZ4-566 HYE HYE BB58 H H H IZ4-606 NA1 NA1 BBJ2 H H H
IZ4-567 NA1 NA1 BB58 H H H IZ4-607 HHk8 HHk8 BBJ2 H H H
IZ4-568 HHk8 HHk8 BB58 H H H IZ4-608 NA2 NA2 BBJ2 H H H
IZ4-569 NA2 NA2 BB58 H H H IZ4-609 HHk7 HHk7 BBJ2 H H H
IZ4-570 HHk7 HHk7 BB58 H H H IZ4-610 HH37 HH37 BBJ2 H H H
IZ4-571 HH37 HH37 BB58 H H H IZ4-611 HHk6 HHk6 BBJ2 H H H
IZ4-572 HHk6 HHk6 BB58 H H H IZ4-612 NA3 NA3 BBJ2 H H H
IZ4-573 NA3 NA3 BB58 H H H IZ4-613 HHJ2 HHJ2 BBJ2 H H H
IZ4-574 HHJ2 HHJ2 BB58 H H H IZ4-614 HHk11 HHk11 BBJ2 H H H
IZ4-575 HHk11 HHk11 BB58 H H H IZ4-615 Et Me BBJ2 H H H
IZ4-576 Et Me BB58 H H H IZ4-616 PH Me BBJ2 H H H
IZ4-577 PH Me BB58 H H H IZ4-617 Oct Me BBJ2 H H H
IZ4-578 Oct Me BB58 H H H IZ4-618 CHM Me BBJ2 H H H
IZ4-579 CHM Me BB58 H H H IZ4-619 CH Me BBJ2 H H H
IZ4-580 CH Me BB58 H H H IZ4-620 BZ Me BBJ2 H H H
IZ4-581 BZ Me BB58 H H H IZ4-621 EOE Me BBJ2 H H H
IZ4-582 EOE Me BB58 H H H IZ4-622 ALL Me BBJ2 H H H
IZ4-583 ALL Me BB58 H H H IZ4-623 CBA Me BBJ2 H H H
IZ4-584 CBA Me BB58 H H H IZ4-624 HYE Me BBJ2 H H H
IZ4-585 HYE Me BB58 H H H IZ4-625 NA1 Me BBJ2 H H H
IZ4-586 NA1 Me BB58 H H H IZ4-626 HHk8 Me BBJ2 H H H
IZ4-587 HHk8 Me BB58 H H H IZ4-627 NA2 Me BBJ2 H H H
IZ4-588 NA2 Me BB58 H H H IZ4-628 HHk7 Me BBJ2 H H H
IZ4-589 HHk7 Me BB58 H H H IZ4-629 HH37 Me BBJ2 H H H
IZ4-590 HH37 Me BB58 H H H IZ4-630 HHk6 Me BBJ2 H H H
IZ4-591 HHk6 Me BB58 H H H IZ4-631 NA3 Me BBJ2 H H H
IZ4-592 NA3 Me BB58 H H H IZ4-632 HHJ2 Me BBJ2 H H H
IZ4-593 HHJ2 Me BB58 H H H IZ4-633 HHk11 Me BBJ2 H H H
IZ4-594 HHk11 Me BB58 H H H IZ4-634 Me Me BBO8 H H H
IZ4-595 Me Me BBJ2 H H H IZ4-635 Et Et BBO8 H H H
IZ4-596 Et Et BBJ2 H H H IZ4-636 PH PH BBO8 H H H
IZ4-597 PH PH BBJ2 H H H IZ4-637 Oct Oct BBO8 H H H
IZ4-598 Oct Oct BBJ2 H H H IZ4-638 CHM CHM BBO8 H H H
IZ4-599 CHM CHM BBJ2 H H H IZ4-639 CH CH BBO8 H H H
IZ4-600 CH CH BBJ2 H H H IZ4-640 BZ BZ BBO8 H H H
IZ4-601 BZ BZ BBJ2 H H H IZ4-641 EOE EOE BBO8 H H H
[ Table 15Z4]
TABLE 15Z4
RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4 RN1Z4 RN2Z4 Ba1Z4Ba2Z4 R1Z4 R6Z4 R7Z4
IZ4-642 ALL ALL BBO8 H H H IZ4-682 CBA CBA BBO10 H H H
IZ4-643 CBA CBA BBO8 H H H IZ4-683 HYE HYE BBO10 H H H
IZ4-644 HYE HYE BBO8 H H H IZ4-684 NA1 NA1 BBO10 H H H
IZ4-645 NA1 NA1 BBO8 H H H IZ4-685 HHk8 HHk8 BBO10 H H H
IZ4-646 HHk8 HHk8 BBO8 H H H IZ4-686 NA2 NA2 BBO10 H H H
IZ4-647 NA2 NA2 BBO8 H H H IZ4-687 HHk7 HHk7 BBO10 H H H
IZ4-648 HHk7 HHk7 BBO8 H H H IZ4-688 HH37 HH37 BBO10 H H H
IZ4-649 HH37 HH37 BBO8 H H H IZ4-689 HHk6 HHk6 BBO10 H H H
IZ4-650 HHk6 HHk6 BBO8 H H H IZ4-690 NA3 NA3 BBO10 H H H
IZ4-651 NA3 NA3 BBO8 H H H IZ4-691 HHJ2 HHJ2 BBO10 H H H
IZ4-652 HHJ2 HHJ2 BBO8 H H H IZ4-692 HHk11 HHk11 BBO10 H H H
IZ4-653 HHk11 HHk11 BBO8 H H H IZ4-693 Et Me BBO10 H H H
IZ4-654 Et Me BBO8 H H H IZ4-694 PH Me BBO10 H H H
IZ4-655 PH Me BBO8 H H H IZ4-695 Oct Me BBO10 H H H
IZ4-656 Oct Me BBO8 H H H IZ4-696 CHM Me BBO10 H H H
IZ4-657 CHM Me BBO8 H H H IZ4-697 CH Me BBO10 H H H
IZ4-658 CH Me BBO8 H H H IZ4-698 BZ Me BBO10 H H H
IZ4-659 BZ Me BBO8 H H H IZ4-699 EOE Me BBO10 H H H
IZ4-660 EOE Me BBO8 H H H IZ4-700 ALL Me BBO10 H H H
IZ4-661 ALL Me BBO8 H H H IZ4-701 CBA Me BBO10 H H H
IZ4-662 CBA Me BBO8 H H H IZ4-702 HYE Me BBO10 H H H
IZ4-663 HYE Me BBO8 H H H IZ4-703 NA1 Me BBO10 H H H
IZ4-664 NA1 Me BBO8 H H H IZ4-704 HHk8 Me BBO10 H H H
IZ4-665 HHk8 Me BBO8 H H H IZ4-705 NA2 Me BBO10 H H H
IZ4-666 NA2 Me BBO8 H H H IZ4-706 HHk7 Me BBO10 H H H
IZ4-667 HHk7 Me BBO8 H H H IZ4-707 HH37 Me BBO10 H H H
IZ4-668 HH37 Me BBO8 H H H IZ4-708 HHk6 Me BBO10 H H H
IZ4-669 HHk6 Me BBO8 H H H IZ4-709 NA3 Me BBO10 H H H
IZ4-670 NA3 Me BBO8 H H H IZ4-710 HHJ2 Me BBO10 H H H
IZ4-671 HHJ2 Me BBO8 H H H IZ4-711 HHk11 Me BBO10 H H H
IZ4-672 HHk11 Me BBO8 H H H IZ4-712 HH9 HHf5 BB2 H H H
IZ4-673 Me Me BBO10 H H H IZ4-713 HHh1 HHj19 BB3 H H H
IZ4-674 Et Et BBO10 H H H IZ4-714 HH55 HH81 BB4 H H H
IZ4-675 PH PH BBO10 H H H IZ4-715 HHf1 HHi11 BB5 H H H
IZ4-676 Oct Oct BBO10 H H H IZ4-716 NA5 HHJ10 BB7 H H H
IZ4-677 CHM CHM BBO10 H H H IZ4-717 HHk7 HHc1 BB9 H H H
IZ4-678 CH CH BBO10 H H H IZ4-718 HHf11 HH28 BB10 H H H
IZ4-679 BZ BZ BBO10 H H H IZ4-719 HH13 HH46 BB12 H H H
IZ4-680 EOE EOE BBO10 H H H IZ4-720 HHJ4 HH78 BB13 H H H
IZ4-681 ALL ALL BBO10 H H H IZ4-721 HHb3 HH22 BB15 H H H
[ Table 16Z4]
TABLE 16Z4
Figure BDA0003121580680002651
For example, the compound IZ4-1 is a compound represented by the formula (IZ 4-1).
Figure BDA0003121580680002652
The compound IZ4 is preferably a compound IZ4-1 to a compound IZ4-234 and a compound IZ4-321 to a compound IZ4-769, more preferably a compound IZ4-1 to a compound IZ4-234 and a compound IZ4-321 to a compound IZ4-711, still more preferably a compound IZ4-1 to a compound IZ4-234, yet more preferably a compound IZ4-1 to a compound IZ4-174, particularly preferably a compound IZ4-1 to a compound IZ4-117,
particularly preferred are the compound IZ4-1 to the compound IZ4-2, the compound IZ4-40 to the compound IZ4-41, and the compound IZ4-79 to the compound IZ 4-80.
Specific examples of the compound IZ4 include compounds represented by table 1Z4, table 2Z4, table 3Z4, table 4Z4, table 5Z4, table 6Z4, table 7Z4, table 8Z4, and tables 11Z4 to 16Z4, in which 1 to 3 hydrogen atoms contained in the compounds are replaced by — SO3M or-CO2M is substituted. For example, compounds having 1 to 3 sulfo groups bonded to the compound IZ4-1 of Table 1Z4 are represented by the following structures. Wherein, in the formula, - (SO)3H) Represents a compound in which any hydrogen atom in compound IZ4-1 of Table 1Z4 is substituted.
Figure BDA0003121580680002661
In the present invention, it is preferable that 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-234 and the compound IZ4-321 to the compound IZ4-7693M or-CO2More preferably, the compound of M is a compound in which 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-234 and the compound IZ4-321 to the compound IZ4-711 3M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-2343M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-1743M or-CO2A compound formed by the reaction of M,
particularly preferably, 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-1173M or-CO2A compound formed by the reaction of M,
particularly preferably, 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-2, the compound IZ4-40 to the compound IZ4-41, and the compound IZ4-79 to the compound IZ4-803M or-CO2M, or a salt thereof.
Figure BDA0003121580680002671
As the compound (IZ4), the following compounds are preferable:
in the formula (IZ4), RN1Z4And RN2Z4Independently of one another are-CO-R102Z4、-COO-R101Z4、-CON(R102Z4)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R1Z4Is a hydrogen atom and may have a radical selected from the group consisting of-SO3M and-CO2Taking of group consisting of MA substituted hydrocarbon group having 1 to 20 carbon atoms, -SO3M or-CO2M,
R2Z4~R5Z4Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z4)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102Z4、-O-R102Z4、-SO3M or-CO2M,R6Z4And R7Z4Independently of one another, a hydrogen atom, may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,R102Z4Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R101Z4May have a structure selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 20 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
RN1Z4and RN2Z4Independently of one another are-CO-R102Z4、-CON(R102Z4)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R1Z4Is a hydrogen atom, R2Z4~R5Z4Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z4)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z4、-O-R102Z4、-SO3M or-CO2M,
R6Z4And R7Z4Are the same group, are hydrogen atoms, or may have a structure selected from the group consisting of3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R102Z4is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2a C1-10 hydrocarbon group as a substituent in the group consisting of M, R 101Z4May have a structure selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
RN1Z4and RN2Z4Independently of one another are-CO-R102Z4、-CON(R102Z4)2Or may have a structure selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1Z4is a hydrogen atom, R2Z4~R5Z4Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z4)2Nitro, trifluoromethyl, -O-R102Z4、-SO3M or-CO2M,
R6Z4And R7Z4The same group is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, R102Z4Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R101Z4may have a structure selected from the group consisting of-SO3M and-CO2And M is a compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms and M is a hydrogen atom or an alkali metal atom.
For compound IZ4, R1Z4In the case of a hydrogen atom, the compound represented by the formula (pt1Z4) (hereinafter, may be referred to as a phthalonitrile compound) may be produced by reacting a compound represented by the formula (pt2Z4) (hereinafter, may be referred to as an alkoxide compound), and then further reacting the compound represented by the formula (pt3Z4) and the compound represented by the formula (pt4Z4) in the presence of an acid. In addition, R 1Z4When not a hydrogen atom, the compound is further reacted with a compound represented by the formula (pt5Z4) to produce a compound IZ 4.
Figure BDA0003121580680002691
In [ formula (pt1Z4), formula (pt2Z4), formula (pt3Z4), formula (pt4Z4), formula (pt5Z4) and formula (IZ4), RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4And R7Z4The same meanings as described above are indicated. R14Z4Represents an alkyl group having 1 to 20 carbon atoms. M1Z4Represents an alkali metal atom. LG represents a halogen atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group.]
As R14Z4Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z4Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom. The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z4 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z4 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z4, and the compound pt4Z4 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; 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 acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound. The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z4 used, relative to R1Z4The amount of the compound IZ41 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
When the compound pt5Z4 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1Z4The amount of the compound IZ41 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
The reaction of compound pt5Z4 can generally be carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1Z4The amount of the compound IZ 41 is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z4 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound IZ4 having no sulfo group or-SO3M2In the case of (3), the compound IZ4 can be reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to introduce a sulfo group or-SO3M22
M22Represents an alkali metal atom. As M22Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
With respect to SO in oleum3The amount of (b) is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and still more preferably 5 to 25 mol based on 41 mol of the compound IZ.
The amount of sulfuric acid used in the oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on 41 moles of the compound IZ.
The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on 41 moles of the compound IZ.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound IZ4 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is filtered to extract the compound IZ 4. Further, the residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After the completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
< Compound IZ5 >)
Compound IZ5 is represented by formula (IZ 5).
Figure BDA0003121580680002721
[ formula (IZ5), RN1Z5represents-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5And R7Z5Independently of one another, represents a hydrogen atom, -CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Each of which may be bonded to each other to form a ring, R2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R 102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5At least one group of them is bonded to form a ring.
R101Z5The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
R102Z5Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z5、R102Z5And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The number of carbon atoms of the optionally substituted hydrocarbon group is 1 to 40, preferably 1 to 401 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and particularly preferably 1 to 5.
RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, further more preferably 1 to 8, and particularly preferably 1 to 5. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable, and a methyl group, an ethyl group, and a tert-butyl group are particularly preferable.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5A saturated or unsaturated alicyclic hydrocarbon group represented byExamples thereof include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1, 2-dimethylcyclohexyl group, 1, 3-dimethylcyclohexyl group, 1, 4-dimethylcyclohexyl group, 2, 3-dimethylcyclohexyl group, 2, 4-dimethylcyclohexyl group, 2, 5-dimethylcyclohexyl group, 2, 6-dimethylcyclohexyl group, 3, 4-dimethylcyclohexyl group, 3, 5-dimethylcyclohexyl group, 2-dimethylcyclohexyl group, 3-dimethylcyclohexyl group, 4-dimethylcyclohexyl group, cyclooctyl group, 2,4, 6-trimethylcyclohexyl group, 2,6, 6-tetramethylcyclohexyl group and 3, cycloalkyl groups such as 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, and cyclooctenyl; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl are particularly preferable.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a mesityl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a, Aromatic hydrocarbon groups such as 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracyl, pyrenyl and the like; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further more preferably 6 to 20Preferably 6 to 15.
RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5Examples of the group represented by the above-mentioned groups, which are a combination of the above-mentioned hydrocarbon groups (e.g., chain hydrocarbon groups and alicyclic hydrocarbon groups), include alkyl groups to which 1 or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl groups, cyclopropylethyl groups, cyclobutylmethyl groups, cyclobutylethyl groups, cyclopentylmethyl groups, cyclopentylethyl groups, cyclohexylmethyl groups, 2-methylcyclohexylmethyl groups, cyclohexylethyl groups, and adamantylmethyl groups. The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group represented may have a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
Figure BDA0003121580680002761
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl;
a formyl group; a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
Figure BDA0003121580680002771
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
Figure BDA0003121580680002772
Figure BDA0003121580680002781
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formula);
Figure BDA0003121580680002791
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, N-phenylmethylsulfamoyl, and the like, and groups represented by the following chemical formulae);
Figure BDA0003121580680002801
Figure BDA0003121580680002811
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
Figure BDA0003121580680002812
Figure BDA0003121580680002821
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is an alkali metal, preferably lithium, sodium, potassium); a nitro group; a cyano group;
a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
Figure BDA0003121580680002822
Figure BDA0003121580680002831
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
Figure BDA0003121580680002832
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
Figure BDA0003121580680002841
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, and a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3and-CO-S-CH2-CH2-CH2-CH3Or a thiocarbonyl group, -CO-S-C, bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) 6H5A thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms;
a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
Figure BDA0003121580680002851
-NRCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
Figure BDA0003121580680002861
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and R's may be the same or different from each other, and may be mutually different Bonded to form a ring);
Figure BDA0003121580680002871
a group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
Figure BDA0003121580680002881
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR3(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring); and so on.
Examples of the substituent having a valence of 2 include an oxo group, a thioxo 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. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom; -CO 2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; fluorine atomA hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted; a hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
An amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a hydroxyl group; fluorine atom, chlorine atom, bromine atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent;
a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group having 1 to 40 carbon atoms and having a substituent represented by the formula (I) includes a hydrocarbon group having 1 to 40 carbon atoms and having a substituent having a valence of 1 or 2, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, and a group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which are a combination of hydrocarbon groups,
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups having 1 to 20 carbon atoms having a substituent of group s1,
particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 1 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The heterocyclic group represented by (a) may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include:
monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole;
a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine;
a fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane; bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone; five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran; fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole, chroman and isochroman; fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include:
five-membered ring system saturated heterocycles such as dithiolane;
saturated heterocyclic rings of six-membered ring systems such as thiacyclohexane, 1, 3-dithiane, 2-methyl-1, 3-dithiane and the like;
a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran);
fused bicyclic heterocycles such as benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone; a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole); fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
Figure BDA0003121580680002921
The above heterocyclic group may be R1Z5~R5Z52 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1Z5~R5Z5The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
Figure BDA0003121580680002922
The bonding position of the heterocycle is a portion where any hydrogen atom contained in each ring is removed.
RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The heterocyclic group represented may have a substituent. Examples of the substituent includeN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group may have the same substituent as the substituent. In addition, in the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom. Preferred examples of the substituent includeN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The preferable examples of the substituents which the hydrocarbon group may have are the same.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The heterocyclic group having a substituent represented by the formula (i) includes a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s 2.
The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. As for the above-mentioned first substituent, another substituent (second substituent) may be bonded to the hydrocarbon group contained in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5And R7Z5Of (a) is-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, -SO3M、-CO2M is explained.
as-CO-R102Z5Examples thereof include a formyl group; acetyl, propionyl, butyryl, 2-dimethylpropionyl, pentanoyl, hexanoyl, (2-ethyl) hexanoyl, heptanoyl, examples of the carbonyl group include a carbonyl group (in the case where the carbonyl group is an acyl group, the number of carbon atoms is 2 to 41) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyl group, a nonanoyl group, a decanoyl group, a undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group, and the compounds shown in tables 1Z5 to 7Z5 and 10Z5 to 13Z5 correspond to — CO — R.102Z5Preferable examples of the group(s) include a carbonyl group (more preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 correspond to-CO-R 102Z5And the like.
as-COO-R101Z5Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl, eicosyloxycarbonyl and the like, and hydrocarbyl groups having 1 to 40 (preferably 1 to 20) carbon atoms or derived groups thereof (for example, through carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylaminosulfonyl groups having 1 to 10 carbon atoms (preferably through carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom)) are bonded to groups represented by the above formulaeOctyl sulfamoyl) and the like) and the corresponding-COO-R in the compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5102Z5Preferred examples of the group (b) include oxycarbonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 which correspond to-COO-R102Z5And the like.
as-OCO-R102Z5Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy and the like, carbonyloxy (having 2 to 41 carbon atoms in the case where the carbonyloxy group is an acyloxy group), carbonyloxy having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) bonded to a group represented by the above formula) and the like, And those shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 correspond to-OCO-R 102Z5Preferable examples of the group(s) include a carbonyloxy group (more preferably 2 to 12 carbon atoms when the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 corresponds to-OCO-R102Z5And the like.
as-COCO-R102Z5Examples thereof include methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) hexyloxalyl, heptyloxalyl, octyloxalyl, nonyloxalyl, decyloxyl, undecyloxalyl, dodecyloxalyl, eicosanoyl, cyclopentyloxalyl, cyclohexyloxalyl, phenyloxalyl, p-tolyloxalyl and the like,And oxalyl groups in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded to a group represented by the above formula, and compounds represented by tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 corresponding to-COCO-R 102Z5And the like.
as-O-R102Z5Examples of the group include a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 5-dimethylphenyloxy, 2, 6-dimethylphenyloxy, 3, 4-dimethylphenyloxy, 3, 5-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 3-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 4-di-yloxy, 2-di-methyl-1-phenylethoxy, 2, 4-di-methyl, and mixtures thereof, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, examples of the oxygen group include an oxygen group having a hydrocarbyl group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like bonded thereto, such as a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or the like, and a group represented by the above chemical formulae), and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 correspond to — O — R. 102Z5Preferred examples of the group (b) include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5, which correspond to-O-R102Z5And the like.
as-SO2-R101Z5Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl) hexylsulfonyl, heptylsulfonyl, octylsulfonyl, nonyl sulfonyl, decyl sulfonyl, undecyl sulfonyl, dodecyl sulfonyl, eicosyl sulfonyl, phenyl sulfonyl, p-tolyl sulfonyl, and the like, and sulfonyl groups in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like is bonded, such as the group represented by the above chemical formula, and-SO corresponds to the compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z 5.2-R102Z5Preferable examples of the group (b) include sulfonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds represented by tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5, which correspond to-SO 2-R102Z5And the like.
as-SO2N(R102Z5)2Examples thereof include:
a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl, N-phenylsulfamoyl, etc., and a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula, or a derivative thereof Sulfamoyl groups substituted with a raw group (e.g., a group derived from carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group)), and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 correspond to the above groups-SO2NH(R102Z5X) (wherein, R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above), etc.;
N, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylsulfamoyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diethylsulfamoyl, N, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylmethylsulfamoyl, N-phenylmethylsulfamoyl, N-diphenylsulfamoyl and the like, and sulfamoyl groups represented by the above chemical formulae and the like substituted with a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl) and the like), and sulfamoyl groups shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 Corresponding to-SO in the compound 2N(R102Z5X)2(wherein, R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above) and the like,
preferred examples thereof include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof, and compounds represented by tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5, which correspond to-SO2N(R102Z5)2And the like.
as-CON (R)102Z5)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylA hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, an N-isopropylcarbamoyl group, an N-butylcarbamoyl group, an N-isobutylcarbamoyl group, an N-sec-butylcarbamoyl group, an N-tert-butylcarbamoyl group, an N-pentylcarbamoyl group, an N- (1-ethylpropyl) carbamoyl group, an N-hexylcarbamoyl group, an N- (2-ethyl) hexylcarbamoyl group, an N-heptylcarbamoyl group, an N-octylcarbamoyl group, an N-nonylcarbamoyl group, an N-decylcarbamoyl group, an N-undecylcarbamoyl group, an N-dodecylcarbamoyl group, an N-eicosylcarbamoyl group, an N-phenylcarbamoyl group and the like, and a group represented by the above chemical formula A carbamoyl group substituted with a group derived from sulfo, nitro, hydroxy, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), or the like), and a compound shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 corresponds to-CONH (R is 102Z5X) (wherein, R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above), etc.;
n, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-tert-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-diethylcarbamoyl group, N-diisopropylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-isobutylcarbamoyl group, N-di (s-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-di-N-butylcarbamoyl group, N, n, N-dihexylcarbamoyl group, N-di (2-ethyl) hexylcarbamoyl group, N-diheptylcarbamoyl group, N-octylmethylcarbamoyl group, N-dioctylcarbamoyl group, N-dinonylcarbamoyl group, N-decylmethylcarbamoyl group, N-undecylmethylcarbamoyl group, N-dodecylmethylcarbamoyl group, N-eicosylmethylcarbamoyl group, N-phenylmethylcarbamoyl group, N-diphenylcarbamoyl group, etc., and the above Carbamoyl groups such as the group represented by the above chemical formula, which are substituted with 2C 1-40 (preferably C1-20) hydrocarbon groups or derivative groups thereof (e.g., groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), C1-10 alkylsulfamoyl (preferably octylsulfamoyl), etc.), and compounds shown in tables 1Z 5-7Z 5 and tables 10Z 5-13Z 5 which correspond to-CON (R)102Z5X)2(R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z5 to 7Z5 and 10Z5 to 13Z5 which corresponds to-CON (R)102Z5)2And the like.
as-N (R)102Z5)2Examples thereof include:
an amino group; a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom)), such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, an N-tert-butylamino group, an N-pentylamino group, an N-hexylamino group, an N- (2-ethyl) hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-undecylamino group, an N-dodecylamino group, an N-eicosylamino group, an N-phenylamino group, and the like, and a group represented by the above chemical formula, A group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like) and a compound shown in tables 1Z5 to 7Z5 and 10Z5 to 13Z5, wherein the compound corresponds to-NH (R 102Z5X)(R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above), etc.;
n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-t-butylmethylamino group, N-diisobutylamino groupA hydrocarbon group having 2 carbon atoms of 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a di-sec-butylamino group, an N, N-di-tert-butylamino group, an N, N-butylmethylamino group, an N, N-dibutylamino group, an N, N-dipentylamino group, an N, N-di (1-ethylpropyl) amino group, an N, N-dihexylamino group, an N, N-di (2-ethyl) hexylamino group, an N, N-diheptylamino group, an N, N-dioctylamino group, an N, N-dinonylamino group, an N, N-decylmethylamino group, an N, N-undecylmethylamino group, an N, N-dodecylmethylamino group, an N, N-eicosylmethylamino group, an N, N-phenylmethylamino group, an N, N-diphenylamino group, etc., and a group represented by the above chemical formula, A derivative of sulfo, nitro, hydroxy, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), or the like) and a compound shown in tables 1Z5 to 7Z5 and 10Z5 to 13Z5, wherein the compound corresponds to-N (R 102Z5X)2(wherein, R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above) and the like,
preferred examples thereof include amino groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 which correspond to-N (R)102Z5)2And the like.
as-NHCO-R102Z5Examples thereof include formylamino; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (in the case where the carbonylamino group is an acylamino group, the carbon number is 1 to 40), wherein a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded to an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, a benzoylamino group, or the like, or a group represented by the above chemical formula), and tables 1Z5 to 7Z5 and tables. 10Z5 to Table 13Z5 correspond to-NHCO-R102Z5And the like,
preferred examples thereof include carbonylamino groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded (in the case where the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10), and compounds represented by tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5, which correspond to-NHCO-R102Z5And the like.
as-NHCON (R)102Z5)2Examples thereof include the groups listed above and the compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 which correspond to-NHCON (R)102Z5)2And the like.
as-NHCOOR102Z5Examples thereof include those corresponding to-NHCOOR among the above-mentioned groups and the compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5102Z5And the like.
as-OCON (R)102Z5)2Examples thereof include those corresponding to-OCON (R) among the above-mentioned groups and the compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5102Z5)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M in M is a hydrogen atom; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102Z5、-COO-R102Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R102Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCON(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
R2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 5). As R2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, and benzo [9,10 ] ene]Phenanthrene, pyrene,
Figure BDA0003121580680003011
Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide and butachlor, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, etc.); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,
Figure BDA0003121580680003012
Nitrogen-containing fused heterocycles such as pyridine, phenanthroline, and phenazine, and partial reductants thereof; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5In the case of forming a ring, the ring may have a substituent. Examples of the substituent include N1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent includeN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3Z5And R4Z5When forming a ring, as R2Z5And R5Z5Independently of one another, hydrogen atoms, amino groups and hydroxyl groups are preferred.
R2Z5And R3Z5When a ring is formed, R is preferably4Z5And R5Z5Does not form a ring, more preferably R4Z5And R5Z5Is a hydrogen atom.
R4Z5And R5Z5When a ring is formed, R is preferably2Z5And R3Z5Does not form a ring, more preferably R2Z5And R3Z5Is a hydrogen atom. R1Z5、R6Z5And R7Z5Preferably a hydrogen atom.
RN1Z5preferably-CO-R102Z5、-COO-R101Z5、-CON(R102Z5)2、-N(R102Z5)2、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, more preferably a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, still more preferably a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, particularly preferably a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, still more preferably a methyl group, an ethyl group or a phenyl group, and most preferably a methyl group or an ethyl group.
From the viewpoint of reducing the retardation value of the color filter formed from the colored composition, R is preferable2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, more preferably a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a halogen atom, -N (R)102Z5)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Alternatively, R is preferred2Z5And R3Z5、R3Z5And R4Z5Or R4Z5And R5Z5Form a ring.
From the viewpoint of reducing the retardation value of the color filter formed from the colored composition, R is preferable2Z5、R3Z5、R4Z5And R5Z5At least one of which is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, or-N (R)102Z5)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M,
More preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Among them, it is still more preferable that R 3Z5Is nitro or tert-butyl, R2Z5、R4Z5And R5Z5Is a hydrogen atom; or, R2Z5、R3Z5And R5Z5Is a hydrogen atom, R4Z5Is nitro or tert-butyl.
Specific examples of compound IZ5 include compounds IZ5-1 to IZ5-1 having substituents shown in table 1Z5, table 2Z5, table 3Z5, table 4Z5, table 5Z5, table 6Z5, table 7Z5, and table 10Z5 to table 13Z5 in formula (IZ5-aa)IZ5-542 or an alkali metal salt thereof. B isa1Z5Ba2Z5The partial structure represented by any one of formulae (BB2) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) is shown. The formulae (BB2) to (BB60), (BBK2), (BBK3), (BBK4), (BBK14), (BBI1), (BBO8), (BBO10), (BBD1) and (BBJ2) are the same as B representing formula (IZ1-aa)a1Z1Ba2Z1The same structures as (BB2) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) described above. B isa1Z5And Ba2Z5Each represents a chemical bond, Ba1Z5B of formulae (BB2) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2)1When a chemical bond of (A) is present, Ba2Z5To be B2The chemical bond of (a); b isa1Z5B of formulae (BB2) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) 2When a chemical bond of (A) is present, Ba2Z5To be B1The chemical bond of (1). As Ba1Z5Ba2Z5Formula (BB6), formula (BB8), formula (BB11), formula (BB14), formula (BB19), formula (BB37), formula (BB58), formula (BBJ2), formula (BBO8), and formula (BBO10) are preferable, and formula (BB6) and formula (BB19) are more preferable.
Figure BDA0003121580680003031
Each symbol in table 1Z5, table 2Z5, table 3Z5, table 4Z5, table 5Z5, table 6Z5, table 7Z5, and tables 10Z5 to table 13Z5 represents the following partial structure. In the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group, "Hex" represents a hexyl group, "Oct" represents an octyl group, "2 EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group, "CH" represents a cyclohexyl group, "PH" represents a phenyl group, "BZ" represents a benzyl group, "NPR" represents a propyl group, "IPR" represents an isopropyl group, "IBu" represents an isobutyl group, and "EOE"represents-CH2CH2OCH2CH3"ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents-CO-CH3And "COE" represents-COO-CH2CH3And "OCM" represents-OCO-CH3And "OME" represents-O-CH3"SOT" represents a tosyl group, and "SNH" represents-SO2NH-CH2CH(CH2CH3)((CH2)3CH3) "SN 2" represents-SO2N(CH3)((CH2)7CH3) "CNM" represents-CONHCH 3And "CN 2" represents-CON (CH)3)C6H5And "NPH" represents-NHC6H5And "NOT" represents-N ((CH)2)7CH3)2And "NCO" represents-NHCO ((CH)2)4CH3) "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO 2" represents a nitro group, and "SUA" represents-SO3H, "CBA" means-CO2H, "CHO" means-CHO, "OCH" means-OCOH, "OH" means-OH, "SFM" means-SO2NH2"CBM" represents-CONH2"NH 2" means-NH2"NCH" represents-nhcooh, and represents a chemical bond. In the table, the following partial structures are denoted by symbols.
Figure BDA0003121580680003041
Figure BDA0003121580680003051
Figure BDA0003121580680003061
[ Table 1Z5]
TABLE 1Z5
RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5
IZ5-1 Me BB6 H H H
IZ5-2 Et BB6 H H H
IZ5-3 PH BB6 H H H
IZ5-4 Bu BB6 H H H
IZ5-5 TBu BB6 H H H
IZ5-6 Hex BB6 H H H
IZ5-7 Oct BB6 H H H
IZ5-8 2EH BB6 H H H
IZ5-9 CHM BB6 H H H
IZ5-10 CH BB6 H H H
IZ5-11 BZ BB6 H H H
IZ5-12 NPR BB6 H H H
IZ5-13 IPR BB6 H H H
IZ5-14 IBu BB6 H H H
IZ5-15 EOE BB6 H H H
IZ5-16 ALL BB6 H H H
IZ5-17 NH2 BB6 H H H
IZ5-18 CBM BB6 H H H
IZ5-19 COM BB6 H H H
IZ5-20 COE BB6 H H H
IZ5-21 CBA BB6 H H H
IZ5-22 HYE BB6 H H H
IZ5-23 Me BB19 H H H
IZ5-24 Et BB19 H H H
IZ5-25 PH BB19 H H H
IZ5-26 Bu BB19 H H H
IZ5-27 TBu BB19 H H H
IZ5-28 Hex BB19 H H H
IZ5-29 Oct BB19 H H H
IZ5-30 2EH BB19 H H H
IZ5-31 CHM BB19 H H H
IZ5-32 CH BB19 H H H
IZ5-33 BZ BB19 H H H
IZ5-34 NPR BB19 H H H
IZ5-35 IPR BB19 H H H
IZ5-36 IBu BB19 H H H
IZ5-37 EOE BB19 H H H
IZ5-38 ALL BB19 H H H
IZ5-39 NH2 BB19 H H H
IZ5-40 CBM BB19 H H H
[ Table 2Z5]
TABLE 2Z5
RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5
IZ5-41 COM BB19 H H H
IZ5-42 COE BB19 H H H
IZ5-43 CBA BB19 H H H
IZ5-44 HYE BB19 H H H
IZ5-45 BZ BB2 H H H
IZ5-46 CHM BB3 H H H
IZ5-47 ALL BB4 H H H
IZ5-48 CBM BB5 H H H
IZ5-49 Me BB7 H H H
IZ5-50 NH2 BB8 H H H
IZ5-51 2EH BB9 H H H
IZ5-52 Et BB10 H H H
IZ5-53 IPR BB11 H H H
IZ5-54 COM BB12 H H H
IZ5-55 CBA BB13 H H H
IZ5-56 HYE BB14 H H H
IZ5-57 Bu BB15 H H H
IZ5-58 Hex BB16 H H H
IZ5-59 EOE BB17 H H H
IZ5-60 CH BB18 H H H
IZ5-61 PH BB20 H H H
IZ5-62 COE BB21 H H H
IZ5-63 TBu BB22 H H H
IZ5-64 Oct BB23 H H H
IZ5-65 IBu BB24 H H H
IZ5-66 NPR BB25 H H H
IZ5-67 BZ BB26 H H H
IZ5-68 CHM BB27 H H H
IZ5-69 ALL BB28 H H H
IZ5-70 CBM BB29 H H H
IZ5-71 Me BB30 H H H
IZ5-72 NH2 BB31 H H H
IZ5-73 2EH BB32 H H H
IZ5-74 Et BB33 H H H
IZ5-75 IPR BB34 H H H
IZ5-76 COM BB35 H H H
IZ5-77 CBA BB36 H H H
IZ5-78 HYE BB37 H H H
IZ5-79 Bu BB38 H H H
IZ5-80 Hex BB39 H H H
[ Table 3Z5]
TABLE 3Z5
RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5
IZ5-81 EOE BB40 H H H
IZ5-82 CH BB41 H H H
IZ5-83 PH BB42 H H H
IZ5-84 COE BB43 H H H
IZ5-85 TBu BB44 H H H
IZ5-86 Oct BB45 H H H
IZ5-87 IBu BB46 H H H
IZ5-88 NPR BB47 H H H
IZ5-89 BZ BB48 H H H
IZ5-90 CHM BB49 H H H
IZ5-91 ALL BB50 H H H
IZ5-92 CBM BB51 H H H
IZ5-93 Me BB52 H H H
IZ5-94 NH2 BB53 H H H
IZ5-95 2EH BB54 H H H
IZ5-96 Et BB55 H H H
IZ5-97 IPR BB56 H H H
IZ5-98 COM BB57 H H H
IZ5-99 CBA BB58 H H H
IZ5-100 HYE BB59 H H H
IZ5-101 PH BB60 H H H
IZ5-102 Et BB2 H Et Et
IZ5-103 IPR BB3 H NPR NPR
IZ5-104 COM BB4 H HYE HYE
IZ5-105 CBA BB5 H PH PH
IZ5-106 HYE BB6 H Me Me
IZ5-107 Bu BB7 H ALL ALL
IZ5-108 PH BB8 H 2EH 2EH
IZ5-109 EOE BB9 H CH CH
IZ5-110 BZ BB10 H BZ H
IZ5-111 CHM BB11 Me Me Me
IZ5-112 ALL BB12 H COM COM
IZ5-113 CBM BB13 H NPR NPR
IZ5-114 Me BB14 H IBu IBu
IZ5-115 NH2 BB15 H Oct Oct
IZ5-116 2EH BB16 H COE COE
IZ5-117 Et BB17 H HYE HYE
IZ5-118 IPR BB18 H EOE EOE
IZ5-119 COM BB19 Me Me Me
IZ5-120 CBA BB20 H Hex Hex
[ Table 4Z5]
TABLE 4Z5
RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5
IZ5-121 HYE BB21 H IPR IPR
IZ5-122 Bu BB22 H NH2 NH2
IZ5-123 Hex BB23 H Et Et
IZ5-124 EOE BB24 H BZ BZ
IZ5-125 CH BB25 H Me Me
IZ5-126 PH BB26 H CBA CBA
IZ5-127 COE BB27 H BZ H
IZ5-128 TBu BB28 H CHM CHM
IZ5-129 Oct BB29 H TBu TBu
IZ5-130 IBu BB30 H PH PH
IZ5-131 NPR BB31 H Bu Bu
IZ5-132 BZ BB32 Et CH CH
IZ5-133 CHM BB33 H ALL ALL
IZ5-134 ALL BB34 H CBM CBM
IZ5-135 CBM BB35 H CH CH
IZ5-136 Me BB36 H 2EH 2EH
IZ5-137 NH2 BB37 H COM COM
IZ5-138 2EH BB38 H NPR NPR
IZ5-139 Et BB39 H IBu IBu
IZ5-140 IPR BB40 H Oct Oct
IZ5-141 COM BB41 H COE COE
IZ5-142 CBA BB42 H HYE HYE
IZ5-143 HYE BB43 H EOE EOE
IZ5-144 Bu BB44 Me Me Me
IZ5-145 Hex BB45 H Hex Hex
IZ5-146 EOE BB46 H IPR IPR
IZ5-147 CH BB47 H NH2 NH2
IZ5-148 PH BB48 H Et Et
IZ5-149 COE BB49 H BZ BZ
IZ5-150 TBu BB50 H Me Me
IZ5-151 Oct BB51 H CBA CBA
IZ5-152 IBu BB52 H BZ H
IZ5-153 NPR BB53 H CHM CHM
IZ5-154 BZ BB54 H TBu TBu
IZ5-155 CHM BB55 H PH PH
IZ5-156 ALL BB56 H Bu Bu
IZ5-157 CBM BB57 Et CH CH
IZ5-158 Me BB58 H ALL ALL
IZ5-159 NH2 BB59 H CBM CBM
IZ5-160 2EH BB60 H CH CH
[ Table 5Z5]
TABLE 5Z5
RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5
IZ5-161 ALL BB2 SOT H H
IZ5-162 CBM BB3 SNH H H
IZ5-163 Me BB4 TBu H H
IZ5-164 NH2 BB5 SN2 H H
IZ5-165 2EH BB6 CNM H H
IZ5-166 Et BB7 Hex H H
IZ5-167 IPR BB8 CN2 H H
IZ5-168 COM BB9 NPH H H
IZ5-169 CBA BB10 Oct H H
IZ5-170 HYE BB11 NOT H H
IZ5-171 Bu BB12 NCO H H
IZ5-172 Hex BB13 H 2EH H
IZ5-173 EOE BB14 H H F
IZ5-174 CH BB15 H Cl H
IZ5-175 PH BB16 H H CHM
IZ5-176 COE BB17 H Br H
IZ5-177 IBu BB18 H H CN
IZ5-178 NPR BB19 H CH H
IZ5-179 BZ BB20 H H NO2
IZ5-180 CHM BB21 H SUA H
IZ5-181 ALL BB22 H H PH
IZ5-182 CBM BB23 H CBA H
IZ5-183 Me BB24 H H CHO
IZ5-184 NH2 BB25 H BZ BZ
IZ5-185 2EH BB26 H H OCH
IZ5-186 Et BB27 H NPR H
IZ5-187 IPR BB28 H H OH
IZ5-188 COM BB29 H IPR H
IZ5-189 CBA BB30 H H SFM
IZ5-190 HYE BB31 H IBu H
IZ5-191 Bu BB32 H H CBM
IZ5-192 Hex BB33 H EOE H
IZ5-193 EOE BB34 H H NH2
IZ5-194 CH BB35 H ALL H
IZ5-195 PH BB36 H H NCH
IZ5-196 COE BB37 H HYE H
IZ5-197 TBu BB38 2EH H H
IZ5-198 Oct BB39 F H H
IZ5-199 IBu BB40 Cl H H
IZ5-200 NPR BB41 CHM H H
[ Table 6Z5]
TABLE 6Z5
RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5
IZ5-201 BZ BB42 Br H H
IZ5-202 CHM BB43 CN H H
IZ5-203 ALL BB44 CH H H
IZ5-204 CBM BB45 NO2 H H
IZ5-205 Me BB46 SUA H H
IZ5-206 NH2 BB47 PH H H
IZ5-207 2EH BB48 CBA H H
IZ5-208 Et BB49 CHO H H
IZ5-209 IPR BB50 BZ H H
IZ5-210 COM BB51 OCH H H
IZ5-211 CBA BB52 NPR H H
IZ5-212 HYE BB53 OH H H
IZ5-213 Bu BB54 IPR H H
IZ5-214 Hex BB55 SFM H H
IZ5-215 EOE BB56 IBu H H
IZ5-216 CH BB57 CBM H H
IZ5-217 PH BB58 EOE H H
IZ5-218 COE BB59 NH2 H H
IZ5-219 TBu BB60 ALL H H
IZ5-220 Oct BB2 NCH H H
IZ5-221 IBu BB3 HYE H H
IZ5-222 NPR BB4 H Me H
IZ5-223 BZ BB5 H H COM
IZ5-224 CHM BB6 H COE H
IZ5-225 ALL BB7 H H Et
IZ5-226 CBM BB8 H OCM H
IZ5-227 Me BB9 H H OME
IZ5-228 NH2 BB10 H Bu H
IZ5-229 2EH BB11 H H SOT
IZ5-230 Et BB12 H SNH H
IZ5-231 IPR BB13 H H TBu
IZ5-232 COM BB14 H SN2 H
IZ5-233 CBA BB15 H H CNM
IZ5-234 HYE BB16 H Hex H
IZ5-235 Bu BB17 H H CN2
IZ5-236 Hex BB18 H NPH H
IZ5-237 EOE BB19 H H Oct
IZ5-238 CH BB20 H NOT H
IZ5-239 PH BB21 H H NCO
IZ5-240 COE BB22 Me H H
[ Table 7Z5]
TABLE 7Z5
RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5
IZ5-241 TBu BB23 COM H H
IZ5-242 Oct BB24 COE H H
IZ5-243 IBu BB25 Et H H
IZ5-244 NPR BB26 OCM H H
IZ5-245 BZ BB27 OME H H
IZ5-246 CHM BB28 Bu H H
IZ5-247 Me BB8 H H H
[ Table 10Z5]
TABLE 10Z5
RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5 RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5
IZ5-248 NA1 BB6 H H H IZ5-288 Hex BB11 H H H
IZ5-249 HHk8 BB6 H H H IZ5-289 Oct BB11 H H H
IZ5-250 NA2 BB6 H H H IZ5-290 2EH BB11 H H H
IZ5-251 HHk7 BB6 H H H IZ5-291 CHM BB11 H H H
IZ5-252 HH37 BB6 H H H IZ5-292 CH BB11 H H H
IZ5-253 HHk6 BB6 H H H IZ5-293 BZ BB11 H H H
IZ5-254 NA3 BB6 H H H IZ5-294 EOE BB11 H H H
IZ5-255 HHJ2 BB6 H H H IZ5-295 ALL BB11 H H H
IZ5-256 HHk11 BB6 H H H IZ5-296 NH2 BB11 H H H
IZ5-257 Et BB8 H H H IZ5-297 CBM BB11 H H H
IZ5-258 PH BB8 H H H IZ5-298 COM BB11 H H H
IZ5-259 Bu BB8 H H H IZ5-299 COE BB11 H H H
IZ5-260 TBu BB8 H H H IZ5-300 CBA BB11 H H H
IZ5-261 Hex BB8 H H H IZ5-301 HYE BB11 H H H
IZ5-262 Oct BB8 H H H IZ5-302 NA1 BB11 H H H
IZ5-263 2EH BB8 H H H IZ5-303 HHk8 BB11 H H H
IZ5-264 CHM BB8 H H H IZ5-304 NA2 BB11 H H H
IZ5-265 CH BB8 H H H IZ5-305 HHk7 BB11 H H H
IZ5-266 BZ BB8 H H H IZ5-306 HH37 BB11 H H H
IZ5-267 EOE BB8 H H H IZ5-307 HHk6 BB11 H H H
IZ5-268 ALL BB8 H H H IZ5-308 NA3 BB11 H H H
IZ5-269 CBM BB8 H H H IZ5-309 HHJ2 BB11 H H H
IZ5-270 COM BB8 H H H IZ5-310 HHk11 BB11 H H H
IZ5-271 COE BB8 H H H IZ5-311 Me BB14 H H H
IZ5-272 CBA BB8 H H H IZ5-312 Et BB14 H H H
IZ5-273 HYE BB8 H H H IZ5-313 PH BB14 H H H
IZ5-274 NA1 BB8 H H H IZ5-314 Bu BB14 H H H
IZ5-275 HHk8 BB8 H H H IZ5-315 TBu BB14 H H H
IZ5-276 NA2 BB8 H H H IZ5-316 Hex BB14 H H H
IZ5-277 HHk7 BB8 H H H IZ5-317 Oct BB14 H H H
IZ5-278 HH37 BB8 H H H IZ5-318 2EH BB14 H H H
IZ5-279 HHk6 BB8 H H H IZ5-319 CHM BB14 H H H
IZ5-280 NA3 BB8 H H H IZ5-320 CH BB14 H H H
IZ5-281 HHJ2 BB8 H H H IZ5-321 BZ BB14 H H H
IZ5-282 HHk11 BB8 H H H IZ5-322 EOE BB14 H H H
IZ5-283 Me BB11 H H H IZ5-323 ALL BB14 H H H
IZ5-284 Et BB11 H H H IZ5-324 NH2 BB14 H H H
IZ5-285 PH BB11 H H H IZ5-325 CBM BB14 H H H
IZ5-286 Bu BB11 H H H IZ5-326 COM BB14 H H H
IZ5-287 TBu BB11 H H H IZ5-327 COE BB14 H H H
[ Table 11Z5]
TABLE 11Z5
RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5 RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5
IZ5-328 CBA BB14 H H H IZ5-368 HHk7 BB37 H H H
IZ5-329 NA1 BB14 H H H IZ5-369 HH37 BB37 H H H
IZ5-330 HHk8 BB14 H H H IZ5-370 HHk6 BB37 H H H
IZ5-331 NA2 BB14 H H H IZ5-371 NA3 BB37 H H H
IZ5-332 HHk7 BB14 H H H IZ5-372 HHJ2 BB37 H H H
IZ5-333 HH37 BB14 H H H IZ5-373 HHk11 BB37 H H H
IZ5-334 HHk6 BB14 H H H IZ5-374 Me BB58 H H H
IZ5-335 NA3 BB14 H H H IZ5-375 Et BB58 H H H
IZ5-336 HHJ2 BB14 H H H IZ5-376 PH BB58 H H H
IZ5-337 HHk11 BB14 H H H IZ5-377 Bu BB58 H H H
IZ5-338 NA1 BB19 H H H IZ5-378 TBu BB58 H H H
IZ5-339 HHk8 BB19 H H H IZ5-379 Hex BB58 H H H
IZ5-340 NA2 BB19 H H H IZ5-380 Oct BB58 H H H
IZ5-341 HHk7 BB19 H H H IZ5-381 2EH BB58 H H H
IZ5-342 HH37 BB19 H H H IZ5-382 CHM BB58 H H H
IZ5-343 HHk6 BB19 H H H IZ5-383 CH BB58 H H H
IZ5-344 NA3 BB19 H H H IZ5-384 BZ BB58 H H H
IZ5-345 HHJ2 BB19 H H H IZ5-385 EOE BB58 H H H
IZ5-346 HHk11 BB19 H H H IZ5-386 ALL BB58 H H H
IZ5-347 Me BB37 H H H IZ5-387 NH2 BB58 H H H
IZ5-348 Et BB37 H H H IZ5-388 CBM BB58 H H H
IZ5-349 PH BB37 H H H IZ5-389 COM BB58 H H H
IZ5-350 Bu BB37 H H H IZ5-390 COE BB58 H H H
IZ5-351 TBu BB37 H H H IZ5-391 HYE BB58 H H H
IZ5-352 Hex BB37 H H H IZ5-392 NA1 BB58 H H H
IZ5-353 Oct BB37 H H H IZ5-393 HHk8 BB58 H H H
IZ5-354 2EH BB37 H H H IZ5-394 NA2 BB58 H H H
IZ5-355 CHM BB37 H H H IZ5-395 HHk7 BB58 H H H
IZ5-356 CH BB37 H H H IZ5-396 HH37 BB58 H H H
IZ5-357 BZ BB37 H H H IZ5-397 HHk6 BB58 H H H
IZ5-358 EOE BB37 H H H IZ5-398 NA3 BB58 H H H
IZ5-359 ALL BB37 H H H IZ5-399 HHJ2 BB58 H H H
IZ5-360 NH2 BB37 H H H IZ5-400 HHk11 BB58 H H H
IZ5-361 CBM BB37 H H H IZ5-401 Me BBJ2 H H H
IZ5-362 COM BB37 H H H IZ5-402 Et BBJ2 H H H
IZ5-363 COE BB37 H H H IZ5-403 PH BBJ2 H H H
IZ5-364 CBA BB37 H H H IZ5-404 Bu BBJ2 H H H
IZ5-365 NA1 BB37 H H H IZ5-405 TBu BBJ2 H H H
IZ5-366 HHk8 BB37 H H H IZ5-406 Hex BBJ2 H H H
IZ5-367 NA2 BB37 H H H IZ5-407 Oct BBJ2 H H H
[ Table 12Z5] Table 12Z5
RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5 RN1Z5 Ba1Z5Ba2Z5 R1Z5 R6Z5 R7Z5
IZ5-408 2EH BBJ2 H H H IZ5-448 NA1 BBO8 H H H
IZ5-409 CHM BBJ2 H H H IZ5-449 HHk8 BBO8 H H H
IZ5-410 CH BBJ2 H H H IZ5-450 NA2 BBO8 H H H
IZ5-411 BZ BBJ2 H H H IZ5-451 HHk7 BBO8 H H H
IZ5-412 EOE BBJ2 H H H IZ5-452 HH37 BBO8 H H H
IZ5-413 ALL BBJ2 H H H IZ5-453 HHk6 BBO8 H H H
IZ5-414 NH2 BBJ2 H H H IZ5-454 NA3 BBO8 H H H
IZ5-415 CBM BBJ2 H H H IZ5-455 HHJ2 BBO8 H H H
IZ5-416 COM BBJ2 H H H IZ5-456 HHk11 BBO8 H H H
IZ5-417 COE BBJ2 H H H IZ5-457 Me BBO10 H H H
IZ5-418 CBA BBJ2 H H H IZ5-458 Et BBO10 H H H
IZ5-419 HYE BBJ2 H H H IZ5-459 PH BBO10 H H H
IZ5-420 NA1 BBJ2 H H H IZ5-460 Bu BBO10 H H H
IZ5-421 HHk8 BBJ2 H H H IZ5-461 TBu BBO10 H H H
IZ5-422 NA2 BBJ2 H H H IZ5-462 Hex BBO10 H H H
IZ5-423 HHk7 BBJ2 H H H IZ5-463 Oct BBO10 H H H
IZ5-424 HH37 BBJ2 H H H IZ5-464 2EH BBO10 H H H
IZ5-425 HHk6 BBJ2 H H H IZ5-465 CHM BBO10 H H H
IZ5-426 NA3 BBJ2 H H H IZ5-466 CH BBO10 H H H
IZ5-427 HHJ2 BBJ2 H H H IZ5-467 BZ BBO10 H H H
IZ5-428 HHk11 BBJ2 H H H IZ5-468 EOE BBO10 H H H
IZ5-429 Me BBO8 H H H IZ5-469 ALL BBO10 H H H
IZ5-430 Et BBO8 H H H IZ5-470 NH2 BBO10 H H H
IZ5-431 PH BBO8 H H H IZ5-471 CBM BBO10 H H H
IZ5-432 Bu BBO8 H H H IZ5-472 COM BBO10 H H H
IZ5-433 TBu BBO8 H H H IZ5-473 COE BBO10 H H H
IZ5-434 Hex BBO8 H H H IZ5-474 CBA BBO10 H H H
IZ5-435 Oct BBO8 H H H IZ5-475 HYE BBO10 H H H
IZ5-436 2EH BBO8 H H H IZ5-476 NA1 BBO10 H H H
IZ5-437 CHM BBO8 H H H IZ5-477 HHk8 BBO10 H H H
IZ5-438 CH BBO8 H H H IZ5-478 NA2 BBO10 H H H
IZ5-439 BZ BBO8 H H H IZ5-479 HHk7 BBO10 H H H
IZ5-440 EOE BBO8 H H H IZ5-480 HH37 BBO10 H H H
IZ5-441 ALL BBO8 H H H IZ5-481 HHk6 BBO10 H H H
IZ5-442 NH2 BBO8 H H H IZ5-482 NA3 BBO10 H H H
IZ5-443 CBM BBO8 H H H IZ5-483 HHJ2 BBO10 H H H
IZ5-444 COM BBO8 H H H IZ5-484 HHk11 BBO10 H H H
IZ5-445 COE BBO8 H H H IZ5-485 HH22 BB2 H H H
IZ5-446 CBA BBO8 H H H IZ5-486 HH40 BB3 H H H
IZ5-447 HYE BBO8 H H H IZ5-487 HHk7 BB4 H H H
[ Table 13Z5]
TABLE 13Z5
Figure BDA0003121580680003161
For example, the compound IZ5-1 is a compound represented by the following formula (IZ 5-1).
Figure BDA0003121580680003162
The compound IZ5-1 to the compound IZ5-160 and the compound IZ5-247 to the compound IZ5-542 are preferable, the compound IZ5-1 to the compound IZ5-160 and the compound IZ5-247 to the compound IZ5-484 are more preferable, the compound IZ5-1 to the compound IZ5-160 are still more preferable, the compound IZ5-1 to the compound IZ5-101 are still more preferable, and the compound IZ5-1 to the compound IZ5-44 are particularly preferable.
Specific examples of the compound IZ5 include compounds represented by table 1Z5, table 2Z5, table 3Z5, table 4Z5, table 5Z5, table 6Z5, table 7Z5, and tables 10Z5 to 13Z5, in which 1 to 3 hydrogen atoms are replaced by-SO3M or-CO2M is substituted. For example, compounds having 1 to 3 sulfo groups bonded to the compound IZ5-1 of Table 1Z5 are represented by the following structures. Wherein in (SO)3H) Represents a compound in which any hydrogen atom in compound IZ5-1 of Table 1Z5 is substituted.
Figure BDA0003121580680003171
Preferably, 1 to 3-SO groups are bonded to the compound IZ5-1 to the compound IZ5-160 and the compound IZ5-247 to the compound IZ5-5423M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ5-1 to the compound IZ5-160 and the compound IZ5-247 to the compound IZ5-4843M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ5-1 to the compound IZ5-1603M or-CO2M, more preferably 1 to 3-SO groups are bonded to the compound IZ5-1 to the compound IZ5-1013M or-CO2M, particularly preferably 1 to 3-SO groups are bonded to the compound IZ5-1 to the compound IZ5-443M or-CO2M, or a salt thereof.
Figure BDA0003121580680003172
As the compound (IZ5), the following compounds are preferable:
In the formula (IZ5), RN1Z5is-CO-R102Z5、-COO-R101Z5、-CON(R102Z5)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R1Z5Is a hydrogen atom and may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,R2Z5~R5Z5Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z5)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M,R2Z5~R5Z5At least one of which is a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z5)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M,
R6Z5And R7Z5Independently of one another, a hydrogen atom, may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,
R102Z5Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R101Z5May have a structure selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 20 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
More preferred are the following compounds:
RN1Z5is-CO-R102Z5、-CON(R102Z5)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R1Z5Is a hydrogen atom, R2Z5~R5Z5Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z5)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M,R2Z5~R5Z5At least one of which is a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z5)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M,R6Z5And R7Z5Are the same group, are hydrogen atoms, or may have a structure selected from the group consisting of3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R102Z5Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R101Z5May have a structure selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
RN1Z5is-CO-R102Z5、-CON(R102Z5)2Or may have a structure selected from the group consisting of-SO 3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1Z5is a hydrogen atom, R2Z5~R5Z5Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z5)2Nitro, trifluoromethyl, -O-R102Z5、-SO3M or-CO2M,R2Z5~R5Z5At least one of which is a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z5)2Nitro, trifluoromethyl, -O-R102Z5、-SO3M or-CO2M,
R6Z5And R7Z5The same group is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms,
R102Z5is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R101Z5May have a structure selected from the group consisting of-SO3M and-CO2And M is a compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms and M is a hydrogen atom or an alkali metal atom.
For compound IZ5, R1Z5In the case of a hydrogen atom, the compound represented by the formula (pt1Z5) (hereinafter, may be referred to as a phthalonitrile compound) may be produced by reacting a compound represented by the formula (pt2Z5) (hereinafter, may be referred to as an alkoxide compound), and then further reacting the compound represented by the formula (pt3Z5) and the compound represented by the formula (pt4Z5) in the presence of an acid. In addition, R1Z5When not a hydrogen atom, the compound is further reacted with a compound represented by the formula (pt5Z5) to produce a compound IZ 5.
Figure BDA0003121580680003201
In [ formula (pt1Z5), formula (pt2Z5), formula (pt3Z5), formula (pt4Z5), formula (pt5Z5) and formula (IZ5), RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5And R7Z5The same meanings as described above are indicated. R14Z5Represents an alkyl group having 1 to 20 carbon atoms. M1Z5Represents an alkali metal atom. LG represents halogenAn elemental atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group.]
As R14Z5Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z5Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z5 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z5 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z5, and the compound pt4Z5 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; 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 acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound.
The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z5 used, relative to R1Z5The amount of the compound IZ51 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
When the compound pt5Z5 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1Z5The amount of the compound IZ51 is usually 1 to 10 mol based on the hydrogen atomThe amount of the organic solvent is preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
The reaction of compound pt5Z5 can generally be carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1Z5The amount of the compound IZ 51 is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z5 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound IZ5 having no sulfo group or-SO3M2In the case of (3), the compound IZ5 can be reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to introduce a sulfo group or-SO3M22。M22Represents an alkali metal atom. As M22Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
With respect to SO in oleum3The amount of (b) is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and still more preferably 5 to 25 mol based on 51 mol of the compound IZ. The amount of sulfuric acid used in the oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on 51 moles of the compound IZ. The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on 51 moles of the compound IZ.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound IZ5 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is filtered to extract the compound IZ 5. The residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
< Compound IZ6 >)
Compound IZ6 is represented by formula (IZ 6).
Figure BDA0003121580680003231
Figure BDA0003121580680003232
Figure BDA0003121580680003233
[ in the formula (IZ6), D represents a structure having an isoindoline skeleton. Z represents-SO3 -or-CO2 -。Ac+Represents a metal cation having a valence of c. a represents an integer of 1 to 10. b represents an integer of 1 or more. c represents an integer of 2 to 10. d represents an integer of 1 or more.
D. Z, a or Ac+When there are a plurality of them, they may be the same or different. The formula (I 'Z6) and the formula (I' Z6) respectively represent partial structures of the formula (IZ6), D, Z, Ac+A, b, c and d represent the same meanings as the corresponding symbols in formula (IZ 6). The partial structure represented by the formula (I' Z6) has the same negative valence as the partial structure represented by the formula (I "Z6) has the same positive valence in absolute value. ]
The integer represented by a is 1 to 10, preferably 1 to 8, more preferably 1 to 6, and further preferably 1 to 4. The integer represented by b is 1 or more, preferably 1 to 10, and more preferably 1 to 8. The integer represented by c is 2 to 10, preferably 2 to 8, more preferably 2 to 6, and further preferably 2 to 4. d represents an integer of 1 or more, preferably 1 to 10, more preferably 1 to 8. Z is preferably-CO2 -
Ac+Represents a metal cation having a valence of 2 or more. As the metal cation having a valence of 2 or more,
examples thereof include:the cation of a metal of groups 2 to 15 of the periodic Table of the elements is preferably Mg2+、Ca2+、Sr2 +、Ba2+、Cd2+、Ni2+、Zn2+、Cu2+、Hg2+、Fe2+、Co2+、Sn2+、Pb2+And Mn2+An isovalent 2 metal cation; al (Al)3+、Fe3+And Cr3+An equivalent 3 valent metal cation; sn (tin)4+And Mn4+The metal cation having a valence of 4, more preferably Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Cu2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+And Mn4+More preferably, Mg is mentioned2+、Ca2 +、Sr2+、Ba2+、Zn2+、Cu2+、Fe2+、Mn2+、Al3+、Fe3+、Cr3+And Mn4+
The compound represented by the formula (IZ6) is preferably a compound represented by the formula (IZ6-A) (hereinafter, may be referred to as a compound IZ 6-A.).
Figure BDA0003121580680003241
Figure BDA0003121580680003242
Figure BDA0003121580680003243
[ in the formula (IZ6-A), Ac+B, c and d are as defined above.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Independently of one another, represents a hydrogen atom, -CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
R2AZ6And R 3AZ6、R3AZ6And R4AZ6、R4AZ6And R5AZ6、RAA1Z6And RAA2Z6And R12AZ6And R13AZ6Each of which may be bonded to each other to form a ring. R101AZ6Independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R102AZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom.
The formula (IZ6-A ') and the formula (IZ 6-A') each represent a partial structure of the formula (IZ6-A), Ac+、b、c、d、R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Represents the same meaning as the corresponding symbol in the formula (IZ 6-A).
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6、R102AZ6M, c or Ac+When there are plural, they may or may not be the sameThe same is true.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6Satisfies at least 1 of (ra-i) to (ra-iii), R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(ra-i)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is-SO3 -or-CO2 -
(ra-ii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is-CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6or-OCON (R)102AZ6)2R is a hydrogen atom101AZ6And R102AZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(ra-iii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO 2 -The heterocyclic group of (1). Wherein the hydrocarbon group and the heterocyclic group may have-SO3 -or-CO2 -And (ii) an additional substituent.
a represents the same meaning as the symbol in the formula (IZ 6). When a plurality of a exist, they may be the same or different.
The partial structure represented by the formula (IZ 6-A') has the same negative valence as the partial structure represented by the formula (IZ6-A ") has the same positive valence in absolute value. The wavy line indicates the E-body or the Z-body. ]
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The number of carbon atoms of the hydrocarbon group is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, and particularly preferably 1 to 10.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; an isopropyl group,Branched alkyl groups such as isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and further preferably 1 to 15. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, and still more preferably 1 to 5 carbon atoms is particularly preferable.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, and, Cycloalkyl groups such as 2,2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, and cyclooctenyl; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, particularly preferred is Is cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a mesityl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a, Aromatic hydrocarbon groups such as 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracyl, pyrenyl and the like; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6A group represented byExamples of the group formed by combining the hydrocarbon groups (e.g., the chain hydrocarbon group and the alicyclic hydrocarbon group) include an alkyl group in which 1 or more alicyclic hydrocarbon groups are bonded, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, and an adamantylmethyl group.
The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group represented may have a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
Figure BDA0003121580680003291
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl;
a formyl group;
a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
Figure BDA0003121580680003301
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
Figure BDA0003121580680003302
Figure BDA0003121580680003311
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formula);
Figure BDA0003121580680003321
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, N-phenylmethylsulfamoyl, and the like, and groups represented by the following chemical formulae);
Figure BDA0003121580680003331
Figure BDA0003121580680003341
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
Figure BDA0003121580680003342
Figure BDA0003121580680003351
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is alkali goldGenus, preferably lithium, sodium, potassium); a nitro group; a cyano group;
a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
Figure BDA0003121580680003352
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
Figure BDA0003121580680003361
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
Figure BDA0003121580680003371
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, and a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3and-CO-S-CH2-CH2-CH2-CH3An alkylthio carbonyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), -CO-S-C 6H5An arylthiocarbonyl group having 6 to 20 carbon atoms;
a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
Figure BDA0003121580680003381
-NRCONR represented by the following chemical formula2(wherein R represents a hydrogen atom and the number of carbon atoms is 1A hydrocarbyl group of up to 20 (for example, a hydrocarbyl group having 1 to 20 carbon atoms among the above-mentioned hydrocarbyl groups), or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like), wherein R's may be the same or different from each other, and may be bonded to each other to form a ring);
Figure BDA0003121580680003391
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
Figure BDA0003121580680003401
A group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
Figure BDA0003121580680003411
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R represents a hydrogen atom and the number of carbon atoms is 1A hydrocarbyl group of up to 20 (for example, a hydrocarbyl group having 1 to 20 carbon atoms among the above-mentioned hydrocarbyl groups), or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like), wherein R's may be the same or different from each other, and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR3(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring); -SO 3 -;-CO2 -(ii) a And so on.
Examples of the substituent having a valence of 2 include an oxo group, a thioxo 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. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom; -CO 2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom);
-SO3m (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group; -SO3 -;-CO2 -
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
An amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a hydroxyl group; fluorine atom, chlorine atom, bromine atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom);
-SO3m (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group;
a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms;
a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group; -SO 3 -;-CO2 -
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The substituted hydrocarbon group having 1 to 40 carbon atoms includes a substituted hydrocarbon group having 1 to 40 carbon atoms having a valence of 1 or 2; preferably, the hydrocarbon-based compound includes a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, or a group having 4 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which are a combination of the hydrocarbon groups;
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups, and the group has 4 to 20 carbon atoms having a substituent of group s 1;
particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 4 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The heterocyclic group represented by (a) may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include monocyclic saturated heterocyclic rings such as aziridine, azetidine, pyrrolidine, piperidine, and piperazine; five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole; a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine; a fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane; bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone; five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran;
fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole, chroman and isochroman; fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include a five-membered ring system saturated heterocyclic ring such as dithiolane; saturated heterocyclic rings of six-membered ring systems such as thiacyclohexane, 1, 3-dithiane, 2-methyl-1, 3-dithiane and the like; a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran); fused bicyclic heterocycles such as benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include:
monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone; a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole);
fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
Figure BDA0003121580680003451
The above heterocyclic group may be R1AZ6~R5AZ62 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1AZ6~R5AZ6The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
Figure BDA0003121580680003452
The bonding position of the heterocycle is a portion where any hydrogen atom contained in each ring is removed.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The heterocyclic group represented may have a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. In addition, in the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom.
Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The heterocyclic group having a substituent represented by the formula (i) includes a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s 2.
The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Of (a) is-CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, -SO3M、-CO2M is explained. Examples of-CO-R hereinafter102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Preferably in the range corresponding to R101AZ6、R102AZ6In which a substituent of group s2, in particular-SO3 -、-CO2 -And the like.
as-CO-R102AZ6Examples thereof include a formyl group; a carbonyl group (having 2 to 41 carbon atoms when the carbonyl group is an acyl group), wherein the carbonyl group is a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, a (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, a undecanoyl group, a dodecanoyl group, a heneicosanoyl group, a benzoyl group, or the group represented by the above chemical formula (i) and the like), and the carbonyl group corresponding to-CO-R-in the compounds represented by Table 1Z6 to Table 4Z6102AZ6Preferable examples of the group(s) include a carbonyl group (more preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and compounds represented by tables 1Z6 to 4Z6 corresponding to-CO-R 102AZ6And the like.
as-COO-R101AZ6Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl, eicosyloxycarbonyl and the like, and a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an orthocarbon group bonded to a group represented by the above formula or the likeGroups derived from alkylsulfamoyl (preferably octylsulfamoyl) having 1 to 10 moles) and compounds shown in tables 1Z6 to 4Z6, which correspond to-COO-R102AZ6Preferred examples of the group (b) include oxycarbonyl groups to which a C1-10 hydrocarbon group or a derivative thereof is bonded and compounds represented by tables 1Z6 to 4Z6 corresponding to-COO-R102AZ6And the like.
as-OCO-R102AZ6Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy and the like, carbonyloxy (having 2 to 41 carbon atoms in the case where the carbonyloxy group is an acyloxy group), carbonyloxy having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) bonded to a group represented by the above formula) and the like, And the compounds shown in tables 1Z6 to 4Z6 correspond to-OCO-R 102AZ6The group (B) preferably includes a carbonyloxy group (more preferably 2 to 12 carbon atoms in the case where the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z6 to 4Z6 corresponding to-OCO-R102AZ6And the like.
as-COCO-R102Z6Examples thereof include methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) hexyloxalyl, heptyloxalyl, octyloxalyl, nonyloxalyl, decyloxyl, undecyloxalyl, dodecyloxalyl, eicosanoyl, cyclopentyloxalyl, cyclohexyloxalyl, phenyloxalyl, p-tolyloxalyl and the like, and a group represented by the above-mentioned chemical formulaAnd an oxalyl group to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded).
as-O-R102AZ6There may be mentioned a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 5-dimethylphenyloxy, 2, 6-dimethylphenyloxy, 3, 4-dimethylphenyloxy, 3, 5-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 3-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 4-di-yloxy, 2-di-methyl-1-phenylethoxy, 2, 4-di-methyl, and mixtures thereof, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, examples of the oxygen group include an oxygen group having a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like bonded thereto, such as a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the above chemical formula), and compounds shown in tables 1Z6 to 4Z6, which correspond to — O — R. 102AZ6Preferable examples of the group (b) include an oxy group to which a C1-10 hydrocarbon group or a derivative thereof is bonded, and compounds represented by tables 1Z6 to 4Z6 corresponding to-O-R102AZ6And the like.
as-SO2-R101AZ6Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl) hexylsulfonyl, heptylsulfonyl, ethylsulfonyl, pentylsulfonyl, ethylsulfonyl, 2-hexylsulfonyl, ethylsulfonyl, ethyl,Octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, eicosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group and the like, and sulfonyl groups in which a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) is bonded such as the group represented by the above chemical formula) and the compounds shown in tables 1Z6 to 4Z6 correspond to-SO2-R102AZ6Preferable examples of the group (b) include a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded and a group corresponding to-SO in the compounds represented by tables 1Z6 to 4Z6 2-R102AZ6And the like.
as-SO2N(R102AZ6)2Examples thereof include: a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl, N-phenylsulfamoyl, etc., and a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula, or a derivative thereof Sulfamoyl groups substituted with a raw group (e.g., a group derived from carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group)), and compounds represented by tables 1Z6 to 4Z6, which correspond to — SO2NH(R102AZ6X)(R102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above), etc.; n, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylamido Sulfonyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylaminosulfonyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 2 hydrocarbon groups having 1 to 40 (preferably 1 to 20) carbon atoms or derivative groups thereof (e.g., groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N, N-undecylmethylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylmethylsulfamoyl, N-phenylmethylsulfamoyl, N-diphenylsulfamoyl, and the like, and groups represented by the above chemical formulae), and sulfamoyl groups derived from compounds represented by tables 1Z6 to 4Z6, which correspond to-SO 2N(R102AZ6X)2(R102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above), and the like, and preferably include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds represented by tables 1Z6 to 4Z6, which correspond to-SO2N(R102AZ6)2And the like.
as-CON (R)102AZ6)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-octylcarbamoyl and N-nonylcarbamoyl, N-decylcarbamoyl, N-decadecadecylcarbamoylMonoalkylcarbamoyl, N-dodecylcarbamoyl, N-eicosylcarbamoyl, N-phenylcarbamoyl and the like, and carbamoyl groups represented by the above chemical formulae which are substituted with a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) or the like), and a compound represented by one of tables 1Z6 to 4Z6 corresponds to-CONH (R-CONH) 102AZ6X)(R102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above), etc.;
n, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-tert-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-diethylcarbamoyl group, N-diisopropylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-isobutylcarbamoyl group, N-di (s-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-di-N-butylcarbamoyl group, N, a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, an N, N-di (2-ethyl) hexylcarbamoyl group, an N, N-diheptylcarbamoyl group, an N, N-octylmethylcarbamoyl group, an N, N-dinonylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, an N, N-diphenylcarbamoyl group, etc., and a group represented by the above chemical formula, A carbamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and a compound represented by any one of tables 1Z6 to 4Z6 corresponding to-CON (R) 102AZ6X)2(R102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z6 to 4Z6 corresponding to-CON (R)102AZ6)2And the like.
as-N (R)102AZ6)2Examples thereof include: an amino group; a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom)), such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, an N-tert-butylamino group, an N-pentylamino group, an N-hexylamino group, an N- (2-ethyl) hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-undecylamino group, an N-dodecylamino group, an N-eicosylamino group, an N-phenylamino group, and the like, and a group represented by the above chemical formula, A group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) and the like) and a compound shown in tables 1Z6 to 4Z6 corresponding to-NH (R102AZ6X) (wherein, R 102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above), etc.;
n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-dipentylamino group, N-bis (1-ethylpropyl) amino group, N-dihexylamino group, N-bis (2-ethyl) hexylamino group, N-diheptylamino group, N-dioctylamino group, N, n-dinonylamino group, N-decylmethylamino group, N-undecylmethylamino group, N-dodecylmethylamino group, N-eicosylmethyl amino group, N-phenylmethylamino group, N-diphenylamino group, etc., and a group represented by the above chemical formula, etc., having 2 carbon atomsAmino groups substituted with 1 to 40 (preferably 1 to 20 carbon atoms) hydrocarbon groups or derivative groups thereof (for example, groups derived from carboxyl groups, sulfo groups, nitro groups, hydroxyl groups, halogens (preferably chlorine atoms), alkylsulfamoyl groups (preferably octylsulfamoyl groups) having 1 to 10 carbon atoms), and the like, and compounds shown in tables 1Z6 to 4Z6 corresponding to-N (R is 102AZ6X)2(wherein, R102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above), and the like, and preferably include an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and a group corresponding to-N (R) in the compounds shown in tables 1Z6 to 4Z6102AZ6)2And the like.
as-NHCO-R102AZ6Examples thereof include formylamino; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, examples of the carbonylamino group (the number of carbon atoms is 1 to 40 in the case where the carbonylamino group is an acylamino group), to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, a benzoylamino group and the like, and the compounds shown in tables 1Z6 to 4Z6 correspond to-NHCO-R. 102AZ6Preferable examples of the group (b) include a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded (in the case where the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10), and compounds represented by tables 1Z6 to 4Z6, wherein the compound corresponds to-NHCO-R102AZ6And the like.
as-NHCON (R)102AZ6)2Examples thereof include the groups listed above and the compounds shown in tables 1Z6 to 4Z6 which correspond to-NHCON (R)102AZ6)2And the like.
as-NHCOOR102AZ6Examples thereof include the groups listed above and the groups corresponding to-NHCOOR among the compounds shown in tables 1Z6 to 4Z6102AZ6And the like.
as-OCON (R)102AZ6)2Examples thereof include those corresponding to-OCON (R) in the above-mentioned groups and the compounds shown in tables 1Z6 to 4Z6102AZ6)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M in M is a hydrogen atom; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102AZ6、-COO-R102AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R102AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCON(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Preferably a hydrogen atom, -CO-R102AZ6、-COO-R101AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
As R101AZ6The hydrocarbon group having 1 to 40 carbon atoms which may have a substituent is preferable.
As R102AZ6Preferably, the hydrocarbon group has 1 to 40 carbon atoms and may have a substituent.
R2AZ6And R3AZ6、R3AZ6And R4AZ6And R4AZ6And R5AZ6The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 6). As R2AZ6And R3AZ6、R3AZ6And R4AZ6And R4AZ6And R5AZ6Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, and benzo [9,10 ] ene]Phenanthrene, pyrene,
Figure BDA0003121580680003541
Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide and butachlor, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, etc.); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,
Figure BDA0003121580680003542
Nitrogen-containing fused heterocycles and partial reductants thereof such as pyridine, phenanthroline and phenazine; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2AZ6And R3AZ6、R3AZ6And R4AZ6And R4AZ6And R5AZ6In the case of forming a ring, the ring may have a substituent. AsThe substituent includes1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3AZ6And R4AZ6In the case of forming a ring, R2AZ6And R5AZ6Independently of one another, hydrogen atoms, amino groups or hydroxyl groups are preferred.
R2AZ6And R3AZ6When a ring is formed, R is preferably4AZ6And R5AZ6Does not form a ring, more preferably R4AZ6And R5AZ6Is a hydrogen atom.
In addition, R4AZ6And R5AZ6When a ring is formed, R is preferably2AZ6And R3AZ6Does not form a ring, more preferably R2AZ6And R3AZ6Is a hydrogen atom.
RAA1Z6And RAA2Z6And R12AZ6And R13AZ6The ring formed is bonded to the exocyclic methylene (C ═ CH) group of the isoindoline skeleton of formula (IZ6)2) Is bonded to contain the exocyclic methylene (C ═ CH)2) In the form of structures within, R is listedAA1Z6And RAA2Z6And R12AZ6And R13AZ6Examples of the ring to be formed include structures in which a carbonyl group, an exocyclic methylene group and a carbonyl group are arranged in this order as shown in the following groups A and B. Represents a bond to the isoindoline backbone.
[ group A ]
Figure BDA0003121580680003561
[ group B ]
Figure BDA0003121580680003571
R104AZ6、R105AZ6、R106AZ6And R107AZ6Independently of one another, represents a hydrogen atom, -CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, cyano group, nitro group, -SO 3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
With respect to R104AZ6、R105AZ6、R106AZ6And R107AZ6Represented by-CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, -SO3M and-CO2M, may be exemplified by1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Represented by-CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, -SO3M and-CO2M is the same example.
As R104AZ6、R105AZ6、R106AZ6And R107AZ6The optionally substituted hydrocarbon group having 1 to 40 carbon atoms and the optionally substituted heterocyclic group are represented by1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or the heterocyclic group which may have a substituent are the same.
R104AZ6、R105AZ6、R106AZ6And R107AZ6The hydrocarbon group and the heterocyclic group having 1 to 40 carbon atoms may have a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
As R104AZ6、R105AZ6、R106AZ6And R107AZ6Preferably, R is1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same preferable example as in (1).
As R104AZ6、R105AZ6、R106AZ6And R107AZ6More preferably, the alkyl group has 1 to 10 carbon atoms and a hydrogen atom, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a (2-ethyl) hexyl group, a heptyl group, an octyl group, a nonyl group, a cyclohexyl group, and a phenyl group.
For the groups exemplified in group A and group B, the hydrogen atom bonded to the ring structure may be substituted with a substituent.
Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent.
Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
R1AZ6Is a hydrogen atom, R2AZ6、R3AZ6、R4AZ6And R5AZ6Independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N (R)102AZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102AZ6、-O-R102AZ6、-SO3M or-CO2M,
More preferably a hydrogen atom, a tert-butyl group or a nitro group.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6Preferably satisfies at least 1 of (raa-i) to (raa-iii), R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(raa-i)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is-SO3 -or-CO2 -
(raa-ii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is-CO-R102AZ6、-COO-R101AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2or-N (R)102AZ6)2R is a hydrogen atom101AZ6And R102AZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(raa-iii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO 3 -or-CO2 -The heterocyclic group of (1). The hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
Examples of the groups a and B include rings represented by the formulae (QQ1) to (QQ25) and the formulae (QQA1) to (QQA 36).
Figure BDA0003121580680003601
Figure BDA0003121580680003611
Figure BDA0003121580680003621
The compound represented by the formula (IZ6-A) is preferably a compound represented by the formula (IZ6-B) (hereinafter, may be referred to as a compound IZ 6-B.).
Figure BDA0003121580680003631
Figure BDA0003121580680003632
Figure BDA0003121580680003633
[ formula (IZ6-B) wherein Ac+B, c, d and the wavy line have the same meanings as described above. L is1represents-CO-or-SO2-。R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6Independently of one another, represents a hydrogen atom, -CO-R102BZ6、-COO-R101BZ6、-OCO-R102BZ6、-COCO-R102BZ6、-O-R102BZ6、-SO2-R101BZ6、-SO2N(R102BZ6)2、-CON(R102BZ6)2、-N(R102BZ6)2、-NHCO-R102BZ6、-NHCO-N(R102BZ6)2、-NHCOOR102BZ6、-OCON(R102BZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
R2BZ6And R3BZ6、R3BZ6And R4BZ6、R4BZ6And R5BZ6And R12BZ6And R13BZ6Each of which may be bonded to each other to form a ring.
R101BZ6Independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R102BZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
The formula (IZ6-B ') and the formula (IZ 6-B') each represent a partial structure of the formula (IZ6-B), Ac+、b、c、d、R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6And L1Represents the same meaning as the corresponding symbol in the formula (IZ 6-B).
M represents the same meaning as described above.
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6、R102BZ6、L1M, c or Ac+When there are a plurality of them, they may be the same or different.
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6Satisfies at least 1 of (rb-i) to (rb-iii), R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6Is provided withis-SO of3 -or-CO2 -The total number of (a) is a.
(rb-i)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is-SO3 -or-CO2 -
(rb-ii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is-CO-R102BZ6、-COO-R101BZ6、-OCO-R102BZ6、-COCO-R102BZ6、-O-R102BZ6、-SO2-R101BZ6、-SO2N(R102BZ6)2、-CON(R102BZ6)2、-N(R102BZ6)2、-NHCO-R102BZ6、-NHCO-N(R102BZ6)2、-NHCOOR102BZ6or-OCON (R)102BZ6)2R is a hydrogen atom101BZ6And R102BZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rb-iii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
a represents the same meaning as the symbol in the formula (IZ 6-A). When a plurality of a exist, they may be the same or different.
The partial structure represented by the formula (IZ6-B ') has the same negative valence as the partial structure represented by the formula (IZ 6-B') has the same positive valence in absolute value. ]
As R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6Examples thereof include the compounds with R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same example.
As R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6Preferred examples of (3) include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same preferred examples as those of (1).
As R 101BZ6Examples thereof include the compounds with R101AZ6The same example. As R101BZ6Preferred examples of (3) include101AZ6The same preferred examples as those of (1). As R102BZ6Examples thereof include the compounds with R102AZ6The same example. As R102BZ6Preferred examples of (3) include102AZ6The same preferred examples as those of (1). R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6The hydrocarbon group and the heterocyclic group having 1 to 40 carbon atoms may have a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
L1preferably-CO-.
R11BZ6The alkyl group is an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent.
R11BZ6The aliphatic hydrocarbon group has 1 to 40 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and further preferably 1 to 15 carbon atoms.
The aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic ring.
As R11BZ6Examples of the saturated or unsaturated chain aliphatic hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, and particularly preferably 1 to 10.
As R11BZ6Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, and 3-methylcyclohexylCyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, cycloalkyl groups such as 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, 2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl are particularly preferable.
R11BZ6The aliphatic hydrocarbon group represented by (a) may be a group in which a hydrogen atom contained in the above-mentioned aliphatic hydrocarbon group is substituted with an aromatic hydrocarbon group having 1 to 40 carbon atoms or a group in which the above-mentioned aliphatic hydrocarbon groups are combined.
Examples of the aromatic hydrocarbon group include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, an o-isopropylphenyl group, an m-isopropylphenyl group, a p-isopropylphenyl group, aromatic hydrocarbon groups such as o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, mesityl, 2, 6-bis (2-propyl) phenyl, 2,4, 6-trimethylphenyl, 1-naphthyl, 2-naphthyl, 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, and anthracenyl; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
Examples of the group in which a hydrogen atom contained in the above-mentioned aliphatic hydrocarbon group is substituted with an aromatic hydrocarbon group having 1 to 40 carbon atoms include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl. Examples of the group formed by combining the above-mentioned aliphatic hydrocarbon groups include (cycloalkyl) alkyl groups such as cyclohexylmethyl groups. The number of carbon atoms of a group in which a hydrogen atom contained in an aliphatic hydrocarbon group is substituted with an aromatic hydrocarbon group having 1 to 40 carbon atoms or a group in which aliphatic hydrocarbon groups are combined is preferably 4 to 30, more preferably 4 to 20, and further preferably 4 to 15.
R11BZ6The aliphatic hydrocarbon group having 1 to 40 carbon atoms, phenyl group, naphthyl group, tetrahydronaphthyl group, thienyl group, furyl group and pyridyl group may have a substituent.
Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
In the compound IZ6-B, R1BZ6Preferably a hydrogen atom.
R2BZ6、R3BZ6、R4BZ6Or R5BZ6Independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N (R)102BZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102BZ6、-O-R102BZ6、-SO3M or-CO2M, more preferably a hydrogen atom or a nitro group. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1.
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6Preferably satisfies at least 1 of (rbb-i) to (rbb-iii), R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(rbb-i)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is-SO3 -or-CO2 -
(rbb-ii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is-CO-R102BZ6、-COO-R101BZ6、-O-R102BZ6、-SO2-R101BZ6、-SO2N(R102BZ6)2、-CON(R102BZ6)2or-N (R)102BZ6)2R is a hydrogen atom101BZ6And R102BZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO 3 -and-CO2 -And (ii) an additional substituent.
(rbb-iii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
In the formula (IZ6-B), R12BZ6And R13BZ6When no ring is formed, the compound IZ6-B is preferably a compound represented by the formula (IZ6-C) (hereinafter, may be referred to as a compound IZ 6-C.).
Figure BDA0003121580680003681
Figure BDA0003121580680003682
Figure BDA0003121580680003683
[ formula (IZ6-C) wherein Ac+、b、c、d、L1And the wavy line means the same as described above.
L2represents-CO-or-SO2-。R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6Independently of one another, represents a hydrogen atom, -CO-R102CZ6、-COO-R101CZ6、-OCO-R102CZ6、-COCO-R102CZ6、-O-R102CZ6、-SO2-R101CZ6、-SO2N(R102CZ6)2、-CON(R102CZ6)2、-N(R102CZ6)2、-NHCO-R102CZ6、-NHCO-N(R102CZ6)2、-NHCOOR102CZ6、-OCON(R102CZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
R2CZ6And R3CZ6、R3CZ6And R4CZ6And R4CZ6And R5CZ6Each of which may be bonded to each other to form a ring.
R101CZ6Independently represent a carbon atom number of 1 to E which may have a substituent40 or a heterocyclic group which may have a substituent.
R102CZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents the same meaning as described above.
The formula (IZ6-C ') and the formula (IZ 6-C') each represent a partial structure of the formula (IZ6-C), A c+、b、c、d、R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、L1And L2Represents the same meaning as the corresponding symbol in the formula (IZ 6-C).
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6、R102CZ6、L1、L2M, c or Ac+When there are a plurality of them, they may be the same or different.
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6Satisfies at least 1 of (rc-i) to (rc-iii), R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(rc-i)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is-SO3 -or-CO2 -
(rc-ii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is-CO-R102CZ6、-COO-R101CZ6、-OCO-R102CZ6、-COCO-R102CZ6、-O-R102CZ6、-SO2-R101CZ6、-SO2N(R102CZ6)2、-CON(R102CZ6)2、-N(R102CZ6)2、-NHCO-R102CZ6、-NHCO-N(R102CZ6)2、-NHCOOR102CZ6or-OCON (R)102CZ6)2R is a hydrogen atom101CZ6And R102CZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). The hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rc-iii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
a represents the same meaning as the symbol in the formula (IZ 6-B). When a plurality of a exist, they may be the same or different.
The partial structure represented by the formula (IZ 6-C') has the same negative valence as the partial structure represented by the formula (IZ6-C ") has the same positive valence in absolute value. ]
As R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6Examples thereof include the compounds with R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same example. As R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6Preferred examples of (3) include 1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same preferred examples as those of (1).
As R101CZ6Examples thereof include the compounds with R101AZ6The same example. As R101CZ6Preferred examples of (3) include101AZ6The same preferred examples as those of (1).
As R102CZ6Examples thereof include the compounds with R102AZ6The same example. As R102CZ6Preferred examples of (3) include102AZ6The same preferred examples as those of (1).
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6The hydrocarbon group and the heterocyclic group having 1 to 40 carbon atoms may have a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
L1Or L2preferably-CO-. Preferably, R11CZ6And R14CZ6Are identical radicals, L1And L2Are the same group.
R11CZ6And R14CZ6Independently of each other, it is preferably an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, or a naphthyl group which may have a substituentA furyl group which may have a substituent or a pyridyl group which may have a substituent.
Examples of the optionally substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, the optionally substituted phenyl group, the optionally substituted naphthyl group, the optionally substituted tetrahydronaphthyl group, the optionally substituted thienyl group, the optionally substituted furyl group or the optionally substituted pyridyl group include those related to R in the compound IZ6-B 11BZ6Preferable examples of the above-mentioned (a) include the same examples as those of the above-mentioned aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent(s), the phenyl group which may have a substituent(s), the naphthyl group which may have a substituent(s), the tetrahydronaphthyl group which may have a substituent(s), the thienyl group which may have a substituent(s), the furyl group which may have a substituent(s), and the pyridyl group which may have a substituent(s).
In the compound IZ6-C, R1CZ6Preferably a hydrogen atom.
R2CZ6、R3CZ6、R4CZ6And R5CZ6Independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N (R)102CZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102CZ6、-O-R102CZ6、-SO3M or-CO2M, more preferably a hydrogen atom or a nitro group. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1.
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6Preferably satisfies at least 1 of (rcc-i) to (rcc-iii), R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(rcc-i)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is-SO3 -or-CO2 -
(rcc-ii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is-CO-R102CZ6、-COO-R101CZ6、-COCO-R102CZ6、-O-R102CZ6、-SO2-R101CZ6、-SO2N(R102CZ6)2、-CON(R102CZ6)2、-N(R102CZ6)2、-NHCO-N(R102CZ6)2、-NHCOOR102CZ6or-OCON (R)102CZ6)2R is a hydrogen atom101CZ6And R102CZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO 3 -and-CO2 -And (ii) an additional substituent.
(rcc-iii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6Preferably, at least 1 of (rc-I) and (rc-II) is satisfied.
(rc-I)R2CZ6、R3CZ6、R4CZ6、R5CZ6At least one of which is-SO3 -or-CO2 -。(rc-II)R1CZ6、R11CZ6And R14CZ6At least one of which is a compound having-SO3 -or-CO2 -The optionally substituted hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6Preferably, at least 1 of (rcc-I) and (rcc-II) is satisfied.
(rcc-I)R2CZ6、R3CZ6、R4CZ6、R5CZ6At least one of which is-SO3 -or-CO2 -
(rcc-II)R1CZ6、R11CZ6And R14CZ6At least one of which is a compound having-SO3 -or-CO2 -The hydrocarbon group having 1 to 40 carbon atoms which may have a substituent(s). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
Wherein R is1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6having-SO of3 -or-CO2 -The total number of (a) is a.
In the compound IZ6-B, R12BZ6And R13BZ6When a ring is formed, the compound IZ6-B is preferably a compound represented by the formula (IZ6-D) (hereinafter, may be referred to as a compound IZ 6-D.).
Figure BDA0003121580680003721
Figure BDA0003121580680003722
Figure BDA0003121580680003723
[ formula (IZ6-D) wherein Ac+、b、c、d、L1And the wavy line means the same as described above. R 20DZ6And R30DZ6Bonded to form a ring Q. The ring Q may have a substituent, and is a ring having 5 to 7 ring-constituting elements, and the ring Q may be a hydrocarbon ring or a heterocyclic ring. The following rings may be fused/condensed on ring Q: a monocyclic ring which is selected from hydrocarbon rings and hetero rings and which may have a substituent, wherein the number of constituent elements of the ring is 5 to 7; or 2 or more condensed rings obtained by condensing the monocyclic rings.
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6Independently of one another, represents a hydrogen atom, -CO-R102DZ6、-COO-R101DZ6、-OCO-R102DZ6、-COCO-R102DZ6、-O-R102DZ6、-SO2-R101DZ6、-SO2N(R102DZ6)2、-CON(R102DZ6)2、-N(R102DZ6)2、-NHCO-R102DZ6、-NHCO-N(R102DZ6)2、-NHCOOR102DZ6、-OCON(R102DZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
R2DZ6And R3DZ6、R3DZ6And R4DZ6And R4DZ6And R5DZ6Each of which may be bonded to each other to form a ring.
R101DZ6Independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R102DZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted hydrocarbon groupA heterocyclic group having a substituent.
M represents the same meaning as described above.
The formulae (IZ 6-D') and (IZ6-D ") each represent a partial structure of the formula (IZ6-D), Ac+、b、c、d、R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R20DZ6、R30DZ6And L1Represents the same meaning as the corresponding symbol in the formula (IZ 6-D).
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6、L1、M、R20DZ6、R30DZ6Ring Q, c or Ac+When there are a plurality of them, they may be the same or different.
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6And ring Q satisfies at least 1 of (rd-i) to (rd-iv), R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6and-SO of ring Q3 -or-CO2 -The total number of (a) is a.
(rd-i)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is-SO3 -or-CO2 -
(rd-ii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is-CO-R102DZ6、-COO-R101DZ6、-OCO-R102DZ6、-COCO-R102DZ6、-O-R102DZ6、-SO2-R101DZ6、-SO2N(R102DZ6)2、-CON(R102DZ6)2、-N(R102DZ6)2、-NHCO-R102DZ6、-NHCO-N(R102DZ6)2、-NHCOOR102DZ6or-OCON (R)102DZ6)2R is a hydrogen atom101DZ6And R102DZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rd-iii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). The hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rd-iv) Ring Q has-SO3 -or-CO2 -
a represents the same meaning as the symbol in the formula (IZ 6-B). When a plurality of a exist, they may be the same or different.
The partial structure represented by the formula (IZ 6-D') has the same negative valence as the partial structure represented by the formula (IZ6-D ") has the same positive valence in absolute value. ]
The number of ring-constituting elements is preferably 5 to 6.
These monocyclic or condensed rings are preferably bonded to ring Q at 2 positions to form a condensed ring.
Examples of the ring Q and the ring having a monocyclic or condensed ring fused thereto include those similar to those of the above-mentioned group A.
Among them, preferred are formula (Q1), formula (Q4), formula (Q7), formula (Q8) and formula (Q18), and more preferred are formula (Q8) and formula (Q18).
The monocyclic ring (the monocyclic ring is selected from hydrocarbon rings and hetero rings) which may have a substituent, or the condensed ring in which 2 or more of the monocyclic rings are condensed, wherein the number of the constituent elements of the ring Q and the ring which may be condensed/condensed on the ring Q is 5 to 7, may haveHas a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent.
Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
As R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6Examples thereof include the compounds with R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same example.
As R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6Preferred examples of (3) include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same preferred examples as those of (1).
As R101DZ6Examples thereof include the compounds with R101AZ6The same example. As R101DZ6Preferred examples of (3) include101AZ6The same preferred examples as those of (1).
As R102DZ6Examples thereof include the compounds with R102AZ6The same example. As R102DZ6Preferred examples of (3) include102AZ6The same preferred examples as those of (1).
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6And R102DZ6Carbon ofThe hydrocarbyl group and the heterocyclic group having 1 to 40 atoms may have a substituent. Examples of the substituent include 1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
L1preferably-CO-.
R11DZ6Independently of each other, an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent is preferable.
Examples of the optionally substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, the optionally substituted phenyl group, the optionally substituted naphthyl group, the optionally substituted tetrahydronaphthyl group, the optionally substituted thienyl group, the optionally substituted furyl group or the optionally substituted pyridyl group include those related to R in the compound IZ6-B11BZ6Preferable examples of the above-mentioned (a) include the same examples as those of the above-mentioned aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent(s), the phenyl group which may have a substituent(s), the naphthyl group which may have a substituent(s), the tetrahydronaphthyl group which may have a substituent(s), the thienyl group which may have a substituent(s), the furyl group which may have a substituent(s), and the pyridyl group which may have a substituent(s).
In the compound IZ6-D, R1DZ6Preferably a hydrogen atom.
R2DZ6、R3DZ6、R4DZ6And R5DZ6Independently of each otherPreferably a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N (R)102DZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102DZ6、-O-R102DZ6、-SO3M or-CO2M, more preferably a hydrogen atom or a nitro group. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1.
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6And ring Q preferably satisfies at least 1 of (rdd-i) to (rdd-iv), R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6and-SO of ring Q3 -or-CO2 -The total number of (a) is a.
(rdd-i)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is-SO3 -or-CO2 -
(rdd-ii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is-CO-R102DZ6、-COO-R101DZ6、-O-R102DZ6、-SO2-R101DZ6、-SO2N(R102DZ6)2、-CON(R102DZ6)2or-N (R)102DZ6)2R is a hydrogen atom101DZ6And R102DZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rdd-iii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At leastOne is having a-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). The hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rdd-iv) Ring Q has-SO3 -or-CO2 -
The compound IZ6-D is more preferably a compound represented by the formula (IZ6-E) (hereinafter, may be referred to as a compound IZ 6-E.).
Figure BDA0003121580680003761
Figure BDA0003121580680003762
Figure BDA0003121580680003763
[ formula (IZ6-E), wherein A isc+、b、c、d、L1And the wavy line means the same as described above.
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6Independently of one another, represents a hydrogen atom, -CO-R102EZ6、-COO-R101EZ6、-OCO-R102EZ6、-COCO-R102EZ6、-O-R102EZ6、-SO2-R101EZ6、-SO2N(R102EZ6)2、-CON(R102EZ6)2、-N(R102EZ6)2、-NHCO-R102EZ6、-NHCO-N(R102EZ6)2、-NHCOOR102EZ6、-OCON(R102EZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -And can haveA substituted hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic group which may have a substituent.
R2EZ6And R3EZ6、R3EZ6And R4EZ6And R4EZ6And R5EZ6Each of which may be bonded to each other to form a ring.
R101EZ6Independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R102EZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents the same meaning as described above.
The formulae (IZ6-E ') and (IZ 6-E') each represent a partial structure of the formula (IZ6-E), Ac+、b、c、d、R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6And L1Represents the same meaning as the corresponding symbol in the formula (IZ 6-E).
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6、R102EZ6、L1M, c or Ac+When there are a plurality of them, they may be the same or different.
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6Satisfies at least 1 of (re-i) to (re-iii), R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(re-i)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is-SO3 -or-CO2 -
(re-ii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is-CO-R102EZ6、-COO-R101EZ6、-OCO-R102EZ6、-COCO-R102EZ6、-O-R102EZ6、-SO2-R101EZ6、-SO2N(R102EZ6)2、-CON(R102EZ6)2、-N(R102EZ6)2、-NHCO-R102EZ6、-NHCO-N(R102EZ6)2、-NHCOOR102EZ6or-OCON (R)102EZ6)2R is a hydrogen atom101EZ6And R102EZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO 3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(re-iii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
a represents the same meaning as the symbol in the formula (IZ 6-D). When a plurality of a exist, they may be the same or different.
The partial structure represented by the formula (IZ6-E ') has the same negative valence as the partial structure represented by the formula (IZ 6-E') has the same positive valence in absolute value. ]
As R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6Examples thereof include the compounds with R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same example.
As R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6Preferred examples of (3) include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same preferred examples as those of (1).
R6EZ6And R7EZ6Independently of each other, a hydrocarbon group having 1 to 10 carbon atoms or a hydrogen atom such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a (2-ethyl) hexyl group, a heptyl group, an octyl group, a nonyl group, a cyclohexyl group, a phenyl group and the like is preferable.
As R101EZ6Examples thereof include the compounds with R101AZ6The same example. As R101EZ6Preferred examples of (3) include101AZ6The same preferred examples as those of (1).
As R102EZ6Examples thereof include the compounds with R 102AZ6The same example. As R102EZ6Preferred examples of (3) include102AZ6The same preferred examples as those of (1).
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6The hydrocarbon group and the heterocyclic group having 1 to 40 carbon atoms may have a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group represented may haveThe same substituents are used. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
L1preferably-CO-.
R11EZ6Independently of each other, an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent is preferable.
Examples of the optionally substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, the optionally substituted phenyl group, the optionally substituted naphthyl group, the optionally substituted tetrahydronaphthyl group, the optionally substituted thienyl group, the optionally substituted furyl group or the optionally substituted pyridyl group include those related to R in the compound IZ6-B 11BZ6Preferable examples of the above-mentioned (a) include the same examples as those of the above-mentioned aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent(s), the phenyl group which may have a substituent(s), the naphthyl group which may have a substituent(s), the tetrahydronaphthyl group which may have a substituent(s), the thienyl group which may have a substituent(s), the furyl group which may have a substituent(s), and the pyridyl group which may have a substituent(s).
In the compound IZ6-E, R1EZ6Preferably a hydrogen atom.
R2EZ6、R3EZ6、R4EZ6And R5EZ6Independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N (R)102EZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102EZ6、-O-R102EZ6、-SO3M or-CO2M,
More preferably a hydrogen atom or a nitro group. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1.
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6Preferably satisfies at least 1 of (ree-i) to (ree-iii), R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(ree-i)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is-SO3 -or-CO2 -
(ree-ii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is-CO-R102EZ6、-COO-R101EZ6、-O-R102EZ6、-SO2-R101EZ6、-SO2N(R102EZ6)2、-CON(R102EZ6)2or-N (R)102EZ6)2R is a hydrogen atom101EZ6And R102EZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(ree-iii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
Specific examples of compound IZ6 include compounds IFZ6-1 to IFZ6-32, compounds IGZ6-1 to IGZ6-32, compounds IHZ6-1 to IHZ6-32, and compounds IJZ6-1 to IJZ6-32, which are shown in tables 1Z6 to 4Z6, among formula (IFZ6), formula (IGZ6), formula (IHZ6), and formula (IJZ 6).
"-SO in the formulae (IFZ6), (IGZ6), (IHZ6) and (IJZ6)3 -"represents a substitution of any hydrogen atom contained in the partial structure in parentheses, respectively.
Figure BDA0003121580680003801
Figure BDA0003121580680003802
Figure BDA0003121580680003803
Figure BDA0003121580680003811
[ Table 1Z6]
TABLE 1Z6
R4Z6 Ac+ b d
IFZ6-1 H Mg2+ 1 1
IFZ6-2 H Ca2+ 1 1
IFZ6-3 H Sr2+ 1 1
IFZ6-4 H Ba2+ 1 1
IFZ6-5 H Ni2+ 1 1
IFZ6-6 H Zn2+ 1 1
IFZ6-7 H Fe2+ 1 1
IFZ6-8 H Co2+ 1 1
IFZ6-9 H Sn2+ 1 1
IFZ6-10 H Mn2+ 1 1
IFZ6-11 H Al3+ 3 2
IFZ6-12 H Fe3+ 3 2
IFZ6-13 H Cr3+ 3 2
IFZ6-14 H Sn4+ 2 1
IFZ6-15 H Mn4+ 2 1
IFZ6-16 NO2 Mg2+ 1 1
IFZ6-17 NO2 Ca2+ 1 1
IFZ6-18 NO2 Sr2+ 1 1
IFZ6-19 NO2 Ba2+ 1 1
IFZ6-20 NO2 Ni2+ 1 1
IFZ6-21 NO2 Zn2+ 1 1
IFZ6-22 NO2 Fe2+ 1 1
IFZ6-23 NO2 Co2+ 1 1
IFZ6-24 NO2 Sn2+ 1 1
IFZ6-25 NO2 Mn2+ 1 1
IFZ6-26 NO2 Al3+ 3 2
IFZ6-27 NO2 Fe3+ 3 2
IFZ6-28 NO2 Cr3+ 3 2
IFZ6-29 NO2 Sn4+ 2 1
IFZ6-30 NO2 Mn4+ 2 1
IFZ6-31 H Cu2+ 1 1
IFZ6-32 NO2 Cu2+ 1 1
[ Table 2Z6]
TABLE 2Z6
R4Z6 Ac+ b d
IGZ6-1 H Mg2+ 1 1
IGZ6-2 H Ca2+ 1 1
IGZ6-3 H Sr2+ 1 1
IGZ6-4 H Ba2+ 1 1
IGZ6-5 H Ni2+ 1 1
IGZ6-6 H Zn2+ 1 1
IGZ6-7 H Fe2+ 1 1
IGZ6-8 H Co2+ 1 1
IGZ6-9 H Sn2+ 1 1
IGZ6-10 H Mn2+ 1 1
IGZ6-11 H Al3+ 3 2
IGZ6-12 H Fe3+ 3 2
IGZ6-13 H Cr3+ 3 2
IGZ6-14 H Sn4+ 2 1
IGZ6-15 H Mn4+ 2 1
IGZ6-16 NO2 Mg2+ 1 1
IGZ6-17 NO2 Ca2+ 1 1
IGZ6-18 NO2 Sr2+ 1 1
IGZ6-19 NO2 Ba2+ 1 1
IGZ6-20 NO2 Ni2+ 1 1
IGZ6-21 NO2 Zn2+ 1 1
IGZ6-22 NO2 Fe2+ 1 1
IGZ6-23 NO2 Co2+ 1 1
IGZ6-24 NO2 Sn2+ 1 1
IGZ6-25 NO2 Mn2+ 1 1
IGZ6-26 NO2 Al3+ 3 2
IGZ6-27 NO2 Fe3+ 3 2
IGZ6-28 NO2 Cr3+ 3 2
IGZ6-29 NO2 Sn4+ 2 1
IGZ6-30 NO2 Mn4+ 2 1
IGZ6-31 H Cu2+ 1 1
IGZ6-32 NO2 Cu2+ 1 1
[ Table 3Z6]
TABLE 3Z6
R4Z6 Ac+ b d
IHZ6-1 H Mg2+ 1 1
IHZ6-2 H Ca2+ 1 1
IHZ6-3 H Sr2+ 1 1
IHZ6-4 H Ba2+ 1 1
IHZ6-5 H Ni2+ 1 1
IHZ6-6 H Zn2+ 1 1
IHZ6-7 H Fe2+ 1 1
IHZ6-8 H Co2+ 1 1
IHZ6-9 H Sn2+ 1 1
IHZ6-10 H Mn2+ 1 1
IHZ6-11 H Al3+ 3 2
IHZ6-12 H Fe3+ 3 2
IHZ6-13 H Cr3+ 3 2
IHZ6-14 H Sn4+ 2 1
IHZ6-15 H Mn4+ 2 1
IHZ6-16 NO2 Mg2+ 1 1
IHZ6-17 NO2 Ca2+ 1 1
IHZ6-18 NO2 Sr2+ 1 1
IHZ6-19 NO2 Ba2+ 1 1
IHZ6-20 NO2 Ni2+ 1 1
IHZ6-21 NO2 Zn2+ 1 1
IHZ6-22 NO2 Fe2+ 1 1
IHZ6-23 NO2 Co2+ 1 1
IHZ6-24 NO2 Sn2+ 1 1
IHZ6-25 NO2 Mn2+ 1 1
IHZ6-26 NO2 Al3+ 3 2
IHZ6-27 NO2 Fe3+ 3 2
IHZ6-28 NO2 Cr3+ 3 2
IHZ6-29 NO2 Sn4+ 2 1
IHZ6-30 NO2 Mn4+ 2 1
IHZ6-31 H Cu2+ 1 1
IHZ6-32 NO2 Cu2+ 1 1
[ Table 4Z6]
TABLE 4Z6
R4Z6 Ac+ b d
IJZ6-1 H Mg2+ 1 1
IJZ6-2 H Ca2+ 1 1
IJZ6-3 H Sr2+ 1 1
IJZ6-4 H Ba2+ 1 1
IJZ6-5 H Ni2+ 1 1
IJZ6-6 H Zn2+ 1 1
IJZ6-7 H Fe2+ 1 1
IJZ6-8 H Co2+ 1 1
IJZ6-9 H Sn2+ 1 1
IJZ6-10 H Mn2+ 1 1
IJZ6-11 H Al3+ 3 2
IJZ6-12 H Fe3+ 3 2
IJZ6-13 H Cr3+ 3 2
IJZ6-14 H Sn4+ 2 1
IJZ6-15 H Mn4+ 2 1
IJZ6-16 NO2 Mg2+ 1 1
IJZ6-17 NO2 Ca2+ 1 1
IJZ6-18 NO2 Sr2+ 1 1
IJZ6-19 NO2 Ba2+ 1 1
IJZ6-20 NO2 Ni2+ 1 1
IJZ6-21 NO2 Zn2+ 1 1
IJZ6-22 NO2 Fe2+ 1 1
IJZ6-23 NO2 Co2+ 1 1
IJZ6-24 NO2 Sn2+ 1 1
IJZ6-25 NO2 Mn2+ 1 1
IJZ6-26 NO2 Al3+ 3 2
IJZ6-27 NO2 Fe3+ 3 2
IJZ6-28 NO2 Cr3+ 3 2
IJZ6-29 NO2 Sn4+ 2 1
IJZ6-30 NO2 Mn4+ 2 1
IJZ6-31 H Cu2+ 1 1
IJZ6-32 NO2 Cu2+ 1 1
For example, compound IFZ6-1 is a compound represented by formula (IFZ 6-1).
Figure BDA0003121580680003841
The compound IZ6 is preferably the compound IFZ6-1 to the compound IFZ6-4, the compound IFZ6-6 to the compound IFZ6-7, the compound IFZ6-10 to the compound IFZ6-13, the compound IFZ6-15 to the compound IFZ6-19, the compound IFZ6-21 to the compound IFZ6-22, the compound IFZ6-25 to the compound IFZ6-28, or the compound IFZ6-30 to the compound IFZ 6-31; compound IGZ6-1 to compound IGZ6-4, compound IGZ6-6 to compound IGZ6-7, compound IGZ6-10 to compound IGZ6-13, compound IGZ6-15 to compound IGZ6-19, compound IGZ6-21 to compound IGZ6-22, compound IGZ6-25 to compound IGZ6-28, and compound IGZ 6-30; compound IHZ6-1 to compound IHZ6-4, compound IHZ6-6 to compound IHZ6-7, compound IHZ6-10 to compound IHZ6-13, compound IHZ6-15 to compound IHZ6-19, compound IHZ6-21 to compound IHZ6-22, compound IHZ6-25 to compound IHZ6-28, and compound IHZ 6-30; and compounds IJZ6-1 to IJZ6-4, IJZ6-6 to IJZ6-7, IJZ6-10 to IJZ6-13, IJZ6-15 to IJZ6-19, IJZ6-21 to IJZ6-22, IJZ6-25 to IJZ6-28 and IJZ6-30,
More preferably, the compound is IFZ6-1 to IFZ6-4, IFZ6-6 to IFZ6-7, IFZ6-10 to IFZ6-13, IFZ6-15 to IFZ6-19, IFZ6-21 to IFZ6-22, IFZ6-25 to IFZ6-28 or IFZ 6-30; and compound IJZ6-1 to compound IJZ6-4, compound IJZ6-6 to compound IJZ6-7, compound IJZ6-10 to compound IJZ6-13, compound IJZ6-15 to compound IJZ6-19, compound IJZ6-21 to compound IJZ6-22, compound IJZ6-25 to compound IJZ6-28, and compound IJZ6-30 to compound IJZ 6-32.
Figure BDA0003121580680003851
Figure BDA0003121580680003852
Figure BDA0003121580680003853
As the compound (IZ6), the following compounds are preferable:
in the formula (IZ6-C), L1And L2Are the same group and are-CO-or-SO2-, preferably-CO-, R11CZ6And R14CZ6Are identical radicals, are hydroxy, -O-Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R1CZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-20 hydrocarbon group, -SO3 -、-CO2 -、-SO3M or-CO2M,
R2CZ6~R5CZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102CZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102CZ6、-O-R102CZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,R102CZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A hydrocarbyl group having 1 to 20 carbon atoms as a substituent in the group consisting of M,
Ac+is Mg2+、Ca2+、Sr2+、Ba2+、Cd2+、Ni2+、Zn2+、Cu2+、Hg2+、Fe2+、Co2+、Sn2+、Pb2+And Mn2+Metal cation of equivalent 2 valence, Al3+、Fe3+And Cr3+Equi-3 valent metal cation, Sn4+And Mn4+A compound of an equivalent metal cation having a valence of 4, M being a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
L1and L2Are the same group and are-CO-or-SO2-, preferably-CO-, R11CZ6And R14CZ6Are identical radicals, are hydroxy, -O-Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R1CZ6Is a hydrogen atom, R2CZ6~R5CZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102CZ6)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102CZ6、-O-R102CZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,
R102CZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
Ac+is Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Cu2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+Or Mn4+M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
L1and L2Are the same group and are-CO-or-SO2-, preferably-CO-, R11CZ6And R14CZ6Are identical radicals, are hydroxy, -O -Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R1CZ6Is a hydrogen atom, R2CZ6~R5CZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102CZ6)2Nitro, trifluoromethyl, -O-R102CZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,R102CZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, Ac+Is Mg2+、Ca2+、Sr2+、Ba2+、Zn2+、Cu2+、Fe2+、Mn2+、Al3+、Fe3+、Cr3+Or Mn4+And M is a hydrogen atom or an alkali metal atom.
Figure BDA0003121580680003871
Figure BDA0003121580680003872
Figure BDA0003121580680003873
As the compound (IZ6), the following compounds are preferable:
in the formula (IZ6-E), L1is-CO-or-SO2-, preferably-CO-, R11EZ6Is hydroxy, -O-Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R1EZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-20 hydrocarbon group, -SO3 -、-CO2 -、-SO3M or-CO2M,
R2EZ6~R5EZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102EZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102EZ6、-O-R102EZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,
R102EZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO 2A hydrocarbyl group having 1 to 20 carbon atoms as a substituent in the group consisting of M,
R6EZ6and R7EZ6Independently of one another, are hydrogen atoms or may have radicals selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-20 hydrocarbon group, -SO3 -、-CO2 -、-SO3M or-CO2M,
Ac+Is Mg2+、Ca2+、Sr2+、Ba2+、Cd2+、Ni2+、Zn2+、Cu2+、Hg2+、Fe2+、Co2+、Sn2+、Pb2+And Mn2+Metal cation of equivalent 2 valence, Al3+、Fe3+And Cr3+Equi-3 valent metal cation, Sn4+And Mn4+And the equivalent of a metal cation having a valence of 4,
a compound in which M is a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
L1is-CO-or-SO2-, preferably-CO-,
R11EZ6is hydroxy, -O-Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1EZ6is a hydrogen atom, R2EZ6~R5EZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102EZ6)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102EZ6、-O-R102EZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,
R102EZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R6EZ6and R7EZ6Independently of one another, are hydrogen atoms or may have radicals selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, A c+Is Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Cu2+、Fe2 +、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+Or Mn4+M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
L1is-CO-or-SO2-, preferably-CO-, R11EZ6Is hydroxy, -O-Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1EZ6is a hydrogen atom, R2EZ6~R5EZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102EZ6)2Nitro, trifluoromethyl, -O-R102EZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,R102EZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R6EZ6And R7EZ6Independently represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, Ac+Is Mg2+、Ca2+、Sr2+、Ba2+、Zn2+、Cu2+、Fe2+、Mn2+、Al3+、Fe3+、Cr3+Or Mn4+And M is a hydrogen atom or an alkali metal atom.
The compound represented by formula (IZ6) can be produced by reacting the compound represented by formula (JZ6) with the compound represented by formula (KZ 6). In particular, 1 or 2 or more compounds of formula (JZ6) and formula (KZ6) may be used.
Figure BDA0003121580680003891
[ in the formula (JZ6), the formula (KZ6) and the formula (IZ6), a, b, c, D, D, Z and Ac+The same meanings as described above are indicated. ZZ represents-SO3M or-CO2And M. M represents the same meaning as described above. MM denotes the direction of inclusion A c+A metal compound which provides 0 or more and c or less electrons.
When a plurality of compounds represented by the formula (JZ6), D, ZZ, a, MM, and M are present, they may be the same or different. ]
Examples of the compound represented by formula (KZ6) include:
comprises the direction Ac+Inorganic compounds such as chlorides, bromides, iodides, sulfates, nitrates, fluorosulfonates, and phosphates of metals that provide 0 or more and c or less electrons; comprises the direction Ac+Sulfonates such as methanesulfonate, trifluoromethanesulfonate and p-toluenesulfonate of a metal which provide 0 or more and c or less electrons;
comprises the direction Ac+Carboxylates such as acetates, citrates, formates, gluconates, lactates, oxalates, and tartrates of metals that provide 0 or more and c or less electrons;
substituted by alkoxy groups such as methoxy, ethoxy, tert-butoxy, etc. to Ac+A metal providing 0 or more and c or less electrons; substituted by butyl, tert-butyl, phenyl, etc. to Ac+A metal providing 0 or more and c or less electrons;
by substitution of hydroxy groupsIn the direction of Ac+A metal which supplies 0 or more and c or less electrons, and the like.
The amount of the compound represented by the formula (KZ6) used is usually 0.05 to 20 mol, preferably 0.06 to 15 mol, and more preferably 0.1 to 10 mol, based on 1 mol of the compound represented by the formula (JZ 6).
When the compound represented by the formula (JZ6) is reacted with the compound represented by the formula (KZ6), a base is preferably present. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide, organic metal compounds such as butyllithium, tert-butyllithium, and phenyllithium, and inorganic bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide.
The amount of the base used is usually 0.0001 to 10 moles, preferably 0.0001 to 8 moles, more preferably 0.0001 to 5 moles, and still more preferably 0.0001 to 4 moles, based on 1 mole of the compound represented by formula (JZ 6).
The reaction of the compound represented by the formula (JZ6) with the compound represented by the formula (KZ6) can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; 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 acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably water, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (JZ 6).
The reaction temperature of the compound represented by the formula (JZ6) and the compound represented by the formula (KZ6) is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
When the compound represented by the formula (IZ6) is a compound represented by the formula (IZ6-A), it can be produced in the same manner as described above. Specifically, the compound represented by the formula (JJZ6) can be produced by reacting a compound represented by the formula (KZ 6). In particular, 1 or 2 or more compounds of formula (JJZ6) and (KZ6) may be used, respectively.
Figure BDA0003121580680003911
[ formula (JJZ6), formula (KZ6) and formula (IZ6-A) wherein Ac+、b、c、d、R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6And the wavy line means the same as described above.
R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6And R13AAZ6Independently of one another, represents a hydrogen atom, -CO-R102AAZ6、-COO-R101AAZ6、-OCO-R102AAZ6、-O-R102AAZ6、-SO2-R101AAZ6、-SO2N(R102AAZ6)2、-CON(R102AAZ6)2、-N(R102AAZ6)2、-NHCO-R102AAZ6Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a C1-40 hydrocarbon group which may have a substituent orA heterocyclic group which may have a substituent.
R2AAZ6And R3AAZ6、R3AAZ6And R4AAZ6、R4AAZ6And R5AZ6、RAAA1Z6And RAAA2Z6And R12AAZ6And R13AAZ6Each of which may be bonded to each other to form a ring.
R101AAZ6Independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R102AAZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents the same meaning as described above. R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6、R13AAZ6、R101AAZ6、R102AAZ6Or when there are a plurality of M, they may be the same or different.
R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6、R13AAZ6、R101AAZ6And R102AAZ6Satisfies at least 1 of (j-i) to (j-iii), R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6、R13AAZ6、R101AAZ6And R102AAZ6having-SO of3M or-CO2The total number of M is more than a.
(j-i)R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6And R13AAZ6At least one of which is-SO3M or-CO2M。
(j-ii)R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6And R13AAZ6At least one of which is-CO-R102AAZ6、-COO-R101AAZ6、-OCO-R102AAZ6、-O-R102AAZ6、-SO2-R101AAZ6、-SO2N(R102AAZ6)2、-CON(R102AAZ6)2、-N(R102AAZ6)2or-NHCO-R102AAZ6R is a hydrogen atom101AAZ6And R102AAZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(j-iii)R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6And R13AAZ6At least one of which is a compound having-SO3M or-CO2M is a hydrocarbon group having 1 to 40 carbon atoms or has-SO3M or-CO2A heterocyclic group of M. Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
a represents the same meaning as the symbol in the formula (IZ 6). When a plurality of a exist, they may be the same or different. ]
With respect to the compound represented by the formula (JJZ6) (hereinafter, may be referred to as compound JJZ6), R1AAZ6In the case of a hydrogen atom, the compound represented by the formula (pt1Z6) (hereinafter, may be referred to as a phthalonitrile compound) and the compound represented by the formula (pt2Z6) (hereinafter, may be referred to as an alkoxide compound) are reacted with each other, and then the compound represented by the formula (pt3Z6) (hereinafter, may be referred to as a compound pt3Z6) and the compound represented by the formula (pt4Z6) (hereinafter, may be referred to as a compound pt4Z6) are further reacted with each other in the presence of an acid. In addition, R 1AAZ6When not a hydrogen atom, a compound represented by the formula (pt5Z6) (hereinafter, may be referred to as a compound pt5Z 6).) The reaction to produce a compound represented by formula (JJZ 6). Here, the compounds represented by the formula (pt1Z6), the formula (pt2Z6), the formula (pt3Z6), the formula (pt4Z6) and the formula (pt5Z6) may be independent of each other, individual compounds, or a mixture of different compounds.
Figure BDA0003121580680003931
In [ formula (pt1Z6), formula (pt2Z6), formula (pt3Z6), formula (pt4Z6), formula (pt5Z6) and formula (JJZ6), R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6And R13AAZ6The same meanings as described above are indicated. R50Z6Represents an alkyl group having 1 to 20 carbon atoms. M1Z6Represents an alkali metal atom. LG represents a halogen atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group.]
As R50Z6Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z6Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z6 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z6 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z6, and the compound pt4Z6 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; 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 acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound.
The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z6 used, relative to R1AAZ6The amount of the compound JJZ 61 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
When the compound pt5Z6 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide, and organic metal compounds such as butyllithium, tert-butyllithium, and phenyllithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1AAZ6The amount of the compound JJZ 61 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
The reaction of compound pt5Z6 can generally be carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1AAZ6The amount of the compound JJZ 61 which is a hydrogen atom is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z6 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound JJZ6 is a compound having no-SO3In the case of the compound of M (hereinafter, sometimes referred to as compound JJJZ6), the compound JJJZ6 may be introduced into-SO by reacting it with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid3M。
With respect to SO in oleum3The amount of (b) is usually 1 to 50 moles, preferably 5 to 40 moles, more preferably 5 to 30 moles, and still more preferably 5 to 25 moles, based on the moles of the compound jjjjz 61.
The amount of sulfuric acid used in oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on the moles of compound jjjjz 61 moles.
The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on the moles of the compound JJJZ 61.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound JJZ6 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, compound JJZ6 can be extracted by filtering the reaction mixture after the reaction is completed. Further, the residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After the completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
The coloring composition of the present invention contains the compound Z and at least one of the resin (B) and the solvent (E), and preferably contains both the resin (B) and the solvent (E) and the compound Z.
The coloring composition of the present invention preferably contains a resin (hereinafter, sometimes referred to as resin (B)). By including the resin (B) in the coloring composition, dispersion stability may be further improved.
< resin (B) >
The resin (B) is preferably an alkali-soluble resin, and more preferably a polymer having a structural unit derived from at least 1 monomer (a) (hereinafter, sometimes referred to as "(a)") selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride.
The resin (B) is preferably a copolymer having a structural unit derived from a monomer (B) (hereinafter sometimes referred to as "(B)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, and other structural units.
Examples of other structural units include: a structural unit derived from a monomer (c) copolymerizable with the monomer (a) (however, it is different from the monomer (a) and the monomer (b) and may be referred to as "(c)" hereinafter), a structural unit having an ethylenically unsaturated bond, and the like.
Examples of (a) include:
unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid;
unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5, 6-tetrahydrophthalic acid, 1,2,3, 6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1, 4-cyclohexenedicarboxylic acid;
carboxyl group-containing bicyclic unsaturated compounds such as methyl-5-norbornene-2, 3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5, 6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxymethylbicyclo [2.2.1] hept-2-ene and 5-carboxyethylbicyclo [2.2.1] hept-2-ene; carboxylic acid anhydrides such as anhydrides of the above unsaturated dicarboxylic acids other than fumaric acid and mesaconic acid; unsaturated mono [ (meth) acryloyloxyalkyl ] esters of 2-or more-membered polycarboxylic acids such as succinic acid mono [ 2- (meth) acryloyloxyethyl ] ester and phthalic acid mono [ 2- (meth) acryloyloxyethyl ] ester;
And unsaturated acrylates containing a hydroxyl group and a carboxyl group in the same molecule, such as α - (hydroxymethyl) acrylic acid.
Among these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an aqueous alkaline solution.
(b) The polymerizable compound has a cyclic ether structure having 2 to 4 carbon atoms (for example, at least 1 selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) Preferably, the monomer has a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
Examples of (b) include: a monomer (b1) (hereinafter sometimes referred to as "(b 1)") having an oxetanyl group and an ethylenically unsaturated bond, a monomer (b2) (hereinafter sometimes referred to as "(b 2)") having an oxetanyl group and an ethylenically unsaturated bond, and a monomer (b3) (hereinafter sometimes referred to as "(b 3)") having a tetrahydrofuranyl group and an ethylenically unsaturated bond.
Examples of (b1) include: a monomer (b1-1) (hereinafter sometimes referred to as "(b 1-1)") having a structure obtained by epoxidizing a linear or branched aliphatic unsaturated hydrocarbon, and a monomer (b1-2) (hereinafter sometimes referred to as "(b 1-2)") having a structure obtained by epoxidizing an alicyclic unsaturated hydrocarbon.
As (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable. Specific examples of (b1-1) include glycidyl (meth) acrylate,. beta. -methylglycidyl (meth) acrylate,. beta. -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, vinylbenzyl glycidyl ether,. alpha. -methylvinylbenzyl glycidyl ether, 2, 3-bis (glycidyloxymethyl) styrene, 2, 4-bis (glycidyloxymethyl) styrene, 2, 5-bis (glycidyloxymethyl) styrene, 2, 6-bis (glycidyloxymethyl) styrene, 2,3, 4-tris (glycidyloxymethyl) styrene, 2,3, 5-tris (glycidyloxymethyl) styrene, 2,3, 6-tris (glycidyloxymethyl) styrene, 3,4, 5-tris (glycidyloxymethyl) styrene, 2,4, 6-tris (glycidyloxymethyl) styrene and the like.
Examples of (b1-2) include vinylcyclohexene monooxide, 1, 2-epoxy-4-vinylcyclohexane (for example, CELLOXIDE (registered trademark) 2000 (manufactured by DAicel Co., Ltd.), (3, 4-epoxycyclohexylmethyl (meth) acrylate (for example, CYCLOMER (registered trademark) A400 (manufactured by Daicel Co., Ltd.), (3, 4-epoxycyclohexylmethyl (meth) acrylate (for example, CYCLOMER (registered trademark) M100 (manufactured by Daicel Co., Ltd.)), the compound represented by the formula (BI), and the compound represented by the formula (BII).
Figure BDA0003121580680003981
[ formula (BI) and formula (BII) wherein RaAnd RbIndependently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, the alkyl groupThe hydrogen atoms contained in the radicals may be substituted by hydroxyl groups. XaAnd XbIndependently of one another, represents a single bond, -Rc-、*-Rc-O-、*-Rc-S-or Rc-NH-。RcRepresents an alkanediyl (alkanediyl) group having 1 to 6 carbon atoms. Denotes a bond to O.]
The compound represented by formula (BI) includes compounds represented by any one of formulae (BI-1) to (BI-15), preferably compounds represented by formulae (BI-1), (BI-3), (BI-5), (BI-7), (BI-9), and (BI-11) to (BI-15), and more preferably compounds represented by formulae (BI-1), (BI-7), (BI-9), and (BI-15).
Figure BDA0003121580680003991
The compound represented by formula (BII) includes compounds represented by any one of formulae (BII-1) to (BII-15), preferably compounds represented by formulae (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15), and more preferably compounds represented by formulae (BII-1), (BII-7), (BII-9), and (BII-15).
Figure BDA0003121580680004001
The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone or in combination. When they are used in combination, the content ratio of the compound represented by the formula (BI) to the compound represented by the formula (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and further preferably 20:80 to 80:20 on a molar basis.
Examples of (c) include: methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, and (meth) acrylic acidLauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, tricyclo [5.2.1.0 (meth) acrylate2,6]Decan-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decan-9-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decen-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6](meth) acrylates such as decen-9-yl ester, dicyclopentanyl oxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, and benzyl (meth) acrylate;
hydroxyl group-containing (meth) acrylates such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate; bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2 '-hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5, 6-dihydroxybicyclo [2.2.1] hept-2-ene, 5, 6-bis (hydroxymethyl) bicyclo [2.2.1] hept-2-ene, 5, 6-bis (2' -hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5, 6-dimethoxybicyclo [2.2.1] hept-2-ene, 5, 6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept-2-ene, bicyclic unsaturated compounds such as 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonybicyclo [2.2.1] hept-2-ene, 5-phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5, 6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept-2-ene and 5, 6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene; dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl 3-maleimidobenzoate, N-succinimidyl 4-maleimidobutyrate, N-succinimidyl 6-maleimidohexanoate, N-succinimidyl 3-maleimidopropionate and N- (9-acridinyl) maleimide;
Vinyl group-containing aromatic compounds such as styrene, α -methylstyrene, vinyltoluene and p-methoxystyrene; vinyl group-containing nitriles such as (meth) acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth) acrylamide; esters such as vinyl acetate; dienes such as 1, 3-butadiene, isoprene and 2, 3-dimethyl-1, 3-butadiene; and so on.
Among these, styrene, vinyltoluene, and tricyclo [5.2.1.0 (meth) acrylate are preferable from the viewpoint of copolymerization reactivity and heat resistance2,6]Decan-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decan-9-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decen-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decen-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1]Hept-2-ene, benzyl (meth) acrylate, and the like.
The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth) acryloyl group. The resin having such a structural unit can be obtained by adding a monomer having an ethylenically unsaturated bond in a group reactive with the group (a) and/or (b) to a polymer having a structural unit derived from (a) and/or (b).
Examples of such a structural unit include a structural unit in which glycidyl (meth) acrylate is added to a (meth) acrylic acid unit, a structural unit in which 2-hydroxyethyl (meth) acrylate is added to a maleic anhydride unit, and a structural unit in which glycidyl (meth) acrylate is added to a (meth) acrylic acid unit. When these structural units have a hydroxyl group, a structural unit obtained by further adding a carboxylic anhydride may be mentioned as a structural unit having an ethylenically unsaturated bond.
The polymer having a structural unit derived from (a) can be produced, for example, by polymerizing a monomer constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator and the solvent are not particularly limited, and polymerization initiators and solvents generally used in the art can be used. Examples of the polymerization initiator include azo compounds (e.g., 2 '-azobisisobutyronitrile, 2' -azobis (2, 4-dimethylvaleronitrile), and organic peroxides (e.g., benzoyl peroxide), and any solvent may be used as long as it dissolves the monomers.
The polymer obtained may be used as it is in a solution after the reaction, may be used as a solution obtained by concentration or dilution, or may be used as a copolymer obtained in a solid (powder) form by a method such as reprecipitation.
If necessary, a catalyst for the reaction of a carboxylic acid or a carboxylic anhydride with a cyclic ether (e.g., tris (dimethylaminomethyl) phenol) and a polymerization inhibitor (e.g., hydroquinone) can be used.
Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5, 6-tetrahydrophthalic anhydride, 1,2,3, 6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5, 6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride.
Specific examples of the resin (B) include a 3, 4-epoxycyclohexylmethyl (meth) acrylate/(meth) acrylic acid copolymer, and a 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decyl ester/(meth) acrylic acid copolymer, glycidyl (meth) acrylate/(benzyl (meth) acrylate/(meth) acrylic acid copolymer, glycidyl (meth) acrylate/styrene/(meth) acrylic acid copolymer, and 3, 4-epoxytricyclo [5.2.1.0 ] meth) acrylic acid2,6]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide/(meth) acrylic acid 2-hydroxyethyl ester copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid) 2,6]Decyl ester/(meth) acrylic acid/vinyltoluene copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decyl ester/(meth) acrylic acid 2-ethylhexyl esterEster copolymer, 3, 4-epoxy tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decyl ester/(meth) acrylic acid tricyclo [5.2.1.02,6]Decenyl ester/(meth) acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3- (meth) acryloyloxymethyloxetane/(meth) acrylic acid/styrene copolymer, benzyl (meth) acrylate/(meth) acrylic acid copolymer, styrene/(meth) acrylic acid copolymer, and resins described in each of Japanese patent application laid-open Nos. 9-106071, 2004-29518 and 2004-361455.
Among these, the resin (B) is preferably a copolymer containing a structural unit derived from (a) and a structural unit derived from (B).
In the case where 2 or more species are combined with the resin (B), it is preferable that the resin (B) contains at least 3, 4-epoxytricyclo [5.2.1.0 ] selected from (meth) acrylic acid2,6]Decyl ester/(meth) acrylic acid copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide/(meth) acrylic acid 2-hydroxyethyl ester copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid) 2,6]Decyl ester/(meth) acrylic acid/vinyltoluene copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)2,6]1 or more of decyl ester/(meth) acrylic acid 2-ethylhexyl ester copolymer.
The weight average molecular weight (Mw) of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000. The dispersity [ weight average molecular weight (Mw)/number average molecular weight (Mn) ] of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.
The acid value (in terms of solid content) of the resin (B) is preferably 10 to 300mg-KOH/g, more preferably 20 to 250mg-KOH/g, and still more preferably 30 to 200 mg-KOH/g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required for neutralizing 1g of the resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.
The content of the resin (B) in the coloring composition is preferably 3 to 99% by mass, more preferably 5 to 99% by mass, and still more preferably 7 to 95% by mass, based on the total amount of the solid components.
The coloring composition of the present invention preferably contains a solvent (hereinafter, sometimes referred to as "solvent (E)"). By including the solvent (E) in the coloring composition, the dispersion stability may be further improved.
< solvent (E) >
Examples of the solvent (E) include an ester solvent (a solvent containing-COO-and not containing-O-in the molecule), an ether solvent (a solvent containing-O-and not containing-COO-in the molecule), an ether ester solvent (a solvent containing-COO-and not containing-O-in the molecule), a ketone solvent (a solvent containing-CO-and not containing-COO-in the molecule), an alcohol solvent (a solvent containing OH and not containing-O-, -CO-, and-COO-in the molecule), an aromatic hydrocarbon solvent, an amide solvent, and dimethyl sulfoxide.
Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ -butyrolactone.
Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1, 4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methyl anisole.
Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, and mixtures thereof, Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate, and the like.
Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.
Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin, and the like.
Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene, and the like.
Examples of the amide solvent include N, N-dimethylformamide, N-dimethylacetamide, and N-methylpyrrolidone.
These solvents may be used in combination of 2 or more.
The content of the solvent (E) is preferably 40 to 99% by mass, and more preferably 50 to 95% by mass, based on the total amount of the coloring composition.
In the coloring composition of the present invention, the compound Z is preferably dispersed in the solvent (E).
For the compound Z, the following treatments may be carried out, as required: rosin treatment; surface treatment using a derivative or the like into which an acidic group or a basic group is introduced; grafting treatment of the surface of the compound Z with a polymer compound or the like; micronization treatment by sulfuric acid micronization method; washing treatment with an organic solvent, water or the like for removing impurities; and a treatment of removing ionic impurities by an ion exchange method or the like. Preferably, the particle size of the compound Z is substantially uniform. The compound Z can be dispersed uniformly in the dispersion liquid by adding a dispersant and performing a dispersion treatment.
The dispersant may be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there may be mentioned polyester, polyamine, acrylic and other surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersant include KP (manufactured by shin-Etsu chemical industries, Ltd.), FLOWLEN (manufactured by Kyoho chemical Co., Ltd.), SOLSPERSE (registered trademark) (manufactured by Zeneca), EFKA (registered trademark) (manufactured by BASF (manufactured by Kyoho Co., Ltd.), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Technio Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), BYK (registered trademark) (manufactured by BYK-Chemie (manufactured by Co., Ltd.), and the like.
When a dispersant is used, the amount of the dispersant (solid component) used is preferably 300 parts by mass or less, and more preferably 5 parts by mass or more and 100 parts by mass or less, relative to 100 parts by mass of the compound Z. When the amount of the dispersant used is within the above range, a colored composition having a more uniform dispersion state tends to be obtained.
The content of the compound Z in the coloring composition is usually 0.1 to 60% by mass, preferably 0.5 to 50% by mass, and more preferably 1 to 40% by mass, based on the total amount of the coloring composition.
The content of the compound Z in the coloring composition is usually 1 mass% to 90 mass%, preferably 1 mass% to 80 mass%, and more preferably 2 mass% to 75 mass% with respect to the total amount of the solid content.
When the coloring composition of the present invention contains the compound Z, the coloring composition may further contain a colorant other than the compound Z (that is, the above-mentioned colorant A1Z1, colorant A1Z2, colorant A1Z3, colorant A1Z4, colorant A1Z5, colorant A1Z6, and the like). Hereinafter, the colorant A1Z1, the colorant A1Z2, the colorant A1Z3, the colorant A1Z4, the colorant A1Z5, and the colorant A1Z6 may be collectively referred to as "colorant ZZ". The coloring agent ZZ may contain 1 or 2 or more coloring agents. The colorant ZZ preferably comprises a yellow colorant or a green colorant.
< colorant ZZ >
The coloring agent ZZ may be a dye or a pigment. As The dye, known dyes can be used, and there can be mentioned dyes described in The index of dyes (published by The Society of Dyers and Colourists) and Dyeing notes (color Dyeing company). Further, depending on the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, and the like can be given. These dyes may be used alone, or 2 or more of them may be used in combination.
Specifically, the following dyes are given by the color index (c.i.) number. C.i. solvent yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;
c.i. acid yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
c.i. reactive yellow 2, 76, 116;
C.i. direct yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
c.i. disperse yellow 51, 54, 76;
c.i. solvent orange 2, 7, 11, 15, 26, 41, 54, 56, 99;
c.i. acid orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
c.i. reactive orange 16;
c.i. direct orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
c.i. solvent red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
c.i. acid red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;
c.i. acid violet 34, 102;
c.i. disperse violet 26, 27;
c.i. solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
c.i. solvent blue 14, 18, 35, 36, 45, 58, 59:1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C.i. acid blue 25, 27, 40, 45, 78, 80, 112;
c.i. direct blue 40;
c.i. disperse blue 1, 14, 56, 60;
c.i. solvent green 1, 3, 5, 28, 29, 32, 33;
c.i. acid green 3, 5, 9, 25, 27, 28, 41;
c.i. alkaline green 1;
c.i. vat green 1, etc.
As The Pigment, known pigments can be used, and for example, pigments classified as "pigments (pigments)" in The color index (published by The Society of Dyers and Colourists) can be cited. These may be used alone, or 2 or more of them may be used in combination.
Specifically, there may be mentioned:
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, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214 and the like;
orange pigments such as c.i. pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
red pigments such as c.i. pigment red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273 and the like;
c.i. pigment blue 15, 15:3, 15:4, 15:6, 60, etc.;
C.i. pigment violet 1, 19, 23, 29, 32, 36, 38 and the like violet pigment;
c.i. pigment green 7, 36, 58, 59 and the like.
The colorant ZZ is preferably a yellow dye and a yellow pigment (hereinafter, these may be collectively referred to as "yellow colorant"), a green dye and a green pigment (hereinafter, these may be collectively referred to as "green colorant"), more preferably a yellow pigment and a green pigment, and still more preferably a green pigment.
Examples of the yellow dye include dyes of which hue is classified as yellow among the dyes, and examples of the yellow pigment include pigments of which hue is classified as yellow among the pigments.
Among the yellow pigments, quinophthalone yellow pigment, metal-containing yellow pigment, and isoindoline yellow pigment are preferable, c.i. pigment yellow 129, 138, 139, 150, and 185 are more preferable, and c.i. pigment yellow 138, 139, 150, and 185 are further preferable.
Examples of the green dye include dyes of which hue is classified as green among the dyes, and examples of the green pigment include pigments of which hue is classified as green among the pigments.
Among the green pigments, phthalocyanine pigments are preferable, at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferable, and at least one selected from the group consisting of c.i. pigment green 7, 36, 58 and 59 is further preferable.
In the case where the coloring composition of the present invention contains the colorant ZZ and the solvent (E), a liquid containing the colorant ZZ, which contains the colorant ZZ and the solvent (E), may be prepared in advance, and then the coloring composition may be prepared using the liquid containing the colorant ZZ. In the case where the colorant ZZ is insoluble in the solvent (E), a liquid containing the colorant ZZ may be prepared by dispersing the colorant ZZ in the solvent (E) and mixing them. The liquid containing the colorant ZZ may contain a part or all of the solvent (E) contained in the coloring composition.
Preferably, the coloring composition of the present invention can be produced by mixing the compound Z, the resin (B), and a liquid containing the colorant ZZ and the solvent (E), or by mixing the compound Z, the solvent (E), and a liquid containing the colorant ZZ and the solvent (E), or by mixing the compound Z, the resin (B), the solvent (E), and a liquid containing the colorant ZZ and the solvent (E).
As the above-mentioned production method, the following methods are preferred: a method in which a coloring composition is prepared by mixing the compound Z and the resin (B) using a bead mill or the like, and the obtained coloring composition is mixed with a liquid containing the coloring agent ZZ and containing the solvent (E); alternatively, a method in which the compound Z and the solvent (E) are mixed by a bead mill or the like to prepare a coloring composition, and the obtained coloring composition is mixed with a liquid containing the coloring agent ZZ and containing the solvent (E); alternatively, a method in which the compound Z, the resin (B) and the solvent (E) are mixed by a bead mill or the like to prepare a coloring composition, and the obtained coloring composition is mixed with a liquid containing the colorant ZZ and the solvent (E).
The colorant ZZ preferably contains 1 or more colorants selected from a green colorant and a yellow colorant.
For the coloring agent ZZ, the following treatments may be carried out, as necessary: rosin treatment; surface treatment using a colorant derivative or the like into which an acidic group or a basic group has been introduced; grafting treatment of the surface of the coloring agent ZZ with a high molecular compound or the like; micronization treatment by sulfuric acid micronization method; washing treatment with an organic solvent, water or the like for removing impurities; and a treatment of removing ionic impurities by an ion exchange method or the like. Preferably, the particle size of the colouring agent ZZ is substantially uniform. In the case of the colorant ZZ, the colorant ZZ is dispersed in a liquid containing the colorant ZZ uniformly by the dispersion treatment with the dispersant. The colorant ZZ may be dispersed separately or in a mixture of two or more.
The dispersant may be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there may be mentioned polyester, polyamine, acrylic and other surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersant include KP (manufactured by shin-Etsu chemical industries, Ltd.), FLOWLEN (manufactured by Kyoho chemical Co., Ltd.), SOLSPERSE (registered trademark) (manufactured by Zeneca), EFKA (registered trademark) (manufactured by BASF (manufactured by Kyoho Co., Ltd.), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Technio Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), BYK (registered trademark) (manufactured by BYK-Chemie (manufactured by Co., Ltd.), and the like.
When a dispersant is used for the preparation of the liquid containing the colorant ZZ, the amount of the dispersant (solid component) used is preferably 300 parts by mass or less, more preferably 5 parts by mass or more and 100 parts by mass or less, based on 100 parts by mass of the colorant ZZ. When the amount of the dispersant used is within the above range, a liquid containing the colorant ZZ in a more uniform dispersion state tends to be obtained.
The content of the coloring agent ZZ in the liquid containing the coloring agent ZZ is usually 0.1 to 60% by mass, preferably 0.5 to 50% by mass, and more preferably 1 to 40% by mass, of the total amount of the liquid containing the coloring agent ZZ.
The content of the colorant ZZ in the liquid containing the colorant ZZ is usually 1% by mass or more and 90% by mass or less, preferably 1% by mass or more and 80% by mass or less, and more preferably 2% by mass or more and 75% by mass or less, based on the total amount of the solid components.
The coloring composition of the invention comprises a resin (B), and in the case where a liquid containing a colorant ZZ, which comprises the colorant ZZ and a solvent, is prepared in advance, and then the coloring composition of the invention is prepared using the liquid containing the colorant ZZ, the liquid containing the colorant ZZ may comprise in advance a part or all, preferably a part, of the resin (B) contained in the coloring composition.
By containing the resin (B) in advance, the dispersion stability of the liquid containing the colorant ZZ can be further improved.
The content of the resin (B) in the liquid containing the colorant ZZ is, for example, 1 to 500 parts by mass, preferably 5 to 200 parts by mass, and more preferably 10 to 100 parts by mass with respect to 100 parts by mass of the colorant ZZ.
The content of the colorant ZZZ in the coloring composition, which is a mixture of the compound Z and the colorant ZZ, is usually 1 mass% or more and 90 mass% or less, preferably 1 mass% or more and 80 mass% or less, and more preferably 2 mass% or more and 75 mass% or less, based on the total amount of the solid components.
The content of the compound Z is usually 0.001 mass% or more, preferably 0.003 mass% or more, and more preferably 0.005 mass% or more, and the upper limit is 100 mass% or less, preferably 99.999 mass% or less, and more preferably 99.997 mass% or less, in the total amount of the colorant ZZZ.
The content of the compound Z is usually 0.001 mass% or more, preferably 40 mass% or more, more preferably 50 mass% or more, still more preferably 60 mass% or more, and particularly preferably 70 mass% or more, in the total amount of the yellow coloring agent, and the upper limit is 100 mass% or less, preferably 99.999 mass% or less, and more preferably 99.997 mass% or less.
In the case where the colorant ZZ is contained, the content of the colorant ZZ is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, further preferably 1 part by mass or more, preferably 10000 parts by mass or less, and more preferably 5000 parts by mass or less with respect to 100 parts by mass of the compound Z.
The colored curable composition of the present invention comprises: a compound Z; at least one of a resin (B) and a solvent (E); and a polymerizable compound (C).
< polymerizable Compound (C) >)
The polymerizable compound (C) is a compound polymerizable by an active radical and/or an acid generated by the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenically unsaturated bond, and is preferably a (meth) acrylate compound.
Examples of the polymerizable compound having 1 ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone, and the above-mentioned monomer (a), monomer (b), and monomer (c).
Examples of the polymerizable compound having 2 ethylenically unsaturated bonds include 1, 6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol a, and 3-methylpentanediol di (meth) acrylate.
Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra (meth) acrylate, ethylene glycol-modified dipentaerythritol hexa (meth) acrylate, propylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, caprolactone-modified pentaerythritol tetra (meth) acrylate, and caprolactone-modified dipentaerythritol hexa (meth) The acrylic acid ester and the like are preferably dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate.
The weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.
The content of the polymerizable compound (C) in the colored curable composition is preferably 1 to 65% by mass, more preferably 3 to 60% by mass, and still more preferably 5 to 55% by mass, based on the total amount of the solid components.
The colored curable composition of the invention may contain a polymerization initiator (D).
< polymerization initiator (D) >)
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating an active radical, an acid, or the like by the action of light or heat, and a known polymerization initiator can be used.
Examples of the polymerization initiator (D) include an O-acyloxime compound, an alkylphenone compound, a biimidazole compound, a triazine compound, and an acylphosphine oxide compound.
Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanyl) phenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanyl) phenyl) octan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanyl phenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1- (4-phenylsulfanyl phenyl) -3-cyclohexylpropane-1-one-2-imine -imine, N-acetyloxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethane-1-imine, N-acetyloxy-1- [ 9-ethyl-6- { 2-methyl-4- (3, 3-dimethyl-2, 4-dioxopentylmethyloxy) benzoyl } -9H-carbazol-3-yl ] ethane-1-imine, N-acetyloxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -3-cyclopentylpropane-1-imine and N-benzoyloxy-1- [ 9-Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -3-cyclopentylpropane-1-one-2-imine, and the like. Further, as the O-acyloxime compound, commercially available products such as IRGACURE OXE01, OXE02 (manufactured by BASF corporation), N-1919 (manufactured by ADEKA corporation), and the like can be used. Among them, as the O-acyloxime compound, at least 1 selected from the group consisting of N-benzoyloxy-1- (4-phenylthiophenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylthiophenyl) octan-1-one-2-imine, and N-benzoyloxy-1- (4-phenylthiophenyl) -3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyloxy-1- (4-phenylthiophenyl) octan-1-one-2-imine is more preferable.
Examples of the alkylphenone compound include 2-methyl-2-morpholino (morpholino) -1- (4-methylthiophenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, and 2- (dimethylamino) -2- [ (4-methylphenyl) methyl ] -1- [4- (4-morpholino (morpholino)) phenyl ] butan-1-one. As the alkylphenone compound, commercially available products such as IRGACURE 369, 907 and 379 (manufactured by BASF corporation) can be used.
Examples of the alkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, α -diethoxyacetophenone and benzildimethylketal.
Examples of the biimidazole compound include 2,2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetraphenylbiimidazole, 2 ' -bis (2, 3-dichlorophenyl) -4,4 ', 5,5 ' -tetraphenylbiimidazole (see, for example, japanese patent application laid-open No. 6-75372, japanese patent application laid-open No. 6-75373, etc.), 2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetrakis (alkoxyphenyl) biimidazole, 2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetrakis (dialkoxyphenyl) biimidazole, 2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetrakis (trialkoxyphenyl) biimidazole (for example, see, for example, Japanese patent application laid-open No. 48-38403 and Japanese patent application laid-open No. 62-174204) and imidazole compounds in which the phenyl group at the 4,4 ', 5, 5' -position is substituted with an alkoxycarbonyl group (e.g., Japanese patent application laid-open No. 7-10913).
Examples of the triazine compound include 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6-piperonyl-1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (5-methylfuran-2-yl) vinyl ] -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (furan-2-yl) vinyl ] -one 1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (4-diethylamino-2-methylphenyl) vinyl ] -1,3, 5-triazine, and 2, 4-bis (trichloromethyl) -6- [ 2- (3, 4-dimethoxyphenyl) vinyl ] -1,3, 5-triazine.
Examples of the acylphosphine oxide compound include 2,4, 6-trimethylbenzoyldiphenylphosphine oxide and the like.
Examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4 ' -methyldiphenyl sulfide, 3 ', 4,4 ' -tetrakis (t-butylperoxycarbonyl) benzophenone, and 2,4, 6-trimethylbenzophenone; quinone compounds such as 9, 10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl benzoylformate, titanocene compound, and the like.
These are preferably used in combination with the polymerization initiation assistant (D1) (particularly amines) described later.
The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a bisimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.
The content of the polymerization initiator (D) is preferably 0.001 to 40% by mass, and more preferably 0.01 to 30% by mass, based on the total amount of solid components in the colored curable composition.
The colored curable composition of the invention may contain a polymerization initiator aid (D1).
< polymerization initiation assistant (D1) >)
The polymerization initiation aid (D1) is a compound or a sensitizer used for promoting the polymerization of a polymerizable compound whose polymerization is initiated by a polymerization initiator. In the case of containing the polymerization initiation aid (D1), generally, it may be used in combination with the polymerization initiator (D).
Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N-dimethyl-p-toluidine, 4 ' -bis (dimethylamino) benzophenone (known as Michler's ketone), 4 ' -bis (diethylamino) benzophenone, and 4,4 ' -bis (ethylmethylamino) benzophenone, and 4,4 ' -bis (diethylamino) benzophenone is preferable. As the amine compound, a commercially available compound such as EAB-F (manufactured by UK chemical Co., Ltd.) can be used.
Examples of the alkoxyanthracene compound include 9, 10-dimethoxyanthracene, 2-ethyl-9, 10-dimethoxyanthracene, 9, 10-diethoxyanthracene, 2-ethyl-9, 10-diethoxyanthracene, 9, 10-dibutoxyanthracene, and 2-ethyl-9, 10-dibutoxyanthracene.
Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2, 4-diethylthioxanthone, 2, 4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.
Examples of the carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthyloxyacetic acid and the like.
When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.001 to 30% by mass, more preferably 0.01 to 20% by mass, based on the total amount of solid components in the colored curable composition.
The coloring composition of the present invention may further contain a leveling agent (F) and an antioxidant.
< leveling agent (F) >
Examples of the leveling agent (F) include a silicone surfactant, a fluorine surfactant, and a silicone surfactant having a fluorine atom. They may have a polymerizable group in a side chain.
Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name; manufactured by Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by shin-Etsu chemical Co., Ltd.), TSF400, TSF401, TSF410, F4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Moive Performance Materials Japan Co., Ltd.) can be mentioned.
Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, examples thereof include Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718K (manufactured by DIC corporation), EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352(Mitsubishi Materials Electronic Chemicals Co., manufactured by Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asnitro corporation) and E5844 (Danin fire K., manufactured by Kenkyu K).
Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, there may be mentioned MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (available from DIC Co., Ltd.).
When the leveling agent (F) is contained, the content thereof is usually 0.0005 mass% or more and 1 mass% or less, preferably 0.001 mass% or more and 0.5 mass% or less, more preferably 0.001 mass% or more and 0.2 mass% or less, further preferably 0.002 mass% or more and 0.1 mass% or less, and particularly preferably 0.005 mass% or more and 0.1 mass% or less, based on the total amount of the coloring composition. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
< antioxidant >
The antioxidant may be used alone or in combination of 2 or more from the viewpoint of improving the heat resistance and light resistance of the colorant. The antioxidant is not particularly limited as long as it is an industrially commonly used antioxidant, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant, and the like can be used.
Examples of the phenolic antioxidant include Irganox 1010(イルガノックス 1010: pentaerythritol tetrakis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], manufactured by BASF corporation), Irganox 1076(イルガノックス 1076: octadecyl-3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, manufactured by BASF corporation), Irganox 1330(イルガノックス 1330: 3,3 ', 5,5 ' -hexa-tert-butyl-a, a ' - (mesitylene-2, 4, 6-triyl) tri-p-cresol, manufactured by BASF corporation), Irganox 3114(イルガノックス 3114: 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, manufactured by BASF corporation), Irganox 3790(イルガノックス 3790: 1,3, 5-tris ((4-tert-butyl-3-hydroxy-2, 6-xylyl) methyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, manufactured by BASF (ltd.), Irganox 1035(イルガノックス 1035: thiodiethylene bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], manufactured by BASF corporation), Irganox 1135(イルガノックス 1135: C7-C9 side chain alkyl ester of 3, 5-bis (1, 1-dimethylethyl) -4-hydroxypropionic acid, manufactured by BASF (ltd.), Irganox 1520L (イルガノックス 1520L: 4, 6-bis (octylthiomethyl) o-cresol, manufactured by BASF corporation), Irganox 3125(イルガノックス 3125, manufactured by BASF corporation), Irganox 565(イルガノックス 565: 2, 4-bis (n-octylthio) -6- (4-hydroxy-3 ', 5' -di-tert-butylanilino) -1,3, 5-triazine manufactured by BASF (ltd)), Adekastab AO-80(アデカスタブ AO-80: 3, 9-bis (2- (3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy) -1, 1-dimethylethyl) -2,4,8, 10-tetraoxaspiro (5,5) undecane (manufactured by ADEKA), Sumilizer BHT (スミライザー BHT, manufactured by Sumilizer chemical corporation), Sumilizer GA-80(スミライザー GA-80, manufactured by Sumilizer chemical corporation), Sumilizer GS (スミライザー GS, manufactured by Sumilizer chemical corporation), Cyanox 1790(シアノックス 1790 (manufactured by Cytec), vitamin E (Eisai co., ltd.).
Examples of the phosphorus-based antioxidant include Irgafos 168(イルガフォス 168: tris (2, 4-di-t-butylphenyl) phosphite, manufactured by BASF corporation), Irgafos 12(イルガフォス 12: tris [2- [ [2,4,8, 10-tetra-t-butyldibenzo [ d, f ] [1,3,2] dioxaphosphorin-6-yl ] oxy ] ethyl ] amine, manufactured by BASF corporation), Irgafos 38(イルガフォス 38: bis (2, 4-bis (1, 1-dimethylethyl) -6-methylphenyl) ethyl phosphite, manufactured by BASF corporation), Adekastab 329K (manufactured by ADEKA), Adekastab PEP36 (manufactured by ADEKA), Adekastab PEP-8 ((manufactured by SanEKA), dstab P-EPQ (manufactured by Clariant), Weston 618 (618, manufactured by Weston GE corporation), manufactured by ウェストン 618, manufactured by SAEK, Weston 619G (ウェストン 619G, GE Co., Ltd.), Ultranox 626(ウルトラノックス 626, GE Co., Ltd.), Sumilizer GP (スミライザー GP: 6- [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propoxy ] -2,4,8, 10-tetra-tert-butyldibenzo [ d, f ] [1.3.2] dioxaphosphepin (dioxiphospin)) (manufactured by Sumitomo chemical Co., Ltd.), and the like.
Examples of the sulfur-based antioxidant include dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl thiodipropionate and distearyl thiodipropionate, and β -alkylmercaptopropionate compounds of polyhydric alcohols such as tetrakis [ methylene (3-dodecylthio) propionate ] methane.
< other ingredients >
The coloring composition of the present invention may contain additives known in the art, such as a filler, another polymer compound, an adhesion promoter, a light stabilizer, and a chain transfer agent, as required.
Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, and the like, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane, etc.
< color filter >
The color filter can be formed from the colored composition or the colored curable composition of the invention. As a method for forming a colored pattern, a photolithography method, an ink jet method, a printing method, and the like can be mentioned, and a photolithography method can be preferably mentioned. The photolithography method is as follows: the colored curable composition is applied to a substrate and dried to form a colored curable composition layer, and the colored curable composition layer is exposed to light through a photomask and developed. In the photolithography method, the colored curable composition preferably contains a polymerization initiator (D). A colored coating film which is a cured product of the colored curable composition layer can be formed by a photolithography method without using a photomask and/or without performing development during exposure. The colored pattern and the colored coating film formed as described above can be used as the color filter of the present invention.
The film thickness of the color filter to be produced is not particularly limited, and may be suitably adjusted according to the purpose, use, and the like, and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.
As the substrate, a glass plate, a resin plate, silicon, a substrate obtained by forming a thin film of aluminum, silver/copper/palladium alloy, or the like on the above substrate, or the like can be used. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates.
The formation of each color pixel by photolithography can be performed by using a known or commonly used apparatus and conditions. For example, the following method can be used.
First, a colored curable composition is applied onto a substrate, and dried by removing volatile components such as a solvent by heat drying (prebaking) and/or drying under reduced pressure, thereby obtaining a smooth colored curable composition layer.
Examples of the coating method include spin coating, slit and spin coating (slit and spin coating).
Next, the colored curable composition layer is exposed to light through a photomask for forming a target colored pattern. In order to uniformly irradiate the entire exposure surface with parallel light or to accurately align the photomask with the substrate on which the colored curable composition layer is formed, an exposure apparatus such as a mask aligner or a stepper is preferably used.
The exposed colored curable composition layer is brought into contact with a developer to develop the layer, whereby a colored pattern can be formed on the substrate. By the development, the unexposed portion of the colored curable composition layer is dissolved in a developing solution and removed.
As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable.
The developing method may be any of spin immersion (dip method), immersion method, spray method, and the like. In addition, the substrate may be inclined at an arbitrary angle at the time of development.
The developed substrate is preferably washed with water.
Further, the obtained colored pattern is preferably subjected to post-baking.
The color filter is useful as a color filter used in a display device (a liquid crystal display device, an organic EL device, electronic paper, or the like) or a solid-state imaging device, particularly as a color filter used in a liquid crystal display device.
[ examples ]
Hereinafter, "part" means "part by mass" and "%" means "% by mass" unless otherwise specified.
In the following synthesis examples, the structure of the compound was confirmed by NMR (JMM-ECA-500; manufactured by Japan Electron Ltd.) or MASS spectrometry (LC; model 1200 manufactured by Agilent, MASS; model LC/MSD6130 manufactured by Agilent).
The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by GPC under the following conditions.
The device comprises the following steps: HLC-8120GPC (manufactured by Tosoh corporation)
Column: TSK-GELG2000HXL
Column temperature: 40 deg.C
Solvent: tetrahydrofuran (THF)
Flow rate: 1.0 mL/min
Solid content concentration of analysis sample: 0.001 to 0.01% by mass
Sample introduction amount: 50 μ L
A detector: RI (Ri)
Calibration standard substance: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh corporation)
The ratio (Mw/Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) in terms of polystyrene obtained in the above manner was defined as the degree of dispersion.
Example Z1
Example 1Z1
36.2 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 526 parts of methanol were mixed.
While keeping the temperature at 5 ℃, a mixture of 20.9 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 10 parts of methanol was added dropwise to the obtained mixture over 1 hour.
The resulting mixture was stirred at 5 ℃ for 4 hours.
To the obtained mixture were added 13.1 parts of acetic acid and 23.7 parts of ethyl cyanoacetate (manufactured by Tokyo chemical industry Co., Ltd.) while keeping the temperature at 5 ℃ or lower.
The resulting mixture was stirred at 5 ℃ for 1 hour and then at room temperature for 3 days.
To the obtained mixture were added 2.37 parts of ethyl cyanoacetate (manufactured by tokyo chemical industries, ltd.) and 231 parts of methanol, and the mixture was stirred at room temperature for 1 day. To the obtained mixture were added 0.496 parts of ethyl cyanoacetate (manufactured by tokyo chemical industry co.) and 26 parts of methanol, and the mixture was stirred at 40 ℃ for 2 hours and 30 minutes.
To the obtained mixture were added 17.1 parts of acetic acid, 26.9 parts of barbituric acid and 793 parts of water, and the mixture was stirred at 40 ℃ for 2 hours.
To the resulting mixture were added 17.0 parts of acetic acid, 26.9 parts of barbituric acid, 12 parts of methanol, and 12 parts of water, and the mixture was stirred at 40 ℃ for 30 minutes and then at room temperature for 2 days.
The resulting mixture was filtered, and the residue was washed 1 time with 915 parts of 50% aqueous methanol solution, 1 time with 950 parts of 50% aqueous methanol solution, 1 time with 1600 parts of 50% aqueous methanol solution, and 1 time with 1800 parts of water.
The obtained residue was recrystallized from N, N-dimethylformamide to obtain 30.7 parts of a mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ 1-39).
Figure BDA0003121580680004231
Identification of Compound represented by the formula (IZ1-38)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+384
Exact molecular weight (Exact masses): 383
Figure BDA0003121580680004232
Identification of Compound represented by the formula (IZ1-39)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+398
Exact molecular weight (Exact masses): 397
Example 2Z1
A mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ1-21) was obtained in the same manner as in example 1Z1, except that 4-nitrophthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.).
Figure BDA0003121580680004241
Identification of Compound represented by the formula (IZ1-20)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+395
Exact molecular weight (Exact masses): 394
Figure BDA0003121580680004242
Identification of Compound represented by the formula (IZ1-21)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+409
Exact molecular weight (Exact masses): 408
Example 3Z1
A mixture of the compound represented by the formula (IZ1-2) and the compound represented by the formula (IZ1-3) was obtained in the same manner as in example 1Z1, except that 4-nitrophthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.) was replaced with phthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.).
Figure BDA0003121580680004251
Identification of Compound represented by the formula (IZ1-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+339
Exact molecular weight (Exact masses): 338
Figure BDA0003121580680004252
Identification of Compound represented by the formula (IZ1-3)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+353
Exact molecular weight (Exact masses): 352
Example 4Z1
A compound represented by the formula (IZ1-38) was obtained in the same manner as in example 1Z1, except that ethyl cyanoacetate (manufactured by tokyo chemical industry co.) was replaced with methyl cyanoacetate (manufactured by tokyo chemical industry co.).
Figure BDA0003121580680004253
Identification of Compound represented by the formula (IZ1-38)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H ]+384
Exact molecular weight (Exact masses): 383
Example 5Z1
The procedure of example 1Z1 was repeated except for replacing 4-nitrophthalonitrile (manufactured by tokyo chemical industry co., ltd.) with 4-tert-butylphthalonitrile (manufactured by tokyo chemical industry co., ltd.) and replacing ethyl cyanoacetate (manufactured by tokyo chemical industry co., ltd.) with methyl cyanoacetate (manufactured by tokyo chemical industry co., ltd.), thereby obtaining a compound represented by formula (IZ 1-20).
Figure BDA0003121580680004261
Identification of Compound represented by the formula (IZ1-20)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+395
Exact molecular weight (Exact masses): 394
Example 6Z1
The procedure of example 1Z1 was repeated except for replacing 4-nitrophthalonitrile (manufactured by tokyo chemical industry co.) with phthalonitrile (manufactured by tokyo chemical industry co.) and replacing ethyl cyanoacetate (manufactured by tokyo chemical industry co.) with methyl cyanoacetate (manufactured by tokyo chemical industry co.) to obtain a compound represented by formula (IZ 1-2).
Figure BDA0003121580680004262
Identification of Compound represented by the formula (IZ1-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+339
Exact molecular weight (Exact masses): 338
Example 7Z1XXX (tBu)
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the obtained mixture, 5.42 parts of acetic acid and 6.14 parts of ethyl cyanoacetate (manufactured by Tokyo chemical industry Co., Ltd.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days.
To the obtained mixture were added 2.69 parts of acetic acid and 3.07 parts of ethyl cyanoacetate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days.
The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ 1-21).
Figure BDA0003121580680004271
Identification of Compound represented by the formula (IZ1-20)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+395
Exact molecular weight (Exact masses): 394
Figure BDA0003121580680004272
Identification of Compound represented by the formula (IZ1-21)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+409
Exact molecular weight (Exact masses): 408
Example 8Z1XXX (542)
2.57 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 24.5 parts of methanol were mixed. To the resulting mixture, 2.00 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) was added at room temperature. The resulting mixture was stirred at 43 ℃ for 1 hour and 30 minutes.
To the resulting mixture, 2.53 parts of ethyl cyanoacetate (manufactured by Tokyo chemical industry Co., Ltd.), 1.26 parts of acetic acid and 54.5 parts of methanol were added, and the mixture was stirred at 40 ℃ for 1 hour and 30 minutes. To the obtained mixture, 2.84 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.), 1.63 parts of acetic acid and 9 parts of methanol were added, and the mixture was stirred at 40 ℃ for 1 hour. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a mixture of the compound represented by the formula (IZ1-2) and the compound represented by the formula (IZ 1-3).
Figure BDA0003121580680004281
Identification of Compound represented by the formula (IZ1-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+339
Exact molecular weight (Exact masses): 338
Figure BDA0003121580680004282
Identification of Compound represented by the formula (IZ1-3)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+353
Exact molecular weight (Exact masses): 352
Example 9Z1XXX (NO2)
10.0 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 149 parts of methanol were mixed. While keeping the temperature at 2 to 6 ℃, 5.86 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture over 20 minutes. The resulting mixture was stirred for 5 hours while being kept at 5 ℃ or lower. While the resulting mixture was kept at 5 ℃ or lower, 5.79 parts of acetic acid, 5.72 parts of methyl cyanoacetate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 2.88 parts of acetic acid and 2.86 parts of methyl cyanoacetate (manufactured by tokyo chemical industries, ltd.). The resulting mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 140 parts of methanol was added in addition to the above-mentioned methanol. To the obtained mixture were added 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to give a compound represented by the formula (IZ 1-38).
Figure BDA0003121580680004291
Identification of Compound represented by the formula (IZ1-38)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+384
Exact molecular weight (Exact masses): 383
Example 10Z1XXX (tBu)
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the obtained mixture, 5.42 parts of acetic acid and 5.38 parts of methyl cyanoacetate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days.
To the obtained mixture were added 2.69 parts of acetic acid and 2.69 parts of methyl cyanoacetate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days.
The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to give a compound represented by the formula (IZ 1-20).
Figure BDA0003121580680004301
Identification of Compound represented by the formula (IZ1-20)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+395
Exact molecular weight (Exact masses): 394
Example 11Z1XXX (645)
60.0 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 501 parts of methanol were mixed. To the resulting mixture, 46.7 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise over 15 minutes while keeping the temperature at 2 ℃. The resulting mixture was stirred for 5 hours while being maintained at 2 to 6 ℃. 556 parts of methanol was added to the mixture while keeping the temperature at 5 ℃ or lower. To the mixture were added 29.3 parts of acetic acid, 46.5 parts of methyl cyanoacetate, and 22 parts of methanol. The mixture was stirred at room temperature for 12 hours and then at 40 ℃ for 3 hours and 20 minutes. This mixture was mixed with 3.00 parts of acetic acid and 4.71 parts of methyl cyanoacetate, and stirred at 40 ℃ for 1 hour and 25 minutes. This mixture was mixed with 2.98 parts of acetic acid and 4.71 parts of methyl cyanoacetate, and stirred at 40 ℃ for 2 hours. This mixture was mixed with 2.96 parts of acetic acid and 4.70 parts of methyl cyanoacetate, and stirred at 40 ℃ for 2 hours. This mixture was mixed with 1.50 parts of acetic acid and 2.40 parts of methyl cyanoacetate.
In addition, a total of 111 parts of methanol was added up to this time point, in addition to the above-mentioned methanol. The resulting mixture was stirred at 40 ℃ for 1 hour and 40 minutes. To the resulting mixture, 38.1 parts of acetic acid and 60.6 parts of barbituric acid were added, and the mixture was stirred at 40 ℃ for 42 hours. In addition, up to this point in time, a total of 66 parts of methanol was added in addition to the above-mentioned methanol. The mixture was filtered and the residue was washed 6 times with 400 parts of methanol. The residue was purified by column chromatography to give a compound represented by the formula (IZ 1-2).
Figure BDA0003121580680004311
Identification of Compound represented by the formula (IZ1-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+339
Exact molecular weight (Exact masses): 338
Example 12Z1
5.0 parts of 4, 5-dichlorophthalonitrile and 62 parts of methanol were mixed. While the mixture was kept at 5 ℃ or lower, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 5.0 parts by mole of 4, 5-dichlorophthalonitrile was added. The mixture was stirred at 5 ℃ or below for 5 hours. Methyl cyanoacetate 1.5 times the molar amount of 5.0 parts of 4, 5-dichlorophthalonitrile and 6.1 parts of acetic acid were added to the mixture while keeping the temperature at 5 ℃ or lower.
The mixture was stirred at 65 ℃ for 3 days. This mixture was mixed with 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol and 562 parts of water, and stirred at 65 ℃ for 9 days. The solvent was distilled off from the mixture by a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.297 parts of a compound represented by the formula (IZ 1-258).
Figure BDA0003121580680004312
Identification of Compound represented by the formula (IZ1-258)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+407
Exact molecular weight (Exact masses): 406
Example 13Z1XXX (659)
25.9 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 513 parts of methanol were mixed. 30.3 parts of a 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) and 12 parts of methanol were added dropwise to the obtained mixture over 10 minutes while maintaining the temperature at 3 to 5 ℃. The resulting mixture was stirred for 6 hours while being maintained at 3 to 5 ℃. To the obtained mixture were added 19.8 parts of acetic acid, 28.5 parts of t-butyl cyanoacetate and 26 parts of methanol while maintaining the temperature at 3 to 5 ℃. The resulting mixture was stirred at room temperature for 2 days, and then at 40 ℃ for 3 hours. To the resulting mixture were added 5.09 parts of acetic acid and 7.17 parts of tert-butyl cyanoacetate, and the mixture was stirred at 40 ℃ for 4 hours. To the resulting mixture were added 4.95 parts of acetic acid, 7.15 parts of tert-butyl cyanoacetate and 38 parts of methanol, and the mixture was stirred at 40 ℃ for 16 hours. To the resulting mixture were added 19.9 parts of acetic acid, 25.8 parts of barbituric acid, 209 parts of methanol, and 800 parts of water, and the mixture was stirred at 40 ℃ for 3 hours.
The resulting mixture was filtered to give a residue. The residue was purified by column chromatography to give a compound represented by the formula (IZ 1-5).
Figure BDA0003121580680004321
Identification of Compound represented by the formula (IZ1-5)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+381
Exact molecular weight (Exact masses): 380
Example 14Z1XXX (661)
15.1 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 284 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.81 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 18 parts of methanol was added dropwise to the obtained mixture over 10 minutes. The resulting mixture was stirred for 4 hours while being kept at 5 ℃ or lower.
To the obtained mixture, 5.55 parts of acetic acid was added while keeping the temperature at 5 ℃ or lower, and the mixture was stirred for 30 minutes. This mixture was mixed with 12.3 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 14 hours. This mixture was mixed with 0.654 parts of acetic acid and 1.24 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 4 hours. This mixture was mixed with 0.613 part of acetic acid and 1.23 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 3 hours. This mixture was mixed with 0.647 parts of acetic acid and 1.24 parts of t-butyl cyanoacetate. Further, up to this point, a total of 89 parts of methanol was added in addition to the above-mentioned methanol. The mixture was stirred at 40 ℃ for 17 hours. This mixture was mixed with 7.14 parts of acetic acid, 11.3 parts of barbituric acid and 508 parts of water. Up to this point, a total of 117 parts of methanol was added in addition to the above-mentioned methanol. The mixture was stirred at 40 ℃ for 24 hours. This mixture was mixed with 3.65 parts of acetic acid and 5.61 parts of barbituric acid, and stirred at 40 ℃ for 9 hours and at room temperature for 2 days. The mixture was filtered and the residue was washed 3 times with 1330 parts of 50% aqueous methanol solution. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 1-41).
Figure BDA0003121580680004331
Identification of Compound represented by the formula (IZ1-41)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+426
Exact molecular weight (Exact masses): 425
Synthesis example 1
An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and the atmosphere was replaced with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was charged, and the mixture was heated to 80 ℃ with stirring. Then, 38 parts of acrylic acid and 3, 4-epoxytricyclo [5.2.1.0 ] acrylic acid were added dropwise over 5 hours2,6]Decan-8-yl ester and acrylic acid 3, 4-epoxytricyclo [5.2.1.02,6]A mixed solution of 289 parts of a mixture of decane-9-yl esters and 125 parts of propylene glycol monomethyl ether acetate. On the other hand, a mixed solution obtained by dissolving 33 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was kept at this temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution having a solid content of 35.0%. The resulting resin B1 had a weight average molecular weight (Mw) of 8800, a dispersity of 2.1, and an acid value of the solution of 28 mg-KOH/g.
Synthesis example 2
An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and the atmosphere was replaced with nitrogen, and 371 parts of propylene glycol monomethyl ether acetate was charged and heated to 85 ℃ with stirring. Then, 54 parts of acrylic acid and 3, 4-epoxytricyclo [5.2.1.0 ] acrylic acid were added dropwise over 4 hours 2,6]Decan-8-yl ester and acrylic acid 3, 4-epoxytricyclo [5.2.1.02,6]A mixed solution of 225 parts of a mixture of decane-9-yl ester, 81 parts of vinyltoluene (isomer mixture) and 80 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution obtained by dissolving 30 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile), a polymerization initiator, in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the end of the dropwise addition of the initiator solution, the temperature was maintained for 4 hours and then cooledThe temperature was then cooled to room temperature, whereby a copolymer (resin B3) solution containing 37.5% of solid matter was obtained. The resulting resin B3 had a weight-average molecular weight (Mw) of 10600, a dispersity of 2.01, and an acid value of 43 mg-KOH/g.
Synthesis example 3
An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and the atmosphere was replaced with nitrogen, 350 parts of propylene glycol monomethyl ether acetate was charged, and the mixture was heated to 85 ℃ with stirring. Subsequently, 70 parts of acrylic acid and 3, 4-epoxytricyclo [5.2.1.0 ] acrylic acid were added dropwise over 4 hours2,6]Decane-8-yl ester or/and acrylic acid 3, 4-epoxytricyclo [5.2.1.02,6]A mixed solution of 202 parts of a mixture of decane-9-yl ester, 78 parts of vinyltoluene (isomer mixture) and 100 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution obtained by dissolving 33 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile), a polymerization initiator, in 167 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the completion of the dropwise addition of the initiator solution, the mixture was held at this temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin B5) solution having a solid content of 38.1%. The obtained resin B5 had a weight-average molecular weight (Mw) of 10400, a dispersity of 2.03 and an acid value of 53 mg-KOH/g.
Example 101Z1
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 1) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 1: 50 parts of a mixture of the compound represented by the formula (IZ1-38) obtained in example 1Z1 and the compound represented by the formula (IZ1-39),
58 parts of a dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
A mixture of the compound represented by the formula (IZ1-38) obtained in example 1Z1 and the compound represented by the formula (IZ1-39) was dispersed using a bead mill, to thereby obtain a colored composition. Next, the following were mixed to obtain colored curable composition 1Z1,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 1);
400 parts of the obtained coloring composition;
Resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A colored curable composition 1Z1 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a line and space pattern (li) having a thickness of 100 μm was used ne-and-space pattern). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z1 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored coating film was post-baked at 230 ℃ for 30 minutes, thereby obtaining a colored coating film.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation). The phase difference value at an inclination angle (angle あおり Japanese) of the colored coating film of 45 ℃ was measured using an ellipsometer (model M-220 spectroscopic ellipsometer; manufactured by Nippon corporation). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 8Z 1.
Example 102Z1
A colored curable composition 2Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ1-21) obtained in example 2Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 103Z1
A colored curable composition 3Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-2) and the compound represented by the formula (IZ1-3) obtained in example 3Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 104Z1
A colored curable composition 4Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-38) obtained in example 4Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 105Z1
A colored curable composition 5Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-20) obtained in example 5Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 106Z1
A colored curable composition 6Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-2) obtained in example 6Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 107Z1
A colored curable composition 7Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1, except that c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 108Z1
A colored curable composition 8Z1 was obtained in the same manner as in example 101Z1 and a colored pattern was obtained in the same manner as in example 101Z1, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7, and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ1-21) obtained in example 2Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 109Z1
A colored curable composition 9Z1 was obtained in the same manner as in example 101Z1 and a colored pattern was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-2) and the compound represented by the formula (IZ1-3) obtained in example 3Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 110Z1
A colored curable composition 10Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-38) obtained in example 4Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 111Z1
A colored curable composition 11Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-20) obtained in example 5Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 112Z1
A colored curable composition 12Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-2) obtained in example 6Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 113Z1
A colored curable composition 13Z1 was obtained in the same manner as in example 101Z1 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 114Z1
A colored curable composition 14Z1 was obtained in the same manner as in example 101Z1 and a colored pattern was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ1-21) obtained in example 2Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 115Z1
A colored curable composition 15Z1 was obtained in the same manner as in example 101Z1 and a colored pattern was obtained in the same manner as in example 101Z1, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59, and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-2) and the compound represented by the formula (IZ1-3) obtained in example 3Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 116Z1
A colored curable composition 16Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-38) obtained in example 4Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 117Z1
A colored curable composition 17Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-20) obtained in example 5Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 118Z1
A colored curable composition 18Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-2) obtained in example 6Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Comparative example 1Z1
A colored curable composition C1Z1 was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with c.i. pigment yellow 185, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Comparative example 2Z1
A colored curable composition C2Z1 was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with c.i. pigment green 7 and the mixture was replaced with c.i. pigment yellow 185, thereby obtaining a colored pattern, instead of c.i. pigment green 58. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Comparative example 3Z1
A colored curable composition C3Z1 was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with c.i. pigment green 58 and the mixture was replaced with c.i. pigment yellow 185, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
[ Table 8Z1]
TABLE 8Z1
Film thickness (mum) Phase difference value (nm)
Example 101Z1 2.3 3
Example 102Z1 2.3 3
Example 103Z1 2.3 4
Practice ofExample 104Z1 2.3 3
Example 105Z1 2.3 3
Example 106Z1 2.3 4
Example 107Z1 2.3 3
Example 108Z1 2.3 3
Example 109Z1 2.3 4
Example 110Z1 2.3 3
Example 111Z1 2.3 3
Example 112Z1 2.3 4
Example 113Z1 2.3 3
Example 114Z1 2.3 3
Example 115Z1 2.3 4
Example 116Z1 2.3 3
Example 117Z1 2.3 3
Example 118Z1 2.3 4
Comparative example 1Z1 2.3 15
Comparative example 2Z1 2.3 15
Comparative example 3Z1 2.3 15
Example 119Z1
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 1) was prepared by dispersing the pigment using a bead mill.
In addition, the following substances were mixed,
colorant AZ 1: 50 parts of a mixture of the compound represented by the formula (IZ1-38) obtained in example 1Z1 and the compound represented by the formula (IZ1-39),
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
A mixture of the compound represented by the formula (IZ1-38) obtained in example 1Z1 and the compound represented by the formula (IZ1-39) was dispersed using a bead mill, to thereby obtain a colored composition.
Next, the following were mixed to obtain a colored curable composition 19Z1,
The total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 1);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z1 except that a colored curable composition 19Z1 was used instead of the colored curable composition 1Z 1. A colored coating film was obtained in the same manner as in example 101Z1 except that a colored curable composition 19Z1 was used in place of the colored curable composition 1Z1, and the film thickness and the retardation value were measured. The results are shown in Table 9Z 1.
Example 120Z1 to example 127Z1
A colored pattern was obtained in the same manner as in example 119Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the colorant shown in the column of "colorant" in table 9Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 1.
Example 128Z1 to example 136Z1
A colored pattern was obtained in the same manner as in example 119Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound shown in the column of "colorant" in table 9Z1, and c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 1.
Example 137Z1 to example 145Z1
A colored pattern was obtained in the same manner as in example 119Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound shown in the column of "colorant" in table 9Z1, and c.i. pigment green 58 was replaced with c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 1.
[ Table 9Z1]
TABLE 9Z1
Figure BDA0003121580680004451
In the examination of example Z1, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Example Z2
Example 1Z2
5.02 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 22 parts of methanol were mixed. To the resulting mixture, 2.90 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) was added, and the mixture was stirred at 25 ℃ for 3 hours.
To the obtained mixture were added 3.67 parts of ethyl cyanoacetate (manufactured by Tokyo chemical industry Co., Ltd.), 1.83 parts of acetic acid and 30 parts of methanol, and the mixture was stirred at 25 ℃ for 1 hour and 30 minutes.
To the obtained mixture were added 3.62 parts of ethyl cyanoacetate (manufactured by tokyo chemical industries, ltd.), 2.37 parts of acetic acid and 30 parts of methanol, and the mixture was stirred at 63 ℃ for 3 hours.
To the obtained mixture were added 3.63 parts of ethyl cyanoacetate (manufactured by tokyo chemical industry co., ltd.), 2.36 parts of acetic acid and 30 parts of methanol, and the mixture was stirred at 63 ℃ for 2 hours.
To the obtained mixture were added 3.62 parts of ethyl cyanoacetate (manufactured by Tokyo chemical industry Co., Ltd.) and 2.40 parts of acetic acid, and the mixture was stirred at 63 ℃ for 1 hour, at room temperature for 11 hours and at 63 ℃ for 6 hours.
The temperature of the resulting mixture was lowered to room temperature, followed by filtration.
The obtained residue was dried to obtain 10.0 parts of a mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ 2-149).
Figure BDA0003121580680004461
Identification of Compound represented by the formula (IaZ2-39)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+383
Exact molecular weight (Exact masses): 382
Figure BDA0003121580680004471
Identification of Compound represented by the formula (IaZ2-38)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+355
Exact molecular weight (Exact masses): 354
Figure BDA0003121580680004472
Identification of Compound represented by the formula (IaZ2-149)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+369
Exact molecular weight (Exact masses): 368
Example 2Z2
A compound represented by formula (IbZ2-125) was obtained in the same manner as in example 1Z2, except that ethyl cyanoacetate (manufactured by tokyo chemical industry co.) was replaced with 2-cyanoacetamide (manufactured by tokyo chemical industry co.).
Figure BDA0003121580680004473
Identification of Compound represented by the formula (IbZ2-125)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+325
Exact molecular weight (Exact masses): 324
Example 3Z2
The procedure of example 1Z2 was repeated except for replacing ethyl cyanoacetate (manufactured by tokyo chemical industries, ltd.) with 2-cyano-N-methylacetamide to obtain compounds represented by the formula (IbZ 2-126).
Figure BDA0003121580680004481
Identification of Compound represented by the formula (IbZ2-126)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+353
Exact molecular weight (Exact masses): 352
Example 4Z2
A compound represented by formula (IbZ2-148) was obtained in the same manner as in example 1Z2, except that ethyl cyanoacetate (manufactured by tokyo chemical industry co.) was replaced with 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.).
Figure BDA0003121580680004482
Identification of Compound represented by the formula (IbZ2-148)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+381
Exact molecular weight (Exact masses): 380
Example 5Z2
A compound represented by formula (IbZ2-149) was obtained in the same manner as in example 1Z2, except that ethyl cyanoacetate (manufactured by tokyo chemical industry co.) was replaced with 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co.).
Figure BDA0003121580680004491
Identification of Compound represented by the formula (IbZ2-149)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+437
Exact molecular weight (Exact masses): 436
Example 6Z2
The procedure of example 1Z2 was repeated except for replacing ethyl cyanoacetate (manufactured by tokyo chemical industry co.) with 2-cyanoacetanilide (2-cyanoacetanilide) (manufactured by tokyo chemical industry co.) to obtain compounds represented by the formulae (IbZ2 to 128).
Figure BDA0003121580680004492
Identification of Compound represented by the formula (IbZ2-128)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+477
Exact molecular weight (Exact masses): 476
Example 7Z2XXX (662)
2.55 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While the mixture was kept at 5 ℃ or lower, a mixture of 1.47 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) and 30 parts of methanol was added. The mixture was stirred at 5 ℃ or below for 5 hours. To the mixture were added 2.16 parts of acetic acid, 2.92 parts of 2-cyano-N-methylacetamide and 21 parts of methanol, and the mixture was stirred at 40 ℃ for 3 hours.
To the mixture was added 13.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.), and the mixture was stirred at 40 ℃ for 12 hours and at 62 ℃ for 9 hours.
To the mixture were added 1.50 parts of 2-cyano-N-methylacetamide and 3.05 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.), and the mixture was stirred at 62 ℃ for 5 hours and at 40 ℃ for 17 hours. In addition, up to this point in time, 6 parts in total of methanol were added in addition to the above-mentioned methanol. After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-126).
Figure BDA0003121580680004501
Identification of Compound represented by the formula (IbZ2-126)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+353
Exact molecular weight (Exact masses): 352
Example 8Z2
10 parts of 4-nitrophthalonitrile and 80 parts of methanol are mixed.
While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 4-nitrophthalonitrile 10 parts was added. The mixture was stirred at 0 ℃ for 5 hours.
To the mixture were added 16 parts of acetic acid and 2-cyanoacetamide in an amount of 3.3 times the molar amount of 10 parts of 4-nitrophthalonitrile, and the mixture was stirred at 60 ℃ for 21 days.
After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-125).
Figure BDA0003121580680004511
Identification of Compound represented by the formula (IbZ2-125)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+325
Exact molecular weight (Exact masses): 324
Example 9Z2
10 parts of 4-nitrophthalonitrile and 80 parts of methanol are mixed.
While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 4-nitrophthalonitrile 10 parts was added. The mixture was stirred at 0 ℃ for 5 hours.
To the mixture were added 16 parts of acetic acid and 2-cyano-N, N-dimethylacetamide in an amount of 3.3 times the number of moles of 10 parts of 4-nitrophthalonitrile, and the mixture was stirred at 60 ℃ for 21 days. After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-148).
Figure BDA0003121580680004512
Identification of Compound represented by the formula (IbZ2-148)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+381
Exact molecular weight (Exact masses): 380
Example 10Z2
10 parts of 4-nitrophthalonitrile and 80 parts of methanol are mixed. While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 4-nitrophthalonitrile 10 parts was added. The mixture was stirred at 0 ℃ for 5 hours. To the mixture were added 16 parts of acetic acid and 2-cyano-N, N-diethylacetamide in an amount of 3.3 times the number of moles of 10 parts of 4-nitrophthalonitrile, and the mixture was stirred at 60 ℃ for 21 days.
After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-149).
Figure BDA0003121580680004521
Identification of Compound represented by the formula (IbZ2-149)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+437
Exact molecular weight (Exact masses): 436
Example 11Z2XXX (660)
1.25 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 41 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 0.722 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 19 parts of methanol was added dropwise to the obtained mixture over 5 minutes. The resulting mixture was stirred for 4 hours while being kept at 5 ℃ or lower.
While the resulting mixture was kept at 5 ℃ or lower, 1.21 parts of acetic acid, 2.33 parts of 2-cyanoacetanilide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 18 parts of methanol were added. The resulting mixture was stirred at 40 ℃ for 21 hours. To the obtained mixture were added 0.596 parts of acetic acid, 1.17 parts of 2-cyanoacetanilide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 17 parts of methanol. The resulting mixture was stirred at 40 ℃ for 3 hours. To the resulting mixture, 2.09 parts of acetic acid was added, and stirring was performed at 50 ℃ for 2 hours, at 60 ℃ for 2 hours, at room temperature for 15 hours, and at 62 ℃ for 3 hours.
To the resulting mixture, 0.981 part of trifluoroacetic acid was added, and stirring was performed at 62 ℃ for 2 hours.
To the resulting mixture, 11.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added, and the mixture was stirred at 62 ℃ for 2 hours, at room temperature for 14 hours, and at 62 ℃ for 5 hours. In addition, 10 parts in total of methanol other than the above-mentioned methanol was added up to this point. The resulting mixture was cooled to 23 ℃ and added to 1100 parts of 50% aqueous acetic acid.
To the resulting mixture, 40 parts of methanol and 400 parts of 50% aqueous acetic acid were added.
The resulting mixture was filtered, and the resulting residue was washed 6 times with 250 parts of 50% aqueous acetic acid solution and 3 times with 250 parts of water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 3.32 parts of a compound represented by the formula (IbZ 2-128).
Figure BDA0003121580680004531
Identification of Compound represented by the formula (IbZ2-128)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+477
Exact molecular weight (Exact masses): 476
Example 12Z2XXX (653)
25.2 parts of 4-tert-butylphthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 212 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 20.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 184 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the resulting mixture, 13.7 parts of acetic acid and 13.5 parts of 2-cyano-N-methylacetamide were added at 10 to 20 ℃. The obtained mixture was stirred at 10 to 20 ℃ for 5 hours and then at 40 ℃ for 16 hours. To the resulting mixture, 6.79 parts of acetic acid and 6.75 parts of 2-cyano-N-methylacetamide were added, and stirring was performed at 40 ℃ for 6 hours and at 50 ℃ for 65 hours. In addition, a total of 201 parts of methanol was added up to this time point, in addition to the above-mentioned methanol. To the resulting mixture were added 13.5 parts of acetic acid, 18.3 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 604 parts of water, and the mixture was stirred at 40 ℃ for 53 hours.
The resulting mixture was filtered, and the residue was washed with 50% aqueous methanol. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-64).
Figure BDA0003121580680004541
Identification of Compound represented by the formula (IbZ2-64)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+364
Exact molecular weight (Exact masses): 363
Example 13Z2XXX (659)
25.9 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 513 parts of methanol were mixed. 30.3 parts of a 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) and 12 parts of methanol were added dropwise to the obtained mixture over 10 minutes while maintaining the temperature at 3 to 5 ℃. The resulting mixture was stirred for 6 hours while being maintained at 3 to 5 ℃.
To the obtained mixture were added 19.8 parts of acetic acid, 28.5 parts of t-butyl cyanoacetate and 26 parts of methanol while maintaining the temperature at 3 to 5 ℃. The resulting mixture was stirred at room temperature for 2 days, and then at 40 ℃ for 3 hours. To the resulting mixture were added 5.09 parts of acetic acid and 7.17 parts of tert-butyl cyanoacetate, and the mixture was stirred at 40 ℃ for 4 hours.
To the resulting mixture were added 4.95 parts of acetic acid, 7.15 parts of tert-butyl cyanoacetate and 38 parts of methanol, and the mixture was stirred at 40 ℃ for 16 hours. To the resulting mixture were added 19.9 parts of acetic acid, 25.8 parts of barbituric acid, 209 parts of methanol, and 800 parts of water, and the mixture was stirred at 40 ℃ for 3 hours. The resulting mixture was filtered to give a residue. The residue was purified by column chromatography to give a compound represented by the formula (IaZ 2-5).
Figure BDA0003121580680004551
Identification of Compound represented by the formula (IaZ2-5)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+394
Exact molecular weight (Exact masses): 393
Example 14Z2XXX (661)
15.1 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 284 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.81 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 18 parts of methanol was added dropwise to the obtained mixture over 10 minutes. The resulting mixture was stirred for 4 hours while being kept at 5 ℃ or lower. To the obtained mixture, 5.55 parts of acetic acid was added while keeping the temperature at 5 ℃ or lower, and the mixture was stirred for 30 minutes. This mixture was mixed with 12.3 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 14 hours.
This mixture was mixed with 0.654 parts of acetic acid and 1.24 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 4 hours. This mixture was mixed with 0.613 part of acetic acid and 1.23 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 3 hours. This mixture was mixed with 0.647 parts of acetic acid and 1.24 parts of t-butyl cyanoacetate. Further, up to this point, a total of 89 parts of methanol was added in addition to the above-mentioned methanol. The mixture was stirred at 40 ℃ for 17 hours. This mixture was mixed with 7.14 parts of acetic acid, 11.3 parts of barbituric acid and 508 parts of water. In addition, up to this point in time, 117 parts in total of methanol were added in addition to the above-mentioned methanol. The mixture was stirred at 40 ℃ for 24 hours. This mixture was mixed with 3.65 parts of acetic acid and 5.61 parts of barbituric acid, and stirred at 40 ℃ for 9 hours and at room temperature for 2 days. The mixture was filtered and the residue was washed 3 times with 1330 parts of 50% aqueous methanol solution. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IaZ 1-41).
Figure BDA0003121580680004561
Identification of Compound represented by the formula (IaZ1-41)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H ]+439
Exact molecular weight (Exact masses): 438
Example 15Z2XXX (520)
5.41 parts of 3,4,5, 6-tetrafluorophthalonitrile and 23.6 parts of methanol were mixed. To the mixture was added a mixture of 2.70 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) and 10 parts of methanol at 20 to 25 ℃.
The mixture was stirred at 20 to 25 ℃ for 4 hours and 20 minutes. To the mixture were added 3.36 parts of acetic acid, 5.99 parts of methyl cyanoacetate, and 7.5 parts of methanol. The mixture was stirred at 63 ℃ for 2 hours. The solvent was distilled off from the obtained mixture by a rotary evaporator, and the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IaZ 2-223).
Figure BDA0003121580680004562
Identification of Compound represented by the formula (IaZ2-223)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+382
Exact molecular weight (Exact masses): 381
Example 16Z2XXX (538)
2.52 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 22.8 parts of methanol were mixed. To the mixture was added 1.98 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) at room temperature. The mixture was stirred at 38 ℃ for 3 hours.
To the mixture were added 2.79 parts of cyanoacetylurea (manufactured by tokyo chemical industries, ltd.) and 1.26 parts of acetic acid. The mixture was stirred at 40 ℃ for 1 hour and 30 minutes.
To the mixture were added 2.77 parts of cyanoacetylurea (manufactured by tokyo chemical industries, ltd.) and 1.61 parts of acetic acid. In addition, a total of 39.2 parts of methanol was added up to this time point, in addition to the above-mentioned methanol. The mixture was stirred at 40 ℃ for 1 hour. To the mixture was added 65.2 parts of water, and the mixture was stirred at 40 ℃ for 2 hours and 30 minutes. To the mixture were added 2.80 parts of cyanoacetylurea (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 1.60 parts of acetic acid, and the mixture was stirred at 40 ℃ for 20 hours. In addition, up to this point in time, a total of 31 parts of methanol was added in addition to the above-mentioned methanol. After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-19).
Figure BDA0003121580680004571
Identification of Compound represented by the formula (IbZ2-19)
(Mass Spectrometry) ionization mode ESI +: m-z=[M+H]+366
Exact molecular weight (Exact masses): 365
Example 17Z2
8 parts of phthalonitrile and 63 parts of ethanol are mixed.
To the mixture was added a 21% sodium ethoxide ethanol solution containing sodium ethoxide in a molar amount 1 times that of 8 parts of phthalonitrile. The mixture was stirred at room temperature for 2 hours. To the mixture were added 25 parts of acetic acid and a compound represented by the formula (ppp1) in an amount of 2.3 times the mole number of 8 parts of phthalonitrile, and the mixture was stirred at 90 ℃ for 64 hours.
The mixture was cooled to room temperature and filtered. The obtained residue was washed with 160 parts of methanol and dried. The obtained residue 24 parts and N, N-dimethylformamide 230 parts were mixed.
To the mixture was added 210 parts of acetic acid. The mixture was filtered.
The obtained residue was washed with 79 parts of methanol and dried to obtain 17 parts of a compound represented by the formula (IbZ 2-311).
Figure BDA0003121580680004581
Identification of Compound represented by the formula (IbZ2-311)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+508
Exact molecular weight (Exact masses): 507
To 15 parts of the compound represented by the formula (IbZ2-311), 200 parts of methylene chloride and 150 parts of trifluoroacetic acid were added, and the mixture was stirred at room temperature for 50 hours.
To the resulting mixture was added 160 parts of methanol, followed by filtration.
The obtained residue was dried to obtain 13 parts of a residue.
The residue 12 parts and N, N-dimethylformamide 230 parts were mixed, stirred for 1 hour, and then filtered. The obtained residue was mixed with 160 parts of methanol and stirred at 70 ℃.
The resulting mixture was filtered. The residue was dried to obtain 9 parts of a compound represented by the formula (IbZ 2-317).
Figure BDA0003121580680004582
Identification of Compound represented by the formula (IbZ2-317)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-394
Exact molecular weight (Exact masses): 395
Example 18Z2
5 parts of 4-nitrophthalonitrile and 39 parts of ethanol are mixed.
While the mixture was kept at 0 ℃, a 21% sodium ethoxide ethanol solution containing sodium ethoxide in an amount of 0.5 times the mole of 5 parts of 4-nitrophthalonitrile was added. The mixture was stirred at 0 ℃ for 3 hours. To the mixture were added 16 parts of acetic acid and a compound represented by the formula (ppp1) in a molar amount of 3.3 times that of 5 parts of 4-nitrophthalonitrile. The mixture was sealed in a tube and stirred at 90 ℃ for 56 hours. The mixture was cooled to room temperature and filtered. The residue was washed with ethanol to give residue A8 parts. 10 parts of 4-nitrophthalonitrile and 79 parts of ethanol are mixed. While the mixture was kept at 0 ℃, a 21% sodium ethoxide ethanol solution containing sodium ethoxide in an amount of 0.5 times the mole number of 10 parts of 4-nitrophthalonitrile was added. The mixture was stirred at 0 ℃ for 3 hours. To the mixture were added 31 parts of acetic acid and a compound represented by the formula (ppp1) in a molar amount of 3.3 times that of 10 parts of 4-nitrophthalonitrile. The mixture was sealed in a tube and stirred at 90 ℃ for 56 hours. The mixture was cooled to room temperature and filtered. The obtained residue was washed with ethanol to obtain 15 parts of a residue B. The residue A4 parts and the residue B14 parts were mixed together with 170 parts of N, N-dimethylformamide.
The mixture was mixed with 710 parts of methanol and stirred at room temperature for 16 hours.
The mixture was filtered to obtain 13 parts of a residue containing the compound represented by the formula (IbZ 2-312).
Figure BDA0003121580680004591
Identification of Compound represented by the formula (IbZ2-312)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+553
Exact molecular weight (Exact masses): 552
The residue containing the compound represented by the formula (IbZ2-312) (13 parts) was mixed with dichloromethane (170 parts) and trifluoroacetic acid (130 parts) and stirred at room temperature for 16 hours.
To the mixture, the solvent was distilled off, 190 parts of N, N-dimethylformamide was added to 12 parts of the obtained residue, and the mixture was stirred at 90 ℃ for 10 minutes and then filtered. The resulting filtrate was allowed to stand at room temperature for 16 hours. The filtrate was filtered to obtain 8.0 parts of a residue. This residue 8.0 parts and tetrahydrofuran 22 parts were mixed, stirred at 70 ℃ for 3 hours, and then filtered.
The obtained residue 7.2 parts and acetic acid 21 parts were mixed, stirred at 80 ℃ for 2 hours, and then filtered.
The obtained residue 6.2 parts and toluene 170 parts were mixed, stirred at 95 ℃ for 3 hours, and then filtered.
The obtained residue 5.6 parts and water 50 parts were mixed, stirred at 90 ℃ for 16 hours, and then filtered.
The obtained residue was dried to obtain 5.4 parts of a compound represented by the formula (IbZ 2-515).
Figure BDA0003121580680004601
Identification of Compound represented by the formula (IbZ2-515)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-439
Exact molecular weight (Exact masses): 440
Example 19Z2
2 parts of phthalonitrile and 16 parts of methanol are mixed.
While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of phthalonitrile 2 parts was added.
The mixture was stirred at 0 ℃ for 5 hours. To the mixture were added 4.2 parts by mole of a compound represented by the formula (ppp2) in an amount of 3.3 times the mole of 2 parts by mole of phthalonitrile, and the mixture was stirred at 60 ℃ for 6 days. The mixture was cooled to room temperature and filtered. The obtained residue was washed with methanol to obtain 4 parts of a residue Aa containing the compound represented by the formula (IbZ 2-313). 8 parts of phthalonitrile and 63 parts of methanol are mixed. While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the mole of 8 parts of phthalonitrile was added. The mixture was stirred at 0 ℃ for 5 hours. To the mixture were added 17 parts of acetic acid and a compound represented by the formula (ppp2) in an amount of 3.3 times the number of moles of 8 parts of phthalonitrile, and the mixture was stirred at 60 ℃ for 10 days.
The mixture was cooled to room temperature and filtered. The obtained residue was washed with methanol to obtain 16 parts of a residue Bb containing the compound represented by formula (IbZ 2-313).
Figure BDA0003121580680004611
Identification of Compound represented by the formula (IbZ2-313)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+536
Exact molecular weight (Exact masses): 535
The residue Aa 2 parts containing the compound represented by the formula (IbZ2-313) was mixed with 27 parts of methylene chloride and 22 parts of trifluoroacetic acid, and stirred at room temperature for 16 hours. The solvent of the mixture was distilled off to obtain a residue Aaa 2 parts. The residue Aa 2 parts containing the compound represented by the formula (IbZ2-313), the residue Bb 16 parts containing the compound represented by the formula (IbZ2-313), 240 parts of methylene chloride and 190 parts of trifluoroacetic acid were mixed and stirred at room temperature for 16 hours.
The solvent of the mixture was distilled off to obtain 16 parts of residue Ccc.
1.7 parts of residue Aaa, 16 parts of residue Ccc and 210 parts of acetic acid were mixed and stirred at 80 ℃ for 16 hours. The mixture was filtered to obtain 13 parts of a residue. The residue was mixed with 71 parts of diethyl ether and stirred at room temperature for 16 hours. The mixture was filtered, and the obtained residue was dried to obtain 12 parts of a compound represented by the formula (IbZ 2-318).
Figure BDA0003121580680004612
Identification of Compound represented by the formula (IbZ2-318)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-422
Exact molecular weight (Exact masses): 423
Example 20Z2
2 parts of 4-nitrophthalonitrile and 16 parts of methanol are mixed.
While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 4-nitrophthalonitrile 2 parts was added. The mixture was stirred at 0 ℃ for 3 hours. To the mixture were added 2.1 parts by mole of a compound represented by the formula (ppp2) 3.3 times the mole of 2 parts by mole of 4-nitrophthalonitrile and 2.1 parts by mole of acetic acid, and the mixture was stirred at 60 ℃ for 15 days. The mixture was cooled to room temperature and filtered. The obtained residue was washed with 48 parts of methanol to obtain 8.4 parts of a residue containing the compound represented by the formula (IbZ 2-314).
Figure BDA0003121580680004621
Identification of Compound represented by the formula (IbZ2-314)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+581
Exact molecular weight (Exact masses): 580
The residue containing the compound represented by the formula (IbZ2-314) (8.4 parts) was mixed with dichloromethane (110 parts) and trifluoroacetic acid (89 parts) and stirred at room temperature for 16 hours. The solvent of the mixture was distilled off to obtain 6.9 parts of a residue. This residue 6.1 parts and 34 parts of dimethyl sulfoxide were mixed and stirred at room temperature for 5 minutes. The mixture was mixed with 190 parts of acetic acid, and stirred at room temperature for 30 minutes. The mixture was mixed with 290 parts of methanol and stirred at room temperature for 1 hour. The mixture was filtered to give a residue of 5.7 parts. The residue 5.6 parts and water 150 parts were mixed, stirred at 80 ℃ for 2 hours, and filtered.
The obtained residue was dried to obtain 5.4 parts of a compound represented by the formula (IbZ 2-516).
Figure BDA0003121580680004631
< identification of Compound represented by formula (IbZ2-516 >
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-467
Exact molecular weight (Exact masses): 468
Example 21Z2
A compound represented by the formula (ppp3) in an amount of 1.1 times the mole of 6 parts of phthalonitrile, 66 parts of dimethyl sulfoxide and 1 time the mole of potassium tert-butoxide in an amount of 6 parts of phthalonitrile were mixed and stirred at room temperature for 10 minutes. To the mixture was added 6 parts of phthalonitrile, and the mixture was stirred at 80 ℃ for 2 hours. To the mixture was added a compound represented by the formula (ppp3) in an amount of 1.1 times the mole of 6 parts of phthalonitrile, and the mixture was stirred at 180 ℃ for 2 hours. The mixture was cooled to room temperature and filtered to obtain 5.3 parts of a residue. This residue 5.0 parts was mixed with 55 parts of dimethyl sulfoxide and 47 parts of N, N-dimethylformamide, and stirred at 80 ℃ for 30 minutes.
This mixture was mixed with 240 parts of methanol and stirred at 80 ℃ for 30 minutes.
The mixture was cooled to room temperature and filtered. The obtained residue was mixed with 55 parts of dimethyl sulfoxide and 47 parts of N, N-dimethylformamide, and stirred at 80 ℃ for 30 minutes. This mixture was mixed with 240 parts of methanol and stirred at 80 ℃ for 30 minutes. The mixture was cooled to room temperature and filtered to obtain 4.6 parts of a residue. The residue was mixed with methanol and stirred at 80 ℃ for 2 hours. The mixture was filtered, and the obtained residue was dried to obtain 4.5 parts of a compound represented by the formula (IbZ 2-319).
Figure BDA0003121580680004632
Identification of Compound represented by the formula (IbZ2-319)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-518
Exact molecular weight (Exact masses): 519
Example 22Z2
50 parts of 4-aminomethylbenzoic acid, cyanoacetic acid in an amount of 1.2 times the molar amount of 50 parts of 4-aminomethylbenzoic acid, N' -dicyclohexylcarbodiimide in an amount of 0.9 times the molar amount of 50 parts of 4-aminomethylbenzoic acid, and 890 parts of tetrahydrofuran were mixed and stirred at room temperature for 16 hours. The mixture was filtered, and the solvent of the filtrate was distilled off to obtain a residue.
The obtained residue was mixed with 270 parts of ethyl acetate and filtered.
The obtained residue was dried to obtain 30 parts of a compound represented by the formula (ppp 4).
Figure BDA0003121580680004641
Identification of Compound represented by the formula (ppp4)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-217
Exact molecular weight (Exact masses): 218
In addition, 3 parts of phthalonitrile and 110 parts of ethylene glycol were mixed. To the mixture was added 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 1.5 times the mole of 3 parts of phthalonitrile at room temperature.
The mixture was stirred at room temperature for 4 hours. To the mixture were added 110 parts of a compound represented by the formula (ppp4) in an amount of 3.1 times the mole of 3 parts of phthalonitrile and 110 parts of ethylene glycol, and the mixture was stirred at 110 ℃ for 16 hours. After the mixture was cooled to room temperature, 630 parts of methanol was added. The mixture was mixed with 26 parts of acetic acid. The mixture was filtered to obtain 11 parts of a residue. The residue was mixed with 220 parts of dimethyl sulfoxide. This mixture was mixed with 630 parts of methanol. The mixture was filtered to give a residue of 9.5 parts. The residue was mixed with 220 parts of dimethyl sulfoxide. This mixture was mixed with 630 parts of methanol. The mixture was filtered to obtain 9 parts of a residue. The residue was mixed with 200 parts of water and stirred at 80 ℃ for 2 hours. The mixture was mixed with 2.1 parts of acetic acid. The mixture was filtered to give 8.5 parts of a residue. The residue (8.1 parts) and dimethyl sulfoxide (260 parts) were mixed and stirred at 60 ℃ for 20 minutes. The mixture was cooled to room temperature, allowed to stand at room temperature for 2 hours, and filtered.
The obtained residue was washed with 2% aqueous acetic acid solution to obtain 6.2 parts of a residue. The residue was mixed with 150 parts of water and stirred at 80 ℃ for 30 minutes. The mixture was cooled to room temperature and filtered.
The obtained residue was washed with 200 parts of water. The residue was dried to obtain 6 parts of a compound represented by the formula (IbZ 2-320).
Figure BDA0003121580680004651
Identification of Compound represented by the formula (IbZ2-320)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-546
Exact molecular weight (Exact masses): 547
Example 23Z2
5 parts of 4, 5-dibromophthalonitrile and 93 parts of 2-ethoxyethanol are mixed.
To the mixture was added a 25% sodium methoxide methanol solution containing 1 time by mole of sodium methoxide as much as 5 parts by mole of 4, 5-dibromophthalonitrile. The mixture was stirred at room temperature for 6 hours. To the mixture was added a compound represented by the formula (ppp1) in an amount of 6 times the mole number of 5 parts of 4, 5-dibromophthalonitrile, and the mixture was stirred at 90 ℃ for 65 hours and then at 100 ℃ for 10 hours. This mixture was mixed with 300 parts of water and 21 parts of acetic acid. The mixture was filtered to obtain 10 parts of a residue. The residue was mixed with 120 parts of methanol and 10 parts of acetic acid. The mixture was filtered to obtain 5.5 parts of a residue containing the compound represented by the formula (IbZ 2-315).
Figure BDA0003121580680004652
Identification of Compound represented by the formula (IbZ2-315)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+664
Exact molecular weight (Exact masses): 663
The residue containing the compound represented by the formula (IbZ2-315) (5.5 parts) was mixed with trifluoroacetic acid (45 parts) and dichloromethane (80 parts), and stirred at room temperature for 16 hours. The solvent of the mixture was distilled off to obtain 6 parts of a residue. The residue was mixed with 79 parts of methanol. The mixture was filtered to obtain 4 parts of a residue.
This residue was mixed with 0.24 part of lithium hydroxide, 36 parts of tetrahydrofuran and 12 parts of water, and stirred at room temperature for 6 hours. Tetrahydrofuran was distilled off from the mixture using an evaporator. To the resulting mixture, water and 1.5N hydrochloric acid were added. The mixture was filtered to give a residue of 3.5 parts. The residue was mixed with 40 parts of methanol. The mixture was filtered, and the residue was washed with 13 parts of hexane to give 3 parts of residue. This residue 2.8 parts and dimethyl sulfoxide 33 parts were mixed and stirred at 70 ℃ for 20 minutes. The mixture was cooled to room temperature and filtered.
The obtained residue was washed with 40 parts of methanol and then 50 parts of water.
The residue was dried to obtain 1.8 parts of a compound represented by the formula (IbZ 2-706).
Figure BDA0003121580680004661
Identification of Compound represented by the formula (IbZ2-706)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-550
Exact molecular weight (Exact masses): 551
Example 24Z2
13 parts of 4, 5-dichlorophthalonitrile and 160 parts of methanol were mixed.
While the mixture was kept at 0 ℃ a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the mole number of 13 parts by mole of 4, 5-dichlorophthalonitrile was added. The mixture was stirred at 0 ℃ for 5 hours. To the mixture were added a compound represented by the formula (ppp1) in an amount of 4.4 times the mole number of 13 parts of 4, 5-dichlorophthalonitrile and 16 parts of acetic acid, and the mixture was stirred at 75 ℃ for 7 days. To the mixture were added 14 parts of acetic acid and a compound represented by the formula (ppp1) in an amount of 3 times the mole number of 13 parts of 4, 5-dichlorophthalonitrile, and the mixture was stirred at 75 ℃ for 11 days.
The mixture was filtered. The obtained residue was washed with 320 parts of methanol to obtain 26 parts of a residue.
13 parts of this residue was mixed with 100 parts of methanol, 16 parts of acetic acid and 26.3 parts of a compound represented by the formula (ppp1), and stirred at 75 ℃ for 48 hours. The mixture was filtered. The obtained residue was washed with 40 parts of methanol to obtain 12 parts of a residue containing the compound represented by the formula (IbZ 2-316).
Figure BDA0003121580680004671
Identification of Compound represented by the formula (IbZ2-316)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+576
Exact molecular weight (Exact masses): 575
The residue containing the compound represented by the formula (IbZ2-316) (12 parts) was mixed with dichloromethane (160 parts) and trifluoroacetic acid (130 parts), and the mixture was stirred at room temperature for 16 hours. The mixture was filtered to obtain 6.2 parts of a residue. The residue was mixed with 73 parts of acetic acid and stirred at 80 ℃ for 2 hours. The mixture was filtered to give 5.3 parts of a residue. The residue was mixed with 60 parts of water and stirred at 80 ℃ for 2 hours. The mixture was filtered, and the obtained residue was dried to obtain 5 parts of a compound represented by the formula (IbZ 2-389).
Figure BDA0003121580680004672
Identification of Compound represented by the formula (IbZ2-389)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-462
Exact molecular weight (Exact masses): 463
Example 101Z2
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 2) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
Colorant AZ 2: 50 parts of a mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2,
58 parts of a dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
A mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was dispersed using a bead mill to obtain a coloring composition.
Next, the following were mixed to obtain colored curable composition 1Z2,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 2);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A2-inch square glass substrate (EAGLE XG; manufactured by Corning Inc.) was coated with a colored curable composition 1Z2 by spin coating, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a photomask in which a line-and-space pattern of 100 μm was formed was used. The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z2 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, thereby obtaining a colored coating film.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation). The phase difference value at an inclination angle of 45 ° of the colored coating film was measured using an ellipsometer (M-220 type spectroscopic ellipsometer; manufactured by japan spectro (ltd.)). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 23Z 2.
Example 102Z2
A colored curable composition 2Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by the formula (IbZ2-125) obtained in example 2Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 103Z2
A colored curable composition 3Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by the formula (IbZ2-126) obtained in example 3Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 104Z2
A colored curable composition 4Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by the formula (IbZ2-148) obtained in example 4Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 105Z2
A colored curable composition 5Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by the formula (IbZ2-149) obtained in example 5Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 106Z2
A colored curable composition 6Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by the formula (IbZ2-128) obtained in example 6Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 107Z2
A colored curable composition 7Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2, except that c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 108Z2
A colored curable composition 8Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-125) obtained in example 2Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 109Z2
A colored curable composition 9Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-126) obtained in example 3Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 110Z2
A colored curable composition 10Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-148) obtained in example 4Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 111Z2
A colored curable composition 11Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-149) obtained in example 5Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 112Z2
A colored curable composition 12Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-128) obtained in example 6Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 113Z2
A colored curable composition 13Z2 was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 114Z2
A colored curable composition 14Z2 was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38), and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-125) obtained in example 2Z2, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 115Z2
A colored curable composition 15Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-126) obtained in example 3Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 116Z2
A colored curable composition 16Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-148) obtained in example 4Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 117Z2
A colored curable composition 17Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-149) obtained in example 5Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 118Z2
A colored curable composition 18Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-128) obtained in example 6Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Comparative example 1Z2
A colored curable composition C1Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Comparative example 2Z2
A colored curable composition C2Z2 was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7, and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38), and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with c.i. pigment yellow 185, to obtain a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Comparative example 3Z2
A colored curable composition C3Z2 was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38), and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with c.i. pigment yellow 185, to obtain a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
[ Table 23Z2]
TABLE 23Z2
Film thickness (mum) Phase difference value (nm)
Example 101Z2 2.3 3
Example 102Z2 2.3 4
Example 103Z2 2.3 3
Example 104Z2 2.3 3
Example 105Z2 2.3 3
Example 106Z2 2.3 3
Example 107Z2 2.3 3
Example 108Z2 2.3 3
Example 109Z2 2.3 3
Practice ofExample 110Z2 2.3 3
Example 111Z2 2.3 4
Example 112Z2 2.3 3
Example 113Z2 2.3 3
Example 114Z2 2.3 3
Example 115Z2 2.3 3
Example 116Z2 2.3 3
Example 117Z2 2.3 3
Example 118Z2 2.3 3
Comparative example 1Z2 2.3 15
Comparative example 2Z2 2.3 15
Comparative example 3Z2 2.3 15
Example 119Z2
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 2) was prepared by dispersing the pigment using a bead mill.
In addition, the following substances were mixed,
colorant AZ 2: 50 parts of a mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2,
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
A mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was dispersed using a bead mill to obtain a coloring composition.
Next, the following were mixed to obtain a colored curable composition 19Z2,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 2);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
Polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z2 except that a colored curable composition 19Z2 was used instead of the colored curable composition 1Z 2. A colored coating film was obtained in the same manner as in example 101Z2 except that a colored curable composition 19Z2 was used in place of the colored curable composition 1Z2, and the film thickness and the retardation value were measured. The results are shown in Table 24Z 2.
Example 120Z2 to example 138Z2
A colored pattern was obtained in the same manner as in example 119Z2, except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38), and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the colorant shown in the column of "colorant" in table 24Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 24Z 2.
Example 139Z2 to example 158Z2
A colored pattern was obtained in the same manner as in example 119Z2, except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38), and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound shown in the column of "colorant" in table 24Z2, and c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 25Z 2.
Example 159Z2 to example 178Z2
A colored pattern was obtained in the same manner as in example 119Z2, except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38), and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound shown in the column of "colorant" in table 24Z2, and c.i. pigment green 58 was replaced with c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 26Z 2.
[ Table 24Z2]
TABLE 24Z2
Figure BDA0003121580680004781
[ Table 25Z2]
TABLE 25Z2
Figure BDA0003121580680004782
[ Table 26Z2]
TABLE 26Z2
Figure BDA0003121580680004791
Chemical formulas of compounds represented by formula (IaZ2-1) in tables 24Z2, 25Z2, and 26Z2 are shown.
Figure BDA0003121580680004792
In the examination of example Z2, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Example Z3
Example 1Z3
10.3 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 44.8 parts of methanol were mixed. While keeping the temperature at 20 to 25 ℃, 8.01 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture.
The resulting mixture was stirred at 20 to 25 ℃ for 2 hours.
10 parts of methanol was added to the obtained mixture while keeping the temperature at 20 to 25 ℃.
The resulting mixture was stirred at 20-25 ℃ for 2 hours.
To the obtained mixture, 7.49 parts of 2-cyanoacetamide (manufactured by tokyo chemical industries, Ltd.) and 4.98 parts of acetic acid were added, and the obtained mixture was stirred at 40 ℃ for 2 hours and at 65 ℃ for 2 hours.
To the obtained mixture were added 11.3 parts of barbituric acid (manufactured by tokyo chemical industry corporation), 6.53 parts of acetic acid, and 160 parts of water, and the obtained mixture was stirred at 65 ℃ for 3 hours, at room temperature for 2 days, and at 75 ℃ for 5 hours.
To the resulting mixture was added 230 parts of methanol at room temperature.
The obtained compound was filtered, and the obtained residue was washed with 170 parts of methanol 1 time, 400 parts of methanol 2 times, 1000 parts of water 1 time, and 200 parts of methanol 11 times.
To the resulting residue was added 641 parts of a 5% aqueous sodium hydroxide solution, and the mixture was stirred at room temperature.
The resulting mixture was filtered, and the resulting residue was washed with 1000 parts of water.
To the resulting residue was added 478 parts of water, followed by stirring at room temperature.
The resulting mixture was filtered, and the resulting residue was washed with 500 parts of water.
The obtained residue was dried to obtain 19.1 parts of a compound represented by the formula (IZ 3-1).
Figure BDA0003121580680004801
Identification of Compound represented by the formula (IZ3-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+324
Exact molecular weight (Exact masses): 323
Example 2Z3
The procedure of example 1Z3 was repeated except for replacing phthalonitrile (manufactured by tokyo chemical industry co.) with 4-nitrophthalonitrile (manufactured by tokyo chemical industry co.) to obtain a compound represented by the formula (IZ 3-19).
Figure BDA0003121580680004811
Identification of Compound represented by the formula (IZ3-19)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+369
Exact molecular weight (Exact masses): 368
Example 3Z3
A compound represented by the formula (IZ3-6) was obtained in the same manner as in example 1Z3, except that phthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.).
Figure BDA0003121580680004812
Identification of Compound represented by the formula (IZ3-6)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+380
Exact molecular weight (Exact masses): 379
Example 4Z3XXX (516)
10.3 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 44.8 parts of methanol were mixed.
While keeping the temperature at 20 to 25 ℃, 8.01 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture.
The resulting mixture was stirred at 20 to 25 ℃ for 2 hours.
10 parts of methanol was added to the obtained mixture while keeping the temperature at 20 to 25 ℃.
The resulting mixture was stirred at 20-25 ℃ for 2 hours.
To the obtained mixture, 7.49 parts of 2-cyanoacetamide (manufactured by tokyo chemical industries, Ltd.) and 4.98 parts of acetic acid were added, and the obtained mixture was stirred at 40 ℃ for 2 hours and at 65 ℃ for 2 hours.
To the obtained mixture were added 11.3 parts of barbituric acid (manufactured by tokyo chemical industry corporation), 6.53 parts of acetic acid, and 160 parts of water, and the obtained mixture was stirred at 65 ℃ for 3 hours, at room temperature for 2 days, and at 75 ℃ for 5 hours.
To the resulting mixture was added 230 parts of methanol at room temperature.
The obtained compound was filtered, and the obtained residue was washed with 170 parts of methanol 1 time, 400 parts of methanol 2 times, 1000 parts of water 1 time, and 200 parts of methanol 11 times.
To the resulting residue was added 641 parts of a 5% aqueous sodium hydroxide solution, and the mixture was stirred at room temperature.
The resulting mixture was filtered, and the resulting residue was washed with 1000 parts of water.
To the resulting residue was added 478 parts of water, followed by stirring at room temperature.
The resulting mixture was filtered, and the resulting residue was washed with 500 parts of water.
The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 3-1).
Figure BDA0003121580680004821
Identification of Compound represented by the formula (IZ3-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+324
Exact molecular weight (Exact masses): 323
Example 5Z3XXX
10.0 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 149 parts of methanol were mixed. While keeping the temperature at 2 to 6 ℃, 5.86 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture over 20 minutes. The resulting mixture was stirred for 5 hours while being kept at 5 ℃ or lower. While the resulting mixture was kept at 5 ℃ or lower, 5.79 parts of acetic acid, 4.86 parts of 2-cyanoacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65 ℃ for 3 days.
To the obtained mixture were added 2.88 parts of acetic acid and 2.43 parts of 2-cyanoacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.). The resulting mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 140 parts of methanol was added in addition to the above-mentioned methanol.
To the obtained mixture were added 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days.
The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to give a compound represented by the formula (IZ 3-19).
Figure BDA0003121580680004831
Identification of Compound represented by the formula (IZ3-19)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+369
Exact molecular weight (Exact masses): 368
Example 6Z3XXX
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the obtained mixture, 5.42 parts of acetic acid and 4.56 parts of 2-cyanoacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days.
To the obtained mixture were added 2.69 parts of acetic acid and 2.28 parts of 2-cyanoacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days.
The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to give a compound represented by the formula (IZ 3-6).
Figure BDA0003121580680004841
Identification of Compound represented by the formula (IZ3-6)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+380
Exact molecular weight (Exact masses): 379
Example 7Z3
5.0 parts of 4, 5-dichlorophthalonitrile and 62 parts of methanol were mixed. While the mixture was kept at 5 ℃ or lower, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 5.0 parts by mole of 4, 5-dichlorophthalonitrile was added. The mixture was stirred at 5 ℃ or below for 5 hours. To the mixture were added 2-cyanoacetamide (manufactured by Tokyo chemical industries, Ltd.) in an amount of 1.5 times the molar amount of 4, 5-dichlorophthalonitrile 5.0 parts and 6.1 parts of acetic acid while keeping the temperature at 5 ℃ or lower. The mixture was stirred at 65 ℃ for 3 days.
This mixture was mixed with 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol and 562 parts of water, and stirred at 65 ℃ for 9 days.
After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 3-8).
Figure BDA0003121580680004851
Identification of Compound represented by the formula (IZ3-8)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+392
Exact molecular weight (Exact masses): 391
Example 101Z3
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 3) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 3: 50 parts of the compound represented by the formula (IZ3-1) obtained in example 1Z3,
58 parts of a dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by the formula (IZ3-1) obtained in example 1Z3 was dispersed using a bead mill to obtain a colored composition. Next, the following were mixed to obtain colored curable composition 1Z3,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 3);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A colored curable composition 1Z3 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere 2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a photomask in which a line-and-space pattern of 100 μm was formed was used. The colored curable composition layer after exposure is mixed with a nonionic surfactant at 25 deg.CThe resultant was immersed in an aqueous solution containing 0.12% surfactant and 0.04% potassium hydroxide for 70 seconds to develop the resist, and then washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z3 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, thereby obtaining a colored coating film.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation). The phase difference value at an inclination angle of 45 ° of the colored coating film was measured using an ellipsometer (M-220 type spectroscopic ellipsometer; manufactured by japan spectro (ltd.)). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 7Z 3.
Example 102Z3
A colored curable composition 2Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with the compound represented by the formula (IZ3-19) obtained in example 2Z3, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 103Z3
A colored curable composition 3Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with the compound represented by the formula (IZ3-6) obtained in example 3Z3, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 104Z3
A colored curable composition 4Z3 was obtained and a colored pattern was obtained in the same manner as in example 101Z3, except that c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 105Z3
A colored curable composition 5Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ3-19) obtained in example 2Z3 was replaced with c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 106Z3
A colored curable composition 6Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ3-1) obtained in example 3Z3 was replaced with the compound represented by the formula (IZ3-6) obtained in example 3Z3, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 107Z3
A colored curable composition 7Z3 was obtained and a colored pattern was obtained in the same manner as in example 101Z3, except that c.i. pigment green 58 was replaced with c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 108Z3
A colored curable composition 8Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ3-19) obtained in example 2Z3 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 109Z3
A colored curable composition 9Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ3-1) obtained in example 3Z3 was replaced with the compound represented by the formula (IZ3-6) obtained in example 3Z 3826, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Comparative example 1Z3
A colored curable composition C1Z3 was obtained and a colored pattern was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Comparative example 2Z3
A colored curable composition C2Z3 was obtained in the same manner as in example 101Z3, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7, and the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C2Z3, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Comparative example 3Z3
A colored curable composition C3Z3 was obtained in the same manner as in example 101Z3, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59, and the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C3Z3, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
[ Table 7Z3]
TABLE 7Z3
Film thickness (mum) Phase difference value (nm)
Example 101Z3 2.3 4
Example 102Z3 2.3 3
Example 103Z3 2.3 3
Example 104Z3 2.3 4
Example 105Z3 2.3 3
Example 106Z3 2.3 3
Example 107Z3 2.3 4
Example 108Z3 2.3 3
Example 109Z3 2.3 3
Comparative example 1Z3 2.3 15
Comparative example 2Z3 2.3 15
Comparative example 3Z3 2.3 15
Example 110Z3
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
Resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 3) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 3: 50 parts of a compound represented by the formula (IZ3-1),
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by formula (IZ3-1) was dispersed using a bead mill to obtain a coloring composition. Next, the following were mixed to obtain a colored curable composition 10Z3,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 3);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z3 except that a colored curable composition 10Z3 was used instead of the colored curable composition 1Z 3. A colored coating film was obtained in the same manner as in example 101Z3 except that a colored curable composition 10Z3 was used in place of the colored curable composition 1Z3, and the film thickness and the retardation value were measured. The results are shown in Table 8Z 3.
Example 111Z3 to example 113Z3
A colored pattern was obtained in the same manner as in example 110Z3, except that the compound represented by the formula (IZ3-1) was replaced with the colorant shown in the column of "colorant" of table 8Z 3. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 3.
Example 114Z3 to example 117Z3
A colored pattern was obtained in the same manner as in example 110Z3, except that the compound represented by formula (IZ3-1) was replaced with the compound shown in the column of "colorant" in table 8Z3, and c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 3.
Example 118Z3 to example 121Z3
A colored pattern was obtained in the same manner as in example 110Z3, except that the compound represented by formula (IZ3-1) was replaced with the compound shown in the column of "colorant" in table 8Z3, and c.i. pigment green 58 was replaced with c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 3.
[ Table 8Z3]
TABLE 8Z3
Coloring agent Film thickness (mum) Phase difference value (nm)
Example 110Z3 A compound represented by the formula (IZ3-1) 2.3 4
Example 111Z3 A compound represented by the formula (IZ3-19) 2.3 3
Example 112Z3 A compound represented by the formula (IZ3-6) 2.3 3
Example 113Z3 A compound represented by the formula (IZ3-8) 2.3 3
Example 114Z3 A compound represented by the formula (IZ3-1) 2.3 4
Example 115Z3 A compound represented by the formula (IZ3-19) 2.3 3
Example 116Z3 A compound represented by the formula (IZ3-6) 2.3 3
Example 117Z3 A compound represented by the formula (IZ3-8) 2.3 3
Example 118Z3 A compound represented by the formula (IZ3-1) 2.3 4
Example 119Z3 A compound represented by the formula (IZ3-19) 2.3 3
Example 120Z3 A compound represented by the formula (IZ3-6) 2.3 3
Example 121Z3 A compound represented by the formula (IZ3-8) 2.3 3
In example Z3, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Example Z4
Example 1Z4
20.5 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 171 parts of methanol were mixed. While keeping the temperature at 5 ℃ for 1 hour and 20 minutes, a mixture of 23.9 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 215 parts of methanol was added dropwise to the obtained mixture.
The resulting mixture was stirred at 2-6 ℃ for 7 hours.
To the obtained mixture were added acetic acid (15.6 parts), 2-cyano-N, N-dimethylacetamide (17.9 parts, manufactured by Tokyo chemical industry Co., Ltd.) and methanol (118 parts), and the mixture was stirred at 40 ℃ for 15 hours and at 65 ℃ for 7 hours. To the obtained mixture were added 7.82 parts of acetic acid, 8.97 parts of 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo chemical industry Co., Ltd.) and 80 parts of methanol, and the mixture was stirred at 40 ℃ for 17 hours and at 65 ℃ for 4 hours. To the obtained mixture were added 12.6 parts of acetic acid, 14.3 parts of 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo chemical industry Co., Ltd.) and 104 parts of methanol, and the mixture was stirred at 40 ℃ for 16 hours and at 60 ℃ for 9 hours. To the obtained mixture were added acetic acid 6.32 parts, 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co., ltd.) 7.19 parts, and methanol 40 parts, and the mixture was stirred at 60 ℃ for 3 hours and at room temperature for 59 hours. To the obtained mixture were added acetic acid 15.7 parts, barbituric acid (manufactured by tokyo chemical industry corporation) 20.5 parts, methanol 16 parts, and water 744 parts, and the mixture was stirred at 60 ℃ for 24 hours. The resulting mixture was filtered, and the residue was washed with 50% aqueous methanol. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 43.1 parts of a compound represented by the formula (IZ 4-1).
Figure BDA0003121580680004921
Identification of Compound represented by the formula (IZ4-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+352
Exact molecular weight (Exact masses): 351
Example 2Z4
The procedure of example 1Z4 was repeated except for replacing 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.) with 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co.), to obtain a compound represented by the formula (IZ 4-2).
Figure BDA0003121580680004931
Identification of Compound represented by the formula (IZ4-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+380
Exact molecular weight (Exact masses): 379
Example 3Z4
The procedure of example 1Z4 was repeated except for replacing phthalonitrile (manufactured by tokyo chemical industry co.) with 4-nitrophthalonitrile (manufactured by tokyo chemical industry co.) to obtain compounds represented by the formula (IZ 4-79).
Figure BDA0003121580680004932
Identification of Compound represented by the formula (IZ4-79)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+397
Exact molecular weight (Exact masses): 396
Example 4Z4
A compound represented by formula (IZ4-80) was obtained in the same manner as in example 1Z4, except that phthalonitrile (manufactured by tokyo chemical industry co.) was replaced with 4-nitrophthalonitrile (manufactured by tokyo chemical industry co.) and 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.) was replaced with 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co.).
Figure BDA0003121580680004941
Identification of Compound represented by the formula (IZ4-80)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+425
Exact molecular weight (Exact masses): 424
Example 5Z4
A compound represented by the formula (IZ4-40) was obtained in the same manner as in example 1Z4, except that phthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.).
Figure BDA0003121580680004942
Identification of Compound represented by the formula (IZ4-40)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+408
Exact molecular weight (Exact masses): 407
Example 6Z4
The procedure of example 1Z4 was repeated except for replacing phthalonitrile (manufactured by tokyo chemical industry co.) with 4-tert-butylphthalonitrile (manufactured by tokyo chemical industry co.) and replacing 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.) with 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co.) to obtain a compound represented by formula (IZ 4-41).
Figure BDA0003121580680004951
Identification of Compound represented by the formula (IZ4-41)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+436
Exact molecular weight (Exact masses): 435
Example 7Z4XXX (651)
20.5 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 171 parts of methanol were mixed.
While maintaining the temperature at 2 to 5 ℃, a mixture of 23.9 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 215 parts of methanol was added dropwise to the obtained mixture over 1 hour and 20 minutes. The resulting mixture was stirred at 2-6 ℃ for 7 hours. To the obtained mixture were added acetic acid 15.6 parts, 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.) 17.9 parts, and methanol 46.9 parts. Further, up to this point in time, a total of 71 parts of methanol was added in addition to the above-mentioned methanol. The resulting mixture was stirred at 40 ℃ for 15 hours and at 65 ℃ for 7 hours. To the obtained mixture were added 7.82 parts of acetic acid, 8.97 parts of 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo chemical industry Co., Ltd.) and 80 parts of methanol, and the mixture was stirred at 40 ℃ for 17 hours and at 65 ℃ for 4 hours. To the obtained mixture were added 12.6 parts of acetic acid, 14.3 parts of 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo chemical industry Co., Ltd.) and 104 parts of methanol, and the mixture was stirred at 40 ℃ for 16 hours and at 60 ℃ for 9 hours. To the obtained mixture were added acetic acid 6.32 parts, 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co., ltd.) 7.19 parts, and methanol 40 parts, and the mixture was stirred at 60 ℃ for 3 hours and at room temperature for 59 hours. To the obtained mixture were added acetic acid 15.7 parts, barbituric acid (manufactured by tokyo chemical industry co., ltd.) 20.5 parts, methanol 16 parts, and water 744 parts, and the mixture was stirred at 60 ℃ for 9 days.
The resulting mixture was filtered, and the residue was washed with 50% aqueous methanol.
The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-1).
Figure BDA0003121580680004961
Identification of Compound represented by the formula (IZ4-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+352
Exact molecular weight (Exact masses): 351
Example 8Z4XXX
10.0 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 83 parts of methanol were mixed.
To the obtained mixture, a mixture of 11.7 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 105 parts of methanol was added dropwise over 1 hour and 30 minutes while maintaining the temperature at 2 to 5 ℃. The resulting mixture was stirred at 2-6 ℃ for 7 hours. To the obtained mixture were added 7.62 parts of acetic acid, 10.9 parts of 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co., ltd.) and 140 parts of methanol. In addition, up to this point, a total of 35 parts of methanol was added in addition to the above-mentioned methanol.
The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 3.82 parts of acetic acid and 5.48 parts of 2-cyano-N, N-diethylacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 7.65 parts of acetic acid, 10.0 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and the obtained residue was purified by column chromatography in the same manner as in example 1Z4 to obtain a compound represented by the formula (IZ 4-2).
Figure BDA0003121580680004971
Identification of Compound represented by the formula (IZ4-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+380
Exact molecular weight (Exact masses): 379
Example 9Z4XXX (529)
2.56 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 22 parts of methanol were mixed. To the obtained mixture was added 2.96 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) while keeping the temperature at 5 ℃ or lower. The resulting mixture was stirred for 3 hours while being kept at 5 ℃ or lower. While the resulting mixture was kept at 5 ℃ or lower, 1.84 parts of 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry) and 1.90 parts of acetic acid were added. The resulting mixture was stirred at 40 ℃ for 1 hour and at 65 ℃ for 1 hour. To the obtained mixture, 2.09 parts of barbituric acid (manufactured by tokyo chemical industry Co., Ltd.), 2.48 parts of acetic acid and 41 parts of water were added. In addition, a total of 24 parts of methanol was added up to this time point, in addition to the above-mentioned methanol. The resulting mixture was stirred at 65 ℃ for 15 hours. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-79).
Figure BDA0003121580680004972
Identification of Compound represented by the formula (IZ4-79)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+397
Exact molecular weight (Exact masses): 396
Example 10Z4XXX
10.0 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 149 parts of methanol were mixed. While keeping the temperature at 2 to 6 ℃, 5.86 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture over 20 minutes. The resulting mixture was stirred for 5 hours while being kept at 5 ℃ or lower. While the resulting mixture was kept at 5 ℃ or lower, 5.79 parts of acetic acid, 8.10 parts of 2-cyano-N, N-diethylacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 2.88 parts of acetic acid and 4.05 parts of 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co.). The resulting mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 140 parts of methanol was added in addition to the above-mentioned methanol. To the obtained mixture were added 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-80).
Figure BDA0003121580680004981
Identification of Compound represented by the formula (IZ4-80)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+425
Exact molecular weight (Exact masses): 424
Example 11Z4XXX
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days. To the obtained mixture, 5.42 parts of acetic acid and 6.09 parts of 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 2.69 parts of acetic acid and 3.04 parts of 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co., ltd.) and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-40).
Figure BDA0003121580680004991
Identification of Compound represented by the formula (IZ4-40)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+408
Exact molecular weight (Exact masses): 407
Example 12Z4XXX
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days. To the obtained mixture, 5.42 parts of acetic acid and 7.61 parts of 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industries, ltd.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 2.69 parts of acetic acid and 3.80 parts of 2-cyano-N, N-diethylacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-41).
Figure BDA0003121580680005001
Identification of Compound represented by the formula (IZ4-41)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+436
Exact molecular weight (Exact masses): 435
Example 13Z4
5.0 parts of 4, 5-dichlorophthalonitrile and 62 parts of methanol were mixed. While the mixture was kept at 5 ℃ or lower, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 5.0 parts by mole of 4, 5-dichlorophthalonitrile was added.
The mixture was stirred at 5 ℃ or below for 5 hours. To the mixture, while keeping the temperature at 5 ℃ or lower, 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo chemical industry Co., Ltd.) having a molar amount 1.5 times that of 5.0 parts of 4, 5-dichlorophthalonitrile and 6.1 parts of acetic acid were added. The mixture was stirred at 65 ℃ for 3 days. This mixture was mixed with 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol and 562 parts of water, and stirred at 65 ℃ for 9 days. The solvent was distilled off from the mixture by a rotary evaporator, and the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-321).
Figure BDA0003121580680005002
Identification of Compound represented by the formula (IZ4-321)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H ]+420
Exact molecular weight (Exact masses): 419
Example 101Z4
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 4) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 4: 50 parts of the compound represented by the formula (IZ4-1) obtained in example 1Z4,
58 parts of a dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by the formula (IZ4-1) obtained in example 1Z4 was dispersed using a bead mill to obtain a colored composition. Next, the following were mixed to obtain colored curable composition 1Z4,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 4);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
Polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A colored curable composition 1Z4 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a photomask in which a line-and-space pattern of 100 μm was formed was used. The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z4 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, thereby obtaining a coloringAnd (6) coating.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation).
The phase difference value at an inclination angle of 45 ° of the colored coating film was measured using an ellipsometer (M-220 type spectroscopic ellipsometer; manufactured by japan spectro (ltd.)). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 9Z 4.
Example 102Z4
A colored curable composition 2Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-2) obtained in example 2Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 103Z4
A colored curable composition 3Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-79) obtained in example 3Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 104Z4
A colored curable composition 4Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-80) obtained in example 4Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 105Z4
A colored curable composition 5Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-40) obtained in example 5Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 106Z4
A colored curable composition 6Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-41) obtained in example 6Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 107Z4
A colored curable composition 7Z4 was obtained and a colored pattern was obtained in the same manner as in example 101Z4, except that c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 108Z4
A colored curable composition 8Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-1) obtained in example 2Z4 was replaced with the compound represented by the formula (IZ4-2) obtained in example 2Z4, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 109Z4
A colored curable composition 9Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-79) obtained in example 3Z4 was replaced with c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 110Z4
A colored curable composition 10Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-1) obtained in example 4Z4 was replaced with the compound represented by the formula (IZ4-80) obtained in example 4Z4, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 111Z4
A colored curable composition 11Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-40) obtained in example 5Z4 was replaced with c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 112Z4
A colored curable composition 12Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-41) obtained in example 6Z4 was replaced with c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 113Z4
A colored curable composition 13Z4 was obtained in the same manner as in example 101Z4 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 114Z4
A colored curable composition 14Z4 was obtained in the same manner as in example 101Z4 except that c.i. pigment green 58 was replaced with c.i. pigment green 59 and the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-2) obtained in example 2Z4, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 115Z4
A colored curable composition 15Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-79) obtained in example 3Z4 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 116Z4
A colored curable composition 16Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-80) obtained in example 4Z4 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 117Z4
A colored curable composition 17Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-40) obtained in example 5Z4 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 118Z4
A colored curable composition 18Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-41) obtained in example 6Z4 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Comparative example 1Z4
A colored curable composition C1Z4 was obtained and a colored pattern was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Comparative example 2Z4
A colored curable composition C2Z4 was obtained in the same manner as in example 101Z4, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7, and the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C2Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Comparative example 3Z4
A colored curable composition C3Z4 was obtained in the same manner as in example 101Z4, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59, and the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C3Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
[ Table 9Z4]
TABLE 9Z4
Film thickness (mum) Phase difference value (nm)
Example 101Z4 2.3 4
Example 102Z4 2.3 4
Example 103Z4 2.3 3
Example 104Z4 2.3 3
Example 105Z4 2.3 3
Example 106Z4 2.3 3
Example 107Z4 2.3 4
Example 108Z4 2.3 4
Example 109Z4 2.3 3
Example 110Z4 2.3 3
Example 111Z4 2.3 3
Example 112Z4 2.3 3
Example 113Z4 2.3 4
Example 114Z4 2.3 4
Example 115Z4 2.3 3
Example 116Z4 2.3 3
Example 117Z4 2.3 3
Example 118Z4 2.3 3
Comparative example 1Z4 2.3 15
Comparative example 2Z4 2.3 15
Comparative example 3Z4 2.3 15
Example 119Z4
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 4) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 4: 50 parts of a compound represented by the formula (IZ4-1),
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by formula (IZ4-1) was dispersed using a bead mill to obtain a coloring composition. Next, the following were mixed to obtain a colored curable composition 19Z4,
The total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 4);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z4 except that a colored curable composition 19Z4 was used instead of the colored curable composition 1Z 4. A colored coating film was obtained in the same manner as in example 101Z4 except that a colored curable composition 19Z4 was used in place of the colored curable composition 1Z4, and the film thickness and the retardation value were measured. The results are shown in Table 10Z 4.
Example 120Z4 to example 125Z4
A colored pattern was obtained in the same manner as in example 119Z4 except that the compound represented by the formula (IZ4-1) was replaced with the colorant shown in the column of "colorant" in table 10Z 4. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 10Z 4.
Example 126Z4 to example 132Z4
A colored pattern was obtained in the same manner as in example 119Z4 except that the compound represented by the formula (IZ4-1) was replaced with the compound shown in the column of "colorant" in table 10Z4 and the c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 10Z 4.
Example 133Z4 to example 139Z4
A colored pattern was obtained in the same manner as in example 119Z4 except that the compound represented by the formula (IZ4-1) was replaced with the compound shown in the column of "colorant" in table 10Z4 and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 10Z 4.
[ Table 10Z4]
TABLE 10Z4
Coloring agent Film thickness (mum) Phase difference value (nm)
Example 119Z4 A compound represented by the formula (IZ4-1) 2.3 4
Example 120Z4 A compound represented by the formula (IZ4-2) 2.3 4
Example 121Z4 A compound represented by the formula (IZ4-79) 2.3 3
Example 122Z4 A compound represented by the formula (IZ4-80) 2.3 3
Example 123Z4 A compound represented by the formula (IZ4-40) 2.3 3
Example 124Z4 A compound represented by the formula (IZ4-41) 2.3 3
Example 125Z4 A compound represented by the formula (IZ4-321) 2.3 3
Example 126Z4 A compound represented by the formula (IZ4-1) 2.3 4
Example 127Z4 A compound represented by the formula (IZ4-2) 2.3 4
Example 128Z4 A compound represented by the formula (IZ4-79) 2.3 3
Example 129Z4 A compound represented by the formula (IZ4-80) 2.3 3
Example 130Z4 A compound represented by the formula (IZ4-40) 2.3 3
Example 131Z4 A compound represented by the formula (IZ4-41) 2.3 3
Example 132Z4 A compound represented by the formula (IZ4-321) 2.3 3
Example 133Z4 A compound represented by the formula (IZ4-1) 2.3 4
Example 134Z4 A compound represented by the formula (IZ4-2) 2.3 4
Example 135Z4 A compound represented by the formula (IZ4-79) 2.3 3
Example 136Z4 A compound represented by the formula (IZ4-80) 2.3 3
Example 137Z4 A compound represented by the formula (IZ4-40) 2.3 3
Example 138Z4 A compound represented by the formula (IZ4-41) 2.3 3
Example 139Z4 A compound represented by the formula (IZ4-321) 2.3 3
In example Z4, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Example Z5
Example 1Z5
25.2 parts of 4-tert-butylphthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 212 parts of methanol were mixed. While keeping the temperature at 5 ℃, a mixture of 20.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 184 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the resulting mixture, 13.7 parts of acetic acid and 13.5 parts of 2-cyano-N-methylacetamide were added at 10 to 20 ℃. The obtained mixture was stirred at 10 to 20 ℃ for 5 hours and then at 40 ℃ for 16 hours. To the resulting mixture, 6.79 parts of acetic acid, 6.75 parts of 2-cyano-N-methylacetamide and 201 parts of methanol were added, and the mixture was stirred at 40 ℃ for 6 hours and at 50 ℃ for 65 hours. To the obtained mixture were added 13.5 parts of acetic acid, 18.3 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 604 parts of water, and the mixture was stirred at 40 ℃ for 52 hours. The resulting mixture was filtered, and the residue was washed with 50% aqueous methanol. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 49.9 parts of a compound represented by the formula (IZ 5-1).
Figure BDA0003121580680005111
Identification of Compound represented by the formula (IZ5-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+394
Exact molecular weight (Exact masses): 393
Example 2Z5
The procedure of example 1Z5 was repeated except for replacing 2-cyano-N-methylacetamide with 2-cyanoacetanilide (manufactured by tokyo chemical industry co., ltd.) to obtain a compound represented by the formula (IZ 5-3).
Figure BDA0003121580680005112
Identification of Compound represented by the formula (IZ5-3)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+456
Exact molecular weight (Exact masses): 455
Example 3Z5
A compound represented by the formula (IZ5-23) was obtained in the same manner as in example 1Z5, except that 4-t-butylphthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.) was replaced with 4-nitrophthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.).
Figure BDA0003121580680005121
Identification of Compound represented by the formula (IZ5-23)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+383
Exact molecular weight (Exact masses): 382
Example 4Z5
The procedure of example 1Z5 was repeated except for replacing 4-tert-butylphthalonitrile (manufactured by tokyo chemical industry co.) with 4-nitrophthalonitrile (manufactured by tokyo chemical industry co.) and replacing 2-cyano-N-methylacetamide with 2-cyanoacetanilide (manufactured by tokyo chemical industry co.) to obtain a compound represented by formula (IZ 5-25).
Figure BDA0003121580680005122
Identification of Compound represented by the formula (IZ5-25)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+445
Exact molecular weight (Exact masses): 444
Example 5Z5XXX (653)
25.2 parts of 4-tert-butylphthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 212 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 20.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 184 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days. To the resulting mixture, 13.7 parts of acetic acid and 13.5 parts of 2-cyano-N-methylacetamide were added at 10 to 20 ℃. The obtained mixture was stirred at 10 to 20 ℃ for 5 hours and then at 40 ℃ for 16 hours. To the resulting mixture, 6.79 parts of acetic acid and 6.75 parts of 2-cyano-N-methylacetamide were added, and stirring was performed at 40 ℃ for 6 hours and at 50 ℃ for 65 hours. In addition, a total of 201 parts of methanol was added up to this time point, in addition to the above-mentioned methanol.
To the resulting mixture were added 13.5 parts of acetic acid, 18.3 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 604 parts of water, and the mixture was stirred at 40 ℃ for 53 hours. The resulting mixture was filtered, and the residue was washed with 50% aqueous methanol. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 5-1).
Figure BDA0003121580680005131
Identification of Compound represented by the formula (IZ5-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+394
Exact molecular weight (Exact masses): 393
Example 6Z5XXX
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the obtained mixture, 5.42 parts of acetic acid and 8.69 parts of 2-cyanoacetanilide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days.
To the resulting mixture were added 2.69 parts of acetic acid and 4.35 parts of 2-cyanoacetanilide (manufactured by Tokyo chemical industry Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days.
The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a compound represented by the formula (IZ 5-3).
Figure BDA0003121580680005141
Identification of Compound represented by the formula (IZ5-3)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+456
Exact molecular weight (Exact masses): 455
Example 7Z5XXX (654)
25.2 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 376 parts of methanol were mixed together. 14.8 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture over 20 minutes while keeping the temperature at 2 to 6 ℃. The resulting mixture was stirred for 5 hours while being kept at 5 ℃ or lower.
While the resulting mixture was kept at 5 ℃ or lower, 9.31 parts of acetic acid and 14.4 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at room temperature for 14 hours and at 40 ℃ for 29 hours.
To the resulting mixture, 1.50 parts of acetic acid and 2.24 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at 40 ℃ for 19 hours.
To the resulting mixture, 4.83 parts of acetic acid and 7.36 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at 40 ℃ for 79 hours.
To the resulting mixture, 4.60 parts of acetic acid and 7.30 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at 40 ℃ for 24 hours. In addition, a total of 259 parts of methanol were added to the reaction mixture up to this point in time, in addition to the above-mentioned methanol. To the resulting mixture were added 12.1 parts of acetic acid, 19.1 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.), 635 parts of water, 14.2 parts of methanol and 20 parts of 50% methanol aqueous solution, followed by stirring at 40 ℃ for 21 hours and at 63 ℃ for 5 hours.
To the resulting mixture was added 23.4 parts of acetic acid, and the mixture was stirred at 63 ℃ for 18 hours. To the resulting mixture were added 24.9 parts of acetic acid, 19.4 parts of barbituric acid and 32.8 parts of methanol, and the mixture was stirred at 63 ℃ for 7 hours. To the resulting mixture was added 259 parts of a 50% methanol aqueous solution, and the mixture was stirred at 63 ℃ for 7 days. The resulting mixture was filtered. To the resulting residue, 902 parts of tetrahydrofuran was added, and the mixture was stirred at room temperature. The mixture was filtered, and the resulting residue was purified by column chromatography to give a compound represented by the formula (IZ 5-23).
Figure BDA0003121580680005151
Identification of Compound represented by the formula (IZ5-23)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+383
Exact molecular weight (Exact masses): 382
Example 8Z5XXX
10.0 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 149 parts of methanol were mixed. While keeping the temperature at 2 to 6 ℃, 5.86 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture over 20 minutes. The resulting mixture was stirred for 5 hours while being kept at 5 ℃ or lower.
While the resulting mixture was kept at 5 ℃ or lower, 5.79 parts of acetic acid, 9.25 parts of 2-cyanoacetanilide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 2.88 parts of acetic acid and 4.63 parts of 2-cyanoacetanilide (manufactured by Tokyo Kasei Kogyo Co., Ltd.). The resulting mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 140 parts of methanol was added in addition to the above-mentioned methanol.
To the obtained mixture were added 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a compound represented by the formula (IZ 5-25).
Figure BDA0003121580680005161
Identification of Compound represented by the formula (IZ5-25)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+445
Exact molecular weight (Exact masses): 444
Example 9Z5
5.0 parts of 4, 5-dichlorophthalonitrile and 62 parts of methanol were mixed.
While the mixture was kept at 5 ℃ or lower, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 5.0 parts by mole of 4, 5-dichlorophthalonitrile was added. The mixture was stirred at 5 ℃ or below for 5 hours. To the mixture were added 2-cyano-N-methylacetamide and 6.1 parts of acetic acid in an amount of 1.5 times the molar amount of 5.0 parts of 4, 5-dichlorophthalonitrile, while keeping the mixture at 5 ℃ or lower. The mixture was stirred at 65 ℃ for 3 days.
This mixture was mixed with 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol and 562 parts of water, and stirred at 65 ℃ for 9 days. After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 5-247).
Figure BDA0003121580680005171
Identification of Compound represented by the formula (IZ5-247)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+406
Exact molecular weight (Exact masses): 405
Example 101Z5
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 5) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 5: the compound represented by the formula (IZ5-1) obtained in example 1Z5
50 parts of (a) a mixture of (b),
dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.)
58 parts of (a) to (b),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by the formula (IZ5-1) obtained in example 1Z5 was dispersed using a bead mill to obtain a colored composition.
Next, the following were mixed to obtain colored curable composition 1Z5,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 5);
400 parts of the obtained coloring composition;
Resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): n-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01, manufactured by BASF corporation)
15 parts of (1);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A colored curable composition 1Z5 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a photomask in which a line-and-space pattern of 100 μm was formed was used. Exposing the colored curable composition layer to a solution containing a nonionic surfactant 0.12 at 25 deg.C % and 0.04% potassium hydroxide aqueous solution for 70 seconds, followed by development and water washing. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z5 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, thereby obtaining a colored coating film.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation).
The phase difference value at an inclination angle of 45 ° of the colored coating film was measured using an ellipsometer (M-220 type spectroscopic ellipsometer; manufactured by japan spectro (ltd.)). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 8Z 5.
Example 102Z5
A colored curable composition 2Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with the compound represented by the formula (IZ5-3) obtained in example 2Z5, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 103Z5
A colored curable composition 3Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with the compound represented by the formula (IZ5-23) obtained in example 3Z5, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 104Z5
A colored curable composition 4Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with the compound represented by the formula (IZ5-25) obtained in example 4Z5, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 105Z5
A colored curable composition 5Z5 was obtained in the same manner as in example 101Z5 except that c.i. pigment green 58 was replaced with c.i. pigment green 7, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 106Z5
A colored curable composition 6Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-1) obtained in example 2Z5 was replaced with the compound represented by the formula (IZ5-3) obtained in example 2Z5, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 107Z5
A colored curable composition 7Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-1) obtained in example 3Z5 was replaced with the compound represented by the formula (IZ5-23) obtained in example 3Z5, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 108Z5
A colored curable composition 8Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-25) obtained in example 4Z5 was replaced with c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 109Z5
A colored curable composition 9Z5 was obtained in the same manner as in example 101Z5 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 110Z5
A colored curable composition 10Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-1) obtained in example 2Z5 was replaced with the compound represented by the formula (IZ5-3) obtained in example 2Z5, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 111Z5
A colored curable composition 11Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-1) obtained in example 3Z5 was replaced with the compound represented by the formula (IZ5-23) obtained in example 3Z5, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 112Z5
A colored curable composition 12Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-25) obtained in example 4Z5 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Comparative example 1Z5
A colored curable composition C1Z5 was obtained and a colored pattern was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Comparative example 2Z5
A colored curable composition C2Z5 was obtained in the same manner as in example 101Z5, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7, and the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C2Z5, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Comparative example 3Z5
A colored curable composition C3Z5 was obtained in the same manner as in example 101Z5, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59, and the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C3Z5, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
[ Table 8Z5]
TABLE 8Z5
Film thickness (mum) Phase difference value (nm)
Example 101Z5 2.3 3
Example 102Z5 2.3 3
Example 103Z5 2.3 3
Example 104Z5 2.3 3
Example 105Z5 2.3 3
Example 106Z5 2.3 3
Example 107Z5 2.3 3
Example 108Z5 2.3 3
Example 109Z5 2.3 3
Example 110Z5 2.3 3
Example 111Z5 2.3 3
Example 112Z5 2.3 3
Comparative example 1Z5 2.3 15
Comparative example 2Z5 2.3 15
Comparative example 3Z5 2.3 15
Example 113Z5
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 5) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 5: 50 parts of a compound represented by the formula (IZ5-1),
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by formula (IZ5-1) was dispersed using a bead mill to obtain a coloring composition.
Next, the following were mixed to obtain a colored curable composition 13Z5,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 5);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z5 except that a colored curable composition 13Z5 was used instead of the colored curable composition 1Z 5. A colored coating film was obtained in the same manner as in example 101Z5 except that a colored curable composition 13Z5 was used in place of the colored curable composition 1Z5, and the film thickness and the retardation value were measured. The results are shown in Table 9Z 5.
Example 114Z5 to example 117Z5
A colored pattern was obtained in the same manner as in example 113Z5, except that the compound represented by the formula (IZ5-1) was replaced with the colorant shown in the column of "colorant" in table 9Z 5. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 5.
Example 118Z5 to example 122Z5
A colored pattern was obtained in the same manner as in example 113Z5 except that the compound represented by the formula (IZ5-1) was replaced with the compound shown in the column of "colorant" in table 9Z5 and the c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 5.
Example 123Z5 to example 127Z5
A colored pattern was obtained in the same manner as in example 113Z5 except that the compound represented by the formula (IZ5-1) was replaced with the compound shown in the column of "colorant" in table 9Z5 and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 5.
[ Table 9Z5]
TABLE 9Z5
Coloring agent Film thickness (mum) Phase difference value (nm)
Example 113Z5 A compound represented by the formula (IZ5-1) 2.3 3
Example 114Z5 A compound represented by the formula (IZ5-3) 2.3 3
Example 115Z5 A compound represented by the formula (IZ5-23) 2.3 3
Example 116Z5 A compound represented by the formula (IZ5-25) 2.3 3
Example 117Z5 A compound represented by the formula (IZ5-247) 2.3 3
Example 118Z5 A compound represented by the formula (IZ5-1) 2.3 3
Example 119Z5 A compound represented by the formula (IZ5-3) 2.3 3
Example 120Z5 A compound represented by the formula (IZ5-23) 2.3 3
Example 121Z5 A compound represented by the formula (IZ5-25) 2.3 3
Example 122Z5 A compound represented by the formula (IZ5-247) 2.3 3
Example 123Z5 A compound represented by the formula (IZ5-1) 2.3 3
Example 124Z5 A compound represented by the formula (IZ5-3) 2.3 3
Example 125Z5 A compound represented by the formula (IZ5-23) 2.3 3
Example 126Z5 A compound represented by the formula (IZ5-25) 2.3 3
Example 127Z5 A compound represented by the formula (IZ5-247) 2.3 3
In example Z5, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Example Z6
Example 1Z6
7.02 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 61.6 parts of methanol were mixed. While the temperature of the obtained mixture was kept at 2 ℃, a mixture of 8.20 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 74.6 parts of methanol was added dropwise over 1 hour and 30 minutes. The resulting mixture was stirred at 2 ℃ for 6 hours and 15 minutes. While the temperature of the obtained mixture was kept at 4 ℃ or lower, 10.7 parts of acetic acid was added. To the resulting mixture, 17.6 parts of benzoylacetonitrile (benzophenonitrile) (manufactured by tokyo chemical industry Co., Ltd.) was added, and the mixture was stirred at room temperature for 44 hours. The resulting mixture was filtered, and the residue was washed with 800 parts of methanol. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 18.0 parts of a compound represented by the formula (IFFZ 6-1).
Figure BDA0003121580680005251
Identification of Compound represented by the formula (IFFZ6-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+402
Exact molecular weight (Exact masses): 401
While 7.6 parts of fuming sulfuric acid (25%) at 3 ℃ (manufactured by Wako pure chemical industries, Ltd.) was stirred, 0.513 part of the compound represented by the formula (IFFZ6-1) obtained in example 2Z6 was added. To the resulting mixture was added 3.8 parts of fuming sulfuric acid (25%) (manufactured by Wako pure chemical industries, Ltd.). The resulting mixture was stirred and heated to 15 ℃ over 3 hours and 30 minutes. 139 parts of ice water and 38.2 parts of sodium chloride were added to the obtained mixture. The resulting mixture was filtered, and the resulting residue was washed with 64 parts of a 21.5% aqueous sodium chloride solution. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 1.02 parts of a compound represented by the formula (IFFZ 6-2).
Figure BDA0003121580680005252
Identification of Compound represented by the formula (IFFZ6-2)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-560
Exact molecular weight (Exact masses): 561
5.11 parts of a compound represented by the formula (IFFZ6-2) and 511 parts of water were mixed at room temperature. To the obtained mixture, a mixture of 6.72 parts of barium chloride dihydrate (manufactured by Wako pure chemical industries, Ltd.) and 60 parts of water was added. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 2.98 parts of a compound represented by the formula (IFZ 6-4).
Figure BDA0003121580680005261
Identification of Compound represented by the formula (IFZ6-4)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Ba++H]-560
Exact molecular weight (Exact masses): 697
Example 2Z6
10.0 parts of a compound represented by the formula (IFFZ6-2) and 1000 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 87.0 parts of a 10% aqueous solution of barium chloride dihydrate. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 9.43 parts of a compound represented by the formula (IFZ 6-4).
Figure BDA0003121580680005262
Identification of Compound represented by the formula (IFZ6-4)
(Mass Spectrometry) ionization modeThe formula is ESI-: m/z ═ M-Ba + H]-560
Exact molecular weight (Exact masses): 697
Example 3Z6
5.02 parts of a compound represented by the formula (IFFZ6-2) and 500 parts of a 50% aqueous methanol solution were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 95.0 parts of a 10% strontium chloride hexahydrate aqueous solution. The resulting mixture was filtered, and the resulting residue was washed with 50% aqueous methanol. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 4.00 parts of a compound represented by the formula (IFZ 6-3).
Figure BDA0003121580680005271
Identification of Compound represented by the formula (IFZ6-3)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Sr + H]-560
Exact molecular weight (Exact masses): 647
Example 4Z6
0.501 part of a compound represented by the formula (IFFZ6-2) and 50.0 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 12.6 parts of a 10% aqueous calcium chloride solution. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 0.024 part of a compound represented by the formula (IFZ 6-2).
Figure BDA0003121580680005272
Identification of Compound represented by the formula (IFZ6-2)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Ca + H]-560
Exact molecular weight (Exact masses): 599
Example 5Z6
0.500 parts of a compound represented by the formula (IFFZ6-2) and 50.0 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 3.52 parts of a 10% aqueous solution of manganese chloride tetrahydrate. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 0.015 part of a compound represented by the formula (IFZ 6-10).
Figure BDA0003121580680005281
Identification of Compound represented by the formula (IFZ6-10)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Mn + H]-560
Exact molecular weight (Exact masses): 614
Example 6Z6
A compound represented by the formula (IFZ6-6) was obtained in the same manner as in example 2Z6, except that barium chloride dihydrate was replaced with zinc nitrate hexahydrate.
Figure BDA0003121580680005282
Identification of Compound represented by the formula (IFZ6-6)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Zn + H]-560
Exact molecular weight (Exact masses): 623
Example 7Z6
5.00 parts of a compound represented by the formula (IFFZ6-2) and 500 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 23.7 parts of a 10% aqueous aluminum chloride solution. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 0.474 parts of a compound represented by the formula (IFZ 6-11).
Figure BDA0003121580680005291
Identification of Compound represented by the formula (IFZ6-11)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ [ (M-2Al)/3+ H]-560
Exact molecular weight (Exact masses): 1731
Example 8Z6
5.01 parts of a compound represented by the formula (IFFZ6-2) and 500 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 36.0 parts of a 10% aqueous solution of ferric nitrate nonahydrate. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 3.80 parts of a compound represented by the formula (IFZ 6-12).
Figure BDA0003121580680005292
Identification of Compound represented by the formula (IFZ6-12)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ [ (M-2Fe)/3+ H]-560
Exact molecular weight (Exact masses): 1789
Example 9Z6
0.498 part of the compound represented by the formula (IFFZ6-2) and 49.9 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 4.45 parts of a 10% aqueous copper sulfate pentahydrate solution. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 0.018 parts of a compound represented by the formula (IFZ 6-31).
Figure BDA0003121580680005301
Identification of Compound represented by the formula (IFZ6-31)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Cu + H]-560
Exact molecular weight (Exact masses): 622
Example 10Z6
The procedure was carried out in the same manner as in example 1Z6 except that benzoylacetonitrile was replaced with 4-cyanoacetylbenzoic acid to give a compound represented by the formula (IFFZ6-1), thereby giving a compound represented by the formula (IJZ 6-1).
Figure BDA0003121580680005302
Identification of Compound represented by the formula (IJJZ6-1)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-488
Exact molecular weight (Exact masses): 489
16.3 parts of a compound represented by the formula (IJZ 6-1) and 1630 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the resulting homogeneous solution, 163 parts of a 10% barium chloride dihydrate aqueous solution was added. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 7.49 parts of a compound represented by the formula (IJZ 6-4).
Figure BDA0003121580680005311
Identification of Compound represented by the formula (IJZ6-4)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Ba + H]-488
Exact molecular weight (Exact masses): 625
Example 11Z6
A compound represented by the formula (IJZ6-3) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with strontium chloride hexahydrate.
Figure BDA0003121580680005312
Identification of Compound represented by the formula (IJZ6-3)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Sr + H]-488
Exact molecular weight (Exact masses): 575
Example 12Z6
A compound represented by the formula (IJZ6-2) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with calcium chloride.
Figure BDA0003121580680005321
Identification of Compound represented by the formula (IJZ6-2)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Ca + H ]-488
Exact molecular weight (Exact masses): 527
Example 13Z6
A compound represented by the formula (IJZ6-10) was obtained by the same operation as in example 10Z6, except that barium chloride dihydrate was replaced with manganese chloride tetrahydrate.
Figure BDA0003121580680005322
Identification of Compound represented by the formula (IJZ6-10)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Mn + H]-488
Exact molecular weight (Exact masses): 542
Example 14Z6
A compound represented by the formula (IJZ6-31) was obtained by the same operation as in example 10Z6, except that barium chloride dihydrate was replaced with copper sulfate pentahydrate.
Figure BDA0003121580680005323
Identification of Compound represented by the formula (IJZ6-31)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Cu + H]-488
Exact molecular weight (Exact masses): 550
Example 15Z6
A compound represented by the formula (IJZ6-6) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with zinc nitrate hexahydrate.
Figure BDA0003121580680005331
Identification of Compound represented by the formula (IJZ6-6)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Zn + H]-488
Exact molecular weight (Exact masses): 551
Example 16Z6
A compound represented by the formula (IJZ6-11) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with aluminum chloride.
Figure BDA0003121580680005332
Identification of Compound represented by the formula (IJZ6-11)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ [ (M-2Al)/3+ H]-488
Exact molecular weight (Exact masses): 1515
Example 17Z6
A compound represented by the formula (IJZ6-12) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with iron nitrate nonahydrate.
Figure BDA0003121580680005341
Identification of Compound represented by the formula (IJZ6-12)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ [ (M-2Fe)/3+ H]-488
Exact molecular weight (Exact masses): 1573
Example 18Z6
A compound represented by the formula (IJZ6-1) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with magnesium chloride.
Figure BDA0003121580680005342
Identification of Compound represented by the formula (IJZ6-1)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Mg + H]-488
Exact molecular weight (Exact masses): 511
Example 19Z6
5.00 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 44 parts of methanol were mixed. To the obtained mixture, a mixture of 5.84 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 54 parts of methanol was added dropwise over 1 hour and 30 minutes while keeping the temperature at 5 ℃ or lower. The resulting mixture was stirred at 5 ℃ or lower for 12 hours. To the resulting mixture, 11.5 parts of acetic acid, 24.5 parts of 4-cyanoacetylbenzoic acid and 712 parts of methanol were added while keeping the temperature at 5 ℃ or lower. The resulting mixture was stirred at room temperature for 4 hours and then at 40 ℃ for 96 hours. The solvent was distilled off from the obtained mixture by a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.471 part of a compound represented by the formula (IJJZ 6-1).
Figure BDA0003121580680005351
Identification of Compound represented by the formula (IJJZ6-1)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-488
Exact molecular weight (Exact masses): 489
Example 101Z6
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 6) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 6: 50 parts of a compound represented by the formula (IFZ6-4),
58 parts of a dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by formula (IFZ6-4) was dispersed using a bead mill, to thereby obtain a coloring composition. Next, the following were mixed to obtain colored curable composition 1Z6,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 6);
400 parts of the obtained coloring composition;
Resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A colored curable composition 1Z6 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a photomask in which a line-and-space pattern of 100 μm was formed was used. The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z6 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, washed with water, and dried. Subjecting the dried colored curable composition layer to 3 at 230 ℃And baked after 0 minute, thereby obtaining a colored coating film.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation).
The phase difference value at an inclination angle of 45 ° of the colored coating film was measured using an ellipsometer (M-220 type spectroscopic ellipsometer; manufactured by japan spectro (ltd.)). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 5Z 6.
Example 102Z6
A colored curable composition 2Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-2). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 103Z6
A colored curable composition 3Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-3). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 104Z6
A colored curable composition 4Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-6). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 105Z6
A colored curable composition 5Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-10). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 106Z6
A colored curable composition 6Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-11). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 107Z6
A colored curable composition 7Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-12). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 108Z6
A colored curable composition 8Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-31). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 109Z6
A colored curable composition 9Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-1). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 110Z6
A colored curable composition 10Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-2). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 111Z6
A colored curable composition 11Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-3). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 112Z6
A colored curable composition 12Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-4). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 113Z6
A colored curable composition 13Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-6). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 114Z6
A colored curable composition 14Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-10). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 115Z6
A colored curable composition 15Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-11). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 116Z6
A colored curable composition 16Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-12). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 117Z6
A colored curable composition 17Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-31). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 118Z6
A colored curable composition 18Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-2) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 119Z6
A colored curable composition 19Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-3) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 120Z6
A colored curable composition 20Z6 was obtained in the same manner as in example 101Z6, except that c.i. pigment green 58 was replaced with c.i. pigment green 7, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 121Z6
A colored curable composition 21Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-6) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 122Z6
A colored curable composition 22Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-10) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 123Z6
A colored curable composition 23Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-11) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 124Z6
A colored curable composition 24Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-12) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 125Z6
A colored curable composition 25Z6 was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-31) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 126Z6
A colored curable composition 26Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-1) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 127Z6
A colored curable composition 27Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-2) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 128Z6
A colored curable composition 28Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-3) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 129Z6
A colored curable composition 29Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-4) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 130Z6
A colored curable composition 30Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-6) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 131Z6
A colored curable composition 31Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-10) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 132Z6
A colored curable composition 32Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-11) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 133Z6
A colored curable composition 33Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-12) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 134Z6
A colored curable composition 34Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-31) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 135Z6
A colored curable composition 35Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-2) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 136Z6
A colored curable composition 36Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-3) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 137Z6
A colored curable composition 37Z6 was obtained in the same manner as in example 101Z6 except that the c.i. pigment green 58 was replaced with c.i. pigment green 59, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 138Z6
A colored curable composition 38Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-6) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 139Z6
A colored curable composition 39Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-10) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 140Z6
A colored curable composition 40Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-11), and the c.i. pigment green 58 was replaced with the c.i. pigment green 59, to obtain a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 141Z6
A colored curable composition 41Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-12) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 142Z6
A colored curable composition 42Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-31) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 143Z6
A colored curable composition 43Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-1) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 144Z6
A colored curable composition 44Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-2) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 145Z6
A colored curable composition 45Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-3) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 146Z6
A colored curable composition 46Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-4), and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 147Z6
A colored curable composition 47Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-6) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 148Z6
A colored curable composition 48Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-10) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 149Z6
A colored curable composition 49Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-11), and the c.i. pigment green 58 was replaced with the c.i. pigment green 59, to obtain a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 150Z6
A colored curable composition 50Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-12), and the c.i. pigment green 58 was replaced with the c.i. pigment green 59, to obtain a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 151Z6
A colored curable composition 51Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-31) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Comparative example 1Z6
A colored curable composition C1Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 6.
Comparative example 2Z6
A colored curable composition C2Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the compound represented by formula (IFZ6-4) was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 6.
Comparative example 3Z6
A colored curable composition C3Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and the compound represented by formula (IFZ6-4) was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 6.
[ Table 5Z6]
TABLE 5Z6
Film thickness (mum) Phase difference value (nm)
Example 101Z6 2.3 2
Example 102Z6 2.3 3
Example 103Z6 2.3 2
Example 104Z6 2.3 3
Example 105Z6 2.3 2
Example 106Z6 2.3 2
Example 107Z6 2.3 3
Example 108Z6 2.3 3
Example 109Z6 2.3 2
Example 110Z6 2.3 2
Example 111Z6 2.3 2
Example 112Z6 2.3 2
Example 113Z6 2.3 2
Example 114Z6 2.3 2
Example 115Z6 2.3 2
Example 116Z6 2.3 3
Example 117Z6 2.3 3
[ Table 6Z6]
TABLE 6Z6
Film thickness (mum) Phase difference value (nm)
Example 118Z6 2.3 2
Example 119Z6 2.3 3
Example 120Z6 2.3 2
Example 121Z6 2.3 2
Example 122Z6 2.3 2
Example 123Z6 2.3 2
Example 124Z6 2.3 2
Example 125Z6 2.3 3
Example 126Z6 2.3 2
Example 127Z6 2.3 2
Example 128Z6 2.3 2
Example 129Z6 2.3 2
Example 130Z6 2.3 3
Example 131Z6 2.3 3
Example 132Z6 2.3 2
Example 133Z6 2.3 2
Example 134Z6 2.3 3
[ Table 7Z6]
TABLE 7Z6
Film thickness (mum) Phase difference value (nm)
Example 135Z6 2.3 2
Example 136Z6 2.3 2
Example 137Z6 2.3 2
Example 138Z6 2.3 2
Example 139Z6 2.3 2
Example 140Z6 2.3 2
Example 141Z6 2.3 2
Example 142Z6 2.3 3
Example 143Z6 2.3 2
Example 144Z6 2.3 2
Example 145Z6 2.3 2
Example 146Z6 2.3 2
Example 147Z6 2.3 2
Example 148Z6 2.3 2
Example 149Z6 2.3 2
Example 150Z6 2.3 2
Example 151Z6 2.3 2
[ Table 8Z6]
TABLE 8Z6
Film thickness (mum) Phase difference value (nm)
Comparative example 1Z6 2.3 15
Comparative example 2Z6 2.3 15
Comparative example 3Z6 2.3 15
Example 152Z6
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 6) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 6: 50 parts of a compound represented by the formula (IFZ6-4),
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by formula (IFZ6-4) was dispersed using a bead mill to obtain a coloring composition. Next, the following were mixed to obtain colored curable composition 52Z6,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 6);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z6 except that a colored curable composition 52Z6 was used instead of the colored curable composition 1Z 6. A colored coating film was obtained in the same manner as in example 101Z6 except that a colored curable composition 52Z6 was used in place of the colored curable composition 1Z6, and the film thickness and the retardation value were measured. The results are shown in Table 9Z 6.
Example 153Z6 to example 168Z6
A colored pattern was obtained in the same manner as in example 152Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the colorant shown in the column of "colorant" in table 9Z 6. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 6.
Example 169Z6 to example 185Z6
A colored pattern was obtained in the same manner as in example 152Z6, except that the compound represented by formula (IFZ6-4) was replaced with the compound shown in the column of "colorant" in table 10Z6, and that c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 10Z 6.
Example 186Z6 to example 202Z6
A colored pattern was obtained in the same manner as in example 152Z6, except that the compound represented by formula (IFZ6-4) was replaced with the compound shown in the column of "colorant" in table 11Z6, and that c.i. pigment green 58 was replaced with c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 11Z 6.
[ Table 9Z6]
TABLE 9Z6
Film thickness (mum) Phase difference value (nm)
Example 186Z6 A compound represented by the formula (IFZ6-4) 2.3 3
Example 187Z6 A compound represented by the formula (IFZ6-2) 2.3 3
Example 188Z6 A compound represented by the formula (IFZ6-3) 2.3 3
Example 189Z6 A compound represented by the formula (IFZ6-6) 2.3 3
Example 190Z6 A compound represented by the formula (IFZ6-10) 2.3 3
Example 191Z6 A compound represented by the formula (IFZ6-11) 2.3 3
Example 192Z6 A compound represented by the formula (IFZ6-12) 2.3 3
Example 193Z6 A compound represented by the formula (IFZ6-31) 2.3 3
Example 194Z6 A compound represented by the formula (IJZ6-1) 2.3 3
Example 195Z6 A compound represented by the formula (IJZ6-2) 2.3 3
Example 196Z6 A compound represented by the formula (IJZ6-3) 2.3 3
Example 197Z6 A compound represented by the formula (IJZ6-4) 2.3 3
Example 198Z6 A compound represented by the formula (IJZ6-6) 2.3 3
Example 199Z6 A compound represented by the formula (IJZ6-10) 2.3 3
Example 200Z6 A compound represented by the formula (IJZ6-11) 2.3 3
Example 201Z6 A compound represented by the formula (IJZ6-12) 2.3 3
Example 202Z6 A compound represented by the formula (IJZ6-31) 2.3 3
[ Table 10Z6]
TABLE 10Z6
Film thickness (mum) Phase difference value (nm)
Example 169Z6 A compound represented by the formula (IFZ6-4) 2.3 3
Example 170Z6 A compound represented by the formula (IFZ6-2) 2.3 3
Example 171Z6 A compound represented by the formula (IFZ6-3) 2.3 3
Example 172Z6 A compound represented by the formula (IFZ6-6) 2.3 3
Example 173Z6 A compound represented by the formula (IFZ6-10) 2.3 3
Example 174Z6 A compound represented by the formula (IFZ6-11) 2.3 3
Example 175Z6 A compound represented by the formula (IFZ6-12) 2.3 3
Example 176Z6 A compound represented by the formula (IFZ6-31) 2.3 3
Example 177Z6 A compound represented by the formula (IJZ6-1) 2.3 3
Example 178Z6 A compound represented by the formula (IJZ6-2) 2.3 3
Example 179Z6 A compound represented by the formula (IJZ6-3) 2.3 3
Example 180Z6 A compound represented by the formula (IJZ6-4) 2.3 3
Example 181Z6 A compound represented by the formula (IJZ6-6) 2.3 3
Example 182Z6 A compound represented by the formula (IJZ6-10) 2.3 3
Example 183Z6 A compound represented by the formula (IJZ6-11) 2.3 3
Example 184Z6 A compound represented by the formula (IJZ6-12) 2.3 3
Example 185Z6 A compound represented by the formula (IJZ6-31) 2.3 3
[ Table 11Z6]
TABLE 11Z6
Film thickness (mum) Phase difference value (nm)
Example 186Z6 A compound represented by the formula (IFZ6-4) 2.3 3
Example 187Z6 A compound represented by the formula (IFZ6-2) 2.3 3
Example 188Z6 A compound represented by the formula (IFZ6-3) 2.3 3
Example 189Z6 A compound represented by the formula (IFZ6-6) 2.3 3
Example 190Z6 A compound represented by the formula (IFZ6-10) 2.3 3
Example 191Z6 A compound represented by the formula (IFZ6-11) 2.3 3
Example 192Z6 A compound represented by the formula (IFZ6-12) 2.3 3
Example 193Z6 A compound represented by the formula (IFZ6-31) 2.3 3
Example 194Z6 A compound represented by the formula (IJZ6-1) 2.3 3
Example 195Z6 A compound represented by the formula (IJZ6-2) 2.3 3
Example 196Z6 A compound represented by the formula (IJZ6-3) 2.3 3
Example 197Z6 A compound represented by the formula (IJZ6-4) 2.3 3
Example 198Z6 A compound represented by the formula (IJZ6-6) 2.3 3
Example 199Z6 A compound represented by the formula (IJZ6-10) 2.3 3
Example 200Z6 A compound represented by the formula (IJZ6-11) 2.3 3
Example 201Z6 A compound represented by the formula (IJZ6-12) 2.3 3
Example 202Z6 A compound represented by the formula (IJZ6-31) 2.3 3
In example Z6, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Industrial applicability
The coloring composition and the compound of the present invention can be used for forming a color filter having a small phase difference value, and thus can be suitably used for a display device such as a color filter and a liquid crystal display device.

Claims (13)

1. A coloring composition comprising:
an alkali-soluble resin, and
a compound represented by formula (IZ 3);
Figure FDA0003121580670000011
in the formula (IZ3), R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z3and R3Z3、R3Z3And R4Z3And R4Z3And R5Z3May be bonded to each other to form a ring;
R101Z3represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z3represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z3、R102Z3and when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
2. The coloring composition according to claim 1, wherein R1Z3、R6Z3And R7Z3Is a hydrogen atom.
3. The coloring composition according to claim 1 or 2, wherein R2Z3、R3Z3、R4Z3And R5Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z3And R3Z3、R3Z3And R 4Z3And R4Z3And R5Z3At least one group of them is bonded to form a ring.
4. A coloring composition according to any one of claims 1 to 3, wherein R2Z3、R3Z3、R4Z3And R5Z3At least one of which is nitro or tert-butyl.
5. The coloring composition according to any one of claims 1 to 4, further comprising a solvent.
6. The coloring composition according to any one of claims 1 to 5, further comprising a yellow colorant or a green colorant.
7. A colored curable composition comprising a polymerizable compound and the colored composition according to any one of claims 1 to 6.
8. The colored curable composition according to claim 7, further comprising a polymerization initiator.
9. A color filter comprising the colored composition according to any one of claims 1 to 6 or the colored curable composition according to claim 7 or 8.
10. A liquid crystal display device comprising the color filter of claim 9.
11. A compound represented by the formula (IZ 3-B);
Figure FDA0003121580670000021
in the formula (IZ3-B), R1Z3、R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3May be bonded to each other to form a ring;
wherein R is21Z3、R31Z3、R41Z3And R51Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3At least one group of them is bonded to form a ring;
R101Z3represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z3represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z3、R102Z3and when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
12. The compound of claim 11Wherein R is1Z3、R61Z3And R71Z3Is a hydrogen atom.
13. The compound of claim 11 or 12, wherein R21Z3、R31Z3、R41Z3And R51Z3At least one of which is nitro or tert-butyl.
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