Pigment composition, inkjet recording method, image recorded material, and pigment compound

Abstract

The present invention provides a pigment composition comprising a pigment compound represented by the following formula 1 and a medium. In formula 1, Cy is an anion part, and X 1 Represents an organic cation represented by the following formula 2-1, etc. (about T 1 、T 2 , R 1 , R 2 and n, the description is omitted. ). B 11 Each independently represents a divalent linking group (with respect to A 11 , A 12 , R 1a , R 1b , R 1c , R 1d 、E 11 、E 12 , m1, description omitted. ).

Description

Technical Field

[0001] The present invention relates to a pigment composition, an inkjet recording method, an image recorded material and a pigment compound. Background Art

[0002] In recent years, it has been proposed to expand near-infrared absorbing pigments to various uses that utilize their characteristics. For example, near-infrared absorbing pigments are used in optical films such as infrared cutoff filters and heat ray shielding films for plasma displays or CCDs (imaging elements); photothermal conversion materials for write-once optical discs or flash fusing materials; information display materials such as anti-counterfeiting inks and invisible barcode inks; and medical materials such as diagnostic markers and photodynamic therapy agents. As a unique performance of near-infrared absorbing pigments, it is required to have strong absorption in the near-infrared or infrared region while having as little absorption as possible in the visible light region (invisibility). In addition, it is also required to maintain infrared absorption ability for a long time.

[0003] For example, Japanese Patent Publication No. 2000-292758 records a compound consisting of a cyanine pigment part having a sulfonic group and bipyridine. Japanese Patent Publication No. 2002-90521 records a cyanine dye in which a cyanine pigment part having a sulfonic group and a potassium cation form an intramolecular salt. Japanese Patent Publication No. 2000-141898 records a compound consisting of a cyanine cation and an anion. Summary of the invention

[0004] Technical issues to be solved by the invention

[0005] Near-infrared absorbing dyes are required to have excellent invisibility and to maintain infrared absorbing ability for a longer period of time than before.

[0006] The present invention has been made in view of the above circumstances, and according to one embodiment of the present invention, provides a dye composition and an inkjet recording method capable of obtaining an image recorded material having excellent invisibility and maintaining infrared absorption capability for a longer period than before.

[0007] According to another embodiment of the present invention, there is provided an image record having excellent invisibility and capable of maintaining infrared absorption for a longer period of time than before.

[0008] According to another embodiment of the present invention, there is provided a novel dye compound capable of obtaining an image record having excellent invisibility and maintaining infrared absorption capability for a longer period than before.

[0009] Means for solving technical problems

[0010] The present invention includes the following aspects.

[0011] <1> A pigment composition comprising a pigment compound represented by the following formula 1 and a medium.

[0012] [Chemical formula 1]

[0013]

[0014] In formula 1, L 1 Represents a methine chain consisting of an odd number of methines. 1 and R 2 Each independently represents an aliphatic group or an aromatic group. 1 and T 2 Each independently represents a non-metallic atom group forming a 5-membered or 6-membered nitrogen-containing heterocyclic ring which may be fused. Cy is an anion part, X 1 represents an organic cation represented by the following Formula 2-1, Formula 2-2 or Formula 2-3 or an organic cation having a structure represented by Formula 2-4. n represents a non-zero number required for neutralizing charges.

[0015] [Chemical formula 2]

[0016]

[0017] [Chemical formula 3]

[0018]

[0019] [Chemical formula 4]

[0020]

[0021] [Chemical formula 5]

[0022]

[0023] In formula 2-1, A 11 and A 12 Each independently represents a nitrogen atom or a phosphorus atom. 11 R each independently represents a divalent linking group. 1a , R 1b , R 1c , R 1d 、E 11 and E 12 R each independently represents an aliphatic group or an aromatic group. 1a , R 1b , R 1c and R 1d They may be bonded to each other to form a ring. m1 is an integer greater than or equal to 1.

[0024] In formula 2-2, A 21 , A 22 and A23 Each independently represents a nitrogen atom or a phosphorus atom. 21 and B 22 R each independently represents a divalent linking group. 2a and R 2b Each independently represents an aliphatic group or an aromatic group. m2 is an integer greater than 0. 21 Indicates that the ring contains A 21 A group of non-metallic atoms in an aromatic ring. 22 Indicates that the ring contains A 23 An aromatic ring of non-metallic atoms.

[0025] In formula 2-3, A 31 and A 32 Each independently represents a nitrogen atom or a phosphorus atom. 31 Represents a divalent linking group. 3a and R 3b Each independently represents an aliphatic group or an aromatic group. 31 Indicates that the ring contains A 31 A group of non-metallic atoms in an aromatic ring. 32 Indicates that the ring contains A 32 An aromatic ring of non-metallic atoms.

[0026] In formula 2-4, A 41 Each independently represents a nitrogen atom or a phosphorus atom. 41 R each independently represents a single bond or a divalent linking group. 4a , R 4b and R 4c Each independently represents an aliphatic group or an aromatic group. 41 and E 42 R each independently represents a single bond or an aliphatic group. 4a , R 4b and R 4c One of them can be combined with E 41 or E 42 m4 is an integer greater than or equal to 2.

[0027] <2> The pigment composition according to <1>, wherein

[0028] In Formula 2-1, Formula 2-2 and Formula 2-3, B 11 , B 21 , B 22 and B 31 Each independently is a divalent linking group having 2 to 8 carbon atoms.

[0029] <3> The pigment composition according to <1> or <2>, wherein

[0030] In Formula 2-1, Formula 2-2, Formula 2-3 and Formula 2-4, A 11 , A 12 , A 21 , A 22 , A 23 , A 31 , A 32 and A 41 A nitrogen atom.

[0031] <4> The pigment composition according to any one of <1> to <3>, wherein

[0032] In formula 1, X 1 represents an organic cation represented by Formula 2-1 or an organic cation having a structure represented by Formula 2-4.

[0033] <5> The pigment composition according to any one of <1> to <4>, wherein

[0034] In Formula 1, Cy is represented by the following Formula 4.

[0035] [Chemical formula 6]

[0036]

[0037] In formula 4, Y 1 and Y 2 Represent CR independently 3 R 4 -, -O-, -S-, -Se-, or -NR 5 -. R 3 , R 4 and R 5 R each independently represents a hydrogen atom, an aliphatic group or an aromatic ring group. 3 and R 4 They may be bonded to each other to form a ring. 1 and A 2 Each independently represents a non-metallic atom group forming an aromatic ring or an aromatic heterocyclic ring. 2 Each independently represents a methine chain consisting of 1, 2 or 3 methine groups, L 2 It has no substituent. 6 and R 7 R each independently represents a hydrogen atom or an aliphatic group. 6 and R 7 Can be linked to each other to form a ring. 8 It is represented by the following formula A.

[0038] -S A -T A Formula A

[0039] In formula A, S A represents a single bond, alkylene, alkenylene, alkynylene, -O-, -S-, -NR L1 -, -C(=O)-, -C(=O)O-, -C(=O)NR L1 -、-S(=O) 2 -、-OR L2 - or a group consisting of at least two of these, R L1 Each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and R L2 represents an alkylene group, an arylene group or a divalent heterocyclic group, T A represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a cyano group, a hydroxyl group, a formyl group, a carboxyl group, an amino group, a thiol group, a sulfone group, a phosphoryl group, a boryl group, a vinyl group, an ethynyl group, a trialkylsilyl group or a trialkoxysilyl group.

[0040] <6> The pigment composition according to <5>, wherein

[0041] In formula 4, A 1 and A 2 Each independently represents a non-metal atom group forming a benzene ring or a naphthalene ring.

[0042] <7> The pigment composition according to any one of <1> to <6>, wherein

[0043] The medium is liquid.

[0044] <8> The pigment composition according to any one of <1> to <7>, wherein

[0045] The medium is an aqueous liquid.

[0046] <9> The pigment composition according to any one of <1> to <8>, wherein

[0047] The medium contains water and an organic solvent having a boiling point of 100° C. or higher.

[0048] <10> The pigment composition according to any one of <1> to <9>, which is an ink.

[0049] <11> The dye composition according to <10>, which is used for inkjet recording.

[0050] <12> An inkjet recording method comprising the step of providing the dye composition according to <11> on a substrate.

[0051] <13> An image record comprising:

[0052] substrate; and

[0053] The cured product of the dye composition according to <10> or <11> disposed on a substrate, namely, an infrared absorption image.

[0054] <14> An image recorded material comprising a substrate and an infrared absorption image disposed on the substrate, wherein the infrared absorption image comprises a pigment compound represented by the following formula 1, and the maximum absorption wavelength of the infrared absorption image is within a range of 700 nm to 1300 nm.

[0055] [Chemical formula 7]

[0056]

[0057] In formula 1, L 1 Represents a methine chain consisting of an odd number of methines. 1 and R 2 Each independently represents an aliphatic group or an aromatic group. 1 and T 2 Each independently represents a non-metallic atom group forming a 5-membered or 6-membered nitrogen-containing heterocyclic ring which may be fused. Cy is an anion part, X 1 represents an organic cation represented by the following Formula 2-1, Formula 2-2 or Formula 2-3 or an organic cation having a structure represented by Formula 2-4. n represents a non-zero number required for neutralizing charges.

[0058] [Chemical formula 8]

[0059]

[0060] [Chemical formula 9]

[0061]

[0062] [Chemical formula 10]

[0063]

[0064] [Chemical formula 11]

[0065]

[0066] In formula 2-1, A 11 and A 12 Each independently represents a nitrogen atom or a phosphorus atom. 11 R each independently represents a divalent linking group. 1a , R 1b , R 1c , R 1d 、E 11 and E 12 R each independently represents an aliphatic group or an aromatic group. 1a , R1b , R 1c and R 1d They may be bonded to each other to form a ring. m1 is an integer greater than or equal to 1.

[0067] In formula 2-2, A 21 , A 22 and A 23 Each independently represents a nitrogen atom or a phosphorus atom. 21 and B 22 R each independently represents a divalent linking group. 2a and R 2b Each independently represents an aliphatic group or an aromatic group. m2 is an integer greater than 0. 21 Indicates that the ring contains A 21 A group of non-metallic atoms in an aromatic ring. 22 Indicates that the ring contains A 23 An aromatic ring of non-metallic atoms.

[0068] In formula 2-3, A 31 and A 32 Each independently represents a nitrogen atom or a phosphorus atom. 31 Represents a divalent linking group. 3a and R 3b Each independently represents an aliphatic group or an aromatic group. 31 Indicates that the ring contains A 31 A group of non-metallic atoms in an aromatic ring. 32 Indicates that the ring contains A 32 An aromatic ring of non-metallic atoms.

[0069] In formula 2-4, A 41 Each independently represents a nitrogen atom or a phosphorus atom. 41 R each independently represents a single bond or a divalent linking group. 4a , R 4b and R 4c Each independently represents an aliphatic group or an aromatic group. 41 and E 42 R each independently represents a single bond or an aliphatic group. 4a , R 4b and R 4c One of them can be combined with E 41 or E 42 m4 is an integer greater than or equal to 2.

[0070] <15> A pigment compound represented by the following formula 1.

[0071] [Chemical formula 12]

[0072]

[0073] In formula 1, L 1 Represents a methine chain consisting of an odd number of methines. 1 and R 2 Each independently represents an aliphatic group or an aromatic group. 1 and T 2 Each independently represents a non-metallic atom group forming a 5-membered or 6-membered nitrogen-containing heterocyclic ring which may be fused. Cy is an anion part, X 1 represents an organic cation represented by the following Formula 2-1, Formula 2-2 or Formula 2-3 or an organic cation having a structure represented by Formula 2-4. n represents a non-zero number required for neutralizing charges.

[0074] [Chemical formula 13]

[0075]

[0076] [Chemical formula 14]

[0077]

[0078] [Chemical formula 15]

[0079]

[0080] [Chemical formula 16]

[0081]

[0082] In formula 2-1, A 11 and A 12 Each independently represents a nitrogen atom or a phosphorus atom. 11 R each independently represents a divalent linking group. 1a , R 1b , R 1c , R 1d 、E 11 and E 12 R each independently represents an aliphatic group or an aromatic group. 1a , R 1b , R 1c and R 1d They may be bonded to each other to form a ring. m1 is an integer greater than or equal to 1.

[0083] In formula 2-2, A 21 , A 22 and A 23 Each independently represents a nitrogen atom or a phosphorus atom. 21 and B 22 R each independently represents a divalent linking group. 2a and R2b Each independently represents an aliphatic group or an aromatic group. m2 is an integer greater than 0. 21 Indicates that the ring contains A 21 A group of non-metallic atoms in an aromatic ring. 22 Indicates that the ring contains A 23 An aromatic ring of non-metallic atoms.

[0084] In formula 2-3, A 31 and A 32 Each independently represents a nitrogen atom or a phosphorus atom. 31 Represents a divalent linking group. 3a and R 3b Each independently represents an aliphatic group or an aromatic group. 31 Indicates that the ring contains A 31 A group of non-metallic atoms in an aromatic ring. 32 Indicates that the ring contains A 32 An aromatic ring of non-metallic atoms.

[0085] In formula 2-4, A 41 Each independently represents a nitrogen atom or a phosphorus atom. 41 R each independently represents a single bond or a divalent linking group. 4a , R 4b and R 4c Each independently represents an aliphatic group or an aromatic group. 41 and E 42 R each independently represents a single bond or an aliphatic group. 4a , R 4b and R 4c One of them can be combined with E 41 or E 42 m4 is an integer greater than or equal to 2.

[0086] <16> The pigment compound according to <15>, wherein

[0087] In Formula 2-1, Formula 2-2 and Formula 2-3, B 11 , B 21 , B 22 and B 31 Each independently is a divalent linking group having 2 to 8 carbon atoms.

[0088] <17> The pigment compound according to <15> or <16>, wherein

[0089] In Formula 2-1, Formula 2-2, Formula 2-3 and Formula 2-4, A 11 , A 12 , A 21 , A22 , A 23 , A 31 , A 32 and A 41 A nitrogen atom.

[0090] <18> The pigment compound according to any one of <15> to <17>, wherein

[0091] In formula 1, X 1 represents an organic cation represented by Formula 2-1 or an organic cation having a structure represented by Formula 2-4.

[0092] <19> The pigment compound according to any one of <15> to <18>, wherein

[0093] In Formula 1, Cy is represented by the following Formula 4.

[0094] [Chemical formula 17]

[0095]

[0096] In formula 4, Y 1 and Y 2 Represent CR independently 3 R 4 -, -O-, -S-, -Se-, or -NR 5 -. R 3 , R 4 and R 5 R each independently represents a hydrogen atom, an aliphatic group or an aromatic ring group. 3 and R 4 They may be bonded to each other to form a ring. 1 and A 2 Each independently represents a non-metallic atom group forming an aromatic ring or an aromatic heterocyclic ring. 2 Each independently represents a methine chain consisting of 1, 2 or 3 methine groups, L 2 It has no substituent. 6 and R 7 R each independently represents a hydrogen atom or an aliphatic group. 6 and R 7 Can be linked to each other to form a ring. 8 It is represented by the following formula A.

[0097] -S A -T A Formula A

[0098] In formula A, S A represents a single bond, alkylene, alkenylene, alkynylene, -O-, -S-, -NR L1-, -C(=O)-, -C(=O)O-, -C(=O)NR L1 -、-S(=O) 2 -、-OR L2 - or a group consisting of at least two of these, R L1 Each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and R L2 represents an alkylene group, an arylene group or a divalent heterocyclic group, T A represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a cyano group, a hydroxyl group, a formyl group, a carboxyl group, an amino group, a thiol group, a sulfone group, a phosphoryl group, a boryl group, a vinyl group, an ethynyl group, a trialkylsilyl group or a trialkoxysilyl group.

[0099] <20> The pigment compound according to <19>, wherein

[0100] In formula 4, A 1 and A 2 Each independently represents a non-metal atom group forming a benzene ring or a naphthalene ring.

[0101] Effects of the Invention

[0102] According to the present invention, there are provided a dye composition and an inkjet recording method capable of obtaining an image recorded material having excellent invisibility and maintaining infrared absorption capability for a longer period than before.

[0103] Furthermore, according to the present invention, there is provided an image recorded material which is excellent in invisibility and has an infrared absorption capability which is maintained for a longer period of time than before.

[0104] Furthermore, according to the present invention, there is provided a novel dye compound capable of obtaining an image recorded material having excellent invisibility and maintaining infrared absorption capability for a longer period than before. DETAILED DESCRIPTION

[0105] Hereinafter, the dye composition, inkjet recording method, image recorded material, and dye compound of the present invention will be described in detail.

[0106] In the present specification, a numerical range expressed using "to" indicates a range including the numerical values ​​described before and after "to" as the minimum value and the maximum value, respectively.

[0107] In the numerical ranges recorded in this specification, the upper limit or lower limit recorded in a certain numerical range can be replaced by the upper limit or lower limit of other numerical ranges recorded in other stages. In addition, in the numerical ranges recorded in this specification, the upper limit or lower limit recorded in a certain numerical range can also be replaced by the value shown in the embodiments.

[0108] In the present specification, when a plurality of substances corresponding to each component are present in the composition, the amount of each component in the composition means the total amount of the plurality of substances present in the composition unless otherwise specified.

[0109] In the present specification, a combination of two or more preferred aspects is a more preferred aspect.

[0110] In the present specification, the term "process" includes not only an independent process but also a process that cannot be clearly distinguished from other processes as long as the intended purpose of the process can be achieved.

[0111] In this specification, "(meth)acrylate" is a concept including both acrylate and methacrylate. Also, "(meth)acrylic acid" is a concept including both acrylic acid and methacrylic acid.

[0112] In the present specification, a monovalent heterocyclic group refers to a group formed by removing one hydrogen atom from a heterocyclic compound, and a divalent heterocyclic group refers to a group formed by removing two hydrogen atoms from a heterocyclic compound.

[0113] [Pigment compound]

[0114] The pigment compound of the present invention is represented by Formula 1 below.

[0115] [Chemical formula 18]

[0116]

[0117] In formula 1, L 1 Represents a methine chain consisting of an odd number of methines. 1 and R 2 Each independently represents an aliphatic group or an aromatic group. 1 and T 2 Each independently represents a non-metallic atom group forming a 5-membered or 6-membered nitrogen-containing heterocyclic ring which may be fused. Cy is an anion part, X 1 represents an organic cation represented by the following Formula 2-1, Formula 2-2 or Formula 2-3 or an organic cation having a structure represented by Formula 2-4. n represents a non-zero number required for neutralizing charges.

[0118] [Chemical formula 19]

[0119]

[0120] [Chemical formula 20]

[0121]

[0122] [Chemical formula 21]

[0123]

[0124] [Chemical formula 22]

[0125]

[0126] In formula 2-1, A 11 and A 12 Each independently represents a nitrogen atom or a phosphorus atom. 11 R each independently represents a divalent linking group. 1a , R 1b , R 1c , R 1d 、E 11 and E 12 R each independently represents an aliphatic group or an aromatic group. 1a , R 1b , R 1c and R 1d They may be bonded to each other to form a ring. m1 is an integer greater than or equal to 1.

[0127] In formula 2-2, A 21 , A 22 and A 23 Each independently represents a nitrogen atom or a phosphorus atom. 21 and B 22 R each independently represents a divalent linking group. 2a and R 2b Each independently represents an aliphatic group or an aromatic group. m2 is an integer greater than 0. 21 Indicates that the ring contains A 21 Aromatic ring of non-metallic atoms. 22 Indicates that the ring contains A 23 An aromatic ring of non-metallic atoms.

[0128] In formula 2-3, A 31 and A 32 Each independently represents a nitrogen atom or a phosphorus atom. 31 Represents a divalent linking group. 3a and R 3b Each independently represents an aliphatic group or an aromatic group. 31 Indicates that the ring contains A 31 Aromatic ring of non-metallic atoms. 32 Indicates that the ring contains A 32 An aromatic ring of non-metallic atoms.

[0129] In formula 2-4, A 41 Each independently represents a nitrogen atom or a phosphorus atom. 41R each independently represents a single bond or a divalent linking group. 4a , R 4b and R 4c Each independently represents an aliphatic group or an aromatic group. 41 and E 42 R each independently represents a single bond or an aliphatic group. 4a , R 4b and R 4c One of them can be combined with E 41 or E 42 m4 is an integer greater than or equal to 2.

[0130] The pigment compound represented by Formula 1 has excellent infrared absorption ability and little absorption in the visible region, and thus has excellent invisibility. In addition, the infrared absorption ability of the pigment compound represented by Formula 1 can be maintained for a longer period of time than before.

[0131] Cyanine pigments easily form associated complexes. When cyanine pigments form associated complexes, they absorb light of long wavelength, so they are invisibly excellent and have excellent durability such as light resistance and resistance to moisture and heat. The pigment compound represented by Formula 1 has a cyanine pigment structure and an organic cation represented by Formula 2-1, Formula 2-2 or Formula 2-3 or an organic cation with a structure represented by Formula 2-4. These organic cations have a soft molecular structure, so it is inferred that the effect of linking cyanine pigments to each other at the position that can properly form an associated complex is high. As a result, it is believed that the cyanine pigments of the use of organic cations of the present application can improve the ability to form associations in the pigment composition, and the infrared absorption ability can be maintained for a longer time than in the past.

[0132] In the past, it is known that there is a pigment compound that forms a salt with the cyanine dye structure as a cationic portion and a counter anion; and a pigment compound that forms a salt with the cyanine dye structure as an anionic portion and a metal cation (for example, Japanese Patent Publication No. 2002-90521 and Japanese Patent Publication No. 2000-141898). However, these pigment compounds are difficult to form an association in a pigment composition, and the maintenance of infrared absorption ability can not be expected.

[0133] And, record a kind of pigment compound that forms salt by the cyanine dye structure as anion portion and the organic cation with bipyridine skeleton in Japanese Unexamined Patent Publication 2000-292758 communique.Yet, because bipyridine skeleton has rigid molecular structure, it is low to therefore infer that the effect of linking cyanine dye each other at the position that can suitably form associated compound.As a result, use the cyanine dye of the organic cation with bipyridine skeleton to be difficult for forming associated compound in pigment composition, can not expect the maintenance of infrared absorption ability.

[0134] Hereinafter, the dye compound represented by Formula 1 will be described in detail.

[0135] [Chemical formula 23]

[0136]

[0137] In formula 1, L 1 Represents a methine chain consisting of an odd number of methines. 1 and R 2 Each independently represents an aliphatic group or an aromatic group. 1 and T 2 Each independently represents a non-metallic atom group forming a 5-membered or 6-membered nitrogen-containing heterocyclic ring which may be fused. Cy is an anion part, X 1 represents an organic cation represented by the following Formula 2-1, Formula 2-2 or Formula 2-3 or an organic cation having a structure represented by Formula 2-4. n represents a non-zero number required for neutralizing charges.

[0138] [L 1 ]

[0139] In formula 1, L 1 Represents a methine chain consisting of an odd number of methines. 1 It preferably represents a methine chain consisting of 5, 7 or 9 methine groups, and more preferably represents a methine chain consisting of 5 or 7 methine groups.

[0140] The central methine group of the methine chain preferably has a substituent represented by Formula A. A and T A , which will be explained later.

[0141] *-S A -T A Formula A

[0142] The methine groups other than the central methine group in the methine chain may have a substituent, but preferably have no substituent.

[0143] The methine chain may have a cross-linked structure at any position. For example, in the methine chain, the carbon atoms constituting the methine chain may bond to each other to form a ring structure. The ring structure is not particularly limited, and is preferably an aliphatic ring, more preferably a 5-membered aliphatic ring or a 6-membered aliphatic ring.

[0144] Specifically, L 1 It is preferably a group represented by the following formula L1-1, L1-2, L2-1 or L2-2, and more preferably a group represented by the following formula L1-2 or L2-2.

[0145] [Chemical formula 24]

[0146]

[0147] In formula L1-1, formula L1-2, formula L2-1 and formula L2-2, A represents a substituent represented by the above formula A, and the wavy line portion independently represents the substituent corresponding to L in formula 1. 1 Bonding positions of structures other than .

[0148] In formula L2-1 and formula L2-2, Y L Y represents a non-metallic atom group forming an aliphatic ring or a heterocyclic ring, and preferably represents a non-metallic atom group forming an aliphatic ring. L It is preferably an alkylene group. Examples of the alkylene group include -CH 2 CH 2 - and - CH 2 C(Z) 2 -CH 2 -. The aliphatic ring is preferably a 5-membered aliphatic ring or a 6-membered aliphatic ring. Z each independently represents a hydrogen atom or an alkyl group. Z is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and more preferably a hydrogen atom or a methyl group. Two Zs may be bonded to form a ring structure.

[0149] The group represented by the above formula L2-1 or L2-2 is preferably a group represented by the following formula L3-1 to formula L3-4.

[0150] [Chemical formula 25]

[0151]

[0152] In formula L3-3 and formula L3-4, Z each independently represents a hydrogen atom or an alkyl group. Z is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and more preferably a hydrogen atom or a methyl group. Two Zs may be bonded to form a ring structure.

[0153] In formula L3-1 to formula L3-4, A represents a substituent represented by the above formula A, and the wavy line portion independently represents the substituent corresponding to L in formula 1. 1 Bonding positions of structures other than .

[0154] In formula A, S A represents a single bond, alkylene, alkenylene, alkynylene, -O-, -S-, -NR L1 -, -C(=O)-, -C(=O)O-, -C(=O)NR L1 -、-S(=O) 2 -、-OR L2 - or a group consisting of at least two of these. From the perspective of invisibility, S A It is preferably a single bond, an alkylene group, an alkenylene group or an alkynylene group, and more preferably a single bond.

[0155] The alkylene group is preferably an alkylene group having 1 to 10 carbon atoms, more preferably an alkylene group having 1 to 4 carbon atoms, and further preferably a methylene group or a vinyl group.

[0156] The alkenylene group is preferably an alkenylene group having 2 to 10 carbon atoms, more preferably an alkenylene group having 2 to 4 carbon atoms, and further preferably an alkenylene group having 2 or 3 carbon atoms.

[0157] The alkynylene group is preferably an alkynylene group having 2 to 10 carbon atoms, more preferably an alkynylene group having 2 to 4 carbon atoms, and further preferably an alkynylene group having 2 or 3 carbon atoms.

[0158] The alkylene group, alkenylene group and alkynylene group may be linear or branched, and a part or all of the carbon atoms contained in each group may form a ring structure.

[0159] Hereinafter, in the description of the alkylene group, alkenylene group and alkynylene group in the present invention, the above contents apply unless otherwise specified.

[0160] In -C(=O)O-, the carbon atom and L 1 Bonded and oxygen atoms with T A bond, or it can be an oxygen atom and L 1 Bonded and carbon atoms with T A Bond.

[0161] -C(=O)NR L1 - can be carbon atoms and L 1 Bonded and nitrogen atom with T A Bonding, or nitrogen atom and L 1 Bonded and carbon atoms with T A Bond.

[0162] In formula A, S A For-NR L1 -or-C(=O)NR L1 -, R L1 It represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and is preferably a hydrogen atom, an alkyl group or an aryl group, and more preferably a hydrogen atom.

[0163] Examples of the halogen atom include a fluorine atom (F atom), a chlorine atom (Cl atom), a bromine atom (Br atom) and an iodine atom (I atom). Among them, the halogen atom is preferably a Cl atom or a Br atom, and more preferably a Cl atom.

[0164] The alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and further preferably an alkyl group having 1 or 2 carbon atoms.

[0165] The aryl group is preferably an aryl group having 6 to 20 carbon atoms, and more preferably a phenyl group or a naphthyl group.

[0166] The heterocyclic ring in the monovalent heterocyclic group is preferably a 5-membered ring or a 6-membered ring. In addition, the heterocyclic ring may form a condensed ring with an aliphatic ring, an aromatic ring or other heterocyclic ring. As the heteroatom in the heterocyclic ring, N atom, O atom and S atom may be mentioned, preferably N atom.

[0167] Examples of the heterocyclic ring include a pyridine ring, a piperidine ring, a furan ring, a furfuran ring, a thiophene ring, a pyrrole ring, a quinoline ring, a morpholine ring, an indole ring, an imidazole ring, a pyrazole ring, a carbazole ring, a phenothiazine ring, a phenoxazine ring, an indoleline ring, a pyrrolidone ring, a thiazole ring, a pyrazine ring, a thiadiazine ring, a benzoquinoline ring and a thiadiazole ring.

[0168] In formula A, S A For-OR L2 -, R L2 represents an alkylene group, an arylene group or a divalent heterocyclic group, and is preferably an alkylene group.

[0169] The alkylene group is preferably an alkylene group having 1 to 10 carbon atoms, more preferably an alkylene group having 1 to 4 carbon atoms, and further preferably an alkylene group having 1 or 2 carbon atoms.

[0170] The arylene group is preferably an arylene group having 6 to 20 carbon atoms, more preferably a phenylene group or a naphthylene group, and further preferably a phenylene group.

[0171] The divalent heterocyclic group is preferably selected from the group consisting of R L1 A structure obtained by further removing one hydrogen from the monovalent heterocyclic group in .

[0172] In formula A, T A represents a halogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a cyano group, a hydroxyl group, a formyl group, a carboxyl group, an amino group, a thiol group, a sulfo group, a phosphoryl group, a boryl group, a vinyl group, an ethynyl group, a trialkylsilyl group or a trialkoxysilyl group. A It is preferably an aryl group, a monovalent heterocyclic group or a trialkylsilyl group.

[0173] Examples of the halogen atom include a fluorine atom (F atom), a chlorine atom (Cl atom), a bromine atom (Br atom) and an iodine atom (I atom). Among them, the halogen atom is preferably a Cl atom or a Br atom, and more preferably a Cl atom.

[0174] The alkyl group is preferably an alkyl group having 1 to 10 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and further preferably an alkyl group having 1 or 2 carbon atoms.

[0175] In formula A, T A When T represents an alkyl group, A It can form a ring structure with other carbon atoms in the methine chain. As the ring structure, a 5-membered ring or a 6-membered ring is preferred.

[0176] The aryl group is preferably an aryl group having 6 to 20 carbon atoms, more preferably a phenyl group or a naphthyl group, and further preferably a phenyl group.

[0177] The heterocyclic ring in the monovalent heterocyclic group is preferably a 5-membered ring or a 6-membered ring. Furthermore, the heterocyclic ring may form a condensed ring with an aliphatic ring, an aromatic ring or another heterocyclic ring.

[0178] Examples of the hetero atom in the heterocyclic ring include a N atom, an O atom and a S atom, and a N atom is preferred.

[0179] Examples of the heterocyclic ring include a pyridine ring, a triazine ring, a piperidine ring, a furan ring, a furfuran ring, a Michaelis acid ring, a barbituric acid ring, a succinimide ring, a thiophene ring, a pyrrole ring, a quinoline ring, a morpholine ring, a thiomorpholine ring, an indole ring, an imidazole ring, a pyrazole ring, a carbazole ring, a phenothiazine ring, a phenoxazine ring, an indoline ring, a pyrrolidone ring, a thiazole ring, a pyrazine ring, a thiadiazine ring, a benzoquinoline ring, and a thiadiazole ring.

[0180] The heterocyclic ring may form a salt structure. For example, a pyridine ring may form a pyridinium salt or exist as a pyridinium ion.

[0181] The aryl group and the monovalent heterocyclic group may have a substituent. Examples of the substituent include an alkyl group, an alkoxy group, a halogen atom, an alkenyl group, an alkynyl group, an aryl group, a monovalent heterocyclic group, a nitro group, a cyano group, -OR T 、-C(=O)R T 、-C(=O)OR T 、-OC(=O)R T 、-N(R T ) 2 、-NHC(=O)R T 、-C(=O)N(R T ) 2 、-NHC(=O)OR T 、-OC(=O)N(R T ) 2 、-NHC(=O)N(R T ) 2 、-SR T 、-S(=O) 2 R T 、-S(=O) 2 OR T 、-NHS(=O) 2 R T and -S(=O) 2 N(R T ) 2 .

[0182] R TEach independently represents a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and is preferably a hydrogen atom, an alkyl group or an aryl group.

[0183] As R T The alkyl group in the group is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and further preferably a methyl group or an ethyl group.

[0184] R T The aryl group in is preferably an aryl group having 6 to 20 carbon atoms, more preferably a phenyl group or a naphthyl group, and further preferably a phenyl group.

[0185] R T The heterocyclic ring in the monovalent heterocyclic group is preferably a 5-membered ring or a 6-membered ring. Furthermore, the heterocyclic ring may form a condensed ring with an aliphatic ring, an aromatic ring or another heterocyclic ring.

[0186] Examples of the hetero atom in the heterocyclic ring include a N atom, an O atom and a S atom, and a N atom is preferred.

[0187] Examples of the heterocyclic ring include a pyridine ring, a piperidine ring, a piperazine ring, a pyrrolidine ring, a furan ring, a tetrahydrofuran ring, a tetrahydropyran ring, a thiophene ring, a pyrrole ring, a quinoline ring, a morpholine ring, an indole ring, an imidazole ring, a pyrazole ring, a carbazole ring, a phenothiazine ring, a phenoxazine ring, an indoline ring, a pyrrolidone ring, a thiazole ring, a pyrazine ring, a thiadiazine ring, a benzoquinoline ring and a thiadiazole ring.

[0188] R T The monovalent heterocyclic group in may further have a substituent. Examples of the substituent include: T The preferred aspects are also the same for the groups represented by .

[0189] Examples of the amino group include an unsubstituted amino group and a substituted amino group, and a diarylamino group or a diheteroarylamino group is preferred.

[0190] Examples of the substituent in the substituted amino group include an alkyl group, an aryl group, and a monovalent heterocyclic group. The meanings of the alkyl group, the aryl group, and the monovalent heterocyclic group in the substituted amino group are the same as those in T A The alkyl group, aryl group or monovalent heterocyclic group in are the same and the preferred aspects are also the same.

[0191] The trialkylsilyl group is preferably a trialkylsilyl group having an alkyl group with 1 to 10 carbon atoms, and more preferably a trialkylsilyl group having an alkyl group with 1 to 4 carbon atoms. Examples of the trialkylsilyl group include trimethylsilyl, dimethylbutylsilyl, triethylsilyl, and triisopropylsilyl.

[0192] The trialkoxysilyl group is preferably a trialkoxysilyl group having an alkoxy group with 1 to 10 carbon atoms, and more preferably a trialkoxysilyl group having an alkoxy group with 1 to 4 carbon atoms. Examples of the trialkoxysilyl group include a trimethoxysilyl group and a triethoxysilyl group.

[0193] S A represents a single bond or an alkylene group and T A When an alkyl group is represented, S A and T A The total number of carbon atoms contained in is preferably 3 or more, more preferably 4 or more, and further preferably 5 or more.

[0194] Furthermore, from the viewpoint of dispersibility, the total number of carbon atoms is preferably 20 or less, and more preferably 10 or less. From the viewpoint of dispersibility, in Formula A, T A Preferred is a heterocyclic group containing a nitrogen atom, an aryl group or a halogen atom.

[0195] Specific examples of the substituent represented by formula A (substituent A) include the following substituents A-1 to A-55. However, the substituent A in the present invention is not limited thereto. In the following substituents A-1 to A-55, iC 10 represents isodecyl, iC 8 represents isooctyl, and * represents the same as L in formula 1 1 bonding part.

[0196] [Chemical formula 26]

[0197]

[0198] [Chemical formula 27]

[0199]

[0200] [Chemical formula 28]

[0201]

[0202] Among the substituents A-1 to A-55, from the viewpoint that the cyanine dye is more likely to form an aggregate, substituents A-1, A-4, A-5, A-8, A-10, A-24, A-34, A-39, A-41 to 43, A-48 or A49 to A55 are preferred.

[0203] The following shows the 1 Specific examples of methine chains represented by L 1 The methine chain represented by is not limited to the following specific examples. In the following specific examples, the wavy lines each independently represent the same as L in Formula 1. 1In addition, Me represents a methyl group, Et represents an ethyl group, and Ph represents a phenyl group.

[0204] [Chemical formula 29]

[0205]

[0206] [Chemical formula 30]

[0207]

[0208] From the viewpoint that cyanine pigments are more likely to form an association, L 1 The methine chain represented by is preferably LA1-LA8, LA11-19, LA21-24 or LA27-30.

[0209] [R 1 and R 2 ]

[0210] R 1 and R 2 Each independently represents an aliphatic group or an aromatic group. The aliphatic group and the aromatic group may have a substituent. As the substituent, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom), a cyano group, a nitro group, an aliphatic group, an aromatic group, a heterocyclic group, -OR 10 、-COR 11 、-COOR 12 、-OCOR 13 、-NR 14 R 15 、-NHCOR 16 、-CONR 17 R 18 、-NHCONR 19 R 20 、-NHCOOR 21 、-SR 22 、-SO 2 R 23 、-SO 2 OR 24 、-NHSO 2 R 25 and SO 2 NR 26 R 27 . R 10 ~R 27 Each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group. Examples thereof include a hydroxyl group, a carboxyl group, a sulfo group, an alkoxy group and an amino group. Among them, the substituent is preferably an aliphatic group, an aromatic group, -OR 10 、-COOR 12 or -SO2 OR 24 , more preferably an aromatic group, -SO 2 OR 24 In addition, -COOR 12 R 12 When it is a hydrogen atom (i.e., a carboxyl group), the hydrogen atom may be dissociated (i.e., a carboxylate group) or in the form of a salt. 2 OR 24 R 24 When it is a hydrogen atom (ie, a sulfo group), the hydrogen atom may be dissociated (ie, a sulfonate group) or may be in the state of a salt.

[0211] Examples of the aliphatic group include an alkyl group, an alkenyl group, an alkynyl group, and an aralkyl group, and examples of the aromatic group include an aryl group.

[0212] By R 1 and R 2 The alkyl group represented by each may be cyclic or chain-shaped. The chain-shaped alkyl group may be a straight-chain alkyl group or a branched alkyl group. The number of carbon atoms of the alkyl group (when having a substituent, the number of carbon atoms of the part excluding the substituent) is preferably 1 to 20, more preferably 1 to 12, and further preferably 1 to 8. Examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, cyclopropyl, cyclohexyl, and 2-ethylhexyl. Examples of the alkyl group having a substituent include 2-hydroxyethyl, 2-carboxyethyl, 2-methoxyethyl, 2-phenoxyethyl, 2-(1-naphthyloxy)ethyl, 2-diethylaminoethyl, 2-sulfoethyl, 2-methoxypropyl, 3-methoxypropyl, 3-sulfopropyl, 3-sulfobutyl, and 4-sulfobutyl.

[0213] By R 1 and R 2 The alkenyl groups represented by each may be cyclic or chained. Chained alkenyl groups may be straight-chain alkenyl groups or branched alkenyl groups. The number of carbon atoms of the alkenyl group (when having a substituent, the number of carbon atoms of the part other than the substituent) is preferably 2 to 20, more preferably 2 to 12, and further preferably 2 to 8. Examples of the alkenyl group include vinyl, allyl, 1-propenyl, 2-butenyl, 2-pentenyl and 2-hexenyl.

[0214] By R 1 and R 2 The alkynyl groups represented by each may be cyclic or chain-shaped. Chain-shaped alkynyl groups may be straight-chain alkynyl groups or branched-chain alkynyl groups. The number of carbon atoms of the alkynyl group (when having a substituent, the number of carbon atoms of the part other than the substituent) is preferably 2 to 20, more preferably 2 to 12, and further preferably 2 to 8. Examples of the alkynyl group include ethynyl and 2-propynyl.

[0215] By R 1and R 2 The alkyl part of each aralkyl group is the same as the above-mentioned alkyl group. The aryl part of the aralkyl group which may have a substituent is the same as the aryl group described below. Examples of the aralkyl group include benzyl and phenethyl.

[0216] By R 1 and R 2 The carbon number of each aryl group (when having a substituent, the carbon number of the portion excluding the substituent) is preferably 6 to 25, more preferably 6 to 15, and even more preferably 6 to 10. Examples of the aryl group include phenyl and naphthyl.

[0217] Examples of the aryl group having a substituent include a 4-carboxyphenyl group, a 4-acetamidophenyl group, a 3-methanesulfonamidophenyl group, a 4-methoxyphenyl group, a 3-carboxyphenyl group, a 3,5-dicarboxyphenyl group, a 4-methanesulfonamidophenyl group, and a 4-butanesulfonamidophenyl group.

[0218] [T 1 and T 2 ]

[0219] T 1 and T 2 Each independently represents a group of non-metal atoms which forms a nitrogen-containing heterocyclic ring which may be condensed into a 5-membered ring or a 6-membered ring.

[0220] Another heterocyclic ring, an aromatic ring, or an aliphatic ring may be condensed to the nitrogen-containing heterocyclic ring.

[0221] The nitrogen-containing heterocyclic ring is preferably a 5-membered ring, and more preferably a benzene ring or a naphthalene ring is fused to the 5-membered nitrogen-containing heterocyclic ring.

[0222] As the nitrogen-containing heterocyclic ring, for example, an oxazole ring, an isoxazole ring, a benzoxazole ring, a naphthooxazole ring, an oxazolocarbazole ring, an oxazolodibenzofuran ring, a thiazole ring, a benzothiazole ring, a naphthothiazole ring, an indolenine ring, a benzoindolenine ring, an imidazole ring, a benzimidazole ring, a naphthoimidazole ring, a quinoline ring, a pyridine ring, a pyrrolopyridine ring, a furanopyrrole ring, an indolizine ring, an imidazoquinoxaline ring, and a quinoxaline ring can be cited. Among them, the nitrogen-containing heterocyclic ring is preferably a quinoline ring, an indolenine ring, a benzoindolenine ring, a benzoxazole ring, a benzothiazole ring, or a benzimidazole ring, and more preferably an indolenine ring, a benzoindolenine ring, a benzothiazole ring, or a benzimidazole ring.

[0223] The nitrogen-containing heterocyclic ring and the ring condensed to the nitrogen-containing heterocyclic ring may have a substituent.

[0224] Examples of the substituent include a halogen atom, a cyano group, a nitro group, an aliphatic group, an aromatic group, a heterocyclic group, -OR 10 、-COR 11 、-COOR 12 、-OCOR 13 、-NR 14 R15 、-NHCOR 16 、-CONR 17 R 18 、-NHCONR 19 R 20 、-NHCOOR 21 、-SR 22 、-SO 2 R 23 、-SO 2 OR 24 、-NHSO 2 R 25 and SO 2 NR 26 R 27 . R 10 ~R 27 Each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group. 12 R 12 When it is a hydrogen atom (i.e., a carboxyl group), the hydrogen atom may be dissociated (i.e., a carboxylate group) or in the form of a salt. 2 OR 24 R 24 When it is a hydrogen atom (i.e., a sulfonic group), the hydrogen atom may be dissociated (i.e., a sulfonic ester group) or in a salt state. Among them, the substituent is preferably -COOR 12 or -SO 2 OR 24 , more preferably -SO 2 OR 24 .

[0225] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0226] As R 10 ~R 27 The aliphatic group and aromatic group represented by each include 1 and R 2 The aliphatic group and the aromatic group represented by each are the same group.

[0227] The heterocyclic group may have a substituent. As the substituent, the substituents which may be possessed by the above-mentioned aliphatic group can be mentioned, and the preferred range is also the same.

[0228] The heterocyclic ring of the heterocyclic group is preferably a 5-membered ring or a 6-membered ring. The heterocyclic ring may be a monocyclic ring or a condensed ring. Examples of the heterocyclic ring include a pyridine ring, a piperidine ring, a furan ring, a furfuran ring, a thiophene ring, a pyrrole ring, a quinoline ring, a morpholine ring, an indole ring, an imidazole ring, a pyrazole ring, a carbazole ring, a phenothiazine ring, a phenoxazine ring, an indoline ring, a thiazole ring, a pyrazine ring, a thiadiazine ring, a benzoquinoline ring, and a thiadiazole ring.

[0229] Among them, the substituent is preferably -COOR 12 or -SO 2 OR 24 , more preferably -SO 2 OR 24 .

[0230] [Cy]

[0231] Cy is an anionic part. Cy has one or more anionic groups to make the anionic part as a whole negatively charged. When the anionic group is a monovalent anionic group, Cy has two or more anionic groups. The position of the anionic group is not particularly limited. The anionic group may be included in L 1 , R 1 and R 2 It can also be included in T 1 and T 2 The anionic group is preferably a sulfo group or a carboxyl group, and more preferably a sulfo group.

[0232] Cy is preferably an anion moiety represented by the following formula 3.

[0233] [Chemical formula 31]

[0234]

[0235] In formula 3, Y 1 and Y 2 Represent CR independently 3 R 4 -, -O-, -S-, -Se-, or -NR 5 -. R 3 , R 4 and R 5 R each independently represents a hydrogen atom, an aliphatic group or an aromatic ring group. 3 and R 4 They may be bonded to each other to form a ring. 1 and A 2 Each independently represents a non-metallic atom group forming an aromatic ring or an aromatic heterocyclic ring. 1 , R 1 and R 2 The meaning is the same as L in formula 1 1 , R1 and R 2 same.

[0236] [Y 1 and Y 2 ]

[0237] Y 1 and Y 2 Represent CR independently 3 R 4 -, -O-, -S-, -Se-, or -NR 5 -.Y 1 and Y 2 Preferably, CR 3 R 4 -, -O-, -S-, more preferably CR 3 R 4 -.

[0238] As R 3 , R 4 and R 5 The aliphatic group and aromatic group represented by each include 1 and R 2 The aliphatic group and the aromatic group represented by each are the same group.

[0239] Among them, R 3 , R 4 and R 5 Each of them is independently preferably an alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, and further preferably 1 to 3. The alkyl group may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group. 3 , R 4 and R 5 Each of them independently is preferably a linear alkyl group or a branched alkyl group, more preferably a linear alkyl group, further preferably a methyl group or an ethyl group, and particularly preferably a methyl group.

[0240] [A 1 and A 2 ]

[0241] A 1 and A 2 Each independently represents a non-metallic atom group forming an aromatic ring or an aromatic heterocyclic ring. The aromatic ring and the aromatic heterocyclic ring may have a substituent.

[0242] As A 1 and A 2 The substituents that the aromatic ring and the aromatic heterocyclic ring formed by each other may have include T in Formula 1. 1 and T 2The substituents that the nitrogen-containing heterocyclic ring formed and the ring condensed therewith may have are the same as those.

[0243] Among them, the substituent is preferably -COOR 12 or -SO 2 OR 24 , more preferably -SO 2 OR 24 .

[0244] As A 1 and A 2 Examples of the aromatic rings formed by each include a benzene ring and a naphthalene ring.

[0245] By A 1 and A 2 The aromatic heterocyclic ring formed by each ring is preferably an aromatic heterocyclic ring in which at least one of the atoms forming the ring is a nitrogen atom, an oxygen atom or a sulfur atom. 1 and A 2 The aromatic heterocyclic ring formed individually may be condensed with another ring (aliphatic ring, aromatic ring or heterocyclic ring).

[0246] By A 1 and A 2 The aromatic heterocyclic rings each formed are preferably 5- to 10-membered rings.

[0247] As A 1 and A 2 Examples of the aromatic heterocyclic ring formed by each of them include a pyridine ring, a dibenzofuran ring, and a carbazole ring.

[0248] From the perspective that cyanine pigments are more likely to form an association, A 1 and A 2 Each of the non-metal atoms independently forms preferably a group of non-metal atoms that forms an aromatic ring, and more preferably a group of non-metal atoms that forms a benzene ring or a naphthalene ring.

[0249] The anion part represented by Formula 3 is preferably an anion part represented by the following Formula 3A or Formula 3B.

[0250] [Chemical formula 32]

[0251]

[0252] [Chemical formula 33]

[0253]

[0254] In Formula 3A, R 1 , R 2 , Y 1 and Y 2 The meaning is the same as R in Formula 3 1 , R 2, Y 1 and Y 2 same.

[0255] V 1A and V 2A Each independently represents a hydrogen atom or a substituent.

[0256] As V 1A and V 2A The substituents represented by each include halogen atoms, cyano groups, nitro groups, aliphatic groups, aromatic groups, heterocyclic groups, -OR 10 、-COR 11 、-COOR 12 、-OCOR 13 、-NR 14 R 15 、-NHCOR 16 、-CONR 17 R 18 、-NHCONR 19 R 20 、-NHCOOR 21 、-SR 22 、-SO 2 R 23 、-SO 2 OR 24 、-NHSO 2 R 25 and SO 2 NR 26 R 27 . R 10 ~R 27 Each independently represents a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group. 12 R 12 When it is a hydrogen atom (i.e., a carboxyl group), the hydrogen atom may be dissociated (i.e., a carboxylate group) or in the form of a salt. 2 OR 24 R 24 When it is a hydrogen atom (ie, a sulfo group), the hydrogen atom may be dissociated (ie, a sulfonate group) or may be in the state of a salt.

[0257] Among them, V 1A and V 2A The substituents represented by each are preferably -COOR 12 or -SO 2 OR 24 , more preferably -SO 2 OR 24 .

[0258] V 1A and V 2AThey may be the same or different from each other, but are preferably the same from the viewpoint of ease of production.

[0259] V 1A When V is a substituent, relative to the benzene ring 1A The bonding position of R is not particularly limited, but is preferably 500 mm away from the bonding to R from the viewpoint that the cyanine pigment is more likely to form an association. 1 The nitrogen atom is farthest away from the 2A When V is a substituent, relative to the benzene ring 2A The bonding position of R is not particularly limited, but is preferably 500 mm away from the bonding to R from the viewpoint that the cyanine pigment is more likely to form an association. 2 The nitrogen atom is farthest away.

[0260] In Formula 3B, R 1 , R 2 , Y 1 and Y 2 The meaning is the same as R in Formula 3 1 , R 2 , Y 1 and Y 2 Same. 1B and V 2B Each independently represents a hydrogen atom or a substituent.

[0261] As V 1B and V 2B The substituents represented by each include those represented by V 1A and V 2A Each represents the same substituent group.

[0262] Among them, V 1B and V 2B The substituents represented by each are preferably -COOR 12 or -SO 2 OR 24 , more preferably -SO 2 OR 24 .

[0263] V 1B and V 2B They may be the same or different from each other, but are preferably the same from the viewpoint of ease of production.

[0264] V 1B When V is a substituent, relative to the naphthalene ring 1B The bonding position of R is not particularly limited, but is preferably 500 mm away from the bonding to R from the viewpoint that the cyanine pigment is more likely to form an association. 1 The nitrogen atom is farthest away from the 2B When V is a substituent, relative to the naphthalene ring 2BThe bonding position of R is not particularly limited, but is preferably 500 mm away from the bonding to R from the viewpoint that the cyanine pigment is more likely to form an association. 2 The nitrogen atom is farthest away.

[0265] From the viewpoint that the cyanine dye is more likely to form an association, Cy is more preferably an anion moiety represented by the following formula 4.

[0266] [Chemical formula 34]

[0267]

[0268] In formula 4, Y 1 and Y 2 Represent CR independently 3 R 4 -, -O-, -S-, -Se-, or -NR 5 -. R 3 , R 4 and R 5 R each independently represents a hydrogen atom, an aliphatic group or an aromatic ring group. 3 and R 4 They may be bonded to each other to form a ring. 1 and A 2 Each independently represents a non-metallic atom group forming an aromatic ring or an aromatic heterocyclic ring. 2 Each independently represents a methine chain consisting of 1, 2 or 3 methine groups, L 2 It has no substituent. 6 and R 7 R each independently represents a hydrogen atom or an aliphatic group. 6 and R 7 Can be linked to each other to form a ring. 8 It is represented by the following formula A.

[0269] -S A -T A Formula A

[0270] In formula A, S A represents a single bond, alkylene, alkenylene, alkynylene, -O-, -S-, -NR L1 -, -C(=O)-, -C(=O)O-, -C(=O)NR L1 -、-S(=O) 2 -、-OR L2 - or a group consisting of at least two of these, R L1 Each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and R L2 represents an alkylene group, an arylene group or a divalent heterocyclic group, T Arepresents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a cyano group, a hydroxyl group, a formyl group, a carboxyl group, an amino group, a thiol group, a sulfone group, a phosphoryl group, a boryl group, a vinyl group, an ethynyl group, a trialkylsilyl group or a trialkoxysilyl group.

[0271] In formula 4, R 1 , R 2 , R 3 , R 4 , R 5 , Y 1 and Y 2 The meaning is the same as R in Formula 3 1 , R 2 , R 3 , R 4 , R 5 , Y 1 and Y 2 same.

[0272] L 2 Each independently represents a methine chain consisting of 1, 2 or 3 methine groups. 2 Preferably, each independently represents a methine chain consisting of one or two methine groups.

[0273] 2 L 2 They may be the same or different from each other, but are preferably the same from the viewpoint of ease of production.

[0274] R 6 and R 7 R each independently represents a hydrogen atom or an aliphatic group. 6 and R 7 R is a hydrogen atom or an aliphatic group, and they are preferably linked to each other to form a ring. 6 and R 7 The ring formed by connecting to each other is preferably a 5-membered aliphatic ring or a 6-membered aliphatic ring. 6 and R 7 Connected to each other -R 6 R 7 -, for example, -CH 2 CH 2 - and - CH 2 C(Z) 2 -CH 2 -. Z is preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and more preferably a hydrogen atom or a methyl group. Two Zs may be bonded to form a ring structure.

[0275] R 8 represents a substituent represented by formula A. Preferred embodiments of the substituent represented by formula A are as described above.

[0276] In the following formula 1, it is shown that 1 Specific examples of basic core 1 and basic core 2 bonded to a methyl chain are represented. For convenience, in formula 1, basic core 1 is recorded as a cationic structure in which the nitrogen atom is cationic, and basic core 2 is recorded as a neutral structure in which the nitrogen atom is uncharged. Since there is a conjugated carbon chain between the nitrogen atom contained in basic core 1 and the nitrogen atom contained in basic core 2, it is considered that the electrons are actually in a delocalized state. Therefore, in formula 1, basic core 1 can also be recorded as a neutral structure and basic core 2 as a cationic structure. In the following specific examples, they are all recorded as cationic structures, but in the pigment compound represented by formula 1, when one basic core is a cationic structure, the other basic core is recorded as a neutral structure. In addition, basic core 1 and basic core 2 are not limited to the following specific examples. In the following specific examples, the wavy lines independently represent the L in formula 1. 1 bonding position.

[0277] [Chemical formula 35]

[0278]

[0279] [Chemical formula 36]

[0280]

[0281] [Chemical formula 37]

[0282]

[0283] In Cy, from the viewpoint of manufacturing ease, basic core 1 and basic core 2 can have the same structure. In addition, basic core 1 and basic core 2 having the same structure means that the constituent atoms are the same and the skeleton is the same. As mentioned above, when basic core 1 and basic core 2 have the same structure, as a structural formula, one of them is recorded as a cationic structure and the other is recorded as a neutral structure.

[0284] From the viewpoint that the cyanine dye can more easily form an aggregate, the basic core 1 and the basic core 2 are preferably TA1 to TA13, TA16, TA28, TA29, or TA31 to TA36.

[0285] [X 1 ]

[0286] X 1 It represents an organic cation represented by the following Formula 2-1, Formula 2-2 or Formula 2-3 or an organic cation having a structure represented by Formula 2-4.

[0287] <Formula 2-1>

[0288] [Chemical formula 38]

[0289]

[0290] In formula 2-1, A 11 and A 12 Each independently represents a nitrogen atom or a phosphorus atom. 11 R each independently represents a divalent linking group. 1a , R 1b , R 1c , R 1d 、E 11 and E 12 R each independently represents an aliphatic group or an aromatic group. 1a , R 1b , R 1c and R 1d They may be bonded to each other to form a ring. m1 is an integer greater than or equal to 1.

[0291] A 11 and A 12 A and B each independently represent a nitrogen atom or a phosphorus atom. 11 and A 12 Preferred is a nitrogen atom.

[0292] A 11 and A 12 They may be the same or different from each other, but are preferably the same from the viewpoint of ease of production.

[0293] B 11 Each independently represents a divalent linking group. 11 The divalent linking group represented by is preferably a group having 2 or more carbon atoms, more preferably a group having 2 to 8 carbon atoms. It is inferred that if the number of carbon atoms is 2 or more, the molecular structure becomes more flexible, so the effect of linking cyanine pigments to each other at a position where an associated complex can be appropriately formed is high. As a result, cyanine pigments are easy to form an associated complex with each other, and tend to maintain infrared absorption ability for a long time.

[0294] As B 11 Examples of the divalent linking group include an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 30 carbon atoms, a heterocyclic linking group, -CH=CH-, -O-, -S-, -C(=O)-, -COO-, -NR-, -CONR-, -OCO-, -SO-, -SO 2 - and a linking group formed by linking two or more of these. R represents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group.

[0295] Among them, B 11 The divalent linking group represented by is preferably an alkylene group. The number of carbon atoms in the alkylene group is preferably 2 to 20, more preferably 2 to 15. The alkylene group is preferably a linear alkylene group.

[0296] R 1a , R 1b , R 1c , R 1d 、E 11 and E 12 Each independently represents an aliphatic group or an aromatic group.

[0297] Examples of the aliphatic group include an alkyl group, an alkenyl group, an alkynyl group, and an aralkyl group, and examples of the aromatic group include an aryl group.

[0298] Among them, R 1a , R 1b , R 1c and R 1d The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms.

[0299] And, E 11 and E 12 Each of them is independently preferably an alkyl group or an aryl group. The number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6. The aryl group is preferably a phenyl group.

[0300] m1 is an integer greater than or equal to 1. m1 is preferably 1 to 3, and more preferably 1 or 2.

[0301] Among them, the organic cation represented by formula 2-1 is more preferably A 11 and A 12 is a nitrogen atom, B 11 is an alkylene group, R 1a , R 1b , R 1c and R 1d is an alkyl group, E 11 and E 12 An organic cation which is an alkyl group.

[0302] Specific examples of the organic cation represented by Formula 2-1 are shown below, but the organic cation represented by Formula 2-1 is not limited to the following specific examples. In addition, Me represents a methyl group, Et represents an ethyl group, and Ph represents a phenyl group.

[0303] [Chemical formula 39]

[0304]

[0305] <Formula 2-2>

[0306] [Chemical formula 40]

[0307]

[0308] In formula 2-2, A 21 , A 22 and A23 Each independently represents a nitrogen atom or a phosphorus atom. 21 and B 22 R each independently represents a divalent linking group. 2a and R 2b Each independently represents an aliphatic group or an aromatic group. m2 is an integer greater than 0. 21 Indicates that the ring contains A 21 A group of non-metallic atoms in an aromatic ring. 22 Indicates that the ring contains A 23 An aromatic ring of non-metallic atoms.

[0309] A 21 , A 22 and A 23 A and B each independently represent a nitrogen atom or a phosphorus atom. 21 , A 22 and A 23 Preferred is a nitrogen atom.

[0310] A 21 , A 22 and A 23 They may be the same or different from each other, but are preferably the same from the viewpoint of ease of production.

[0311] B 21 and B 22 Each independently represents a divalent linking group. 21 and B 22 The divalent linking group represented by is preferably a group having 2 or more carbon atoms, more preferably a group having 2 to 8 carbon atoms. It is inferred that if the number of carbon atoms is 2 or more, the molecular structure becomes more flexible, so the effect of linking cyanine pigments to each other at a position where an associated complex can be appropriately formed is high. As a result, cyanine pigments are easy to form an associated complex with each other, and tend to maintain infrared absorption ability for a long time.

[0312] As B 21 and B 22 Examples of the divalent linking group include an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 30 carbon atoms, a heterocyclic linking group, -CH=CH-, -O-, -S-, -C(=O)-, -COO-, -NR-, -CONR-, -OCO-, -SO-, -SO 2 - and a linking group formed by linking two or more of these. R represents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group.

[0313] Among them, B 21 and B 22The divalent linking groups represented by are each independently preferably an alkylene group. The number of carbon atoms in the alkylene group is preferably 2 to 20, more preferably 2 to 15. The alkylene group is preferably a linear alkylene group.

[0314] R 2a and R 2b Each independently represents an aliphatic group or an aromatic group.

[0315] As R 2a and R 2b Examples of the aliphatic group represented by include alkyl, alkenyl, alkynyl and aralkyl groups. Examples of the aromatic group include aryl groups.

[0316] Among them, R 2a and R 2b Each of them is independently preferably an alkyl group. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms.

[0317] m2 is an integer greater than or equal to 0. m2 is preferably an integer of 0-2.

[0318] G 21 Indicates that the ring contains A 21 Aromatic ring of non-metallic atoms. 22 Indicates that the ring contains A 23 The non-metallic atoms in the aromatic ring. 21 The aromatic ring of is preferably a pyridine ring, an imidazole ring, an oxazole ring or a thiazole ring. 21 The aromatic ring of may be fused with other rings (aliphatic rings, aromatic rings or heterocyclic rings). 23 The aromatic ring of is preferably a pyridine ring, an imidazole ring, an oxazole ring or a thiazole ring. 23 The aromatic ring may be condensed with other rings (aliphatic rings, aromatic rings or heterocyclic rings).

[0319] Among them, the organic cation represented by formula 2-2 is more preferably A 21 , A 22 and A 23 is a nitrogen atom, B 21 and B 22 are independently alkylene, m2 is 0 or 1, G 21 and G 22 It is a pyridine ring, an imidazole ring, an oxazole ring or a thiazole ring.

[0320] Specific examples of the organic cation represented by Formula 2-2 are shown below, but the organic cation represented by Formula 2-2 is not limited to the following specific examples. In addition, Me represents a methyl group.

[0321] [Chemical formula 41]

[0322]

[0323] <Formula 2-3>

[0324] [Chemical formula 42]

[0325]

[0326] In formula 2-3, A 31 and A 32 Each independently represents a nitrogen atom or a phosphorus atom. 31 Represents a divalent linking group. 3a and R 3b Each independently represents an aliphatic group or an aromatic group. 31 Indicates that the ring contains A 31 Aromatic ring of non-metallic atoms. 32 Indicates that the ring contains A 32 An aromatic ring of non-metallic atoms.

[0327] A 31 and A 32 A and B each independently represent a nitrogen atom or a phosphorus atom. 31 and A 32 Preferred is a nitrogen atom.

[0328] A 31 and A 32 They may be the same or different from each other, but are preferably the same from the viewpoint of ease of production.

[0329] B 31 Represents a divalent linking group. 31 The number of carbon atoms of the divalent linking group represented by is preferably 2 or more, more preferably 2 to 8. When the number of carbon atoms is 2 or more, the association formed by the cyanine dyes is held in an appropriate position, and the infrared absorption ability tends to be maintained for a long time.

[0330] As B 31 Examples of the divalent linking group include an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 30 carbon atoms, a heterocyclic linking group, -CH=CH-, -O-, -S-, -C(=O)-, -COO-, -NR-, -CONR-, -OCO-, -SO-, -SO 2 - and a linking group formed by linking two or more of these. R represents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group.

[0331] Among them, B 31The divalent linking group represented by is preferably an alkylene group. The number of carbon atoms in the alkylene group is preferably 2 to 20, more preferably 2 to 15. The alkylene group is preferably a linear alkylene group.

[0332] R 3a and R 3b Each independently represents an aliphatic group or an aromatic group.

[0333] Examples of the aliphatic group include an alkyl group, an alkenyl group, an alkynyl group, and an aralkyl group, and examples of the aromatic group include an aryl group.

[0334] Among them, R 3a and R 3b Each of them is independently preferably an alkyl group. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms.

[0335] G 31 Indicates that the ring contains A 31 Aromatic ring of non-metallic atoms. 32 Indicates that the ring contains A 32 The non-metallic atoms in the aromatic ring. 31 The aromatic ring of is preferably a pyridine ring. 31 The aromatic ring of may be fused with other rings (aliphatic rings, aromatic rings or heterocyclic rings). 32 The aromatic ring of is preferably a pyridine ring. 32 The aromatic ring may be condensed with other rings (aliphatic rings, aromatic rings or heterocyclic rings).

[0336] The organic cation represented by Formula 2-3 is more preferably A 31 and A 32 is a nitrogen atom, B 31 is an alkylene group, R 3a and R 3b are independently alkyl, G 31 and G 32 It is an organic cation of the pyridine ring.

[0337] Specific examples of the organic cation represented by Formula 2-3 are shown below, but the organic cation represented by Formula 2-3 is not limited to the following specific examples.

[0338] [Chemical formula 43]

[0339]

[0340] <Formula 2-4>

[0341] [Chemical formula 44]

[0342]

[0343] In formula 2-4, A 41 Each independently represents a nitrogen atom or a phosphorus atom. 41 R each independently represents a single bond or a divalent linking group. 4a , R 4b and R 4c Each independently represents an aliphatic group or an aromatic group. 41 and E 42 R each independently represents a single bond or an aliphatic group. 4a , R 4b and R 4c One of them can be combined with E 41 or E 42 m4 is an integer greater than or equal to 2.

[0344] The organic cation having the structure represented by Formula 2-4 has a flexible molecular structure and the cationic sites are regularly arranged, so it is considered that the cyanine pigment is regularly arranged at appropriate positions to form an association. As a result, the infrared absorption ability tends to be maintained for a long time.

[0345] A 41 A and B each independently represent a nitrogen atom or a phosphorus atom. 41 Preferred is a nitrogen atom.

[0346] B 41 Each independently represents a single bond or a divalent linking group. 41 Examples of the divalent linking group include an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 30 carbon atoms, a heterocyclic linking group, -CH=CH-, -O-, -S-, -C(=O)-, -COO-, -NR-, -CONR-, -OCO-, -SO-, -SO 2 - and a linking group formed by linking two or more of these. R represents a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group.

[0347] Among them, B 41 The divalent linking group represented by is preferably an alkylene group. The number of carbon atoms in the alkylene group is preferably 1 to 6, more preferably 1 to 4. The alkylene group is preferably a linear alkylene group.

[0348] R 4a , R 4b and R 4c Each independently represents an aliphatic group or an aromatic group.

[0349] Examples of the aliphatic group include an alkyl group, an alkenyl group, an alkynyl group, and an aralkyl group, and examples of the aromatic group include an aryl group.

[0350] Among them, R4a , R 4b and R 4c The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms.

[0351] E 41 and E 42 Each independently represents a single bond or an aliphatic group.

[0352] And, E 11 and E 12 Each of them is independently preferably a single bond or an alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 6, more preferably 1 to 4. The aryl group is preferably a phenyl group.

[0353] m4 is an integer greater than or equal to 2. m4 is preferably 50 to 3,000, more preferably 100 to 2,000.

[0354] Among them, the organic cation having a structure represented by Formula 2-4 is more preferably A 41 is a nitrogen atom, R 4a , R 4b and R 4c 1 in 1 with E 41 or E 42 An organic cation that is bonded to form a ring.

[0355] Specific examples of organic cations having a structure represented by Formula 2-4 are shown below, but X 1 The organic cation represented by is not limited to the following specific examples. In addition, Me represents a methyl group, and m4 has the same meaning as m4 in Formula 2-4.

[0356] [Chemical formula 45]

[0357]

[0358] X 1 Preferably, it is an organic cation represented by Formula 2-1 or an organic cation having a structure represented by Formula 2-4. It is believed that the association formed by the cyanine pigment is held in a suitable position for a long time by the organic cation represented by Formula 2-1 or the organic cation having a structure represented by Formula 2-4. 1 When the organic cation is represented by Formula 2-1 or an organic cation having a structure represented by Formula 2-4, the invisibility is excellent and the infrared absorption capability can be maintained for a longer period of time.

[0359] [n]

[0360] n is a non-zero number required for neutralizing the charge. For example, when the anion portion is a monovalent anion and the organic cation is a divalent cation, n is 0.5.

[0361] The pigment compound of the present invention is excellent in invisibility and maintains infrared absorption capability for a longer period of time than before, and therefore is expected to be applicable to various uses. The pigment compound of the present invention can be mixed with other components to form a pigment composition.

[0362] Specific examples of the pigment compound represented by Formula 1 are shown below. However, the pigment compound represented by Formula 1 in the present invention is not limited to the following specific examples.

[0363] [Chemical formula 46]

[0364]

[0365] [Chemical formula 47]

[0366]

[0367] In Formula 1, when Cy is represented by Formula 4, the dye compound represented by Formula 1 can be synthesized, for example, by the following method.

[0368] [Chemical formula 48]

[0369]

[0370] First, after compound 41, compound 42 and 2-propanol are mixed, acetic anhydride and triethylamine are added. If an aqueous solution of potassium acetate and methanol are further added, compound 43 can be obtained. Compound 43 is a potassium salt. After compound 43 is purified, the counter cation X of the target pigment compound is added. 1 The target compound, Compound 44, can be obtained by cation exchange with potassium cation.

[0371] [Pigment composition]

[0372] The pigment composition of the present invention comprises the pigment compound represented by the above formula 1 and a medium.

[0373] The medium is not particularly limited as long as it is a medium capable of dispersing the dye compound represented by Formula 1, and examples thereof include water, organic solvents, resins, and mixtures of two or more thereof.

[0374] The medium is preferably a liquid, more preferably an aqueous liquid.

[0375] When using liquid as medium, the pigment composition of the present invention can be used as ink. And, when using aqueous liquid as medium, the pigment composition of the present invention can be used as water-based ink, preferably can be used as water-based ink for inkjet recording.

[0376] -When the medium is not a liquid-

[0377] When a resin is used as a medium, the dye composition of the present invention can be a resin composition containing a dye compound and a resin. The resin composition can be processed into a resin film or a resin molded body.

[0378] The type of resin is not particularly limited, but thermoplastic resins are preferred from the viewpoint of ease of molding. Examples of thermoplastic resins include polyester, polystyrene, polyamide, polyurethane, polycarbonate, cellulose acetate, polyacrylic acid, polyacetal, polypropylene, polyethylene, polysulfone, polyimide, and polyolefin. Among them, the resin is preferably at least one resin selected from the group consisting of polyester, polyamide, and polyurethane.

[0379] The resin includes polymers and oligomers, and can be appropriately selected from compounds having a weight average molecular weight of 5,000 to 1,000,000.

[0380] The resin composition may contain only one resin or two or more resins. When two or more resins are used, it is preferred to use resins having similar glass transition temperatures or SP values ​​(solubility parameters) from the viewpoint of compatibility and moldability.

[0381] The resin composition may contain various additives in addition to the pigment compound represented by Formula 1 and the resin within a range that does not impair the effects of the present invention.

[0382] The pigment composition according to the present invention may contain at least one colorant.

[0383] By containing a colorant, a desired color can be imparted to the resin composition and a resin molded body produced from the resin composition.

[0384] The colorant may be any of a dye and a pigment. As the dye and the pigment, conventionally known dyes and pigments can be used.

[0385] The content of the colorant is preferably 0.0001% by mass to 20% by mass, more preferably 0.001% by mass to 10% by mass, based on the total amount of the resin composition.

[0386] The resin composition may also contain inorganic fillers as needed for the purpose of improving physical properties such as impact resistance, antibacterial properties, gas barrier properties, conductivity, magnetism, piezoelectricity, vibration damping, sound insulation, sliding properties, electromagnetic wave absorption, flame retardancy, dehydration, deodorization, anti-adhesion, oil absorption, water absorption, and moldability.

[0387] As inorganic filler, for example, carbon fiber, glass fiber, glass flake, zeolite, mica, graphite, metal powder, ferrite, aluminum oxide, barium titanate, potassium titanate, barium sulfate, Teflon (registered trademark) powder, talc, charcoal powder, carbon nanotube (CNT), carbon micro coil (CMC), antimony oxide, aluminum hydroxide, magnesium hydroxide, hydrotalcite, calcium oxide, silicon dioxide and calcium carbonate can be cited. The content of inorganic filler contained preferably does not reduce the transparency of the resin molding described later.

[0388] In addition, the resin composition may contain known additives such as leveling agents, pigment dispersants, ultraviolet absorbers, antioxidants, viscosity improvers, light stabilizers, heat stabilizers, metal deactivators, peroxide decomposers, processing stabilizers, nucleating agents, crystallization accelerators, crystallization retarders, anti-gelling agents, fillers, reinforcing agents, plasticizers, lubricants, flame retardants, rust inhibitors, fluorescent brighteners, flow improvers, antistatic agents, etc.

[0389] The preparation method of the resin composition is not particularly limited. For example, in order to make it contain the pigment compound represented by Formula 1, the master batch or resin pellets that become the resin raw material can be directly kneaded and mixed with the pigment compound represented by Formula 1 to be melt-molded. In addition, the pigment compound represented by Formula 1 can also be attached to the resin by methods such as coating and impregnation.

[0390] Among them, if the pigment compound represented by Formula 1 is directly kneaded and mixed with the resin to be melt-molded, the pigment compound represented by Formula 1 is less likely to be detached from the resin surface, and the infrared absorption capability can be maintained for a longer period of time.

[0391] And, when making resin molding, preferably will be mixed with the pigment compound represented by formula 1 and resin and make molding after it is evenly dispersed.In addition, as the method for mixing the pigment compound represented by formula 1 and resin, can enumerate the method for heating kneading resin and the pigment compound represented by formula 1 and the method for stirring mixing resin, the pigment compound represented by formula 1 and solvent.

[0392] The shape and use of the resin molded body are not particularly limited. Examples of the form of the resin molded body include resin films; synthetic fibers; resin containers such as bottles, cosmetic containers, and food containers; resin plates; lenses; toners; exterior parts such as various home appliances and electronic devices represented by general decorations; housing building material parts such as interior materials and exterior materials; and interior and exterior parts of aircraft, vehicles, etc.

[0393] The method for producing the resin molded body is not particularly limited, and a known resin molding method can be appropriately applied.

[0394] -When the medium is liquid-

[0395] The pigment composition of the present invention preferably contains a liquid as a medium. Hereinafter, the liquid as a medium is referred to as a liquid medium.

[0396] The kind of liquid medium is not particularly limited, and can be appropriately selected according to the purpose of use of the pigment composition. Wherein, when the pigment composition of the present invention is applied to ink (e.g., ink for inkjet recording), the liquid medium preferably comprises water, more preferably comprises water and an organic solvent.

[0397] And, if consider that pigment composition is applicable to ink for inkjet recording, then consider from the viewpoint of ejection stability, liquid medium preferably comprises water and boiling point and is the organic solvent more than 100 ℃.Boiling point represents the boiling point under 1 atmospheric pressure (101325Pa).Boiling point is measured by boiling point meter, for example, uses Titan Technologies, KK boiling point meter (product name " DosaTherm300 ") measures.

[0398] From the viewpoint of containing less impurities, water is preferably distilled water, ion-exchanged water, ion-exchanged distilled water or pure water.

[0399] Examples of the organic solvent having a boiling point of 100° C. or higher include ethylene glycol (boiling point: 198° C.), propylene glycol (boiling point: 188° C.), 1,2-butanediol (boiling point: 194° C.), 2,3-butanediol (boiling point: 183° C.), 2-methyl-1,3-propanediol (boiling point: 124° C.), 2-methyl-2,4-pentanediol (boiling point: 198° C.), 1,2,6-hexanetriol (boiling point: 178° C.), 1,2,3-butanetriol (boiling point: 175° C.), 1,2,4-butanetriol (boiling point: 170° C.), diethylene glycol (boiling point: 244° C.), dipropylene glycol (boiling point: 231° C.), 1,3-propanediol (boiling point: 214° C.), 1,3-butanediol (boiling point: 208° C.), 1,4- Polyols such as butanediol (boiling point: 230°C), 1,2-pentanediol (boiling point: 206°C), 2,4-pentanediol (boiling point: 201°C), 2-methyl-1,3-butanediol (boiling point: 203°C), 3-methyl-1,3-butanediol (boiling point: 203°C), 1,5-pentanediol (boiling point: 242°C), 2,2-dimethyl-1,3-propanediol (boiling point: 208°C), 1,2-hexanediol (boiling point: 223°C), 1,6-hexanediol (boiling point: 250°C), 2,5-hexanediol (boiling point: 217°C), 2-ethyl-1,3-hexanediol (boiling point: 243°C), triethylene glycol (boiling point: 287°C), tripropylene glycol (boiling point: 273°C), and glycerol (boiling point: 290°C);

[0400] Ethylene glycol monomethyl ether (boiling point: 124°C), ethylene glycol monoethyl ether (boiling point: 135°C), ethylene glycol-n-propyl ether (boiling point: 150°C), ethylene glycol monobutyl ether (boiling point: 171°C), propylene glycol monomethyl ether (boiling point: 120°C), propylene glycol monoethyl ether (boiling point: 133°C), propylene glycol-n-butyl ether (boiling point: 171°C), propylene glycol-tert-butyl ether (boiling point: 153°C), tetraethylene glycol monomethyl ether (boiling point: 159°C), diethylene glycol methyl ether (boiling point: 194°C), diethylene glycol diethyl ether (boiling point: 162°C), diethylene glycol-n-butyl Ether (boiling point: 230°C), dipropylene glycol monomethyl ether (boiling point: 188°C), diethylene glycol monoethyl ether (boiling point: 202°C), diethylene glycol monobutyl ether (boiling point: 230°C), triethylene glycol methyl ether (boiling point: 249°C), dipropylene glycol-n-propyl ether (boiling point: 213°C), tripropylene glycol methyl ether (boiling point: 243°C), triethylene glycol ethyl ether (boiling point: 256°C), diethylene glycol-n-hexyl ether (boiling point: 259°C), tripropylene glycol-n-propyl ether (boiling point: 261°C), 3-methoxybutanol (boiling point: 161°C) and other polyol alkyl ethers;

[0401] Ethylene glycol phenyl ether (boiling point: 237°C), propylene glycol phenyl ether (boiling point: 243°C), ethylene glycol monobenzyl ether (boiling point: 256°C) and other polyol aromatic ethers;

[0402] Nitrogen-containing compounds such as ε-caprolactam (boiling point: 137°C), N-methylformamide (boiling point: 199°C), N,N-dimethylformamide (boiling point: 153°C), N-methyl-2-pyrrolidone (boiling point: 204°C), 2-pyrrolidone (boiling point: 245°C), 1,3-dimethylimidazolidinone (boiling point: 220°C), and N-methylpyrrolidone (boiling point: 202°C);

[0403] Ester compounds such as propylene glycol monomethyl ether acetate (boiling point: 146°C) and 3-methoxybutyl acetate (boiling point: 172°C);

[0404] Ketone compounds such as diacetone alcohol (boiling point: 169°C) and γ-butyrolactone (boiling point: 204°C).

[0405] In the present invention, the content of water in the pigment composition is preferably 30% by mass or more, more preferably 40% by mass or more, and even more preferably 50% by mass or more, relative to the total mass of the pigment composition.

[0406] In the present invention, the content of the organic solvent having a boiling point of 100° C. or higher in the dye composition is preferably 1 to 50% by mass, more preferably 2 to 40% by mass, based on the total mass of the dye composition.

[0407] The pigment composition of the present invention may contain a surfactant.

[0408] The surfactant may be any of anionic surfactants, cationic surfactants, amphoteric surfactants, nonionic surfactants, and betaine-based surfactants.

[0409] Among them, when the dye composition is applied to ink, from the viewpoint of suppressing the ejection disturbance of the ink, the surfactant is preferably a nonionic surfactant, and more preferably an acetylene glycol-based surfactant.

[0410] Examples of the acetylene glycol-based surfactant include 2,4,7,9-tetramethyl-5-decyne-4,7-diol and an alkylene oxide adduct of 2,4,7,9-tetramethyl-5-decyne-4,7-diol.

[0411] Examples of commercially available products of the acetylene glycol-based surfactant include Surfynol series such as Surfynol 104PG manufactured by Nissin Chemical Industry Co., Ltd. and E series such as OLFINE E1010 manufactured by Nissin Chemical Industry Co., Ltd.

[0412] As surfactants other than acetylene glycol surfactants, fluorine-based surfactants are preferred. As fluorine-based surfactants, for example, Capstone (registered trademark) FS-63, Capstone FS-61 (manufactured by Dupont), Ftergent (registered trademark, hereinafter the same) 100, Ftergent 110, Ftergent 150 (manufactured by Neos Corporation), CHEMGUARD (registered trademark) S-760P (manufactured by Chemguard Inc.) can be cited.

[0413] The content of the surfactant is preferably 0.1% by mass or more, more preferably 0.1% by mass to 10% by mass, and further preferably 0.2% by mass to 3% by mass, relative to the total mass of the dye composition.

[0414] The dye composition of the present invention may contain a polymerizable compound as a liquid medium. When the dye composition contains a polymerizable compound, the dye composition can be cured by irradiation with active energy rays.

[0415] When the pigment composition is applied to ink, the pigment composition of the present invention may further contain known additives used for ink.

[0416] Examples of additives include surfactants, resins, anti-desiccant (in other words, wetting agents), anti-fading agents, emulsion stabilizers, penetration enhancers, preservatives, antifungal agents, pH adjusters, surface tension adjusters, defoamers, viscosity adjusters, dispersants, rust inhibitors, and chelating agents.

[0417] When the pigment composition is applied to ink, it may contain other pigments in addition to the pigment compound represented by Formula 1. The other pigments are not particularly limited, and pigments known in the field of inks can be used.

[0418] From the viewpoint of invisibility, the content of other coloring matter is preferably 0.1% by mass or less, and more preferably 0.05% by mass or less, relative to the total mass of the ink.

[0419] Furthermore, the dye composition of the present invention can be set to a dye composition that contains a dye having absorption in the visible light region and can form a visible image having absorption in the near infrared region, depending on the purpose.

[0420] The pigment composition of the present invention can be suitably used in ink. The ink is preferably used for inkjet recording.

[0421] From the viewpoint of ejection stability, the pH of the ink is preferably 7 to 10, more preferably 7.5 to 9.5. The pH of the ink is measured at 25° C. using a pH meter, for example, a pH meter manufactured by DKK-TOA Corporation (model “HM-31”).

[0422] The viscosity of the ink is preferably 0.5 mPa·s to 30 mPa·s, more preferably 2 mPa·s to 20 mPa·s, further preferably 2 mPa·s to 15 mPa·s, and further preferably 3 mPa·s to 10 mPa·s. The viscosity of the ink is measured at 25° C. using a viscometer, for example, a TV-22 viscometer manufactured by Toki Sangyo Co., Ltd.

[0423] The surface tension of the ink is preferably 60 mN / m or less, more preferably 20 mN / m to 50 mN / m, and further preferably 25 mN / m to 45 mN / m. The surface tension of the ink is measured at 25° C. using a surface tensiometer, for example, using an automatic surface tensiometer manufactured by Kyowa Interface Science Co., LTD. (product name “CBVP-Z”), and measured by a plate method.

[0424] And, as the purposes of pigment composition of the present invention, can enumerate the image recording material that is used for recording image (especially invisible image).As image recording material, specifically, take inkjet recording material as representative, can enumerate heat-sensitive recording material, pressure-sensitive recording material, utilize recording material of electronic photography mode, transfer type silver halide photosensitive material, printing ink and recording pen.Pigment composition of the present invention is preferably used for inkjet recording material, heat-sensitive recording material or utilize recording material of electronic photography mode.

[0425] Furthermore, the pigment composition of the present invention can also be applied to solid imaging elements such as charge coupled devices (CCDs) and complementary metal oxide semiconductors (CMOS); infrared sensors; various devices such as image display devices; infrared cut filters used in displays such as plasma displays (PDPs), or dyeing solutions for dyeing various fibers. Furthermore, the pigment composition of the present invention can also be applied to photothermal conversion materials such as write-once optical disks or memory fusion materials. Furthermore, since the pigment composition of the present invention has absorption in the near-infrared region with excellent human body transmittance, it can also be applied to diagnostic markers and photodynamic therapy agents in addition to the above-mentioned uses.

[0426] Furthermore, the pigment composition of the present invention can also be applied to fibers (heat preservation and heat storage properties); camouflage properties for infrared detection (camouflage performance); preventing eye fatigue; or as a positioning marker for photographs, films, etc. Furthermore, by using the pigment composition of the present invention as a cured film, the application can be expanded.

[0427] Furthermore, the pigment composition of the present invention can be applied to lenses having a function of absorbing or cutting off near infrared rays (e.g., camera lenses for digital cameras, mobile phones, car cameras, etc.; optical lenses such as f-θ lenses and pickup lenses); optical filters for semiconductor light-receiving elements; agricultural coating agents for the purpose of selectively utilizing sunlight; recording media that utilize heat absorption of near infrared rays; near infrared filters for electronic devices or photography; goggles; sunshades; heat-ray blocking filters; optical character reading and recording; confidential document anti-copying purposes; electronic photographic photoreceptors; or laser welding. Furthermore, the pigment composition of the present invention can also be used as a noise reduction filter for CCD cameras and a filter for CMOS image sensors.

[0428] [Inkjet recording method]

[0429] The inkjet recording method of the present invention includes the step of applying the above-mentioned ink to a substrate.

[0430] The substrate is not particularly limited as long as an image can be formed, and examples thereof include paper, cloth, wood, metal plates, and resin films. The substrate may be subjected to a surface treatment in advance.

[0431] Examples of the paper include pure white roll paper, kraft paper, cardboard, premium paper, OCR paper, coated paper, mirror-coated paper, capacitor paper, and paraffin paper.

[0432] Examples of the resin film include polyester film, polypropylene (PP) film, cellophane, acetate film, polycarbonate (PC) film, acrylic resin film, polyethylene terephthalate (PET) film, biaxially stretched polystyrene (OPS) film, biaxially stretched polypropylene (OPP) film, biaxially stretched nylon (ONy) film, polyvinyl chloride (PVC) film, polyethylene (PE) film and triacetate (TAC) film.

[0433] There is no particular limitation on the inkjet recording method as long as it is a method that can record images. It can be a well-known method, such as a charge control method that utilizes electrostatic induction force to eject ink, a drop-on-demand inkjet method (pressure pulse method) that utilizes the vibration pressure of a piezoelectric element, an acoustic inkjet method that converts an electrical signal into a sound beam to irradiate the ink and utilizes radiation pressure to eject the ink, and a thermal inkjet (Bubble Jet (registered trademark)) method that heats the ink to form bubbles and utilizes the generated pressure.

[0434] As an inkjet recording method, the following inkjet recording method can be particularly effectively used: using the method described in Japanese Patent Application Laid-Open No. 54-59936, the ink subjected to thermal energy undergoes a rapid volume change, and the ink is ejected from the nozzle by the force generated by the state change.

[0435] In addition, regarding the inkjet recording method, the method described in paragraphs 0093 to 0105 of Japanese Patent Application Laid-Open No. 2003-306623 can also be referred to.

[0436] As inkjet heads used for inkjet recording, there are a reciprocating method that uses a short column head to record while scanning the head in the width direction of the substrate, and a row method that uses a row head with recording elements arranged in the entire area corresponding to one side of the substrate.

[0437] In the line method, patterning can be performed on the entire surface of the substrate by scanning the substrate in a direction intersecting the arrangement direction of the recording elements, and a transport system such as a carriage for scanning short heads is unnecessary.

[0438] Furthermore, since there is no need to perform complicated scanning control on the movement of the carriage and the substrate, only the substrate moves, and thus the recording speed can be increased compared to the reciprocating method.

[0439] From the viewpoint of obtaining a high-definition image, the ejection amount of the ink ejected from the inkjet head is preferably 1 pL (picoliter) to 20 pL, and more preferably 1.5 pL to 10 pL.

[0440] The inkjet recording method of the present invention may include other steps in addition to the step of recording an image on a substrate by inkjet recording. As other steps, for example, a step of drying the image after recording the image can be cited. In addition, when the ink contains a polymerizable compound, the image recording method of the present invention may include a step of irradiating active energy rays.

[0441] [Visual Records]

[0442] The image recorded material of the present invention comprises a substrate and an infrared absorption image which is a cured product of the ink disposed on the substrate.

[0443] The solidified product includes a dried product of ink and a solidified product obtained by polymerizing a polymerizable compound in the ink.

[0444] Furthermore, the image recorded material of the present invention comprises a substrate and an infrared absorption image disposed on the substrate, the infrared absorption image comprises the pigment compound represented by the above formula 1, and the maximum absorption wavelength of the infrared absorption image is within the range of 700 nm to 1300 nm.

[0445] The substrate is as described above, and its description is omitted. The pattern of the infrared absorption image arranged on the substrate is not particularly limited, and can be appropriately selected according to the application.

[0446] The maximum absorption wavelength of the infrared absorption image can be confirmed by measuring the optical density (OD) of the infrared absorption image using a spectrophotometer UV-3100PC equipped with a 150 mm large integrating sphere attachment LISR-3100 manufactured by Shimadzu Corporation. From the viewpoint of invisibility and readability of the infrared absorption image, the maximum absorption wavelength of the infrared absorption image is preferably within the range of 700 nm to 1300 nm.

[0447] The image recorded article of the present invention can be applied to an anti-counterfeiting system for anti-counterfeiting purposes. The image recorded article of the present invention has excellent invisibility and can maintain infrared absorption for a longer period of time than before, so it can maintain anti-counterfeiting properties for a long period of time.

[0448] Example

[0449] Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples unless it exceeds the gist of the present invention.

[0450] First, Compounds 1 to 60 and Comparative Compounds 1 to 3 described in Tables 1 to 3 were prepared. The following is a method for synthesizing Compounds 9, 12, 23, 46, and 50. Compounds other than Compounds 9, 12, 23, 46, and 50 were synthesized in the same manner as Compounds 9, 12, 23, 46, and 50 by changing the starting materials.

[0451] [Chemical formula 49]

[0452]

[0453] Compounds 1 to 60 are all pigment compounds represented by Formula 1, and the basic core 1 and the basic core 2 have the same structure. 1 , basic nucleus 1 and basic nucleus 2 (in the table, described as "two basic nuclei in Cy"), and X 1 .

[0454] <Synthesis of Compound 9>

[0455] [Chemical formula 50]

[0456]

[0457] In a flask, 21.0 g of compound 9-A, 11.4 g of compound 9-B, and 114.8 g of 2-propanol were added. Then, 20.3 g of acetic anhydride and 13.4 g of triethylamine were added at 10°C, and stirred at room temperature for 2 hours. A mixed solution of 6.5 g of potassium acetate and 16.2 g of water and 28.2 g of methanol were added to the obtained reaction solution. Stirred at 50°C for 30 minutes and stirred at room temperature for 1 hour. By filtering the crystals precipitated in the reaction solution, 15.0 g of a crude product of compound 9-C was obtained.

[0458] In a flask, 15.0 g of the crude product of the obtained compound 9-C and 465.7 g of methanol were added, and stirred at 65° C. for 30 minutes. After returning to room temperature, a mixed solution of 6.5 g of potassium acetate and 16.2 g of water and 28.2 g of methanol were added, and stirred for 1 hour. The crystals precipitated in the dispersion were filtered to obtain 10.5 g of compound 9-C.

[0459] In a flask, 4.0 g of the obtained compound 9-C and 266.7 g of water were added, and the mixture was stirred at room temperature for 12 hours. 1.1 g of compound 9-D was added to the obtained aqueous solution, and the mixture was stirred at room temperature for 12 hours. Thereafter, 156.2 g of methanol was added, and the mixture was stirred at room temperature for 30 minutes. By filtering the crystals precipitated in the reaction solution, 4.0 g of compound 9 was obtained.

[0460] NMR spectrum of compound 9: 1 H-NMR (heavy THF / heavy water / 30% NaOD) δ8.2-8.0 (2H, m), 8.0-7.6 (6H, m), 7.2-6.8 (4H, m), 5.8 (1H, d), 5.3 (1H, d), 4.0 (2H, s), 3.8-3.7 (2H, m), 3.3 (9H, s), 3.3-3.0 (2H, m), 2.7-2.5 (4H, m), 1.8 (6H, s), 1.5 (3H, s), 1.3-1.1 (9H, m)

[0461] pass 1 The structure of the obtained compound 9 was confirmed by H-NMR spectroscopy.

[0462] <Synthesis of Compound 12>

[0463]

[0464] In a flask, 21.0 g of compound 12-A, 12.8 g of compound 12-B, and 114.8 g of 2-propanol were added. Then, 20.3 g of acetic anhydride and 13.4 g of triethylamine were added at 10°C, and stirred at room temperature for 2 hours. A mixed solution of 6.5 g of potassium acetate and 16.2 g of water and 28.2 g of methanol were added to the obtained reaction solution. Stirred at 50°C for 30 minutes and stirred at room temperature for 1 hour. By filtering the crystals precipitated in the reaction solution, 14.8 g of a crude product of compound 12-C was obtained.

[0465] In a flask, 14.8 g of the obtained crude product of compound 12-C and 465.7 g of methanol were added, and stirred at 65°C for 30 minutes. After returning to room temperature, a mixed solution of 6.5 g of potassium acetate and 16.2 g of water and 28.2 g of methanol were added, and stirred for 1 hour. The crystals precipitated in the dispersion were filtered to obtain 10.2 g of compound 12-C.

[0466] In a flask, 4.0 g of the obtained compound 12-C and 266.7 g of water were added, and the mixture was stirred at room temperature for 12 hours. 1.1 g of compound 12-D was added to the obtained aqueous solution, and the mixture was stirred at room temperature for 12 hours. Thereafter, 156.2 g of methanol was added, and the mixture was stirred at room temperature for 30 minutes. By filtering the crystals precipitated from the reaction solution, 3.9 g of compound 12 was obtained.

[0467] NMR spectrum of compound 12: 1H-NMR (heavy THF / heavy water / 30% NaOD) δ8.2-8.0 (2H, m), 8.0-7.6 (6H, m), 7.4-7.3 (3H, m), 7.2-6.8 (6H, m), 5.8 (1H, d), 5.3 (1H, d), 4.0 (2H, s), 3.8-3.7 (2H, m), 3.3 (9H, s), 3.3-3.0 (2H, m), 2.7-2.5 (4H, m), 1.8 (6H, s), 1.5 (3H, s), 1.3-1.1 (9H, m)

[0468] pass 1 The structure of the obtained compound 12 was confirmed by H-NMR spectroscopy.

[0469] <Synthesis of Compound 23>

[0470] [Chemical formula 51]

[0471]

[0472] In a flask, 21.0 g of compound 23-A, 11.8 g of compound 23-B, and 114.8 g of 2-propanol were added. Then, 20.9 g of acetic anhydride and 13.8 g of triethylamine were added at 10°C, and stirred at room temperature for 2 hours. A mixed solution of 6.7 g of potassium acetate and 16.2 g of water and 28.2 g of methanol were added to the obtained reaction solution. Stirred at 50°C for 30 minutes and stirred at room temperature for 1 hour. By filtering the crystals precipitated in the reaction solution, 14.0 g of a crude product of compound 23-C was obtained.

[0473] In a flask, 14.0 g of the obtained crude product of compound 23-C and 465.7 g of methanol were added, and stirred at 65° C. for 30 minutes. After returning to room temperature, a mixed solution of 6.7 g of potassium acetate and 16.2 g of water and 28.2 g of methanol were added, and stirred for 1 hour. The crystals precipitated in the dispersion were filtered to obtain 10.2 g of compound 23-C.

[0474] In a flask, 4.0 g of the obtained compound 23-C and 266.7 g of water were added, and the mixture was stirred at room temperature for 12 hours. 1.1 g of compound 23-D was added to the obtained aqueous solution, and the mixture was stirred at room temperature for 12 hours. Thereafter, 156.2 g of methanol was added, and the mixture was stirred at room temperature for 30 minutes. By filtering the crystals precipitated from the reaction solution, 4.0 g of compound 23 was obtained.

[0475] NMR spectrum of compound 23: 1H-NMR (heavy THF / heavy water / 30% NaOD) δ8.0-7.6 (8H, m), 7.2-6.8 (4H, m), 6.5 (1H, d), 5.5 (1H, d), 4.0 (2H, s), 3.8-3.7 (2H, m), 3.3 (9H, s), 3.3-3.0 (2H, m), 2.7-2.5 (4H, m), 1.2 (6H, t)

[0476] pass 1 The structure of the obtained compound 23 was confirmed by H-NMR spectroscopy.

[0477] <Synthesis of Compound 46>

[0478] [Chemical formula 52]

[0479]

[0480] In a flask, 4.0 g of compound 9-C and 266.7 g of water were added, and the mixture was stirred at room temperature for 12 hours. 0.96 g of compound 46-D was added to the obtained aqueous solution, and the mixture was stirred at room temperature for 12 hours. Thereafter, 156.2 g of methanol was added, and the mixture was stirred at room temperature for 30 minutes. By filtering the crystals precipitated from the reaction solution, 4.1 g of compound 46 was obtained.

[0481] NMR spectrum of compound 46: 1 H-NMR (heavy THF / heavy water / 30% NaOD) δ8.7-8.6 (2H, m), 8.2-8.0 (2H, m), 8.0-7.6 (7H, m), 7.5-7.4 (2H, m), 7.2-6.8 (4H, m), 5.8 (1H, d), 5.3 (1H, d), 4.0 (2H, s), 3.8-3.7 (2H, m), 3.3-3.0 (2H, m), 2.7-2.5 (4H, m), 1.8 (6H, s), 1.5 (3H, s), 1.3-1.1 (9H, m)

[0482] pass 1 The structure of the obtained compound 46 was confirmed by H-NMR spectroscopy.

[0483] <Synthesis of Compound 50>

[0484] [Chemical formula 53]

[0485]

[0486] In a flask, 4.0 g of compound 9-C and 266.7 g of water were added, and the mixture was stirred at room temperature for 12 hours. 1.1 g of compound 50-D was added to the obtained aqueous solution, and the mixture was stirred at room temperature for 12 hours. Then, 156.2 g of methanol was added, and the mixture was stirred at room temperature for 30 minutes. By filtering the crystals precipitated in the reaction solution, 3.9 g of compound 50 was obtained.

[0487] NMR spectrum of compound 50: 1 H-NMR (heavy THF / heavy water / 30% NaOD) δ8.2-8.0 (2H, m), 8.0-7.6 (6H, m), 7.2-6.8 (4H, m), 5.8 (1H, d), 5.3 (1H, d), 4.0 (2.7H, s), 3.8-3.7 (2H, m), 3.3 (8H, s), 3.3-3.0 (2H, m), 2.7-2.5 (4H, m), 1.8 (6H, s), 1.5 (3H, s), 1.3-1.1 (9H, m)

[0488] pass 1 The structure of the obtained compound 50 was confirmed by H-NMR spectroscopy.

[0489] [Table 1]

[0490]

[0491] [Table 2]

[0492]

[0493] [Table 3]

[0494]

[0495] <Comparative Compound 1 to Comparative Compound 3>

[0496] ·Comparative compound 1……Compound No. 2 described in Japanese Patent Application Laid-Open No. 2017-226820

[0497] Comparative compound 2: Compound (I-13) described in Japanese Patent Application Laid-Open No. 2002-90521

[0498] Comparative compound 3: Combination of compound A-1 and compound B-19 described in Japanese Patent Application Laid-Open No. 2000-292758

[0499] The structures of Comparative Compounds 1 to 3 are as follows.

[0500] (Comparative Compound 1)

[0501] [Chemical formula 54]

[0502]

[0503] (Comparative Compound 2)

[0504] [Chemical formula 55]

[0505]

[0506] (Comparative Compound 3)

[0507] [Chemical formula 56]

[0508]

[0509] Next, an ink was prepared using a pigment compound (any one of Compound 1 to Compound 60, Comparative Compound 1 to Comparative Compound 3). The components were mixed to form the following composition. 100 parts by mass of zirconia beads having a diameter of 0.1 mm were further added, and a dispersion treatment was performed at 400 rpm (revolutions / minute) for 5 hours using a planetary ball mill to obtain an ink.

[0510] Pigment compound... 0.5 parts by mass

[0511] Ultrapure water (resistance value 18 MΩ·cm or more)……78.8 parts by mass

[0512] Organic solvent: propylene glycol... 19.7 parts by mass

[0513] Acetylene glycol surfactant: OLFINE E1010 (manufactured by Nissin Chemical Industry Co., Ltd.) ... 1 part by mass

[0514] <Production of image records>

[0515] The prepared ink was loaded into an ink tank of an inkjet recording apparatus (product name "DMP-2831", manufactured by FUJIFILM DIMATIX Inc.). OKTopKote paper (manufactured by Oji Paper Co., Ltd.) was prepared as a substrate. After the ink was ejected onto the substrate, it was dried with warm air at 100° C. for 1 minute to record a solid image.

[0516] The obtained image records were used to evaluate invisibility, light resistance, and moist heat resistance. The evaluation method was as follows.

[0517] [Invisibility]

[0518] Use The spectrophotometer UV-3100PC (manufactured by Shimadzu Corporation) of the large integrating sphere attachment LISR-3100 (manufactured by Shimadzu Corporation) measured the optical density (OD) at 450nm and the optical density at the maximum absorption wavelength. Based on the ratio P of the OD at 450nm to the OD at the maximum absorption wavelength (OD at 450nm / OD at the maximum absorption wavelength), the invisibility was evaluated. The evaluation criteria are as follows. It can be said that the smaller the ratio P, the better the invisibility. The evaluation criteria are as follows. A, B, and C are levels that have no problems in practical application.

[0519] A: The ratio P is 1 / 10 or less.

[0520] B: The ratio P is more than 1 / 10 and less than 1 / 7.

[0521] C: The ratio P is more than 1 / 7 and less than 1 / 5.

[0522] D: The proportion P exceeds 1 / 5.

[0523] [Lightfastness]

[0524] Using the prepared ink, three types of image records were produced, each having an optical density (OD) of 0.5, 1.0, and 1.5 at the maximum absorption wavelength. The OD was adjusted by adjusting the ejection amount of the ink.

[0525] Using a weathering tester (Atlus C.I65), each image record produced was irradiated with xenon light of 85,000 lux for 1 day. The optical density (OD) at the maximum absorption wavelength of the image record after light irradiation was measured. The pigment residual rate was calculated according to the following formula. It can be said that the higher the pigment residual rate, the better the light resistance.

[0526] Pigment residual rate (%) = (OD after light irradiation) ÷ (OD before light irradiation) × 100

[0527] All optical densities were measured using a spectrophotometer UV-3100PC equipped with a 150 mm large integrating sphere attachment LISR-3100 manufactured by SHIMADZU CORPORATION.

[0528] The evaluation criteria are as follows: A, B, and C are levels that do not cause problems in practical use.

[0529] A: In all three types of image records, the pigment remaining rate was 90% or more.

[0530] B: In all three types of image records, the pigment remaining ratio was 75% or more and less than 90%.

[0531] C: In at least one of the three types of image recorded materials, the pigment remaining rate was less than 75%, and in all of the three types of image recorded materials, the pigment remaining rate was 60% or more.

[0532] D: In one or two of the three types of image records, the pigment remaining rate was less than 60%.

[0533] E: In all three types of image records, the pigment remaining rate was less than 60%.

[0534] [Moisture and heat resistance]

[0535] Using the prepared ink, three types of image records were produced, each having an optical density (OD) of 0.5, 1.0, and 1.5 at the maximum absorption wavelength. The OD was adjusted by adjusting the ejection amount of the ink.

[0536] Each image recording material produced was stored in a box set at a temperature of 45°C and a humidity of 85% for 7 days. The optical density (OD) at the maximum absorption wavelength of the image recording material after storage was measured. The pigment residual rate was calculated according to the following formula. It can be said that the higher the pigment residual rate, the better the light resistance.

[0537] Pigment residual rate (%) = (OD after storage) ÷ (OD before storage) × 100

[0538] All optical densities were measured using a spectrophotometer UV-3100PC equipped with a 150 mm large integrating sphere attachment LISR-3100 manufactured by SHIMADZU CORPORATION.

[0539] The evaluation criteria are as follows: A, B, and C are levels that do not cause problems in practical use.

[0540] A: In all three types of image records, the pigment remaining rate was 90% or more.

[0541] B: In all three types of image records, the pigment remaining ratio was 75% or more and less than 90%.

[0542] C: In at least one of the three types of image recorded materials, the pigment remaining rate was less than 75%, and in all of the three types of image recorded materials, the pigment remaining rate was 60% or more.

[0543] D: In one or two of the three types of image records, the pigment remaining rate was less than 60%.

[0544] E: In all three types of image records, the pigment remaining rate was less than 60%.

[0545] The evaluation results are shown in Tables 4 and 5.

[0546] [Table 4]

[0547]

[0548] [Table 5]

[0549]

[0550] As shown in Tables 4 and 5, in Examples 1 to 60, since the dye compound represented by Formula 1 was included, image records having excellent invisibility and maintaining infrared absorption capability for a longer period than before were obtained.

[0551] On the other hand, it is found that in Comparative Example 1, since the dye compound is a phthalocyanine dye, the invisibility is poor.

[0552] It is understood that in Comparative Example 2, since the dye compound does not have an organic cation, the light resistance and moist heat resistance are inferior.

[0553] It is found that in Comparative Example 3, since the dye compound has an organic cation including a bipyridine skeleton, the light resistance and moist heat resistance are poor.

[0554] <Example 100>

[0555] 0.02 g of compound 9 and 10 g of polyethylene terephthalate resin (Tg: 60° C.) were placed in a hopper of a twin kneader and kneaded for 5 minutes at a temperature of 120° C. and a screw speed of 200 rpm (revolutions per minute) to prepare a resin kneaded product.

[0556] It can be seen that the maximum absorption wavelength of the absorption spectrum of the obtained resin kneaded product is 900 nm or more and the value of the absorbance at 450 nm / the absorbance at the maximum absorption wavelength is 1 / 10 or less, and the invisibility is excellent. In addition, the obtained resin kneaded product was subjected to the above-mentioned light resistance evaluation. As a result, it can be seen that in all three types of image records, the pigment residual rate is 90% or more, and the light resistance is excellent.

[0557] In addition, regarding the invention of Japanese Patent Application No. 2020-147010 filed on September 1, 2020, the entirety of the invention is incorporated into this specification by reference. Furthermore, all documents, patent applications, and technical standards described in this specification are incorporated into this specification by reference to the same extent as if each document, patent application, and technical standard was specifically and separately described as being incorporated by reference.

Claims

1. A pigment composition comprising a pigment compound having a cyanine pigment structure represented by the following formula 1 and a medium, wherein the medium is an aqueous liquid, In formula 1, L 1 represents a methine chain consisting of 5, 7 or 9 methine groups, R 1 and R 2 Each independently represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or an aryl group, wherein The alkyl group has 1 to 20 carbon atoms, the alkenyl group has 2 to 20 carbon atoms, the alkynyl group has 2 to 20 carbon atoms, the arylalkyl group has 1 to 20 carbon atoms, the aryl group has 6 to 25 carbon atoms, and the aryl group has 6 to 25 carbon atoms. 1 and T 2 Each independently represents a non-metal atom group that forms a 5-membered or 6-membered nitrogen-containing heterocyclic ring that may be fused, wherein the nitrogen-containing heterocyclic ring is an oxazole ring, an isoxazole ring, a benzoxazole ring, a naphthoxazole ring, an oxazolocarbazole ring, an oxazolodibenzofuran ring, a thiazole ring, a benzothiazole ring, a naphthothiazole ring, an indolenine ring, a benzoindolenine ring, an imidazole ring, a benzimidazole ring, a naphthoimidazole ring, a quinoline ring, a pyridine ring, a pyrrolopyridine ring, a furanopyrrole ring, an indolizine ring, an imidazoquinoxaline ring or a quinoxaline ring, Cy is an anion moiety, and X 1 represents an organic cation having a flexible molecular structure represented by the following formula 2-1, formula 2-2 or formula 2-3 or an organic cation having a flexible molecular structure represented by formula 2-4, n represents a non-zero number required for neutralizing the charge, In formula 2-1, A 11 and A 12 Each independently represents a nitrogen atom or a phosphorus atom, and B 11 Each independently represents a divalent linking group, wherein the divalent linking group is an alkylene group having 2 to 20 carbon atoms, and R 1a , R 1b , R 1c , R 1d 、E 11 and E 12 Each independently represents an alkyl group or a phenyl group, wherein the alkyl group has 1 to 10 carbon atoms, and R 1a , R 1b , R 1c and R 1d may be bonded to each other to form a ring, m1 is an integer greater than 1, In formula 2-2, A 21 , A 22 and A 23 Each independently represents a nitrogen atom or a phosphorus atom, and B 21 and B 22 Each independently represents a divalent linking group, wherein the divalent linking group is an alkylene group having 2 to 20 carbon atoms, and R 2a and R 2b Each independently represents an alkyl group or a phenyl group, the alkyl group has 1 to 10 carbon atoms, m2 is an integer greater than 0, and G 21 Indicates that the ring contains A 21 A non-metallic atom group of aromatic rings containing A 21 The aromatic ring of G is a pyridine ring, an imidazole ring, an oxazole ring or a thiazole ring. 22 Indicates that the ring contains A 23 A non-metallic atom group of aromatic rings containing A 23 The aromatic ring is a pyridine ring, an imidazole ring, an oxazole ring or a thiazole ring, In formula 2-3, A 31 and A 32 Each independently represents a nitrogen atom or a phosphorus atom, and B 31 represents a divalent linking group, wherein the divalent linking group is an alkylene group having 2 to 20 carbon atoms, and R 3a and R 3b Each independently represents an alkyl group or a phenyl group, wherein the alkyl group has 1 to 10 carbon atoms, and G 31 Indicates that the ring contains A 31 A non-metallic atom group of aromatic rings containing A 31 The aromatic ring of G is a pyridine ring. 32 Indicates that the ring contains A 32 A non-metallic atom group of aromatic rings containing A 32 The aromatic ring of is a pyridine ring, In formula 2-4, A 41 Each independently represents a nitrogen atom or a phosphorus atom, and B 41 Each independently represents a single bond or a divalent linking group, wherein the divalent linking group is an alkylene group having 1 to 6 carbon atoms, and R 4a , R 4b and R 4c Each independently represents an alkyl group or a phenyl group, wherein the alkyl group has 1 to 6 carbon atoms, and E 41 and E 42 Each independently represents a single bond or an alkyl group having 1 to 6 carbon atoms, R 4a , R 4b and R 4c One of them can be combined with E 41 or E 42 They are bonded to form a ring, and m4 is an integer greater than or equal to 2.

2. The pigment composition according to claim 1, wherein In Formula 2-1, Formula 2-2 and Formula 2-3, B 11 , B 21 , B 22 and B 31 Each independently is a divalent linking group having 2 to 8 carbon atoms.

3. The pigment composition according to claim 1 or 2, wherein In Formula 2-1, Formula 2-2, Formula 2-3 and Formula 2-4, A 11 , A 12 , A 21 , A 22 , A 23 , A 31 , A 32 and A 41 A nitrogen atom.

4. The pigment composition according to claim 1 or 2, wherein In Formula 1, X 1 It represents an organic cation having a flexible molecular structure represented by the formula 2-1 or an organic cation having a flexible molecular structure represented by the formula 2-4.

5. The pigment composition according to claim 1 or 2, wherein In the above formula 1, Cy is represented by the following formula 4: In formula 4, Y 1 and Y 2 Represent CR independently 3 R 4 -, -O-, -S-, -Se-, or -NR 5 -, R 3 , R 4 and R 5 Each independently represents a hydrogen atom, an aliphatic group or an aromatic ring group, R 3 and R 4 can bond to each other to form a ring, A 1 and A 2 Each independently represents a non-metallic atom group forming an aromatic ring or an aromatic heterocyclic ring, and L 2 Each independently represents a methine chain consisting of 1, 2 or 3 methine groups, L 2 No substituent, R 6 and R 7 Each independently represents a hydrogen atom or an aliphatic group, R 6 and R 7 can be linked to each other to form a ring, R 8 It is represented by the following formula A, -S A -T A Formula A In formula A, S A represents a single bond, alkylene, alkenylene, alkynylene, -O-, -S-, -NR L1 -, -C(=O)-, -C(=O)O-, -C(=O)NR L1 -、-S(=O)2-、-OR L2 - or a group consisting of at least two of these, R L1 Each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and R L2 represents an alkylene group, an arylene group or a divalent heterocyclic group, T A represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a cyano group, a hydroxyl group, a formyl group, a carboxyl group, an amino group, a thiol group, a sulfone group, a phosphoryl group, a boryl group, a vinyl group, an ethynyl group, a trialkylsilyl group or a trialkoxysilyl group.

6. The pigment composition according to claim 5, wherein In the formula 4, A 1 and A 2 Each independently represents a non-metal atom group forming a benzene ring or a naphthalene ring.

7. The pigment composition according to claim 1 or 2, wherein The medium includes water and an organic solvent having a boiling point of 100° C. or higher.

8. The pigment composition according to claim 1 or 2, which is ink.

9. The pigment composition according to claim 8, which is used for inkjet recording. 10 . An inkjet recording method comprising the step of providing the pigment composition according to claim 9 on a substrate.

11. An image record comprising: substrate; and The cured product of the pigment composition according to claim 8 disposed on the substrate is an infrared absorption image.

12. An image record comprising: substrate; and an infrared absorption image disposed on the substrate, The infrared absorption image includes a pigment compound having a cyanine pigment structure represented by the following formula 1, and the maximum absorption wavelength of the infrared absorption image is within a range of 700 nm to 1300 nm. In formula 1, L 1 represents a methine chain consisting of 5, 7 or 9 methine groups, R 1 and R 2 Each independently represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or an aryl group, wherein The alkyl group has 1 to 20 carbon atoms, the alkenyl group has 2 to 20 carbon atoms, the alkynyl group has 2 to 20 carbon atoms, the arylalkyl group has 1 to 20 carbon atoms, the aryl group has 6 to 25 carbon atoms, and the aryl group has 6 to 25 carbon atoms. 1 and T 2 Each independently represents a non-metal atom group that forms a 5-membered or 6-membered nitrogen-containing heterocyclic ring that may be fused, wherein the nitrogen-containing heterocyclic ring is an oxazole ring, an isoxazole ring, a benzoxazole ring, a naphthoxazole ring, an oxazolocarbazole ring, an oxazolodibenzofuran ring, a thiazole ring, a benzothiazole ring, a naphthothiazole ring, an indolenine ring, a benzoindolenine ring, an imidazole ring, a benzimidazole ring, a naphthoimidazole ring, a quinoline ring, a pyridine ring, a pyrrolopyridine ring, a furanopyrrole ring, an indolizine ring, an imidazoquinoxaline ring or a quinoxaline ring, Cy is an anion moiety, and X 1 represents an organic cation having a flexible molecular structure represented by the following formula 2-1, formula 2-2 or formula 2-3 or an organic cation having a flexible molecular structure represented by formula 2-4, n represents a non-zero number required for neutralizing the charge, In formula 2-1, A 11 and A 12 Each independently represents a nitrogen atom or a phosphorus atom, and B 11 Each independently represents a divalent linking group, wherein the divalent linking group is an alkylene group having 2 to 20 carbon atoms, and R 1a , R 1b , R 1c , R 1d 、E 11 and E 12 Each independently represents an alkyl group or a phenyl group, wherein the alkyl group has 1 to 10 carbon atoms, and R 1a , R 1b , R 1c and R 1d may be bonded to each other to form a ring, m1 is an integer greater than 1, In formula 2-2, A 21 , A 22 and A 23 Each independently represents a nitrogen atom or a phosphorus atom, and B 21 and B 22 Each independently represents a divalent linking group, wherein the divalent linking group is an alkylene group having 2 to 20 carbon atoms, and R 2a and R 2b Each independently represents an alkyl group or a phenyl group, the alkyl group has 1 to 10 carbon atoms, m2 is an integer greater than 0, and G 21 Indicates that the ring contains A 21 A non-metallic atom group of aromatic rings containing A 21 The aromatic ring of G is a pyridine ring, an imidazole ring, an oxazole ring or a thiazole ring. 22 Indicates that the ring contains A 23 A non-metallic atom group of aromatic rings containing A 23 The aromatic ring is a pyridine ring, an imidazole ring, an oxazole ring or a thiazole ring, In formula 2-3, A 31 and A 32 Each independently represents a nitrogen atom or a phosphorus atom, and B 31 represents a divalent linking group, wherein the divalent linking group is an alkylene group having 2 to 20 carbon atoms, and R 3a and R 3b Each independently represents an alkyl group or a phenyl group, wherein the alkyl group has 1 to 10 carbon atoms, and G 31 Indicates that the ring contains A 31 A non-metallic atom group of aromatic rings containing A 31 The aromatic ring of G is a pyridine ring. 32 Indicates that the ring contains A 32 A non-metallic atom group of aromatic rings containing A 32 The aromatic ring of is a pyridine ring, In formula 2-4, A 41 Each independently represents a nitrogen atom or a phosphorus atom, and B 41 Each independently represents a single bond or a divalent linking group, wherein the divalent linking group is an alkylene group having 1 to 6 carbon atoms, and R 4a , R 4b and R 4c Each independently represents an alkyl group or a phenyl group, wherein the alkyl group has 1 to 6 carbon atoms, and E 41 and E 42 Each independently represents a single bond or an alkyl group having 1 to 6 carbon atoms, R 4a , R 4b and R 4c One of them can be combined with E 41 or E 42 They are bonded to form a ring, and m4 is an integer greater than or equal to 2.

13. A pigment compound having a cyanine pigment structure represented by the following formula 1: In formula 1, L 1 represents a methine chain consisting of 5, 7 or 9 methine groups, R 1 and R 2 Each independently represents an alkyl group, an alkenyl group, an alkynyl group, an aralkyl group or an aryl group, wherein The alkyl group has 1 to 20 carbon atoms, the alkenyl group has 2 to 20 carbon atoms, the alkynyl group has 2 to 20 carbon atoms, the arylalkyl group has 1 to 20 carbon atoms, the aryl group has 6 to 25 carbon atoms, and the aryl group has 6 to 25 carbon atoms. 1 and T 2 Each independently represents a non-metal atom group forming a 5-membered or 6-membered nitrogen-containing heterocyclic ring that may be fused, wherein the nitrogen-containing heterocyclic ring is an oxazole ring, an isoxazole ring, a benzoxazole ring, a naphthoxazole ring, an oxazolocarbazole ring, an oxazolodibenzofuran ring, a thiazole ring, a benzothiazole ring, a naphthothiazole ring, an indolenine ring, a benzoindolenine ring, an imidazole ring, a benzimidazole ring, a naphthoimidazole ring, a quinoline ring, a pyridine ring, a pyrrolopyridine ring, a furanopyrrole ring, an indolizine ring, an imidazoquinoxaline ring or a quinoxaline ring, Cy is an anion moiety, and X 1 represents an organic cation having a flexible molecular structure represented by the following formula 2-1, formula 2-2 or formula 2-3 or an organic cation having a flexible molecular structure represented by formula 2-4, n represents a non-zero number required for neutralizing the charge, In formula 2-1, A 11 and A 12 Each independently represents a nitrogen atom or a phosphorus atom, and B 11 Each independently represents a divalent linking group, wherein the divalent linking group is an alkylene group having 2 to 20 carbon atoms, and R 1a , R 1b , R 1c , R 1d 、E 11 and E 12 Each independently represents an alkyl group or a phenyl group, wherein the alkyl group has 1 to 10 carbon atoms, and R 1a , R 1b , R 1c and R 1d may be bonded to each other to form a ring, m1 is an integer greater than 1, In formula 2-2, A 21 , A 22 and A 23 Each independently represents a nitrogen atom or a phosphorus atom, and B 21 and B 22 Each independently represents a divalent linking group, wherein the divalent linking group is an alkylene group having 2 to 20 carbon atoms, and R 2a and R 2b Each independently represents an alkyl group or a phenyl group, the alkyl group has 1 to 10 carbon atoms, m2 is an integer greater than 0, and G 21 Indicates that the ring contains A 21 A non-metallic atom group of aromatic rings containing A 21 The aromatic ring of G is a pyridine ring, an imidazole ring, an oxazole ring or a thiazole ring. 22 Indicates that the ring contains A 23 A non-metallic atom group of aromatic rings containing A 23 The aromatic ring is a pyridine ring, an imidazole ring, an oxazole ring or a thiazole ring, In formula 2-3, A 31 and A 32 Each independently represents a nitrogen atom or a phosphorus atom, and B 31 represents a divalent linking group, wherein the divalent linking group is an alkylene group having 2 to 20 carbon atoms, and R 3a and R 3b Each independently represents an alkyl group or a phenyl group, wherein the alkyl group has 1 to 10 carbon atoms, and G 31 Indicates that the ring contains A 31 A non-metallic atom group of aromatic rings containing A 31 The aromatic ring of G is a pyridine ring. 32 Indicates that the ring contains A 32 A non-metallic atom group of aromatic rings containing A 32 The aromatic ring of is a pyridine ring, In formula 2-4, A 41 Each independently represents a nitrogen atom or a phosphorus atom, and B 41 Each independently represents a single bond or a divalent linking group, wherein the divalent linking group is an alkylene group having 1 to 6 carbon atoms, and R 4a , R 4b and R 4c Each independently represents an alkyl group or a phenyl group, wherein the alkyl group has 1 to 6 carbon atoms, and E 41 and E 42 Each independently represents a single bond or an alkyl group having 1 to 6 carbon atoms, R 4a , R 4b and R 4c One of them can be combined with E 41 or E 42 They are bonded to form a ring, and m4 is an integer greater than or equal to 2.

14. The pigment compound according to claim 13, wherein In Formula 2-1, Formula 2-2 and Formula 2-3, B 11 , B 21 , B 22 and B 31 Each independently is a divalent linking group having 2 to 8 carbon atoms.

15. The pigment compound according to claim 13 or 14, wherein In Formula 2-1, Formula 2-2, Formula 2-3 and Formula 2-4, A 11 , A 12 , A 21 , A 22 , A 23 , A 31 , A 32 and A 41 A nitrogen atom.

16. The pigment compound according to claim 13 or 14, wherein In Formula 1, X 1 It represents an organic cation having a flexible molecular structure represented by the formula 2-1 or an organic cation having a flexible molecular structure represented by the formula 2-4.

17. The pigment compound according to claim 13 or 14, wherein In the above formula 1, Cy is represented by the following formula 4: In formula 4, Y 1 and Y 2 Represent CR independently 3 R 4 -, -O-, -S-, -Se-, or -NR 5 -, R 3 , R 4 and R 5 Each independently represents a hydrogen atom, an aliphatic group or an aromatic ring group, R 3 and R 4 can bond to each other to form a ring, A 1 and A 2 Each independently represents a non-metallic atom group forming an aromatic ring or an aromatic heterocyclic ring, and L 2 Each independently represents a methine chain consisting of 1, 2 or 3 methine groups, L 2 No substituent, R 6 and R 7 Each independently represents a hydrogen atom or an aliphatic group, R 6 and R 7 can be linked to each other to form a ring, R 8 It is represented by the following formula A, -S A -T A Formula A In formula A, S A represents a single bond, alkylene, alkenylene, alkynylene, -O-, -S-, -NR L1 -, -C(=O)-, -C(=O)O-, -C(=O)NR L1 -、-S(=O)2-、-OR L2 - or a group consisting of at least two of these, R L1 Each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and R L2 represents an alkylene group, an arylene group or a divalent heterocyclic group, T A represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group, a cyano group, a hydroxyl group, a formyl group, a carboxyl group, an amino group, a thiol group, a sulfone group, a phosphoryl group, a boryl group, a vinyl group, an ethynyl group, a trialkylsilyl group or a trialkoxysilyl group.

18. The pigment compound according to claim 17, wherein In the formula 4, A 1 and A 2 Each independently represents a non-metal atom group forming a benzene ring or a naphthalene ring.

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