Compound, dye, and thermal transfer recording ink sheet

Abstract

Provided are: a compound represented by a formula 1; and a use thereof. Descriptions for the reference symbols in formula 1 are omitted.

Description

[Technical Field]

[0001] The present disclosure relates to a compound, a dye, and a thermal transfer recording ink sheet. [Background technology]

[0002] Squarylium compounds are widely used as dyes, and the performance required for such dyes includes a desired hue, optimal spectral absorption, good fastness such as light resistance, moisture resistance, heat resistance, and chemical resistance, and good solubility in solvents.

[0003] For example, Japanese Patent Application Laid-Open No. 2015-86379 describes a squarylium compound in which a benzene ring having a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms is bonded to a nitrogen atom. Japanese Patent Application Laid-Open No. 2019-147935 describes a squarylium compound in which a benzene ring having a halogen atom or a halogenated alkyl group having 1 to 6 carbon atoms is bonded to a nitrogen atom. Japanese Patent Application Laid-Open No. 2020-55956 describes a squarylium compound in which a benzene ring having a substituent is bonded to a nitrogen atom. Summary of the Invention [Problem to be solved by the invention]

[0004] For example, a thermal transfer recording ink sheet containing a squarylium compound as a dye may be used in a high-temperature and high-humidity environment, and therefore the squarylium compound may be required to have improved resistance to moist heat.

[0005] According to the present disclosure, there are provided a compound having excellent wet heat resistance, a dye which is the compound, and an ink sheet for thermal transfer recording which contains the compound. [Means for solving the problem]

[0006] The present disclosure encompasses the following aspects. <1> A compound represented by the following formula 1.

[0007] [ka]

[0008] In formula 1, R 1 and R 2 each independently represents an unsubstituted aliphatic hydrocarbon group or a substituted aliphatic hydrocarbon group, R 3 ~R 8 each independently represents a hydrogen atom or a substituent, Ar 1 and Ar 2 are each independently an aromatic heterocyclic group or a group represented by the following formula 2 or 3:

[0009] [ka]

[0010] In formula 2, R 10 each independently represents a halogen atom or a halogenated alkyl group, R 11 each independently represents an aromatic hydrocarbon group, a heterocyclic group, a cyano group, a silyl group, a nitro group, an imide group, -COR 51 , -COOR 52 , -CONR 53 R 54 , -NR 55 COR 56 , -NR 57 COOR 58 , -NR 59 CONR 60 R 61 , -NR 62 SO2R 63 , -NR 64 SO2NR 65 R 66 , -OCOR 67 , -OCONR 68 R 69 , -SR 70 , -SOR71 , -SO2R 72 , -SO2OR 73 , -SO2NR 74 R 75 , -CSR 76 , -N=NR 77 , -POR 78 R 79 , -OPOR 80 R 81 , -PR 82 R 83 , and -OPR 84 R 85 is a group selected from Group A consisting of R 51 ~R 77 each independently represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; R 78 ~R 85 each independently represents a hydroxy group, an alkoxy group, an aryloxy group, or a hydrocarbon group; R 12 represents an unsubstituted aliphatic hydrocarbon group or an aliphatic hydrocarbon group having at least one substituent selected from the group consisting of a hydroxy group, an alkoxy group, an amino group, and Group A; n1 and n3 each independently represent an integer of 0 to 4, and n2 represents an integer of 0 to 5; At least one of n1 and n2 is an integer of 1 or more, when n1 is 1 or more, at least one of n2 and n3 is an integer of 1 or more; n1+n2+n3 is an integer from 1 to 5, In formula 3, R 13 represents an unsubstituted hydrocarbon group or aromatic heterocyclic group, or a hydrocarbon group or aromatic heterocyclic group having at least one substituent selected from the group consisting of a halogen atom, an aliphatic hydrocarbon group, an alkoxy group, an amino group, and Group A, R 14 is a group selected from the group consisting of a halogen atom, a hydroxy group, an aliphatic hydrocarbon group, and Group A, L 1 is an oxygen atom or NR 15 represents R15 represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; n4 is an integer from 1 to 5, n5 is an integer from 0 to 4, n4+n5 is an integer from 1 to 5, If n4 is 1, L 1 -R 13 is located at the ortho position, or n5 is an integer of 1 or more, In Formula 2 and Formula 3, * indicates the bonding site with the nitrogen atom. <2> Ar 1 and Ar 2 are each independently a group represented by any one of the following formulas 2A, 2B, 3, and 4: <1> The compound described in

[0011] [ka]

[0012] In formula 2A, R 16 is R 10 , R 11 , or R 12 represents R 16 At least one of the following is -COR 51 , -COOR 52 , -CONR 53 R 54 , -NR 55 COR 56 , -NR 59 CONR 60 R 61 , -NR 62 SO2R 63 , or -SO2R 72 and R 51 ~R 56 , R 59 ~R 63 , and R 72 are R in Eq. 2, respectively. 51 ~R 56 , R 59 ~R 63 , and R 72 is synonymous with n6 is an integer from 1 to 5, In formula 2B, R 10 and R 12 are R in Eq. 2, respectively. 10 and R 12 is synonymous with n7 and n8 each independently represent an integer of 1 to 4, n7+n8 is an integer between 2 and 5, In formula 4, A 1 , A 2 , A 3 , A 4 and A 5 is a nitrogen atom or CR 17 represents A 1 , A 2 , A 3 , A 4 and A 5 at least one of is a nitrogen atom, R 17 represents a hydrogen atom or a substituent, and a plurality of R 17 may be linked to each other to form a ring, In Formula 2A, Formula 2B, and Formula 4, * indicates the bonding site with the nitrogen atom. <3> In formula 1, Ar 1 and Ar 2 has a substituent in the ortho position of the ring bonded to the nitrogen atom, <1> or <2> The compound described in <4> Ar 1 and Ar 2 are each independently a group selected from the group consisting of groups represented by the following formulae 2C to 2F, 3A, 3B, and 4A: <1> ~ <3> 1. The compound according to any one of claims 1 to 9.

[0013] [ka]

[0014] In formula 2C, R 18 is R in Eq. 10 , R11 , or R 12 represents n9 is an integer from 0 to 4, In formula 2D, R 19 is R in Eq. 10 , R 11 , or R 12 represents n10 is an integer from 1 to 4, In formula 2E, X 1 represents a halogen atom, R 20 represents a hydrocarbon group or an aromatic heterocyclic group, n11 is an integer from 1 to 4, In formula 2F, X 2 represents a halogen atom, R 21 represents a hydrocarbon group or an aromatic heterocyclic group, n12 is an integer from 1 to 4, In formula 3A, R 14 is R in Equation 3 14 is synonymous with R 22 represents an unsubstituted hydrocarbon group or an aromatic heterocyclic group, or a hydrocarbon group or an aromatic heterocyclic group having at least one substituent selected from Group A, n13 is an integer from 0 to 4, In formula 3B, R 14 is R in Equation 3 14 is synonymous with R 23 represents an unsubstituted hydrocarbon group or an aromatic heterocyclic group, or a hydrocarbon group or an aromatic heterocyclic group having at least one substituent selected from Group A, n14 is an integer from 1 to 4, In formula 4A, R 17 are each independently R in formula 4 17 is synonymous with n15 is an integer from 0 to 3, In Formula 2C and Formula 2D, R 91each independently represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; R 92 each independently represents a hydrocarbon group or a heterocyclic group, In Formula 2C to Formula 2F, Formula 3A, Formula 3B, and Formula 4A, * indicates the bonding site to the nitrogen atom.

[0015] <5> In formula 1, R 3 ~R 8 is a hydrogen atom, <1> ~ <4> 1. The compound according to any one of claims 1 to 9. <6> In formula 1, R 1 and R 2 each independently represents an unsubstituted aliphatic hydrocarbon group; <1> ~ <5> 1. The compound according to any one of claims 1 to 9. <7> In formula 1, R 1 and R 2 each independently represents an aliphatic hydrocarbon group having a polymerizable group, <1> ~ <6> 1. The compound according to any one of claims 1 to 9. <8> <1> ~ <7> A dye comprising the compound according to any one of the above. <9> <1> ~ <7> 10. An ink sheet for thermal transfer recording, comprising the compound according to any one of 8. to 9. [Effects of the Invention]

[0016] According to the present disclosure, there are provided a compound having excellent wet heat resistance, a dye which is the compound, and an ink sheet for thermal transfer recording which contains the compound. DETAILED DESCRIPTION OF THE INVENTION

[0017] Hereinafter, embodiments of the present disclosure will be described in detail. The present disclosure is not limited to the following embodiments. The following embodiments may be modified as appropriate within the scope of the present disclosure.

[0018] In the present disclosure, a numerical range indicated using "to" means a range that includes the numerical values before and after "to" as the lower and upper limits, respectively. In the numerical ranges described in stages in the present disclosure, the upper or lower limit described in a certain numerical range may be replaced with the upper or lower limit of another numerical range described in stages. Furthermore, in the numerical ranges described in the present disclosure, the upper or lower limit described in a certain numerical range may be replaced with a value shown in the examples.

[0019] In the present disclosure, when referring to the amount of each component in a composition, if there are multiple substances corresponding to each component in the composition, it means the total amount of the multiple components present in the composition, unless otherwise specified.

[0020] In the present disclosure, a combination of two or more preferred embodiments is a more preferred embodiment.

[0021] In the present disclosure, 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 is achieved.

[0022] In the present disclosure, when a group (atomic group) is represented without specifying whether it is substituted or unsubstituted, it encompasses both unsubstituted and substituted groups; for example, a "hydrocarbon group" encompasses not only unsubstituted hydrocarbon groups but also substituted hydrocarbon groups.

[0023] In the present disclosure, "(meth)acrylic" is a term that encompasses both "acrylic" and "methacrylic," "(meth)acrylate" is a term that encompasses both "acrylate" and "methacrylate," and "(meth)acryloyl" is a term that encompasses both "acryloyl" and "methacryloyl."

[0024] [Compound] The compound of the present disclosure is a compound represented by the following formula 1:

[0025] [ka]

[0026] In formula 1, R 1 and R 2 each independently represents an unsubstituted aliphatic hydrocarbon group or a substituted aliphatic hydrocarbon group, R 3 ~R 8 each independently represents a hydrogen atom or a substituent, Ar 1 and Ar 2 are each independently an aromatic heterocyclic group or a group represented by the following formula 2 or 3:

[0027] [ka]

[0028] In formula 2, R 10 each independently represents a halogen atom or a halogenated alkyl group, R 11 each independently represents an aromatic hydrocarbon group, a heterocyclic group, a cyano group, a silyl group, a nitro group, an imide group, -COR 51 , -COOR 52 , -CONR 53 R 54 , -NR 55 COR 56 , -NR 57 COOR 58 , -NR 59 CONR 60 R 61 , -NR 62 SO2R 63 , -NR 64 SO2NR 65 R 66 , -OCOR 67 , -OCONR 68 R 69 , -SR 70 , -SOR 71 , -SO2R 72 , -SO2OR 73 , -SO2NR 74 R75 , -CSR 76 , -N=NR 77 , -POR 78 R 79 , -OPOR 80 R 81 , -PR 82 R 83 , and -OPR 84 R 85 is a group selected from Group A consisting of R 51 ~R 77 each independently represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; R 78 ~R 85 each independently represents a hydroxy group, an alkoxy group, an aryloxy group, or a hydrocarbon group; R 12 represents an unsubstituted aliphatic hydrocarbon group or an aliphatic hydrocarbon group having at least one substituent selected from the group consisting of a hydroxy group, an alkoxy group, an amino group, and Group A; n1 and n3 each independently represent an integer of 0 to 4, and n2 represents an integer of 0 to 5; At least one of n1 and n2 is an integer of 1 or more, when n1 is 1 or more, at least one of n2 and n3 is an integer of 1 or more; n1+n2+n3 is an integer from 1 to 5, In formula 3, R 13 represents an unsubstituted hydrocarbon group or aromatic heterocyclic group, or a hydrocarbon group or aromatic heterocyclic group having at least one substituent selected from the group consisting of a halogen atom, an aliphatic hydrocarbon group, an alkoxy group, an amino group, and Group A, R 14 is a group selected from the group consisting of a halogen atom, a hydroxy group, an aliphatic hydrocarbon group, and Group A, L 1 is an oxygen atom or NR 15 represents R 15 represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; n4 is an integer from 1 to 5, n5 is an integer from 0 to 4, n4+n5 is an integer from 1 to 5, If n4 is 1, L 1 -R 13 is located at the ortho position, or n5 is an integer of 1 or more, In Formula 2 and Formula 3, * indicates the bonding site with the nitrogen atom.

[0029] The compound of the present disclosure has excellent resistance to moist heat. The reason why the compound of the present disclosure has excellent resistance to moist heat is not clear, but the compound of Ar 1 and Ar 2 are each independently an aromatic heterocyclic group or a group represented by formula 2 or formula 3, resulting in a sterically or electronically stable structure, which inhibits decomposition and improves solubility based on the steric effect.

[0030] The compound represented by formula 1 will be specifically described below.

[0031] <Expression 1>

[0032] [ka]

[0033] [R 1 and R 2 〕 In formula 1, R 1 and R 2 each independently represents an unsubstituted aliphatic hydrocarbon group or a substituted aliphatic hydrocarbon group.

[0034] R 1 and R 2 and may be the same or different from each other, but are preferably the same from the viewpoint of ease of synthesis.

[0035] (aliphatic hydrocarbon group) The aliphatic hydrocarbon group may be a linear or branched aliphatic hydrocarbon group, and examples of the aliphatic hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group.

[0036] The alkyl group may be a substituted or unsubstituted alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 30. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, an n-octyl group, an eicosyl group, a 2-chloroethyl group, a 2-cyanoethyl group, a benzyl group, a 2-ethylhexyl group, a 2-butyloctyl group, and a 2-t-butylbenzylpropyl group.

[0037] The alkenyl group may be a substituted or unsubstituted alkenyl group. The number of carbon atoms in the alkenyl group is preferably 2 to 30. Specific examples of the alkenyl group include a vinyl group, an allyl group, a prenyl group, a geranyl group, and an oleyl group.

[0038] The alkynyl group may be a substituted or unsubstituted alkynyl group. The number of carbon atoms in the alkynyl group is preferably 2 to 30. Specific examples of the alkynyl group include an ethynyl group and a propargyl group.

[0039] Examples of the substituent that the aliphatic hydrocarbon group may have include a halogen atom, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, a cyano group, a silyl group, a nitro group, an imide group, -OR 48 , -NR 49 R 50 , -COR 51 , -COOR 52 , -CONR 53 R 54 , -NR 55 COR 56 , -NR 57 COOR 58 , -NR 59 CONR 60 R 61 , -NR 62 SO2R 63 , -NR 64 SO2NR65 R 66 , -OCOR 67 , -OCONR 68 R 69 , -SR 70 , -SOR 71 , -SO2R 72 , -SO2OR 73 , -SO2NR 74 R 75 , -CSR 76 , -N=NR 77 , -POR 78 R 79 , -OPOR 80 R 81 , -PR 82 R 83 , and -OPR 84 R 85 Hereinafter, these substituents will be referred to as "substituent T." In addition, "aromatic hydrocarbon group, heterocyclic group, cyano group, silyl group, nitro group, imide group, -COR 51 , -COOR 52 , -CONR 53 R 54 , -NR 55 COR 56 , -NR 57 COOR 58 , -NR 59 CONR 60 R 61 , -NR 62 SO2R 63 , -NR 64 SO2NR 65 R 66 , -OCOR 67 , -OCONR 68 R 69 , -SR 70 , -SOR 71 , -SO2R 72 , -SO2OR 73 , -SO2NR 74 R 75 , -CSR 76 , -POR 77 R 78 , -OPOR 79 R 80 , -PR 81 R 82 、 -OPR83 R 84 , and -N=NR 85 The group consisting of "Group A" is also referred to as Group A. The substituent T includes Group A, a halogen atom, an alicyclic hydrocarbon group, -OR 48 , and -NR 49 R 50 Includes:

[0040] R 48 ~R 77 R each independently represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group. 78 ~R 85 R each independently represents a hydroxy group, an alkoxy group, an aryloxy group, or a hydrocarbon group. 48 ~R 77 The hydrocarbon group and heterocyclic group represented by the formula (R) may have a substituent. 78 ~R 85 The alkoxy group, aryloxy group, and hydrocarbon group represented by the formula (I) may have a substituent.

[0041] (halogen atom) Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0042] (alicyclic hydrocarbon group) Examples of the alicyclic hydrocarbon group include a cycloalkyl group, a bicycloalkyl group, a cycloalkenyl group, and a bicycloalkenyl group. The alicyclic hydrocarbon group may contain multiple rings, such as a spirocyclic skeleton.

[0043] The cycloalkyl group may be a substituted or unsubstituted cycloalkyl group. The number of carbon atoms in the cycloalkyl group is preferably 3 to 30. Specific examples of the cycloalkyl group include a cyclohexyl group, a cyclopentyl group, and a 4-n-dodecylcyclohexyl group.

[0044] The bicycloalkyl group may be a substituted or unsubstituted bicycloalkyl group. The number of carbon atoms in the bicycloalkyl group is preferably 5 to 30. Specific examples of the bicycloalkyl group include a bicyclo[2.2.1]heptan-2-yl group and a bicyclo[2.2.2]octan-3-yl group. The bicycloalkyl group also includes groups having a tricyclo structure with more ring structures.

[0045] The cycloalkenyl group may be a substituted or unsubstituted cycloalkenyl group. The number of carbon atoms in the cycloalkenyl group is preferably 3 to 30. Specific examples of the cycloalkenyl group include a 2-cyclopenten-1-yl group and a 2-cyclohexen-1-yl group.

[0046] The bicycloalkenyl group may be a substituted or unsubstituted bicycloalkenyl group. The number of carbon atoms in the bicycloalkenyl group is preferably 5 to 30. Specific examples of the bicycloalkenyl group include a bicyclo[2.2.1]hept-2-en-1-yl group and a bicyclo[2.2.2]oct-2-en-4-yl group.

[0047] (aromatic hydrocarbon group) The aromatic hydrocarbon group may be a substituted or unsubstituted aromatic hydrocarbon group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 30. Specific examples of the aromatic hydrocarbon group include a phenyl group, a p-tolyl group, a trimethylphenyl group (e.g., a 1,3,5-trimethylphenyl group), a naphthyl group, a m-chlorophenyl group, a t-butylphenyl group, and an o-hexadecanoylaminophenyl group.

[0048] (heterocyclic group) The heterocyclic group may be a substituted or unsubstituted heterocyclic group. A heterocyclic group is a monovalent group obtained by removing one hydrogen atom from an aromatic or non-aromatic heterocyclic compound. The heterocyclic group may be a condensed ring. The heterocyclic group is preferably a 5- or 6-membered heterocyclic group, and more preferably a 5- or 6-membered aromatic heterocyclic group having 3 to 30 carbon atoms. The heteroatoms constituting the ring preferably include at least one selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom. Specific examples of the heterocycle in the heterocyclic group include a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a cinnoline ring, a phthalazine ring, a quinoxaline ring, a pyrrole ring, an indole ring, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrazole ring, an imidazole ring, a benzimidazole ring, a triazole ring, an oxazole ring, a benzoxazole ring, a thiazole ring, a benzothiazole ring, an isothiazole ring, a benzisothiazole ring, a thiadiazole ring, an isoxazole ring, a benzisoxazole ring, a pyrrolidine ring, a piperidine ring, a piperazine ring, an imidazolidine ring, and a thiazoline ring.

[0049] (imide group) Specific examples of the imide group include an N-succinimide group and an N-phthalimide group.

[0050] (-OR 48 ) -OR 48 Examples of the aryl group include a hydroxy group, an alkoxy group, and an aryloxy group.

[0051] The alkoxy group may be a substituted or unsubstituted alkoxy group. The number of carbon atoms in the alkoxy group is preferably 1 to 30. Specific examples of the alkoxy group include a methoxy group, an ethoxy group, an isopropoxy group, an n-octyloxy group, a methoxyethoxy group, a hydroxyethoxy group, and a 3-carboxypropoxy group.

[0052] The aryloxy group may be a substituted or unsubstituted aryloxy group. The number of carbon atoms in the aryloxy group is preferably 6 to 30. Specific examples of the aryloxy group include a phenoxy group, a 2-methylphenoxy group, a 4-tert-butylphenoxy group, a 3-nitrophenoxy group, and a 2-tetradecanoylaminophenoxy group.

[0053] (-NR 49 R 50 ) -NR 49 R 50 Examples of the aliphatic amino group include an aliphatic amino group, an arylamino group, and a heterocyclic amino group. The aliphatic amino group may be a linear or branched aliphatic amino group. The aliphatic amino group preferably has 1 to 30 carbon atoms. Examples of the aliphatic amino group include a monoalkylamino group and a dialkylamino group. Specific examples of the aliphatic amino group, the arylamino group, and the heterocyclic amino group include a methylamino group, a dimethylamino group, an anilino group, an N-methyl-anilino group, a diphenylamino group, a hydroxyethylamino group, a carboxyethylamino group, a sulfoethylamino group, a 3,5-dicarboxyanilino group, and a 4-quinolylamino group.

[0054] (-COR 51 ) -COR 51 Examples of -COR include a formyl group, an aliphatic carbonyl group having 2 to 30 carbon atoms (e.g., an alkylcarbonyl group), an arylcarbonyl group having 7 to 30 carbon atoms, and a heterocyclic carbonyl group having 4 to 30 carbon atoms and bonded to a carbonyl group via a carbon atom. 51 Specific examples include an acetyl group, a pivaloyl group, a 2-chloroacetyl group, a stearoyl group, a benzoyl group, a pn-octyloxyphenylcarbonyl group, a 2-pyridylcarbonyl group, and a 2-furylcarbonyl group.

[0055] (-COOR 52 ) -COOR 52Examples of the oxycarbonyl group include an aliphatic oxycarbonyl group and an aryloxycarbonyl group.

[0056] The aliphatic oxycarbonyl group may be a substituted or unsubstituted aliphatic oxycarbonyl group. The aliphatic oxycarbonyl group preferably has 2 to 30 carbon atoms. Examples of the aliphatic oxycarbonyl group include an alkoxycarbonyl group. Specific examples of the aliphatic oxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a tert-butoxycarbonyl group, and an n-octadecyloxycarbonyl group.

[0057] The aryloxycarbonyl group may be a substituted or unsubstituted aryloxycarbonyl group. The number of carbon atoms in the aryloxycarbonyl group is preferably 7 to 30. Specific examples of the aryloxycarbonyl group include a phenoxycarbonyl group, an o-chlorophenoxycarbonyl group, an m-nitrophenoxycarbonyl group, and a p-tert-butylphenoxycarbonyl group.

[0058] In addition, -COOR 52 R 52 When is a hydrogen atom (carboxy group), the terminal hydrogen atom may be dissociated or may be in the form of a salt.

[0059] (-CONR 53 R 54 ) -CONR 53 R 54 Examples of the carbamoyl group include a substituted or unsubstituted carbamoyl group. The number of carbon atoms in the carbamoyl group is preferably 1 to 30. Specific examples of the carbamoyl group include an unsubstituted carbamoyl group, an N-methylcarbamoyl group, an N,N-dimethylcarbamoyl group, an N,N-di-n-octylcarbamoyl group, and an N-(methylsulfonyl)carbamoyl group.

[0060] (-NR 55 COR 56 ) -NR 55 COR56 Examples of —NR include a formylamino group, an alkylcarbonylamino group having 2 to 30 carbon atoms, and an arylcarbonylamino group having 6 to 30 carbon atoms. 55 COR 56 Specific examples include a formylamino group, an acetylamino group, a pivaloylamino group, a lauroylamino group, a benzoylamino group, and a 3,4,5-tri-n-octyloxyphenylcarbonylamino group.

[0061] (-NR 57 COOR 58 ) -NR 57 COOR 58 Examples of the amino group include an aliphatic oxycarbonylamino group and an aryloxycarbonylamino group.

[0062] The aliphatic oxycarbonylamino group may be a substituted or unsubstituted aliphatic oxycarbonylamino group. The number of carbon atoms in the aliphatic oxycarbonylamino group is preferably 2 to 30. Examples of the aliphatic oxycarbonylamino group include an alkoxycarbonylamino group. Specific examples of the aliphatic oxycarbonylamino group include a methoxycarbonylamino group, an ethoxycarbonylamino group, a tert-butoxycarbonylamino group, an n-octadecyloxycarbonylamino group, and an N-methylmethoxycarbonylamino group.

[0063] The aryloxycarbonylamino group may be a substituted or unsubstituted aryloxycarbonylamino group. The number of carbon atoms in the aryloxycarbonylamino group is preferably 7 to 30. Specific examples of the aryloxycarbonylamino group include a phenoxycarbonylamino group, a p-chlorophenoxycarbonylamino group, and an n-octyloxyphenoxycarbonylamino group.

[0064] In addition, -NR 57 COOR 58 R 58When is a hydrogen atom, the terminal hydrogen atom may be dissociated or may be in the form of a salt.

[0065] (-NR 59 CONR 60 R 61 ) -NR 59 CONR 60 R 61 Examples of the aminocarbonylamino group include a substituted or unsubstituted aminocarbonylamino group. The number of carbon atoms in the aminocarbonylamino group is preferably 1 to 30. Specific examples of the aminocarbonylamino group include a carbamoylamino group, an N,N-dimethylaminocarbonylamino group, an N,N-diethylaminocarbonylamino group, and a morpholinocarbonylamino group.

[0066] (-NR 62 SO2R 63 ) -NR 62 SO2R 63 Examples of the sulfonylamino group include an aliphatic sulfonylamino group and an arylsulfonylamino group.

[0067] The aliphatic sulfonylamino group may be a substituted or unsubstituted aliphatic sulfonylamino group. The number of carbon atoms in the aliphatic sulfonylamino group is preferably 1 to 30. Examples of the aliphatic sulfonylamino group include alkylsulfonylamino groups. Specific examples of the aliphatic sulfonylamino group include a methylsulfonylamino group and a butylsulfonylamino group.

[0068] The arylsulfonylamino group may be a substituted or unsubstituted arylsulfonylamino group. The number of carbon atoms in the arylsulfonylamino group is preferably 6 to 30. Specific examples of the arylsulfonylamino group include a phenylsulfonylamino group, a 2,3,5-trichlorophenylsulfonylamino group, and a p-methylphenylsulfonylamino group.

[0069] (-NR 64 SO2NR 65 R66 ) -NR 64 SO2NR 65 R 66 Examples of the sulfamoylamino group include a sulfamoylamino group. The sulfamoylamino group may be a substituted or unsubstituted sulfamoylamino group. The number of carbon atoms in the sulfamoylamino group is preferably 0 to 30. Specific examples of the sulfamoylamino group include a sulfamoylamino group, an N,N-dimethylaminosulfonylamino group, and an Nn-octylaminosulfonylamino group.

[0070] (-OCOR 67 ) -OCOR 67 Examples of the aryloxy group include a formyloxy group, an alkylcarbonyloxy group, and an arylcarbonyloxy group.

[0071] The alkylcarbonyloxy group may be a substituted or unsubstituted alkylcarbonyloxy group. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 30. Examples of the alkylcarbonyloxy group include an acetyloxy group, a pivaloyloxy group, a stearoyloxy group, an acryloyloxy group, and a methacryloyloxy group.

[0072] The arylcarbonyloxy group may be a substituted or unsubstituted arylcarbonyloxy group. The number of carbon atoms in the arylcarbonyloxy group is preferably 7 to 30. Examples of the arylcarbonyloxy group include a benzoyloxy group and a p-methoxyphenylcarbonyloxy group.

[0073] (-OCONR 68 R 69 ) -OCONR 68 R 69Examples of the carbamoyloxy group include a carbamoyloxy group. The carbamoyloxy group may be a substituted or unsubstituted carbamoyloxy group. The number of carbon atoms in the carbamoyloxy group is preferably 1 to 30. Specific examples of the carbamoyloxy group include an N,N-dimethylcarbamoyloxy group, an N,N-diethylcarbamoyloxy group, a morpholinocarbonyloxy group, an N,N-di-n-octylaminocarbonyloxy group, and an Nn-octylcarbamoyloxy group.

[0074] (-SR 70 ) -SR 70 Examples of the thio group include a mercapto group, an aliphatic thio group, an arylthio group, and a heteroarylthio group.

[0075] The aliphatic thio group may be a substituted or unsubstituted aliphatic thio group. Examples of the aliphatic thio group include an alkylthio group. The number of carbon atoms in the aliphatic thio group is preferably 1 to 30. Specific examples of the alkylthio group include a methylthio group, an ethylthio group, and an n-hexadecylthio group.

[0076] The arylthio group may be a substituted or unsubstituted arylthio group. The number of carbon atoms in the arylthio group is preferably 6 to 12. Specific examples of the arylthio group include a phenylthio group, a 1-naphthylthio group, and a 2-naphthylthio group.

[0077] The heteroarylthio group may be a substituted or unsubstituted heteroarylthio group. The number of carbon atoms in the heteroarylthio group is preferably 6 to 12. Specific examples of the heteroarylthio group include a pyridylthio group, a pyrimidylthio group, an indolylthio group, a benzothiazolylthio group, a benzimidazolylthio group, a furylthio group, a thienylthio group, a pyrazolylthio group, and an imidazolylthio group.

[0078] (-SOR 71 ) -SOR 71Examples of the sulfinyl group include an aliphatic sulfinyl group and an arylsulfinyl group.

[0079] The aliphatic sulfinyl group may be a substituted or unsubstituted aliphatic sulfinyl group. The number of carbon atoms in the aliphatic sulfinyl group is preferably 1 to 30. Examples of the aliphatic sulfinyl group include alkylsulfinyl groups. Specific examples of the aliphatic sulfinyl group include a methylsulfinyl group and an ethylsulfinyl group.

[0080] The arylsulfinyl group may be a substituted or unsubstituted arylsulfinyl group. The number of carbon atoms in the arylsulfinyl group is preferably 6 to 30. Specific examples of the arylsulfinyl group include a phenylsulfinyl group and a p-methylphenylsulfinyl group.

[0081] (-SO2R 72 ) -SO2R 72 Examples of the sulfonyl group include an aliphatic sulfonyl group and an arylsulfonyl group.

[0082] The aliphatic sulfonyl group may be a substituted or unsubstituted aliphatic sulfonyl group. The number of carbon atoms in the aliphatic sulfonyl group is preferably 1 to 30. Examples of the aliphatic sulfonyl group include alkylsulfonyl groups. Specific examples of the aliphatic sulfonyl group include a methylsulfonyl group and an ethylsulfonyl group.

[0083] The arylsulfonyl group may be a substituted or unsubstituted arylsulfonyl group. The number of carbon atoms in the arylsulfonyl group is preferably 6 to 30. Specific examples of the arylsulfonyl group include a phenylsulfonyl group and a p-toluenesulfonyl group.

[0084] (-SO2OR 73 ) -SO2OR 73 Examples of the aryloxysulfonyl group include an aliphatic oxysulfonyl group and an aryloxysulfonyl group.

[0085] The aliphatic oxysulfonyl group may be a substituted or unsubstituted aliphatic oxysulfonyl group. The number of carbon atoms in the aliphatic oxysulfonyl group is preferably 1 to 30. Examples of the aliphatic oxysulfonyl group include an alkoxysulfonyl group. Specific examples of the aliphatic oxysulfonyl group include a methoxysulfonyl group, an ethoxysulfonyl group, and an n-butoxysulfonyl group.

[0086] The aryloxysulfonyl group may be a substituted or unsubstituted aryloxysulfonyl group. The number of carbon atoms in the aryloxysulfonyl group is preferably 6 to 12. Specific examples of the aryloxysulfonyl group include a phenoxysulfonyl group and a 2-naphthoxyphenyl group.

[0087] In addition, -SO2OR 73 R 73 When is a hydrogen atom (sulfo group), the terminal hydrogen atom may be dissociated or may be in the form of a salt.

[0088] (-SO2NR 74 R 75 ) -SO2NR 74 R 75 Examples of the sulfamoyl group include a substituted or unsubstituted sulfamoyl group. The number of carbon atoms in the sulfamoyl group is preferably 0 to 30. Specific examples of the sulfamoyl group include an N-ethylsulfamoyl group, an N-(3-dodecyloxypropyl)sulfamoyl group, an N,N-dimethylsulfamoyl group, an N-acetylsulfamoyl group, an N-benzoylsulfamoyl group, and an N-(N'-phenylcarbamoyl)sulfamoyl group.

[0089] (-CSR 76 ) -CSR 76 Examples of the thiocarbonyl group include an aliphatic thiocarbonyl group and an aryl thiocarbonyl group.

[0090] The aliphatic thiocarbonyl group may be a substituted or unsubstituted aliphatic thiocarbonyl group. The number of carbon atoms in the aliphatic thiocarbonyl group is preferably 1 to 30. Specific examples of the aliphatic thiocarbonyl group include a methylthiocarbonyl group and an ethylthiocarbonyl group.

[0091] The arylthiocarbonyl group may be a substituted or unsubstituted aliphatic thiocarbonyl group. The number of carbon atoms in the arylthiocarbonyl group is preferably 1 to 30. Specific examples of the arylthiocarbonyl group include a phenylthiocarbonyl group and a naphthylthiocarbonyl group.

[0092] (-N=NR 77 ) -N=NR 77 Examples of the azo group include aryl azo groups and heterocyclic azo groups.

[0093] The arylazo group may be a substituted or unsubstituted arylazo group. Specific examples of the arylazo group include a phenylazo group and a methoxyphenylazo group.

[0094] The heterocyclic azo group may be a substituted or unsubstituted heterocyclic azo group. Specific examples of the heterocyclic azo group include a 4-pivaloylaminophenylazo group and a 2-hydroxy-4-propanoylphenylazo group.

[0095] (-POR 78 R 79 ) -POR 78 R 79 Examples of the phosphinyl group include an aliphatic phosphinyl group and an aryl phosphinyl group.

[0096] The aliphatic phosphinyl group may be a substituted or unsubstituted aliphatic phosphinyl group. The number of carbon atoms in the aliphatic phosphinyl group is preferably 1 to 30. Examples of the aliphatic phosphinyl group include a dialkylphosphinyl group and a dialkoxyphosphinyl group. Specific examples of the aliphatic phosphinyl group include a dimethylphosphinyl group and a dimethoxyphosphinyl group.

[0097] The arylphosphinyl group may be a substituted or unsubstituted arylphosphinyl group. The number of carbon atoms in the arylphosphinyl group is preferably 6 to 30. Specific examples of the arylphosphinyl group include a diphenylphosphinyl group and a diphenoxyphosphinyl group.

[0098] In addition, -POR 78 R 79 R 78 and R 79 When is a hydroxy group (phosphonic acid group), the terminal hydrogen atom may be dissociated or may be in the form of a salt.

[0099] (-OPOR 80 R 81 ) -OPOR 80 R 81 Examples of the phosphinyloxy group include an aliphatic phosphinyloxy group and an aryl phosphinyloxy group.

[0100] The aliphatic phosphinyloxy group may be a substituted or unsubstituted aliphatic phosphinyloxy group. The number of carbon atoms in the aliphatic phosphinyloxy group is preferably 1 to 30. Examples of the aliphatic phosphinyloxy group include a dialkylphosphinyloxy group and a dialkoxyphosphinyloxy group. Specific examples of the aliphatic phosphinyloxy group include a dimethylphosphinyloxy group and a dimethoxyphosphinyloxy group.

[0101] The arylphosphinyloxy group may be a substituted or unsubstituted arylphosphinyloxy group. The number of carbon atoms in the arylphosphinyloxy group is preferably 6 to 30. Specific examples of the arylphosphinyloxy group include a diphenylphosphinyloxy group and a diphenoxyphosphinyloxy group.

[0102] In addition, -OPOR 80 R 81 R 80 and R 81 When is a hydroxy group (phosphate group), the terminal hydrogen atom may be dissociated or may be in the form of a salt.

[0103] (-PR 82 R 83 ) -PR 82 R 83 Examples of the phosphino group include an aliphatic phosphino group and an aryl phosphino group.

[0104] The aliphatic phosphino group may be a substituted or unsubstituted aliphatic phosphino group. The number of carbon atoms in the aliphatic phosphino group is preferably 1 to 30. Examples of the aliphatic phosphino group include a dialkylphosphino group and a dialkoxyphosphino group. Specific examples of the aliphatic phosphino group include a dimethylphosphino group and a dimethoxyphosphino group.

[0105] The arylphosphino group may be a substituted or unsubstituted arylphosphino group. The number of carbon atoms in the arylphosphino group is preferably 6 to 30. Specific examples of the arylphosphino group include a diphenylphosphino group and a diphenoxyphosphino group.

[0106] (-OPR 84 R 85 ) -OPR 84 R 85 Examples of the phosphinoxy group include an aliphatic phosphinooxy group and an aryl phosphinooxy group.

[0107] The aliphatic phosphino group may be a substituted or unsubstituted aliphatic phosphinooxy group. The number of carbon atoms in the aliphatic phosphino group is preferably 1 to 30. Examples of the aliphatic phosphino group include a dialkylphosphinooxy group and a dialkoxyphosphinooxy group. Specific examples of the aliphatic phosphinooxy group include a dimethylphosphinooxy group and a dimethoxyphosphinooxy group.

[0108] The arylphosphinooxy group may be a substituted or unsubstituted arylphosphinooxy group. The number of carbon atoms in the arylphosphinooxy group is preferably 6 to 30. Specific examples of the arylphosphino group include a diphenylphosphinooxy group and a diphenoxyphosphinooxy group.

[0109] (R 48 ~R 77 ) R 48 ~R 77 The hydrocarbon group represented by the formula (I) may be any of an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group.

[0110] Specific examples of the aliphatic hydrocarbon group include R 1 and R 2 Specific examples of the aliphatic hydrocarbon group include those represented by the following formula:

[0111] Specific examples of the aromatic hydrocarbon group include the specific examples of the aromatic hydrocarbon group for the substituent T above.

[0112] Specific examples of the alicyclic hydrocarbon group include the specific examples of the alicyclic hydrocarbon group for the substituent T described above.

[0113] R 48 ~R 77 Specific examples of the heterocyclic group represented by the following formula include the specific examples of the heterocyclic group for the substituent T above.

[0114] (R 78 ~R 85 ) R78 ~R 85 The hydrocarbon group represented by R may be any of an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. 78 ~R 85 Specific examples of hydrocarbon groups represented by R 48 ~R 77 Specific examples of hydrocarbon groups include those represented by the following formula:

[0115] R 78 ~R 85 Specific examples of the alkoxy group and aryloxy group represented by the following formula include the specific examples of the alkoxy group and aryloxy group for the substituent T described above.

[0116] Among them, R 1 and R 2 Preferably, each independently represents an unsubstituted aliphatic hydrocarbon group.

[0117] The unsubstituted aliphatic hydrocarbon group is preferably a branched alkyl group, more preferably a branched alkyl group having 4 to 20 carbon atoms.

[0118] Also, R 1 and R 2 Preferably, each independently represents an aliphatic hydrocarbon group having a polymerizable group.

[0119] The polymerizable group may be a photopolymerizable group or a thermally polymerizable group.

[0120] The photopolymerizable group means a group that can undergo a polymerization reaction or a crosslinking reaction by the action of light (that is, active energy rays such as ultraviolet light, visible light, electron beams, γ rays, β rays, etc.).

[0121] The thermally polymerizable group means a group that can undergo a polymerization reaction or a crosslinking reaction by the action of heat.

[0122] The polymerizable group is preferably a photopolymerizable group.

[0123] The photopolymerizable group may be a radically polymerizable group or a cationically polymerizable group. Examples of the radically polymerizable group include ethylenically unsaturated groups (e.g., vinyl, acryloyloxy, methacryloyl, styryl, and maleimide groups). Examples of the cationically polymerizable group include epoxy and oxetane groups.

[0124] [R 3 ~R 8 〕 In formula 1, R 3 ~R 8 each independently represents a hydrogen atom or a substituent.

[0125] R 3 ~R 8 may be the same or different from each other, but from the viewpoint of ease of synthesis, R 3 and R 5 , R 4 and R 6 , R 7 and R 8 are preferably the same.

[0126] R 3 ~R 8 Examples of the substituent represented by the formula include the above-mentioned substituent T.

[0127] Among them, R 3 ~R 8 is preferably a hydrogen atom.

[0128] [Ar 1 and Ar 2 〕 In formula 1, Ar 1 and Ar 2 are each independently an aromatic heterocyclic group or a group represented by the following formula 2 or 3. The group represented by formula 2 and the group represented by formula 3 will be described in detail later.

[0129] Ar 1 and Ar 2 and may be the same or different from each other, but are preferably the same from the viewpoint of ease of synthesis.

[0130] [ka]

[0131] In formula 2, R 10 each independently represents a halogen atom or a halogenated alkyl group, R 11 each independently represents an aromatic hydrocarbon group, a heterocyclic group, a cyano group, a silyl group, a nitro group, an imide group, -COR 51 , -COOR 52 , -CONR 53 R 54 , -NR 55 COR 56 , -NR 57 COOR 58 , -NR 59 CONR 60 R 61 , -NR 62 SO2R 63 , -NR 64 SO2NR 65 R 66 , -OCOR 67 , -OCONR 68 R 69 , -SR 70 , -SOR 71 , -SO2R 72 , -SO2OR 73 , -SO2NR 74 R 75 , -CSR 76 , -N=NR 77 , -POR 78 R 79 , -OPOR 80 R 81 , -PR 82 R 83 , and -OPR 84 R 85 is a group selected from Group A consisting of R 51 ~R 77 each independently represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; R 78 ~R 85each independently represents a hydroxy group, an alkoxy group, an aryloxy group, or a hydrocarbon group; R 12 represents an unsubstituted aliphatic hydrocarbon group or an aliphatic hydrocarbon group having at least one substituent selected from the group consisting of a hydroxy group, an alkoxy group, an amino group, and Group A; n1 and n3 each independently represent an integer of 0 to 4, and n2 represents an integer of 0 to 5; At least one of n1 and n2 is an integer of 1 or more, when n1 is 1 or more, at least one of n2 and n3 is an integer of 1 or more; n1+n2+n3 is an integer from 1 to 5, In formula 3, R 13 represents an unsubstituted hydrocarbon group or aromatic heterocyclic group, or a hydrocarbon group or aromatic heterocyclic group having at least one substituent selected from the group consisting of a halogen atom, an aliphatic hydrocarbon group, an alkoxy group, an amino group, and Group A, R 14 is a group selected from the group consisting of a halogen atom, a hydroxy group, an aliphatic hydrocarbon group, and Group A, L 1 is an oxygen atom or NR 15 represents R 15 represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; n4 is an integer from 1 to 5, n5 is an integer from 0 to 4, n4+n5 is an integer from 1 to 5, If n4 is 1, L 1 -R 13 is located at the ortho position, or n5 is an integer of 1 or more, In Formula 2 and Formula 3, * indicates the bonding site with the nitrogen atom.

[0132] Also, Ar 1 and Ar 2are preferably each independently a group represented by any one of the following formula 2A, formula 2B, formula 3, and formula 4. The group represented by formula 2A, the group represented by formula 2B, and the group represented by formula 4 will be described in detail later.

[0133] [ka]

[0134] In formula 2A, R 16 is R 10 , R 11 , or R 12 represents R 16 At least one of the 51 , -COOR 52 , -CONR 53 R 54 , -NR 55 COR 56 , -NR 59 CONR 60 R 61 , -NR 62 SO2R 63 , or -SO2R 72 and R 51 ~R 56 , R 59 ~R 63 , and R 72 are R in Eq. 2, respectively. 51 ~R 56 , R 59 ~R 63 , and R 72 is synonymous with n6 is an integer from 1 to 5, In formula 2B, R 10 and R 12 are R in Eq. 2, respectively. 10 and R 12 is synonymous with n7 and n8 each independently represent an integer of 1 to 4, n7+n8 is an integer between 2 and 5, In formula 4, A 1 , A 2, A 3 , A 4 and A 5 is a nitrogen atom or CR 17 represents A 1 , A 2 , A 3 , A 4 and A 5 at least one of is a nitrogen atom, R 17 represents a hydrogen atom or a substituent, and a plurality of R 17 may be linked to each other to form a ring, In Formula 2A, Formula 2B, and Formula 4, * indicates the bonding site with the nitrogen atom.

[0135] Also, Ar 1 and Ar 2 Preferably, Ar has a substituent at the ortho position of the ring bonded to the nitrogen atom. 1 and Ar 2 In the formula (I), at least one of the two carbon atoms adjacent to the carbon atom bonded to the nitrogen atom preferably has a substituent.

[0136] Specifically, Ar 1 and Ar 2 are preferably each independently a group selected from the group consisting of groups represented by the following formulae 2C to 2F, 3A, 3B, and 4A. Details of the groups represented by formulae 2C to 2F, 3A, 3B, and 4A will be described later.

[0137] [ka]

[0138] In formula 2C, R 18 is R in Eq. 10 , R 11 , or R 12 represents n9 is an integer from 0 to 4, In formula 2D, R 19 is R in Eq.10 , R 11 , or R 12 represents n10 is an integer from 1 to 4, In formula 2E, X 1 represents a halogen atom, R 20 represents a hydrocarbon group or an aromatic heterocyclic group, n11 is an integer from 1 to 4, In formula 2F, X 2 represents a halogen atom, R 21 represents a hydrocarbon group or an aromatic heterocyclic group, n12 is an integer from 1 to 4, In formula 3A, R 14 is R in Equation 3 14 is synonymous with R 22 represents an unsubstituted hydrocarbon group or an aromatic heterocyclic group, or a hydrocarbon group or an aromatic heterocyclic group having at least one substituent selected from Group A, n13 is an integer from 0 to 4, In formula 3B, R 14 is R in Equation 3 14 is synonymous with R 23 represents an unsubstituted hydrocarbon group or an aromatic heterocyclic group, or a hydrocarbon group or an aromatic heterocyclic group having at least one substituent selected from Group A, n14 is an integer from 1 to 4, In formula 4A, R 17 are each independently R in formula 4 17 is synonymous with n15 is an integer from 0 to 3, In Formula 2C and Formula 2D, R 81 each independently represents a hydrogen atom, a hydrocarbon group, or an aromatic heterocyclic group; R 82 each independently represents a hydrocarbon group or an aromatic heterocyclic group, In Formula 2C to Formula 2F, Formula 3A, Formula 3B, and Formula 4A, * indicates the bonding site to the nitrogen atom.

[0139] (aromatic heterocyclic group) In one embodiment, Ar 1 and Ar 2 are each independently an aromatic heterocyclic group. An aromatic heterocyclic group is a monovalent group formed by removing one hydrogen atom from an aromatic heterocyclic compound. The aromatic heterocyclic group may be a condensed ring.

[0140] Ar 1 and Ar 2 The number of carbon atoms in the aromatic heterocyclic group represented by the formula (I) is preferably 3 to 30. The heteroatoms constituting the ring of the aromatic heterocyclic group preferably include at least one selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms, and more preferably include a nitrogen atom. The ring of the aromatic heterocyclic group is preferably a 5- or 6-membered ring, and more preferably a 6-membered ring. Examples of the ring of the aromatic heterocyclic group include a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a cinnoline ring, a phthalazine ring, a quinoxaline ring, a pyrrole ring, an indole ring, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrazole ring, an imidazole ring, a benzimidazole ring, a triazole ring, an oxazole ring, a benzoxazole ring, a thiazole ring, a benzothiazole ring, an isothiazole ring, a benzisothiazole ring, a thiadiazole ring, an isoxazole ring, and a benzisoxazole ring.

[0141] (Group represented by formula 4) Ar 1 and Ar 2 are each preferably independently a group represented by formula 4. The group represented by formula 4 is one embodiment of an aromatic heterocyclic group.

[0142] [ka]

[0143] [A 1 , A 2 , A 3 , A 4 and A 5 〕 In formula 4, A 1 , A 2 , A 3 , A 4 and A 5 is a nitrogen atom or CR 17 represents A 1 , A 2 , A 3 , A 4 and A 5 At least one of the groups is a nitrogen atom. The number of nitrogen atoms is preferably 1 to 3.

[0144] R 17 represents a hydrogen atom or a substituent, and a plurality of R 17 may be linked to each other to form a ring. 17 Examples of the substituent represented by the formula (I) include the above-mentioned substituent T. 17 The ring formed by linking together is preferably a 5-membered ring or a 6-membered ring. 17 The ring formed by linking together R may be a monocyclic ring or a polycyclic ring. 17 The ring formed by linking these is preferably a benzene ring.

[0145] (Group represented by formula 4A) Ar 1 and Ar 2 are each independently a group represented by formula 4A.

[0146] [ka]

[0147] [R 17 〕 In formula 4A, R 17 are each independently R in formula 4 17 Two or more R 17 may be the same or different from each other.

[0148] [n15] In formula 4A, n15 is an integer of 0 to 3, and preferably 0 to 1.

[0149] (Group represented by formula 2) In one embodiment, Ar 1 and Ar 2 are each independently a group represented by formula 2.

[0150] [ka]

[0151] [R 10 〕 In formula 2, R 10 each independently represents a halogen atom or a halogenated alkyl group.

[0152] Specific examples of the halogen atom include the specific examples of the halogen atom in the above-mentioned substituent T. Among them, the halogen atom is preferably a fluorine atom or a chlorine atom, and more preferably a chlorine atom.

[0153] The halogenated alkyl group refers to a group in which at least one hydrogen atom contained in an alkyl group is replaced with a halogen atom. Specific examples of the halogen atom contained in the halogenated alkyl group include the specific examples of the halogen atom in the substituent T. Among them, the halogen atom is preferably a fluorine atom or a chlorine atom, and more preferably a chlorine atom.

[0154] [R 11 〕 In formula 2, R 11 each independently represents an aromatic hydrocarbon group, a heterocyclic group, a cyano group, a silyl group, a nitro group, an imide group, -COR 51 , -COOR 52 , -CONR 53 R 54 , -NR 55 COR 56 , -NR57 COOR 58 , -NR 59 CONR 60 R 61 , -NR 62 SO2R 63 , -NR 64 SO2NR 65 R 66 , -OCOR 67 , -OCONR 68 R 69 , -SR 70 , -SOR 71 , -SO2R 72 , -SO2OR 73 , -SO2NR 74 R 75 , -CSR 76 , -N=NR 77 , -POR 78 R 79 , -OPOR 80 R 81 , -PR 82 R 83 , and -OPR 84 R 85 is a group selected from Group A consisting of R 51 ~R 77 each independently represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; R 78 ~R 85 each independently represents a hydroxy group, an alkoxy group, an aryloxy group, or a hydrocarbon group.

[0155] Specific examples of Group A include the specific examples of Group A included in the above-mentioned Substituent T.

[0156] Among them, R 11 -COOR 52 , -CONR 53 R 54 , -NR 55 COR 56 , -NR 62 SO2R 63 , or -SO2R 72 is preferably —NR 55 COR 56で It is more preferable to have one.

[0157] [R 12 〕 In formula 2, R 12 is an unsubstituted aliphatic hydrocarbon group or an aliphatic hydrocarbon group having at least one substituent selected from the group consisting of a hydroxy group, an alkoxy group, an amino group, and the above-mentioned Group A.

[0158] The aliphatic hydrocarbon group is R 1 and R 2 Specific examples of the aliphatic hydrocarbon group include those represented by the following formula:

[0159] [n1, n2, n3] In formula 2, n1 and n3 are each independently an integer of 0 to 4, and n2 is an integer of 0 to 5. At least one of n1 and n2 is an integer of 1 or greater. When n1 is 1 or greater, at least one of n2 and n3 is an integer of 1 or greater. n1+n2+n3 is an integer of 1 to 5.

[0160] (Group represented by formula 2A) Ar 1 and Ar 2 are each independently preferably a group represented by formula 2A. The group represented by formula 2A is one embodiment of the group represented by formula 2.

[0161] [ka]

[0162] [R 16 〕 In formula 2A, R 16 is the above R 10 , the above R 11 , or the above R 12 That is, R 16 is a halogen atom, a halogenated alkyl group, a group selected from the above Group A, an unsubstituted aliphatic hydrocarbon group, or an aliphatic hydrocarbon group having at least one substituent selected from the group consisting of a hydroxy group, an alkoxy group, an amino group, and Group A.

[0163] R 16 At least one of the following is -COR 51 , -COOR 52 , -CONR 53 R 54 , -NR 55 COR 56 , -NR 59 CONR 60 R 61 , -NR 62 SO2R 63 , or -SO2R 72 and -NR 55 COR 56 It is preferable that: R 51 ~R 56 , R 59 ~R 63 , and R 72 are R in Eq. 2, respectively. 51 ~R 56 , R 59 ~R 63 , and R 72 is synonymous with.

[0164] [n6] In formula 2A, n6 is an integer of 1 to 5, and preferably 2 to 4.

[0165] (Group represented by formula 2B) Ar 1 and Ar 2 are each preferably independently a group represented by formula 2B. The group represented by formula 2B is one embodiment of the group represented by formula 2.

[0166] [ka]

[0167] [R 10 , R 12 〕 In formula 2B, R 10 and R 12 are R in Eq. 2, respectively. 10 and R 12 is synonymous with.

[0168] [n7, n8] n7 and n8 each independently represent an integer of 1 to 4, n7+n8 is an integer from 2 to 5.

[0169] (Group represented by formula 2C) Ar 1 and Ar 2 are each preferably independently a group represented by formula 2C. The group represented by formula 2C is one embodiment of the group represented by formula 2A.

[0170] [ka]

[0171] [R 18 〕 In formula 2C, R 18 is the above R in Equation 2 10 , the above R 11 , or the above R 12 That is, R 18 is a halogen atom, a halogenated alkyl group, a group selected from the above Group A, an unsubstituted aliphatic hydrocarbon group, or an aliphatic hydrocarbon group having at least one substituent selected from the group consisting of a hydroxy group, an alkoxy group, an amino group, and Group A.

[0172] [n9] In formula 2C, n9 is an integer of 0 to 4.

[0173] [R 91 〕 In formula 2C, R 91 R each independently represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group. 91 is preferably a hydrogen atom or a hydrocarbon group, more preferably an alkyl group, even more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group or an ethyl group.

[0174] [R 92 〕 In formula 2C, R 92R each independently represents a hydrocarbon group or a heterocyclic group. 92 is preferably a hydrocarbon group, more preferably an alkyl group, and even more preferably an alkyl group having 1 to 20 carbon atoms.

[0175] (Group represented by formula 2D) Ar 1 and Ar 2 are each preferably independently a group represented by formula 2D. The group represented by formula 2D is one embodiment of the group represented by formula 2A.

[0176] [ka]

[0177] [R 19 〕 In formula 2D, R 19 is the above R in Equation 2 10 , the above R 11 , or the above R 12 That is, R 19 is a halogen atom, a halogenated alkyl group, a group selected from the above Group A, an unsubstituted aliphatic hydrocarbon group, or an aliphatic hydrocarbon group having at least one substituent selected from the group consisting of a hydroxy group, an alkoxy group, an amino group, and Group A.

[0178] [n10] In formula 2D, n10 is an integer of 1 to 4.

[0179] [R 91 〕 In formula 2D, R 91 R each independently represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group. 91 is preferably a hydrogen atom or a hydrocarbon group, more preferably an alkyl group, even more preferably an alkyl group having 1 to 4 carbon atoms, and particularly preferably a methyl group or an ethyl group.

[0180] [R 92 〕 In formula 2D, R 92 R each independently represents a hydrocarbon group or a heterocyclic group. 92 is preferably a hydrocarbon group, more preferably an alkyl group, and even more preferably an alkyl group having 1 to 20 carbon atoms.

[0181] (Group represented by formula 2E) Ar 1 and Ar 2 are each preferably independently a group represented by formula 2E. The group represented by formula 2E is one embodiment of the group represented by formula 2B.

[0182] [ka]

[0183] [X 1 〕 In formula 2E, X 1 represents a halogen atom. 1 is preferably a fluorine atom or a chlorine atom, more preferably a chlorine atom.

[0184] [R 20 〕 R 20 represents a hydrocarbon group or an aromatic heterocyclic group. 20 is preferably a hydrocarbon group, more preferably an aliphatic hydrocarbon, and further preferably an alkyl group having 1 to 4 carbon atoms.

[0185] [n11] n11 is an integer of 1 to 4.

[0186] (Group represented by formula 2F) Ar 1 and Ar 2 are each preferably independently a group represented by formula 2F. The group represented by formula 2F is one embodiment of the group represented by formula 2B.

[0187] [ka]

[0188] [X 2 〕 In formula 2F, X 2 represents a halogen atom. 2 is preferably a fluorine atom or a chlorine atom, more preferably a chlorine atom.

[0189] [R 21 〕 R 21 represents a hydrocarbon group or an aromatic heterocyclic group. 21 is preferably a hydrocarbon group, more preferably an aliphatic hydrocarbon, and further preferably an alkyl group having 1 to 4 carbon atoms.

[0190] [n12] n12 is an integer of 1 to 4.

[0191] (Group represented by formula 3) In one embodiment, Ar 1 and Ar 2 are each independently a group represented by formula 3.

[0192] [ka]

[0193] [R 13 〕 In formula 3, R 13 is an unsubstituted hydrocarbon group or aromatic heterocyclic group, or a hydrocarbon group or aromatic heterocyclic group having at least one substituent selected from the group consisting of a halogen atom, an aliphatic hydrocarbon group, an alkoxy group, an amino group, and the above-mentioned Group A.

[0194] R 13The hydrocarbon group represented by the formula (I) may be any of an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. The unsubstituted hydrocarbon group may also be a combination of an unsubstituted aliphatic hydrocarbon group, an unsubstituted alicyclic hydrocarbon group, and an unsubstituted aromatic hydrocarbon group. Examples of the combination include a group in which at least one unsubstituted aliphatic hydrocarbon group and at least one unsubstituted aromatic hydrocarbon group are linked to each other. Specific examples of combinations of an unsubstituted aliphatic hydrocarbon group and an unsubstituted aromatic hydrocarbon group include a benzyl group, a methylbenzyl group, a vinylbenzyl group, a biphenylmethyl group, and a methylbiphenylmethyl group.

[0195] Specific examples of the aliphatic hydrocarbon group include R 1 and R 2 Specific examples of the aliphatic hydrocarbon group include those represented by the following formula:

[0196] Specific examples of the aromatic hydrocarbon group include the specific examples of the aromatic hydrocarbon group for the substituent T above.

[0197] Specific examples of the alicyclic hydrocarbon group include the specific examples of the alicyclic hydrocarbon group for the substituent T described above.

[0198] R 13 Specific examples of the aromatic heterocyclic group represented by the formula: Ar 1 and Ar 2 Specific examples of the aromatic heterocyclic group are:

[0199] Among them, R 13 is preferably an aliphatic hydrocarbon group, more preferably an alkyl group having 1 to 18 carbon atoms, and even more preferably an alkyl group having 1 to 10 carbon atoms.

[0200] [R 14 〕 In formula 3, R 14 is a group selected from the group consisting of a halogen atom, a hydroxy group, an aliphatic hydrocarbon group, and the above-mentioned Group A. 14is preferably an aliphatic hydrocarbon group, more preferably an alkyl group having 1 to 4 carbon atoms.

[0201] [L 1 〕 In formula 3, L 1 is an oxygen atom or NR 15 Represents R 15 represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group.

[0202] L 1 is preferably an oxygen atom. 1 -R 13 is preferably an alkoxy group, more preferably a methoxy group or an ethoxy group.

[0203] R 15 Specific examples of hydrocarbon groups represented by R 13 Specific examples of hydrocarbon groups include those represented by the following formula:

[0204] R 15 Specific examples of the heterocyclic group represented by the following formula include the specific examples of the heterocyclic group for the substituent T above.

[0205] [n4, n5] In formula 3, n4 is an integer of 1 to 5. n5 is an integer of 0 to 4. n4+n5 is an integer of 1 to 5. When n4 is 1, L 1 -R 13 is located at the ortho position, or n5 is an integer of 1 or more.

[0206] (Group represented by formula 3A) Ar 1 and Ar 2 are each independently preferably a group represented by formula 3A. The group represented by formula 3A is one embodiment of the group represented by formula 3.

[0207] [ka]

[0208] [R14 〕 In formula 3A, R 14 is R in Equation 3 14 is synonymous with.

[0209] [R 22 〕 In formula 3A, R 22 is an unsubstituted hydrocarbon group or aromatic heterocyclic group, or a hydrocarbon group or aromatic heterocyclic group having at least one substituent selected from Group A above.

[0210] R 22 Specific examples of hydrocarbon groups represented by R 13 Specific examples of hydrocarbon groups include those represented by the following formula:

[0211] R 22 is preferably an aliphatic hydrocarbon group, more preferably an alkyl group having 1 to 4 carbon atoms.

[0212] [n13] In formula 3A, n13 is an integer of 0 to 4.

[0213] (Group represented by formula 3B) Ar 1 and Ar 2 are each independently preferably a group represented by formula 3B. The group represented by formula 3B is one embodiment of the group represented by formula 3.

[0214] [ka]

[0215] [R 14 〕 In formula 3B, R 14 is R in Equation 3 14 is synonymous with.

[0216] [R 23 〕 In formula 3B, R 23is an unsubstituted hydrocarbon group or aromatic heterocyclic group, or a hydrocarbon group or aromatic heterocyclic group having at least one substituent selected from Group A.

[0217] R 23 Specific examples of hydrocarbon groups represented by R 13 Specific examples of hydrocarbon groups include those represented by the following formula:

[0218] R 23 is preferably an aliphatic hydrocarbon group, more preferably an alkyl group having 1 to 4 carbon atoms.

[0219] [n14] In formula 3B, n14 is an integer of 1 to 4.

[0220] Preferred specific examples of the compound of the present disclosure are shown below. Note that the compound of the present disclosure is not limited to the following specific examples. In the specific examples, "Me" represents a methyl group, and "Et" represents an ethyl group.

[0221] [ka]

[0222] [ka]

[0223] [ka]

[0224] [ka]

[0225] [ka] JPEG0007719183000028.jpg168156

[0226] [ka]

[0227] [ka]

[0228] [ka]

[0229] The compounds of the present disclosure can be produced, for example, by the following method.

[0230] [ka]

[0231] In Formula 5a, Formula 5d, Formula 5f, and Formula 5g, Ar a is Ar in Eq. 1 and Ar 2 is equivalent to In formula 5b, formula 5c, formula 5d, formula 5f, and formula 5g, R a is R in Equation 1 1 and R 2 is equivalent to In Formula 5e, Formula 5f, and Formula 5g, R b is R in Equation 1 3 ~R 8 is equivalent to X in Equation 5c a , and X in Equation 5e b represents a leaving group. Examples of the leaving group include a halogen atom.

[0232] [Pigment] The compounds of the present disclosure can be used as dyes.

[0233] [Thermal transfer recording ink sheet] The thermal transfer recording ink sheet of the present disclosure contains a compound represented by Formula 1 above. Thermal transfer recording ink sheets generally include a support and a dye-donor layer formed on the support. The compound represented by Formula 1 above can be contained in the dye-donor layer. The dye-donor layer can be formed by dissolving the compound represented by Formula 1 above together with a binder resin in a solvent, or by dispersing the compound represented by Formula 1 above in a solvent to prepare an ink, applying the ink to a support, and appropriately drying it. The thermal transfer recording ink sheet of the present disclosure may also contain a dye compound other than the compound represented by Formula 1 above.

[0234] (Support) The support for the thermal transfer recording ink sheet can be any conventionally known support for ink sheets. For example, the materials described in paragraph 0050 of JP-A-7-137466 are preferably used as the support. The thickness of the support is preferably 2 μm to 30 μm.

[0235] (Dye-donating layer) The dye-donating layer preferably contains a binder resin and a solvent. As the binder resin, conventionally known resins and solvents can be used.

[0236] The content of the compound represented by formula 1 in the dye-donating layer was 0.03 g / m 2 ~1.0g / m 2 is preferred, and 0.1 g / m 2 ~0.6g / m 2 The thickness of the dye-donating layer is preferably from 0.2 μm to 5 μm, and more preferably from 0.4 μm to 2 μm.

[0237] The thermal transfer recording ink sheet of the present disclosure may have layers other than the dye-donating layer, such as an intermediate layer between the support and the dye-donating layer, or a backing layer on the support opposite to the dye-donating layer. [Example]

[0238] The present disclosure will be described in detail below with reference to examples, but the present disclosure is not limited to the following examples.

[0239] <Synthesis of Compound D-1> Compound D-1 was synthesized according to the following scheme.

[0240] [ka]

[0241] (Synthesis of intermediate D-1c) 1.00 parts of 2-amino-3-methylpyridine (manufactured by Tokyo Chemical Industry Co., Ltd., "D-1a"), 2.96 parts of 7-(bromomethyl)pentadecane (manufactured by Tokyo Chemical Industry Co., Ltd., "D-1b"), 1.27 parts of potassium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), and 10.0 parts of dimethylformamide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed and stirred at 80°C for 6 hours. After completion of the reaction, 10 parts of hexane, 10 parts of ethyl acetate, and 10 parts of brine were added, and the aqueous layer was discarded. The organic layer was washed with brine, and the solvent was then distilled off. The residue was purified by silica gel chromatography (hexane / ethyl acetate = 10 / 1). The resulting oil was dried under reduced pressure at 40°C for 6 hours to obtain 1.01 parts of intermediate D-1c.

[0242] (Synthesis of intermediate D-1e) 1.00 parts of Intermediate D-1c, 0.52 parts of 3-bromophenol (Tokyo Chemical Industry Co., Ltd., "D-1d"), 0.03 parts of palladium acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 0.75 parts of sodium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), 2.42 parts of a 1 mol / L tri-t-butylphosphine hexane solution (Fujifilm Wako Pure Chemical Industries, Ltd.), and 10.0 parts of toluene were mixed and stirred at 100°C for 6 hours. After the reaction was complete, 30 parts of ethyl acetate and 30 parts of water were added, the aqueous layer was discarded, the organic layer was washed with water, and the solvent was distilled off. The residue was purified by silica gel chromatography (hexane / ethyl acetate = 10 / 1). The resulting oil was dried under reduced pressure at 60°C for 24 hours to obtain 0.84 parts of Intermediate D-1e.

[0243] (Synthesis of Compound D-1) 0.80 parts of intermediate D-1e, 0.11 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione (Tokyo Chemical Industry Co., Ltd., "D-1f"), 5.0 parts of 1-butanol, and 5.0 parts of toluene were mixed. The resulting mixture was stirred at 120°C for 3 hours using a Dean-Stark tube while removing the generated water. After the reaction was completed, the solvent was distilled off, and 30.0 parts of ethyl acetate was added. The organic layer was washed with aqueous sodium bicarbonate, and the solvent was distilled off. The residue was purified by silica gel chromatography (hexane / ethyl acetate = 10 / 1). The resulting solid was dried under reduced pressure at 40°C for 6 hours, yielding 0.37 parts of compound D-1.

[0244] The mass-to-charge ratio (ie, m / z) in the mass spectrum of compound D-1 is shown below. MS(m / z)=927.7([M+1] + )

[0245] <Synthesis of Compound D-2> Compound D-2 was synthesized according to the following scheme.

[0246] [ka]

[0247] (Synthesis of intermediate D-2b) 1.00 parts of 2-amino-3-methylpyridine (manufactured by Tokyo Chemical Industry Co., Ltd., "D-1a"), 1.13 parts of 2-ethylhexanal (manufactured by Tokyo Chemical Industry Co., Ltd., "D-2a"), 1.59 parts of acetic acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 10.0 parts of dichloromethane (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed and stirred at 5°C for 10 minutes. Subsequently, 2.80 parts of sodium triacetoxyborohydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the mixture was returned to room temperature and stirred for 1 hour. After completion of the reaction, dichloromethane and saturated aqueous sodium bicarbonate solution were added, and the aqueous layer was discarded. The organic layer was washed with brine, and the solvent was distilled off. The residue was purified by silica gel chromatography (hexane / ethyl acetate = 10 / 1). The resulting oil was dried under reduced pressure at 40°C for 6 hours to obtain 1.69 parts of intermediate D-2b.

[0248] (Synthesis of intermediate D-2c) Intermediate D-2c was synthesized according to the synthetic method for intermediate D-1e, except that intermediate D-2b was used instead of intermediate D-1c.

[0249] (Synthesis of Compound D-2) Compound D-2 was synthesized (yield 70%) according to the synthesis method of compound D-1, except that intermediate D-2c was used instead of intermediate D-1e.

[0250] The mass-to-charge ratio (ie, m / z) in the mass spectrum of compound D-2 is shown below. MS(m / z)=703.4([M+1] + )

[0251] <Synthesis of Compound D-3> Compound D-3 was synthesized in accordance with the synthesis method for compound D-2, except that 4-chloro-2-methylaniline (Tokyo Chemical Industry Co., Ltd.) was used instead of intermediate D-1a (yield of the final step: 75%).

[0252] [ka]

[0253] The mass-to-charge ratio (ie, m / z) in the mass spectrum of compound D-3 is shown below. MS(m / z)=769.4([M+1] + )

[0254] <Synthesis of Compound D-8> (Synthesis of intermediate D-8a) 1.00 parts of 2,4,6-trimethyl-1,3-phenylenediamine (Tokyo Chemical Industry Co., Ltd.) and 40.0 parts of ethyl acetate (Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed, and 0.52 parts of acetyl chloride (Tokyo Chemical Industry Co., Ltd.) and 0.81 parts of N,N-dimethylaniline were added dropwise in this order, followed by stirring at room temperature for 3 hours. After completion of the reaction, ethyl acetate and saturated aqueous sodium bicarbonate solution were added, and the aqueous layer was discarded. The organic layer was washed with brine, and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain 0.5 parts of intermediate D-8a.

[0255] [ka]

[0256] (Synthesis of Compound D-8) Compound D-8 was synthesized in accordance with the synthesis method for compound D-2, except that intermediate D-8a was used instead of intermediate D-1a (yield of the final step: 31%).

[0257] [ka]

[0258] The mass-to-charge ratio (ie, m / z) in the mass spectrum of compound D-8 is shown below. MS(m / z)=871.5([M+1] + )

[0259] <Synthesis of Compound D-10> Compound D-10 was synthesized according to the following scheme.

[0260] [ka]

[0261] (Synthesis of intermediate D-10c) 1.00 parts of 1-chloro-2,4-dinitrobenzene (Tokyo Chemical Industry Co., Ltd., "D-10a"), 0.61 parts of 3-(methylamino)phenol (Fujifilm Wako Pure Chemical Industries, Ltd., "D-10b"), and 10 parts of N-methylpyrrolidone (Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed and stirred at 130°C for 2 hours. After the reaction was completed, the mixture was returned to room temperature, ethyl acetate and 0.2 mol / L aqueous hydrochloric acid were added, and the aqueous layer was discarded. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, and the solvent was then distilled off. The residue was dispersed and washed with a mixed solvent of hexane / dichloromethane (mass ratio = 1 / 1) and then filtered. The resulting solid was dried to obtain 0.80 parts of intermediate D-10c.

[0262] (Synthesis of Intermediate D-10e) 1.00 parts of intermediate D-10c, 0.50 parts of palladium / carbon (Pd: 5% by mass), and 50.0 parts of ethyl acetate (Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed and heated in a pressure-resistant vessel under a hydrogen atmosphere at 50°C for 4 hours. After replacing with nitrogen, the vessel was opened and 1.50 parts of isobutyraldehyde (Tokyo Chemical Industry Co., Ltd., "D-10d") was added. The vessel was again reacted under a hydrogen atmosphere at 50°C for 4 hours. After the reaction was completed, the mixture was returned to room temperature, filtered through Celite, and concentrated. The residue was purified by silica gel chromatography to obtain 0.67 parts of intermediate D-10e.

[0263] (Synthesis of Intermediate D-10g) 1.00 parts of intermediate D-10e and 40.0 parts of ethyl acetate (Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed, and 0.87 parts of isovaleryl chloride (Tokyo Chemical Industry Co., Ltd., "D-10f") and 1.80 parts of N,N-dimethylaniline (Tokyo Chemical Industry Co., Ltd.) were added dropwise in this order, followed by stirring at room temperature for 5 hours. After completion of the reaction, ethyl acetate and saturated aqueous sodium bicarbonate solution were added, and the aqueous layer was discarded. The organic layer was washed with brine, and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain 1.4 parts of intermediate D-10g.

[0264] (Synthesis of Compound D-10) 1.00 parts of intermediate D-10g, 0.17 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione (Tokyo Chemical Industry Co., Ltd., "D-1f"), 5.0 parts of 1-butanol, and 5.0 parts of toluene were mixed. The resulting mixture was stirred at 120°C for 6 hours while removing the generated water using a Dean-Stark tube. After the reaction was completed, the solvent was distilled off, 30.0 parts of ethyl acetate was added, and the organic layer was washed with aqueous sodium bicarbonate and the solvent was distilled off. The residue was purified by silica gel chromatography. The resulting solid was dried to obtain 0.68 parts of compound D-10 (yield 60%).

[0265] The mass-to-charge ratio (ie, m / z) in the mass spectrum of compound D-10 is shown below. MS(m / z)=1098.7([M+1] + )

[0266] <Synthesis of Compound D-11> Compound D-11 was synthesized according to the following scheme.

[0267] [ka]

[0268] (Synthesis of intermediate D-11c) 1.00 parts of 2-aminophenyl phenyl sulfone (Tokyo Chemical Industry Co., Ltd., "D-11a"), 0.80 parts of 3-bromoanisole (Tokyo Chemical Industry Co., Ltd., "D-11b"), 0.03 parts of palladium acetate (Fujifilm Wako Pure Chemical Industries, Ltd.), 0.75 parts of sodium tert-butoxide (Tokyo Chemical Industry Co., Ltd.), 2.42 parts of 1 mol / L tri-t-butylphosphine hexane solution (Fujifilm Wako Pure Chemical Industries, Ltd.), and 10.0 parts of toluene were mixed and stirred at 110°C for 5 hours. After the reaction was complete, 30 parts of ethyl acetate and 30 parts of water were added, and the aqueous layer was discarded. The organic layer was washed with water and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain 0.79 parts of intermediate D-11c.

[0269] (Synthesis of intermediate D-11e) 1.00 parts of intermediate D-11c, 0.57 parts of 1-bromo-2-ethylhexane (Tokyo Chemical Industry Co., Ltd., "D-11d"), and 10.0 parts of dimethyl sulfoxide (Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed and stirred at room temperature for 8 hours. After the reaction was completed, 30 parts of ethyl acetate and 30 parts of water were added, the aqueous layer was discarded, the organic layer was washed with water, and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain 1.05 parts of intermediate D-11e.

[0270] (Synthesis of intermediate D-11f) 1.00 parts of intermediate D-11e was mixed with 50 parts of methylene chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and cooled to 0°C. 3.00 parts of a 1 mol / L solution of boron tribromide in dichloromethane (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added dropwise with stirring, and the mixture was then heated to 10°C and stirred for 5 hours. After completion of the reaction, dichloromethane and water were added, the aqueous layer was discarded, the organic layer was washed with water, and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain 0.56 parts of intermediate D-11f.

[0271] (Synthesis of Compound D-11) Compound D-11 was synthesized (yield: 43%) according to the synthesis method of compound D-1, except that intermediate D-11f was used instead of intermediate D-1e.

[0272] The mass-to-charge ratio (ie, m / z) in the mass spectrum of compound D-11 is shown below. MS(m / z)=953.4([M+1] + )

[0273] <Synthesis of Compound D-13> Compound D-13 was synthesized (yield of the final step: 23%) according to the synthesis method of compound D-2, except that 2-methoxyaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 2-amino-3-methylpyridine (manufactured by Tokyo Chemical Industry Co., Ltd., "D-1a").

[0274] [ka]

[0275] The mass-to-charge ratio (ie, m / z) in the mass spectrum of compound D-13 is shown below. MS(m / z)=733.4([M+1] + )

[0276] <Synthesis of Compound D-14> Compound D-14 was synthesized (yield of the final step: 82%) according to the synthesis method of compound D-2, except that 4-methoxy-2-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 2-amino-3-methylpyridine (manufactured by Tokyo Chemical Industry Co., Ltd., "D-1a").

[0277] [ka]

[0278] The mass-to-charge ratio (ie, m / z) in the mass spectrum of compound D-14 is shown below. MS(m / z)=761.5([M+1] + )

[0279] <Synthesis of Compound D-49> Compound D-49 was synthesized according to the following scheme.

[0280] [ka]

[0281] (Synthesis of intermediate D-49c) A three-neck flask was charged with 161.0 g of 2-aminophenol ("D-49a"), 174.0 g of sodium bicarbonate, and 640 mL of N,N-dimethylacetamide. While heating, 398 g of 1-bromo-2-ethylhexane ("D-49b") was added dropwise at an internal temperature of 48-52°C. After the addition was complete, the mixture was heated and stirred at an internal temperature of 62-70°C for 5.5 hours. Then, the mixture was allowed to cool to 30°C. 1 L of ethyl acetate, 1 L of water, and 30 g of activated carbon were added. The mixture was stirred for 10 minutes and then allowed to stand for 12 hours. The insoluble matter was removed by filtration through Celite, and the resulting solution was separated. The resulting ethyl acetate layer was washed five times with a mixture of 200 mL of saturated brine and 800 mL of water, dried over anhydrous sodium sulfate, and concentrated using a rotary evaporator. The resulting residue was purified by silica gel column chromatography to obtain 270.1 g of intermediate D-49c (yield: 82%).

[0282] (Synthesis of intermediate D-49d) A three-neck flask was charged with 250 mL of methylene chloride, 103.8 g of 3-bromophenol, and 1.9 g of p-toluenesulfonic acid monohydrate. While stirring the three-neck flask at room temperature, 250 mL of dihydropyran was added dropwise over 1 hour. After the addition was complete, the mixture was stirred at room temperature for an additional 3 hours. The reaction mixture was then added to 84 g of sodium bicarbonate and stirred, and the insoluble material was filtered off. The resulting solution was concentrated using a rotary evaporator to obtain 154.4 g of intermediate D-49d (yield: approximately 100%).

[0283] (Synthesis of Intermediate D-49e) The three-neck flask was purged with nitrogen by repeatedly supplying nitrogen and reducing the pressure four times. 1.37 g of palladium(II) acetate and 250 mL of toluene were placed in the three-neck flask at room temperature. While stirring the three-neck flask, 26.8 mL of a hexane solution of tri-t-butylphosphine (1 mol / L) was added and stirred for 30 minutes. Next, a solution of 135 g of intermediate D-49c dissolved in 200 mL of toluene was added dropwise over 10 minutes. 152 g of sodium tert-butoxide was added and washed in with 100 mL of toluene. 157 g of intermediate D-49d was added dropwise, followed by washing in with 200 mL of toluene. The mixture was then heated to reflux and stirred for 5 hours. The reaction mixture was cooled to 40 °C and extracted with 500 mL of ethyl acetate and 500 mL of water. The resulting organic layer was washed four times with a mixture of 100 mL of saturated brine and 500 mL of water, dried over anhydrous sodium sulfate, and concentrated using a rotary evaporator. The resulting residue was purified by silica gel column chromatography to obtain 223 g of intermediate D-49e (yield 92%).

[0284] (Synthesis of intermediate D-49f) A three-neck flask was charged with 198.8 g of D-49e, 138.2 g of potassium carbonate, and 600 mL of N,N-dimethylacetamide. While heating and stirring at an internal temperature of 85°C, 154.5 g of 1-bromo-2-ethylhexane ("D-49b") was added dropwise. After the addition was complete, the mixture was heated and stirred for 3 hours. The mixture was then cooled to 40°C, and 1.2 L of ethyl acetate and 1.2 L of water were added for extraction. The resulting ethyl acetate layer was washed five times with a mixed aqueous solution of 150 mL of saturated brine and 750 mL of water, dried over anhydrous sodium sulfate, and concentrated using a rotary evaporator. The resulting residue was purified by silica gel column chromatography to obtain 237.0 g of intermediate D-49f (yield: 93%).

[0285] (Synthesis of Intermediate D-49g) A three-neck flask was charged with 700 mL of ethanol and 0.95 g of p-toluenesulfonic acid monohydrate. While stirring at room temperature, a solution of 152.9 g of D-49f dissolved in toluene was added dropwise. During the dropwise addition, the internal temperature rose to 45°C. After stirring for 2 hours, the reaction mixture was poured into 42 g of sodium bicarbonate and stirred. Insoluble matter was filtered off, and the resulting solution was concentrated using a rotary evaporator. The residue after concentration was purified by silica gel column chromatography to obtain 125.1 g of intermediate D-49g (yield 98%).

[0286] (Synthesis of Compound D-49) In a recovery flask equipped with a Dean-Stark water separator, 42.6 g of D-49g, 6.3 g of 3,4-dihydroxy-3-cyclobutene-1,2-dione (Tokyo Chemical Industry Co., Ltd., "D-1f"), 700 mL of butanol, and 700 mL of toluene were placed, and the mixture was heated and stirred under reflux at an external temperature of 135°C for 1 hour. The mixture was concentrated using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography to obtain 41.4 g of compound D-49 (yield 89%).

[0287] [ka]

[0288] The mass-to-charge ratio (ie, m / z) in the mass spectrum of compound D-49 is shown below. MS(m / z)=929.6([M+1] + )

[0289] <Compound H-1>

[0290] [ka]

[0291] <Compound H-2>

[0292] [ka]

[0293] <Compound H-3>

[0294] [ka]

[0295] <Compound H-4>

[0296] [ka]

[0297] <Compound H-5>

[0298] [ka]

[0299] <Preparation of Ink Sheet for Thermal Transfer Recording> A 6.0 μm-thick polyester film (trade name "Lumirror," manufactured by Toray Industries, Inc.) was prepared as a support, with the back surface treated with a heat-resistant, lubricating thermosetting acrylic resin (thickness 1 μm). A dye-donor layer-forming coating composition having the following composition was applied to the front surface of the film with a wire bar to a dry thickness of 1 μm, thereby producing a thermal transfer recording ink sheet.

[0300] (Coating composition for forming dye-donor layer) Compounds listed in Table 1...5 parts by mass Polyvinyl butyral resin (product name "S-LEC BX-1", manufactured by Sekisui Chemical Co., Ltd.) ... 4.5 parts by mass Methyl ethyl ketone / toluene mixed solution (mass ratio = 1 / 1) ... 90 parts by mass

[0301] The prepared thermal transfer recording ink sheets were evaluated for wet heat resistance, solubility, and light resistance.

[0302] <Moisture and heat resistance> The prepared thermal transfer recording ink sheet and an image-receiving sheet for ASK2000 (manufactured by Fujifilm Corporation) were superimposed so that the dye-donating layer of the thermal transfer recording ink sheet and the image-receiving layer of the image-receiving sheet were in contact. Printing was performed using a thermal head from the back side of the dye-donating layer under conditions of a thermal head output of 0.25 W / dot, a pulse width of 0.15 to 15 ms, and a dot density of 6 dots / mm, obtaining thermal transfer recorded image A. The prepared thermal transfer recording ink sheet was then wound into a roll and allowed to stand for 24 hours under conditions of a temperature of 60°C and a relative humidity of 70%. After 24 hours, thermal transfer recorded image B was obtained in the same manner as above. Thermal transfer recorded image A and thermal transfer recorded image B were visually compared, and their humidity and heat resistance was evaluated based on the degree of change in reflection density. The evaluation criteria are as follows: A: Almost no change in reflection density is observed. B: Reflection density changed slightly. C: The reflection density changed, but to a level that does not pose a problem in practical use. D: The reflection density changed significantly.

[0303] <Solubility> Each compound was added to a methyl ethyl ketone / toluene mixed solution (mass ratio = 1 / 1) so that the content of each compound was 5.3 mass %, and the solubility was evaluated. The evaluation criteria are as follows. A: It dissolved immediately. B: Dissolved after stirring. C: Dissolved by stirring while heating. D: Even when heated and stirred, some of the material remained undissolved.

[0304] <Light resistance> The prepared thermal transfer recording ink sheet and an image-receiving sheet for ASK2000 (manufactured by Fujifilm Corporation) were superimposed so that the dye-donating layer of the thermal transfer recording ink sheet was in contact with the image-receiving layer of the image-receiving sheet. Printing was performed using a thermal head from the back side of the dye-donating layer under conditions of thermal head output of 0.25 W / dot, pulse width of 0.15 ms to 15 ms, and dot density of 6 dots / mm, resulting in an image-wise dyeing of the cyan dye onto the image-receiving layer of the image-receiving sheet. A clear thermal transfer recording image without transfer unevenness was obtained.

[0305] Next, each of the obtained recorded image-receiving sheets was irradiated with a Xe light (100,000 lux) for 12 hours. The reflection density after irradiation was measured for the area where the reflection density was 1.0 before irradiation. The ratio (percentage) of the reflection density after irradiation to the reflection density of 1.0 before irradiation was calculated as the residual rate. The evaluation criteria were as follows: A: The survival rate was between 95% and 100%. B: The survival rate was 90% or more but less than 95%. C: The survival rate was 85% or more but less than 90%. D: The residual rate was 80% or more but less than 85%. E: The survival rate was less than 80%.

[0306] [Table 1]

[0307] As shown in Table 1, it was found that the thermal transfer recording ink sheets of Examples 1 to 9 contain the compound represented by Formula 1 and therefore have excellent wet heat resistance.

[0308] On the other hand, the thermal transfer recording ink sheets of Comparative Examples 1 to 5 did not contain the compound represented by formula 1, and therefore were found to be inferior in moist heat resistance.

[0309] Furthermore, the compound represented by formula 1 can be used as a cyan dye, and it was found that the compound had excellent lightfastness in a green image obtained by mixing it with the yellow dye Y-1 below.

[0310] [ka]

[0311] The disclosure of Japanese Patent Application No. 2021-111741, filed on July 5, 2021, is incorporated herein by reference in its entirety. In addition, all documents, patent applications, and technical standards described herein are incorporated herein by reference to the same extent as if each individual document, patent application, and technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. A compound represented by the following formula 1: 【Chemical 1】 In formula 1, R １ and R ２ each independently represents an unsubstituted aliphatic hydrocarbon group, R ３ ~R ８ each independently represents a hydrogen atom, Ar １ and Ar ２ are each independently a group represented by any one of the following formulas 2A, 2B, 3, and 4, and Ar 1 and Ar 2 have a substituent at the ortho position of the ring bonded to the nitrogen atom. 【Chemistry 2】 In formula 2A, R 16 represents R 10 , R 11 or R 12 ; R １０ each independently represents a halogen atom or a halogenated alkyl group, R １１ each independently represents an aromatic hydrocarbon group, a heterocyclic group, a cyano group, a silyl group, a nitro group, an imido group, or —COR ５１ , -COOR ５２ , -CONR ５３ R ５４ , -NR ５５ COR ５６ , -NR ５７ COOR ５８ , -NR ５９ CONR ６０ R ６１ , -NR ６２ SO ２ R ６３ , -NR ６４ SO ２ NR ６５ R ６６ , -OCOR ６７ , -OCONR ６８ R ６９ , -SR ７０ , -SOR ７１ , -SO ２ R ７２ , -SO ２ OR ７３ , -SO ２ NR ７４ R ７５ ,-CSR ７６ , -N=N-R ７７ , -POR ７８ R ７９ , -OPOR ８０ R ８１ , -PR ８２ R ８３ , and -OPR ８４ R ８５ is a group selected from Group A consisting of R ５１ ~R ７７ each independently represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; R ７８ ~R ８５ each independently represents a hydroxy group, an alkoxy group, an aryloxy group, or a hydrocarbon group; R １２ represents an unsubstituted aliphatic hydrocarbon group or an aliphatic hydrocarbon group having at least one substituent selected from the group consisting of a hydroxy group, an alkoxy group, an amino group, and Group A; at least one of R 16 is —COR 51 , —COOR 52 , —CONR 53 R 54 , —NR 55 COR 56 , —NR 59 CONR 60 R 61 , —NR 62 SO 2 R 63 , or —SO 2 R 72 ; n6 is an integer from 1 to 5, In formula 2B, R 10 and R 12 have the same meanings as R 10 and R 12 in formula 2A above, respectively; n7 and n8 each independently represent an integer of 1 to 4, n7+n8 is an integer from 2 to 5, In formula 3, R １３ represents an unsubstituted hydrocarbon group or aromatic heterocyclic group, or a hydrocarbon group or aromatic heterocyclic group having at least one substituent selected from the group consisting of a halogen atom, an aliphatic hydrocarbon group, an alkoxy group, an amino group, and the above-mentioned Group A, R １４ is a group selected from the group consisting of a halogen atom, a hydroxy group, an aliphatic hydrocarbon group, and Group A; L １ is an oxygen atom or NR １５ represents R １５ represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; n4 is an integer from 1 to 5, n5 is an integer from 0 to 4, n4+n5 is an integer from 1 to 5, If n4 is 1, L １ -R １３ is located at the ortho position, or n5 is an integer of 1 or more, In formula 4, A 1 , A 2 , A 3 , A 4 and A 5 each represent a nitrogen atom or CR 17 ; at least one of A 1 , A 2 , A 3 , A 4 and A 5 is a nitrogen atom; R 17 represents a hydrogen atom or a substituent, and a plurality of R 17 s may be bonded to each other to form a ring; In Formula 2A, Formula 2B, Formula 3 and Formula 4, * indicates the bonding site with the nitrogen atom.

2. The Ar １ and the Ar ２ are each independently a group selected from the group consisting of groups represented by the following formulas 2C to 2F, 3A, 3B, and 4A: 【Chemistry 3】 In formula 2C, R １８ is R in the formula 2A １０ , R １１ , or R １２ represents n9 is an integer from 0 to 4, In formula 2D, R １９ is R in the formula 2A １０ , R １１ , or R １２ represents n10 is an integer from 1 to 4, In formula 2E, X １ represents a halogen atom, R ２０ represents a hydrocarbon group or an aromatic heterocyclic group, n11 is an integer from 1 to 4, In formula 2F, X ２ represents a halogen atom, R ２１ represents a hydrocarbon group or an aromatic heterocyclic group, n12 is an integer from 1 to 4, In formula 3A, R １４ is R in the formula 3 １４ is synonymous with R ２２ represents an unsubstituted hydrocarbon group or an aromatic heterocyclic group, or a hydrocarbon group or an aromatic heterocyclic group having at least one substituent selected from Group A, n13 is an integer from 0 to 4, In formula 3B, R １４ is R in the formula 3 １４ is synonymous with R ２３ represents an unsubstituted hydrocarbon group or an aromatic heterocyclic group, or a hydrocarbon group or an aromatic heterocyclic group having at least one substituent selected from Group A, n14 is an integer from 1 to 4, In formula 4A, R １７ are each independently R in formula 4 １７ is synonymous with n15 is an integer from 0 to 3, In Formula 2C and Formula 2D, R ９１ each independently represents a hydrogen atom, a hydrocarbon group, or a heterocyclic group; R ９２ each independently represents a hydrocarbon group or a heterocyclic group, In Formulae 2C to 2F, 3A, 3B, and 4A, * indicates the bonding site with the nitrogen atom.

3. A dye comprising the compound according to claim 1 or 2.

4. 3. An ink sheet for thermal transfer recording, comprising the compound according to claim 1 or 2.

Images