Composition, film, optical filter, solid-state imaging element, image display device, infrared sensor, camera module, compound, and compound manufacturing method
The composition with a pigment, compound (1), and resin enhances dispersibility and moisture resistance, addressing issues in existing pigment-based compositions for optical filters and films.
Patent Information
- Application Number
- PCT/JP2025/027286
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2025-07-02
- Filing Date
- 2025-08-01
- Publication Date
- 2026-02-19
AI Technical Summary
Existing compositions using pigments as coloring materials face challenges in dispersibility, storage stability, and moisture resistance, particularly in the formation of optical filters and films.
A composition containing a pigment, a compound represented by formula (1) with a dye skeleton, a resin having an amine value, and a solvent, which forms a network structure to enhance dispersibility and moisture resistance through acid-base interactions and steric hindrance.
The composition achieves improved dispersibility and storage stability, forming films with excellent moisture resistance, suitable for optical filters and other devices.
Smart Images

Figure JP2025027286_19022026_PF_FP_ABST
Abstract
Description
Composition, film, optical filter, solid-state imaging device, image display device, infrared sensor, camera module, compound, and method for producing compound
[0001] The present invention relates to a composition containing a colorant. The present invention also relates to a film, an optical filter, a solid-state imaging device, an image display device, an infrared sensor, and a camera module using the composition. The present invention also relates to a compound and a method for producing the compound.
[0002] BACKGROUND ART Optical filters such as color filters, infrared transmission filters, and infrared cut filters are produced using compositions containing coloring materials.
[0003] When a pigment is used as a coloring material, the use of a pigment derivative together with the pigment has been investigated in order to improve the dispersibility of the pigment in the composition (see, for example, Patent Document 1).
[0004] International Publication No. 2018 / 101189
[0005] There is a demand for further improvements in dispersibility and storage stability of compositions using pigments as coloring materials, as well as for further improvements in the moisture resistance of films obtained using the compositions.
[0006] Therefore, an object of the present invention is to provide a composition that has good dispersibility and storage stability and is capable of forming a film having excellent moisture resistance. Another object of the present invention is to provide a film, an optical filter, a solid-state imaging device, an image display device, an infrared sensor, a camera module, a compound, and a method for producing the compound.
[0007] The present invention provides the following:
[0008] <1> A composition including a colorant containing a pigment, a compound represented by formula (1), a resin having an amine value, and a solvent; In formula (1), A 1 represents a dye skeleton derived from a dye compound, and L 1 represents a single bond or a divalent linking group; 2 and L 3 each independently represents a single bond or an alkylene group having 1 to 30 carbon atoms; R 1represents a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 2 represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent; R 1 and R 2 may be bonded to form a ring, X 1 represents an acid group or a salt thereof, and p represents an integer of 1 to 20. <2> A in the above formula (1) 1 is a dye skeleton derived from a dye compound selected from a pyrrolopyrrole dye compound, a phthalocyanine dye compound, a squarylium dye compound, an indigo dye compound, a croconium dye compound, an isoindoline dye compound, a quinophthalone dye compound, a diketopyrrolopyrrole dye compound, a triarylmethane dye compound, a xanthene dye compound, a pyrromethene dye compound, a perylene dye compound, an azomethine dye compound, an anthraquinone dye compound, a quinacridone dye compound, a dioxazine dye compound, and a benzofuranone dye compound. 1 <4> The composition according to <1> or <2>, wherein R in the formula (1) is an alkyl group having 2 to 30 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent. 2 <5> The composition according to <3>, wherein X in the above formula (1) is a hydrogen atom. 1 <6> The composition according to any one of <1> to <4>, wherein L in the above formula (1) is an acid group having a pKa of 4 or less or a salt thereof. 2 represents an alkylene group having 2 to 16 carbon atoms; 3 represents a single bond. <7> The composition according to any one of <1> to <5>, wherein <7> a film obtained using the composition according to any one of <1> to <6>. <8> An optical filter having the film according to <7>. <9> A solid-state imaging device having the film according to <7>. <10> An image display device having the film according to <7>. <11> An infrared sensor having the film according to <7>. <12> A camera module having the film according to <7>. <13> A compound represented by formula (1a); In formula (1a), A 1a represents a dye skeleton derived from a dye compound selected from a pyrrolopyrrole dye compound, a phthalocyanine dye compound, a squarylium dye compound, an indigo dye compound, a croconium dye compound, an isoindoline dye compound, a quinophthalone dye compound, a diketopyrrolopyrrole dye compound, a triarylmethane dye compound, a xanthene dye compound, a pyrromethene dye compound, a perylene dye compound, an azomethine dye compound, an anthraquinone dye compound, a quinacridone dye compound, a dioxazine dye compound, and a benzofuranone dye compound; L 1a represents a single bond or a divalent linking group; 2a and L 3a each independently represents a single bond or an alkylene group having 1 to 30 carbon atoms; R 1a represents a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 2a represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent; R 1a and R 2a may be bonded to form a ring, X 1a represents an acid group or a salt thereof, and p represents an integer of 1 to 20. <14> A method for producing a compound represented by formula (1b) by reacting a dye compound with a compound represented by formula (10b); In the formula, A 1b represents a dye skeleton derived from a dye compound, and L 1b represents a single bond or a divalent linking group; 2b represents an alkylene group having 2 to 16 carbon atoms; R 1b represents a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 2b represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent; R 1b and R 2b may be bonded to form a ring, X1b represents a sulfo group or a salt thereof, and p represents an integer of 1 to 20. <15> A compound represented by formula (10c): In formula (10a), R 10c represents an alkyl group having 9 to 18 carbon atoms, an alkenyl group having 9 to 18 carbon atoms, or an alkynyl group having 9 to 18 carbon atoms.
[0009] According to the present invention, it is possible to provide a composition that has good dispersibility and storage stability and is capable of forming a film that is excellent in moisture resistance. Furthermore, according to the present invention, it is possible to provide a film, an optical filter, a solid-state imaging device, an image display device, an infrared sensor, a camera module, a compound, and a method for producing the compound.
[0010] FIG. 1 is a schematic diagram illustrating an embodiment of an infrared sensor.
[0011] The present invention will be described in detail below. In this specification, the term "to" is used to mean that the numerical values before and after the term are included as the lower and upper limits. In the description of groups (atomic groups) in this specification, a term without specifying whether it is substituted or unsubstituted encompasses both unsubstituted groups (atomic groups) and substituted groups (atomic groups). For example, the term "alkyl group" encompasses not only unsubstituted alkyl groups (unsubstituted alkyl groups) but also substituted alkyl groups (substituted alkyl groups). In this specification, unless otherwise specified, "exposure" includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams. Examples of light used for exposure include the bright line spectrum of a mercury lamp, far ultraviolet light typified by excimer lasers, extreme ultraviolet light (EUV light), X-rays, electron beams, and other actinic rays or radiation. As used herein, "(meth)acrylate" refers to either or both of acrylate and methacrylate, "(meth)acrylic" refers to either or both of acrylic and methacrylic, and "(meth)acryloyl" refers to either or both of acryloyl and methacryloyl. In the structural formulae herein, Me refers to a methyl group, Et refers to an ethyl group, Bu refers to a butyl group, and Ph refers to a phenyl group. As used herein, infrared radiation refers to light (electromagnetic waves) with a wavelength of 700 to 2500 nm. As used herein, weight-average molecular weight and number-average molecular weight are polystyrene-equivalent values measured by GPC (gel permeation chromatography). As used herein, total solids refers to the total mass of all components of a composition excluding the solvent. As used herein, pigment refers to a colorant that is difficult to dissolve in a solvent. In this specification, the term "process" includes not only an independent process but also a process that cannot be clearly distinguished from other processes as long as the intended effect of the process is achieved.
[0012] <Composition> The composition of the present invention is characterized by containing a coloring material containing a pigment, a compound represented by formula (1), a resin having an amine value, and a solvent.
[0013] The composition of the present invention has good dispersibility and storage stability, and can form a film with excellent moisture resistance. The reason for such effects is presumed to be as follows.
[0014] The compound represented by formula (1) has a dye skeleton, and is therefore presumed to interact with the pigment and adsorb to the surface of the pigment. Furthermore, the compound represented by formula (1) contains an acid group or a salt thereof, and is presumed to adsorb to the resin having an amine value through an acid-base reaction interaction. Therefore, it is presumed that a strong network structure is formed in the composition between the pigment, the compound represented by formula (1), and the resin having an amine value. It is presumed that the formation of such a network structure in the composition can suppress pigment aggregation and improve the dispersibility of the pigment. Furthermore, the compound represented by formula (1) has a structure in which R 1 is a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, so R 1 It is presumed that the site of R acts as a steric hindrance, which can suppress bridging and aggregation between the compound represented by formula (1) and the resin, thereby suppressing an increase in viscosity over time and improving storage stability. Furthermore, in a high humidity environment, the compound having a dye skeleton in the film tends to easily form associations. When the compound having a dye skeleton forms associations, the spectral characteristics of the film may fluctuate. The compound represented by formula (1) used in the composition of the present invention is 1 is the above group, so R 1 It is presumed that the moiety acts as a steric hindrance, inhibiting the formation of the association of the compound represented by formula (1) in the film. Therefore, it is presumed that even when the film obtained using the composition of the present invention is exposed to a humid environment, the fluctuation of the spectroscopic properties of the film can be suppressed. Therefore, it is presumed that the use of the composition of the present invention can form a film with excellent moisture resistance.
[0015] The composition of the present invention is preferably used as a composition for optical filters, such as color filters, infrared transmission filters, and infrared cut filters, with infrared cut filters being preferred.
[0016] The solids concentration of the composition of the present invention is preferably 5 to 30% by mass. The lower limit is preferably 7.5% by mass or more, more preferably 10% by mass or more. The upper limit is preferably 25% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less.
[0017] Each component used in the composition of the present invention will be described below.
[0018] <<Coloring Material>> The composition of the present invention contains a coloring material. Examples of the coloring material include a chromatic coloring material, an infrared absorbing coloring material, and a black coloring material.
[0019] The colorant contained in the composition of the present invention is one containing a pigment. The pigment may be either an inorganic pigment or an organic pigment, but is preferably an organic pigment from the viewpoints of a wide range of color variations, ease of dispersion, safety, etc. Examples of the pigment include chromatic pigments, infrared absorbing pigments, and black pigments. The pigment preferably contains at least one selected from chromatic pigments and infrared absorbing pigments, and more preferably contains an infrared absorbing pigment.
[0020] The colorant preferably contains at least one selected from the group consisting of pyrrolopyrrole pigments, phthalocyanine pigments, squarylium pigments, indigo pigments, croconium pigments, isoindoline pigments, quinophthalone pigments, diketopyrrolopyrrole pigments, triarylmethane pigments, xanthene pigments, pyrromethene pigments, perylene pigments, azomethine pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, and benzofuranone pigments; more preferably contains at least one selected from the group consisting of pyrrolopyrrole pigments, phthalocyanine pigments, squarylium pigments, indigo pigments, croconium pigments, isoindoline pigments, quinophthalone pigments, diketopyrrolopyrrole pigments, xanthene pigments, perylene pigments, and azomethine pigments; and even more preferably contains a pyrrolopyrrole pigment.
[0021] The average primary particle diameter of the pigment is preferably 1 to 200 nm. The lower limit is preferably 5 nm or more, more preferably 10 nm or more. The upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less. In this specification, the primary particle diameter of the pigment can be determined from a photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is determined, and the corresponding circle-equivalent diameter is calculated as the primary particle diameter of the pigment.
[0022] The crystallite size of the pigment, determined from the half-width of a peak derived from any crystal plane in an X-ray diffraction spectrum obtained using CuKα radiation as an X-ray source, is preferably 0.1 to 100 nm, more preferably 0.5 to 50 nm, even more preferably 1 to 30 nm, and particularly preferably 5 to 25 nm.
[0023] The specific surface area of the pigment is 1 to 300 m 2 / g. The lower limit is 10 m 2 / g or more, and 2 / g or more is more preferable. 2 / g or less, and 2 The value of the specific surface area can be determined according to the BET (Brunauer, Emmett and Teller) method in accordance with DIN 66131: Determination of the specific surface area of solids by gas adsorption.
[0024] (Chromatic Colorant) Examples of chromatic colorants include colorants having a maximum absorption wavelength in the wavelength range of 400 to 700 nm, such as green colorants, red colorants, yellow colorants, purple colorants, blue colorants, and orange colorants.
[0025] Examples of the red colorant include a diketopyrrolopyrrole compound, an anthraquinone compound, an azo compound, a naphthol compound, an azomethine compound, a xanthene compound, a quinacridone compound, a perylene compound, and a thioindigo compound, and the like, preferably a diketopyrrolopyrrole compound, an anthraquinone compound, or an azo compound, and more preferably a diketopyrrolopyrrole compound. The red colorant is preferably a pigment (red pigment), and more preferably a diketopyrrolopyrrole pigment.
[0026] Specific examples of red colorants include C.I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, Examples of red pigments include 150,155,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,269,270,272,279,291,294,295,296,297. In addition, as a red colorant, a compound described in paragraph 0034 of WO 2022 / 085485, or a brominated diketopyrrolopyrrole compound described in JP-A-2020-085947 can also be used.
[0027] As the red colorant, C.I. Pigment Red 122, 177, 224, 254, 255, 264, 269, 272, and 291 are preferred, C.I. Pigment Red 254, 264, and 272 are more preferred, and C.I. Pigment Red 254 and 264 are even more preferred.
[0028] Examples of the green colorant include phthalocyanine compounds and squarylium compounds, and the phthalocyanine compounds are preferred. The green colorant is preferably a pigment (green pigment), and more preferably a phthalocyanine pigment.
[0029] Specific examples of green colorants include green pigments such as C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, and 66. Furthermore, as a green colorant, a halogenated zinc phthalocyanine pigment having an average of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms per molecule can also be used. Specific examples include the compounds described in WO 2015 / 118720. Furthermore, as a green colorant, the compounds described in paragraph 0029 of WO 2022 / 085485, the aluminum phthalocyanine compounds described in JP-A 2020-070426, and the diarylmethane compounds described in JP-A 2020-504758 can also be used.
[0030] As the green colorant, C.I. Pigment Green 7, 36, 58, 62, and 63 are preferred.
[0031] Examples of orange colorants include diketopyrrolopyrrole compounds and azo compounds. The orange colorant is preferably a pigment (orange pigment). Specific examples of orange colorants include orange pigments such as C.I. Pigment Orange 2, 5, 13, 16, 17:1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, and 73.
[0032] Examples of the yellow colorant include an azo compound, an azomethine compound, an isoindoline compound, a pteridine compound, a quinophthalone compound, and a perylene compound. The yellow colorant is preferably a pigment (yellow pigment). Specific examples of the yellow colorant include C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125 , 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214, 215, 228, 231, 232, 233, 234, 235, 236 and the like.
[0033] As the yellow coloring material, an azobarbituric acid nickel complex having the following structure can also be used.
[0034] As the yellow colorant, the compounds described in paragraphs 0031 to 0033 of WO 2022 / 085485, the methine dyes described in JP-A 2019-073695, and the methine dyes described in JP-A 2019-073696 can be used.
[0035] Examples of the purple colorant include an oxazine compound, a quinacridone compound, a perylene compound, and an indigo compound, and the oxazine compound is preferred. The purple colorant is preferably a pigment (purple pigment). Specific examples of the purple colorant include purple pigments such as C.I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.
[0036] Examples of blue colorants include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred. The blue colorant is preferably a pigment (blue pigment). Specific examples of blue colorants include blue pigments such as C.I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, and 88. Furthermore, aluminum phthalocyanine compounds having phosphorus atoms can also be used as blue colorants. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP-A No. 2012-247591 and paragraph 0047 of JP-A No. 2011-157478.
[0037] Dyes can also be used as chromatic colorants. There are no particular limitations on the dyes, and known dyes can be used. Examples include pyrazole azo dyes, anilino azo dyes, triarylmethane dyes, anthraquinone dyes, anthrapyridone dyes, benzylidene dyes, oxonol dyes, pyrazolotriazole azo dyes, pyridone azo dyes, cyanine dyes, phenothiazine dyes, pyrrolopyrazole azomethine dyes, xanthene dyes, phthalocyanine dyes, benzopyran dyes, indigo dyes, and pyrromethene dyes.
[0038] A dye polymer can also be used as a chromatic colorant. The dye polymer is preferably a dye dissolved in a solvent when used. The dye polymer may also form particles. When the dye polymer is particulate, it is typically used in a dispersed state in a solvent. A particulate dye polymer can be obtained, for example, by emulsion polymerization, and specific examples of the compounds and production methods described in JP-A 2015-214682 include those described in JP-A 2015-214682. The dye polymer has two or more dye structures in one molecule, preferably three or more dye structures. The upper limit is not particularly limited, but can be 100 or less. The multiple dye structures in one molecule may be the same dye structure or different dye structures. The weight-average molecular weight (Mw) of the dye polymer is preferably 2,000 to 50,000. The lower limit is more preferably 3,000 or more, and even more preferably 6,000 or more. The upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less. As the dye multimer, compounds described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, WO 2016 / 031442, etc. can also be used.
[0039] Examples of chromatic colorants include triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in JP 2020-117638 A, phthalocyanine compounds described in WO 2020 / 174991 A, isoindoline compounds or salts thereof described in JP 2020-160279 A, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069442 A, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069730 A, and compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069730 A. Compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069070, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069067, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069062, halogenated zinc phthalocyanine pigments described in Japanese Patent No. 6809649, isoindoline compounds described in JP 2020-180176, phenothiazine compounds described in JP 2021-187913, halogenated zinc phthalocyanines described in WO 2022 / 004261, WO Halide zinc phthalocyanine described in Korean Patent Publication No. 10-2020-0030759, quinophthalone compound represented by formula 1 in Korean Patent Publication No. 10-2020-0061793, polymer dye described in Korean Patent Publication No. 10-2020-0061793, chromatic colorant described in JP-A-2022-029701, isoindoline compound described in WO 2022 / 014635, aluminum phthalocyanine compound described in WO 2022 / 024926, compound described in JP 2022-045895, WO 2022 / 05005 Compounds described in JP-A-2020-090676, compounds described in JP-A-2020-055956, compounds described in JP-A-2021-031681, compounds described in JP-A-2022-056354, compounds described in US Patent Application Publication No. 2021 / 0355327, compounds described in WO 2022 / 065357, compounds described in JP-A-2020-045436, compounds described in Korean Patent Publication No. 10-2021-0146726, compounds described in JP-A-2018-178039,Compounds described in Chinese Patent Application Publication No. 113881244, compounds described in Chinese Patent Application Publication No. 113881245, compounds described in Chinese Patent Application Publication No. 113881246, compounds described in JP 2022-104822 A, compounds described in JP 2022-096701 A, compounds described in JP 2020-023652 A, green pigments described in the Journal of the Japan Color Materials Association (published in 2022) pages 80 to 84, compounds described in JP 2022-143135 A, compounds described in JP 2022-140287 A, compounds described in WO 2014 / 014906 Compounds described in Patent Publication No. 2022 / 136308, perylene compounds described in Chinese Patent Application Publication No. 113061349, cyan pigments described in Korean Patent Publication No. 10-2017-0018993, isoindoline compounds described in JP 2020-180176, compounds described in JP 2023-013209, compounds described in JP 2023-013166, xanthene compounds described in WO 2023 / 286526, compounds described in JP 2021-155746, compounds described in JP 2021-155747, JP Compounds described in JP-A-2021-155748, compounds described in JP-A-2021-155749, compounds described in WO 2018 / 051876, compounds described in JP-A-2020-083981, compounds described in JP-A-2023-056463, compounds described in JP-T-2023-515473, dioxane compounds described in JP-T-2022-549530, pigment preparations described in JP-A-2022-061494, diketopyrrolopyrrole pigments described in JP-A-2023-057917, and JP-A-2023-061273 Diketopyrrolopyrrole compounds described in JP-A-2023-519314, phthalocyanines described in JP-A-2023-080419, quinophthalones described in JP-A-2023-103177, phthalocyanine compounds described in JP-A-2023-103177, isoindoline compounds described in JP-A-2020-026521, squarylium compounds described in Korean Patent Publication No. 10-2023-0043000, squarylium compounds described in Korean Patent Publication No. 10-2023-0050069, diketopyrrolopyrrole compounds described in JP-A-2023-127878,Triarylmethane compounds described in JP-A-2023-150459, triarylmethane compounds described in JP-A-2023-149735, core-shell dyes described in JP-A-2023-123349, xanthene compounds described in JP-T-2023-543717, compounds described in Chinese Patent Application Publication No. 116102441, compounds described in JP-A-2023-150459, compounds described in JP-A-2023-167345, compounds described in Korean Patent Publication No. 10-2023-0061078, Compounds described in JP-A-2020-183509, colorants described in JP-A-2020-079395, compounds represented by formula (1) described in U.S. Patent Application Publication No. 2022 / 0119643, dyes described in JP-A-2023-048989, compounds described in JP-A-2024-014738, pigments described in Chinese Patent Application Publication No. 115873417, compounds described in JP-A-2024-043497, compounds described in JP-A-2021-157040, azo compounds described in JP-A-2024-063075 Pigments, compounds described in JP 2022-018967 A, quinophthalone pigments described in JP 2024-057558 A, compounds described in WO 2020 / 170957 A, compounds described in Chinese Patent Application Publication No. 117209388 A, isoindoline compounds described in JP 2024-079043 A, phthalocyanine dyes described in Korean Patent Publication No. 10-2022-0026920 A, compounds described in WO 2020 / 203514 A, squarylium compounds described in JP 2020-183510 A It is also possible to use compounds such as compounds described in Korean Patent Publication No. 10-2024-0030438, squarylium compounds described in Chinese Patent Publication No. 115947727, phthalocyanine compounds described in Chinese Patent Publication No. 117700418, xanthene compounds described in Japanese Patent Application Laid-Open No. 2024-144198, xanthene compounds described in Japanese Patent Application Laid-Open No. 2020-125455, acidic dyes described in Japanese Patent Application Laid-Open No. 2024-132917, and triarylmethane compounds described in Japanese Patent Application Laid-Open No. 2024-132927. The chromatic colorant may also be a rotaxane. The dye skeleton may be used in the cyclic structure of the rotaxane,It may be used in the rod structure or in both structures.
[0040] Two or more chromatic colorants may be used in combination. When two or more chromatic colorants are used in combination, the combination of the two or more chromatic colorants may form a black color. Examples of such combinations include the following embodiments (1) to (7). When the composition contains two or more chromatic colorants and exhibits a black color through the combination of the two or more chromatic colorants, the composition of the present invention can be preferably used as a composition for forming an infrared transmission filter. (1) An embodiment containing a red colorant and a blue colorant. (2) An embodiment containing a red colorant, a blue colorant, and a yellow colorant. (3) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant. (4) An embodiment containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant. (5) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a green colorant. (6) An embodiment containing a red colorant, a blue colorant, and a green colorant. (7) An embodiment containing a yellow coloring material and a purple coloring material.
[0041] (Black Colorant) The black colorant is not particularly limited, and known materials can be used. The black colorant may be an inorganic black colorant or an organic black colorant. The black colorant is preferably a pigment. In this specification, the black colorant refers to a colorant that exhibits absorption over the entire wavelength range of 400 to 700 nm.
[0042] Examples of inorganic black colorants include carbon black, titanium black, graphite, etc., with carbon black and titanium black being preferred, and titanium black being more preferred. Titanium black is a black particle containing titanium atoms, and low-order titanium oxide or titanium oxynitride is preferred. As the titanium black, the titanium black described in paragraph 0044 of WO 2022 / 085485 can be used. As the inorganic black colorant, zirconium nitride powder described in JP 2023-048173 A can also be used.
[0043] Examples of organic black colorants include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, with bisbenzofuranone compounds and perylene compounds being preferred. The organic black colorant may be a compound described in paragraph 0166 of International Publication No. 2022 / 065215. Examples of organic black colorants include perylene black (such as Lumogen Black FK4280) described in paragraphs 0016 to 0020 of JP-A-2017-226821, black azo pigments described in JP-A-2022-121935, diketopyrrolopyrrole compounds described in JP-A-2021-172735, and bipyrrolinone compounds described in JP-T-2024-530550.
[0044] The black coloring material may be any of those described in pages 294 to 307 of the Journal of the Color Materials Association, Vol. 96, No. 9, 2023.
[0045] (Infrared absorbing colorant) The infrared absorbing colorant is preferably a compound having a maximum absorption wavelength longer than 700 nm. The infrared absorbing colorant is preferably a compound having a maximum absorption wavelength in the wavelength range of more than 700 nm to 1800 nm, more preferably a compound having a maximum absorption wavelength in the wavelength range of more than 700 nm to 1400 nm, even more preferably a compound having a maximum absorption wavelength in the wavelength range of more than 700 nm to 1200 nm, and particularly preferably a compound having a maximum absorption wavelength in the wavelength range of more than 700 nm to 1000 nm. In addition, the absorbance A of the infrared absorbing colorant at a wavelength of 500 nm is 1 and absorbance A at the maximum absorption wavelength 2 Ratio A 1 / A 2 is preferably 0.08 or less, more preferably 0.04 or less. The infrared absorbing colorant is preferably a pigment, more preferably an organic pigment.
[0046] Examples of infrared absorbing colorants include pyrrolopyrrole compounds, squarylium compounds, croconium compounds, polymethine compounds, indigo compounds, phthalocyanine compounds, naphthalocyanine compounds, iminium compounds, quaterrylene compounds, aminium compounds, azo compounds, anthraquinone compounds, porphyrin compounds, oxonol compounds, hexaphyrin compounds, and pyrromethene compounds. At least one selected from pyrrolopyrrole compounds, squarylium compounds, croconium compounds, polymethine compounds, indigo compounds, phthalocyanine compounds, and naphthalocyanine compounds is preferred, and pyrrolopyrrole compounds are more preferred. Specific examples of these include the compounds described in paragraph 0114 of WO 2022 / 065215. In addition, examples of infrared absorbing colorants include the compounds described in paragraph 0121 of WO 2022 / 065215, the squarylium compounds described in JP 2020-075959 A, Copper complexes described in Korean Patent Publication No. 10-2019-0135217, croconic acid compounds described in JP 2021-195515, infrared absorbing dyes described in JP 2022-022070, croconium compounds described in WO 2019 / 021767, compounds described in JP 2019-127549, compounds described in WO 2022 / 059619, compounds described in JP 2022-151682, squarylium compounds described in JP 2022-188858, compounds described in JP 2022-184710, compounds described in JP 2022-189736, Squarylium compounds described in JP-A-23-004570, squarylium compounds described in WO 2019 / 230660, compounds described in WO 2020 / 218615, diiminium compounds described in JP-A-2023-068643, squarylium compounds described in JP-A-2023-052770, phthalocyanine compounds described in Korean Patent Publication No. 10-2022-0163680, indigo monoboron complexes described in JP-A-2023-073064, phthalocyanine compounds described in JP-A-2023-066025, phthalocyanine compounds described in JP-A-2020-041127,Indigo compounds described in JP 2023-073064 A, indigo compounds described in Korean Patent Publication No. 10-2023-0016355 A, squarylium compounds described in WO 2019 / 230570 A, diiminium compounds described in JP 2023-095824 A, compounds described in JP 2023-159964 A, compounds described in JP 2023-176615 A, compounds described in JP 2024-500537 A, phthalocyanine compounds described in JP-A-2024-019936, compounds described in Korean Patent Registration No. 10-2575190, polymethine compounds described in JP-A-2024-017061, boron derivatives described in Chinese Patent Application Publication No. 116715690, phthalocyanine compounds described in JP-A-2024-020454, compounds described in Chinese Patent Application Publication No. 116891482, compounds described in JP-A-2024-511242, Compounds described in JP-A-047265, compounds described in JP-A-2024-043503, extended-side phthalocyanines described in JP-A-2021-047255, compounds described in WO 2024 / 058103, compounds described in JP-A-2024-071077, compounds described in U.S. Patent Application Publication No. 2021 / 0036251, compounds described in JP-A-2024-079641, cyanine compounds described in WO 2024 / 106293 , squarylium compounds described in Korean Patent Registration No. 10-2622663, squarylium compounds described in JP 2024-071077, cyanine compounds described in WO 2024 / 128016, anthraquinone dyes described in WO 2024 / 041944, xanthene compounds described in U.S. Patent Application Publication No. 2024 / 0124714, and tropylium compounds described in JP 2024-126341 can also be used. A dye polymer can also be used as the infrared-absorbing colorant.
[0047] The content of the colorant in the total solid content of the composition is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 12% by mass or more, and the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, and even more preferably 70% by mass or less.
[0048] The content of the pigment in the colorant is preferably 20 to 100% by mass, more preferably 50 to 100% by mass, and even more preferably 70 to 100% by mass. The colorant may essentially consist of only the pigment. When the colorant consists essentially of only the pigment, this means that the content of the pigment in the colorant is 99% by mass or more, and it is preferable that the colorant consists of only the pigment.
[0049] When the composition of the present invention is used as a composition for an infrared cut filter, the content of the infrared absorbing colorant in the colorant is preferably 90% by mass or more, more preferably 95% by mass or more. The colorant may be essentially an infrared absorbing colorant alone. When the colorant is essentially an infrared absorbing colorant alone, this means that the content of the infrared absorbing colorant in the colorant is 99% by mass or more, and it is preferable that the colorant is essentially an infrared absorbing colorant alone. Furthermore, it is preferable that the infrared absorbing colorant is a pigment (infrared absorbing pigment).
[0050] The coloring material may be used alone or in combination of two or more kinds. When two or more kinds are used, it is preferable that the total amount thereof is in the above range.
[0051] <<Specific Compound (Compound Represented by Formula (1))>> The composition of the present invention contains a compound represented by formula (1). Hereinafter, the compound represented by formula (1) will also be referred to as the specific compound. The specific compound is used as a dispersing aid. A dispersing aid is a material that enhances the dispersibility of a pigment in a composition.
[0052] In formula (1), A 1 represents a dye skeleton derived from a dye compound, and L 1 represents a single bond or a divalent linking group; 2 and L 3each independently represents a single bond or an alkylene group having 1 to 30 carbon atoms; R 1 represents a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 2 represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent; R 1 and R 2 may be bonded to form a ring, X 1 represents an acid group or a salt thereof; and p represents an integer of 1 to 20.
[0053] -A 1 Regarding - A in formula (1) 1 represents a pigment skeleton derived from a pigment compound. 1 is preferably a dye skeleton derived from a dye compound having a maximum absorption wavelength in the wavelength range of 400 to 2000 nm, more preferably a dye skeleton derived from a dye compound having a maximum absorption wavelength in the wavelength range of 400 to 1800 nm, and even more preferably a dye skeleton derived from a dye compound having a maximum absorption wavelength in the wavelength range of 700 to 1500 nm. In general, the longer the absorption of a dye compound is located, the more likely its spectral characteristics are to fluctuate greatly due to aggregation formation. In the present invention, the specific compound is A of formula (1) 1 Even when a dye skeleton derived from a dye compound having a maximum absorption wavelength in the wavelength range of 700 to 1500 nm is used, the formation of an association of the compound represented by formula (1) in the film can be inhibited, and therefore, even when the film is exposed to a high humidity environment, fluctuations in the spectral characteristics of the film can be suppressed. 1 When is a dye skeleton derived from a dye compound having a maximum absorption wavelength in the wavelength range of 700 to 1500 nm, the effects of the present invention are more pronounced.
[0054] A 1is preferably a dye skeleton derived from a dye compound selected from a pyrrolopyrrole dye compound, a phthalocyanine dye compound, a squarylium dye compound, an indigo dye compound, a croconium dye compound, an isoindoline dye compound, a quinophthalone dye compound, a diketopyrrolopyrrole dye compound, a triarylmethane dye compound, a xanthene dye compound, a pyrromethene dye compound, a perylene dye compound, an azomethine dye compound, an anthraquinone dye compound, a quinacridone dye compound, a dioxazine dye compound, and a benzofuranone dye compound, more preferably a dye skeleton derived from a dye compound selected from a pyrrolopyrrole dye compound, a phthalocyanine dye compound, a squarylium dye compound, an indigo dye compound, and a croconium dye compound, and even more preferably a dye skeleton derived from a pyrrolopyrrole dye compound.
[0055] (Dye skeleton derived from pyrrolopyrrole dye compound) Examples of pyrrolopyrrole dye compounds include compounds represented by formula (PP-1). Examples of dye skeletons derived from pyrrolopyrrole dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0056]
[0057] In the formula, Rp 1 and Rp 2 Rp each independently represents an alkyl group, an aryl group, or a heteroaryl group; 3 ~RP 6 each independently represents a hydrogen atom or a substituent, 7 and Rp 8 are each independently a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or —BRp 11 Rp 12 or a metal atom, 11 and Rp 12 each independently represents a substituent, 11 and Rp 12 may be bonded to each other to form a ring.
[0058] Rp 1 and Rp 2The alkyl group, aryl group, and heteroaryl group represented by may have a substituent or may be unsubstituted. Examples of the substituent include the groups listed as the substituent T shown below and the group represented by formula (R-100) described below.
[0059] Rp 1 and Rp 2 are each independently preferably an alkyl group or an aryl group, more preferably an aryl group.
[0060] Rp 3 ~RP 6 Examples of the substituent represented by the formula (I) include an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heteroaryloxycarbonyl group, an acyloxy group, an amino group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a heteroaryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a heteroarylthio group, an alkylsulfonyl group, an arylsulfonyl group, a heteroarylsulfonyl group, an alkylsulfinyl group, an arylsulfinyl group, a heteroarylsulfinyl group, a ureido group, a phosphoric acid amide group, a mercapto group, a sulfo group, a carboxy group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazino group, an imino group, a silyl group, a hydroxy group, a halogen atom, and a cyano group.
[0061] Rp 3 and Rp 4 one of Rp is a heteroaryl group and the other is an electron-withdrawing group; 5 and Rp 6 Preferably, one of the groups is a heteroaryl group and the other is an electron-withdrawing group. The heteroaryl group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T.
[0062] Here, a substituent with a positive Hammett σp value (sigma para value) acts as an electron-withdrawing group. In this specification, a substituent with a Hammett σp value of 0.2 or more can be exemplified as an electron-withdrawing group. The σp value is preferably 0.25 or more, more preferably 0.3 or more, and particularly preferably 0.35 or more. There is no particular upper limit, but it is preferably 0.80 or less. Specific examples of electron-withdrawing groups include a cyano group (0.66), a carboxy group (-COOH: 0.45), an alkoxycarbonyl group (for example, -COOCH 3 : 0.45), aryloxycarbonyl groups (e.g., —COOCH 3 : 0.44), carbamoyl group (e.g., —CONH 2 : 0.36), alkylcarbonyl groups (e.g., —COCH 3 : 0.50), arylcarbonyl groups (e.g., -COPh: 0.43), alkylsulfonyl groups (e.g., -SO 2 CH 3 : 0.72), arylsulfonyl groups (e.g., —SO 2 The electron-withdrawing group is preferably a cyano group, an alkylcarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group, and more preferably a cyano group. That is, R in formula (1) 1 and R 2 One of the two, and R 3 and R 4 and (b) are each preferably a cyano group. Here, Ph represents a phenyl group. For the Hammett σp value, see paragraphs 0024 and 0025 of JP-A-2009-263614, the contents of which are incorporated herein by reference.
[0063] Rp 7 and Rp 8 are each independently a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or —BRp 11 Rp 12 or a metal atom, 11 Rp 12 It is preferable that Rp 11 and Rp 12Rp each independently represents a substituent. 11 and Rp 12 Examples of the substituent represented by include a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, and a heteroaryloxy group, and it is preferably a halogen atom, an alkyl group, an aryl group, or a heteroaryl group, more preferably a halogen atom, an alkyl group, or an aryl group, and even more preferably an aryl group. The alkyl group, the alkenyl group, the aryl group, the heteroaryl group, the alkoxy group, the aryloxy group, and the heteroaryloxy group may have a substituent. Examples of the substituent include the groups listed below for the substituent T. Rp 7 and Rp 8 Examples of the metal atom represented by include Mg, Al, Ca, Ba, Zn, Sn, V, Fe, Co, Ni, Cu, Pd, and Pt.
[0064] Examples of the substituent T include the following groups: a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom), an alkyl group (preferably an alkyl group having 1 to 30 carbon atoms), an alkenyl group (preferably an alkenyl group having 2 to 30 carbon atoms), an alkynyl group (preferably an alkynyl group having 2 to 30 carbon atoms), an aryl group (preferably an aryl group having 6 to 30 carbon atoms), a heteroaryl group (preferably a heteroaryl group having 1 to 30 carbon atoms), an amino group (preferably an amino group having 0 to 30 carbon atoms), an alkoxy group (preferably an alkoxy group having 1 to 30 carbon atoms), an aryloxy group (preferably or an aryloxy group having 6 to 30 carbon atoms), a heteroaryloxy group (preferably a heteroaryloxy group having 1 to 30 carbon atoms), an acyl group (preferably an acyl group having 2 to 30 carbon atoms), an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 30 carbon atoms), an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 30 carbon atoms), a heteroaryloxycarbonyl group (preferably a heteroaryloxycarbonyl group having 2 to 30 carbon atoms), an acyloxy group (preferably an acyloxy group having 2 to 30 carbon atoms), group), acylamino group (preferably an acylamino group having 2 to 30 carbon atoms), aminocarbonylamino group (preferably an aminocarbonylamino group having 2 to 30 carbon atoms), alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms), aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms), sulfamoyl group (preferably a sulfamoyl group having 0 to 30 carbon atoms), sulfamoylamino group (preferably a sulfamoylamino group having 0 to 30 carbon atoms), carboxylic acid a bamoyl group (preferably a carbamoyl group having 1 to 30 carbon atoms), an alkylthio group (preferably an alkylthio group having 1 to 30 carbon atoms), an arylthio group (preferably an arylthio group having 6 to 30 carbon atoms), a heteroarylthio group (preferably a heteroarylthio group having 1 to 30 carbon atoms), an alkylsulfonyl group (preferably an alkylsulfonyl group having 1 to 30 carbon atoms), an alkylsulfonylamino group (preferably an alkylsulfonylamino group having 1 to 30 carbon atoms), an arylsulfonyl group (preferably an arylsulfonyl group having 6 to 30 carbon atoms),an arylsulfonylamino group (preferably an arylsulfonylamino group having 6 to 30 carbon atoms), a heteroarylsulfonyl group (preferably a heteroarylsulfonyl group having 1 to 30 carbon atoms), a heteroarylsulfonylamino group (preferably a heteroarylsulfonylamino group having 1 to 30 carbon atoms), an alkylsulfinyl group (preferably an alkylsulfinyl group having 1 to 30 carbon atoms), an arylsulfinyl group (preferably an arylsulfinyl group having 6 to 30 carbon atoms), a heteroarylsulfinyl group (preferably a heteroarylsulfinyl group having 1 to 30 carbon atoms), a ureido group (preferably a ureido group having 1 to 30 carbon atoms), a hydroxy group, a nitro group, a carboxy group, a sulfo group, a phosphoric acid group, a carboxylic acid amide group, a sulfonic acid amide group, an imido group, a phosphino group, a mercapto group, a cyano group, an alkylsulfino group, an arylsulfino group, an arylazo group, a heteroarylazo group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a silyl group, a hydrazino group, or an imino group. When these groups are groups that can be further substituted, they may further have a substituent. Examples of the substituent include the groups described above for the substituent T.
[0065] The group represented by formula (R-100) is shown below.
[0066] In the formula, Rp 1a represents an alkyl group, an aryl group, or a heteroaryl group; 3a ~RP 6a each independently represents a hydrogen atom or a substituent, 7a and Rp 8a are each independently a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, or —BRp 11 Rp 12 or a metal atom, 11 and Rp 12 each independently represents a substituent, 11 and Rp 12 may be bonded to each other to form a ring, Lp 1 represents a single bond or a divalent linking group.
[0067] Rp in formula (R-100)1a , Rp 3a ~RP 8a is Rp in formula (PP-1). 1 , Rp 3 ~RP 8 The same applies to the preferred range.
[0068] Lp of formula (R-100) 1 represents a single bond or a divalent linking group. Examples of the divalent linking group include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, —O—, —S—, and —NR L1 -, -CO-, -COO-, -OCO-, -SO 2 - or a group consisting of a combination thereof. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 20, more preferably 2 to 20, even more preferably 2 to 10, and particularly preferably 2 to 5. The aliphatic hydrocarbon group may be linear, branched, or cyclic. The aliphatic hydrocarbon group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T above. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10. The aromatic hydrocarbon group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T above. The heterocyclic group is preferably a monocyclic ring or a fused ring having 2 to 4 rings. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3. The heteroatom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom, or a sulfur atom. The number of carbon atoms constituting the ring of the heterocyclic group is preferably 1 to 30, more preferably 1 to 18, and even more preferably 1 to 12. The heterocyclic group may have a substituent. Examples of the substituent include the groups exemplified above as the substituent T.
[0069] (Dye skeleton derived from phthalocyanine dye compound) Examples of the phthalocyanine dye compound include compounds represented by formula (PC-1). Examples of the dye skeleton derived from the phthalocyanine dye compound include structures in which one or more hydrogen atoms have been removed from the above compound.
[0070]
[0071] In formula (PC-1), R pc1 ~R pc16each independently represents a hydrogen atom or a substituent, and the adjacent R pc1 ~R pc16 may each independently bond to each other to form an aromatic ring, M 2 represents two hydrogen atoms or a metal atom which may be coordinated with a ligand.
[0072] R pc1 ~R pc16 Examples of the substituent represented by include the groups exemplified as the substituent T described above, and are preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, or an arylsulfonyl group.
[0073] M 2 Examples of the metal atom represented by include Pd, Cu, Zn, Pt, Ni, Ti, Co, Fe, Mn, Sn, Al, Si, V, In, B, Ga, Sc, Zr, Hf, Nb, Ta, and Ge, and Cu, Zn, or Al is preferred.
[0074] M 2 The metal atom represented by may have a ligand attached thereto. The ligand may be an oxygen atom, a halogen atom, or a —OR M1 , -OCOR M1 , -OSO 2 R M1 , and ligands represented by formula (Lg6) to formula (Lg8). M1 represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.
[0075]
[0076] In formula (Lg6), R 6a and R 6b each independently represents a hydroxy group, an alkyl group, a heterocyclic group, an aryl group, an alkoxy group, a heterocyclic oxy group, or an aryloxy group; R 6a and R 6b may be bonded to each other to form a ring, and * is a coordination site with a metal atom.
[0077] The ligand represented by formula (Lg6) is also preferably a residue obtained by removing a hydrogen atom from the OH group on the phosphorus atom of the compound described in paragraph 0080 of JP-A 2022-091099, or a residue obtained by removing a hydrogen atom from the OH group on the phosphorus atom of a phosphate ester compound having an ethylenically unsaturated bond-containing group described in paragraphs 0045 to 0048 of JP-A 2019-105713.
[0078]
[0079] In formula (Lg7), R 7a and R 7b each independently represents a hydrogen atom, a hydroxy group, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, or a group represented by formula (Lg10), R 7a and R 7b At least one of the groups represented by formula (Lg10) is a group represented by formula (Lg10), and * is a coordination site with a metal atom. 8 Is -OSO 2 represents -, -OCO-, or -O-; 8 represents a single bond or an n8+1-valent linking group, Pm 8 represents a polymer chain, n8 represents an integer of 1 to 5, and when n8 is 2 to 5, a plurality of Pm 8 may be the same or different, and * is a coordination site with a metal atom.
[0080] In the formula (Lg10), L 10 represents a single bond or an n10+1-valent linking group, Pm 10 represents a polymer chain, n10 represents an integer of 1 to 5, and when n10 is 2 to 5, a plurality of Pm 10 may be the same or different, and * represents a bond to P in formula (Lg7).
[0081] L in formula (Lg8) 8 and L of formula (Lg10) 10Examples of the n10+1-valent linking group represented by include hydrocarbon groups, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and groups combining two or more of these. Examples of the hydrocarbon group include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 1 to 15. The aliphatic hydrocarbon group may be linear, branched, or cyclic. The aromatic hydrocarbon group preferably has 6 to 30 carbon atoms, more preferably 6 to 20, and even more preferably 6 to 10. The hydrocarbon group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T described below, and preferred are a halogen atom, a hydroxy group, an alkyl group, and an aryl group.
[0082] Pm in formula (Lg8) 8 and a polymer chain represented by the formula (Lg10): 10 The polymer chain represented by is preferably a polymer chain containing repeating units of at least one structure selected from a polyether structure, a polyester structure, and a poly(meth)acrylic structure.
[0083] Pm in formula (Lg8) 8 and a polymer chain represented by the formula (Lg10): 10 The weight average molecular weight of the polymer chain represented by is preferably 1,000 to 50,000, and more preferably 1,500 to 20,000.
[0084] In formula (Lg8), n8 represents an integer of 1 to 5, preferably 1 or 2, and more preferably 1. In formula (Lg10), n10 represents an integer of 1 to 5, preferably 1 or 2, and more preferably 1.
[0085] (Dye skeleton derived from indigo dye compound) Examples of indigo dye compounds include compounds represented by formula (In-1). Examples of dye skeletons derived from indigo dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0086] In formula (In-1), A in1 and A in2each independently represents an aryl group, a heteroaryl group, or an alkyl group; in1 ~X in4 R each independently represents an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a halogen atom; in1 ~R in8 each independently represents a hydrogen atom or a substituent; in1 and X in2 , X in3 and X in4 may be linked to each other to form a ring.
[0087] R in1 ~R in8 Examples of the substituent represented by include the groups exemplified above as the substituent T.
[0088] (Dye Skeleton Derived from Xanthene Dye Compound) Examples of xanthene dye compounds include compounds represented by formula (XT-1). Examples of dye skeletons derived from xanthene dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0089]
[0090] In formula (XT-1), R xt1 ~R xt4 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a group represented by formula (1), R xt5 represents a substituent, m represents an integer of 0 to 5, Z xt represents a counter anion. xt If there is no xt1 ~R xt5 At least one of the groups contains an anionic group.
[0091] R xt1 ~R xt4 The alkyl group and aryl group represented by R may have a substituent. Examples of the substituent include the groups listed above for the substituent T, anionic groups, etc. xt5 Examples of the substituent represented by include the groups exemplified above as the substituent T, anionic groups, and the like.
[0092] In formula (XT-1), Z xtrepresents a counter anion. The counter anion may be an organic anion or an inorganic anion. Examples of the counter anion include an anion represented by formula (AN1), an anion represented by formula (AN2), an anion represented by formula (AN3), an anion represented by formula (AN4), an anion represented by formula (AN5), a fluorine anion, a chlorine anion, a bromine anion, an iodine anion, a cyanide ion, a perchlorate anion, a carboxylate anion, a sulfonate anion, and a phosphate anion.
[0093] In formula (AN1), R AN1 and R AN2 each independently represents a halogen atom or an alkyl group, R AN1 and R AN2 may be bonded to form a ring; AN3 ~R AN5 each independently represents a halogen atom or an alkyl group; R AN3 and R AN4 , R AN4 and R AN5 , or R AN3 and R AN5 may be bonded to form a ring; AN6 ~R AN9 each independently represents a halogen atom, an alkyl group, an aryl group, an alkoxy group, an aryloxy group, or a cyano group; AN10 represents a halogenated hydrocarbon group which may be linked via a linking group having a nitrogen atom or an oxygen atom; AN11 ~R AN16 each independently represents a halogen atom or a halogenated hydrocarbon group.
[0094] In formula (XT-1), R xt1 ~R xt5 When at least one of the above contains an anionic group, examples of the anionic group include a group represented by formula (An-1) and a group represented by formula (An-2).
[0095] In formula (An-1), L AN1represents a single bond or a p+1 valent linking group; An 1 is -SO 3 - , -COO - , -PO 3 H - , -CON ― SO 2 R an1 , -SO 2 N ― SO 2 R an1 or -SO 2 N ― COR an1 represents R an1 represents an alkyl group or an aryl group, and p represents an integer of 1 to 4.
[0096] In formula (An-2), L AN2 and L AN4 each independently represents a single bond or a divalent linking group; AN3 , -CON ― SO 2 -, -SO 2 N ― SO 2 -or-SO 2 N ― represents CO-, AN1 and R AN2 each independently represents an alkylene group or an arylene group; 2 is -SO 3 - , -COO - or -PO 3 H - Represents.
[0097] L in formula (An-1) AN1 Examples of the p+1-valent linking group represented by the formula (1) include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -CO-, -NH-, -COO-, -OCO-, -CONH-, -NHCO-, and -SO 2 -, -SO 2 NH-, -NHSO 2 -, -S- and groups formed by combining two or more of these groups.
[0098] L in formula (An-2) AN2 and L AN4Examples of the divalent linking group represented by include an alkylene group, an arylene group, a heterocyclic group, —O—, —CO—, —NH—, —COO—, —OCO—, —CONH—, —NHCO—, and —SO 2 -, -SO 2 NH-, -NHSO 2 -, -S- and groups formed by combining two or more of these groups.
[0099] (Dye skeleton derived from triarylmethane dye compound) Examples of triarylmethane dye compounds include compounds represented by formula (TP-1). Examples of dye skeletons derived from triarylmethane dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0100]
[0101] In formula (TP-1), R tp1 ~R tp4 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a group represented by formula (1), R tp5 is a hydrogen atom, an alkyl group, an aryl group, or NR tp9 R tp10 (R tp9 and R tp10 represents a hydrogen atom, an alkyl group, or an aryl group, and R tp6 , R tp7 and R tp8 each independently represents a substituent; a, b, and c each independently represent an integer of 0 to 4; when a, b, and c are 2 or more, R t p 6 Comrade, R tp7 Peers and R tp8 may be linked to each other to form a ring, tp represents a counter anion, and Z tp If there is no tp1 ~R tp8 At least one of the groups contains an anionic group.
[0102] R tp1 ~R tp5 , R tp9 and R tp10The alkyl group and aryl group represented by R may have a substituent. Examples of the substituent include the groups listed above for the substituent T, anionic groups, etc. tp6 , R tp7 and R tp8 Examples of the substituent represented by include the groups listed above as the substituent T, anionic groups, and the like.
[0103] In formula (TP-1), Z tp represents a counter anion. tp If there is no tp1 ~R tp8 At least one of the counter anions includes an anion. Examples of the counter anion include the counter anions described above in formula (XT-1). tp1 ~R tp8 When at least one of the above groups contains an anionic group, examples of the anionic group include the group represented by the above formula (An-1) and the group represented by the above formula (An-2).
[0104] (Dye skeleton derived from squarylium dye compound, dye skeleton derived from croconium dye compound) Examples of squarylium dye compounds include compounds represented by formula (SQ-1). Examples of dye skeletons derived from squarylium dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds. Examples of croconium dye compounds include compounds represented by formula (CR-1). Examples of dye skeletons derived from croconium dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0105] In formula (SQ-1), As 1 and As 2 each independently represents an aryl group, a heterocyclic group, or a group represented by formula (As-1); 11 and As 12 each independently represents an aryl group, a heterocyclic group, or a group represented by formula (As-1); In the formula, * represents a bond, and Rs 1 ~Rs 3 each independently represents a hydrogen atom or an alkyl group; As 3represents a heterocyclic group; s1 represents an integer of 0 or more, 1 and Rs. 2 may be bonded to each other to form a ring, Rs 1 and As 3 may be bonded to each other to form a ring, Rs 2 and Rs. 3 may be bonded to each other to form a ring, s1 If Rs is 2 or more, multiple Rs 2 and Rs. 3 may be the same or different.
[0106] As 1 , As 2 , As 11 and As 12 The aryl group represented by is preferably 6 to 48 carbon atoms, more preferably 6 to 22 carbon atoms, and particularly preferably 6 to 12 carbon atoms. 1 , As 2 , As 11 and As 12 The aryl group represented by may have a substituent.
[0107] As 1 , As 2 , As 3 , As 11 and As 12 The heterocyclic group represented by is preferably a 5- or 6-membered heterocyclic group. The heterocyclic group is preferably a monocyclic heterocyclic group or a heterocyclic group having 2 to 8 fused rings, more preferably a monocyclic heterocyclic group or a heterocyclic group having 2 to 4 fused rings, more preferably a monocyclic heterocyclic group or a heterocyclic group having 2 or 3 fused rings, and particularly preferably a monocyclic heterocyclic group or a heterocyclic group having 2 fused rings. Examples of heteroatoms constituting the ring of the heterocyclic group include a nitrogen atom, an oxygen atom, and a sulfur atom, with a nitrogen atom and a sulfur atom being preferred. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3, more preferably 1 to 2. As 1 , As 2 , As 3 , As 11 and As 12 The heterocyclic group represented by may have a substituent.
[0108] Rs in formula (As-1) 1 ~Rs 3 Rs each independently represents a hydrogen atom or an alkyl group. 1 ~Rs 3 The number of carbon atoms in the alkyl group represented by Rs is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 8. The alkyl group may be linear, branched, or cyclic, and is preferably linear or branched. 1 ~Rs 3 is preferably a hydrogen atom.
[0109] n in formula (As-1) s1 represents an integer of 0 or more. s1 is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0.
[0110] In formula (As-1), Rs 1 and Rs. 2 may be bonded to each other to form a ring, Rs 1 and As 3 may be bonded to each other to form a ring, Rs 2 and Rs. 3 may be bonded to each other to form a ring. When forming the above ring, the linking group is preferably a divalent linking group selected from the group consisting of -CO-, -O-, -NH-, an alkylene group having 1 to 10 carbon atoms, and a combination thereof. The alkylene group as the linking group may be unsubstituted or may have a substituent.
[0111] (Dye Skeleton Derived from Diketopyrrolopyrrole Dye Compound) Examples of the diketopyrrolopyrrole dye compound include a compound represented by formula (DPP-1). Examples of the dye skeleton derived from the diketopyrrolopyrrole dye compound include a structure in which one or more hydrogen atoms have been removed from the above compound.
[0112]
[0113] In the formula, Ar dp1 and Ar dp2 each independently represents an aryl group or a heteroaryl group; R dp1 and R dp2each independently represents a hydrogen atom or a substituent.
[0114] Ar dp1 and Ar dp2 The aryl group and heteroaryl group represented by may have a substituent. Examples of the substituent include the groups listed above for the substituent T. dp1 and R dp2 The substituent represented by includes an alkyl group and an aryl group.
[0115] (Dye Skeleton Derived from Azomethine Dye Compound) Examples of the azomethine dye compound include a compound represented by formula (AZ-1) and a metal complex in which a compound represented by formula (AZ-1) is coordinated to a metal atom. Examples of the metal atom include monovalent to trivalent metal atoms such as Ni, Cu, Zn, Al, Ti, Fe, Mn, Co, Pd, and Na. Examples of the dye skeleton derived from an azomethine dye compound include a structure in which one or more hydrogen atoms have been removed from the above-mentioned compound or a metal complex thereof.
[0116]
[0117] In formula (AZ-1), Ar az1 and Ar az2 each independently represents an aromatic ring group or a heterocyclic group.
[0118] (Dye Skeleton Derived from Isoindoline Dye Compound) Examples of isoindoline dye compounds include compounds represented by formula (ISO-1). Examples of dye skeletons derived from isoindoline dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0119]
[0120] In the formula, R iso1 represents a hydrogen atom or a substituent. iso2 , R iso3 , R iso8 and R iso9 each independently represents an aryl group, a heteroaryl group, a cyano group, an acyl group, or an aminocarbonyl group; R iso4 , R iso5 , R iso6 and Riso7 each independently represents a hydrogen atom or a substituent, iso4 and R iso5 , R iso5 and R iso6 , R iso6 and R iso7 may be linked to each other to form a ring.
[0121] R iso1 , R iso4 , R iso5 , R iso6 and R iso7 Examples of the substituent represented by include the groups exemplified above as the substituent T.
[0122] The quinophthalone dye compound may be a compound represented by formula (QUI-1): The dye skeleton derived from a pyrromethene dye compound may be a structure in which one or more hydrogen atoms have been removed from the above compound.
[0123]
[0124] In the formula, R qui1 ~R qui6 each independently represents a hydrogen atom, a substituent, or a group represented by formula (QUI-2), qui7 ~R qui10 each independently represents a hydrogen atom or a substituent, qui7 and R qui8 , R qui8 and R qui9 , R qui9 and R qui10 may be linked to each other to form a ring, and n-qui represents 1 or 2. In the ceremony, L qui represents a single bond or a divalent linking group, * represents a bond, and QUI represents a group represented by formula (QUI-3). In the formula, R qui11 ~R qui16 each independently represents a hydrogen atom or a substituent, qui17 ~R qui20 each independently represents a hydrogen atom or a substituent, qui17 and R qui18 , R qui18 and R qui19 , Rqui19 and R qui20 may be linked together to form a ring, m-qui represents 1 or 2, R qui11 ~R qui20 At least one of the following is L in formula (QUI-2): qui and has a bond.
[0125] (Dye Skeleton Derived from Pyrromethene Dye Compound) Examples of pyrromethene dye compounds include compounds represented by formula (PYR-1). Examples of dye skeletons derived from pyrromethene dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0126]
[0127] In the formula, A pyr is N or CR pyr7 represents R pyr1 ~R pyr6 are each independently a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, an acyl group, an alkoxy group, an aryloxy group, or an NR pyr8 represents R pyr7 represents a hydrogen atom or a substituent, R pyr8 represents a hydrogen atom or a substituent, M represents -BR pyr9 R pyr10 or a metal atom, R pyr9 and R pyr10 each independently represents a substituent.
[0128] R pyr7 and R pyr8 Examples of the substituent represented by include the groups listed above as the substituent T. pyr9 and R pyr10 Examples of the substituent represented by M include a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, and a heteroaryloxy group. These groups may further have a substituent. Examples of the substituent include the groups listed above for the substituent T. Examples of the metal atom represented by M include Zn, Cu, and Pd.
[0129] (Dye skeleton derived from perylene dye compound) Examples of perylene dye compounds include compounds represented by formula (PER-1). Examples of dye skeletons derived from perylene dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0130]
[0131] In the formula, A per1 ~A per4 is an oxygen atom or NR pyr11 represents R per1 ~R per4 , R per6 ~R per9 , R per11 each independently represents a hydrogen atom or a substituent, per5 and R per10 each independently represents a substituent, per1 and R per2 , R per2 and R per3 , R per3 and R per4 , R per11 and R per5 , R per6 and R per7 , R per7 and R per8 , R per8 and R per9 , R per11 and R per10 may be linked to each other to form a ring.
[0132] R per1 ~R per11 Examples of the substituent represented by include the groups exemplified above as the substituent T.
[0133] (Dye Skeleton Derived from Anthraquinone Dye Compound) Examples of the anthraquinone dye compound include a compound represented by formula (ANT-1). Examples of the dye skeleton derived from an anthraquinone dye compound include a structure in which one or more hydrogen atoms have been removed from the above compound.
[0134]
[0135] In the formula, R ant1 ~R ant8each independently represents a hydrogen atom or a substituent, R ant1 ~R ant8 At least one of R is a substituent. ant1 ~R ant8 Examples of the substituent represented by include the groups exemplified above as the substituent T.
[0136] (Dye Skeleton Derived from Quinacridone Dye Compound) Examples of quinacridone dye compounds include compounds represented by formula (QND-1). Examples of dye skeletons derived from quinacridone dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0137]
[0138] In the formula, R qnd1 ~R qnd5 , R qnd7 ~R qnd11 each independently represents a hydrogen atom or a substituent, qnd6 and R qnd12 R each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. qnd1 ~R qnd5 , R qnd7 ~R qnd11 Examples of the substituent represented by include the groups exemplified above as the substituent T.
[0139] (Dye skeleton derived from dioxazine dye compound) Examples of dioxazine dye compounds include compounds represented by formula (DOZ-1). Examples of dye skeletons derived from dioxazine dye compounds include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0140]
[0141] In the formula, R doz1 ~R doz5 , R doz7 ~R doz11 each independently represents a hydrogen atom or a substituent, doz6 and R doz12 R each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. doz1 ~R doz5 , Rdoz7 ~R doz11 Examples of the substituent represented by include the groups exemplified above as the substituent T.
[0142] (Dye skeleton derived from benzofuranone dye compound) Examples of the benzofuranone dye compound include compounds represented by formulas (BF-1) to (BF-3). Examples of the dye skeleton derived from a benzofuranone dye compound include structures in which one or more hydrogen atoms have been removed from the above compounds.
[0143] In the above formula, R bf1 and R bf2 each independently represents a hydrogen atom or a substituent, R bf3 and R bf4 each independently represents a substituent, a and b each independently represents an integer of 0 to 4, and when a is 2 or more, a plurality of R bf3 may be the same or different, and multiple R bf3 may be bonded to form a ring, and when b is 2 or more, a plurality of R bf4 may be the same or different, and multiple R bf4 may be bonded to form a ring.
[0144] R bf1 ~R bf4 Examples of the substituent represented by include the groups exemplified above as the substituent T.
[0145] -L 1 Regarding L in formula (1) 1 represents a single bond or a divalent linking group, and is preferably a divalent linking group. 1 The divalent linking group represented by is —O—, —S—, —CO—, —COO—, —OCO—, —SO 2 -, -NR L -, -NR L CO-, -CONR L -, -NR L SO 2 -, -SO 2 NR L -, and groups formed by combining at least one of these groups with at least one group selected from a hydrocarbon group and a heterocyclic group.L represents a hydrogen atom, an alkyl group, or an aryl group.
[0146] Examples of the hydrocarbon group include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon group preferably has 1 to 20 carbon atoms, more preferably 2 to 20 carbon atoms, even more preferably 2 to 10 carbon atoms, and particularly preferably 2 to 5 carbon atoms. The aliphatic hydrocarbon group may be linear, branched, or cyclic. The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms. The heterocyclic group is preferably a monocyclic ring or a fused ring having 2 to 4 fused rings. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3. The heteroatoms constituting the ring of the heterocyclic group are preferably nitrogen atoms, oxygen atoms, or sulfur atoms. The number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12. The aliphatic hydrocarbon group, aromatic hydrocarbon group, and heterocyclic group may have a substituent. Examples of the substituent include the groups listed above for the substituent T.
[0147] R L The number of carbon atoms in the alkyl group represented by R is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 8. The alkyl group may be linear, branched, or cyclic, and is preferably linear or branched, and more preferably linear. L The alkyl group represented by may have a substituent. Examples of the substituent include the groups listed above for the substituent T. L The number of carbon atoms in the aryl group represented by R is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12. L The aryl group represented by may have a substituent. Examples of the substituent include the groups listed above for the substituent T.
[0148] L 1 L of the divalent linking group represented by 2 The terminal of the side is preferably —O—, —COO— or —OCO—, and more preferably —O—.
[0149] L 1The divalent linking group represented by is preferably a group represented by formula (L1-1). *1 -L 11 -L 13 -L 12 - *2 ... (L1-1)
[0150] (L1-1) *1 is A in formula (1) 1 represents a bond with *2 is L in formula (1). 2 Represents a bond with .
[0151] L in (L1-1) 11 represents a single bond, —O—, —S—, —CO—, —COO—, —OCO—, or —SO 2 -, -NR L -, -NR L CO-, -CONR L -, -NR L SO 2 -or-SO 2 NR L represents -, and R L represents a hydrogen atom, an alkyl group, or an aryl group.
[0152] L in (L1-1) 12 represents —O—, —COO— or —OCO—, and is preferably —O—.
[0153] L in (L1-1) 13 represents a hydrocarbon group, a heterocyclic group, a group in which a plurality of hydrocarbon groups are bonded together via a single bond or a linking group, a group in which a plurality of heterocyclic groups are bonded together via a single bond or a linking group, or a group in which a hydrocarbon group and a heterocyclic group are bonded together via a single bond or a linking group, and the linking group is selected from the group consisting of -O-, -S-, -CO-, -COO-, -OCO-, -SO 2 -, -NR L -, -NR L CO-, -CONR L -, -NR L SO 2 -or-SO 2 NR L - and R L represents a hydrogen atom, an alkyl group, or an aryl group. 13The preferred ranges of the hydrocarbon group and heterocyclic group in 1 The hydrocarbon group and heterocyclic group have the same meanings as those explained above.
[0154] -L 2 and L 3 Regarding L in formula (1) 2 and L 3 each independently represents a single bond or an alkylene group having 1 to 30 carbon atoms.
[0155] L 2 The number of carbon atoms in the alkylene group represented by is preferably 2 to 16. The upper limit is preferably 10 or less, more preferably 5 or less. The lower limit is preferably 3 or more. 2 The alkylene group represented by is preferably a straight chain.
[0156] L 3 The alkylene group represented by is preferably 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, and even more preferably 1 or 2 carbon atoms. 3 The alkylene group represented by is preferably a straight chain.
[0157] L 2 is an alkylene group having 2 to 16 carbon atoms, and L 3 is preferably a single bond.
[0158] -R 1 and R 2 Regarding - R in formula (1) 1 represents a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 2 represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent; R 1 and R 2 may be bonded to form a ring.
[0159] Examples of the hydrocarbon group include an alkyl group, an alkenyl group, an alkynyl group, and an aryl group. An alkyl group or an aryl group is preferred, and an alkyl group is more preferred. The number of carbon atoms in the alkyl group is preferably 2 to 30. The upper limit is preferably 25 or less, more preferably 20 or less, and even more preferably 18 or less. The lower limit is preferably 3 or more, more preferably 5 or more, even more preferably 6 or more, and particularly preferably 9 or more. The number of carbon atoms in the alkyl group is particularly preferably 9 to 18, because this more significantly enhances the effects of the present invention. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear, because this further improves dispersibility. The number of carbon atoms in the alkenyl group is preferably 2 to 30. The upper limit is preferably 25 or less, more preferably 20 or less, and even more preferably 17 or less. The lower limit is preferably 4 or more, and more preferably 7 or more. The number of carbon atoms in the alkynyl group is preferably 2 to 30. The upper limit is preferably 25 or less, more preferably 20 or less, and even more preferably 17 or less. The lower limit is preferably 4 or more, and more preferably 7 or more. The number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, even more preferably 6 to 12, and particularly preferably 6.
[0160] The number of carbon atoms constituting the ring of the heteroaryl group is preferably 1 to 15, and more preferably 1 to 10. Types of heteroatoms constituting the ring of the heteroaryl group include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3. The heteroaryl group may be a monocyclic ring or a fused ring.
[0161] The hydrocarbon group and heteroaryl group may have a substituent, but preferably have no substituent. Examples of the substituent include the groups listed above for the substituent T.
[0162] R in formula (1) 1 and R 2 may be bonded to form a ring. The ring formed is preferably a 5-membered or 6-membered ring.
[0163] R in formula (1) 1 is preferably an alkyl group having 2 to 30 carbon atoms which may have a substituent or an aryl group having 6 to 30 carbon atoms which may have a substituent, more preferably an alkyl group having 2 to 30 carbon atoms which may have a substituent, because this can further improve dispersibility, and even more preferably an unsubstituted alkyl group having 2 to 30 carbon atoms.
[0164] R in formula (1) 2 is preferably a hydrogen atom, an alkyl group having 2 to 30 carbon atoms which may have a substituent, or an aryl group having 6 to 30 carbon atoms which may have a substituent, more preferably a hydrogen atom or an alkyl group having 2 to 30 carbon atoms which may have a substituent, and even more preferably a hydrogen atom because this can further improve dispersibility.
[0165] -X 1 Regarding - X in formula (1) 1 represents an acid group or a salt thereof. 1 Examples of the acid group represented by and salts thereof include a carboxy group, a sulfo group, a phosphoric acid group, a phosphonic acid group, a phosphinic acid group, a boronic acid group, and an imide acid group and salts thereof. 2 NHSO 2 R X1 , -CONHSO 2 R X2 , -CONHCOR X3 or -SO 2 NHCOR X4 A group represented by the formula: 2 NHSO 2 R X1 , -CONHSO 2 R X2 , or -SO 2 NHCOR X4 A group represented by the formula: 2 NHSO 2 RX1 or -CONHSO 2 R X2 is more preferred. X1 ~R X4 R each independently represents an alkyl group or an aryl group. X1 ~R X4 The alkyl group and aryl group represented by R may have a substituent. The substituent is preferably a halogen atom, more preferably a fluorine atom. X1 ~R X4 are each independently preferably an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, more preferably an alkyl group containing a fluorine atom. The number of carbon atoms in the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. The number of carbon atoms in the aryl group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6. The atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K. + etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ Examples of the ammonium ion include ammonium ions, imidazolium ions, pyridinium ions, and phosphonium ions. Ammonium ions, imidazolium ions, and pyridinium ions are preferred, and ammonium ions are more preferred. The ammonium ions are preferably quaternary ammonium ions. The molecular weight of the ammonium ions is preferably 240 to 1,141, more preferably 354 to 1,028, and even more preferably 466 to 916.
[0166] X in formula (1) 1is preferably an acid group having a pKa of 4 or less (more preferably an acid group having a pKa of 2 or less) or a salt thereof, and more preferably an acid group having a pKa of 4 or less (more preferably an acid group having a pKa of 2 or less), because this can further improve dispersibility and storage stability. pKa is the equilibrium constant Ka of a dissociation reaction in which a hydrogen ion is released from an acid, expressed as its negative common logarithm pKa. In this specification, pKa is a value calculated using software (Advanced Chemistry Development (ACD / Labs) Software V8.14 for Solaris (1994-2007 ACD / Labs)).
[0167] Examples of the acid group having a pKa of 4 or less include a sulfo group, an imide group, and a carboxy group, with a sulfo group being preferred.
[0168] -Regarding p- In formula (1), p represents an integer of 1 to 20, preferably an integer of 1 to 10, more preferably an integer of 1 to 8, even more preferably an integer of 1 to 4, and particularly preferably 1 or 2.
[0169] The specific compound is preferably a compound represented by formula (1a). The compound represented by formula (1a) is also the compound of the present invention.
[0170] In formula (1a), A 1a represents a dye skeleton derived from a dye compound selected from a pyrrolopyrrole dye compound, a phthalocyanine dye compound, a squarylium dye compound, an indigo dye compound, a croconium dye compound, an isoindoline dye compound, a quinophthalone dye compound, a diketopyrrolopyrrole dye compound, a triarylmethane dye compound, a xanthene dye compound, a pyrromethene dye compound, a perylene dye compound, an azomethine dye compound, an anthraquinone dye compound, a quinacridone dye compound, a dioxazine dye compound, and a benzofuranone dye compound; L 1a represents a single bond or a divalent linking group; 2a and L 3aeach independently represents a single bond or an alkylene group having 1 to 30 carbon atoms; R 1a represents a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 2a represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent; R 1a and R 2a may be bonded to form a ring, X 1a represents an acid group or a salt thereof; and p represents an integer of 1 to 20.
[0171] A in formula (1a) 1a , L 1a , L 2a , L 3a , R 1a , R 2a , X 1a As for the preferred embodiment of p, A in formula (1) 1 , L 1 , L 2 , L 3 , R 1 , R 2 , X 1 and similar to p.
[0172] The specific compound can be produced by reacting a dye compound with a cyclic ester compound. The dye compound to be reacted with the cyclic ester compound is preferably a dye compound having a hydroxy group. The reaction is preferably carried out under basic conditions by adding an alkaline agent such as potassium carbonate.
[0173] Examples of the dye compound include pyrrolopyrrole dye compounds, phthalocyanine dye compounds, squarylium dye compounds, indigo dye compounds, croconium dye compounds, isoindoline dye compounds, quinophthalone dye compounds, diketopyrrolopyrrole dye compounds, triarylmethane dye compounds, xanthene dye compounds, pyrromethene dye compounds, perylene dye compounds, azomethine dye compounds, anthraquinone dye compounds, quinacridone dye compounds, dioxazine dye compounds, and benzofuranone dye compounds, the details of which are as described above.
[0174] Examples of the cyclic ester compound include a cyclic sulfonate ester, a cyclic ester, etc. Examples of the cyclic sulfonate ester include a compound represented by formula (10b).
[0175] L in formula (10b) 2b represents an alkylene group having 2 to 16 carbon atoms. 2b The upper limit of the number of carbon atoms in the alkylene group represented by is preferably 10 or less, and more preferably 5 or less. 2b The lower limit of the number of carbon atoms of the alkylene group represented by is preferably 3 or more. 2b The alkylene group represented by is preferably a straight chain.
[0176] R in formula (10b) 1b represents a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 2b represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent; R 1b and R 2b may be bonded to form a ring.
[0177] R in formula (10b) 1b and R 2b is R in formula (1). 1 and R 2 The same applies to the preferred range.
[0178] The cyclic sulfonate ester is preferably a compound represented by formula (10c): The compound represented by formula (10c) is also a compound of the present invention.
[0179] In formula (10c), R 10c represents an alkyl group having 9 to 18 carbon atoms, an alkenyl group having 9 to 18 carbon atoms, or an alkynyl group having 9 to 18 carbon atoms, and is preferably an alkyl group having 9 to 18 carbon atoms. 10c The alkyl group represented by R is preferably linear or branched, and more preferably linear. 10cThe alkenyl group represented by R is preferably linear or branched, and more preferably linear. 10c The alkynyl group represented by is preferably linear or branched, more preferably linear.
[0180] The compound represented by formula (10c) can be synthesized, for example, according to the following scheme.
[0181] Specific examples of cyclic sulfonate esters include the compounds shown below. Among the compounds shown below, compounds (Sul-1) to (Sul-9) are compounds represented by formula (10c).
[0182] In one embodiment, a compound represented by formula (1b) can be produced by reacting a dye compound with a compound represented by formula (10b). The dye compound to be reacted with the compound represented by formula (10b) is preferably a dye compound having a hydroxy group. The reaction is preferably carried out under basic conditions by adding an alkaline agent such as potassium carbonate.
[0183]
[0184] In the formula, A 1b represents a dye skeleton derived from a dye compound, and L 1b represents a single bond or a divalent linking group; 2b represents an alkylene group having 2 to 16 carbon atoms; R 1b represents a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 2b represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent; R 1b and R 2b may be bonded to form a ring, X 1b represents a sulfo group or a salt thereof; and p represents an integer of 1 to 20.
[0185] A in the above formula 1b , L 1b , L2b , R 1b , R 2b , X 1b A preferred range of p is 1 , L 1 , L 2 , R 1 , R 2b , X 1b and similar to p.
[0186] Specific examples of the specific compound include compounds SP-1 to SP-42, SB-1, SG-1, SG-2, SIR-1 to SIR-7, SY-1 to SY-7, SR-1 to SR-10, SV-1, and SBk-1 described in the Examples below.
[0187] The content of the specific compound in the total solid content of the composition is preferably 1 to 30% by mass. The upper limit is preferably 20% by mass or less, and more preferably 10% by mass or less. The lower limit is preferably 1.5% by mass or more, and more preferably 2% by mass or more. The content of the specific compound is preferably 5 to 40 parts by mass per 100 parts by mass of the pigment. The upper limit is preferably 35 parts by mass or less, and more preferably 30 parts by mass or less. The lower limit is preferably 10 parts by mass or more, and more preferably 20 parts by mass or more.
[0188] <<Other Pigment Derivatives>> The composition of the present invention may further contain pigment derivatives (also referred to as other pigment derivatives) other than the specific compounds described above. Examples of other pigment derivatives include compounds having a structure in which an acid group, a basic group, or a salt thereof is bound to a colorant skeleton.
[0189] Examples of the dye skeleton include a quinoline dye skeleton, a benzimidazolone dye skeleton, a benzisoindole dye skeleton, a benzothiazole dye skeleton, an iminium dye skeleton, a squarylium dye skeleton, a croconium dye skeleton, an oxonol dye skeleton, a pyrrolopyrrole dye skeleton, a diketopyrrolopyrrole dye skeleton, an azo dye skeleton, an azomethine dye skeleton, a phthalocyanine dye skeleton, an anthraquinone dye skeleton, a quinacridone dye skeleton, a dioxazine dye skeleton, a perinone dye skeleton, a perylene dye skeleton, a thiazineindigo dye skeleton, a thioindigo dye skeleton, an isoindoline dye skeleton, an isoindolinone dye skeleton, a quinophthalone dye skeleton, a dithiol dye skeleton, a triarylmethane dye skeleton, and a pyrromethene dye skeleton.
[0190] Examples of the acid group and salts thereof contained in the other pigment derivatives include a carboxy group, a sulfo group, a phosphoric acid group, a phosphonic acid group, a phosphinic acid group, a boronic acid group, and an imide acid group, and salts thereof. The atoms or atomic groups constituting the salts include alkali metal ions (Li + , Na + , K. + etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ Examples of the imide acid group include an ammonium ion, an imidazolium ion, a pyridinium ion, and a phosphonium ion. 2 NHSO 2 R X1 , -CONHSO 2 R X2 , -CONHCOR X3 or -SO 2 NHCOR X4 A group represented by the formula: 2 NHSO 2 R X1 , -CONHSO 2 R X2 , or -SO 2 NHCOR X4 A group represented by the formula: 2 NHSO 2 R X1 or -CONHSO 2 R X2 is more preferred.X1 ~R X4 R each independently represents an alkyl group or an aryl group. X1 ~R X4 The alkyl group and aryl group represented by R may have a substituent. The substituent is preferably a halogen atom, more preferably a fluorine atom. X1 ~R X4 are each independently preferably an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, and more preferably an alkyl group containing a fluorine atom. The number of carbon atoms in the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. The number of carbon atoms in the aryl group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6.
[0191] Examples of basic groups and salts of other pigment derivatives include amino groups, pyridinyl groups and salts thereof, imidazolyl groups, pyrazolyl groups, salts of ammonium groups, and phthalimidomethyl groups. Examples of atoms or atomic groups that constitute the salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
[0192] The amino group is —NR x11 R x12 and a cyclic amino group.
[0193] -NR x11 R x12 In the group represented by x11 and R x12 are each independently a hydrogen atom, an alkyl group, or an aryl group, and are preferably an alkyl group. That is, the amino group is preferably a dialkylamino group. The alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 5, and even more preferably 1 to 3. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. The alkyl group may have a substituent. The aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 20, and even more preferably 6 to 12. The aryl group may have a substituent.
[0194] Examples of the cyclic amino group include a pyrrolidine group, a piperidine group, a piperazine group, a morpholine group, etc. These groups may further have a substituent.
[0195] The other pigment derivative is also preferably a compound represented by formula (101).
[0196] In formula (101), R 101 and R 102 R each independently represents an alkyl group, an aryl group, or a heteroaryl group; 103 , R 104 , R 105 and R 106 each independently represents a cyano group, an acyl group, an alkoxycarbonyl group, an alkylsulfinyl group, an arylsulfinyl group, or a heteroaryl group; R 107 and R 108 each independently represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, -BR 109 R 110 or a metal atom, R 107 is R 101 , R 103 or R 105 may be covalently or coordinately bonded to R 108 is R 102 , R 104 or R 106 may be covalently or coordinately bonded to R 109 and R 110 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R 109 and R 110 may be bonded to each other to form a ring, 101 represents a single bond, an alkylene group, an arylene group, a nitrogen-containing heterocyclic group, —O—, —S—, —NR′—, —CO—, —COO—, —OCO—, or —SO 2 - or a linking group consisting of a combination thereof, R' represents a hydrogen atom, an alkyl group or an aryl group, X101 represents an acid group, a basic group or a salt thereof, m represents an integer of 1 to 10, n represents an integer of 1 to 10, and when m is 2 or more, a plurality of L 101 and X 101 may be different from each other, and when n is 2 or more, a plurality of X 101 may be different from each other.
[0197] R in formula (101) 101 and R 102 R each independently represents an alkyl group, an aryl group, or a heteroaryl group, preferably an aryl group or a heteroaryl group, and more preferably an aryl group. 101 and R 102 The number of carbon atoms in the alkyl group represented by R is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 10. 101 and R 102 The number of carbon atoms in the aryl group represented by R is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12. 101 and R 102 The number of carbon atoms constituting the ring of the heteroaryl group represented by is preferably 1 to 15, more preferably 1 to 10. The types of heteroatoms constituting the ring of the heteroaryl group include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of heteroatoms constituting the ring of the heteroaryl group is preferably 1 to 3, more preferably 1 or 2. The heteroaryl group is preferably a monocyclic or fused ring, more preferably a monocyclic or fused ring having 2 to 8 rings, and even more preferably a monocyclic or fused ring having 2 to 4 rings. R 101 and R 102 The alkyl group, aryl group and heteroaryl group represented by may be unsubstituted or may have a substituent.
[0198] R in formula (101) 103 and R 105 Preferably, one of R represents a cyano group, an acyl group, an alkoxycarbonyl group, an alkylsulfinyl group, or an arylsulfinyl group, and the other represents a heteroaryl group; 103 and R 105It is more preferable that one of R in formula (101) represents a cyano group and the other represents a heteroaryl group. 104 and R 106 Preferably, one of R represents a cyano group, an acyl group, an alkoxycarbonyl group, an alkylsulfinyl group, or an arylsulfinyl group, and the other represents a heteroaryl group; 104 and R 106 It is more preferred that one of these groups represents a cyano group and the other represents a heteroaryl group.
[0199] R in formula (101) 107 and R 108 Is -BR 109 R 110 It is preferable that R 109 and R 110 R each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group, and is preferably a halogen atom, an alkyl group, an aryl group, or a heteroaryl group, more preferably a halogen atom, an alkyl group, or an aryl group, and even more preferably an aryl group. 109 and R 100 may be bonded to each other to form a ring.
[0200] L in formula (101) 101 represents a single bond, an alkylene group, an arylene group, a nitrogen-containing heterocyclic group, —O—, —S—, —NR′—, —CO—, —COO—, —OCO—, or —SO 2 - or a linking group consisting of a combination thereof, and R' represents a hydrogen atom, an alkyl group, or an aryl group. 101When the linking group is trivalent or higher, it is a group in which one or more hydrogen atoms have been removed from the above-mentioned linking group. The number of carbon atoms in the alkylene group is preferably 1 to 30, and more preferably 1 to 15. The alkylene group may have a substituent. Examples of the substituent include the groups exemplified for the substituent T above. The number of carbon atoms in the arylene group is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10, with a phenylene group being particularly preferred. The nitrogen-containing heterocyclic group is preferably a 5-membered or 6-membered ring. The nitrogen-containing heterocyclic group is preferably a monocyclic ring or a fused ring, more preferably a monocyclic ring or a fused ring having 2 to 8 rings, and even more preferably a monocyclic ring or a fused ring having 2 to 4 rings. The number of nitrogen atoms contained in the nitrogen-containing heterocyclic group is preferably 1 to 3, and more preferably 1 or 2. The nitrogen-containing heterocyclic group may contain a heteroatom other than a nitrogen atom. Examples of heteroatoms other than a nitrogen atom include an oxygen atom and a sulfur atom. The number of heteroatoms other than nitrogen atoms is preferably 0 to 3, more preferably 0 to 1. Specific examples of the nitrogen-containing heterocyclic group include the nitrogen-containing heterocyclic groups described in paragraph 0067 of WO 2017 / 146092.
[0201] L 101 Specific examples of the linking group represented by include groups described in paragraph 0068 of WO 2017 / 146092, and groups formed by combining -O-, an alkylene group, and an arylene group (such as -O-alkylene group-arylene group-).
[0202] X in formula (101) 101 represents an acid group, a basic group, or a salt thereof. Details of these groups are as described above.
[0203] In formula (101), m represents an integer of 1 to 10, preferably 1 to 4, more preferably 1 to 3, still more preferably 1 or 2, and particularly preferably 2. In formula (101), n represents an integer of 1 to 10, preferably 1 to 4, more preferably 1 to 3, still more preferably 1 or 2, and particularly preferably 1.
[0204] In formula (101), R 101 ~R 108 At least one of them is "-L 101 -(X 101)n” and R 101 and R 108 At least one of them is "-L 101 -(X 101 )n” and R 101 and R 108 "-L 101 -(X 101 )n”.
[0205] The compound represented by formula (101) is preferably a compound represented by formula (102). In formula (102), R 103 , R 104 , R 105 and R 106 each independently represents a cyano group, an acyl group, an alkoxycarbonyl group, an alkylsulfinyl group, an arylsulfinyl group, or a heteroaryl group; R 107 and R 108 each independently represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, -BR 109 R 100 or a metal atom, R 107 is R 103 or R 105 may be covalently or coordinately bonded to R 108 is R 104 or R 106 may be covalently or coordinately bonded to R 109 and R 100 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, or a heteroaryloxy group; R 109 and R 100 may be bonded to each other to form a ring, 102 and L 103 each independently represents a single bond, an alkylene group, an arylene group, a nitrogen-containing heterocyclic group, —O—, —S—, —NR′—, —CO—, or —SO 2- or a linking group consisting of a combination thereof, R' represents a hydrogen atom, an alkyl group or an aryl group, X 102 and X 103 each independently represents an acid group, a basic group, or a salt thereof; n2 and n3 each independently represent 0 to 4, and at least one of n2 and n3 is 1 or greater.
[0206] R in formula (102) 103 ~R 108 is R in formula (101). 103 ~R 108 The same definition and preferred range are also the same. 102 and X 103 is X in formula (101). 101 The same applies to the preferred range.
[0207] L in formula (102) 102 and L 103 The linking group represented by is L in formula (101). 101 Examples of the linking groups include those described above.
[0208] L in formula (102) 102 and L 103 is a benzene ring directly connected to the pyrrolopyrrole structure, which is the core structure of the pigment derivative, and X 102 and X 103 The number of atoms constituting the chain connecting the two is preferably 1 to 20. The lower limit is preferably 2 or more, more preferably 3 or more. The upper limit is preferably 18 or less, more preferably 15 or less.
[0209] Specific examples of the compound represented by formula (101) include compounds sa-1 to sa-23 described in the Examples below.
[0210] Specific examples of other pigment derivatives include the compounds described in paragraph 0124 of WO 2022 / 085485, the benzimidazolone compounds or salts thereof described in JP 2018-168244 A, compounds having an isoindoline skeleton described in general formula (1) of Japanese Patent No. 6996282 A, compounds described in JP 2019-172968 A, and compounds described in Chinese Patent Application Publication No. 115124889 A.
[0211] The content of the other pigment derivative is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 10 parts by mass or less, relative to 100 parts by mass of the specific compound.
[0212] <<Resin>> The composition of the present invention contains a resin. The resin is blended, for example, to disperse pigments and the like in the composition or as a binder. Resins used primarily to disperse pigments and the like in the composition are also called dispersants. However, these uses of resins are merely examples, and resins can also be used for purposes other than these uses.
[0213] The weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000. The upper limit is preferably 1,000,000 or less, and more preferably 500,000 or less. The lower limit is preferably 4,000 or more, and more preferably 5,000 or more.
[0214] Examples of resins include (meth)acrylic resins, polyimine resins, epoxy resins, (meth)acrylamide resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, siloxane resins, and urethane resins.
[0215] Further, as the resin, a resin described in paragraphs 0091 to 0099 of WO 2022 / 065215, a blocked polyisocyanate resin described in JP 2016-222891 A, a resin described in JP 2020-122052 A, a resin described in JP 2020-111656 A, a resin described in JP 2020-139021 A, a resin described in JP 2017-138503 A Resins containing a structural unit having a ring structure in the main chain and a structural unit having a biphenyl group in the side chain, resins described in paragraphs
[0199] to
[0233] of JP2020-186373A, alkali-soluble resins described in JP2020-186325A, resins represented by formula 1 described in Korean Patent Publication No. 10-2020-0078339A, and copolymers containing epoxy groups and acid groups described in WO2022 / 030445A. , Resins described in JP 2018-135514 A, Copolymers described in JP 2020-041046 A, Resins described in JP 2023-033156 A, Resins described in JP 2023-030386 A, Resins described in JP 2023-027753 A, Resins described in JP 2020-139021 A, Resins described in JP 2023-074038 A, Resins described in JP 2023-079666 A The resins described in the publication, the cardo resins described in Chinese Patent Application Publication No. 115947929, the copolymers described in JP-A-2024-014141, the resins described in JP-A-2024-050148, the copolymers described in WO 2024 / 134926, the resins described in JP-A-2024-088596, and the compounds represented by formula (1) described in JP-A-2024-128953 can also be used.
[0216] (Specific Resin (Resin Having Amine Value)) The composition of the present invention contains a resin having an amine value (hereinafter also referred to as specific resin) as a resin. The amine value of the specific resin is preferably 10 to 150 mgKOH / g. The upper limit is preferably 140 mgKOH / g or less, and more preferably 130 mgKOH / g or less. The lower limit is preferably 15 mgKOH / g or more, and more preferably 20 mgKOH / g or more.
[0217] Examples of resins having an amine value include resins having an amino group, etc. The amino group may be contained in the main chain of the repeating unit or may be present on a side chain.
[0218] The specific resin may have an acid group. Examples of the acid group include a carboxy group, a phosphate group, a sulfo group, and a phenolic hydroxy group, with a carboxy group being preferred. When the specific resin has an acid group, the acid value of the specific resin is preferably 10 to 150 mgKOH / g. The upper limit is preferably 140 mgKOH / g or less, and more preferably 130 mgKOH / g or less. The lower limit is preferably 15 mgKOH / g or more, and more preferably 20 mgKOH / g or more. Furthermore, the ratio of the amine value to the acid value of the specific resin is preferably 1:3 to 0.1, more preferably 1:2.5 to 0.25, and even more preferably 1:2 to 0.5.
[0219] The weight average molecular weight of the specific resin is preferably 5,000 to 100,000, and more preferably 5,000 to 50,000.
[0220] Examples of the specific resin include (meth)acrylic resin, polyimine resin, polyester resin, polyether resin, and polyamide resin, and the specific resin is preferably a (meth)acrylic resin or a polyimine resin.
[0221] The specific resin is preferably a graft resin. Examples of graft resins include resins having a repeating unit with a graft chain. In this specification, the term "graft chain" refers to a polymer chain that branches off from the main chain of the repeating unit. The graft chain preferably has 40 to 10,000 atoms excluding hydrogen atoms, more preferably 50 to 2,000 atoms excluding hydrogen atoms, and even more preferably 60 to 500 atoms excluding hydrogen atoms.
[0222] The graft chain preferably contains a repeating unit of at least one structure selected from the group consisting of a polyester structure, a polyether structure, a poly(meth)acrylic structure, a polystyrene structure, a polyurethane structure, a polyurea structure, and a polyamide structure, more preferably contains a repeating unit of at least one structure selected from the group consisting of a polyester structure, a polyether structure, a poly(meth)acrylic structure, and a polystyrene structure, even more preferably contains a repeating unit of at least one structure selected from the group consisting of a polyester structure, a polyether structure, and a poly(meth)acrylic structure, still more preferably contains a repeating unit of a polyester structure or a polyether structure, and particularly preferably contains a repeating unit of a polyester structure.
[0223] The specific resin is also preferably a polyimine resin containing a nitrogen atom in at least one of the main chain and the side chain. The polyimine resin is preferably a resin having a main chain with a partial structure having a functional group with a pKa of 14 or less and a side chain having 40 to 10,000 atoms, and having a basic nitrogen atom in at least one of the main chain and the side chain. There are no particular restrictions on the basic nitrogen atom, as long as it is a nitrogen atom that exhibits basicity. For details on polyimine resins, please refer to the descriptions in paragraphs 0102 to 0166 of JP 2012-255128 A.
[0224] Commercially available specific resins include DISPERBYK161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, and BYK-LPN6919 (all manufactured by BYK Japan), and SOLSPERSE112. 00, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (all manufactured by Lubrizol Japan Corporation), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), and the like.
[0225] (Other Resins) The composition of the present invention may further contain a resin that does not have an amine value (hereinafter also referred to as "other resins").
[0226] As the other resin, it is preferable to use a resin that does not have an amine value and has an acid group (hereinafter also referred to as a specific acidic resin). Examples of the acid group include a carboxy group, a phosphate group, a sulfo group, and a phenolic hydroxy group.
[0227] The acid value of the specific acidic resin is preferably 30 to 500 mgKOH / g. The lower limit is preferably 40 mgKOH / g or more, and more preferably 50 mgKOH / g or more. The upper limit is preferably 400 mgKOH / g or less, more preferably 300 mgKOH / g or less, and even more preferably 200 mgKOH / g or less. The weight average molecular weight (Mw) of the specific acidic resin is preferably 5,000 to 100,000, and more preferably 5,000 to 50,000. The number average molecular weight (Mn) of the specific acidic resin is preferably 1,000 to 20,000.
[0228] The specific acidic resin preferably contains a repeating unit having an acid group on the side chain, and more preferably contains 5 to 70 mol% of the repeating units having an acid group on the side chain based on all repeating units of the resin. The upper limit of the content of repeating units having an acid group on the side chain is preferably 50 mol% or less, more preferably 30 mol% or less. The lower limit of the content of repeating units having an acid group on the side chain is preferably 10 mol% or more, more preferably 20 mol% or more.
[0229] For details of the specific acidic resin, please refer to paragraphs
[0558] to
[0571] of JP 2012-208494 A (corresponding paragraphs
[0685] to
[0700] of U.S. Patent Application Publication No. 2012 / 0235099 A) and paragraphs
[0076] to
[0099] of JP 2012-198408 A, the contents of which are incorporated herein by reference. Furthermore, commercially available products can also be used as the specific acidic resin. Furthermore, there are no particular limitations on the method for introducing acid groups into the resin, and examples include the method described in Japanese Patent No. 6,349,629 A. Furthermore, examples of methods for introducing acid groups into the resin include a method in which an acid anhydride is reacted with a hydroxy group generated by a ring-opening reaction of an epoxy group to introduce the acid group.
[0230] As the specific acidic resin, it is also preferable to use a resin having an aromatic carboxy group. In a resin having an aromatic carboxy group, the aromatic carboxy group may be contained in the main chain of the repeating unit or may be contained in a side chain of the repeating unit. The aromatic carboxy group is preferably contained in the main chain of the repeating unit. In this specification, an aromatic carboxy group refers to a group having a structure in which one or more carboxy groups are bonded to an aromatic ring. In the aromatic carboxy group, the number of carboxy groups bonded to the aromatic ring is preferably 1 to 4, and more preferably 1 to 2. Examples of resins having an aromatic carboxy group include the resins described in paragraphs 0082 to 0107 of WO 2021 / 166858.
[0231] As the other resin, it is also preferable to use a resin having a polymerizable group. Examples of the polymerizable group include an ethylenically unsaturated bond-containing group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, an allyl group, a (meth)acryloyl group, and a styrene group.
[0232] As the other resin, a resin used as a dispersant can also be used. The resin used as a dispersant is preferably a graft resin. The resin used as a dispersant is also preferably a resin having an aromatic carboxy group. The resin used as a dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to a core portion. Examples of such resins include dendrimers (including star-shaped polymers). Specific examples of dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP 2013-043962 A.
[0233] The resin used as a dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in a side chain. The content of the repeating unit having an ethylenically unsaturated bond-containing group in a side chain is preferably 10 mol % or more, more preferably 10 to 80 mol %, and even more preferably 20 to 70 mol %, of all repeating units of the resin.
[0234] Dispersants are also available as commercially available products, and specific examples thereof include the DISPERBYK series manufactured by BYK Chemie, the SOLSPERSE series manufactured by Lubrizol Japan, the Efka series manufactured by BASF, and the AJISPER series manufactured by Ajinomoto Fine-Techno Co., Ltd. In addition, the products described in paragraph 0129 of JP 2012-137564 A and the products described in paragraph 0235 of JP 2017-194662 A can also be used as dispersants.
[0235] The resin content of the total solid content of the composition is preferably 1 to 50% by mass, with the upper limit being preferably 40% by mass or less, and more preferably 30% by mass or less, and the lower limit being preferably 5% by mass or more, and more preferably 10% by mass or more.
[0236] The content of the specific resin in the resin is preferably 5% by mass or more, more preferably 8% by mass or more, and even more preferably 10% by mass or more. The upper limit can be 100% by mass, or can be 80% by mass or less, or can be 60% by mass or less. The content of the specific resin is preferably 40 to 1,000 parts by mass per 100 parts by mass of the specific compound described above. The upper limit is preferably 45 parts by mass or less, and more preferably 50 parts by mass or less. The lower limit is preferably 950 parts by mass or more, and more preferably 900 parts by mass or more.
[0237] A preferred embodiment of the composition of the present invention includes, as the resin, the above-mentioned specific resin (a resin having an amine value) and the above-mentioned specific acidic resin (a resin having no amine value and an acid value). The content of the specific acidic resin is preferably 0 to 1900 parts by mass per 100 parts by mass of the specific resin. The upper limit is preferably 1500 parts by mass or less, and more preferably 1000 parts by mass or less. The lower limit is preferably 0 parts by mass or more, and more preferably 25 parts by mass or more.
[0238] The composition of the present invention may contain only one type of resin or two or more types. When two or more types of resins are contained, the total amount thereof is preferably within the above range.
[0239] <<Solvent>> The composition of the present invention contains a solvent. Examples of the solvent include organic solvents. The type of solvent is basically not particularly limited as long as the solubility of each component and the coatability of the composition are satisfied. Examples of organic solvents include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents. For details of these, please refer to paragraph
[0223] of WO 2015 / 166779, the contents of which are incorporated herein by reference. Furthermore, ester-based solvents substituted with a cyclic alkyl group and ketone-based solvents substituted with a cyclic alkyl group can also be preferably used. Specific examples of organic solvents include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, cyclopentyl methyl ether, dipropylene glycol monomethyl ether, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, ethyl carbitol acetate, and butyl carbitol acetate. acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, propylene glycol diacetate, 3-methoxybutanol, methyl ethyl ketone, gamma butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, butane-1,3-diyl diacetate, dipropylene glycol methyl ether acetate, diacetone alcohol (also known as diacetone alcohol, 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, isopropyl alcohol, 2-butanol, and the like.However, it may be preferable to reduce the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) used as organic solvents for environmental reasons (for example, the amount may be 50 ppm by mass (parts per million) or less, 10 ppm by mass or less, or 1 ppm by mass or less, relative to the total amount of organic solvents).
[0240] The organic solvent may be used alone or in combination of two or more. When two or more organic solvents are used, a main solvent occupies 50% by mass or more of the organic solvent, and an auxiliary solvent occupies 50% by mass or less. The main solvent preferably accounts for 60% by mass or more of the organic solvent, more preferably 70% by mass or more. Two or more auxiliary solvents may be contained, and the total amount thereof is preferably 40% by mass or less, more preferably 30% by mass or less. The type of main solvent is not particularly limited, and preferred examples include the preferred solvents described in paragraph 0224 of WO 2015 / 166779, ester solvents substituted with a cyclic alkyl group, and ketone solvents substituted with a cyclic alkyl group. The type of auxiliary solvent is not particularly limited, and is selected from the solvents described above.
[0241] The metal content of the organic solvent is preferably low. The metal content of the organic solvent is preferably, for example, 10 parts per billion (ppb) by mass or less. If necessary, an organic solvent having a metal content of ppt (parts per trillion) by mass may be used, and such an organic solvent is provided, for example, by Toyo Gosei Co., Ltd. (The Chemical Daily, November 13, 2015).
[0242] Methods for removing impurities such as metals from organic solvents include, for example, distillation (molecular distillation, thin-film distillation, etc.) and filtration using a filter. The pore size of the filter used for filtration is preferably 10 μm or less, more preferably 5 μm or less, and even more preferably 3 μm or less. The filter material is preferably polytetrafluoroethylene, polyethylene, or nylon.
[0243] The organic solvent may contain isomers (compounds having the same number of atoms but different structures). The organic solvent may contain only one type of isomer or multiple types of isomers.
[0244] The organic solvent preferably has a peroxide content of 0.8 mmol / L or less, and more preferably contains substantially no peroxide.
[0245] The content of the solvent in the composition is preferably 10 to 97% by mass. The lower limit is preferably 30% by mass or more, more preferably 40% by mass or more, even more preferably 50% by mass or more, still more preferably 60% by mass or more, and particularly preferably 70% by mass or more. The upper limit is preferably 96% by mass or less, more preferably 95% by mass or less. The composition may contain only one type of solvent, or may contain two or more types. When two or more types are contained, the total amount thereof is preferably within the above range.
[0246] <<Polymerizable Compound>> The composition of the present invention may contain a polymerizable compound. Examples of the polymerizable compound include a compound having an ethylenically unsaturated bond-containing group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, an allyl group, a (meth)acryloyl group, and a styrene group. The polymerizable compound used in the present invention is preferably a radically polymerizable compound.
[0247] The polymerizable compound is preferably a monomer. The molecular weight of the polymerizable compound is preferably 100 to 2500. The upper limit is preferably 2000 or less, more preferably 1500 or less. The lower limit is preferably 150 or more, more preferably 250 or more.
[0248] The polymerizable compound is preferably a compound containing two or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 2 to 15 ethylenically unsaturated bond-containing groups, and even more preferably a compound containing 2 to 6 ethylenically unsaturated bond-containing groups. Furthermore, the polymerizable compound is preferably a difunctional to 15-functional (meth)acrylate compound, and more preferably a difunctional to hexafunctional (meth)acrylate compound. Specific examples of the polymerizable compound include the compounds described in paragraphs 0075 to 0083 of WO 2022 / 065215 and the compounds described in Taiwan Patent Application Publication No. 201832008.
[0249] Preferred polymerizable compounds include dipentaerythritol tri(meth)acrylate (commercially available product: KAYARAD D-330, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available product: KAYARAD D-320, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available product: KAYARAD D-310, manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available products: KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd., and NK Ester A-DPH-12E, manufactured by Shin-Nakamura Chemical Co., Ltd.), and compounds having a structure in which the (meth)acryloyl group is bonded via an ethylene glycol and / or propylene glycol residue (e.g., SR454, SR499, commercially available from Sartomer). Furthermore, as the polymerizable compound, diglycerin EO (ethylene oxide) modified (meth)acrylate (commercially available product is M-460;Toagosei), pentaerythritol tetraacrylate (Shin-Nakamura Chemical Co., Ltd., NK Ester A-TMMT), 1,6-hexanediol diacrylate (Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (Nippon Kayaku Co., Ltd.), Aronix TO-2349 (Toagosei Co., Ltd.), NK Oligo UA-7200 (Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (Kyoeisha Chemical Co., Ltd.), 8UH-1 006, 8UH-1012 (all manufactured by Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), Aronix MT-3041, 3042 (manufactured by Toagosei Co., Ltd., polymerizable compounds containing amines), Aronix M-510, 520 (manufactured by Toagosei Co., Ltd., polymerizable compounds having an acidic group), Etercure 6361-100 (Eternal Materials, polymerizable compound having a hyperbranched structure), EBECRYL80 (tetrafunctional monomer containing amine, manufactured by Daicel-Olknes Co., Ltd.), EBECRYL7100 (bifunctional monomer containing amine, manufactured by Daicel-Olknes Co., Ltd.), CN371NS (bifunctional monomer containing amine, manufactured by Arkema), HOA-MPL (2-acryloyloxyethyl-phthalic acid: manufactured by Kyoeisha Chemical Co., Ltd.), HOA-MPE (2-acryloyloxyethyl-2-hydroxyethyl-phthalic acid: manufactured by Kyoeisha Chemical Co., Ltd.), dendrimer structures described in JP 2023-043479 A Polymerizable compounds having a branched or hyperbranched structure, polymerizable compounds described in JP-T-2023-529984, polymerizable compounds described in WO 2023 / 190562, (meth)acrylate compounds described in JP-A-2023-173204, polymerizable compounds containing a urethane bond described in JP-A-2024-070237, EBECRYL 5129 (manufactured by Daicel-Allnex Co., Ltd.), EBECRYL 220 (manufactured by Daicel-Allnex Co., Ltd.), KUA-9N (manufactured by KSM Co., Ltd.), polymerizable compounds described in JP-A-2024-085753, and the like can also be used;
[0250] As the polymerizable compound, a polymerizable compound having a fluorene skeleton can also be used. The polymerizable compound having a fluorene skeleton is preferably a bifunctional polymerizable compound. Commercially available polymerizable compounds having a fluorene skeleton include OGSOL EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomers having a fluorene skeleton).
[0251] The content of the polymerizable compound in the total solid content of the composition is preferably 1 to 30% by mass. The upper limit is preferably 20% by mass or less, more preferably 15% by mass or less. The lower limit is preferably 3% by mass or more, more preferably 5% by mass or more. Only one type of polymerizable compound may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is in the above range.
[0252] <<Photopolymerization initiator>> The composition of the present invention may contain a photopolymerization initiator. When the composition of the present invention contains a polymerizable compound, it is preferable that the composition of the present invention further contains a photopolymerization initiator. The photopolymerization initiator is preferably a photoradical polymerization initiator.
[0253] Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, α-hydroxyketone compounds, α-aminoketone compounds, and glyoxylate compounds. The photopolymerization initiator is preferably a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an α-hydroxyketone compound, an α-aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a hexaarylbiimidazole compound, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound, a glyoxylate compound, or a 3-aryl-substituted coumarin compound, more preferably an oxime compound, an α-hydroxyketone compound, an α-aminoketone compound, a glyoxylate compound, or an acylphosphine compound, still more preferably an α-aminoketone compound, a glyoxylate compound, or an oxime compound, and particularly preferably an oxime compound.
[0254] Examples of the photopolymerization initiator include the compounds described in paragraphs 0065 to 0111 of JP-A No. 2014-130173, the compounds described in Japanese Patent No. 6301489, and the compounds described in MATERIAL STAGE 37-60pp, vol. 19, No. peroxide-based photopolymerization initiators described in JP-A-2019-3, 2019, photopolymerization initiators described in WO 2018 / 221177, photopolymerization initiators described in WO 2018 / 110179, photopolymerization initiators described in JP-A-2019-043864, photopolymerization initiators described in JP-A-2019-044030, peroxide-based initiators described in JP-A-2019-167313, aminoacetophenone-based initiators having an oxazolidine group described in JP-A-2020-055992, Oxime-based photopolymerization initiators described in JP-A-2020-190459, polymers described in JP-A-2020-172619, compounds represented by formula 1 described in WO 2020 / 152120, compounds described in JP-A-2021-181406, photopolymerization initiators described in JP-A-2022-013379, compounds represented by formula (1) described in JP-A-2022-015747, fluorine-containing fluorene oxime ester-based photoinitiators described in JP-T-2021-507058, Chinese Patent Application Publication No. 11 Initiators described in Patent Publication No. 0764367, initiators described in JP-T-2022-518535, initiators described in WO 2021 / 175855, compounds described in Taiwan Patent Application Publication No. 202200534, compounds described in JP-A-2022-078550, compounds described in Korean Patent Publication No. 10-2017-0087330, compounds described in WO 2022 / 075452, oxime ester compounds described in Chinese Patent Application Publication No. 110066225, Compounds described in Japanese Patent Application Laid-Open No. 10-2022-0076157, compounds having a triarylamine or N-arylcarbazole skeleton described in paragraphs 0042 to 0062 of International Publication No. 2019 / 013112, oxime ester-based photopolymerization initiators described in Japanese Patent Application Laid-Open No. 7219378, photopolymerization initiators described in Korean Patent Publication No. 10-2021-0146174, photopolymerization initiators described in International Publication No. 2019 / 013112, photopolymerization initiators described in JP-A No. 2023-033731,Initiators described in JP-T-2022-515524, initiators described in JP-T-2023-517304, initiators described in Chinese Patent Application Publication No. 114149517, aminoketone compounds described in Chinese Patent Application Publication No. 115925596, compounds described in JP-A-2023-159489, compounds described in JP-A-2023-159487, compounds described in Taiwan Patent Application Publication No. Compounds described in Patent Publication No. 02336003, compounds described in Chinese Patent Application Publication No. 113527138, organosilicon compounds described in JP-T-2022-502526, oxime compounds described in Korean Patent Publication No. 10-2017-0009794, photopolymerization initiators described in Korean Patent Publication No. 10-2023-0033862, oxime compounds described in Japanese Patent Publication No. 2019-519518 oxime ester compounds, multifunctional polymer photopolymerization initiators described in JP-T-2024-517534, photopolymerization initiators described in WO 2024 / 085227, compounds described in JP-T-2024-521379, photopolymerization initiators described in JP-T-2024-523053, oxime ester initiators described in Chinese Patent Application Publication No. 117510396, Chinese Patent Application Publication No. 111 Examples of such an initiator include the oxime compounds described in JP-A-2024-124479, the photopolymerization initiators described in JP-A-2024-537185, the photopolymerization initiators described in JP-A-2024-535245, the aminoketone compounds described in JP-A-2024-534719, and the oxime ester compounds described in JP-A-2024-149305.
[0255] Specific examples of hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole.
[0256] Commercially available α-hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, and Omnirad 127 (all manufactured by IGM Resins B.V.), and Irgacure 184, Irgacure 1173, Irgacure 2959, and Irgacure 127 (all manufactured by BASF). Commercially available α-aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (all manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (all manufactured by BASF), etc. Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (all manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (all manufactured by BASF), etc. Commercially available glyoxylate compounds include Esacure 563 (manufactured by IGM Resins B.V.).
[0257] Examples of the oxime compound include the compounds described in paragraph 0142 of WO 2022 / 085485, the compounds described in Japanese Patent No. 5430746, the compounds described in Japanese Patent No. 5647738, the compounds represented by the general formula (1) of JP-A-2021-173858, and the compounds described in paragraphs 0022 to 0024, and the compounds represented by the general formula (1) of JP-A-2021-170089 and the compounds described in paragraphs 0117 to 0120. Specific examples of the oxime compound include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime), and the like. Commercially available products include Irgacure OXE01, Irgacure OXE02, Irgacure OXE03, Irgacure OXE04, Irgacure OXE05 (all manufactured by BASF), TR-PBG-301, TR-PBG-304, TR-PBG-305, TR-PBG-309, TR-PBG-3054, TR-PBG-3057, TR-PBG-314, TR-PBG-327, TR-PBG-345, TR-PBG-346, TR- Examples of the oxime compound include PBG-358, TR-PBG-365, TR-PBG-380, TR-PBG-610, TR-PBG-A, and TR-PBG-B (all manufactured by TRONLY Corporation), and ADEKA OPTOMER N-1919 (manufactured by ADEKA Corporation; photopolymerization initiator 2 described in JP 2012-014052 A). In addition, it is also preferable to use, as the oxime compound, a compound that is not colorable or a compound that is highly transparent and does not easily discolor. Commercially available products include ADEKA ARCLES NCI-730, NCI-831, NCI-831E, and NCI-930 (all manufactured by ADEKA Corporation).
[0258] As the photopolymerization initiator, an oxime compound having a fluorene ring, an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is replaced with a naphthalene ring, an oxime compound having a fluorine atom, an oxime compound having a nitro group, an oxime compound having a benzofuran skeleton, an oxime compound in which a substituent having a hydroxy group is bonded to a carbazole skeleton, or a compound described in paragraphs 0143 to 0149 of WO 2022 / 085485 can also be used.
[0259] As the photopolymerization initiator, a compound represented by formula (OX-1) can also be used.
[0260] In formula (OX-1), X 1a represents a divalent linking group containing at least one ring selected from the group consisting of an aromatic ring and a heterocyclic ring; 1a represents a hydrogen atom or an acyl group; R 2a represents an alkyl group or an aryl group; R 3a and R 4a each independently represents a hydrogen atom or an alkyl group; Alk 1 and Alk 2 each independently represents an alkyl group; R 3a and R 4a may be bonded to form a ring, Alk 1 and Alk 2 may be bonded to form a ring, and n represents 0 or 1.
[0261] X in formula (OX-1) 1a Examples of the divalent linking group represented by include a divalent aromatic ring group, a divalent heterocyclic group, a divalent group in which two or more aromatic ring groups are bonded together via a single bond or a linking group, a divalent group in which two or more heterocyclic groups are bonded together via a single bond or a linking group, and a divalent group in which an aromatic ring group and a heterocyclic group are bonded together via a single bond or a linking group. Examples of the linking group that bonds the above-mentioned aromatic ring groups together, heterocyclic groups together, or an aromatic ring group and a heterocyclic group include -CH 2 -, -O-, -CO-, -S-, -NR x - and groups combining these. xrepresents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heterocyclic group.
[0262] X in formula (OX-1) 1a is preferably a group represented by any one of formulas (X-1) to (X-13), more preferably a group represented by formula (X-1), formula (X-2), formula (X-4), formula (X-6) or formula (X-8), and further preferably a group represented by formula (X-2) or formula (X-6).
[0263] In the formula R X1 ~R X9 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group, and * represents a bond.
[0264] R X1 ~R X9 The number of carbon atoms in the alkyl group represented by is preferably 1 to 15, and more preferably 1 to 10. The alkyl group may be linear, branched, or cyclic. The alkyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heteroaryl group.
[0265] R X1 ~R X9 The number of carbon atoms in the alkenyl group represented by is preferably 2 to 15, and more preferably 2 to 10. The alkenyl group may be linear, branched, or cyclic. The alkenyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heteroaryl group.
[0266] R X1 ~R X9 The number of carbon atoms in the alkynyl group represented by is preferably 2 to 15, and more preferably 2 to 10. The alkynyl group may be linear, branched, or cyclic. The alkynyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heteroaryl group.
[0267] R X1 ~R X9The number of carbon atoms in the aryl group represented by is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6. The aryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and a heteroaryl group.
[0268] R X1 ~R X9 The heteroaryl group represented by is preferably a 5-membered or 6-membered ring. The heteroatoms contained in the heteroaryl group are preferably oxygen atoms, nitrogen atoms, and sulfur atoms. The number of heteroatoms contained in the heteroaryl group is preferably 1 to 3. The heteroaryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and an aryl group.
[0269] R in formula (OX-1) 1a represents a hydrogen atom or an acyl group, and is preferably an acyl group.
[0270] R in formula (OX-1) 2a represents an alkyl group or an aryl group, and is preferably an alkyl group because the reactivity of the generated radical is high. 2a The number of carbon atoms in the alkyl group represented by is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. The alkyl group may have a substituent, but is preferably an unsubstituted alkyl group. R 2a The alkyl group represented by R is preferably an unsubstituted linear or branched alkyl group, and more preferably an unsubstituted linear alkyl group. 2a The number of carbon atoms in the aryl group represented by is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6. The aryl group may have a substituent, but is preferably an unsubstituted aryl group.
[0271] R in formula (OX-1) 3a and R 4aR each independently represents a hydrogen atom or an alkyl group, and is preferably a hydrogen atom. 3a and R 4a The number of carbon atoms in the alkyl group represented by is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. The alkyl group may have a substituent, but is preferably an unsubstituted alkyl group. R 3a and R 4a may be bonded to form a ring. The ring formed is preferably a 5- or 6-membered ring, and more preferably a 5- or 6-membered aliphatic hydrocarbon ring.
[0272] Alk of formula (OX-1) 1 and Alk 2 each independently represents an alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. The alkyl group may have a substituent, but is preferably an unsubstituted alkyl group. Alk 1 and Alk 2 may be bonded to form a ring, and preferably form a ring. The ring formed is preferably a 5- or 6-membered ring, more preferably a 5- or 6-membered aliphatic hydrocarbon ring, and more preferably a cyclopentane ring or a cyclohexane ring.
[0273] In formula (OX-1), n represents 0 or 1, and is preferably 0.
[0274] Specific examples of the compound represented by formula (OX-1) include the compounds described in paragraphs 0092 to 0096 of JP-A No. 2012-113104 and the compound described in paragraph 0041 of JP-A No. 2012-189997.
[0275] As the photopolymerization initiator, a compound represented by formula (OX-2) can also be used.
[0276]
[0277] In formula (OX-2), R 1b and R 2b each independently represents a substituent, R 3b ~R 7b each independently represents a hydrogen atom or a substituent, Ar 1b represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent; n represents 0 or 1;
[0278] R 1b and R 2b Examples of the substituent represented by include an alkyl group and an aryl group, and an alkyl group is preferred. The alkyl group preferably has 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms. The alkyl group may be linear, branched, or cyclic. The alkyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, an alkenyl group, an alkynyl group, and a heteroaryl group. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, even more preferably 6 to 10 carbon atoms, and particularly preferably 6 carbon atoms. The aryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and a heteroaryl group.
[0279] R 3b ~R 7b Examples of the substituent represented by R include a halogen atom, an alkyl group, and an aryl group. Examples of the alkyl group and the aryl group include those described above. 3b ~R 7b is preferably a hydrogen atom.
[0280] Ar 1b represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, Ar 1bis preferably an aryl group which may have a substituent. The number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6. Examples of the substituent include a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkylthio group, an arylthio group, a nitro group, and an acyl group, and an acyl group is preferred.
[0281] As the photopolymerization initiator, a compound represented by formula (OX-3) can also be used.
[0282]
[0283] In formula (OX-3), Ar 1c represents a (k+m+1)-valent aromatic ring group or a (k+m+1)-valent heterocyclic group; Ar 2c represents a (k+2)-valent aromatic ring group or a (k+2)-valent heterocyclic group; R 1c ~R 3c each independently represents a substituent; 1c is a single bond or CR 11c R 12c represents R 11c and R 12c each independently represents a hydrogen atom, an alkyl group, or an aryl group; 1c Ha-CH 2 represents -, -N-, -O- or -S-; k represents 0 or 1; m represents an integer of 0 to 4; and n represents 0 or 1.
[0284] R 1c and R 2cExamples of the substituent represented by include an alkyl group and an aryl group, and an alkyl group is preferred. The alkyl group preferably has 1 to 15 carbon atoms, and more preferably 1 to 10 carbon atoms. The alkyl group may be linear, branched, or cyclic. The alkyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, an alkenyl group, an alkynyl group, and a heteroaryl group. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms, even more preferably 6 to 10 carbon atoms, and particularly preferably 6 carbon atoms. The aryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and a heteroaryl group. R 2c is preferably an alkyl group having a branched or cyclic structure.
[0285] R 3c Examples of the substituent represented by include a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group and an acyl group, and an acyl group is preferred.
[0286] L 1c is a single bond or CR 11c R 12c represents R 11c and R 12c R each independently represents a hydrogen atom, an alkyl group, or an aryl group. 11c and R 12c The alkyl group and aryl group in R 1c and R 2c When k is 1, L 1c is preferably a single bond.
[0287] X 1c is -CH 2 It represents -, -N-, -O- or -S-, and is preferably -O- or -S-.
[0288] Ar 1crepresents a (k+m+1)-valent aromatic ring group or a (k+m+1)-valent heterocyclic group, and is preferably a (k+m+1)-valent aromatic ring group. The aromatic ring group is preferably a benzene ring group or a naphthalene ring group, and more preferably a benzene ring group.
[0289] Ar 2c represents a (k+2)-valent aromatic ring group or a (k+2)-valent heterocyclic group, and is preferably a (k+2)-valent aromatic ring group. The aromatic ring group is preferably a benzene ring group or a naphthalene ring group, and more preferably a benzene ring group.
[0290] k represents 0 or 1, and is preferably 0. m represents an integer of 0 to 4, and is preferably 0 or 1, and more preferably 1. n represents 0 or 1, and is preferably 0.
[0291] As the photopolymerization initiator, a ketoxime ester compound having an aryloxy group at the ortho position, represented by formula (OX-4), can also be suitably used. Examples of such compounds include the compounds described in Chinese Patent Application Publication No. 117342977.
[0292] In formula (OX-4), R 1d and R 2d each independently represents an alkyl group, an aryl group, or a heterocyclic group; R 3d , R 4d , R 5d , R 6d are each independently a hydrogen atom, a halogen atom, CN, NO 2 , C.F. 3 ,R,OR,SR,SOR,SO 2 R or NRR', R and R' each independently represent an alkyl group or an aryl group, and when R and R' are present at the same time, R and R' may be bonded to form a ring, and one or more -CH in the alkyl group or aryl group represented by R and R' 2 - may be independently substituted with -O-, -N-, -S-, -CO-, -COO-, -OCO- or a benzene ring; R 7d , R8d and R 9d each independently represents a hydrogen atom or a methyl group.
[0293] The photopolymerization initiator may also be a compound represented by formula (OX-5). Examples of such a compound include the compounds described in WO 2024 / 101219.
[0294] In formula (OX-5), R 1e ~R e5 each independently represents a hydrocarbon group which may have a substituent; n represents an integer of 0 to 4.
[0295] Specific examples of the oxime compound include the compounds shown below.
[0296]
[0297]
[0298]
[0299]
[0300]
[0301] As the photopolymerization initiator, a bifunctional or trifunctional or higher functional photopolymerization initiator may be used. Specific examples of the bifunctional or trifunctional or higher functional photopolymerization initiator include the compounds described in paragraph 0148 of WO 2022 / 065215.
[0302] The content of the photopolymerization initiator in the total solid content of the composition is preferably 0.1 to 30% by mass. The lower limit is preferably 0.5% by mass or more, and more preferably 1% or more. The upper limit is preferably 25% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less. Only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof be within the above range.
[0303] <<Compound Having a Cyclic Ether Group>> The composition of the present invention can contain a compound having a cyclic ether group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group. The epoxy group may be an alicyclic epoxy group. The alicyclic epoxy group refers to a monovalent functional group having a cyclic structure in which an epoxy ring and a saturated hydrocarbon ring are condensed. The compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound). Examples of epoxy compounds include compounds having one or more epoxy groups per molecule, and compounds having two or more epoxy groups are preferred. The epoxy compound is preferably a compound having 1 to 100 epoxy groups per molecule. The upper limit of the number of epoxy groups contained in the epoxy compound can be, for example, 10 or less, or 5 or less. The lower limit of the number of epoxy groups contained in the epoxy compound is preferably 2 or more.
[0304] Examples of compounds having a cyclic ether group include the compounds described in paragraphs 0034 to 0036 of JP-A-2013-011869, paragraphs 0147 to 0156 of JP-A-2014-043556, and paragraphs 0085 to 0092 of JP-A-2014-089408, compounds described in JP-A-2017-179172, xanthene-type epoxy resins described in JP-A-2021-195421, and xanthene-type epoxy resins described in JP-A-2021-195422.
[0305] The compound having a cyclic ether group may be a low molecular weight compound (for example, a molecular weight of less than 2000, or even less than 1000) or a high molecular weight compound (macromolecule) (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more). The weight average molecular weight of the compound having a cyclic ether group is preferably 200 to 100,000, and more preferably 500 to 50,000. The upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less.
[0306] Commercially available examples of compounds having a cyclic ether group include EHPE3150 (manufactured by Daicel Corporation), EPICLON N-695 (manufactured by DIC Corporation), Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (all manufactured by NOF Corporation, epoxy group-containing polymers).
[0307] The content of the compound having a cyclic ether group in the total solid content of the composition is preferably 0.1 to 20% by mass. The lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more. The upper limit is preferably 15% by mass or less, and more preferably 10% by mass or less. Only one type of compound having a cyclic ether group may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof be in the above range.
[0308] <<Curing Agent>> When the composition of the present invention contains a compound having a cyclic ether group, it is preferable that the composition of the present invention further contains a curing agent. Examples of curing agents include amine compounds, acid anhydride compounds, amide compounds, phenolic compounds, polycarboxylic acids, and thiol compounds. Specific examples of curing agents include succinic acid, trimellitic acid, pyromellitic acid, N,N-dimethyl-4-aminopyridine, and pentaerythritol tetrakis(3-mercaptopropionate). The curing agent may also be a compound described in paragraphs 0072 to 0078 of JP 2016-075720 A or a compound described in JP 2017-036379 A. The content of the curing agent is preferably 0.01 to 20 parts by mass, more preferably 0.01 to 10 parts by mass, and even more preferably 0.1 to 6.0 parts by mass, per 100 parts by mass of the compound having a cyclic ether group.
[0309] <<Ultraviolet Absorber>> The composition of the present invention may contain an ultraviolet absorber. Examples of the ultraviolet absorber include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, and dibenzoyl compounds. The ultraviolet absorber includes compounds described in paragraphs 0038 to 0052 of JP-A-2009-217221, compounds described in paragraphs 0052 to 0072 of JP-A-2012-208374, compounds described in paragraphs 0317 to 0334 of JP-A-2013-068814, compounds described in paragraphs 0061 to 0080 of JP-A-2016-162946, compounds described in paragraphs 0059 to 0076 of WO 2016 / 181987, compounds described in paragraphs 0052 and 0074 of WO 2021 / 131355, and compounds described in paragraphs 0022 to 0024 of WO 2021 / 132247. Compounds described in paragraph 0179 of International Publication No. 2022 / 085485, reactive triazine ultraviolet absorbers described in JP 2021-178918 A, ultraviolet absorbers described in JP 2022-007884 A, compounds described in Korean Patent Publication No. 10-2022-0014454, compounds described in JP 2023-013321 A, compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 A, compounds described in JP 2023-178225 A, compounds represented by formula (1) described in JP 2024-140703 A can also be used. Commercially available ultraviolet absorbers include the Tinuvin series and Uvinul (Uvinal) series manufactured by BASF Corporation. Further, examples of benzotriazole compounds include the MYUA series manufactured by Miyoshi Oil & Fats (The Chemical Daily, February 1, 2016). The content of the ultraviolet absorber in the total solid content of the composition is preferably 0.01 to 30% by mass. The lower limit is preferably 0.05% by mass or more. The upper limit is preferably 25% by mass or less, more preferably 20% by mass or less, even more preferably 10% by mass or less, and particularly preferably 5% by mass or less.The ultraviolet absorber may be used alone or in combination of two or more kinds. When two or more kinds are used, the total amount thereof is preferably in the above range.
[0310] <<Polymerization Inhibitor>> The composition of the present invention may contain a polymerization inhibitor. Examples of polymerization inhibitors include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.), and 2,2,6,6-tetramethylpiperidine 1-oxyl, with p-methoxyphenol being preferred. The content of the polymerization inhibitor in the total solids content of the composition is preferably 0.0001 to 5% by mass. Only one type of polymerization inhibitor may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof be within the above range.
[0311] <<Silane Coupling Agent>> The composition of the present invention can contain a silane coupling agent. The silane coupling agent is preferably a silane compound having a hydrolyzable group, and more preferably a silane compound having a hydrolyzable group and other functional groups. The hydrolyzable group refers to a substituent directly bonded to a silicon atom that can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, and an acyloxy group, with an alkoxy group being preferred. The silane coupling agent is preferably a compound having an alkoxysilyl group. Furthermore, examples of functional groups other than the hydrolyzable group include a vinyl group, a styrene group, a (meth)acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group, an isocyanate group, and a phenyl group, with a (meth)acryloyl group and an epoxy group being preferred. Examples of silane coupling agents include the compounds described in paragraph 0177 of WO 2022 / 085485 and the compounds described in JP 2019-183020 A. The content of the silane coupling agent in the total solid content of the composition is preferably 0.1 to 15% by mass. The upper limit is preferably 10% by mass or less, more preferably 5% by mass or less. The lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more. Only one type of silane coupling agent may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
[0312] <<Surfactant>> The composition of the present invention may contain a surfactant. As the surfactant, various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant may be used. The surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant. For details of the surfactant, reference may be made to the surfactants described in paragraphs 0238 to 0245 of WO 2015 / 166779, the contents of which are incorporated herein by reference.
[0313] As the fluorine-based surfactant, the compounds described in paragraphs 0167 to 0173 of WO 2022 / 085485 can be used.
[0314] Examples of nonionic surfactants include the compounds described in paragraph 0174 of WO 2022 / 085485.
[0315] Examples of silicone surfactants include SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, and SF 8419. OIL (all manufactured by Dow Toray Industries, Inc.), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (all manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (all manufactured by Shin-Etsu Chemical Co., Ltd.), BYK-307, BYK-322, BYK-323, BYK-330, BYK-3760, BYK-UV3510 (all manufactured by BYK-Chemie). As the silicone surfactant, compounds having the following structure can also be used.
[0316] As the surfactant, the polymer described in WO 2021 / 131726, the silicone-containing copolymer described in WO 2024 / 024440, the silicone-containing copolymer described in WO 2024 / 024441, and the leveling agent described in WO 2025 / 018168 can also be used.
[0317] The content of the surfactant in the total solid content of the composition is preferably 0.001 to 5% by mass. The lower limit is preferably 0.005% by mass or more. The upper limit is preferably 3% by mass or less, more preferably 1% by mass or less, even more preferably 0.5% by mass or less, and particularly preferably 0.2% by mass or less. Only one type of surfactant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
[0318] <<Antioxidant>> The composition of the present invention may contain an antioxidant. Examples of antioxidants include phenolic antioxidants, amine antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants. Examples of phenolic antioxidants include hindered phenol compounds. The phenolic antioxidant is preferably a compound having a substituent at the position adjacent to the phenolic hydroxy group (ortho position). The substituent is preferably a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms. The antioxidant is also preferably a compound having a phenol group and a phosphite ester group in the same molecule. Examples of phosphorus-based antioxidants include tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl)oxy]ethyl]amine, ethyl bis(2,4-di-tert-butyl-6-methylphenyl)phosphite, and tris(2,4-di-tert-butylphenyl)phosphite. Examples of commercially available antioxidants include ADK STAB AO-20, ADK STAB AO-30, ADK STAB AO-40, ADK STAB AO-50, ADK STAB AO-50F, ADK STAB AO-60, ADK STAB AO-60G, ADK STAB AO-80, ADK STAB AO-330, ADK STAB AO-412S, ADK STAB 2112, ADK STAB PEP-36, ADK STAB HP-10 (all manufactured by ADEKA Corporation), and JP-650 (manufactured by Johoku Chemical Industry Co., Ltd.). The antioxidant may be a compound described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, a compound described in International Publication No. WO 2017 / 006600, a compound described in International Publication No. WO 2017 / 164024, or a compound described in Korean Patent Publication No. 10-2019-0059371. The content of the antioxidant in the total solid content of the composition is preferably 0.01 to 20% by mass. The lower limit is preferably 0.3% by mass or more, and more preferably 0.5% by mass or more. The upper limit is preferably 15% by mass or less, and more preferably 10% by mass or less.The antioxidant may be used alone or in combination of two or more kinds. When two or more kinds are used, the total amount thereof is preferably within the above range.
[0319] <<Other Components>> The composition of the present invention may contain, as necessary, sensitizers, fillers, heat curing accelerators, plasticizers, and other auxiliaries (e.g., conductive particles, antifoaming agents, flame retardants, leveling agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, latent antioxidants, etc.). By appropriately incorporating these components, properties such as film physical properties can be adjusted. As these components, compounds described in paragraph 0182 of WO 2022 / 085485 can be used. In addition, as the chain transfer agent, thiol compounds described in JP 2020-109068 A can be used. Other components include compounds having two or more triethoxysilyl groups described in JP-A-2023-180607, metal compounds described in JP-A-2024-129722, metal compounds described in JP-A-2024-129724, metal compounds described in JP-A-2024-128802, metal compounds described in JP-A-2024-128809, and metal compounds described in JP-A-2024-129723.
[0320] The composition of the present invention may contain a compound derived from a biomass raw material, a compound containing a radioactive carbon atom, or a compound having a percent modern carbon of 50% or more. The content of the compound derived from a biomass raw material relative to all compounds contained in the composition of the present invention may be 20% by mass or more.
[0321] It is also preferable that the composition of the present invention is substantially free of terephthalic acid esters. Here, "substantially free" means that the content of terephthalic acid esters in the total amount of the composition is 1,000 ppb by mass or less, more preferably 100 ppb by mass or less, and particularly preferably zero.
[0322] From the viewpoint of environmental regulations, the composition of the present invention preferably has a melamine content of 10,000 ppm by mass or less.
[0323] The composition of the present invention preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less. The free halogen content is preferably 100 ppm or less, more preferably 50 ppm or less. Methods for reducing the free metals and halogens in the composition include washing with ion-exchanged water, filtration, ultrafiltration, purification with an ion-exchange resin, and purification with an inorganic adsorbent such as hydrotalcite.
[0324] From the standpoint of environmental regulations, the use of perfluoroalkyl sulfonic acids and their salts, and perfluoroalkyl carboxylic acids and their salts may be restricted. When the content of the above-mentioned compounds in the composition of the present invention is reduced, the content of perfluoroalkyl sulfonic acids (particularly perfluoroalkyl sulfonic acids having a perfluoroalkyl group with 6 to 8 carbon atoms) and their salts, and perfluoroalkyl carboxylic acids (particularly perfluoroalkyl carboxylic acids having a perfluoroalkyl group with 6 to 8 carbon atoms) and their salts is preferably in the range of 0.01 ppb to 1,000 ppb, more preferably in the range of 0.05 ppb to 500 ppb, and even more preferably in the range of 0.1 ppb to 300 ppb, based on the total solids content of the composition. The composition of the present invention may be substantially free of perfluoroalkyl sulfonic acids and their salts, and perfluoroalkyl carboxylic acids and their salts. For example, by using a compound that can replace perfluoroalkyl sulfonic acid and its salt, and a compound that can replace perfluoroalkyl carboxylic acid and its salt, a composition that is substantially free of perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt may be selected. Examples of compounds that can replace restricted compounds include compounds that are exempt from restrictions due to differences in the number of carbon atoms in the perfluoroalkyl group. However, the above does not preclude the use of perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt. The composition of the present invention may contain perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt within the maximum allowable range.
[0325] From the viewpoint of environmental regulations, the content of the fluorine-containing compound in the composition may be 5% by mass or less, 1% by mass or less, 100 ppm by mass or less, or 1 ppm by mass or less, or may be substantially free of the fluorine-containing compound.
[0326] The water content of the composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably 0.1 to 1.0% by mass. The water content can be measured by the Karl Fischer method.
[0327] <Storage container> The storage container for the composition of the present invention is not particularly limited, and a known storage container can be used. In addition, the container described in paragraph 0187 of WO 2022 / 085485 can be used as the storage container.
[0328] <Method for Preparing Composition> The composition of the present invention can be prepared by mixing the above-mentioned components. When preparing the composition, all components may be simultaneously dissolved or dispersed in a solvent to prepare the composition, or, if necessary, two or more solutions or dispersions in which the respective components are appropriately blended may be prepared in advance, and these may be mixed at the time of use (at the time of application) to prepare the composition.
[0329] The preparation of the composition may include a process for dispersing the pigment. In the process for dispersing the pigment, mechanical forces used to disperse the pigment include compression, squeezing, impact, shear, and cavitation. Specific examples of these processes include a bead mill, a sand mill, a roll mill, a ball mill, a paint shaker, a microfluidizer, a high-speed impeller, a sand grinder, a flow jet mixer, high-pressure wet atomization, and ultrasonic dispersion. Furthermore, when grinding the pigment in a sand mill (bead mill), it is preferable to use small-diameter beads, increase the bead packing ratio, or otherwise increase the grinding efficiency under such conditions. Furthermore, it is preferable to remove coarse particles after the grinding process by filtration, centrifugation, or the like. In addition, the process and disperser for dispersing pigments can be suitably used, for example, the process and disperser described in "Dispersion Technology Encyclopedia," published by Joho Kiko Co., Ltd., July 15, 2005, or "Comprehensive Collection of Dispersion Technology and Industrial Applications Focused on Suspension (Solid / Liquid Dispersion System)," published by the Management Development Center Publishing Department, October 10, 1978, or paragraph 0022 of JP 2015-157893 A. In addition, in the process for dispersing pigments, the pigment may be subjected to a salt milling process to refine the pigment. For details of the materials, equipment, processing conditions, etc. used in the salt milling process, see, for example, JP 2015-194521 A and JP 2012-046629 A. Examples of materials for beads used in dispersion include zirconia, agate, quartz, titania, tungsten carbide, silicon nitride, alumina, stainless steel, and glass. The beads may also be made of an inorganic compound having a Mohs hardness of at least 2. The composition may contain 1 to 10,000 ppm of the beads.
[0330] When preparing the composition, it is preferable to filter the composition with a filter for the purpose of removing foreign matter, reducing defects, etc. Examples of the types of filters and filtration methods used for filtration include the filters and filtration methods described in paragraphs 0196 to 0199 of WO 2022 / 085485.
[0331] <Film> Next, the film of the present invention will be described. The film of the present invention is obtained from the composition of the present invention described above. The film of the present invention can be preferably used as an optical filter. The use of the optical filter is not particularly limited, and examples thereof include color filters, infrared cut filters, and infrared transmission filters. Examples of infrared cut filters include infrared cut filters on the light-receiving side of a solid-state imaging device (e.g., as an infrared cut filter for a wafer-level lens), infrared cut filters on the back side (opposite the light-receiving side) of a solid-state imaging device, and infrared cut filters for ambient light sensors (e.g., an illuminance sensor that senses the illuminance and color tone of the environment in which an information terminal device is placed and adjusts the color tone of the display, or a color correction sensor that adjusts the color tone). In particular, the film can be preferably used as an infrared cut filter on the light-receiving side of a solid-state imaging device. Examples of infrared transmission filters include filters that block visible light and selectively transmit infrared rays of a specific wavelength or above.
[0332] The film of the present invention may have a pattern or may be a film without a pattern (flat film). The film of the present invention may be used by being laminated on a support, or may be used by being peeled off from the support. Examples of the support include semiconductor substrates such as silicon substrates and transparent substrates.
[0333] A charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a photoelectric conversion layer, a transparent conductive film, or the like may be formed on the semiconductor substrate used as a support. Furthermore, a partition wall is formed on the semiconductor substrate to separate each pixel. Examples of the partition wall include a metal, a metal oxide, and a black matrix. Furthermore, if necessary, an undercoat layer may be provided on the semiconductor substrate to improve adhesion with an upper layer, prevent diffusion of substances, or flatten the substrate surface.
[0334] The transparent substrate used as the support is not particularly limited as long as it is made of a material that can transmit at least visible light. Examples of substrates include substrates made of glass, resin, and the like. Examples of resins include polyester resins such as polyethylene terephthalate and polybutylene terephthalate; polyolefin resins such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymer; acrylic resins such as norbornene resin, polyacrylate, and polymethyl methacrylate; urethane resin, vinyl chloride resin, fluororesin, polycarbonate resin, polyvinyl butyral resin, and polyvinyl alcohol resin. Examples of glass include soda-lime glass, borosilicate glass, alkali-free glass, quartz glass, and copper-containing glass. Examples of copper-containing glass include copper-containing phosphate glass and copper-containing fluorophosphate glass. Commercially available copper-containing glass can also be used. Examples of commercially available copper-containing glass include NF-50 (manufactured by AGC Technoglass Co., Ltd.).
[0335] The thickness of the film of the present invention can be adjusted appropriately depending on the purpose. The thickness of the film can be 200 μm or less, 150 μm or less, 120 μm or less, 20 μm or less, 10 μm or less, or 5 μm or less. The lower limit of the film thickness is preferably 0.1 μm or more, more preferably 0.2 μm or more.
[0336] When the film of the present invention is used as an infrared cut filter, the film of the present invention preferably has a maximum absorption wavelength in the wavelength range of 650 to 1500 nm (preferably 660 to 1200 nm, more preferably 660 to 1000 nm). The average transmittance in the wavelength range of 400 to 550 nm is preferably 86% or more, more preferably 89% or more, even more preferably 92% or more, and particularly preferably 95% or more. The transmittance over the entire wavelength range of 420 to 550 nm is preferably 50% or more, more preferably 70% or more, and even more preferably 80% or more. The transmittance at at least one point in the wavelength range of 650 to 1500 nm (preferably 660 to 1200 nm, more preferably 660 to 1000 nm) is preferably 10% or less, more preferably 7% or less, even more preferably 4% or less, and particularly preferably 2% or less. Furthermore, when the absorbance at the maximum absorption wavelength of the film of the present invention is taken as 1, the average absorbance in the wavelength range of 400 to 550 nm is preferably less than 0.030, more preferably less than 0.025.
[0337] When the film of the present invention is used as an infrared transmission filter, it is preferable that the film of the present invention has, for example, any one of the following spectral characteristics (i1) to (i3). (i1): A filter having a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 850 nm, and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1000 to 1500 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 850 nm and transmit light with wavelengths longer than 950 nm. (i2): A filter having a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 950 nm, and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1500 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light with wavelengths longer than 1050 nm. (i3): A filter having a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 1050 nm and a minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1200 to 1500 nm. A film having such spectral characteristics can block light in the wavelength range of 400 to 1050 nm and transmit light with wavelengths longer than 1150 nm.
[0338] The film of the present invention can be used in various devices such as solid-state imaging devices such as CCDs (charge-coupled devices) and CMOSs (complementary metal-oxide semiconductors) (the imaging section can be made of compound semiconductors such as InGaAs, organic semiconductors, quantum dots, etc., in addition to Si), infrared sensors, light-emitting elements, optical communication devices (for both transmission and reception), and image display devices.
[0339] <Method for Producing Film> The film of the present invention can be produced through a step of applying the composition of the present invention.
[0340] Examples of the support include those described above. As a method for applying the composition, a known method such as spin coating can be used. For example, the application method described in paragraph 0207 of WO 2022 / 085485 can be used.
[0341] The composition layer formed by applying the composition may be dried (prebaked). When prebaking is performed, the prebaking temperature is preferably 150°C or lower, more preferably 120°C or lower, and even more preferably 110°C or lower. The lower limit can be, for example, 50°C or higher, or can be 80°C or higher. The prebaking time is preferably 10 seconds to 3000 seconds, more preferably 40 to 2500 seconds, and even more preferably 80 to 220 seconds. Drying can be performed using a hot plate, an oven, or the like.
[0342] The film manufacturing method may further include a step of forming a pattern. Examples of the pattern forming method include a pattern forming method using a photolithography method and a pattern forming method using a dry etching method, and a pattern forming method using a photolithography method is preferred. Note that when the film of the present invention is used as a flat film, the step of forming a pattern does not need to be performed. The step of forming a pattern will be described in detail below.
[0343] (When forming a pattern by photolithography) The pattern formation method by photolithography preferably includes a step of patternwise exposing a composition layer formed by applying the composition of the present invention (exposure step), and a step of developing and removing the unexposed portions of the composition layer to form a pattern (development step). If necessary, a step of baking the developed pattern (post-baking step) may be provided. Each step will be described below.
[0344] In the exposure step, the composition layer is exposed to light in a pattern. For example, the composition layer can be exposed to light in a pattern by using a stepper exposure machine, a scanner exposure machine, or the like, through a mask having a predetermined mask pattern. This allows the exposed portion to be cured.
[0345] Examples of radiation (light) that can be used for exposure include g-line and i-line. Light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used. Examples of light with a wavelength of 300 nm or less include KrF line (wavelength 248 nm) and ArF line (wavelength 193 nm), with KrF line (wavelength 248 nm) being preferred. Long-wave light sources of 300 nm or more can also be used.
[0346] The exposure may be performed by continuous irradiation with light or by pulsed irradiation (pulse exposure), which is an exposure method in which light irradiation and pauses are repeated in short cycles (for example, milliseconds or less).
[0347] The irradiation amount (exposure amount) is, for example, 0.03 to 2.5 J / cm 2 is preferred, and 0.05 to 1.0 J / cm 2 The oxygen concentration during exposure can be appropriately selected. In addition to exposure in the atmosphere, exposure may be performed in a low-oxygen atmosphere with an oxygen concentration of 19% by volume or less (e.g., 15% by volume, 5% by volume, or substantially oxygen-free), or in a high-oxygen atmosphere with an oxygen concentration of more than 21% by volume (e.g., 22% by volume, 30% by volume, or 50% by volume). The exposure illuminance can be appropriately set, and is usually 1000 W / m 2 ~100000W / m 2 (For example, 5000 W / m 2 , 15000W / m 2 , or 35,000 W / m 2 The oxygen concentration and exposure illuminance may be appropriately combined. For example, an oxygen concentration of 10% by volume and an illuminance of 10,000 W / m 2 , oxygen concentration 35% by volume, illuminance 20,000 W / m 2 etc.
[0348] Next, the unexposed portions of the composition layer after exposure are developed and removed to form a pattern. The unexposed portions of the composition layer can be developed and removed using a developer. As a result, the unexposed portions of the composition layer in the exposure step are dissolved into the developer, and only the photocured portions remain on the support. The temperature of the developer is preferably, for example, 20 to 30°C. The development time is preferably 20 to 180 seconds. Furthermore, to improve residue removability, the process of shaking off the developer every 60 seconds and then supplying fresh developer may be repeated several times.
[0349] Examples of the developer include organic solvents and alkaline developers, and alkaline developers are preferably used. Regarding the developer and the washing (rinsing) method after development, the developer and washing method described in paragraph 0214 of WO 2022 / 085485 can be used.
[0350] After development and drying, it is preferable to perform additional exposure treatment or heating treatment (post-baking). The additional exposure treatment or post-baking is a post-development curing treatment to ensure complete curing. The heating temperature in post-baking is preferably, for example, 100 to 240°C, more preferably 200 to 240°C. Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, convection oven (hot air circulation dryer), or high-frequency heater to achieve the above conditions for the developed film. When additional exposure treatment is performed, it is preferable that the light used for exposure has a wavelength of 400 nm or less. The additional exposure treatment may also be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
[0351] (When forming a pattern by a dry etching method) Pattern formation by a dry etching method can be performed by a method in which the composition of the present invention is applied to a support to form a composition layer, the composition layer is cured to form a cured layer, a patterned photoresist layer is then formed on the cured layer, and the patterned photoresist layer is then used as a mask to dry etch the cured layer using an etching gas. In forming the photoresist layer, it is preferable to perform a pre-bake treatment. For pattern formation by a dry etching method, the description in paragraphs 0010 to 0067 of JP 2013-064993 A can be referred to, and the contents of this specification are incorporated herein by reference.
[0352] <Optical Filter> The optical filter of the present invention has the above-described film of the present invention. Types of optical filters include color filters, infrared cut filters, and infrared transmission filters.
[0353] In addition to the above-described film of the present invention, the optical filter of the present invention may further include a copper-containing layer, a dielectric multilayer film, an ultraviolet absorbing layer, etc. Examples of ultraviolet absorbing layers include the absorbing layers described in paragraphs 0040 to 0070 and 0119 to 0145 of International Publication No. 2015 / 099060. Examples of dielectric multilayer films include the dielectric multilayer films described in paragraphs 0255 to 0259 of Japanese Patent Application Laid-Open No. 2014-041318. Examples of copper-containing layers include glass substrates made of copper-containing glass (copper-containing glass substrates) and layers containing copper complexes (copper complex-containing layers). Examples of copper-containing glass substrates include copper-containing phosphate glass and copper-containing fluorophosphate glass. Commercially available copper-containing glass products include NF-50 (manufactured by AGC Technoglass Co., Ltd.), BG-60, and BG-61 (all manufactured by Schott Corporation), and CD5000 (manufactured by HOYA Corporation).
[0354] The optical filter of the present invention may be formed on a support. Examples of the support include those described above. Preferred substrates include transparent substrates made of materials such as glass and resin. Examples of resins include polyester resins such as polyethylene terephthalate and polybutylene terephthalate; polyolefin resins such as polyethylene, polypropylene, and ethylene-vinyl acetate copolymer; acrylic resins such as norbornene resin, polyacrylate, and polymethyl methacrylate; urethane resin, vinyl chloride resin, fluororesin, polycarbonate resin, polyvinyl butyral resin, and polyvinyl alcohol resin. Examples of glass include soda-lime glass, borosilicate glass, alkali-free glass, quartz glass, and copper-containing glass. Furthermore, the optical filter may be formed directly on various elements.
[0355] <Solid-state imaging device> The film of the present invention can be used for a solid-state imaging device. The configuration of the solid-state imaging device is not particularly limited as long as it has a configuration including the film of the present invention and functions as a solid-state imaging device. For example, the following configurations can be mentioned.
[0356] The solid-state imaging device has a support on which a plurality of photodiodes constituting a light-receiving area and transfer electrodes made of polysilicon or the like are disposed; a light-shielding film made of tungsten or the like is disposed on the photodiodes and transfer electrodes, with only the light-receiving portions of the photodiodes being opened; a device protective film made of silicon nitride or the like is disposed on the light-shielding film so as to cover the entire light-shielding film and the light-receiving portions of the photodiodes; and a film of the present invention is disposed on the device protective film. Furthermore, the device protective film may have a light-focusing means (e.g., a microlens, etc.; the same applies hereinafter) disposed below the film of the present invention (on the side closer to the support), or a light-focusing means disposed on the film of the present invention. Furthermore, the color filter may have a structure in which a film forming each pixel is embedded in a space partitioned, for example, in a lattice pattern, by partition walls. In this case, the partition walls preferably have a lower refractive index than each pixel. Examples of imaging devices having such a structure include the devices described in JP 2012-227478 A and JP 2014-179577 A.
[0357] <Image Display Device> The film of the present invention can also be used in an image display device. Examples of image display devices include liquid crystal display devices and organic electroluminescence (organic EL) display devices. Definitions and details of image display devices are described, for example, in "Electronic Display Devices" (written by Akio Sasaki, published by Kogyo Chosakai Co., Ltd. in 1990) and "Display Devices" (written by Nobuaki Ibuki, published by Sangyo Tosho Co., Ltd. in 1989). Liquid crystal display devices are described, for example, in "Next Generation Liquid Crystal Display Technology" (edited by Tatsuo Uchida, published by Kogyo Chosakai Co., Ltd. in 1994). There are no particular limitations on the liquid crystal display device to which the present invention can be applied, and the present invention can be applied to various types of liquid crystal display devices described in the above-mentioned "Next Generation Liquid Crystal Display Technology." The image display device may include a white organic EL element. The white organic EL element preferably has a tandem structure. The tandem structure of organic EL elements is described in, for example, JP 2003-045676 A and Akiyoshi Mikami, editor, "The Frontline of Organic EL Technology Development - High Brightness, High Precision, Long Life, and Know-How Collection," Technical Information Association, pp. 326-328, 2008. The spectrum of white light emitted by the organic EL element preferably has strong maximum emission peaks in the blue region (430-485 nm), green region (530-580 nm), and yellow region (580-620 nm). It is more preferable that the spectrum has a maximum emission peak in the red region (650-700 nm) in addition to these emission peaks. The film of the present invention can also be used as an infrared-transmitting film provided in an opening for infrared communication formed in the frame portion of a protective plate for a display device.
[0358] <Infrared Sensor> The film of the present invention can also be used in an infrared sensor. The configuration of the infrared sensor is not particularly limited as long as it functions as an infrared sensor. Hereinafter, one embodiment of the infrared sensor will be described with reference to the drawings.
[0359] 1 , reference numeral 110 denotes a solid-state imaging element. An infrared cut filter 111 and an infrared transmission filter 114 are disposed on an imaging region of the solid-state imaging element 110. A color filter 112 is disposed on the infrared cut filter 111. A microlens 115 is disposed on the incident light hν side of the color filter 112 and the infrared transmission filter 114. A planarization layer 116 is formed to cover the microlens 115.
[0360] The infrared cut filter 111 can be formed using the composition of the present invention. The color filter 112 is a color filter formed with pixels that transmit and absorb light of specific wavelengths in the visible range, and is not particularly limited, and a conventionally known color filter for forming pixels can be used. For example, a color filter formed with red (R), green (G), and blue (B) pixels can be used. For example, the description in paragraphs 0214 to 0263 of JP 2014-043556 A can be referred to, and the contents of this document are incorporated herein. The characteristics of the infrared transmission filter 114 are selected according to the emission wavelength of the infrared LED used. The infrared transmission filter 114 can be formed using the composition of the present invention.
[0361] In the infrared sensor shown in FIG. 1 , an infrared cut filter (another infrared cut filter) other than the infrared cut filter 111 may be disposed on the planarization layer 116. Examples of the other infrared cut filter include those having a copper-containing layer and / or a dielectric multilayer film. Details of these filters are as described above. Furthermore, a dual bandpass filter may be used as the other infrared cut filter.
[0362] <Camera Module> The film of the present invention can also be used in a camera module. The configuration of the camera module is not particularly limited as long as it has the film of the present invention and functions as a camera module. For example, a camera module can be configured to have a solid-state image sensor, a lens, and a circuit for processing images obtained from the solid-state image sensor. Known lenses and circuits for processing images obtained from the solid-state image sensor used in the camera module can be used. Examples of camera modules include the camera modules described in JP 2016-006476 A and JP 2014-197190 A, the contents of which are incorporated herein by reference.
[0363] <Light-emitting element> The film of the present invention can also be used for a light-emitting element. The configuration of the light-emitting element is not particularly limited as long as it functions as a light-emitting element, and examples thereof include light-emitting diodes (LEDs), organic light-emitting diodes (OLEDs), quantum dot light-emitting diodes (QLEDs), and vertical-cavity surface-emitting lasers (VISELs). The film of the present invention may be formed directly on the light-emitting element, or may be disposed on the light-emitting path.
[0364] <Optical Communication Element> The film of the present invention can also be used in an optical communication element. The configuration of the optical communication element is not particularly limited as long as it functions as an optical communication element, and it may be a transmitting element or a receiving element. Examples of optical communication elements include infrared remote controls, infrared transceivers, optical interposers, and optical interconnections. The film of the present invention may be formed directly on a receiving element, or may be formed directly on a transmitting element, or may be disposed on a transmitting / receiving path.
[0365] The present invention will be explained in more detail below with reference to examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. In the structural formulas shown below, Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group.
[0366] Synthesis Examples Synthesis Example 1 Synthesis of Compound (SP-9) Compound (SP-9) was synthesized according to the following scheme.
[0367] -Synthesis of Compound SP-9A- 9.5 parts by mass of 1,4-butane sultone was added to 300 parts by mass of dehydrated tetrahydrofuran and cooled to -78°C. 48 mL of a 1.6 M n-butyllithium hexane solution was added dropwise, and the mixture was stirred for 30 minutes. Next, 13.5 parts by mass of bromotetradecane was added dropwise, and the mixture was stirred for 1 hour. Next, the temperature was raised to 20°C, and the mixture was stirred for an additional 1 hour. After completion of the reaction, the mixture was cooled to 0°C, and 380 parts by mass of a saturated aqueous ammonium chloride solution was added dropwise. Subsequently, 95 parts by mass of distilled water and 95 parts by mass of hexane were added, and a liquid separation operation was performed. The obtained organic layer was further washed with brine, and the obtained organic layer was distilled under reduced pressure at 50°C. The obtained solid was purified by column chromatography, yielding 8.0 parts by mass of compound SP-9A as a white solid. 1 H-NMR (CDCl 3 ): δ0.09 (t, 3H), δ1.80-2.01 (m, 24H), δ1.80-2.01 (m, 4H), δ2.20 (m, 2H), δ3.04 (m, 1H), δ4.40-4.60 (m, 2H)
[0368] The resulting white solid contained the following components as impurities. 1 H-NMR revealed that the sample contained 0 to 1 mol% each of compound SP-9Aa, compound SP-9Ab, and compound SP-9Ac. Gas chromatography revealed that the sample contained 0 to 3% by mass each of n-hexane and tetrahydrofuran. Karl Fischer moisture content analysis revealed that the sample contained 0 to 3% by mass of water. Inductively coupled plasma (ICP) atomic emission spectroscopy revealed that the sample contained 0 to 3% by mass of Na. Combustion ion chromatography revealed that the sample contained 0 to 3% by mass of Cl.
[0369] -Synthesis of Compound PP-2- Compound PP-2 was synthesized according to the synthesis method for compound (Ap-1-d) described in WO 2018 / 230387.
[0370] -Synthesis of Compound PP-6- Compound PP-6 was synthesized with reference to the synthesis method of compound (Ap-ppb-1) described in WO 2021 / 039205, and the reaction was stopped so as to contain the following components. 1 H-NMR revealed that the compound PP-6 contained 0.01 to 10 parts by mass of compound PP-6-E, 0 to 1 part by mass of compound PP-6-F, 0 to 1 part by mass of compound PP-6-G, 0 to 1 part by mass of compound PP-6-H, 0 to 1 part by mass of methanol, and 0 to 1 part by mass of tetrahydrofuran, relative to 100 parts by mass of compound PP-6. Karl Fischer water content analysis revealed that the compound PP-6 contained 0.1 to 5% by mass of water, relative to 100 parts by mass of compound PP-6. Inductively coupled plasma (ICP) atomic emission spectroscopy revealed that the compound PP-6 contained 0 to 1% by mass of Ti, relative to 100 parts by mass of compound PP-6. Combustion ion chromatography revealed that the compound PP-6 contained 0 to 1% by mass of Cl. The maximum absorption wavelength x was 881 nm, and the molar extinction coefficient was 740488 L / mol / cm. The peak positions in the powder X-ray diffraction spectrum were 5.7°, 6.4°, 9.6°, 11.4°, 12.2°, 12.7°, 13.4°, 13.8°, 14.4°, 14.9°, 16.1°, 16.8°, 17.7°, 18.2°, and 18.9° in terms of diffraction angle 2θ, and the peak with the maximum peak intensity was 5.7° or 6.4°, with a full width at half maximum of 0.20.
[0371] -Synthesis of Compound PP-9- Compound PP-9 was synthesized in the same manner as compound PP-6, with reference to the synthesis method for compound (Ap-ppb-1) described in WO 2021 / 039205, and the reaction was stopped so as to contain the following components. 1H-NMR revealed that the compound PP-9 contained 0.01 to 10 parts by mass of compound PP-9-E, 0 to 1 part by mass of compound PP-9-F, 0 to 1 part by mass of compound PP-9-G, 0 to 1 part by mass of compound PP-9-H, 0 to 1 part by mass of methanol, and 0 to 1 part by mass of tetrahydrofuran, relative to 100 parts by mass of compound PP-9. Karl Fischer water content analysis revealed that the compound PP-9 contained 0.1 to 5% by mass of water, relative to 100 parts by mass of compound PP-9. Inductively coupled plasma (ICP) atomic emission spectroscopy revealed that the compound PP-9 contained 0 to 1% by mass of Ti, relative to 100 parts by mass of compound PP-9. Combustion ion chromatography revealed that the compound PP-9 contained 0 to 1% by mass of Cl. The maximum absorption wavelength was 872 nm, and the molar extinction coefficient was 586,000 L / mol / cm. The peak positions in the powder X-ray diffraction spectrum were as follows: diffraction angle 2θ: 5.6°, 7.0°, 8.0°, 8.5°, 9.1°, 9.7°, 10.4°, 11.3°, 12.3°, 12.8°, 14.8°, 16.0°, 17.0°, 18.8°, and 2.7°; the peak with the maximum peak intensity was at 5.6°, and the full width at half maximum was 0.20.
[0372] -Synthesis of Compound SP-19- 1.4 parts by mass of compound SP-9B, 1.52 parts by mass of potassium carbonate (fine powder), 1.77 parts by mass of tetrabutylammonium bromide, and 12.6 parts by mass of dimethylacetamide were added and stirred at 25°C for 5 minutes. Next, 1.77 parts by mass of compound SP-9A was added, and the mixture was heated to 95°C and stirred. After completion of the reaction, the mixture was cooled to 30°C or below, and 42 parts by mass of methanol was added dropwise. After stirring for 30 minutes, the obtained crystals were separated by filtration and washed with 14 parts by mass of methanol. The obtained crystals were stirred in a 10% aqueous methanol solution and separated by filtration. The obtained green crystals were dried with a blower at 50°C for 12 hours, yielding 1.5 parts by mass of compound SP-19.
[0373] -Synthesis of Compound SP-9- 1.5 parts by mass of compound SP-19 was added in 10 portions to 28 parts by mass of 4 N aqueous hydrochloric acid solution. After stirring at 25°C for 1 hour, the resulting crystals were filtered and washed with 28 parts by mass of 4 N aqueous hydrochloric acid solution and 28 parts by mass of acetonitrile. The resulting green crystals were dried with air at 50°C for 12 hours to obtain 1.5 parts by mass of compound SP-19. A peak corresponding to a molecular weight of 1654.79 was observed by MALDI-MS (Matrix Assisted Laser Desorption / Ionization-Mass Spectrometry), and the compound was identified as (SP-9).
[0374] The obtained green crystals contained the following components as impurities. Liquid chromatography / mass spectrometry (LC-MS) revealed that they contained 0 to 5 mol% each of compound SP-9a, compound SP-9b, compound SP-9c, compound SP-9d, and compound PP-2. Gas chromatography revealed that they contained 0 to 3 mass% each of dimethylacetamide, acetonitrile, and methanol. Karl Fischer water content measurement revealed that they contained 0 to 20 mass% water. ICP atomic emission spectroscopy revealed that they contained 0 to 1 mass% K. Combustion ion chromatography revealed that they contained 0 to 1 mass% Cl.
[0375] <Preparation of Dispersion> After mixing the materials listed in the table below, 230 parts by mass of zirconia beads with a diameter of 0.3 mm were added, and the mixture was dispersed using a paint shaker for 5 hours. The beads were then separated by filtration to prepare a dispersion. The solids concentration of the dispersion was adjusted by the amount of solvent used. When two or more materials were listed in the solvent type column, the materials were used in the proportions (mass ratios) listed in the ratio column.
[0376]
[0377]
[0378] Details of the materials indicated by the abbreviations in the table above are as follows:
[0379] (Pigments) PP-1 to PP-9: Compounds having the following structures (infrared absorbing pigments, pyrrolopyrrole compounds) PB-1: C.I. Pigment Blue 15:6 (blue pigment, phthalocyanine compound) PG-1: C.I. Pigment Green 36 (green pigment, phthalocyanine compound) PG-2: C.I. Pigment Green 58 (green pigment, phthalocyanine compound) PIR-1: Compound having the following structure (infrared absorbing pigment, phthalocyanine compound) PIR-2 to PIR-4: Compounds having the following structure (infrared absorbing pigment, squarylium compound) PIR-5: Compound having the following structure (infrared absorbing pigment, croconium compound) PIR-6: Compound having the following structure (infrared absorbing pigment, indigo compound) PIR-7: Compound having the following structure (infrared absorbing pigment, indigo compound) PIR-8: Compound having the following structure (infrared absorbing pigment, pyrromethene compound) PY-1, PY-2: Compounds having the following structure (yellow pigment, isoindoline compound) PY-3 to PY-6: Compounds having the following structure (yellow pigment, quinophthalone compound) PY-7: Compound having the following structure (yellow pigment, azomethine compound) PR-1 to PR-4: Compounds having the following structure (red pigment, diketopyrrolopyrrole compound) PR-5, PR-6: Compounds having the following structure (red pigment, xanthene compound) PR-7: Compound having the following structure (red pigment, pyrromethene compound) PR-8, PR-9: Compounds having the following structure (red pigment, perylene compound) PR-10: Compound having the following structure (red pigment, quinacridone compound) PR-11: Compound having the following structure (red pigment, anthraquinone compound) PV-1: Compound having the following structure (purple pigment, dioxazine compound) PBk-1: Irgaphor Black S 0100CF (manufactured by BASF, black pigment, benzofuranone compound) rPP-1: Compound having the following structure (infrared absorbing pigment, pyrrolopyrrole compound)
[0380] (Pigment Derivatives) SP-1 to SP-42: Compounds having the following structure (compounds having a dye structure derived from a pyrrolopyrrole dye compound with an absorption maximum in the wavelength range of 700 to 1500 nm) SB-1: Compound having the following structure (compound having a dye structure derived from a phthalocyanine dye compound with an absorption maximum in the wavelength range of 400 to 700 nm) SG-1, SG-2: Compounds having the following structure (compounds having a dye structure derived from a phthalocyanine dye compound with an absorption maximum in the wavelength range of 400 to 700 nm) SIR-1: Compound having the following structure (compound having a dye structure derived from a phthalocyanine dye compound with an absorption maximum in the wavelength range of 700 to 1500 nm) SIR-2 to SIR-4: Compounds having the following structure (compounds having a dye structure derived from a squarylium dye compound with an absorption maximum in the wavelength range of 700 to 1500 nm) SIR-5: Compound having the following structure (compound having a dye structure derived from a croconium dye compound having a maximum absorption in the wavelength range of 700 to 1500 nm) SIR-6: Compound having the following structure (compound having a dye structure derived from an indigo dye compound having a maximum absorption in the wavelength range of 700 to 1000 nm) SIR-7: Compound having the following structure (compound having a dye structure derived from a pyrromethene dye compound having a maximum absorption in the wavelength range of 700 to 1000 nm) SY-1, SY-2: Compounds having the following structure (compounds having a dye structure derived from an isoindoline dye compound having a maximum absorption in the wavelength range of 400 to 700 nm) SY-3 to SY-6: Compounds having the following structure (compounds having a dye structure derived from a quinophthalone dye compound having a maximum absorption in the wavelength range of 400 to 700 nm) SY-7: Compound having the following structure (compound having a dye structure derived from an azomethine dye compound having a maximum absorption in the wavelength range of 400 to 700 nm) SR-1 to SR-4: Compounds having the following structure (compounds having a dye structure derived from a diketopyrrolopyrrole dye compound with a maximum absorption in the wavelength range of 400 to 700 nm) SR-5, SR-6: Compounds having the following structure (compounds having a dye structure derived from a xanthene dye compound with a maximum absorption in the wavelength range of 400 to 700 nm) SR-7: Compound having the following structure (compounds having a dye structure derived from a pyrromethene dye compound with a maximum absorption in the wavelength range of 400 to 700 nm)SR-8: Compound having the following structure (compound having a dye structure derived from a perylene dye compound having a maximum absorption in the wavelength range of 400 to 700 nm) SR-9: Compound having the following structure (compound having a dye structure derived from a quinacridone dye compound having a maximum absorption in the wavelength range of 400 to 700 nm) SR-10: Compound having the following structure (compound having a dye structure derived from an anthraquinone dye compound having a maximum absorption in the wavelength range of 400 to 700 nm) SV-1: Compound having the following structure (compound having a dye structure derived from a dioxazine dye compound having a maximum absorption in the wavelength range of 400 to 700 nm) SBk-1: Compound having the following structure (compound having a dye structure derived from a benzofuranone dye compound having a maximum absorption in the wavelength range of 400 to 700 nm) rsp-1: Compound having the following structure (compound having a dye structure derived from a pyrrolopyrrole dye compound having a maximum absorption in the wavelength range of 700 to 1500 nm, comparative compound) sa-1 to sa-32: Compounds having the following structure
[0381] SP-1 to SP-42, SB-1, SG-1, SG-2, SIR-1 to SIR-7, SY-1 to SY-7, SR-1 to SR-10, SV-1 and SBk-1 are materials that fall under the above-mentioned specific compounds.
[0382]
[0383] (Dispersants) Dis-1: Resin having the following structure (weight average molecular weight 15,000, acid value 30 mgKOH / g, amine value 50 mgKOH / g, the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units) Dis-2: Resin having the following structure (weight average molecular weight 12,000, acid value 100 mgKOH / g, amine value 110 mgKOH / g, the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units)
[0384] (Solvent) S-1: Propylene glycol monomethyl ether acetate S-2: Propylene glycol monomethyl ether S-3: Butyl acetate S-4: Cyclopentanone S-5: Nonane
[0385] <Performance Evaluation> (Evaluation of Dispersibility) The viscosity (mPa·s) of each dispersion immediately after production was measured using an E-type viscometer (RE-85L, manufactured by Toki Sangyo Co., Ltd.), and dispersibility was evaluated according to the following criteria. The viscosity measurements were carried out in a laboratory where the temperature and humidity were controlled at 22±5°C and 60±20%, with the temperature of the dispersion adjusted to 25°C. Each measurement was carried out three times, and the average value was used. A: Viscosity is 1 mPa·s or more and 5 mPa·s or less B: Viscosity is more than 5 mPa·s and 15 mPa·s or less C: Viscosity is more than 15 mPa·s and 50 mPa·s or less D: Viscosity is more than 50 mPa·s
[0386] (Storage Stability) The viscosity (mPa s) of each dispersion immediately after production was measured using an E-type viscometer (RE-85L, manufactured by Toki Sangyo Co., Ltd.). After measurement, each dispersion was left to stand for one day in a light-shielded state at 60°C, and then the viscosity (mPa s) was measured again. The viscosity change rate of the dispersion before and after the above-mentioned standing was calculated using the following formula, and the storage stability was evaluated according to the following evaluation criteria. The smaller the viscosity change rate value, the better the storage stability. All of the above viscosity measurements were performed in a laboratory where the temperature and humidity were controlled to 22±5°C and 60±20%, and the temperature of the dispersion was adjusted to 25°C. Each measurement was performed three times, and the average value was used. Viscosity change rate (%) = |(viscosity of dispersion after completion of leaving the above-mentioned - viscosity of dispersion immediately after production) | / (viscosity of dispersion immediately after production) x 100 A: Viscosity change rate is less than 5% B: Viscosity change rate is 5% or more and less than 10% C: Viscosity change rate is 10% or more and less than 20% D: Viscosity change rate is 20% or more
[0387]
[0388] As shown in the table above, dispersions A-1 to A-127, which used any one of SP-1 to SP-42, SB-1, SG-1, SG-2, SIR-1 to SIR-7, SY-1 to SY-7, SR-1 to SR-10, SV-1, and SBk-1 as the pigment derivative, were excellent in dispersibility and storage stability.
[0389] In the dispersions A-1 to A-89 and A-95 to A-127, the same evaluation results were obtained even when the ratio of S-1 to S-2 as the solvent was changed to S-1:S-2 = 96:4 or S-1:S-2 = 4:96.
[0390] <Preparation of Composition> The materials listed in the table below were mixed and stirred, and then filtered using a nylon filter with a pore size of 0.45 μm (manufactured by Nippon Pall Co., Ltd.) to prepare a composition. The solids concentration of the composition was adjusted by the amount of solvent added. When two or more materials were listed in the solvent type column, the materials were used in the proportion (mass ratio) listed in the ratio column.
[0391]
[0392]
[0393]
[0394]
[0395]
[0396] The raw materials listed in the above table with their abbreviations are as follows:
[0397] (Dispersion) Dispersion A-1 to A-1227, a-1: Dispersion A-1 to A-127, a-1 described above
[0398] (Resins) B-1: Random copolymer of allyl methacrylate and methacrylic acid (molar ratio 50:50, weight average molecular weight 20,000, molecular weight dispersity 2.1) B-2: Random copolymer of benzyl methacrylate and methacrylic acid (molar ratio 60 / 40, weight average molecular weight 20,000, molecular weight dispersity 1.9) B-3: Resin having the following structure (numbers added to the main chain are molar ratios; weight average molecular weight 15,000, molecular weight dispersity 2.1) B-4: Resin having the following structure (numbers added to the main chain are molar ratios; weight average molecular weight 25,000, molecular weight dispersity 2.2)
[0399] (Photopolymerization initiators) C-1 and C-2: Compounds having the following structures
[0400] (Polymerizable Compounds) M-1: Aronix M-305 (manufactured by Toagosei Co., Ltd., a mixture of pentaerythritol triacrylate and pentaerythritol tetraacrylate, the content of pentaerythritol triacrylate being 55% by mass to 63% by mass) M-2: KAYARAD RP-1040 (manufactured by Nippon Kayaku Co., Ltd., ethylene oxide-modified pentaerythritol tetraacrylate) M-3: Aronix M-510 (manufactured by Toagosei Co., Ltd., polybasic acid-modified acrylic oligomer) M-4: NK Ester A-TMMT (Shin-Nakamura Chemical Co., Ltd.)
[0401] (Surfactant) F-1: Compound having the following structure (silicone surfactant, number average molecular weight 933) F-2: Compound having the following structure (weight average molecular weight: 14,000; in the following formula, % indicating the proportion of repeating units is mol %)
[0402] (Polymerization inhibitor) G-1: p-methoxyphenol
[0403] (Ultraviolet absorber) U-1: Avobenzone
[0404] (Antioxidant) O-1: Adekastab AO-80 (manufactured by ADEKA Corporation, phenolic antioxidant)
[0405] (Solvent) S-1: Propylene glycol monomethyl ether acetate S-2: Propylene glycol monomethyl ether S-4: Cyclopentanone
[0406] <Evaluation Method> (Moisture Resistance) Each composition was applied to a glass substrate by spin coating and heated at 100°C for 2 minutes using a hot plate to obtain a composition layer. The obtained composition layer was exposed to 1000 mJ / cm using an i-line stepper exposure system FPA-3000i5+ (manufactured by Canon Corporation). 2 The entire surface was exposed to an exposure amount of 1.0 μm. Next, the substrate was heated at 180° C. for 5 minutes using a hot plate to produce a film with a thickness of 1.0 μm. The transmittance of the glass substrate on which the above film was formed was measured in the wavelength range of 400 to 2000 nm using an ultraviolet-visible-near-infrared spectrophotometer (U-4100, manufactured by Hitachi High-Tech Corporation). This film was placed in an incubator at 85° C. and 95% humidity for 6 months and stored therein, whereby a moisture resistance test was performed. Next, the transmittance of the film after the moisture resistance test was measured. For the film before and after the moisture resistance test, the change in transmittance (ΔT) in the wavelength range of 400 to 2000 nm was calculated using the following formula, and the moisture resistance was evaluated based on the value at the wavelength with the largest ΔT among all the measured wavelengths, according to the following criteria. The smaller the ΔT value, the better the moisture resistance. Change in transmittance (ΔT) = |Transmittance of film before humidity resistance test−Transmittance of film after humidity resistance test| A: ΔT≦5% B: 5%<ΔT≦10% C: 10%<ΔT≦20% D: 20%<ΔT
[0407]
[0408] As shown in the above table, the compositions of the examples were able to form films with excellent moisture resistance.
[0409] In Examples 1 to 89, 95 to 105, 124, 125, and 133 to 152, the same evaluation results were obtained when dispersions in which the ratio of S-1 to S-2 as the solvent was changed to S-1:S-2 = 96:4 or S-1:S-2 = 4:96 were used instead of dispersions A-1 to A-89 and A-95 to A-127.
[0410] 110: solid-state imaging element, 111: infrared cut filter, 112: color filter, 114: infrared transmission filter, 115: microlens, 116: planarization layer
Claims
a composition comprising a colorant containing a pigment, a compound represented by formula (1), a resin having an amine value, and a solvent; In formula (1), A 1 represents a pigment skeleton derived from a pigment compound, L 1 represents a single bond or a divalent linking group, L 2 and L 3 each independently represents a single bond or an alkylene group having 1 to 30 carbon atoms, R 1 represents an optionally substituted hydrocarbon group having 2 to 30 carbon atoms or an optionally substituted heteroaryl group, R 2 represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 1 and R 2 may be bonded to form a ring, X 1 represents an acid group or a salt thereof, p represents an integer of 1 to 20; A of the formula (1) 1 is a dye skeleton derived from a dye compound selected from a pyrrolopyrrole dye compound, a phthalocyanine dye compound, a squarylium dye compound, an indigo dye compound, a croconium dye compound, an isoindoline dye compound, a quinophthalone dye compound, a diketopyrrolopyrrole dye compound, a triarylmethane dye compound, a xanthene dye compound, a pyrromethene dye compound, a perylene dye compound, an azomethine dye compound, an anthraquinone dye compound, a quinacridone dye compound, a dioxazine dye compound, and a benzofuranone dye compound. R in the formula (1) 1 The composition according to claim 1 or 2, wherein is an optionally substituted alkyl group having 2 to 30 carbon atoms or an optionally substituted aryl group having 6 to 30 carbon atoms. R in the formula (1) 2 The composition of claim 3 , wherein is a hydrogen atom. X in the formula (1) 1 The composition according to claim 1 or 2, wherein is an acid group having a pKa of 4 or less or a salt thereof. L of the formula (1) 2 represents an alkylene group having 2 to 16 carbon atoms, L 3 The composition according to claim 1 or 2, wherein represents a single bond. A film obtained using the composition according to claim 1 or 2. An optical filter comprising the film according to claim 7. A solid-state imaging device comprising the film according to claim 7. An image display device comprising the film according to claim 7. An infrared sensor comprising the film according to claim 7. A camera module comprising the membrane of claim 7. A compound represented by formula (1a): In formula (1a), A 1a represents a dye skeleton derived from a dye compound selected from a pyrrolopyrrole dye compound, a phthalocyanine dye compound, a squarylium dye compound, an indigo dye compound, a croconium dye compound, an isoindoline dye compound, a quinophthalone dye compound, a diketopyrrolopyrrole dye compound, a triarylmethane dye compound, a xanthene dye compound, a pyrromethene dye compound, a perylene dye compound, an azomethine dye compound, an anthraquinone dye compound, a quinacridone dye compound, a dioxazine dye compound, and a benzofuranone dye compound; L 1a represents a single bond or a divalent linking group, L 2a and L 3a each independently represents a single bond or an alkylene group having 1 to 30 carbon atoms, R 1a represents an optionally substituted hydrocarbon group having 2 to 30 carbon atoms or an optionally substituted heteroaryl group, R 2a represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 1a and R 2a may be bonded to form a ring, X 1a represents an acid group or a salt thereof, p represents an integer of 1 to 20; a method for producing a compound represented by formula (1b) by reacting a dye compound with a compound represented by formula (10b); In the formula, A 1b represents a pigment skeleton derived from a pigment compound, L 1b represents a single bond or a divalent linking group, L 2b represents an alkylene group having 2 to 16 carbon atoms, R 1b represents an optionally substituted hydrocarbon group having 2 to 30 carbon atoms or an optionally substituted heteroaryl group, R 2b represents a hydrogen atom, a hydrocarbon group having 2 to 30 carbon atoms which may have a substituent, or a heteroaryl group which may have a substituent, R 1b and R 2b may be bonded to form a ring, X 1b represents a sulfo group or a salt thereof, p represents an integer of 1 to 20; A compound represented by formula (10c): In formula (10a), R 10c represents an alkyl group having 9 to 18 carbon atoms, an alkenyl group having 9 to 18 carbon atoms, or an alkynyl group having 9 to 18 carbon atoms.
Citation Information
Patent Citations
Colored composition for color filter, and color filter
JP2012212054A
Drying of electrolyte mixtures containing acids with molecular sieves
US20160133992A1
Dispersant composition, coloring composition and color filter
WO2020031634A1
Near-infrared absorption composition, film, optical filter and manufacturing method thereof, solid-state imaging element, infrared sensor, camera module, and inkjet ink
WO2021059846A1