Composition, film, optical filter, solid state imaging device, image display device, infrared radiation sensor, camera module, and compound
Patent Information
- Application Number
- PCT/JP2024/029232
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2023-08-30
- Filing Date
- 2024-08-19
- Publication Date
- 2025-03-06
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Figure JP2024029232_06032025_PF_FP_ABST
Abstract
Description
Composition, film, optical filter, solid-state imaging device, image display device, infrared sensor, camera module, and compound
[0001] The present invention relates to a composition containing an infrared absorbing dye. 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 a composition containing an infrared absorbing dye. Alternatively, the present invention relates to a compound.
[0002] Video cameras, digital still cameras, and mobile phones with camera functions use solid-state image sensors for color imaging, such as CCDs (charge-coupled devices) and CMOSs (complementary metal-oxide semiconductors). These solid-state image sensors use silicon photodiodes that are sensitive to infrared light in their light-receiving sections. For this reason, an infrared cut filter is sometimes used to correct visibility.
[0003] Infrared cut filters are produced using a composition containing an infrared absorber. Known examples of infrared absorbers include squarylium compounds and croconium compounds. Patent Document 1 describes the production of infrared cut filters and the like using a composition containing a specific squarylium compound.
[0004] Japanese Patent Application Laid-Open No. 2022-189736
[0005] Since dye compounds have a narrower band gap as their absorption wavelength shifts toward longer wavelengths, it has been difficult for them to achieve a HOMO (Highest Occupied Molecular Orbital)-LUMO (Lowest Unoccupied Molecular Orbital) level that allows for compatibility with various resistances (heat, light, radicals, oxidation, reduction, etc.). Therefore, infrared-absorbing dyes tend to be easily decomposed by the influence of light irradiation, heat, etc., and have low light resistance and heat resistance. In particular, squarylium compounds and croconium compounds, which have traditionally been used as infrared absorbers, tend to have low light resistance and heat resistance, and there has been room for further improvement in the light resistance and heat resistance of films obtained using compositions containing squarylium compounds or croconium compounds.
[0006] Furthermore, according to the investigations of the present inventors, it has been found that even with the composition disclosed in Patent Document 1, the light resistance and heat resistance of the resulting film are insufficient, and there is room for further improvement.
[0007] Therefore, an object of the present invention is to provide a composition capable of forming a film having excellent light resistance and heat 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, and a compound.
[0008] The present invention provides the following:
[0009] <1> A composition containing an infrared absorbing dye represented by formula (1), a curable compound, and a solvent; 1 ] s [A n- ] t ...(1) In formula (1), Z 1 represents a monovalent cation represented by formula (SQ-1) or formula (CR-1), and A n- represents an n-valent counter anion, n represents an integer of 2 or more, s represents an integer of 2 or more, t represents an integer of 1 or more, and s = n × t; In the formula, R A and R C each independently represents a hydrogen atom or a substituent; R B is -OR b1 , —OC(═O)R b1 , -OC(=O)NR b2 R b3 , -NR b2 R b3 , -NHC(=O)R b1 , -NHC(=O)OR b1 , -NHC(=O)NR b2 R b3 , -NHS(=O) 2 R b1 , -SR b1 or -S(=O) 2 R b1 represents R b1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group; R b2 and R b3each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R b2 and R b3 may be bonded to form a ring; T 1 is the formula (T 1A ), formula (T 1B ), formula (T 1C ) or formula (T 1D ) represents a group represented by the formula: T 2 is the formula (T 2A ), formula (T 2B ), formula (T 2C ) or formula (T 2D ) represents a group represented by the formula: In the formula, X 1 ~X 8 are each independently an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, or —NR X1 represents -, and R X1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a heterocyclic group; R 1 ~R 20 and R 31 ~R 50 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, a nitro group, a cyano group, or —OR L1 , -C(=O)R L1 , -C(=O)OR L1 , —OC(═O)R L1 , -NR L1 R L2 , -NHC(=O)R L1 , —C(═O)NR L1 R L2 , -NHC(=O)OR L1 , -OC(=O)NR L1 R L2 , -NHC(=O)NR L1 R L2 , -SR L1 , -S(=O) 2 R L1 , -S(=O) 2 OR L1 , -NHS(=O) 2 R L1 or -S(=O) 2 NR L1 R L2represents R L1 and R L2 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group; R L1 and R L2 may be bonded to form a ring, R 1 ~R 20 and R 31 ~R 50 two adjacent ones of R may be bonded to each other to form a ring; T1 and R T2 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a heterocyclic group. 1 is a monovalent cation represented by formula (SQ-1). 1 is the formula (T 1A ) or formula (T 1B ) is a group represented by T 2 is the formula (T 2A ) or formula (T 2B <4> The composition according to <2>, wherein A in the above formula (1) is a group represented by n- is an anion of a compound containing at least one atom selected from the group consisting of a tungsten atom, a molybdenum atom, a silicon atom, and a phosphorus atom, and an oxygen atom. <5> The composition according to any one of <1> to <4>, further containing a chromatic colorant and at least one infrared absorber selected from the group consisting of the infrared absorbing dye represented by formula (1). <6> A film obtained using the composition according to any one of <1> to <5>. <7> An optical filter having the film according to <6>. <8> A solid-state imaging device having the film according to <6>. <9> An image display device having the film according to <6>. <10> An infrared sensor having the film according to <6>. <11> A camera module having the film according to <6>. <12> A compound represented by formula (1a); [Z 1 ] s [A 1 n- ] t ...(1a) In formula (1a), Z1 represents a monovalent cation represented by formula (SQ-1) or formula (CR-1), and A 1 n- represents an n-valent counter anion, the n-valent counter anion being an anion of a compound containing at least one atom selected from the group consisting of a tungsten atom, a molybdenum atom, a silicon atom, and a phosphorus atom, and an oxygen atom, n represents an integer of 2 or more, s represents an integer of 2 or more, t represents an integer of 1 or more, and s = n × t; In the formula, R A and R C each independently represents a hydrogen atom or a substituent; R B is -OR b1 , —OC(═O)R b1 , -OC(=O)NR b2 R b3 , -NR b2 R b3 , -NHC(=O)R b1 , -NHC(=O)OR b1 , -NHC(=O)NR b2 R b3 , -NHS(=O) 2 R b1 , -SR b1 or -S(=O) 2 R b1 represents R b1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group; R b2 and R b3 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R b2 and R b3 may be bonded to form a ring; T 1 is the formula (T 1A ), formula (T 1B ), formula (T 1C ) or formula (T 1D ) represents a group represented by the formula: T 2 is the formula (T 2A ), formula (T 2B ), formula (T 2C ) or formula (T 2D ) represents a group represented by the formula: In the formula, X 1 ~X8 are each independently an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, or —NR X1 represents -, and R X1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a heterocyclic group; R 1 ~R 20 and R 31 ~R 50 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, a nitro group, a cyano group, or —OR L1 , -C(=O)R L1 , -C(=O)OR L1 , —OC(═O)R L1 , -NR L1 R L2 , -NHC(=O)R L1 , —C(═O)NR L1 R L2 , -NHC(=O)OR L1 , -OC(=O)NR L1 R L2 , -NHC(=O)NR L1 R L2 , -SR L1 , -S(=O) 2 R L1 , -S(=O) 2 OR L1 , -NHS(=O) 2 R L1 or -S(=O) 2 NR L1 R L2 represents R L1 and R L2 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group; R L1 and R L2 may be bonded to form a ring, R 1 ~R 20 and R 31 ~R 50 two adjacent ones of R may be bonded to each other to form a ring; T1 and R T2 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a heterocyclic group.
[0010] According to the present invention, a composition capable of forming a film having excellent light resistance and heat resistance can be provided. The present invention also provides a film, an optical filter, a solid-state imaging device, an image display device, an infrared sensor, a camera module, and a compound.
[0011] FIG. 1 is a schematic diagram illustrating an embodiment of an infrared sensor.
[0012] 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. As used herein, weight-average molecular weight and number-average molecular weight are defined as polystyrene equivalent values measured by gel permeation chromatography (GPC). As used herein, Me in chemical formulas represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group. As used herein, infrared light refers to light (electromagnetic waves) with a wavelength of 700 to 2500 nm. As used herein, total solids refers to the total mass of all components of a composition excluding the solvent. As used herein, the term "process" refers not only to an independent process, but also to a process that cannot be clearly distinguished from other processes, as long as the intended effect of the process is achieved.
[0013] <Composition> The composition of the present invention is characterized by containing an infrared absorbing dye represented by formula (1), a curable compound, and a solvent.
[0014] The infrared absorbing dye represented by formula (1) contained in the composition of the present invention is resistant to decomposition or modification by light or heat, and has excellent light resistance and heat resistance. The reason for this effect is presumed to be as follows. The infrared absorbing dye represented by formula (1) is a compound in which a monovalent cation represented by formula (SQ-1) or formula (CR-1) is bonded to a divalent or higher-valent counter anion, A n- The composition of the present invention containing such an infrared absorbing dye can form a film with small spectral characteristics upon light irradiation and small spectral variations upon heating.
[0015] The composition of the present invention can be used as a composition for an optical filter. Examples of optical filters include an infrared cut filter and an infrared transmission filter. Since the compound represented by formula (1) has excellent visible light transmittance and infrared shielding properties, the composition of the present invention is particularly preferably used as a composition for an infrared cut filter.
[0016] Each component used in the composition of the present invention will be described below.
[0017] <<Specific infrared absorbing dye (infrared absorbing dye represented by formula (1))>> The composition of the present invention contains an infrared absorbing dye represented by formula (1). Hereinafter, the infrared absorbing dye represented by formula (1) may also be referred to as a specific infrared absorbing dye.
[0018] [Z 1 ] s [A n- ] t ...(1) In formula (1), Z 1 represents a monovalent cation represented by formula (SQ-1) or formula (CR-1), and A n- represents an n-valent counter anion, n represents an integer of 2 or more, s represents an integer of 2 or more, t represents an integer of 1 or more, and s = n × t.
[0019] —Regarding s and t— In formula (1), s represents an integer of 2 or greater, and t represents an integer of 1 or greater. The ratio of s to t (s / t) is preferably 2 to 20, more preferably 2 to 10, and even more preferably 2 to 6.
[0020] -A n- -A in formula (1) n- represents an n-valent counter anion, where n is an integer of 2 or more. n is preferably an integer of 2 to 20, more preferably an integer of 2 to 10, and even more preferably an integer of 2 to 6. A n- The n-valent counter anion represented by may be an organic anion or an inorganic anion.
[0021] A n- Examples of the n-valent counter anion represented by formula (An-1) include anions represented by formula (An-1). an1 - (R an1 ) u ...(An-1) In formula (An-1), R an1 is -SO 3 - , -COO - or -PO 4 - represents L an1 represents a u-valent linking group, and u represents an integer of 2 or more. an1 The u-valent linking group represented by is an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, —O—, —S—, —NR La1 -, -CO-, -COO-, -OCO-, -SO 2 - and groups formed by combining two or more of these groups. La1 represents a hydrogen atom, an alkyl group, or an aryl group.
[0022] A n- It is also preferable that the n-valent counter anion represented by is a polymer having two or more anionic groups. 3 - , -COO - and -PO 4 - Examples include: A n-When the n-valent counter anion represented by is a polymer, A n- The weight average molecular weight of the n-valent counter anion represented by is preferably 1,000 to 100,000, and more preferably 1,500 to 50,000.
[0023] A n- The n-valent counter anion represented by the formula (I) is preferably an anion of a compound containing at least one atom selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus atoms and an oxygen atom (hereinafter also referred to as a specific anion) because it can further improve the heat resistance and further improve the storage stability of the composition. Examples of the specific anion include an isopolyacid anion and a heteropolyacid anion containing at least one atom selected from tungsten, molybdenum, silicon, and phosphorus atoms. In this specification, an isopolyacid refers to a dinuclear or higher condensed acid formed by condensation of only oxoacids of transition metals. Furthermore, a heteropolyacid refers to a dinuclear or higher condensed acid formed by condensation of an oxoacid of a transition metal with an oxoacid of an atom other than the transition metal. A n- It is more preferable that the n-valent counter anion represented by the formula (I) is an anion of a compound comprising a tungsten atom, a molybdenum atom, a phosphorus atom, and an oxygen atom.
[0024] Specific examples of the specific anion include tungstate anion ([W 6 O 19 ] 2- , [W 10 O 32 ] 4- , [WO 4 ] 2- etc.), molybdate anion ([Mo 2 O 7 ] 2- , [Mo 6 O 19 ] 2- , [Mo 8 O 26 ] 4- etc.), phosphotungstate anion ([PW 4 O 20 ] 4- , [P.W. 12 O 40 ]3- , [P 2 W 15 O 56 ] 12- , [P 2 W 17 O 61 ] 10- , [P 2 W 18 O 62 ] 6- etc.), phosphomolybdate anion ([P 2 Mo 18 O 62 ] 6- , [PMo 12 O 40 ] 3- etc.), phosphotungstomolybdate anion ([PW 12-x Mo x O 40 ] 3- (x is an integer from 1 to 11)), [P 2 W 18-y Mo y O 62 ] 6- (y is an integer from 1 to 17), silicotungstate anion ([SiW 9 O 34 ] 10- , [SiW 10 O 36 ] 8- , [SiW 11 O 39 ] 8- , [SiW 12 O 40 ] 4- etc.), silicomolybdate anion ([SiMo 12 O 40 ] 4- etc.), silicotungstomolybdate anion ([SiW 12-x Mo x O 40 ] 4- (wherein x is an integer of 1 to 11), and tungsten-based isopolyacid anions.
[0025] -Z 1 Regarding Z in formula (1) 1represents a monovalent cation represented by formula (SQ-1) or formula (CR-1), and is preferably a monovalent cation represented by formula (SQ-1).
[0026] [R A and R C Regarding R in formula (SQ-1) and formula (CR-1) A and R C R each independently represents a hydrogen atom or a substituent. A and R C Examples of the substituent represented by include the groups listed as the substituent T described below, and are preferably a halogen atom or an alkyl group, more preferably an alkyl group. The number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 3. The alkyl group is particularly preferably a methyl group. A and R C are each independently preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.
[0027] [R B Regarding R in formula (SQ-1) and formula (CR-1) B is -OR b1 , —OC(═O)R b1 , -OC(=O)NR b2 R b3 , -NR b2 R b3 , -NHC(=O)R b1 , -NHC(=O)OR b1 , -NHC(=O)NR b2 R b3 , -NHS(=O) 2 R b1 , -SR b1 or -S(=O) 2 R b1 represents R b1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group; R b2 and R b3 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; Rb2 and R b3 may be bonded to form a ring.
[0028] R b1 ~R b3 The number of carbon atoms in the alkyl group represented by R is preferably 1 to 20, more preferably 1 to 15, still more preferably 1 to 10, and particularly preferably 1 to 5. The alkyl group may be linear, branched, or cyclic, and is preferably linear or branched, and more preferably linear. b1 The number of carbon atoms in the alkenyl group represented by R is preferably 2 to 20, more preferably 2 to 15, still more preferably 2 to 10, and particularly preferably 2 to 5. The alkenyl group may be either linear or branched. b1 ~R b3 The number of carbon atoms in the aryl group represented by R is preferably 6 to 20, and more preferably 6 to 12. b1 ~R b3 The heterocyclic group represented by is preferably a heterocyclic group having a single ring or 2 to 8 fused rings, more preferably a heterocyclic group having a single ring or 2 to 4 fused rings. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3. Examples of heteroatoms constituting the ring of the heterocyclic group include a nitrogen atom, an oxygen atom, and a sulfur atom, and a nitrogen atom is preferred. The number of carbon atoms constituting the ring of the heterocyclic group is preferably 1 to 20, more preferably 1 to 18, and even more preferably 1 to 12. The heterocyclic group is preferably a 5- or 6-membered heterocyclic group. R b2 and R b3 may be bonded to form a ring. The ring formed is preferably a 5-membered or 6-membered ring. The alkyl group, alkenyl group, aryl group and heterocyclic group may have a substituent. Examples of the substituent include the groups listed as the substituent T described below. R b1 ~R b3 are each preferably independently a hydrogen atom or an alkyl group, more preferably an alkyl group.
[0029] R in formula (SQ-1) and formula (CR-1) B is -OR b1 , -NR b2 R b3or -SR b1 Preferably, -OR b1 or -NR b2 R b3 It is more preferable that:
[0030] [T 1 and T 2 Regarding T in formula (SQ-1) and formula (CR-1) 1 is the formula (T 1A ), formula (T 1B ), formula (T 1C ) or formula (T 1D ) represents a group represented by T 2 is the formula (T 2A ), formula (T 2B ), formula (T 2C ) or formula (T 2D ) represents a group represented by the formula:
[0031] In the formula, X 1 ~X 8 are each independently an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, or —NR X1 represents -, and R X1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a heterocyclic group; R 1 ~R 20 and R 31 ~R 50 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, a nitro group, a cyano group, or —OR L1 , -C(=O)R L1 , -C(=O)OR L1 , —OC(═O)R L1 , -NR L1 R L2 , -NHC(=O)R L1 , —C(═O)NR L1 R L2 , -NHC(=O)OR L1 , -OC(=O)NR L1 R L2 , -NHC(=O)NR L1 R L2 , -SR L1 , -S(=O) 2 R L1 , -S(=O)2 OR L1 , -NHS(=O) 2 R L1 or -S(=O) 2 NR L1 R L2 represents R L1 and R L2 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group; R L1 and R L2 may be bonded to form a ring, R 1 ~R 20 and R 31 ~R 50 two adjacent ones of R may be bonded to each other to form a ring; T1 and R T2 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a heterocyclic group.
[0032] In the above formula, X 1 ~X 8 are each independently an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, or —NR X1 represents an oxygen atom, a sulfur atom or —NR X1 Preferably, it is -, more preferably an oxygen atom or a sulfur atom, and even more preferably an oxygen atom. According to this embodiment, it is possible to further improve heat resistance and light resistance. Furthermore, it is also possible to improve infrared shielding properties and visible light transparency. -NR X1 -In R X1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a heterocyclic group, preferably a hydrogen atom or an alkyl group, more preferably an alkyl group.
[0033] R 1 ~R 20 , R 31 ~R 50 , R X1 , R T1 and R T2 Examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
[0034] R 1~R 20 , R 31 ~R 50 , R L1 , R L2 , R X1 , R T1 and R T2 The number of carbon atoms in the alkyl group represented by is preferably 1 to 20, more preferably 1 to 15, still more preferably 1 to 10, and particularly preferably 1 to 5. The alkyl group may be linear, branched, or cyclic.
[0035] R 1 ~R 20 , R 31 ~R 50 , R L1 and R L2 The number of carbon atoms in the alkenyl group represented by is preferably 2 to 20, more preferably 2 to 15, still more preferably 2 to 10, and particularly preferably 2 to 5. The alkenyl group may be either linear or branched.
[0036] R 1 ~R 20 , R 31 ~R 50 , R L1 , R L2 , R X1 , R T1 and R T2 The aryl group represented by the formula (I) preferably has 6 to 20 carbon atoms, and more preferably has 6 to 12 carbon atoms.
[0037] R 1 ~R 20 , R 31 ~R 50 , R L1 , R L2 , R X1 , R T1 and R T2The heterocyclic group represented by is preferably a monocyclic or fused ring heterocyclic group having 2 to 8 fused rings, more preferably a monocyclic or fused ring heterocyclic group having 2 to 4 fused rings. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3. Examples of heteroatoms constituting the ring of the heterocyclic group include a nitrogen atom, an oxygen atom, and a sulfur atom, and a nitrogen atom is preferred. The number of carbon atoms constituting the ring of the heterocyclic group is preferably 1 to 20, more preferably 1 to 18, and more preferably 1 to 12. The heterocyclic group is preferably a 5- or 6-membered heterocyclic group.
[0038] The alkyl group, alkenyl group, aryl group and heterocyclic group may have a substituent, such as the groups listed below for the substituent T.
[0039] R L1 and R L2 may be bonded to form a ring. The ring formed is preferably a 5-membered or 6-membered ring. The ring formed may further have a substituent. Examples of the substituent include the groups listed as the substituent T described below.
[0040] R 1 ~R 20 and R 31 ~R 50 Two adjacent ones of these may be bonded to each other to form a ring. The ring formed is preferably a 5-membered or 6-membered ring. The ring formed may further have a substituent. Examples of the substituent include the groups listed as the substituent T described below.
[0041] In the above formula, R 1 ~R 20 and R 31 ~R 50 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, or —OR L1 , -C(=O)R L1 , -C(=O)OR L1 , -NR L1 R L2 , -NHC(=O)R L1 or -NHS(=O) 2 R L1 It is preferable that RL1 and R L2 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a heterocyclic group, preferably a hydrogen atom or an alkyl group, more preferably an alkyl group.
[0042] T of formula (SQ-1) and formula (CR-1) 1 is the formula (T 1A ) or formula (T 1B ) is a group represented by T 2 is the formula (T 2A ) or formula (T 2B ) is preferably a group represented by T 1 is the formula (T 1A ) is a group represented by T 2 is the formula (T 1B According to this embodiment, it is possible to further improve the heat resistance and light resistance. Furthermore, it is also possible to improve the infrared shielding property and visible light transparency.
[0043] In addition, in the monovalent cation represented by formula (SQ-1), a structure in a resonance relationship may exist, and in the present invention, the monovalent cation represented by formula (SQ-1) also includes such a resonance structure. The same applies to the monovalent cation represented by formula (CR-1).
[0044] -Regarding the Substituent T- 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), a cycloalkyl group (preferably a cycloalkyl group having 5 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), and an alkoxy group. (preferably an alkoxy group having 1 to 30 carbon atoms), an aryloxy group (preferably 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), a carbonyl group), an acyloxy group (preferably an acyloxy group having 2 to 30 carbon atoms), an acylamino group (preferably an acylamino group having 2 to 30 carbon atoms), an aminocarbonylamino group (preferably an aminocarbonylamino group having 2 to 30 carbon atoms), an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 30 carbon atoms), an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 30 carbon atoms), a sulfamoyl group (preferably a sulfamoyl group having 0 to 30 carbon atoms), a sulfamoyl group an arylamino group (preferably a sulfamoylamino group having 0 to 30 carbon atoms), a carbamoyl 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 arylsulfonylamino group having 6 to 30 carbon atoms), a phenyl group), 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 further substitutable, they may further have a substituent. Examples of the substituent include the groups described above for the substituent T.
[0045] Specific examples of the specific infrared absorbing dye include compounds A-1 to A-26 shown below. Resonant structures of these compounds are also specific examples of the specific infrared absorbing dye. The weight-average molecular weight of the counter anion in compound A-25 is 20,400, and the numerical values attached to the repeating units are mass ratios.
[0046] In the table, T1-1 to T1-16 and T2-1 to T2-16 are the groups shown below.
[0047] The maximum absorption wavelength of the specific infrared absorbing dye is more preferably in the wavelength range of 700 to 1500 nm, even more preferably in the wavelength range of 700 to 1200 nm, and particularly preferably in the wavelength range of 700 to 1000 nm.
[0048] The content of the specific infrared absorbing dye (infrared absorbing dye represented by Formula (1)) in the total solid content of the composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more. The upper limit of the content of the specific infrared absorbing dye is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less. The composition of the present invention may contain only one type of specific infrared absorbing dye, or may contain two or more types. When two or more types are contained, the total amount thereof is preferably within the above range.
[0049] <<Curable Compound>> The composition of the present invention contains a curable compound. Examples of the curable compound include polymerizable compounds and resins. The resin may be a non-polymerizable resin (a resin without a polymerizable group) or a polymerizable resin (a resin with a polymerizable group). Examples of the polymerizable group include an ethylenically unsaturated bond-containing group, a cyclic ether group, a methylol group, and an alkoxymethyl group. Examples of the ethylenically unsaturated bond-containing group include a vinyl group, a vinylphenyl group, a (meth)allyl group, a (meth)acryloyl group, a (meth)acryloyloxy group, and a (meth)acryloylamide group. Preferred are a (meth)allyl group, a (meth)acryloyl group, and a (meth)acryloyloxy group, and more preferred are a (meth)acryloyloxy group. Examples of the cyclic ether group include an epoxy group and an oxetanyl group, and preferred is an epoxy group.
[0050] As the curable compound, it is preferable to use one that contains at least a resin. Furthermore, when the composition of the present invention is used as a composition for photolithography, it is preferable to use, as the curable compound, a resin and a polymerizable compound (preferably a polymerizable monomer that is a monomer-type polymerizable compound), and it is more preferable to use a resin and a polymerizable monomer having an ethylenically unsaturated bond-containing group (a monomer-type polymerizable compound).
[0051] (Polymerizable Compound) Examples of the polymerizable compound include a compound having an ethylenically unsaturated bond-containing group, a compound having a cyclic ether group, a compound having a methylol group, and a compound having an alkoxymethyl group. A compound having an ethylenically unsaturated bond-containing group can be preferably used as a radical polymerizable compound. In addition, a compound having a cyclic ether group can be preferably used as a cationically polymerizable compound.
[0052] Examples of resin-type polymerizable compounds include resins containing repeating units having polymerizable groups.
[0053] The molecular weight of the monomer-type polymerizable compound (polymerizable monomer) is preferably less than 2,000, and more preferably 1,500 or less. The lower limit of the molecular weight of the polymerizable monomer is preferably 100 or more, and more preferably 200 or more. The weight-average molecular weight (Mw) of the resin-type polymerizable compound is preferably 2,000 to 2,000,000. The upper limit of the weight-average molecular weight is preferably 1,000,000 or less, and more preferably 500,000 or less. The lower limit of the weight-average molecular weight is preferably 3,000 or more, and more preferably 5,000 or more.
[0054] The compound having an ethylenically unsaturated bond-containing group as a polymerizable monomer is preferably a trifunctional to 15-functional (meth)acrylate compound, more preferably a trifunctional to 6-functional (meth)acrylate compound. Specific examples include the compounds described in paragraphs 0075 to 0083 of WO 2022 / 065215 and the compounds described in Taiwan Patent Application Publication No. 201832008.
[0055] Examples of the compound having an ethylenically unsaturated bond-containing group 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.), and dipentaerythritol hexa(meth)acrylate (commercially available product: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.), NK Ester A-DPH-12E (manufactured by Shin-Nakamura Chemical Co., Ltd.), and compounds in which the (meth)acryloyl group of these compounds is bonded via an ethylene glycol and / or propylene glycol residue (for example, SR454 and SR499, commercially available from Sartomer). Examples of compounds having an ethylenically unsaturated bond-containing group include diglycerin EO (ethylene oxide)-modified (meth)acrylate (commercially available product is M-460, manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (NK Ester A-TMMT, manufactured by Shin-Nakamura Chemical Co., Ltd.), and 1,6-hexanediol diacrylate (KAYARAD, manufactured by Nippon Kayaku Co., Ltd.). HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Toagosei Co., Ltd.), NK Oligo UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (manufactured by Kyoeisha Chemical Co., Ltd.), dendrimer structure or hyperbranched structure described in JP-A-2023-043479, and the like can also be used.
[0056] As the compound having an ethylenically unsaturated bond-containing group, it is also preferable to use a trifunctional (meth)acrylate compound such as trimethylolpropane tri(meth)acrylate, trimethylolpropane propylene oxide-modified tri(meth)acrylate, trimethylolpropane ethylene oxide-modified tri(meth)acrylate, isocyanuric acid ethylene oxide-modified tri(meth)acrylate, or pentaerythritol tri(meth)acrylate. Commercially available trifunctional (meth)acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, M-305, M-303, M-452, and M-450 (manufactured by Toagosei Co., Ltd.), NK Ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A-TMM-3LM-N, A-TMPT, and TMPT (manufactured by Shin-Nakamura Chemical Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, and PET-30 (manufactured by Nippon Kayaku Co., Ltd.).
[0057] It is also preferable to use a compound having an ethylenically unsaturated bond-containing group and a urethane bond (hereinafter also referred to as a polymerizable compound having a urethane bond) as the compound having an ethylenically unsaturated bond-containing group. By using such a compound, the heat resistance of the obtained film can be further improved. The reason for this effect is presumed to be that the urethane bond portion forms a physical crosslinked structure due to intermolecular hydrogen bonding.
[0058] Examples of the polymerizable compound having a urethane bond include urethane (meth)acrylates obtained by reacting a (meth)acrylate having a hydroxy group with a polyfunctional isocyanate, and urethane (meth)acrylates obtained by reacting a polyhydric alcohol with a polyfunctional isocyanate and further reacting the resulting mixture with a (meth)acrylate having a hydroxy group.
[0059] Examples of the (meth)acrylate having a hydroxy group include 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythritol tri(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol ethylene oxide-modified penta(meth)acrylate, dipentaerythritol propylene oxide-modified penta(meth)acrylate, dipentaerythritol caprolactone-modified penta(meth)acrylate, glycerol acrylate methacrylate, glycerol dimethacrylate, 2-hydroxy-3-acryloylpropyl methacrylate, a reaction product of an epoxy group-containing compound and a carboxy(meth)acrylate, and a hydroxy group-containing polyol polyacrylate.
[0060] Examples of the polyfunctional isocyanate include aliphatic diisocyanates such as trimethylene diisocyanate, tetramethylene diisocyanate, and hexamethylene diisocyanate; alicyclic diisocyanates such as isophorone diisocyanate; aromatic diisocyanates such as tolylene diisocyanate, diphenylmethylene diisocyanate, and xylene diisocyanate; and biuret derivatives, isocyanate nurate derivatives, and trimethylolpropane adducts thereof.
[0061] As the polymerizable compound having a urethane bond, the compounds described in paragraphs 0308 to 0315 of JP-A No. 2022-173080 can also be used.
[0062] The compound having an ethylenically unsaturated bond-containing group may also be a compound having an acid group such as a carboxy group, a sulfo group, or a phosphate group. Commercially available products of such compounds include Aronix M-305, M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
[0063] As the compound having an ethylenically unsaturated bond-containing group, a compound having a caprolactone structure can also be used. For compounds having a caprolactone structure, please refer to the description in paragraphs 0042 to 0045 of JP 2013-253224 A, the contents of which are incorporated herein by reference. Examples of compounds having a caprolactone structure include DPCA-20, DPCA-30, DPCA-60, and DPCA-120, which are commercially available from Nippon Kayaku Co., Ltd. as the KAYARAD DPCA series.
[0064] The compound having an ethylenically unsaturated bond-containing group may also be a compound having an ethylenically unsaturated bond-containing group and an alkyleneoxy group. Such a compound is preferably a compound having an ethylenically unsaturated bond-containing group and an ethyleneoxy group and / or a propyleneoxy group, more preferably a compound having an ethylenically unsaturated bond-containing group and an ethyleneoxy group, and even more preferably a tri- to hexa-functional (meth)acrylate compound having 4 to 20 ethyleneoxy groups. Examples of commercially available products include SR-494, a tetrafunctional (meth)acrylate having four ethyleneoxy groups manufactured by Sartomer Corporation, and KAYARAD TPA-330, a trifunctional (meth)acrylate having three isobutyleneoxy groups manufactured by Nippon Kayaku Co., Ltd.
[0065] The compound having an ethylenically unsaturated bond-containing group may also be a polymerizable compound having a fluorene skeleton. Commercially available products include OGSOL EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomers having a fluorene skeleton).
[0066] It is also preferable to use a compound having an ethylenically unsaturated bond-containing group that is substantially free of environmentally restricted substances such as toluene. Commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
[0067] Examples of compounds having a cyclic ether group include compounds having an epoxy group and compounds having an oxetanyl group, with compounds having an epoxy group being preferred. Examples of compounds having an epoxy group include compounds having 1 to 100 epoxy groups per molecule. The upper limit of the number of epoxy groups can be, for example, 10 or less, or 5 or less. The lower limit of the number of epoxy groups is preferably 2 or more.
[0068] The compound having a cyclic ether group may be a low molecular weight compound (e.g., a molecular weight of less than 1,000) or a high molecular weight compound (macromolecule) (e.g., a molecular weight of 1,000 or more, and in the case of a polymer, a weight average molecular weight of 1,000 or more). The weight average molecular weight of the cyclic ether group is preferably 200 to 100,000, 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.
[0069] As the compound having a cyclic ether group, the compounds described in paragraphs 0034 to 0036 of JP-A-2013-011869, the compounds described in paragraphs 0147 to 0156 of JP-A-2014-043556, the compounds described in paragraphs 0085 to 0092 of JP-A-2014-089408, and the compounds described in JP-A-2017-179172 can also be used.
[0070] Commercially available compounds having a cyclic ether group include Denacol EX-212L, EX-212, EX-214L, EX-214, EX-216L, EX-216, EX-321L, EX-321, EX-850L, and EX-850 (all manufactured by Nagase ChemteX Corporation), ADEKA RESIN EP-4000S, EP-4003S, EP-4010S, EP-4011S (all manufactured by ADEKA Corporation), NC-2000, NC-3000, NC-7300, XD-1000, EPPN-501, EPPN-502 (all manufactured by ADEKA Corporation), Celloxide 2021P, Celloxide 2081, Celloxide 2083, Celloxide 2085, EHPE3150, EPOLEAD PB 3600, PB 4700 (all manufactured by Daicel Corporation), Cyclomer P ACA 200M, ACA 230AA, ACA Z250, ACA Z251, ACA Z300, ACA Z320 (all manufactured by Daicel Corporation), jER1031S, jER157S65, jER152, jER154, jER157S70 (all manufactured by Mitsubishi Chemical Corporation), Aron Oxetane OXT-121, OXT-221, OX-SQ, PNOX (all manufactured by Toagosei Co., Ltd.), Adeka Glycirol Examples of such monomers include ED-505 (manufactured by ADEKA Corporation, epoxy group-containing monomer), Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (manufactured by NOF Corporation, epoxy group-containing polymers), OXT-101, OXT-121, OXT-212, and OXT-221 (manufactured by Toagosei Co., Ltd., oxetanyl group-containing monomers), and OXE-10 and OXE-30 (manufactured by Osaka Organic Chemical Industry Ltd., oxetanyl group-containing monomers).
[0071] Compounds having a methylol group (hereinafter also referred to as methylol compounds) include compounds in which a methylol group is bonded to a nitrogen atom or a carbon atom forming an aromatic ring. Compounds having an alkoxymethyl group (hereinafter also referred to as alkoxymethyl compounds) include compounds in which an alkoxymethyl group is bonded to a nitrogen atom or a carbon atom forming an aromatic ring. Preferred compounds in which an alkoxymethyl group or a methylol group is bonded to a nitrogen atom include alkoxymethylated melamine, methylolated melamine, alkoxymethylated benzoguanamine, methylolated benzoguanamine, alkoxymethylated glycoluril, methylolated glycoluril, alkoxymethylated urea, and methylolated urea. Compounds described in paragraphs 0134 to 0147 of JP 2004-295116 A and paragraphs 0095 to 0126 of JP 2014-089408 A can also be used.
[0072] (Resin) The composition of the present invention can use a resin as the curable compound. It is preferable to use a curable compound that contains at least a resin. Resins are blended, for example, for purposes such as dispersing pigments and the like in the composition or as binders. 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. Resins having polymerizable groups also fall under the category of polymerizable compounds.
[0073] The weight average molecular weight of the resin is preferably 3,000 to 2,000,000. The upper limit is preferably 1,000,000 or less, more preferably 500,000 or less. The lower limit is preferably 4,000 or more, more preferably 5,000 or more.
[0074] Examples of the resin include (meth)acrylic resin, epoxy resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, vinyl acetate resin, polyvinyl alcohol resin, polyvinyl acetal resin, polyurethane resin, and polyurea resin. One of these resins may be used alone, or two or more of them may be mixed and used. From the viewpoint of improving heat resistance, norbornene resin is preferable as the cyclic olefin resin. Examples of commercially available norbornene resins include the ARTON series (e.g., ARTON F4520) manufactured by JSR Corporation. In addition, as the resin, the resins described in paragraph numbers 0091 to 0099 of International Publication No. 2022 / 065215, the block polyisocyanate resin described in Japanese Patent Application Laid-Open No. 2016-222891, the resin described in Japanese Patent Application Laid-Open No. 2020-122052, the resin described in Japanese Patent Application Laid-Open No. 2020-111656, the resin described in Japanese Patent Application Laid-Open No. 2020-139021, the resin containing a structural unit having a ring structure in the main chain and a structural unit having a biphenyl group in the side chain described in Japanese Patent Application Laid-Open No. 2017-138503, the resins described in paragraphs 0199 to 0233 of Japanese Patent Application Laid-Open No. 2020-186373, the alkali-soluble resin described in Japanese Patent Application Laid-Open No. 2020-186325, the resin represented by Formula 1 described in Korean Patent Publication No. 10-2020-0078339, the copolymer containing an epoxy group and an acid group described in International Publication No. 2022 / 030445, the resins described in paragraphs 0199 to 0233 of Japanese Patent Application Laid-Open No. 2020-186373, the alkali-soluble resin described in Japanese Patent Application Laid-Open No. 2020-186325, the resin represented by Formula 1 described in Korean Patent Publication No. 10-2020-0078339, the resin described in Japanese Patent Application Laid-Open No. 2021-134350, and the copolymer described in Japanese Patent Application Laid-Open No. 2020-041046 can also be used. Further, as the resin, a resin having a fluorene skeleton can also be preferably used.Examples of resins having a fluorene skeleton include resins described in U.S. Patent Application Publication No. 2017 / 0102610. Further, as the resin, the resin described in paragraphs 0199 to 0233 of JP 2020-186373 A, the alkali-soluble resin described in JP 2020-186325 A, the resin represented by formula 1 described in Korean Patent Publication No. 10-2020-0078339, the resin described in JP 2021-134350 A, the resin described in JP 2022-174597 A, the copolymer containing an epoxy group and an acid group described in WO 2022 / 030445, the resin described in JP 2018-135514 A, the resin described in JP 2023-033156 A, the resin described in JP 2023-030386 A, the resin described in JP 2023-027753 A can also be used.
[0075] It is preferable to use a resin having an acid group as the resin. Examples of the acid group include a carboxy group, a phosphate group, a sulfo group, and a phenolic hydroxy group. These acid groups may be of one type or two or more types. The resin having an acid group can also be used as a dispersant. The acid value of the resin having an acid group is preferably 30 to 500 mgKOH / g. The lower limit is preferably 50 mgKOH / g or more, and more preferably 70 mgKOH / g or more. The upper limit is preferably 400 mgKOH / g or less, more preferably 200 mgKOH / g or less, even more preferably 150 mgKOH / g or less, and most preferably 120 mgKOH / g or less.
[0076] It is also preferable to use a resin having a polymerizable group as the resin. The polymerizable group is preferably an ethylenically unsaturated bond-containing group or a cyclic ether group, and more preferably an ethylenically unsaturated bond-containing group.
[0077] The resin preferably contains a resin as a dispersant. Examples of dispersants include acidic dispersants (acidic resins) and basic dispersants (basic resins). Here, the term "acidic dispersant (acidic resin)" refers to a resin in which the amount of acid groups is greater than the amount of basic groups. As the acidic dispersant (acidic resin), a resin in which the amount of acid groups is 70 mol% or more is preferred when the total amount of the acid groups and the basic groups is taken as 100 mol%. The acid group possessed by the acidic dispersant (acidic resin) is preferably a carboxy group. The acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH / g. Furthermore, the term "basic dispersant (basic resin)" refers to a resin in which the amount of basic groups is greater than the amount of acid groups. As the basic dispersant (basic resin), a resin in which the amount of basic groups is greater than 50 mol% is preferred when the total amount of the acid groups and the basic groups is taken as 100 mol%. The basic group possessed by the basic dispersant is preferably an amino group.
[0078] The resin used as the dispersant is preferably a graft resin. For details of the graft resin, please refer to the description in paragraphs 0025 to 0094 of JP 2012-255128 A, the contents of which are incorporated herein by reference.
[0079] The resin used as the dispersant is preferably a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain. The polyimine-based dispersant is preferably a resin having a main chain with a partial structure containing 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 about polyimine-based dispersants, please refer to the description in paragraphs 0102 to 0166 of JP 2012-255128 A, the contents of which are incorporated herein by reference.
[0080] The resin used as a dispersant is preferably a resin having a structure in which multiple 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-A-2013-043962.
[0081] 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.
[0082] As the dispersant, the resin described in JP 2018-087939 A, the block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077 A, polyethyleneimine having a polyester side chain described in WO 2016 / 104803, block copolymers described in WO 2019 / 125940 A, block polymers having an acrylamide structural unit described in JP 2020-066687 A, block polymers having an acrylamide structural unit described in JP 2020-066688 A, dispersants described in WO 2016 / 104803, and the like can also be used.
[0083] 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.
[0084] The content of the curable compound in the total solid content of the composition is preferably 1 to 95% by mass. The lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, even more preferably 7% by mass or more, and particularly preferably 10% by mass or more. The upper limit is preferably 94% by mass or less, more preferably 90% by mass or less, even more preferably 85% by mass or less, and particularly preferably 80% by mass or less.
[0085] When the composition of the present invention contains a polymerizable compound as a curable compound, the content of the polymerizable compound in the total solid content of the composition is preferably 1 to 85% by mass. The lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more. The upper limit is preferably 80% by mass or less, more preferably 70% by mass or less.
[0086] When the composition of the present invention contains a polymerizable monomer as a curable compound, the content of the polymerizable monomer in the total solid content of the composition is preferably 1 to 50% by mass. The lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more. The upper limit is preferably 30% by mass or less, more preferably 20% by mass or less.
[0087] When the composition of the present invention contains a compound having an ethylenically unsaturated bond-containing group as a curable compound, the content of the compound having an ethylenically unsaturated bond-containing group in the total solid content of the composition is preferably 1 to 70% by mass. The lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more. The upper limit is preferably 65% by mass or less, more preferably 60% by mass or less.
[0088] When the composition of the present invention contains a compound having a cyclic ether group as a curable compound, the content of the compound having a cyclic ether group in the total solid content of the composition is preferably 1 to 95% by mass. The lower limit is preferably 2% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more. The upper limit is preferably 80% by mass or less, more preferably 70% by mass or less, and even more preferably 60% by mass or less.
[0089] When the composition of the present invention contains a resin as a curable compound, the content of the resin in the total solid content of the composition is preferably 1 to 85% by mass. The lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, even more preferably 7% by mass or more, and particularly preferably 10% by mass or more. The upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, even more preferably 70% by mass or less, and particularly preferably 40% by mass or less.
[0090] When the composition of the present invention contains a resin as a dispersant, the content of the resin as a dispersant in the total solid content of the composition is preferably 0.1 to 40% by mass. The upper limit is preferably 25% by mass or less, and more preferably 20% by mass or less. The lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more. Furthermore, the content of the resin as a dispersant is preferably 1 to 100 parts by mass per 100 parts by mass of the pigment. The upper limit is preferably 80 parts by mass or less, and more preferably 75 parts by mass or less. The lower limit is preferably 2.5 parts by mass or more, and more preferably 5 parts by mass or more.
[0091] The composition of the present invention may contain only one type of curable compound or may contain two or more types of curable compounds. When two or more types of curable compounds are contained, the total amount thereof is preferably within the above range.
[0092] <<Solvent>> The composition of the present invention contains a solvent. Examples of the solvent include water and organic solvents, and organic solvents are preferred. Examples of organic solvents include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents. For details, see paragraph 0223 of WO 2015 / 166779, the contents of which are incorporated herein by reference. Furthermore, ester solvents substituted with a cyclic alkyl group and ketone 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, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether ... Examples of suitable ethylene glycol monomethyl ether acetate include 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, and isopropyl alcohol.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).
[0093] 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).
[0094] 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.
[0095] 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.
[0096] The organic solvent preferably has a peroxide content of 0.8 mmol / L or less, and more preferably contains substantially no peroxide.
[0097] 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.
[0098] <<Other Infrared Absorbents>> The composition of the present invention can contain an infrared absorbent (other infrared absorbent) other than the specific infrared-absorbing dye described above. By further containing the other infrared absorbent, a film can be formed that can block infrared rays over a wider wavelength range. The other infrared absorbent may be a dye or a pigment (particles). Examples of the other infrared absorbent include pyrrolopyrrole compounds, polymethine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, and metal borides. At least one selected from squarylium compounds and phthalocyanine compounds is preferred.
[0099] Examples of the pyrrolopyrrole compound include the compounds described in paragraphs 0016 to 0058 of JP-A-2009-263614, the compounds described in paragraphs 0037 to 0052 of JP-A-2011-068731, and the compounds described in paragraphs 0010 to 0033 of WO 2015 / 166873. Examples of squarylium compounds include compounds described in paragraphs 0044 to 0049 of JP 2011-208101 A, compounds described in paragraphs 0060 to 0061 of Japanese Patent No. 6065169 A, compounds described in paragraph 0040 of WO 2016 / 181987 A, compounds described in JP 2015-176046 A, compounds described in paragraph 0072 of WO 2016 / 190162 A, and compounds described in JP 2016-07464 A. Compounds described in paragraphs 0196 to 0228 of Patent Publication No. 9, compounds described in paragraph 0124 of JP-A-2017-067963, compounds described in WO 2017 / 135359, compounds described in JP-A-2017-114956, compounds described in Japanese Patent No. 6197940, compounds described in WO 2016 / 120166, compounds described in Table 1 of U.S. Pat. No. 11261172, and the like. Examples of polymethine compounds include compounds described in paragraphs 0044 to 0045 of JP 2009-108267 A, compounds described in paragraphs 0026 to 0030 of JP 2002-194040 A, compounds described in JP 2015-172004 A, compounds described in JP 2015-172102 A, compounds described in JP 2008-088426 A, compounds described in paragraph 0090 of WO 2016 / 190162 A, compounds described in JP 2017-031394 A, compounds described in JP 2021-134350 A, compounds described in WO 2021 / 085372 A, and compounds described in paragraphs 0188 to 0192 of WO 2022 / 181422 A. Examples of croconium compounds include compounds described in JP-A-2017-082029 and compounds described in JP-A-2016-079331.Examples of iminium compounds include compounds described in JP-T-2008-528706, compounds described in JP-A-2012-012399, compounds described in JP-A-2007-092060, and compounds described in paragraphs 0048 to 0063 of WO 2018 / 043564. Examples of phthalocyanine compounds include compounds described in paragraph 0093 of JP-A-2012-077153, oxytitanium phthalocyanine described in JP-A-2006-343631, compounds described in paragraphs 0013 to 0029 of JP-A-2013-195480, vanadium phthalocyanine compounds described in Japanese Patent No. 6081771, and compounds described in WO 2020 / 071470. Examples of naphthalocyanine compounds include the compounds described in paragraph 0093 of JP 2012-077153 A and the compounds described in JP 2022-173080 A. Examples of dithiolene metal complexes include the compounds described in Japanese Patent No. 5733804 A. Examples of metal oxides include indium tin oxide, antimony tin oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, and tungsten oxide. For details on tungsten oxide, see paragraph 0080 of JP 2016-006476 A, the contents of which are incorporated herein by reference. Examples of metal borides include lanthanum boride. A commercially available lanthanum boride product is LaB. 6 -F (manufactured by Nippon Shinkinzoku Co., Ltd.). Furthermore, as the metal boride, compounds described in WO 2017 / 119394 can also be used. Commercially available indium tin oxide products include F-ITO (manufactured by Dowa Hitec Co., Ltd.).
[0100] Examples of the infrared absorber include squarylium compounds described in JP-A-2017-197437, squarylium compounds described in JP-A-2017-025311, squarylium compounds described in WO 2016 / 154782, squarylium compounds described in Japanese Patent No. 5884953, squarylium compounds described in Japanese Patent No. 6036689, squarylium compounds described in Japanese Patent No. 5810604, squarylium compounds described in paragraph 0 of WO 2017 / 213047, squarylium compounds described in ...9, squarylium compounds described in WO 2017 / 213049, squarylium compounds described in WO 2017 / 21304 JP-A-2018-054760, paragraphs 0019 to 0075, pyrrole ring-containing compounds described in JP-A-2018-040955, paragraphs 0078 to 0082, pyrrole ring-containing compounds described in JP-A-2018-002773, paragraphs 0043 to 0069, squarylium compounds having an aromatic ring at the amide α-position described in JP-A-2018-041047, paragraphs 0024 to 0086 compounds, amide-linked squarylium compounds described in JP-A-2017-179131, compounds having a pyrrole bis-type squarylium skeleton or a croconium skeleton described in JP-A-2017-141215, dihydrocarbazole bis-type squarylium compounds described in JP-A-2017-082029, asymmetric compounds described in paragraphs 0027 to 0114 of JP-A-2017-068120, and pyrrole ring-containing compounds described in JP-A-2017-067963 A compound (carbazole type), a phthalocyanine compound described in Japanese Patent No. 6251530, a compound described in JP 2019-127549 A, a compound described in WO 2022 / 059619 A, a compound described in JP 2022-151682 A, a compound described in JP 2022-188858 A, a compound described in JP 2022-184710 A, a compound described in JP 2022-189736 A, and the like can also be used.
[0101] As another infrared absorber, tungsten oxide represented by the following formula described in paragraph 0025 of European Patent No. 3628645 can also be used: 1 a M 2b W c O d (P(O) n R m ) e M 1 , M 2 represents an ammonium cation or a metal cation, a is 0.01 to 0.5, b is 0 to 0.5, c is 1, d is 2.5 to 3, e is 0.01 to 0.75, n is 1, 2 or 3, m is 1, 2 or 3, and R represents a hydrocarbon group which may have a substituent.
[0102] The content of the other infrared absorbent is preferably 1 to 100 parts by mass, more preferably 3 to 60 parts by mass, and even more preferably 5 to 40 parts by mass, relative to 100 parts by mass of the above-mentioned specific infrared absorbing dye. The total content of the above-mentioned specific infrared absorbing dye and the other infrared absorbent is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, based on the total solid content of the composition. The upper limit of the above total content is preferably 50% by mass or less, more preferably 40% by mass or less, and even more preferably 30% by mass or less.
[0103] <<Pigment Derivative>> The composition of the present invention may contain a pigment derivative. The pigment derivative is used as a dispersing aid. A dispersing aid is a material that enhances the dispersibility of the pigment in the composition.
[0104] Examples of the pigment derivative include a compound having at least one structure selected from the group consisting of a dye structure and a triazine structure, and an acid group or a basic group.
[0105] Examples of the dye structure include a squarylium dye structure, a pyrrolopyrrole dye structure, a diketopyrrolopyrrole dye structure, a quinacridone dye structure, an anthraquinone dye structure, a dianthraquinone dye structure, a benzisoindole dye structure, a thiazine indigo dye structure, an azo dye structure, a quinophthalone dye structure, a phthalocyanine dye structure, a naphthalocyanine dye structure, a dioxazine dye structure, a perylene dye structure, a perinone dye structure, a benzimidazolone dye structure, a benzothiazole dye structure, a benzimidazole dye structure, and a benzoxazole dye structure. Of these, a squarylium dye structure, a pyrrolopyrrole dye structure, a diketopyrrolopyrrole dye structure, a phthalocyanine dye structure, a quinacridone dye structure, and a benzimidazolone dye structure are preferred, and a squarylium dye structure and a pyrrolopyrrole dye structure are more preferred.
[0106] Examples of the acid group possessed by the pigment derivative include a carboxy group, a sulfo group, a phosphoric acid group, a boronic acid group, a carboxylic acid amide group, a sulfonic acid amide group, an imidic acid group, and salts thereof. Examples of the atom or atomic group constituting the salt include an alkali metal ion (Li + , Na + , K. + etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ Examples of the carboxylic acid amide group include -NHCOR, ... X1 As the sulfonic acid amide group, a group represented by -NHSO is preferred. 2 R X2 As the imide acid group, a group represented by -SO 2 NHSO 2 R X3 , -CONHSO 2 R X4 , -CONHCOR X5 or -SO 2 NHCOR X6 A group represented by the formula: 2 NHSO 2 R X3 is more preferred. X1 ~R X6R each independently represents an alkyl group or an aryl group. X1 ~R X6 The alkyl group and aryl group represented by may have a substituent. The substituent is preferably a halogen atom, more preferably a fluorine atom.
[0107] Examples of basic groups possessed by the pigment derivative include amino groups, pyridinyl groups and their salts, ammonium salts, 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.
[0108] Specific examples of pigment derivatives include compounds described in paragraphs 0037 to 0054 of WO 2016 / 035695, compounds described in paragraphs 0061 to 0086 of WO 2017 / 146092, compounds described in paragraphs 0017 to 0068 of WO 2018 / 230387, compounds described in paragraphs 0085 to 0099 of WO 2020 / 054718, compounds described in paragraph 0099 of WO 2020 / 054718, compounds described in paragraph 0124 of WO 2022 / 085485, benzimidazolone compounds or salts thereof described in JP-A-2018-168244, and compounds having an isoindoline skeleton described in the general formula (1) of Japanese Patent No. 6996282.
[0109] The content of the pigment derivative is preferably 1 to 50 parts by mass relative to 100 parts by mass of the pigment. The lower limit is preferably 3 parts by mass or more, and more preferably 5 parts by mass or more. The upper limit is preferably 40 parts by mass or less, and more preferably 30 parts by mass or less. Only one type of pigment derivative 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 be in the above range.
[0110] <<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 not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light in the ultraviolet to visible region is preferred. The photopolymerization initiator is preferably a photoradical polymerization initiator.
[0111] Examples of the photopolymerization initiator include halogenated hydrocarbon derivatives (e.g., 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, etc. From the viewpoint of exposure sensitivity, 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, or a 3-aryl-substituted coumarin compound, more preferably a compound selected from an oxime compound, an α-hydroxyketone compound, an α-aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound.Further, as the photopolymerization initiator, compounds described in paragraphs 0065 to 0111 of JP-A No. 2014-130173, compounds described in Japanese Patent No. 6301489, 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-0459, 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. 1107643 Initiators described in Patent Publication No. 67, 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, Korean Patent Publication No. 10-2017-0087330, Examples of the photopolymerization initiator include compounds described in WO 2019 / 013112, compounds having a triarylamine or N-arylcarbazole skeleton described in paragraphs 0042 to 0062, oxime ester photopolymerization initiators described in Japanese Patent No. 7219378, photopolymerization initiators described in Korean Patent Publication No. 10-2021-0146174, photopolymerization initiators described in WO 2019 / 013112, and photopolymerization initiators described in JP 2023-033731 A.
[0112] Specific examples of hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole.
[0113] 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.
[0114] Examples of oxime compounds include compounds described in paragraph 0142 of WO 2022 / 085485, compounds described in Japanese Patent No. 5430746, compounds described in Japanese Patent No. 5647738, compounds represented by the general formula (1) of JP 2021-173858 A and compounds described in paragraphs 0022 to 0024, compounds represented by the general formula (1) of JP 2021-170089 A and compounds described in paragraphs 0117 to 0120, oxime ester compounds described in Chinese Patent Application Publication No. 110066225, compounds described in Korean Patent Publication No. 10-2022-0076157, compounds described in paragraphs 0042 to 0062 of WO 2019 / 013112 having a triarylamine or N- arylcarbazole skeleton, and the like. 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, and Irgacure OXE04 (manufactured by BASF), TR-PBG-301, TR-PBG-304, and TR-PBG-327 (manufactured by TRONLY), and ADEKA OPTOMER N-1919 (manufactured by ADEKA Corporation, photopolymerization initiator 2 described in JP-A-2012-014052). Furthermore, 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, and NCI-930 (manufactured by ADEKA Corporation).
[0115] 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.
[0116] As the photopolymerization initiator, a compound represented by formula (OX-1) can also be used.
[0117] 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.
[0118] 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 rings are bonded via a single bond or a linking group, a divalent group in which two or more heterocycles are bonded via a single bond or a linking group, and a divalent group in which an aromatic ring and a heterocycle are bonded via a single bond or a linking group. Examples of the linking group that bonds the above-mentioned aromatic rings, heterocyclic groups, or aromatic rings and heterocycles 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.
[0119] 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). 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 heterocyclic group.
[0120] 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 heterocyclic group.
[0121] 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 heterocyclic group.
[0122] 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 heterocyclic group.
[0123] 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 heterocyclic group.
[0124] R X1 ~R X9 The heterocyclic group represented by is preferably a 5-membered or 6-membered ring. The heteroatoms contained in the heterocyclic group are preferably oxygen atoms, nitrogen atoms, and sulfur atoms. The number of heteroatoms contained in the heterocyclic group is preferably 1 to 3. The heterocyclic 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.
[0125] R in formula (OX-1) 1a represents a hydrogen atom or an acyl group, and is preferably an acyl group. 1a The acyl group represented by is —C(O)—R 101 It is preferable that R 101 represents an aryl group or a heterocyclic group, and is preferably an aryl group.
[0126] R 101 The number of carbon atoms in the aryl group represented by R is preferably 6 to 20, and more preferably 6 to 12. 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 heterocyclic group. 101 The aryl group represented by is preferably a phenyl group, a methylphenyl group or a naphthyl group, more preferably a methylphenyl group or a naphthyl group.
[0127] R 101 The heterocyclic group represented by is preferably a 5-membered or 6-membered ring. The heteroatoms contained in the heterocyclic group are preferably oxygen atoms, nitrogen atoms, and sulfur atoms. The number of heteroatoms contained in the heterocyclic group is preferably 1 to 3. The heterocyclic 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.
[0128] 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.
[0129] R in formula (OX-1) 3a and R 4a R 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.
[0130] Alk of formula (OX-1) 1 and Alk 2each 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.
[0131] In formula (OX-1), n represents 0 or 1, and is preferably 0.
[0132] 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.
[0133] As the photopolymerization initiator, a compound represented by formula (OX-2) can also be used.
[0134] 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 aromatic ring group or a heterocyclic group which may have a substituent; n represents 0 or 1;
[0135] R 1b and R 2bExamples 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 heterocyclic 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 heterocyclic group.
[0136] 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.
[0137] Ar 1b represents an aromatic ring group or a heterocyclic group which may have a substituent, Ar 1b is preferably an aromatic ring group which may have a substituent. The aromatic ring group is preferably a benzene ring group or a naphthalene ring group, and more preferably a benzene ring group. 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. Examples of the acyl group include the acyl groups described above.
[0138] As the photopolymerization initiator, a compound represented by formula (OX-3) can also be used.
[0139] 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 3ceach 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 represents -O- or -S-; k represents 0 or 1; m represents an integer of 0 to 4; and n represents 0 or 1.
[0140] R 1c and R 2c 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 heterocyclic 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 heterocyclic group. R 2c is preferably an alkyl group having a branched or cyclic structure.
[0141] 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. Examples of the acyl group include the acyl groups described above.
[0142] Ar 1c represents 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.
[0143] Ar 2crepresents 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.
[0144] k represents 0 or 1, and is preferably 0.
[0145] m represents an integer of 0 to 4, preferably 0 or 1, and more preferably 1.
[0146] Specific examples of oxime compounds that can be preferably used in the present invention are shown below, but the present invention is not limited to these.
[0147]
[0148] The oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, and more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 to 480 nm. Furthermore, from the viewpoint of sensitivity, the molar absorption coefficient of the oxime compound at a wavelength of 365 nm or 405 nm is preferably high, more preferably 1,000 to 300,000, even more preferably 2,000 to 300,000, and particularly preferably 5,000 to 200,000. The molar absorption coefficient of the compound can be measured using a known method. For example, it is preferably measured using a spectrophotometer (Varian Cary-5 spectrophotometer) at a concentration of 0.01 g / L using ethyl acetate as a solvent.
[0149] As the photopolymerization initiator, a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used. By using such a photoradical polymerization initiator, two or more radicals are generated from one molecule of the photoradical polymerization initiator, thereby obtaining good sensitivity. Furthermore, when a compound with an asymmetric structure is used, crystallinity is reduced and solubility in solvents is improved, making it less likely to precipitate over time, thereby improving the stability of the composition over time. Specific examples of bifunctional or trifunctional or higher functional photoradical polymerization initiators include the compounds described in paragraph 0148 of WO 2022 / 065215.
[0150] 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. The composition may contain only one type of photopolymerization initiator, or may contain two or more types. When two or more types are contained, the total amount thereof preferably falls within the above range.
[0151] <<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 the compounds described in paragraphs 0072 to 0078 of JP 2016-075720 A or the compounds 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.
[0152] <<Chromatic Colorant>> The composition of the present invention can contain a chromatic colorant. Examples of chromatic colorants include red colorants, green colorants, blue colorants, yellow colorants, purple colorants, and orange colorants. The chromatic colorant may be a pigment or a dye. A pigment and a dye may be used in combination. The pigment may be either an inorganic pigment or an organic pigment. Furthermore, the pigment may be a material in which an inorganic pigment or an organic-inorganic pigment has been partially substituted with an organic chromophore. Substituting an inorganic pigment or an organic-inorganic pigment with an organic chromophore makes it easier to design the hue.
[0153] 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 an image 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. In this specification, the average primary particle diameter is the arithmetic mean value of the primary particle diameters of 400 primary particles of the pigment. Furthermore, primary particles of the pigment refer to independent particles that are not aggregated.
[0154] 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.
[0155] 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 2The 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.
[0156] The chromatic colorant preferably contains a pigment. The content of the pigment in the chromatic colorant is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, and particularly preferably 90% by mass or more. Examples of the pigment include the following.
[0157] Color Index (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, 13 8,139,147,148,150,151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,199,213,214,215,228,231,232 (methine-based), 233 (quinoline-based), 234 (aminoketone-based), 235 (aminoketone-based), 236 (aminoketone-based), etc. (all yellow pigments), 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, 73, etc. (all orange pigments), C.I. 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, 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 (xanthene type, Organo Ultramarine, Bluish Red), 295 (monoazo type), 296 (diazo type),297 (aminoketone system) and the like (above, red pigments), C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64 (phthalocyanine system), 65 (phthalocyanine system), 66 (phthalocyanine system) and the like (above, green pigments), C.I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60 (triarylmethane system), 61 (xanthene system) and the like (above, purple pigments), 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 (monoazo type), 88 (methine type), etc. (all blue pigments).
[0158] 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 2020-070426 A, and the diarylmethane compounds described in JP 2020-504758 A can also be used.
[0159] As the blue colorant, an aluminum phthalocyanine compound having a phosphorus atom can also be used. 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.
[0160] 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.
[0161] As the red colorant, the compound described in paragraph 0034 of WO 2022 / 085485 and the brominated diketopyrrolopyrrole compound described in JP-A 2020-085947 can also be used.
[0162] 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. Furthermore, the dyes can also include thiazole compounds described in JP-A-2012-158649, azo compounds described in JP-A-2011-184493, and azo compounds described in JP-A-2011-145540.
[0163] 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, Halide zinc phthalocyanine described in Publication No. 2021 / 250883, quinophthalone compound represented by formula 1 of Korean Patent Publication No. 10-2020-0030759, polymer dye described in Korean Patent Publication No. 10-2020-0061793, 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 2022 / 136308, perylene compounds described in Chinese Patent Application Publication No. 113061349, Korean Patent Publication No. 10-2017-0018993 Cyan pigments described in the publication, isoindoline compounds described in JP 2020-180176 A, compounds described in JP 2023-013209 A, compounds described in JP 2023-013166 A, xanthene compounds described in WO 2023 / 286526, compounds described in JP 2021-155746 A, compounds described in JP 2021-155747 A, compounds described in JP 2021-155748 A, compounds described in JP 2021-155749 A, compounds described in WO 2018 / 051876, compounds described in JP 2020-083981 A, compounds described in JP 2023-056463 A, compounds described in JP-T-2023-515473 A can also be used. The chromatic colorant may be a rotaxane, and the dye skeleton may be used in the cyclic structure of the rotaxane, in the rod-like structure, or in both structures.
[0164] When the composition of the present invention contains a chromatic colorant, the content of the chromatic colorant in the total solid content of the composition is preferably 1 to 50 mass %. When the composition of the present invention contains two or more chromatic colorants, the total amount thereof is preferably within the above range.
[0165] When the composition of the present invention is used for an infrared cut filter, it is preferable that the composition of the present invention is substantially free of a chromatic colorant. Note that, "the composition of the present invention is substantially free of a chromatic colorant" means that the content of the chromatic colorant in the total solid content of the composition is 0.5% by mass or less, preferably 0.1% by mass or less, and more preferably contains no chromatic colorant.
[0166] <<Coloring material that transmits infrared light and blocks visible light>> The composition of the present invention may also contain a coloring material that transmits infrared light and blocks visible light (hereinafter also referred to as a coloring material that blocks visible light). A composition containing a coloring material that blocks visible light is preferably used as a composition for forming an infrared transmission filter.
[0167] The coloring material that blocks visible light is preferably a coloring material that absorbs light in the violet to red wavelength region. Furthermore, the coloring material that blocks visible light is preferably a coloring material that blocks light in the wavelength region of 450 to 650 nm. Furthermore, the coloring material that blocks visible light is preferably a coloring material that transmits light in the wavelength region of 900 to 1500 nm. The coloring material that blocks visible light preferably satisfies at least one of the following requirements (A) and (B): (A): Contains two or more types of chromatic coloring agents, and forms black by combining two or more types of chromatic coloring agents. (B): Contains an organic black coloring agent.
[0168] Examples of chromatic colorants include those described above. Examples of organic black colorants include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, with bisbenzofuranone compounds and perylene compounds being preferred. Examples of bisbenzofuranone compounds include compounds described in JP-A-2010-534726, JP-A-2012-515233, and JP-A-2012-515234, and are available, for example, as "Irgaphor Black" manufactured by BASF. Examples of perylene compounds include compounds described in paragraphs 0016 to 0020 of JP-A-2017-226821, C.I. Pigment Black 31, 32, and the like. Examples of the azomethine compound include compounds described in JP-A Nos. 01-170601 and 02-034664, and are available as "Chromofine Black A1103" manufactured by Dainichiseika Color & Chemicals Co., Ltd.
[0169] When a black color is formed by combining two or more chromatic colorants, the combination of chromatic colorants may include, for example, the following embodiments (1) to (8): (1) An embodiment containing a yellow colorant, a blue colorant, a violet colorant, and a red colorant; (2) An embodiment containing a yellow colorant, a blue colorant, and a red colorant; (3) An embodiment containing a yellow colorant, a violet colorant, and a red colorant; (4) An embodiment containing a yellow colorant and a violet colorant; (5) An embodiment containing a green colorant, a blue colorant, a violet colorant, and a red colorant; (6) An embodiment containing a violet colorant and an orange colorant; (7) An embodiment containing a green colorant, a violet colorant, and a red colorant; (8) An embodiment containing a green colorant and a red colorant.
[0170] When the composition of the present invention contains a coloring material that blocks visible light, the content of the coloring material that blocks visible light in the total solid content of the composition is preferably 1 to 50 mass %. The lower limit is preferably 5 mass % or more, more preferably 10 mass % or more, even more preferably 20 mass % or more, and particularly preferably 30 mass % or more.
[0171] When the composition of the present invention is used for an infrared cut filter, it is preferable that the composition of the present invention is substantially free of a coloring material that blocks visible light. Here, "the composition of the present invention is substantially free of a coloring material that blocks visible light" means that the content of the coloring material that blocks visible light in the total solid content of the composition is 0.5% by mass or less, preferably 0.1% by mass or less, and more preferably contains no coloring material that blocks visible light.
[0172] <<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.
[0173] As the fluorine-based surfactant, compounds described in paragraphs 0167 to 0173 of WO 2022 / 085485 can be used.
[0174] Examples of nonionic surfactants include the compounds described in paragraph 0174 of WO 2022 / 085485.
[0175] 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.
[0176] 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. The composition may contain only one type of surfactant, or may contain two or more types. When two or more types are contained, the total amount thereof is preferably within the above range.
[0177] <<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), and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.), 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 mass%. The composition may contain only one type of polymerization inhibitor, or two or more types. When two or more types are contained, the total amount thereof is preferably within the above range.
[0178] <<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. In addition, examples of functional groups other than the hydrolyzable group include a vinyl group, a styryl 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. The composition may contain only one type of silane coupling agent, or may contain two or more types. When two or more types are contained, it is preferable that the total amount thereof is within the above range.
[0179] <<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, The compounds described in paragraphs 0022 to 0024 of WO 2021 / 132247, the compounds described in paragraph 0179 of WO 2022 / 085485, the reactive triazine ultraviolet absorbers described in JP 2021-178918 A, the ultraviolet absorbers described in JP 2022-007884 A, the compounds described in Korean Patent Publication No. 10-2022-0014454, the compounds described in JP 2023-013321 A, the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 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 composition may contain only one type of ultraviolet absorber, or may contain two or more types.When two or more types are contained, the total amount thereof is preferably within the above range.
[0180] <<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 composition may contain only one antioxidant or two or more antioxidants. When two or more antioxidants are contained, the total amount thereof is preferably within the above range.
[0181] <<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.
[0182] 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.
[0183] 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.
[0184] 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.
[0185] <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.
[0186] <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.
[0187] 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 "Dispersion Technology and Industrial Applications Focused on Suspension (Solid / Liquid Dispersion System) - Comprehensive Data Collection," 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 on 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.
[0188] 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.
[0189] <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, but examples include 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, it 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 more.
[0190] 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.
[0191] 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.
[0192] 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.).
[0193] 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.
[0194] When the film of the present invention is used as an infrared cut filter, it is preferable that the film of the present invention 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). Furthermore, the average transmittance in the wavelength range of 700 to 720 nm is preferably 10% or less, more preferably 7% or less, even more preferably 4% or less, and particularly preferably 2% or less. Furthermore, 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. Furthermore, 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.
[0195] 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.
[0196] The film of the present invention can also be used in combination with a color filter containing a chromatic colorant. The color filter can be produced using a coloring composition containing a chromatic colorant. When the film of the present invention is used as an infrared cut filter and is used in combination with the film of the present invention and a color filter, it is preferable that the color filter is arranged on the optical path of the film of the present invention. For example, it is preferable to use the film of the present invention and a color filter stacked together to form a laminate. In the laminate, the film of the present invention and the color filter may or may not be adjacent to each other in the thickness direction. When the film of the present invention and the color filter are not adjacent to each other in the thickness direction, the film of the present invention may be formed on a support other than the support on which the color filter is formed, and other members constituting a solid-state imaging device (e.g., microlenses, planarization layers, etc.) may be interposed between the film of the present invention and the color filter.
[0197] 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.
[0198] <Method for Producing Film> The film of the present invention can be produced through a step of applying the composition of the present invention.
[0199] 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.
[0200] 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.
[0201] 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.
[0202] (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.
[0203] 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.
[0204] 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.
[0205] 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).
[0206] 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.
[0207] 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.
[0208] 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.
[0209] 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.
[0210] (When forming a pattern by a dry etching method) Pattern formation by a dry etching method can be performed by a method such as applying the composition to a support to form a composition layer, curing the formed composition layer to form a cured layer, then forming a patterned photoresist layer on the cured layer, and then dry etching the cured layer using an etching gas as a mask. 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 thereof are incorporated herein by reference.
[0211] <Optical Filter> The optical filter of the present invention has the above-described film of the present invention. Types of optical filters include infrared cut filters and infrared transmission filters.
[0212] 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).
[0213] 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.
[0214] <Solid-state imaging device> The solid-state imaging device of the present invention has the above-described film of the present invention. The configuration of the solid-state imaging device is not particularly limited as long as it has a configuration having the film of the present invention and functions as a solid-state imaging device. For example, the following configurations can be mentioned.
[0215] 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.
[0216] <Image Display Device> The image display device of the present invention has the film of the present invention. 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 have 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.
[0217] <Infrared Sensor> The infrared sensor of the present invention has the above-described film of the present invention. 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 of the present invention will be described with reference to the drawings.
[0218] 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.
[0219] 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 specification 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.
[0220] 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.
[0221] <Camera Module> The camera module of the present invention has the above-described film of the present invention. The configuration of the camera module is not particularly limited as long as it has a configuration including 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.
[0222] <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.
[0223] <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.
[0224] <Compound> The compound of the present invention is a compound represented by formula (1a). 1 ] s [A 1 n- ] t ...(1a) In formula (1a), Z 1 represents a monovalent cation represented by the above formula (SQ-1) or formula (CR-1), and A 1 n-represents an n-valent counter anion, the n-valent counter anion being an anion of a compound containing at least one atom selected from the group consisting of a tungsten atom, a molybdenum atom, a silicon atom, and a phosphorus atom, and an oxygen atom, n represents an integer of 2 or more, s represents an integer of 2 or more, t represents an integer of 1 or more, and s = n × t;
[0225] Z in formula (1a) 1 is Z in formula (1). 1 The n, s, and t in formula (1a) have the same meanings as the n, s, and t in formula (1), and the preferred ranges are also the same.
[0226] A in formula (1a) 1 n- represents an n-valent counter anion, which is an anion of a compound containing at least one atom selected from the group consisting of a tungsten atom, a molybdenum atom, a silicon atom, and a phosphorus atom, and an oxygen atom. For the anion of a compound containing at least one atom selected from the group consisting of a tungsten atom, a molybdenum atom, a silicon atom, and a phosphorus atom, and an oxygen atom, A in formula (1) n- The anions are the same as those described above, and the preferred ranges are also the same.
[0227] The compound represented by formula (1a) can be used as an infrared absorber.
[0228] Specific examples of the compound represented by formula (1a) include compounds A-1 to A-3, A-6 to A-16, A-18, A-19, A-21, A-22, A-24, and A-26 shown as specific examples of the specific infrared absorbing dye.
[0229] 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 as long as they do not deviate from the spirit of the present invention. In the structural formulas shown below, Me represents a methyl group, and Ph represents a phenyl group. <Synthesis Examples> (Synthesis Example 1) Synthesis of Compound A-1 Compound A-1 was synthesized from Compound A-1a synthesized with reference to JP 2022-189736 A according to the following synthesis route.
[0230] 2.0 g of compound A-1a and 100 mL of methanol were added to a flask and stirred at 20 to 30°C for 1 hour to obtain a solution 1a. 3 [P.W. 10 M 2 O 40 2.7 g of the compound A-1 was added to 20 mL of ion-exchanged water, and the mixture was stirred at 20°C to 30°C for 1 hour. 20 mL of methanol was then added and the mixture was stirred at 20°C to 30°C for 2 hours to obtain solution 1b. Solution 1b was added dropwise to solution 1a, and the mixture was stirred at 20°C to 30°C for 12 hours. The resulting precipitate was collected by filtration, washed twice with 50 mL of ion-exchanged water, and then washed twice with 50 mL of methanol. The collected crystals were dried at 50°C for 24 hours to obtain 3.4 g of compound A-1. The obtained compound A-1 was decomposed by wet ashing using an UltraWAVE (manufactured by Milestone General) in the presence of 70% nitric acid, and the resulting decomposition product was measured using an ICP (inductively coupled plasma) mass spectrometer (manufactured by Agilent Technologies, Agilent 7700s). Furthermore, the tungsten content and molybdenum content of Compound A-1 were quantified by the absolute calibration curve method. The theoretical values of the tungsten content and molybdenum content of Compound A-1 were consistent with the measured values of the tungsten content and molybdenum content obtained by ICP mass spectrometry. Therefore, it was concluded that the counter anion of Compound A-1 was [PW 10 M 2 O 40 ] 3- It was confirmed that this is the case.
[0231] (Synthesis Example 2) Synthesis of Compound A-11 Compound A-11 was synthesized from compound A-11a synthesized with reference to JP-A-2022-189736 according to the following synthesis route. 2.0 g of compound A-11a and 100 mL of methanol were added to a flask and stirred at 20 to 30°C for 1 hour to obtain a solution 11a. 3 [P.W. 12 O 402.5 g of ] was added to 20 mL of ion-exchanged water, and the mixture was stirred at 20°C to 30°C for 1 hour. 20 mL of methanol was further added and the mixture was stirred at 20°C to 30°C for 2 hours, to obtain solution 11b. Solution 11b was added dropwise to solution 11a, and the mixture was stirred at 20°C to 30°C for 12 hours. The resulting precipitate was collected by filtration, washed twice with 50 mL of ion-exchanged water, and then washed twice with 50 mL of methanol. The collected crystals were dried at 50°C for 24 hours to obtain 3.3 g of compound A-11. Furthermore, the tungsten content of the obtained compound A-11 was quantified in the same manner as for compound A-1. As a result, the theoretical value of the tungsten content contained in compound A-11 and the measured value of the tungsten content obtained by ICP mass spectrometry agreed, and therefore, the counter anion of compound A-11 was determined to be [PW 12 O 40 ] 3- It was confirmed that this is the case.
[0232] (Synthesis Example 3) Synthesis of Compound A-26 Compound A-26 was synthesized from Compound A-26a, which was synthesized with reference to Japanese Patent No. 6958569 and JP-A No. 2022-189736, according to the following synthesis route.
[0233] 2.0 g of compound A-26a and 100 mL of methanol were added to a flask and stirred at 20 to 30°C for 1 hour to obtain a solution 26a. 3 [P.W. 10 M 2 O 402.6 g of ] was added to 20 mL of ion-exchanged water, and the mixture was stirred at 20°C to 30°C for 1 hour. 20 mL of methanol was further added, and the mixture was stirred at 20°C to 30°C for 2 hours, to obtain solution 26b. Solution 26b was added dropwise to solution 26a, and the mixture was stirred at 20°C to 30°C for 12 hours. The resulting precipitate was collected by filtration, washed twice with 50 mL of ion-exchanged water, and then washed twice with 50 mL of methanol. The collected crystals were dried at 50°C for 24 hours to obtain 3.0 g of compound A-26. Furthermore, the tungsten content and molybdenum content of the obtained compound A-26 were quantified in the same manner as for compound A-1. As a result, the theoretical values of the tungsten content and molybdenum content contained in compound A-26 and the measured values of the tungsten content and molybdenum content obtained by ICP mass spectrometry agreed, and therefore the counter anion of compound A-26 was determined to be [PW 10 M 2 O 40 ] 3- It was confirmed that this is the case.
[0234] <Preparation of Dispersion> The pigments, pigment derivatives, dispersing resins, and solvents of the types shown in the table below were mixed in the parts by mass shown below, and 117 parts by mass of zirconia beads with a diameter of 0.3 mm were added thereto. The mixture was subjected to a dispersion treatment for 5 hours using a paint shaker, and the beads were separated by filtration to prepare a dispersion. The infrared absorber used had been subjected to the following kneading and polishing treatment.
[0235] (Kneading and Polishing Treatment Conditions) 10.6 parts by mass of pigment, 149.4 parts by mass of grinding agent, and 28 parts by mass of binder were added to a Laboplastomill (manufactured by Toyo Seiki Seisakusho, Ltd.), and the temperature of the kneaded material in the device was controlled to 70°C, and kneading was carried out for 2 hours. The grinding agent was neutral anhydrous Glauber's salt E (average particle size (volume-based 50% diameter (D50)) = 20 μm, manufactured by Mitajiri Chemical Industry Co., Ltd.), and the binder was diethylene glycol. After kneading and polishing, the kneaded material was washed with 20 L of water at 24°C to remove the grinding agent and binder, and then treated in a heating oven at 80°C for 24 hours.
[0236]
[0237] The materials listed in the table above are as follows: (Pigments) A-1 to A-26: Compounds A-1 to A-26 shown as specific examples of the specific infrared absorbing dyes described above PR254: C.I. Pigment Red 254 (diketopyrrolopyrrole compound, red pigment) PB15:6: C.I. Pigment Blue 15:6 (phthalocyanine compound, blue pigment) PV23: C.I. Pigment Violet 23 (dioxazine compound, purple pigment) PY138: C.I. Pigment Yellow 138 (quinophthalone compound, yellow pigment) IR-1: Compound having the following structure (squarylium compound, infrared absorber) IR-2: Compound having the following structure (squarylium compound, infrared absorber) IR-3: Compound having the following structure (croconium compound, infrared absorber) IR-4: Compound having the following structure (naphthalocyanine compound, infrared absorber) IR-5: Compound having the following structure (pyrrolopyrrole compound, infrared absorber) IR-6: Mixture of the following structures (IR-6-a):(IR-6-b):(IR-6-c) in a ratio of 81:17:2 (indigo compound, infrared absorber) IR-7: a mixture of the following structures (IR-7-a): {(IR-7-b) + (IR-7-c)}: (IR-7-d): (IR-7-e) in a ratio of 7:19:59:15 (partial naphthalocyanine compound, infrared absorber)
[0238] (Pigment derivative) Syn-1: Compound having the following structure
[0239] (Dispersion Resins) D-1: Resin having the following structure (acid value 99.1 mgKOH / g, weight average molecular weight 38,000). The numbers attached to the main chain represent the molar ratio of repeating units, and the numbers attached to the side chain represent the number of repeating units. D-2: Resin having the following structure (acid value 87.0 mgKOH / g, weight average molecular weight 18,000). The numbers attached to the main chain represent the molar ratio of repeating units, and the numbers attached to the side chain represent the number of repeating units. D-3: Resin having the following structure (acid value 85.0 mgKOH / g, weight average molecular weight 22,000). The numbers attached to the main chain represent the molar ratio of repeating units, and the numbers attached to the side chain represent the number of repeating units. D-4: Resin having the following structure (acid value 43 mgKOH / g, weight average molecular weight 9,000). The numbers attached to the side chain represent the molar ratio of repeating units. D-5: Block type resin having the following structure (amine value 90 mg KOH / g, quaternary ammonium salt value 30 mg KOH / g, weight average molecular weight 9800). The numbers attached to the main chain represent the molar ratio of repeating units. D-6: Resin having the following structure (acid value 32.3 mg KOH / g, amine value 45.0 mg KOH / g, weight average molecular weight 22900). The numbers attached to the main chain represent the molar ratio of repeating units, and the numbers attached to the side chains represent the number of repeating units. D-7: Block type resin having the following structure (amine value 50 mg KOH / g, quaternary ammonium salt value 20 mg KOH / g, weight average molecular weight 9800). The numbers attached to the main chain represent the molar ratio of repeating units.
[0240] (Solvent) S-1: Propylene glycol monomethyl ether acetate (PGMEA)
[0241] <Preparation of Compositions> The materials shown in the table below were mixed in the parts by mass shown in the table below, and then filtered through a nylon filter with a pore size of 0.45 μm (manufactured by Nippon Pall Co., Ltd.) to prepare each composition.
[0242]
[0243]
[0244]
[0245]
[0246]
[0247]
[0248] (Dispersions) Dispersions 1 to 31, Dispersion R1, Dispersion B1, Dispersion V1, Dispersion Y1, Dispersions IR1 to IR7: the above-mentioned Dispersions 1 to 31, Dispersion R1, Dispersion B1, Dispersion V1, Dispersion Y1, and Dispersions IR1 to IR7
[0249] (Infrared absorbers) IR-8: Compound having the following structure (squarylium compound) IR-9: Compound having the following structure (polymethine compound) IR-10: Compound having the following structure (iminium compound) Z-1: Compound having the following structure (squarylium compound synthesized by the method described in paragraph 0109 of JP-A No. 2022-189736)
[0250] (Resins (binders)) B-1: Resin having the following structure (the numbers attached to the main chain are the molar ratios of repeating units, weight average molecular weight 17,000, dispersity 2.3) B-2: Resin having the following structure (the numbers attached to the main chain are the molar ratios of repeating units, weight average molecular weight 9,700, dispersity 1.8) B-3: Resin having the following structure (the numbers attached to the main chain are the molar ratios of repeating units, weight average molecular weight 10,100, dispersity 1.7) B-4: Resin having the following structure (the numbers attached to the main chain are the molar ratios of repeating units, weight average molecular weight 25,000, dispersity 2.2) B-5: Resin having the following structure (weight average molecular weight 137,000, number average molecular weight 32,000, glass transition temperature 165°C) B-6: Resin having the following structure (weight average molecular weight 188,000, number average molecular weight 75,000, glass transition temperature 285°C) B-7: Resin having the following structure (glass transition temperature: 310°C, inherent viscosity: 0.87)
[0251] (Photopolymerization initiators) I-1 to I-6: Compounds having the following structures
[0252] (Polymerizable Compounds) M-1: KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd., a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate) M-2: ARONIX M-510 (manufactured by Toagosei Co., Ltd., a polybasic acid-modified acrylic oligomer)
[0253] (Surfactants) F-1: FTX-218D (manufactured by Neos Corporation, fluorochemical surfactant) F-2: Compound having the following structure (weight average molecular weight 14,000, % indicating the proportion of repeating units is mol %) F-3: Megafac F-554 (manufactured by DIC Corporation, fluorine-based surfactant) F-4: KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd., silicone-based surfactant)
[0254] (Polymerization inhibitor) G-1: p-methoxyphenol
[0255] (Additives) U-1 to U-6: Compounds having the following structure (antioxidants)
[0256] P-1: Trimellitic acid (hardening agent) P-2: 2-ethyl-4-methylimidazole (hardening agent) P-3: Methyltetrahydrophthalic anhydride (hardening agent)
[0257] UV-1: Uvinul 3050 (manufactured by BASF, compound having the following structure, ultraviolet absorber) UV-2: Tinuvin 477 (manufactured by BASF, hydroxyphenyltriazine-based ultraviolet absorber) UV-3: Tinuvin 326 (manufactured by BASF, compound having the following structure, ultraviolet absorber) UV-4: compound having the following structure (ultraviolet absorber)
[0258] (Epoxy compounds) E-1: Resin having the following structure (the numerical values of repeating units are mass ratios, weight average molecular weight 20,000, number average molecular weight 8,300, epoxy equivalent 284 g / eq, acid value 130 mg KOH / g, glass transition temperature 136°C) E-2: Resin having the following structure (the numerical values of repeating units are mass ratios, weight average molecular weight 26,100, number average molecular weight 8,600, epoxy equivalent 355 g / eq, acid value 163 mg KOH / g, glass transition temperature 133°C) E-3: Resin having the following structure (the numerical values of repeating units are mass ratios, weight average molecular weight 21,100, number average molecular weight 8,500, epoxy equivalent 355 g / eq, acid value 130 mg KOH / g, glass transition temperature 157°C) E-4: Resin having the following structure (the numerical values of repeating units are mass ratios, weight average molecular weight 18,300, number average molecular weight 9,100, epoxy equivalent 284 g / eq, acid value 98 mg KOH / g, glass transition temperature 134°C) E-5: Resin having the following structure (the numerical values of repeating units are mass ratios, weight average molecular weight 22,900, number average molecular weight 8,800, epoxy equivalent 316 g / eq, acid value 130 mg KOH / g, glass transition temperature 124°C)
[0259] (Solvent) S-1: Propylene glycol monomethyl ether acetate (PGMEA) S-2: Propylene glycol monomethyl ether (PGME) S-3: Cyclopentanone S-4: Cyclohexanone
[0260] <Film Production> (Production Example 1) Method for producing films using the compositions of Examples 1 to 53 and Comparative Example 1 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 an i-line stepper exposure system FPA-3000i5+ (manufactured by Canon Corporation) at 1000 mJ / cm 2 The entire surface was exposed to an exposure amount of 1.0 μm. Then, the film was heated at 180° C. for 5 minutes using a hot plate to produce a film having a thickness of 1.0 μm.
[0261] (Production Example 2) Method for producing films using the compositions of Examples 101 to 150 and Comparative Example 101 Each composition was applied to a glass substrate by spin coating, heated on a hot plate at 100°C for 2 minutes, and then heated at 200°C for 8 minutes for curing treatment, to obtain a film with a thickness of 1.0 μm.
[0262] (Production Example 3) Method for producing films using the compositions of Examples 201 to 250 and Comparative Example 201 Each composition was applied to a glass substrate by spin coating, heated on a hot plate at 100°C for 2 minutes, and then heated at 180°C for 5 minutes to produce a film with a thickness of 1.0 μm.
[0263] <Performance Evaluation> (Lightfastness) The obtained film was irradiated with light at 100,000 Lux for 30 hours using a xenon arc lamp lightfastness tester. The transmittance of the film in the wavelength range of 400 to 1500 nm before and after light irradiation was measured, and the spectral fluctuation rate ΔT was calculated using the following formula, and the lightfastness was evaluated according to the following criteria. Spectral fluctuation rate ΔT = ((T02 - T12) / T02) x 100 T02: Transmittance of the film at the maximum absorption wavelength in the wavelength range of 400 to 1500 nm before light irradiation T12: Transmittance of the film at the wavelength at which T02 was measured after light irradiation Evaluation criteria A: Spectral fluctuation rate ΔT is less than 5% B: Spectral fluctuation rate ΔT is 5% or more but less than 10% C: Spectral fluctuation rate ΔT is 10% or more but less than 15% D: Spectral fluctuation rate ΔT is 15% or more
[0264] (Heat Resistance) A heat resistance test was conducted by heating the obtained film at 265°C for 5 minutes using a hot plate. The transmittance of the film in the wavelength range of 400 to 1500 nm was measured before and after the heat resistance test, and the change in transmittance at each wavelength was calculated using the following formula. The heat resistance was evaluated according to the following criteria using the maximum value of the change in transmittance in the wavelength range of 400 to 1500 nm. Transmittance change = | (Transmittance of film before heat resistance test - Transmittance of film after heat resistance test) | - Evaluation criteria - A: The maximum value of the change in transmittance is less than 5% B: The maximum value of the change in transmittance is more than 5% and less than 7% C: The maximum value of the change in transmittance is more than 7% and less than 10% D: The maximum value of the change in transmittance is more than 10%
[0265]
[0266]
[0267]
[0268] As shown in the above table, the examples were excellent in heat resistance and light resistance.
[0269] The spectral properties of the films produced from the compositions of Examples 1 to 53 by the method of Production Example 1 were measured, and the films had excellent visible transparency with an average transmittance of 90% or more in the wavelength range of 420 to 550 nm. Furthermore, the films had a maximum absorption wavelength longer than 700 nm, and the transmittance at the maximum absorption wavelength was 5% or less, indicating excellent infrared shielding properties.
[0270] The spectral properties of the films produced from the compositions of Examples 101 to 150 by the method of Production Example 2 were measured, and the films had an average transmittance of 90% or more in the wavelength range of 420 to 550 nm, indicating excellent visible transparency. Furthermore, the films had a maximum absorption wavelength longer than 700 nm, and the transmittance at the maximum absorption wavelength was 5% or less, indicating excellent infrared shielding properties.
[0271] The spectral properties of the films produced from the compositions of Examples 201 to 250 by the method of Production Example 2 were measured, and the films had an average transmittance of 90% or more in the wavelength range of 420 to 550 nm, indicating excellent visible transparency. Furthermore, the films had a maximum absorption wavelength longer than 700 nm, and the transmittance at the maximum absorption wavelength was 5% or less, indicating excellent infrared shielding properties.
[0272] The storage stability of the compositions of Examples 1, 11, 22, 30, 38, 44, 48, 51, 101, and 201 was evaluated by the following method. According to the evaluation criteria shown below, the composition of Example 1 was rated A, the composition of Example 11 was rated B, the composition of Example 22 was rated A, the composition of Example 30 was rated A, the composition of Example 38 was rated B, the composition of Example 44 was rated A, the composition of Example 48 was rated A, the composition of Example 51 was rated A, the composition of Example 101 was rated A, and the composition of Example 201 was rated A. The storage stability of each composition was at a level that presented no practical problems.
[0273] (Method for evaluating storage stability) The viscosity of the composition immediately after production (initial viscosity A) was measured. The composition after viscosity measurement was stored in a thermostatic bath at 45°C for 72 hours, and then the viscosity (post-storage viscosity B) was measured again. The viscosity was measured by adjusting the temperature of the composition to 23°C. The viscosity increase rate was calculated using the following formula, and storage stability was evaluated according to the following criteria. A lower viscosity increase rate indicates better storage stability. Viscosity increase rate (%) = |(post-storage viscosity B / initial viscosity A) - 1| x 100. The evaluation criteria are as follows. A and B are levels that are not problematic in practical use. A: viscosity increase rate is 5% or less B: viscosity increase rate is more than 5% but not more than 10% C: viscosity increase rate is more than 10%
[0274] 110: solid-state imaging element, 111: infrared cut filter, 112: color filter, 114: infrared transmission filter, 115: microlens, 116: planarization layer
Claims
1. A composition comprising an infrared absorbing dye represented by formula (1), a curable compound, and a solvent; 1 ] s [A n- ] t ...(1) In formula (1), Z 1 represents a monovalent cation represented by formula (SQ-1) or formula (CR-1); A n- represents an n-valent counter anion, n represents an integer of 2 or more, s represents an integer of 2 or more, t represents an integer of 1 or more, and s = n x t; In the formula, R A and R C each independently represents a hydrogen atom or a substituent; R B is -OR b1 , -OC(=O)R b1 , -OC(=O)NR b2 R b3 , -NR b2 R b3 , -NHC(=O)R b1 , -NHC(=O)OR b1 , -NHC(=O)NR b2 R b3 , -NHS(=O) 2 R b1 , -SR b1 Or -S(=O) 2 R b1 represents R b1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group; R b2 and R b3 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R b2 and R b3 may be bonded to form a ring; T 1 is expressed by the formula (T 1A ), formula (T 1B ), formula (T 1C ) or the formula (T 1D ) represents a group represented by the formula: T 2 is the formula (T 2A ), formula (T 2B ), formula (T 2C ) or the formula (T 2D ) represents a group represented by the formula: In the formula, X 1 ~X 8 each independently represents an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, or -NR X1 - represents R X1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a heterocyclic group; R 1 ~R 20 and R 31 ~R 50 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, a nitro group, a cyano group, -OR L1 , -C(=O)R L1 , -C(=O)OR L1 , -OC(=O)R L1 , -NR L1 R L2 , -NHC(=O)R L1 , -C(=O)NR L1 R L2 , -NHC(=O)OR L1 , -OC(=O)NR L1 R L2 , -NHC(=O)NR L1 R L2 , -SR L1 , -S(=O) 2 R L1 , -S(=O) 2 OR L1 , -NHS(=O) 2 R L1 Or -S(=O) 2 N.R. L1 R L2 represents L1 and R L2 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group; R L1 and R L2 may be bonded to form a ring, R 1 ~R 20 and R 31 ~R 50 adjacent two of R may be bonded to each other to form a ring; T1 and R T2 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a heterocyclic group.
2. Z in the formula (1) 1 The composition according to claim 1, wherein is a monovalent cation represented by formula (SQ-1):
3. T in the above formula (SQ-1) 1 is the formula (T 1A ) or the formula (T 1B ) is a group represented by T 2 is the formula (T 2A ) or the formula (T 2B The composition according to claim 2, wherein the group is a group represented by the formula:
4. A in the above formula (1) n- The composition according to claim 1 or 2, wherein: is an anion of a compound containing at least one atom selected from the group consisting of a tungsten atom, a molybdenum atom, a silicon atom, and a phosphorus atom, and an oxygen atom.
5. The composition according to claim 1 or 2, further comprising at least one selected from the group consisting of a chromatic colorant and an infrared absorbing agent other than the infrared absorbing dye represented by formula (1).
6. A film obtained using the composition according to claim 1 or 2.
7. An optical filter comprising the film according to claim 6.
8. A solid-state imaging device having the film according to claim 6.
9. An image display device having the film according to claim 6.
10. An infrared sensor having the film according to claim 6.
11. A camera module comprising a membrane according to claim 6.
12. A compound represented by formula (1a); 1 ] s [A 1 n- ] t ...(1a) In formula (1a), Z 1 represents a monovalent cation represented by formula (SQ-1) or formula (CR-1); A 1 n- represents an n-valent counter anion, the n-valent counter anion being an anion of a compound containing at least one atom selected from the group consisting of a tungsten atom, a molybdenum atom, a silicon atom, and a phosphorus atom, and an oxygen atom, n represents an integer of 2 or more, s represents an integer of 2 or more, t represents an integer of 1 or more, and s = n × t; In the formula, R A and R C each independently represents a hydrogen atom or a substituent; R B is -OR b1 , -OC(=O)R b1 , -OC(=O)NR b2 R b3 , -NR b2 R b3 , -NHC(=O)R b1 , -NHC(=O)OR b1 , -NHC(=O)NR b2 R b3 , -NHS(=O) 2 R b1 , -SR b1 Or -S(=O) 2 R b1 represents R b1 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group; R b2 and R b3 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group; R b2 and R b3 may be bonded to form a ring; T 1 is expressed by the formula (T 1A ), formula (T 1B ), formula (T 1C ) or the formula (T 1D ) represents a group represented by the formula: T 2 is the formula (T 2A ), formula (T 2B ), formula (T 2C ) or the formula (T 2D ) represents a group represented by the formula: In the formula, X 1 ~X 8 each independently represents an oxygen atom, a sulfur atom, a selenium atom, a tellurium atom, or -NR X1 - represents R X1 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a heterocyclic group; R 1 ~R 20 and R 31 ~R 50 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, a nitro group, a cyano group, -OR L1 , -C(=O)R L1 , -C(=O)OR L1 , -OC(=O)R L1 , -NR L1 R L2 , -NHC(=O)R L1 , -C(=O)NR L1 R L2 , -NHC(=O)OR L1 , -OC(=O)NR L1 R L2 , -NHC(=O)NR L1 R L2 , -SR L1 , -S(=O) 2 R L1 , -S(=O) 2 OR L1 , -NHS(=O) 2 R L1 Or -S(=O) 2 N.R. L1 R L2 represents L1 and R L2 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group; R L1 and R L2 may be bonded to form a ring, R 1 ~R 20 and R 31 ~R 50 adjacent two of R may be bonded to each other to form a ring; T1 and R T2 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a heterocyclic group.
Citation Information
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