Absorbent

An organic absorbent with a specific cationic structure addresses the challenge of compatibility and heat resistance, ensuring stable optical properties in absorption films under high-temperature and high-humidity conditions.

JP2025096176AActive Publication Date: 2025-06-26LMS
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Patent Information

Application Number
JP2024203374
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Priority Date
2023-12-14
Filing Date
2024-11-21
Publication Date
2025-06-26
Estimated Expiration
2044-11-21

AI Technical Summary

Technical Problem

Existing absorbents face challenges in achieving excellent solubility or compatibility with various solvents and resin components, leading to suboptimal spectral characteristics and light characteristics when used in absorption films, especially under high-temperature and high-humidity conditions.

Method used

Development of an organic absorbent with a specific cationic structure, represented by Chemical Formula 1, which exhibits excellent heat resistance and compatibility with resin components and solvents, maintaining stable optical properties even under harsh conditions.

Benefits of technology

The absorbent ensures desired optical properties and heat resistance, effectively preventing deterioration of light characteristics in absorption films, even after exposure to high-temperature and high-humidity conditions.

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Abstract

To provide an organic absorbent which offers superior compatibility or solubility with various solvents and resin components and superior heat resistance, and thus allows its optical properties to be stably maintained even when kept in a high temperature condition or high temperature / high humidity condition, and to provide an absorption membrane with desired optical properties using the absorbent.SOLUTION: An absorbent comprising a cation represented by formula below is provided, where A1 through A3 in the formula may independently represent an alkyl group, alkynyl group, alkenyl group, or alkoxy group.SELECTED DRAWING: Figure 4
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Description

Technical Field

[0001] This specification discloses an absorbent and its uses.

Background Art

[0002] Absorbents, such as those capable of absorbing light in the infrared region, may be applied to various uses.

[0003] For example, in imaging devices using CCD (Charge-Coupled Device) or CMOS (complementary metal-oxide-semiconductor) image sensors, infrared sensors, etc., since they include silicon photodiodes having sensitivity to the near-infrared region, the absorbent may be used.

[0004] Although there are various ways to apply such absorbents, usually, a method using a coating solution obtained by mixing an absorbent dissolved in a solvent and a resin component is applied.

[0005] Therefore, it is necessary for the absorbent to exhibit excellent solubility or compatibility with both the solvent and the resin component.

[0006] When the solubility or compatibility of the absorbent with the solvent or resin component decreases, the desired spectral characteristics may not be obtained for the absorption film to which the absorbent is applied, or the light characteristics may deteriorate due to phenomena such as the precipitation of the absorbent in the absorption film.

[0007] However, it is a difficult problem to ensure an absorbent that exhibits excellent solubility or compatibility with various types of solvents and resin components at the same time.

[0008] Absorbents can be classified into inorganic absorbents and organic absorbents. In the case of organic absorbents, they are easy to apply, and it is also easy to control the wavelength of the absorbed light. Therefore, the transmittance of the desired light can be efficiently reduced.

[0009] However, since organic absorbents are less heat-resistant than inorganic absorbents, the optical properties of the absorbent or the film containing the absorbent may deteriorate after being exposed to high-temperature conditions or high-temperature and high-humidity conditions.

Summary of the Invention

Problems to be Solved by the Invention

[0010] This specification discloses an absorbent and its uses. The purpose of this specification is to disclose an absorbent that exhibits excellent compatibility or solubility with various solvents and resin components as an organic absorbent, has excellent heat resistance, and can stably maintain its optical properties even when held under high-temperature conditions or high-temperature and high-humidity conditions.

[0011] This specification also aims to disclose content that enables the desired optical properties to be ensured by applying the absorbent.

[0012] This specification further aims to disclose the uses of the absorbent.

Means for Solving the Problems

[0013] Among the physical properties mentioned in this specification, those for which the measurement temperature affects the results are, unless otherwise specified, the results measured at room temperature.

[0014] The term "room temperature" means the natural temperature without heating or cooling, for example, any temperature within the range of 10°C to 30°C, a temperature of about 23°C or about 25°C. Also, in this specification, the unit of temperature is Celsius (°C) unless otherwise specified.

[0015] Among the physical properties mentioned in this specification, those for which the measurement pressure affects the results are, unless otherwise specified, the results measured at normal pressure.

[0016] The term "normal pressure" means the natural pressure without pressurization or depressurization, and usually means a pressure of about 740 mmHg to 780 mmHg at the atmospheric pressure level.

[0017] When humidity among the physical properties mentioned in this specification affects the results, unless otherwise specified, the physical property is the one measured under the humidity in the standard state. The humidity in the standard state means any humidity within the range of 40% to 60% in relative humidity, for example, a relative humidity of about 40% or 60%.

[0018] When the optical properties (for example, refractive index) mentioned in this specification are properties that vary depending on the wavelength, unless otherwise specified, the optical property is the property with respect to light of a wavelength of 520 nm.

[0019] In this specification, unless otherwise specified, the terms transmittance, reflectance, or absorptance mean the actual transmittance (measured transmittance), actual reflectance (measured reflectance), or actual absorptance (measured absorptance) confirmed within a specific wavelength or a wavelength range of a predetermined region.

[0020] In this specification, unless otherwise specified, the terms transmittance, reflectance, or absorptance are the transmittance, reflectance, or absorptance based on an incident angle of 0 degrees.

[0021] In this specification, unless otherwise specified, the term average transmittance is the result obtained by measuring the transmittance at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength within a predetermined wavelength region and then calculating the arithmetic mean of the measured transmittances. For example, the average transmittance within the wavelength range of 350 nm to 360 nm is the arithmetic mean of the transmittances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

[0022] In this specification, the term maximum transmittance is the maximum transmittance when measuring the transmittance at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength within a predetermined wavelength region. For example, the maximum transmittance within the wavelength range of 350 nm to 360 nm is the highest transmittance among the transmittances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

[0023] In this specification, unless otherwise specified, the term "average reflectance" refers to the arithmetic mean of reflectances measured after measuring the reflectances at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength within a predetermined wavelength range. For example, the average reflectance within the wavelength range of 350 nm to 360 nm is the arithmetic mean of the reflectances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

[0024] In this specification, the term "maximum reflectance" refers to the maximum reflectance when measuring the reflectances at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength within a predetermined wavelength range. For example, the maximum reflectance within the wavelength range of 350 nm to 360 nm is the highest reflectance among the reflectances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

[0025] In this specification, unless otherwise specified, the term "average absorptance" refers to the arithmetic mean of absorptances measured after measuring the absorptances at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength within a predetermined wavelength range. For example, the average absorptance within the wavelength range of 350 nm to 360 nm is the arithmetic mean of the absorptances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

[0026] In this specification, the term "maximum absorptance" refers to the maximum absorptance when measuring the absorptances at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength within a predetermined wavelength range. For example, the maximum absorptance within the wavelength range of 350 nm to 360 nm is the highest absorptance among the absorptances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

[0027] In this specification, the incident angle is an angle based on the normal line of the surface to be evaluated. For example, the transmittance at an incident angle of 0 degrees of an optical filter means the transmittance for light incident in a direction substantially parallel to the normal line of the surface of the optical filter. Also, for example, an incident angle of 40 degrees is a value for incident light that forms a substantially 40-degree angle with the normal line in the clockwise or counterclockwise direction. Such a definition of the incident angle is similarly applied to other characteristics such as transmittance.

[0028] In this specification, the term alkyl group means an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms. The alkyl group may be linear, branched, or cyclic. The alkyl group may optionally be substituted by at least one substituent. Such content is applied to all alkyl groups mentioned in this specification unless otherwise specified.

[0029] In this specification, the term alkoxy group means an alkoxy group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms. The alkoxy group may be linear, branched, or cyclic. The alkoxy group may optionally be substituted by at least one substituent. Such content is applied to all alkoxy groups mentioned in this specification unless otherwise specified.

[0030] In this specification, the term alkenyl group means an alkenyl group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms. The alkenyl group may be linear, branched, or cyclic. The alkenyl group may optionally be substituted by at least one substituent. Such content is applied to all alkenyl groups mentioned in this specification unless otherwise specified.

[0031] As used herein, the term "alkynyl group" means an alkynyl group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms or 2 to 4 carbon atoms. The alkynyl group may be linear, branched or cyclic. The alkenyl group may optionally be substituted with at least one substituent. Such content applies to all alkynyl groups mentioned in this specification unless otherwise specified.

[0032] As used herein, the term "aryl group" means a monovalent residue derived from an aromatic hydrocarbon, and the aryl group may be an aryl group having 6 to 36 carbon atoms, 6 to 30 carbon atoms, 6 to 24 carbon atoms, 6 to 18 carbon atoms or 6 to 12 carbon atoms, and may be, for example, a phenyl group, a tolyl group, a xylyl group or a naphthyl group. The aryl group may also optionally be substituted with at least one substituent. Such content applies to all aryl groups mentioned in this specification unless otherwise specified.

[0033] As used herein, the term "arylalkyl group" means an alkyl group substituted with at least one or more of the above aryl groups. At this time, the specific types of the alkyl group and the aryl group are as described above. Such content applies to all arylalkyl groups mentioned in this specification unless otherwise specified.

[0034] As used herein, the term "alkylidene group" means a divalent functional group obtained by removing two hydrogens from an alkane, and means a functional group in which the hydrogen atom is removed from one carbon of the alkane. Such an alkylidene group may be an alkylidene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms. The alkylidene group may be linear, branched or cyclic. The alkylidene group may optionally be substituted with at least one substituent. Such content applies to all alkylidene groups mentioned in this specification unless otherwise specified.

[0035] As used herein, the term "alkylene group" refers to a divalent functional group obtained by removing two hydrogens from an alkane, where the hydrogen atoms are removed one by one from two different carbons of the alkane. Such an alkylene group may be an alkylene group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms. The alkylene group may be linear, branched, or cyclic. The alkylene group may optionally be substituted with at least one substituent. Such content applies to all alkylene groups mentioned in this specification unless otherwise specified.

[0036] As used herein, the term "alkenylene group" may be an alkenylene group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms. The alkenylene group may be linear, branched, or cyclic. The alkenylene group may optionally be substituted with at least one substituent. Such content applies to all alkenylene groups mentioned in this specification unless otherwise specified.

[0037] As used herein, the term "alkynylene group" may be an alkynylene group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms. The alkynylene group may be linear, branched, or cyclic. The alkynylene group may optionally be substituted with at least one substituent. Such content applies to all alkynylene groups mentioned in this specification unless otherwise specified.

[0038] This specification discloses an absorbent. As used herein, the term "absorbent" refers to a compound capable of absorbing light in any wavelength range.

[0039] The absorbent may be a compound containing a cation represented by Chemical Formula 1 below, or a compound containing a cation containing a site represented by Chemical Formula 1 below.

[0040] In Chemical Formula 1 below, due to the silyl group linked to the nitrogen atom, the absorbent can exhibit desired optical properties together with excellent heat resistance and excellent compatibility with the resin component and / or the solvent.

[0041]

Chemical Formula

[0042] In Chemical Formula 1, A1 to A3 may each independently be hydrogen, halogen, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryl group, or an arylalkyl group.

[0043] In Chemical Formula 1, L1 may be a divalent functional group represented by -U 1- T 1- U 2- T 2- U 3- In the divalent functional group, T1 and T2 may each independently be an oxygen atom or may not exist, and U1 to U3 may each independently be an alkylene group, an alkylidene group, an alkenylene group, or an alkynylene group or may not exist. In the above, the fact that a certain symbol does not exist means that the atoms on both sides of the symbol are directly linked. For example, in the above, other elements other than T1 exist and T1 does not exist, and the divalent functional group is -U 1- U 2- T 2- U 3- represented by.

[0044] In Chemical Formula 1, R1 and R2 form an absorption edge, and among R3 to R8, R3 to R6 or R5 to R8 may form an absorption edge.

[0045] In the above, the fact that an absorption edge is formed means that the absorbent has a structure capable of exhibiting the property of absorbing light of a desired wavelength as a whole due to the structure formed by the substituent or the structure formed at the position where the substituent exists.

[0046] The absorption end will be described later.

[0047] In Chemical Formula 1, among R3 to R8, other substituents that do not form the absorption end may each independently be hydrogen, a halogen, a hydroxy group, a cyano group, a nitro group, a carboxyl group, an alkyl group, an alkoxy group, an aryl group, an arylalkyl group, an alkylcarbonylamino group, an arylalkylcarbonylamino group, an alkylsulfonylamino group, a haloalkylsulfonylamino group, an arylalkylsulfonylamino group or an amino group.

[0048] In Chemical Formula 1, the dotted line indicates whether the dotted line is a single bond between nitrogen and carbon or a double bond between nitrogen and carbon.

[0049] When the dotted line in Chemical Formula 1 is a double bond between nitrogen and carbon, R2 among R1 and R2 does not exist, and R1 forms the absorption end. Further, when the dotted line is a double bond between nitrogen and carbon, the nitrogen atom in Chemical Formula 1 becomes a cationic site.

[0050] The absorption end means a site that enables the absorbent to have a structure capable of absorbing light of a desired wavelength as a whole. For example, the absorption end may be a skeleton or structure having a so-called resonance structure and / or a conjugated bond.

[0051] It is known that the absorption of light by an absorbent, particularly an organic absorbent, is caused by the energy difference (ΔE) between the ground state and the excited state, and this difference is also explained by the energy difference between the HOMO (Highest Occupied Molecular Orbital) and the LUMO (Lowest Unoccupied Molecular Orbital).

[0052] Generally, an organic absorbent contains a resonance structure and / or a conjugated bond as an absorption edge capable of exhibiting a light absorption effect. As a result, when the dotted line in Chemical Formula 1 is a double bond, R1 and R2 (R1 in this case) and R3 to R6 or R5 to R8 are linked to a skeleton that enables the absorbent to exhibit desired light absorption characteristics as a whole, including the resonance structure and / or the conjugated bond, or together form such a skeleton.

[0053] The specific types of the absorption edge or the skeleton are not particularly limited. As is known, the resonance effect means the interaction between the π-bond electron pairs adjacent to the lone pair of electrons in a molecule, and the substituents or skeletons that cause such a resonance effect are known. In addition, a conjugated bond is a system in which two or more double bonds are formed with a single bond in between. It is known that the greater the increase in such a conjugated bond, the smaller the energy difference and the more the absorption band shifts to the long wavelength side.

[0054] For example, the absorption end may have a skeleton or structure such that the compound of the present application exhibits a maximum absorption within the wavelength range of 600 nm to 950 nm. That is, the compound can exhibit a maximum absorption wavelength within the range of 600 nm to 950 nm. The lower limit of the maximum absorption wavelength may be about 600 nm, 610 nm, 620 nm, 630 nm, 640 nm, 650 nm, 660 nm, 670 nm, 680 nm, 690 nm, 700 nm, 710 nm, 720 nm, 730 nm, 740 nm, 750 nm, 760 nm, 770 nm, 780 nm, 790 nm, 800 nm or 810 nm, and the upper limit thereof may be about 950 nm, 940 nm, 930 nm, 920 nm, 910 nm, 900 nm, 890 nm, 880 nm, 870 nm, 860 nm, 850 nm, 840 nm, 830 nm, 820 nm, 810 nm, 800 nm, 790 nm, 780 nm or 770 nm. The maximum absorption wavelength may be within the range above or exceeding any of the lower limits described above, or within the range below or less than any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being below or less than any of the upper limits described above.

[0055] As described above, the resonance structure and the conjugated bond determine the energy difference (ΔE) between the ground state and the excited state of the compound or the energy difference between the HOMO (Highest Occupied Molecular Orbital) and the LUMO (Lowest Unoccupied Molecular Orbital), and the maximum absorption wavelength is determined by such an energy difference. Therefore, the structure of the absorption end may be determined so that the compound has the maximum absorption wavelength within the range described above.

[0056] The alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, arylalkyl group, alkylene group, alkylidene group, alkenylene group, alkynylene group, alkylcarbonylamino group, arylalkylcarbonylamino group, haloalkylsulfonylamino group, arylalkylsulfonylamino group, alkylsulfonylamino group and amino group in Chemical Formula 1 may optionally be substituted by at least one substituent. In this case, examples of the substituent include, but are not limited to, halogen such as fluorine and chlorine, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, arylalkyl group, hydroxy group, cyano group, nitro group, carboxyl group, alkylcarbonylamino group, arylalkylcarbonylamino group, arylalkylsulfonylamino group, alkylsulfonylamino group or amino group.

[0057] In Chemical Formula 1, A1 to A3 are each independently an alkyl group, alkynyl group, alkenyl group or alkoxy group in suitable examples, or may be an alkyl group, but are not limited thereto.

[0058] -U in Chemical Formula 1 1- T 1- U 2- T 2- U 3- The divalent functional group represented by can satisfy any one of the following conditions 1 to 3 in suitable examples.

[0059] For example, the divalent functional group may be a functional group in which T1, T2, U1 and U3 are absent and U2 is an alkylene group, alkylidene group, alkenylene group or alkynylene group (Condition 1). In this case, the divalent functional group is represented by -U 2- as represented.

[0060] In other examples, in the divalent functional group, U1 and U3 are absent, either T1 or T2 is oxygen and the other is absent, and U2 may be a functional group that is an alkylene group, an alkylidene group, an alkenylene group, or an alkynylene group (Condition 2). In this case, the divalent functional group is -O-U 2- or -U 2- and becomes a functional group represented by O-.

[0061] In other examples, in the divalent functional group, U3 and T2 are absent, T1 is an oxygen atom, and U1 and U2 may each independently be a functional group that is an alkylene group, an alkylidene group, an alkenylene group, or an alkynylene group (Condition 3). In this case, the functional group is -U 1- O-U 2- and becomes a functional group represented by.

[0062] Among R3 to R8 in Chemical Formula 1, the substituents that do not form or are not linked to the absorption edge may, in suitable examples, each independently be hydrogen, a halogen, a hydroxy group, a cyano group, a nitro group, a carboxyl group, an alkyl group, an alkoxy group, an alkylsulfonylamino group, or an amino group, or may be hydrogen, an alkyl group, an alkylsulfonylamino group, or an amino group, but are not limited thereto.

[0063] The compound (absorbent) may have an appropriate level of molar weight. For example, the lower limit of the molar weight may be about 400 g / mol, 450 g / mol, 500 g / mol, 550 g / mol, 600 g / mol, 650 g / mol, 700 g / mol or 750 g / mol. The upper limit of the molar weight may be about 2,000 g / mol, 1,900 g / mol, 1,800 g / mol, 1,700 g / mol, 1,600 g / mol, 1,500 g / mol, 1,400 g / mol, 1,300 g / mol, 1,200 g / mol, 1,100 g / mol, 1,000 g / mol, 950 g / mol, 900 g / mol, 850 g / mol or 800 g / mol. The molar weight may be within the range above or exceeding any of the lower limits described above, or within the range below or less than any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being below or less than any of the upper limits described above.

[0064] The absorbent can have excellent heat resistance. For example, the absorbent may have a 5% thermal decomposition temperature (hereinafter, "Td 5%") within a predetermined range. For example, the lower limit of the Td 5% of the absorbent may be about 190 °C, 200 °C, 210 °C, 220 °C or 230 °C, and the upper limit thereof may be about 400 °C, 380 °C, 360 °C, 340 °C, 320 °C, 300 °C, 280 °C, 275 °C, 270 °C, 265 °C, 260 °C, 255 °C, 240 °C, 235 °C, 230 °C, 225 °C, 220 °C or 215 °C. The Td 5% may be within the range above or exceeding any of the lower limits described above, or within the range below or less than any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being below or less than any of the upper limits described above.

[0065] The Td 5% is a value obtained through TGA (Thermogravimetric analysis), and is the value (Td 5%) at a weight loss of 5% confirmed under the conditions of a temperature range of 25°C to 800°C, a heating rate of 10°C / min, and a nitrogen (N2) atmosphere of 60 cm 3 / min.

[0066] In one example, the absorbent may be a compound represented by Chemical Formula 2 below.

[0067]

Chemical Formula

[0068] In the structure of Chemical Formula 2, the conjugated structure formed between nitrogen atoms may be the backbone of the absorption edge formed by R1 and R2 in Chemical Formula 1.

[0069] In Chemical Formula 2, R9 and R 10 may each independently be hydrogen, an alkyl group, or a substituent of Chemical Formula 3 below. In one example, at least one of R9 and R 10 in Chemical Formula 2 may be a substituent of Chemical Formula 3 below, and both R9 and R 10 may be substituents of Chemical Formula 3 below.

[0070] In Chemical Formula 2, R 11 ~R 13 Among them, R 11 and R 12 may together form an absorption edge, or R 12 and R 13 may together form the absorption edge.

[0071] In Chemical Formula 2, R 14 ~R 16 Among them, R 14 and R 15 may together form an absorption edge, or R 15 and R 16 may together form the absorption edge.

[0072] In Chemical Formula 2, R 11 ~R 16 Among them, the specific types of substituents that do not form the absorption end are the same as those of the substituents that do not form the absorption end among R3 to R8 in Chemical Formula 1.

[0073] In Chemical Formula 2, n is an arbitrary number. The lower limit of n may be, for example, about 0 or 1, and the upper limit may be 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1. The n may be within the range above or exceeding any of the aforementioned lower limits, or within the range below or less than any of the aforementioned upper limits, or within the range above or exceeding any of the aforementioned lower limits while being below or less than any of the aforementioned upper limits.

[0074]

Chemical Formula

[0075] In Chemical Formula 3, L1 is linked to the nitrogen atom of Chemical Formula 2. The specific type of L1 in Chemical Formula 3 is the same as that of L1 in Chemical Formula 1.

[0076] Also, the specific types of A1 to A3 in Chemical Formula 3 are the same as those of A1 to A3 in Chemical Formula 1, respectively.

[0077] This specification further discloses an absorbent composition containing the absorbent. The term absorbent composition means a mixture containing an absorbent and other components or a mixture containing two or more absorbents.

[0078] Such an absorbent composition basically contains the absorbent of Chemical Formula 1 or 2 and may further contain other necessary components.

[0079] For example, the composition may further include a resin component that functions as a binder. There are no particular restrictions on the type of resin component applied in this case, and known resin components used to form an absorption film, for example, a near-infrared absorption film, may be applied. In the present application, the absorbent component can exhibit appropriate compatibility or solubility with the various known resin components.

[0080] Examples of the resin component include at least one of cyclic olefin (COP, Cyclo Olefin)-based resins, polyester resins, polyarylate resins, polysulfone resins, polyether sulfone resins, polyparaphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyetherimide resins, polyamideimide resins, acrylic resins, polycarbonate resins, polyethylene naphthalate resins, or silicone resins, and other various organic resins or organic-inorganic hybrid resins, but are not limited thereto.

[0081] Although not particularly limited, the absorbent may form an absorption film exhibiting excellent performance when mixed with a silicone resin among the resin components that function as the known binder. Therefore, in one example, the resin component may be a cyclic silicone resin.

[0082] When the resin component is applied, its proportion is not particularly limited. For example, the resin component may be present such that the weight proportion of the absorbent with respect to 100 parts by weight of the resin component is in the range of 0.001 part by weight to 10 parts by weight. The lower limit of the weight proportion of the absorbent with respect to 100 parts by weight of the resin component may, in other examples, be about 0.001 part by weight, 0.005 part by weight, 0.01 part by weight, 0.05 part by weight, 0.1 part by weight, 0.5 part by weight, 1 part by weight, 1.1 parts by weight, 1.2 parts by weight, 1.3 parts by weight or 1.4 parts by weight, and the upper limit thereof may be about 10 parts by weight, 9 parts by weight, 8 parts by weight, 7 parts by weight, 6 parts by weight, 5 parts by weight, 4 parts by weight, 3 parts by weight, 2 parts by weight or 1.5 parts by weight. The proportion may be within the range that is not less than any one of the aforementioned lower limits and not more than any one of the aforementioned upper limits.

[0083] For example, the absorbent composition may further contain a solvent in which the absorbent and / or the resin component is dispersed. There is no particular limitation on the type of solvent applied in this case, and known solvents used for forming an absorption film, for example, a near-infrared absorption film, may be applied. In the present application, the absorbent component can exhibit appropriate compatibility or solubility with respect to the various known solvents.

[0084] Examples of the solvent include, but are not limited to, methylene chloride, cyclohexanone, toluene, methyl ethyl ketone, methyl isobutyl ketone, propylene glycol methyl ether acetate, diethylene glycol monoethyl ether 3-methoxybutanol, ethylene glycol monobutyl ether acetate, 4-hydroxy-4-methyl-2-pentanone, γ-butyrolactone, cyclohexanone, pyridone, chloroform, 1,4-dioxane, cyclohexanone, ortho-dichlorobenzene, chlorobenzene aliphatic alcohols having 2 or more carbon atoms (for example, isobutyl alcohol, isopropyl alcohol, ethanol, isopropanol, butanol, etc.), butyl acetate, tetrahydrofuran or xylene.

[0085] When the solvent is applied, there is no particular limitation on the ratio, and the ratio may be adjusted within a range where appropriate dispersion of the absorbent and / or resin component is possible.

[0086] The absorbent composition may further contain other necessary components in addition to the above-described components, for example, an absorbent of a type different from the absorbent of Chemical Formula 1 or Chemical Formula 2.

[0087] This specification further discloses the use of the absorbent composition or the absorbent.

[0088] For example, it may relate to an absorbent film to which the absorbent composition or absorbent is applied.

[0089] Such an absorbent film may contain at least a resin component and the absorbent.

[0090] In this case, the specific type of the resin component and the ratio between the resin component and the absorbent are as described in the item of the absorbent composition.

[0091] The absorbent film may be a film capable of absorbing light within a predetermined wavelength range. In one example, the absorbent film may be an infrared absorption film or a near-infrared absorption film. Such an absorbent film can exhibit absorption characteristics, for example, in at least a part of the wavelength range within the range of about 600 nm to 950 nm.

[0092] For example, the absorption film can exhibit an absorption peak wavelength within the range of 600 nm to 950 nm. The lower limit of the absorption peak wavelength may, in other examples, be about 600 nm, 610 nm, 620 nm, 630 nm, 640 nm, 650 nm, 660 nm, 670 nm, 680 nm, 690 nm, 700 nm, 710 nm, 720 nm, 730 nm, 740 nm, 750 nm, 760 nm, 770 nm, 780 nm, 790 nm, 800 nm or 810 nm. Also, the upper limit of the absorption peak wavelength may be about 950 nm, 940 nm, 930 nm, 920 nm, 910 nm, 900 nm, 890 nm, 880 nm, 870 nm, 860 nm, 850 nm, 840 nm, 830 nm, 820 nm, 810 nm, 800 nm, 790 nm, 780 nm, 770 nm, 760 nm, 750 nm, 740 nm, 730 nm, 720 nm, 710 nm, 700 nm, 690 nm, 680 nm, 670 nm, 660 nm, 650 nm, 640 nm, 630 nm, 620 nm or 610 nm. The absorption peak wavelength may be within the range that is greater than or equal to any one of the aforementioned lower limits and less than or equal to any one of the aforementioned upper limits.

[0093] Due to such characteristics, the absorption film has excellent optical properties such as being applicable to various devices such as optical filters and infrared sensors and being able to prevent the shift phenomenon due to the incident angle, and may also have physical properties such as excellent heat resistance.

[0094] For example, in the absorption film, the absolute value of ΔA in the following formula 1 may be within a predetermined range.

[0095] [Formula 1] ΔA = 100×(A f - A i ) / A i

[0096] In formula 1, A f is the transmittance at the absorption peak wavelength of the absorption film held at 85 °C and 85% relative humidity for 120 hours, and A iis the transmittance at the absorption maximum wavelength of the absorption film before being held at 85 °C and 85% relative humidity for 120 hours, and the absorption maximum wavelength exists within the wavelength range of 600 nm to 950 nm.

[0097] In Equation 1, the upper limit of the absolute value of ΔA may be about 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5% or 4.5%, and the lower limit thereof may be about 0%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5% or 7%. The absolute value of ΔA is within the range below or less than any of the upper limits described above, or above or exceeding any of the lower limits described above, but within the range below or less than any of the upper limits described above.

[0098] In the formula 1, A f and A i The upper limit of each of them may be about 40%, 35%, 30%, 25%, 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8% or 7%, and the lower limit may be about 0%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5% or 8%. Each of the A f and A i Each of them may be within the range below or less than any of the upper limits described above, or above or exceeding any of the lower limits described above, but within the range below or less than any of the upper limits described above.

[0099] The absolute value of Δλ in the following formula 2 of the absorption film may be 10% or less.

[0100] [Formula 2] Δλ = 100×(λ f -λ i ) / λ i

[0101] In Formula 2, λ f is the absorption maximum wavelength of the absorption film maintained at 85°C and 85% relative humidity for 120 hours, and λ i is the absorption maximum wavelength of the absorption film before being maintained at 85°C and 85% relative humidity for 120 hours, and the absorption maximum wavelength exists within the wavelength range of 600 nm to 950 nm.

[0102] In Formula 2, the upper limit of the absolute value of Δλ is about 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1% or 0.5% in other examples, and the lower limit may be about 0%, 0.5% or 1%. The absolute value of the Δλ may be within the range of not less than any of the lower limits described above and not more than any of the upper limits described above.

[0103] In the Formula 2, λ f and λ i may each be within the range of 600 nm to 950 nm. The lower limit of each of the λ f and λ i may be 600 nm, 610 nm, 620 nm, 630 nm, 640 nm, 650 nm, 660 nm, 670 nm, 680 nm, 690 nm, 700 nm, 710 nm, 720 nm, 730 nm, 740 nm, 750 nm, 760 nm, 770 nm, 780 nm or 790 nm in other examples. Also, the upper limit of each of the λ f and λ i may be about 950 nm, 940 nm, 930 nm, 920 nm, 910 nm, 900 nm, 890 nm, 880 nm, 870 nm, 860 nm, 850 nm, 840 nm, 830 nm, 820 nm, 810 nm, 800 nm, 790 nm, 780 nm, 770 nm, 760 nm, 750 nm, 740 nm, 730 nm, 720 nm, 710 nm, 700 nm, 690 nm, 680 nm, 670 nm, 660 nm, 650 nm, 640 nm, 630 nm, 620 nm or 610 nm. The λ f and λ iEach of them may be within a range that is equal to or greater than any of the aforementioned lower limits and equal to or less than any of the aforementioned upper limits.

[0104] Through the absorption characteristics, the absorption film is applied to devices such as various optical filters and infrared sensors, and desired characteristics can be efficiently achieved.

[0105] The absorption film may be formed by a known method as long as the absorbent composition or absorbent is applied. For example, the absorbent composition may be coated in an appropriate manner, and a curing or drying process may be performed as necessary to form the absorption film.

[0106] There is no particular limitation on the thickness of the absorption film, and the thickness may be adjusted in consideration of desired characteristics. In one example, the absorption film may have a thickness in the range of about 0.5 μm to 20 μm.

[0107] This specification further discloses an optical filter. The optical filter may include a substrate layer and the absorption film formed on one or both sides of the substrate layer.

[0108] FIG. 1 shows a case where the absorption film 200 is formed on one side of the substrate layer 100 as an example of the optical filter.

[0109] Such an optical filter can exhibit excellent performance by including the aforementioned absorption film. For example, the optical filter can embody a visible light transmission band with high transmittance while efficiently and accurately blocking unnecessary infrared light.

[0110] There is no particular limitation on the type of transparent substrate applied to the optical filter, and a known transparent substrate for an optical filter may be used.

[0111] In one example, the base material layer may be a so-called infrared absorption substrate. An infrared absorption substrate is a substrate that exhibits absorption characteristics in at least a part of the infrared region. So-called Blue Glass, which exhibits such characteristics including copper, is a typical example of the infrared absorption substrate. Such an infrared absorption substrate is useful for forming an optical filter that blocks light in the infrared region, but is disadvantageous in terms of ensuring a high transmittance in the visible light region due to the absorption characteristics, and is also disadvantageous in terms of durability. In the present application, by selecting an infrared absorption substrate and combining it with a specific absorption film, it is possible to provide an optical filter that efficiently blocks desired light while exhibiting high transmittance characteristics in the visible light region and having excellent durability.

[0112] As the infrared absorption substrate, a substrate having an average transmittance of 75% or more in the range of 425 nm to 560 nm may be used. In other examples, the average transmittance may be in the range of 77% or more, 79% or more, 81% or more, 83% or more, 85% or more, 87% or more, or 89% or more and / or in the range of 98% or less, 96% or less, 94% or less, 92% or less, or 90% or less.

[0113] As the infrared absorption substrate, a substrate having a maximum transmittance of 80% or more in the range of 425 nm to 560 nm may be used. In other examples, the maximum transmittance may be in the range of 82% or more, 84% or more, 86% or more, 88% or more, or 90% or more and / or in the range of 100% or less, 98% or less, 96% or less, 94% or less, 92% or less, or 90% or less.

[0114] As the infrared absorption substrate, a substrate having an average transmittance of 75% or more in the range of 350 nm to 390 nm may be used. In other examples, the average transmittance may be in the range of 77% or more, 79% or more, 81% or more, or 83% or more and / or in the range of 98% or less, 96% or less, 94% or less, 92% or less, 90% or less, 88% or less, 86% or less, or 84% or less.

[0115] As the infrared absorption substrate, a substrate showing a maximum transmittance of 80% or more within the range of 350 nm to 390 nm may be used. In other examples, the maximum transmittance may be within the range of 82% or more, 84% or more, 86% or more, or 87% or more and / or within the range of 100% or less, 98% or less, 96% or less, 94% or less, 92% or less, 90% or less, or 88% or less.

[0116] As the infrared absorption substrate, a substrate having a transmittance at a wavelength of 700 nm within the range of 10% to 45% may be used. In other examples, the transmittance may be about 43% or less, 41% or less, 39% or less, 37% or less, 35% or less, 33% or less, 31% or less, or 29% or less, or may be about 12% or more, 14% or more, 16% or more, 18% or more, 20% or more, 22% or more, 24% or more, 26% or more, or 28% or more.

[0117] As the infrared absorption substrate, a substrate showing an average transmittance within the range of 5% to 30% within the range of 700 nm to 800 nm may be used. In other examples, the average transmittance may be within the range of 7% or more, 9% or more, 11% or more, 13% or more, 15% or more, 15.5% or more, 16% or more, or 16.5% or more and / or within the range of 28% or less, 26% or less, 24% or less, 22% or less, 20% or less, 18% or less, or 17% or less.

[0118] As the infrared absorption substrate, a substrate showing a maximum transmittance within the range of 10% to 45% within the range of 700 nm to 800 nm may be used. In other examples, the maximum transmittance may be within the range of 12% or more, 14% or more, 16% or more, 18% or more, 20% or more, 22% or more, 24% or more, 26% or more, or 28% or more and / or within the range of 43% or less, 41% or less, 39% or less, 37% or less, 35% or less, 33% or less, 31% or less, or 29% or less.

[0119] As the infrared absorption substrate, a substrate showing an average transmittance in the range of 3% to 20% within the range of 800 nm to 1000 nm may be used. In other examples, the average transmittance may be further adjusted within the range of 5% or more, 7% or more, 9% or more, or 11% or more and / or within the range of 18% or less, 16% or less, 14% or less, or 12% or less.

[0120] As the infrared absorption substrate, a substrate showing a maximum transmittance in the range of 5% to 30% within the range of 800 nm to 1000 nm may be used. In other examples, the maximum transmittance may be within the range of 7% or more, 9% or more, 11% or more, 13% or more, or 15% or more and / or within the range of 28% or less, 26% or less, 24% or less, 22% or less, 20% or less, 18% or less, or 16% or less.

[0121] As the infrared absorption substrate, a substrate showing an average transmittance in the range of 10% to 50% within the range of 1000 nm to 1200 nm may be applied. In other examples, the average transmittance may be further adjusted within the range of 12% or more, 14% or more, 16% or more, 18% or more, 20% or more, 22% or more, 24% or more, or 25% or more and / or within the range of 48% or less, 46% or less, 44% or less, 42% or less, 40% or less, 38% or less, 36% or less, 34% or less, 32% or less, 30% or less, 28% or less, or 26% or less.

[0122] As the infrared absorption substrate, it may have a transmission band showing a maximum transmittance in the range of 10% to 70% within the range of 1000 nm to 1200 nm. In other examples, the maximum transmittance may be within the range of 12% or more, 14% or more, 16% or more, 18% or more, 20% or more, 22% or more, 24% or more, 26% or more, 28% or more, 30% or more, 32% or more, 34% or more, or 36% or more and / or within the range of 68% or less, 66% or less, 64% or less, 62% or less, 60% or less, 58% or less, 56% or less, 54% or less, 52% or less, 50% or less, 48% or less, 46% or less, 44% or less, 42% or less, 40% or less, 38% or less, or 37% or less.

[0123] The infrared absorption substrate may form a desired optical filter in combination with the absorption film.

[0124] As such a substrate, a substrate known as so-called infrared absorption glass may be used. Such glass is an absorption-type glass produced by adding CuO or the like to phosphate fluoride glass, phosphate glass, or the like. Therefore, in one example, in the present application, as the infrared absorption substrate, a CuO-containing phosphate fluoride glass substrate or a CuO-containing phosphate glass substrate may be used. The phosphate glass includes K phosphate glass in which a part of the glass skeleton is made of SiO2. Such absorption-type glass is known, and for example, glass disclosed in Korean Registered Patent No. 10-2056613 or other commercially available absorption-type glass (for example, commercially available products of Hoya, Schott, PTOT, etc.) may be used.

[0125] Such an infrared absorption substrate contains copper. In the present application, a substrate in which the copper content is in the range of 1 wt% to 7 wt% may be used. In other examples, the copper content may be about 1.5 wt% or more, 2 wt% or more, 2.5 wt% or more, 2.6 wt% or more, 2.7 wt% or more, or 2.8 wt% or more, and may be about 6.5 wt% or less, 6 wt% or less, 5.5 wt% or less, 5 wt% or less, 4.5 wt% or less, 4 wt% or less, 3.5 wt% or less, 3 wt% or less, or 2.9 wt% or less. A substrate having such a copper content is likely to exhibit the above-described optical characteristics and can form an optical filter having desired characteristics in combination with the absorption film.

[0126] The copper content can be confirmed using a wavelength dispersive X-ray fluorescence spectrometry (WD XRF) device. When the specimen (substrate layer) is irradiated with X-rays using the device, characteristic secondary X-rays are generated from the individual elements of the specimen, and the device detects the secondary X-rays according to the wavelength for each element. The intensity of the secondary X-rays is proportional to the content of the element. Therefore, quantitative analysis may be performed through the intensity of the secondary X-rays measured according to the wavelength for each element.

[0127] The thickness of the infrared absorption substrate may be adjusted, for example, within the range of about 0.03 mm to 5 mm, but is not limited thereto.

[0128] The optical filter may further include other known components necessary for the base material layer and the absorption film.

[0129] For example, the optical filter may further include a dielectric film. The dielectric film may further include, for example, a so-called dielectric film on one or both sides of the base material layer.

[0130] FIG. 2 and FIG. 3 are illustrations of an optical filter with a dielectric film added, showing the case where the dielectric film 300 is formed on one or both sides of a laminated structure including a base material layer 100 and an absorption film 200.

[0131] Such a dielectric film is a film formed by repeatedly laminating a low refractive index dielectric material and a high refractive index dielectric material, and is used to form a so-called IR reflection layer and an AR (Anti-reflection) layer. In this application, a dielectric film for forming such a known IR reflection layer or AR layer may also be applied.

[0132] Therefore, the dielectric film may be a multilayer structure including at least two sub-layers having different refractive indices from each other, and may include a multilayer structure in which the two sub-layers are repeatedly laminated.

[0133] The material for forming the dielectric film, that is, the type of material for forming each sub-layer is not particularly limited, and known materials may be applied. Usually, for the production of a low refractive index sub-layer, fluorides such as SiO2 or Na5Al3Fl4, Na3AlF6 or MgF2 are applied, and for the production of a high refractive index sub-layer, amorphous silicon, TiO2, Ta2O5, Nb2O5, ZnS or ZnSe may be applied, but the materials applied in this application are not limited thereto.

[0134] The method of forming the dielectric film as described above is not particularly limited. For example, a known vapor deposition method may be applied for formation. In the art, a method of controlling the reflection or transmission characteristics of the dielectric film by considering the vapor deposition thickness and the number of layers of the sub-layer is known. In the present application, the dielectric film may be formed by such a known method.

[0135] In one example, the shortest wavelength at which the dielectric film included in the optical filter exhibits a reflectance of 50% within the wavelength range of 600 nm to 900 nm is 710 nm or more, or such a wavelength may not exist. Further, when such a wavelength does not exist, the maximum reflectance of the dielectric film within the wavelength range of 600 nm to 900 nm is less than 50%. When the wavelength exists, the shortest wavelength at which the 50% reflectance is exhibited is, in other examples, 715 nm or more, 720 nm or more, 725 nm or more, 730 nm or more, 735 nm or more, 740 nm or more, 745 nm or more, 750 nm or more, or about 754 nm or more, or may be 900 nm or less, 850 nm or less, 800 nm or less, 790 nm or less, 780 nm or less, 770 nm or less, or 760 nm or less. The shortest wavelength at which the 50% reflectance is exhibited may be within the range of any of the lower limits and the upper limit described above. At this time, the upper limit may be 900 nm.

[0136] By controlling the reflection characteristics of the dielectric film as described above, a so-called petal flare phenomenon can be prevented. The petal flare phenomenon means a phenomenon in which a red line or the like that is not observed with the naked eye when photographing a light emitter or the like appears in the photograph. In many cases, the red line has a petal-like shape with respect to the light emitter and is called petal flare. As the sensitivity of the sensor included in the imaging device increases and the transmittance of an optical filter or the like is increased to obtain a clearer photograph, the occurrence frequency of the petal flare has increased.

[0137] One of the causes of the petal flare phenomenon is considered to be the repeated reflection of near-infrared light within the imaging device equipped with the optical filter. Usually, among the dielectric films formed on the optical filter, especially the so-called IR film is formed to block light in the near-infrared region by reflection. Therefore, the shortest wavelength at which the dielectric film exhibits a reflectance of 50% is formed near visible light, which is usually less than 710 nm. However, such a dielectric film accelerates the reflection of near-infrared light within the imaging device, thereby causing the petal flare phenomenon.

[0138] However, in this application, even when the shortest wavelength at which the dielectric film exhibits a reflectance of 50% is adjusted to 710 nm or more through the application of the absorption film, infrared light can be effectively blocked, and furthermore, the petal flare phenomenon can also be prevented. The design method itself for adjusting the reflection characteristics of the dielectric film is known.

[0139] The optical filter may further include an absorption film (hereinafter, ultraviolet absorption film) that exhibits absorption characteristics with respect to ultraviolet rays as an absorption film that is distinguished from the absorption film. However, such an absorption film is not an essential component. For example, an ultraviolet absorber described later may be introduced into one absorption film together with the absorber of Chemical Formula 1.

[0140] In one example, the ultraviolet absorption film may be designed to exhibit an absorption maximum in the wavelength range of about 300 nm to 390 nm.

[0141] The ultraviolet absorption film may contain only an ultraviolet absorber, or may contain two or more ultraviolet absorbers as necessary.

[0142] For example, as the ultraviolet absorber, a known absorber showing an absorption maximum in the wavelength range of about 300 nm to 390 nm may be applied. Examples thereof include ABS 407 from Exiton; UV381A, UV381B, UV382A, UV386A, VIS404A from QCR Solutions Corp; ADA1225, ADA3209, ADA3216, ADA3217, ADA3218, ADA3230, ADA5205, ADA3217, ADA2055, ADA6798, ADA3102, ADA3204, ADA3210, ADA2041, ADA3201, ADA3202, ADA3215, ADA3219, ADA3225, ADA3232, ADA4160, ADA5278, ADA5762, ADA6826, ADA7226, ADA4634, ADA3213, ADA3227, ADA5922, ADA5950, ADA6752, ADA7130, ADA8212, ADA2984, ADA2999, ADA3220, ADA3228, ADA3235, ADA3240, ADA3211, ADA3221, ADA5220, ADA7158 from H.W.Sands; DLS 381B, DLS 381C, DLS 382A, DLS 386A, DLS 404A, DLS 405A, DLS 405C, DLS 403A from CRYSTALYN, etc., but it is not limited thereto.

[0143] The materials and configuration methods for constituting such an ultraviolet absorption film are not particularly limited, and known materials and configuration methods may be applied.

[0144] Generally, the ultraviolet absorption film is formed using a material in which an ultraviolet absorber capable of showing a desired absorption maximum is blended with a transparent resin. At this time, as the transparent resin, the resin component applied to the absorber composition may be applied.

[0145] In addition to the aforementioned layers, various necessary layers may be added to the optical filter as long as the desired effects are not impaired.

[0146] This specification further discloses an imaging device including the optical filter. At this time, the configuration method of the imaging device and the application method of the optical filter are not particularly limited, and known configurations and application methods may be applied.

[0147] In addition, the use of the optical filter is not limited to the imaging device, and it may be applied to various other applications that require near-infrared cut, (for example, display devices such as PDPs, etc.).

[0148] This specification further discloses an infrared sensor including the absorption film. The configuration of the infrared sensor is not particularly limited as long as the absorption film is included. For example, the absorption film of the present application may be introduced into a known motion sensor, proximity sensor, or gesture sensor for configuration.

[0149] The use of the absorbent composition or absorption film is not limited to the optical filter, infrared sensor, and / or imaging device, and it may be applied to various other applications that require infrared cut (for example, display devices such as PDPs, etc.).

Advantages of the Invention

[0150] This specification discloses an absorbent and its use. The absorbent exhibits excellent compatibility or solubility with various solvents and resin components as an organic absorbent, has excellent heat resistance, and can stably maintain its optical properties even when held under high-temperature conditions or high-temperature and high-humidity conditions. By applying the absorbent, an absorption film capable of ensuring desired optical properties can be provided. This specification further discloses the use of the absorbent or absorption film.

Brief Description of the Drawings

[0151]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Figure 9

Mode for Carrying Out the Invention

[0152] Hereinafter, the absorbent and the like will be specifically described through examples, but the scope of the absorbent and the like is not limited by the following examples.

[0153] 1. Method for Measuring Absorption Maximum The absorption maximum was evaluated by a conventional method. Specifically, after dissolving the sample in a chloroform solvent at a concentration of about 10 -5 M, it was evaluated using a measuring device (Agilent, Varian cary 4000).

[0154] 2. Evaluation of Transmittance Spectrum The transmittance spectrum was measured using a spectrophotometer (manufacturer: PerkinElmer, product name: Lambda 750 spectrophotometer) for a specimen obtained by cutting the measurement target (for example, an absorption film) to be 10 mm in width and 10 mm in length. The transmittance spectrum was measured for each wavelength according to the manual of the device. The specimen was placed on a straight line between the measurement beam and the detector of the spectrophotometer, and the transmittance spectrum was confirmed with the incident angle of the measurement beam being 0 degrees. The incident angle of 0 degrees is a direction substantially parallel to the normal direction of the surface of the specimen. The average transmittance within a predetermined wavelength range in the transmittance spectrum is the result of obtaining the arithmetic mean of the transmittances measured at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength in the wavelength range. The maximum transmittance is the maximum transmittance among the transmittances measured while increasing the wavelength by 1 nm each time, and the minimum transmittance is the minimum transmittance among the transmittances measured while increasing the wavelength by 1 nm each time. For example, the average transmittance within the wavelength range of 350 nm to 360 nm is the arithmetic mean of the transmittances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm. The maximum transmittance within the wavelength range of 350 nm to 360 nm is the highest transmittance among the transmittances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm, and the minimum transmittance within the wavelength range of 350 nm to 360 nm is the lowest transmittance among the transmittances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

[0155] 3. Solubility Measurement Method The solubility of the absorbent was evaluated. The solubility was evaluated by the solubility of the absorbent in a solvent (MC, Methylene Chloride) at room temperature (about 25°C) and judged according to the following criteria. <Solubility Judgment Criteria> A: When the solubility is 1 mass% or more B: When the solubility is 0.5 mass% or more and less than 1 mass% C: When the solubility is 0.2% by mass or more and less than 0.5% by mass D: When the solubility is less than 0.2% by mass

[0156] 4. Thermal decomposition temperature (Td 5%) analysis The TGA (Thermogravimetric analysis) analysis was carried out using a TGA N-1000 device manufactured by Scinco. Analysis was performed using approximately 3 mg of the sample (absorbent), and the analysis was carried out under the conditions of a temperature range of 25°C to 800°C, a heating rate of 10°C / min, and a nitrogen (N2) atmosphere of 60 cm 3 / min. The Td decomposition temperature used was the value (Td 5%) at a weight loss of 5%.

[0157] 5. Mass analysis (LC-Mass) The Mass analysis of the synthesized compound was carried out using a liquid chromatograph / mass spectrometer (manufactured by Thermo Fisher Scientific).

[0158] Example 1. The ionic compound (A1) containing the cation of the following Chemical Formula A and the anion of the following Chemical Formula B was synthesized according to the following Reaction Formula 1.

[0159]

Chemical Formula

[0160]

Chemical Formula

[0161]

Chemical Formula

[0162] 1.1 g (1.62 mmol) of Compound A in Reaction Formula 1 and 0.56 g (1.94 mmol) of lithium bis(trifluoromethanesulfonyl)imide were dissolved in 30 mL of dichloromethane. After adding 30 mL of water, the mixture was reacted at room temperature (about 25°C) for about 2 hours. After the reaction, the dichloromethane layer and the aqueous layer were separated with an extractor and then concentrated. After adding 100 mL of ethanol, the mixture was filtered under reduced pressure to obtain the target compound (ionic compound A1) (0.4 g, 29.7%) (LC-MS(+) m / z 553.8, LC-MS(-) m / z 279.9).

[0163] Example 2. The ionic compound (A2) containing the cation of the following Chemical Formula C and the anion of the following Chemical Formula B was synthesized according to the following Reaction Formula 2.

[0164]

Chemical Formula

[0165]

Chemical Formula

[0166]

Chemical Formula

[0167] 1.0 g (1.28 mmol) of Compound B in Reaction Formula 2 and 0.56 g (1.94 mmol) of lithium bis(trifluoromethanesulfonyl)imide were dissolved in 30 mL of dichloromethane. After adding 30 mL of water, the mixture was reacted at room temperature (about 25°C) for about 2 hours. After the reaction, the dichloromethane layer and the aqueous layer were separated with an extractor and then concentrated. After adding 100 mL of ethanol, the mixture was filtered under reduced pressure to obtain the target compound (ionic compound A2) (0.5 g, 41.8%) (LC-MS(+) m / z 653.8, LC-MS(-) m / z 280.1).

[0168] Example 3. The ionic compound (A3) containing the cation of Chemical Formula D below and the anion of Chemical Formula B below was synthesized according to the following Reaction Formula 3.

[0169]

Chemical Formula

[0170]

Chemical Formula

[0171]

Chemical Formula

[0172] 1.1 g (1.48 mmol) of Compound C in Reaction Formula 3 and 0.56 g (1.94 mmol) of lithium bis(trifluoromethanesulfonyl)imide were dissolved in 30 mL of dichloromethane, and after further adding 30 mL of water, the mixture was reacted at room temperature (about 25 °C) for about 2 hours. After the reaction, the dichloromethane layer and the aqueous layer were separated with an extractor and then concentrated. After adding 100 mL of ethanol, the mixture was filtered under reduced pressure to obtain the target compound (ionic compound A3) (0.3 g, 22.6%) (LC-MS(+) m / z 614.1, LC-MS(-) m / z 280.1).

[0173] Comparative Example 1. The ionic compound (A4) containing the cation of Chemical Formula E below and the anion of Chemical Formula B below was synthesized according to the following Reaction Formula 4.

[0174]

Chemical Formula

[0175]

Chemical Formula

[0176] [Chemical formula] Reaction formula 4

[0177] 2.1 g (3.38 mmol) of compound D in Reaction formula 3 and 0.56 g (1.94 mmol) of lithium bis(trifluoromethanesulfonyl)imide were dissolved in 30 mL of dichloromethane, and after further adding 30 mL of water, the mixture was reacted at room temperature (about 25 °C) for about 2 hours. After the reaction, the dichloromethane layer and the aqueous layer were separated with an extractor and then concentrated. After adding 100 mL of ethanol, filtration under reduced pressure was performed to obtain the target compound (ionic compound A4) (1.1 g, 42.0%) (LC-MS(+) m / z 493.4, LC-MS(-) m / z 280.0).

[0178] Comparative Example 2. The ionic compound (A2) containing the cation of Chemical formula F below and the anion of Chemical formula B below was synthesized according to the following Reaction formula 5.

[0179] [Chemical formula] Chemical formula F [Chemical formula] Chemical formula B

[0180] [Chemical formula] Reaction formula 5

[0181] 2.5 g (3.47 mmol) of compound E in Reaction Formula 5 and 0.56 g (1.94 mmol) of lithium bis(trifluoromethanesulfonyl)imide were dissolved in 30 mL of dichloromethane, and after further adding 30 mL of water, the mixture was reacted at room temperature (about 25°C) for about 2 hours. After the reaction, the dichloromethane layer and the aqueous layer were separated with an extractor and then concentrated. After adding 100 mL of ethanol, filtration under reduced pressure was performed to obtain the target compound (ionic compound A5) (1.5 g, 49.5%) (LC-MS(+) m / z 593.5, LC-MS(-) m / z 280.0).

[0182] Comparative Example 3. The ionic compound (A6) containing the cation of the following Chemical Formula F and the anion of the following Chemical Formula B was synthesized according to the following Reaction Formula 6.

[0183]

Chemical Formula

[0184]

Chemical Formula

[0185]

Chemical Formula

[0186] 1.8 g (2.64 mmol) of compound F in Reaction Formula 6 and 0.56 g (1.94 mmol) of lithium bis(trifluoromethanesulfonyl)imide were dissolved in 30 mL of dichloromethane, and after further adding 30 mL of water, the mixture was reacted at room temperature (about 25°C) for about 2 hours. After the reaction, the dichloromethane layer and the aqueous layer were separated with an extractor and then concentrated. After adding 100 mL of ethanol, filtration under reduced pressure was performed to obtain the target compound (ionic compound A6) (0.9 g, 40.8%) (LC-MS(+) m / z 553.7, LC-MS(-) m / z 280.1).

[0187] Table 1 below shows the summarized results of the characteristics of the absorbents of Examples 1 to 3 and Comparative Examples 1 to 6. In Table 1 below, Td 5% means the 5% thermal decomposition temperature.

[0188]

Table 1

[0189] Test Example 1. A coating solution was prepared by mixing a silicone resin (Dow Chemical, RSN-0217) as a resin component, an absorbent, and a solvent (Cyclohexanone). The mixing ratio of the resin component, absorbent, and solvent was 69.3:0.99:29.7 by weight ratio (resin:absorbent: solvent).

[0190] The coating solution was coated on a transparent substrate (a glass substrate manufactured by SCHOTT) and held at 140 °C for about 2 hours to form an absorption film having a thickness of about 6 μm.

[0191] In the above, as the absorbent, the absorbents of Examples 1, 2, 3, Comparative Examples 1, 2, or 3 were applied.

[0192] Tables 2 and 3 below summarize the transmittance before and after the reliability evaluation of the absorption film in the ultraviolet and near-infrared regions. The reliability evaluation is an evaluation in which the absorption film is held at 85 °C and 85% relative humidity for 120 hours. In Table 2 below, B represents the result before the reliability evaluation, and A represents the result after the reliability evaluation. Also, in Table 2 below, λmax means the transmittance at the absorption maximum.

[0193] In Tables 2 and 3 below, Δ is the change rate (%) of each characteristic before and after the reliability evaluation, and is the result calculated by 100×(A - B) / B, where A is the numerical value represented by A in Table 2 below, and B is the numerical value represented by B in Table 2 below. In Table 2 below, T max is the highest transmittance in the corresponding wavelength region, T ave is the average transmittance in the corresponding wavelength region, Tmin means the minimum transmittance within the corresponding wavelength range.

[0194] [Table 2]

[0195] [Table 3]

[0196] Test Example 2. Figures 4 to 6 are the absorption spectra of the absorption films manufactured using the absorbents of Examples 1 to 3, respectively, as the absorption films manufactured in Test Example 1, and Figures 7 to 9 are the absorption spectra of the absorption films manufactured using the absorbents of Comparative Examples 1 to 3, respectively, as the absorption films manufactured in Test Example 1. In the figures, the graphs displayed as before reliability are the results immediately after manufacturing the absorption film, and the graphs displayed as after reliability are the results after performing a high-temperature and high-humidity evaluation on the absorption film. The high-temperature and high-humidity evaluation is an evaluation in which the absorption film is held at a temperature of 85°C and a relative humidity of 85% for 120 hours.

[0197] It can be confirmed from the drawings that the absorption films using the absorbents of Examples 1 to 3 hardly change in absorption characteristics before and after reliability and are kept the same, whereas when the absorbents of Comparative Examples 1 to 3 are applied, the absorption characteristics are almost lost after high-temperature and high-humidity.

[0198] Summarizing the main content in the said drawings, it is as shown in Tables 4 and 5 below. In Tables 4 and 5 below, A f is the transmittance at the absorption maximum wavelength of the absorption film held at 85°C and a relative humidity of 85% for 120 hours, λ f is the absorption maximum wavelength at this time, A i is the transmittance at the absorption maximum wavelength of the absorption film before being held at 85°C and a relative humidity of 85% for 120 hours, λ i is the absorption maximum wavelength at this time.

[0199] In Tables 4 and 5 below, ΔA is the value calculated by 100×(A f - A i ) / A i , and Δλ is the value calculated by 100×(λ f - λ i ) / λ i .

[0200] [Table 4]

[0201] [Table 5]

[0202] Comparing the drawings with the results of Tables 4 and 5, it can be seen that the absorbents of the examples and the comparative examples have similar spectral characteristics of the absorbents themselves, but show a large difference in the absorption characteristics and the absorption characteristics after high-temperature and high-humidity evaluation when applied to the absorption film. From such a point, it can be confirmed that the absorbent of the present application is excellent in compatibility with the resin component forming the absorption film due to its unique structure and excellent in heat resistance, and thus can effectively form an absorption film with excellent performance. [Description of Reference Numerals]

[0203] 100 Substrate layer 200 Absorption film 300 Dielectric film

Claims

1. An absorbent comprising a cation represented by the following formula 1: 【Chemistry 1】 Chemical 1 In Chemical Formula 1, A 1 ~A 3 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryl group, or an arylalkyl group; L 1 , -U 1- T 1- U 2- T 2- U 3- And T 1 and T 2 are each independently an oxygen atom or absent; U 1 ~U 3 are each independently an alkylene group, an alkylidene group, an alkenylene group, an alkynylene group, or are absent; R 1 and R 2 forms an absorption edge, and R 3 ~R 8 Of these, R 3 ~R 6 Or R 5 ~R 8 forms an absorption edge, and R 3 ~R 8 The substituents not forming the absorption edge among the above are each independently hydrogen, halogen, a hydroxy group, a cyano group, a nitro group, a carboxyl group, an alkyl group, an alkoxy group, an aryl group, an arylalkyl group, an alkylcarbonylamino group, an arylalkylcarbonylamino group, a haloalkylsulfonylamino group, an alkylsulfonylamino group, an arylalkylsulfonylamino group, or an amino group. In Chemical formula 1, the dotted line represents a single bond or a double bond. When the dotted line represents a double bond, R 2 is not present and the dotted line is a double bond, a cationic moiety is formed at the nitrogen atom connected to the dotted line.

2. In Chemical Formula 1, A 1 ~A 3 and each independently is an alkyl group, an alkynyl group, an alkenyl group, or an alkoxy group.

3. The absorbent according to claim 2, which satisfies any one of the following conditions 1 to 3. Condition 1 is T in Chemical formula 1. 1 , T 2 , U 1 and U 3 does not exist, and U 2 is an alkylene group, an alkylidene group, an alkenylene group, or an alkynylene group, Condition 2 is that in Chemical formula 1, U 1 and U 3 does not exist, and T 1 and T 2 is oxygen and the other is absent, and U 2 is an alkylene group, an alkylidene group, an alkenylene group, or an alkynylene group, Condition 3 is U 3 and T 2 does not exist, and T 1 is an oxygen atom, and U 1 and U 2 each independently represents an alkylene group, an alkylidene group, an alkenylene group, or an alkynylene group.

4. R 3 ~R 8 The absorbent according to claim 1, wherein the substituents not forming an absorption edge among the above are each independently hydrogen, halogen, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, an alkyl group, an alkoxy group, an alkylsulfonylamino group, or an amino group.

5. 2. The absorbent of claim 1, wherein the cation is represented by the formula: 【Chemistry 2】 2 In Chemical Formula 2, R 9 and R 10 are each independently a hydrogen atom, an alkyl group, or a substituent of the formula 3 below, 9 and R 10 At least one of the groups represented by the following formula 3 is a substituent group, 11 ~R 13 Of these, R 11 and R 12 Or R 12 and R 13 together form an absorption edge, R 14 ~R 16 Of these, R 14 and R 15 Or R 15 and R 16 together form an absorption edge, R 11 ~R 16 The substituents not forming the absorption edge among R are each independently a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a carboxyl group, an alkyl group, an alkoxy group, an aryl group, an arylalkyl group, an alkylcarbonylamino group, an arylalkylcarbonylamino group, a haloalkylsulfonylamino group, an alkylsulfonylamino group, an arylalkylsulfonylamino group, or an amino group; 17 and R 18 are each independently a hydrogen atom, a halogen atom, or an alkyl group, or are linked together to form a cyclic structure; R 19 ~R 23 are each independently a hydrogen, a halogen or an alkyl group, and n is a number of 1 or more. 【Chemistry 3】 3 In Chemical Formula 3, L 1 is linked to the nitrogen atom of formula 2, 1 ~A 3 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryl group, or an arylalkyl group; L 1 , -U 1- T 1- U 2- T 2- U 3- And T 1 and T 2 are each independently an oxygen atom or absent; U 1 ~U 3 are each independently an alkylene group, an alkylidene group, an alkenylene group, an alkynylene group, or absent.

6. In Chemical Formula 2, R 9 and R 10 6. The absorbent of claim 5, wherein is a substituent of formula (3).

7. 2. The absorbent of claim 1, which exhibits an absorption maximum in the wavelength range of 600 nm to 950 nm.

8. 2. The absorbent according to claim 1, having a 5% thermal decomposition temperature of 190°C or higher.

9. A composition comprising a resin component and the absorbent of claim 1.

10. The composition according to claim 9, wherein the resin component comprises at least one selected from the group consisting of cycloolefin (COP) resins, polyester resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyparaphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyetherimide resins, polyamideimide resins, acrylic resins, polycarbonate resins, polyethylene naphthalate resins, and silicone resins.

11. The composition of claim 9 further comprising a solvent.

12. An absorbent film comprising a resin component and the absorbent of claim 1.

13. 13. The absorbing film according to claim 12, wherein the resin component comprises at least one selected from the group consisting of cycloolefin (COP)-based resins, polyester resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyparaphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyetherimide resins, polyamideimide resins, acrylic resins, polycarbonate resins, polyethylene naphthalate resins and silicone resins.

14. The absorbing film of claim 12, which exhibits an absorption maximum in the wavelength range of 600 nm to 950 nm.

15. 13. The absorbing film according to claim 12, wherein the absolute value of ΔA in the formula (1) is 10% or less. [Formula 1] ΔA=100×(A f -A i ) / A i In formula 1, A f is the transmittance at the absorption maximum wavelength of the absorbing film kept at 85° C. and 85% relative humidity for 120 hours, and A i is the transmittance at the absorption maximum wavelength of the absorbing film before being held at 85° C. and 85% relative humidity for 120 hours, and the absorption maximum wavelength is in the wavelength range of 600 nm to 950 nm.

16. The absorbing film according to claim 12, wherein the absolute value of Δλ in the following formula 2 is 10% or less. [Formula 2] Δλ=100×(λ) f -l i ) / l i In Equation 2, λ f is the absorption maximum wavelength of the absorbing film kept at 85° C. and 85% relative humidity for 120 hours, λ i is the absorption maximum wavelength of the absorbing film before being held at 85° C. and 85% relative humidity for 120 hours, and the absorption maximum wavelength is in the wavelength range of 600 nm to 950 nm.

17. A base layer; An optical filter comprising: an absorbing film according to claim 12 formed on one or both surfaces of the base layer.

18. A solid-state imaging device comprising the optical filter according to claim 17.

19. An infrared sensor comprising an absorbing film according to claim 12.

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