Compounds for light absorbers

By developing deuterium-substituted diammonium salt-based compounds mixed with resin components to form a resin film, the problem of unstable light absorption characteristics of existing light absorbers in high temperature and high humidity environments is solved, and the optical performance that maintains stable under high temperature and high humidity conditions is achieved.

CN120157599APending Publication Date: 2025-06-17LMS
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Patent Information

Application Number
CN202411596066.1
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Priority Date
2023-12-14
Filing Date
2024-11-11
Publication Date
2025-06-17

AI Technical Summary

Technical Problem

The existing light absorber compounds are difficult to maintain stable light absorption characteristics under high temperature and high humidity environments, and there is a problem of low solubility and the need for additional dispersion equipment.

Method used

A compound represented by Formula 1 is developed, which contains a deuterium substituted diammonium salt-based structure, has excellent heat resistance and light absorption characteristics, and is mixed with the resin components to form a resin film for use in optical filters and infrared sensors.

Benefits of technology

Maintaining stable light absorption characteristics under high temperature and high humidity conditions, improving the heat resistance and optical performance of the resin film, and is suitable for optical filters and infrared sensors.

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Abstract

The present specification discloses light absorber compounds and uses thereof. The present specification can provide a compound having excellent heat resistance and capable of stably maintaining light absorption characteristics even under high-temperature conditions or high-temperature and high-humidity conditions. The present specification may also provide a resin film that ensures desired optical properties by coating the compound. The present specification also provides compounds useful as light absorbers for optical filters.
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Description

[0001] Cross - reference to related applications

[0002] This application is based on and claims priority to Korean Patent Application No. 10-2023-0181998, filed with the Korean Intellectual Property Office on December 14, 2023, the disclosure of which is incorporated herein by reference in its entirety. Technical Field

[0003] This specification relates to light absorber compounds and their uses. Background Art

[0004] Compounds that can be used as light absorbers, such as compounds capable of absorbing light in the infrared region, can be applied to various applications. For example, since image capture devices or infrared sensors using a CCD (Charge-Coupled Device) or CMOS (Complementary Metal Oxide Semiconductor) image sensor include silicon photodiodes that are sensitive to the near-infrared region, they can use light absorbers.

[0005] Regarding light absorbers, for example, phthalocyanine-based, cyanine-based, and metal dithiol complex-based, squarylium-based, and diammonium salt-based compounds are known. Phthalocyanine compounds are known as near-infrared compounds, but they have a problem of high absorption in the visible light region. In addition, cyanine-based compounds have a problem in that since the near-infrared region that can be absorbed by a single compound is narrow, they must be used in combination with other compounds. In addition, since metal dithiol complex-based compounds have low solubility, additional dispersion equipment is required when they are applied to a film, and thus it is difficult to apply them to applications that require high permeability.

[0006] In addition, squarylium-based compounds are known to be compounds having excellent heat resistance. However, squarylium-based compounds are difficult to absorb light in the long wavelength range of 900 nm or longer. In addition, immonium or diammonium-based compounds are known to be compounds that can absorb light having a wavelength of 900 nm or longer. However, due to low thermal stability, immonium or diammonium-based compounds have a problem of losing their light absorption characteristics in a high-temperature and / or high-humidity environment.

[0007] To solve the above difficulties, the present invention can disclose compounds and their uses, which can provide such compounds that have excellent heat resistance and can stably maintain light absorption characteristics even when maintained under high-temperature conditions or high-temperature and high-humidity conditions. In addition, this specification can also provide a resin film that ensures required optical properties by coating the above compounds. Summary of the Invention

[0008] This specification discloses compounds and their uses.

[0009] The object of the present specification is to disclose a compound having excellent heat resistance and capable of stably maintaining light absorption characteristics even under high-temperature conditions or high-temperature and high-humidity conditions.

[0010] Another object of the present specification is to provide a resin film that ensures required optical properties by coating the compound.

[0011] Still another object of the present specification is to disclose the uses of these compounds.

[0012] According to one embodiment of the present invention, there is provided a light absorber composition containing a compound represented by Formula 1:

[0013] [Formula 1]

[0014]

[0015] wherein R1 to R 28 are each independently hydrogen, deuterium, alkyl, alkenyl, alkynyl, alkoxy, aryl, aryloxy, arylamino, alkylamino, heteroaryl, alkylsilyl, arylsilyl, amino, nitro, nitrile, hydroxy or cyano; and at least one of R1 to R 28 is deuterium.

[0016] In one embodiment, the deuterium substitution rate of the compound is 10% or higher.

[0017] In one embodiment, the compound exhibits a maximum absorption in the wavelength range of about 690 nm to 1,200 nm.

[0018] In one embodiment, the transmittance of the compound at the maximum absorption is about 50% or lower.

[0019] In one embodiment, the molar mass of the compound is about 900 g / mol to 3,000 g / mol.

[0020] In one embodiment, the 5% pyrolysis temperature of the compound is at least about 285°C.

[0021] In one embodiment, the compound further contains an anion.

[0022] In one embodiment, the resin film contains a resin component and the compound.

[0023] In one embodiment, the resin component for the resin film further comprises at least one or more selected from the group consisting of: cycloolefin resin, polyarylate resin, polyester resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyetherimide resin, polyamideimide resin, acrylic resin, polycarbonate resin, polyethylene naphthalate resin, and silicone resin.

[0024] In one embodiment, the resin component for the resin film comprises a cycloolefin resin.

[0025] In one embodiment, the compound for the resin film further contains an anion.

[0026] In one embodiment, relative to 100 parts by weight of the resin component, the content of the compound in the resin film is 0.001 to 10 parts by weight.

[0027] In one embodiment, the resin film exhibits a maximum absorption in the wavelength range of about 690 nm to 1,200 nm.

[0028] In one embodiment, the absolute value of ΔA of the resin film in Equation 1 is about 80% or less:

[0029] [Equation 1]

[0030] △A = 100×(A f -A i ) / A i ,

[0031] where A f is the transmittance at the maximum absorption wavelength of the resin film after being kept at 85 °C and 85% relative humidity for 120 hours, and A i is the transmittance at the maximum absorption wavelength of the resin film before being kept at 85 °C and 85% relative humidity for 120 hours.

[0032] In one embodiment, the absolute value of Δλ of the resin film in Equation 2 is about 10% or less:

[0033] [Equation 2]

[0034] △λ = 100×(λ f -λ i ) / λ i ,

[0035] where λ f is the maximum absorption wavelength of the resin film after being kept at 85 °C and 85% relative humidity for 120 hours, and λ iis the maximum absorption wavelength of the resin film before being kept at 85 °C and 85% relative humidity for 120 hours.

[0036] In one embodiment, the maximum absorption wavelength of the resin film lies in the wavelength range of about 690 nm to 1,200 nm.

[0037] In one embodiment, the filter includes a substrate and a resin film formed on one or both sides of the substrate.

[0038] In one embodiment, the image capturing device includes the filter.

[0039] In one embodiment, the infrared sensor includes the resin film. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] Figures 1 to 3 is a diagram showing an exemplary structure of the filter of the present invention.

[0041] Figures 4 to 7 is a spectrum showing the light absorption characteristics of the resin film containing the compound of the embodiment or comparative example before and after high temperature and high humidity evaluation. DETAILED DESCRIPTION

[0042] For those physical properties whose measurement temperature results may have an impact in the present invention, unless otherwise specified, it is measured at room temperature. The term "room temperature" used in the present invention refers to the natural temperature without intentional heating or cooling. For example, it refers to any temperature within the range of 10 °C to 30 °C, a temperature of about 23 °C or about 25 °C. In addition, in this specification, unless otherwise specified, the temperature unit is degrees Celsius (°C).

[0043] In the case of physical properties whose measurement humidity results have an impact, the physical properties are those measured under natural humidity without special control at room temperature and / or atmospheric pressure. The term "atmospheric pressure" refers to the natural pressure without intentional pressurization or decompression. It generally represents an atmosphere of about 1 atmosphere, with a value of about 700 mmHg to 800 mmHg.

[0044] Among the physical properties mentioned in this specification, if humidity has an impact on the results, unless otherwise specified, the relevant physical properties are measured under standard humidity. The humidity under standard conditions refers to any humidity within the range of 40% to 60% relative humidity. For example, a relative humidity of about 40% or 60%.

[0045] In the case of optical properties (such as refractive index) mentioned in this specification that vary according to wavelength, unless otherwise specifically stated, the optical properties are those of light with a wavelength of 520 nm.

[0046] In this specification, unless otherwise specified, the term "transmittance" or "absorbance" refers to the actual transmittance (actual transmittance ratio) or actual absorbance (actual absorbance ratio) confirmed at a specific wavelength or within a wavelength range of a specific region. It is the transmittance or absorbance with respect to an incident angle of 0°.

[0047] Unless otherwise specifically stated, the term "average transmittance" or "average absorbance" is the result obtained from the arithmetic mean of the measured transmittance or absorbance while increasing the wavelength by 1 nm starting from the shortest wavelength within a given wavelength range and measuring the transmittance or absorbance at each wavelength. For example, the average transmittance or average absorbance in the wavelength range of 350 nm to 360 nm can represent the arithmetic mean of the transmittance or absorbance measured at 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.

[0048] The term "maximum transmittance" or "maximum absorbance" refers to the maximum transmittance or maximum absorbance when measuring the transmittance or absorbance at each wavelength while increasing the wavelength by 1 nm starting from the shortest wavelength within a certain wavelength range. For example, the maximum transmittance or maximum absorbance in the wavelength range of 350 nm to 360 nm can refer to the highest transmittance or absorbance among the transmittances measured at 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.

[0049] The term "minimum transmittance" or "minimum absorbance" refers to the minimum transmittance or minimum absorbance when measuring the transmittance or absorbance at each wavelength while increasing the wavelength by 1 nm starting from the shortest wavelength within a certain wavelength range. For example, the minimum transmittance or minimum absorbance in the wavelength range of 350 nm to 360 nm can refer to the lowest transmittance or absorbance among the transmittances or absorbances measured at 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.

[0050] The term "incident angle" is the angle measured with respect to the normal of the surface to be evaluated. For example, the transmittance when the incident angle of the filter is 0° refers to the transmittance of light incident along a direction substantially parallel to the normal of the filter surface. This definition of the incident angle also applies to other properties such as transmittance and absorbance.

[0051] In this specification, the term "alkyl" refers to an alkyl group having 1 to 30 carbon atoms, 1 to 24 carbon atoms, 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 can be straight-chain, branched-chain, or cyclic. The alkyl group can be optionally substituted with one or more substituents. Unless otherwise specified, these apply to all alkyl groups mentioned in the specification.

[0052] In this specification, the term "alkenyl" refers to an alkenyl group having 2 to 30 carbon atoms, 2 to 24 carbon atoms, 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 can be straight-chain, branched-chain, or cyclic. The alkenyl group can be optionally substituted with one or more substituents. Unless otherwise specified, these apply to all alkenyl groups mentioned in the specification.

[0053] In this specification, the term "alkynyl" refers to 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 can be straight-chain, branched-chain, or cyclic. The alkynyl group can be optionally substituted with one or more substituents. Unless otherwise specified, these apply to all alkynyl groups mentioned in the specification.

[0054] In this specification, the term "alkoxy" refers to an alkoxy group having 1 to 30 carbon atoms, 1 to 24 carbon atoms, 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 can be straight-chain, branched-chain, or cyclic. The alkoxy group can be optionally substituted with one or more substituents. Unless otherwise specified, these apply to all alkoxy groups mentioned in the specification.

[0055] In this specification, the term "aryl" refers to a monovalent moiety derived from an aromatic hydrocarbon, and the aryl group can be an aryl group having 6 to 48 carbon atoms, 6 to 42 carbon atoms, 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. For example, it can be phenyl, tolyl, xylyl, or naphthyl. The aryl group can be optionally substituted with one or more substituents. Unless otherwise specified, these apply to all aryl groups mentioned in the specification.

[0056] In addition, in this specification, the aryl group can be, for example, a heteroaryl group, and the heteroaryl group is a structure that includes heteroatoms (such as O, N, or S) in addition to carbon atoms in the ring structure of the aryl group. The heteroaryl group can be optionally substituted with one or more substituents. Unless otherwise specified, these apply to all heteroaryl groups mentioned in the specification.

[0057] This specification discloses a compound. The compound can be a light absorber. The term "light absorber" refers to a compound that can absorb light within any wavelength range.

[0058] The compound can be a compound represented by the following formula 1.

[0059] [Formula 1]

[0060]

[0061] In formula 1, R1 to R 28 can each independently be hydrogen, deuterium, alkyl, alkenyl, alkynyl, alkoxy, aryl, aryloxy, arylamino, alkylamino, heteroaryl, silyl, amino, nitro, nitrile, hydroxy or cyano.

[0062] The silyl can be a silyl in which at least one alkyl is bonded to silicon (alkylsilyl), or a silyl in which at least one aryl is bonded to silicon (arylsilyl).

[0063] The alkyl, alkenyl, alkynyl, alkoxy, aryl, aryloxy, arylamino, alkylamino, heteroaryl, alkylsilyl or arylsilyl of formula 1 can optionally be substituted by one or more substituents. The substituents to be substituted at this time can include, for example, deuterium, boron, halogen, hydroxy, nitro, phosphoryl, alkyl, alkenyl, alkynyl, heteroalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, arylsilyl and aryloxy, but are not limited thereto.

[0064] More specifically, in formula 1, R1 to R 20 can be hydrogen, deuterium, alkyl, alkenyl, alkynyl, alkyl substituted by deuterium, alkenyl substituted by deuterium or alkynyl substituted by deuterium, but are not limited thereto. These substituents can be the same as those described above for R1 to R 28 stated.

[0065] In addition, in formula 1, any pair of substituents of R1 to R 28 (for example, adjacent substituents to each other) can combine with each other to form an aliphatic, aromatic, aliphatic heterocyclic or aromatic heterocyclic fused ring structure. The pair of adjacent substituents can refer to a pair of any one substituent and a substituent substituted on the atom directly connected to the atom substituted by the substituent, a pair of any one substituent and a substituent spatially closest to the substituent, or a pair of any one substituent and another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring or two substituents substituted on the same carbon in an aliphatic ring can correspond to adjacent groups to each other.

[0066] In addition, since Formula 1 includes an absorption edge, it can have a structure capable of absorbing light of a desired wavelength. For example, the absorption edge can be a framework or structure having a so-called resonance structure and / or conjugated bonds.

[0067] The optical absorption of light by a compound, particularly an organic compound, is caused by the energy difference (ΔE) between the ground state and the excited state. This can also be explained by the energy difference between the HOMO (highest occupied molecular orbital) and the LUMO (lowest unoccupied molecular orbital).

[0068] Generally, an organic absorber can include a resonance structure and / or conjugated bonds as an absorption edge, which can exhibit a light absorption effect. Thus, the compound can form a framework that generally allows the desired light absorption characteristics to be exhibited.

[0069] There is no particular limitation on the specific type of the above absorption edge or framework. It is well known that the resonance effect refers to the interaction between the lone pair electrons of a molecule and the π-bond electrons of an adjacent group, and the substituents or frameworks that cause such a resonance effect are well known. In addition, a conjugated bond is a system composed of two or more double bonds with a single bond between them, and it is well known that as the length of this conjugated bond increases, the energy difference between the HOMO and the LUMO decreases, resulting in a shift of the absorption band to the long wavelength side.

[0070] For example, the absorption edge can be a framework or structure that allows the compounds disclosed in this specification to exhibit maximum absorption in the wavelength range of 690 nm to 1,200 nm.

[0071] The compounds disclosed in this specification can exhibit a maximum absorption wavelength in the range of 690 nm to 1,200 nm. In other examples, the lower limit of the maximum absorption wavelength can be about 690 nm, 700 nm, 710 nm, 720 nm, 730 nm, 740 nm, 750 nm, 760 nm, 770 nm, 780 nm, 790 nm, 810 nm, 820 nm, 830 nm, 840 nm, 850 nm, 860 nm, 870 nm, 880 nm, 890 nm, 900 nm, 910 nm, or 920 nm. In addition, the upper limit of the maximum absorption wavelength can be about 1,200 nm, 1,190 nm, 1,180 nm, 1,170 nm, 1,160 nm, 1,150 nm, 1,140 nm, 1,130 nm, 1,120 nm, or 1,100 nm. The maximum absorption wavelength can be in a range equal to and longer or longer than any of the above lower limits; it can be in a range equal to and longer or longer than any of the above lower limits and equal to and shorter or shorter than any of the above upper limits.

[0072] As described above, the resonance structure and the conjugated bond are determined by 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). Since the energy difference is determined and the maximum absorption wavelength is determined by this energy difference, the structure of the absorption edge can be determined such that the compound can have a maximum absorption wavelength within the above range.

[0073] The compounds disclosed in this specification may include deuterium of at least one of R1 to R in Formula 1. 28 Here, "including deuterium" means including the case where at least one of R1 to R 28 is deuterium; at least one of R1 to R 28 is an alkyl group, where at least one hydrogen is replaced by deuterium; at least one of R1 to R 28 is an alkenyl group, where at least one hydrogen is replaced by deuterium; at least one of R1 to R 28 is an alkynyl group, where at least one hydrogen is replaced by deuterium; at least one of R1 to R 28 is an alkoxy group, where at least one hydrogen is replaced by deuterium; at least one of R1 to R 28 is an aryl group, where at least one hydrogen is replaced by deuterium; at least one of R1 to R 28 is an aryloxy group, where at least one hydrogen is replaced by deuterium; at least one of R1 to R 28 is an arylamino group, where at least one hydrogen is replaced by deuterium; at least one of R1 to R 28 is an alkylamino group, where at least one hydrogen is replaced by deuterium; at least one of R1 to R 28 is a heteroaryl group, where at least one hydrogen is replaced by deuterium; at least one of R1 to R 28 is an alkylsilyl group, where at least one hydrogen is replaced by deuterium; or at least one of R1 to R 28 is an arylsilyl group, where at least one hydrogen is replaced by deuterium.

[0074] Due to the deuterium contained in R1 to R 28 , the compound represented by Formula 1 can ensure excellent heat resistance without affecting the light absorption characteristics of the compound. More specifically, due to the deuterium contained in R1 to R 20 , the compound represented by Formula 1 can ensure excellent heat resistance.

[0075] The lower limit of the number of deuterium contained in R1 to R of Formula 1 28 can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20. The R1 to R of Formula 1 28The upper limit of the amount of tritium contained therein can be 200, 100, 90, 80, 70, 60, 50, 40, 30, 20, 19, 18, 17, 16, 15, 10, 9, 8, 7, 6, 5 or 4. The amount of deuterium can be in the range equal to and greater than or greater than any one of the above lower limits; in the range equal to and less than or less than any one of the above upper limits; or in the range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits.

[0076] The deuterium substitution rate of the compounds disclosed in this specification can be higher than a certain level. The deuterium substitution rate is theoretically the ratio of the number of moles of deuterium after deuterium substitution based on the number of moles of all hydrogens contained in one mole of the compound before deuterium substitution. The lower limit of the deuterium substitution rate can be about 10%, 15%, 20%, 25%, 30%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 100%, and the upper limit can be about 100%, 99%, 98%, 97%, 96%, 95%, 94%, 93%, 92%, 91%, 90%, 85%, 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25% or 20%. This ratio can be in the range equal to and greater than or greater than any one of the above lower limits; in the range equal to and less than or less than any one of the above upper limits; or in the range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits. In addition, the deuterium substitution rate can refer to how many hydrogen atoms directly bonded to carbon atoms are replaced by deuterium atoms. The method for measuring this deuterium substitution rate is described in "5. Deuterium Substitution Rate" of the embodiments of this specification.

[0077] The compounds disclosed in this specification can ensure heat resistance by controlling the deuterium substitution rate. The bond between carbon and deuterium has lower stretching and bending energies than the bond between carbon and hydrogen. Therefore, it can be understood that compared with the bond between carbon and hydrogen, the bond between carbon and deuterium can reduce the intramolecular vibration energy, thereby ensuring heat resistance by maintaining the light absorption characteristics even in a high-temperature and high-humidity environment.

[0078] The compound can have an appropriate molar mass level. For example, the lower limit of the molar mass can be about 900 g / mol, 950 g / mol, 1,000 g / mol, 1,100 g / mol, 1,150 g / mol, 1,200 g / mol, 1,250 g / mol, 1,300 g / mol, 1,350 g / mol, 1,400 g / mol, 1,450 g / mol, 1,460 g / mol, 1,470 g / mol, 1,480 g / mol, 1,490 g / mol or 1,500 g / mol. The upper limit of the molar mass can be about 3,000 g / mol, 2,900 g / mol, 2,800 g / mol, 2,700 g / mol, 2,600 g / mol, 2,500 g / mol, 2,400 g / mol, 2,300 g / mol, 2,200 g / mol, 2,100 g / mol, 2,000 g / mol, 1,900 g / mol, 1,800 g / mol, 1,700 g / mol, 1,600 g / mol, 1,500 g / mol or 1,490 g / mol. The molar mass can be in the range equal to and greater than or greater than any of the above lower limits; in the range equal to and less than or less than any of the above upper limits; or in the range equal to and greater than or greater than any of the above lower limits and equal to and less than or less than any of the above upper limits.

[0079] The compound can have excellent heat resistance. For example, the 5% thermal decomposition temperature (hereinafter referred to as "Td5%") of the compound can be within a predetermined range. For example, the lower limit of Td 5% of the above compound can be about 285 °C, 286 °C, 287 °C, 288 °C, 289 °C, 290 °C, 291 °C, 292 °C, 293 °C, 294 °C, 295 °C, 296 °C, 297 °C, 298 °C, 299 °C or 300 °C. The upper limit of Td 5% can be about 500 °C, 480 °C, 460 °C, 440 °C, 420 °C, 400 °C, 380 °C, 360 °C, 350 °C, 340 °C, 330 °C, 320 °C, 310 °C, 300 °C or 290 °C. Td 5% can be in the range equal to and higher than or higher than any of the above lower limits; in the range equal to and lower than or lower than any of the above upper limits; or in the range equal to and higher than or higher than any of the above lower limits and equal to and lower than or lower than any of the above upper limits.

[0080] Td 5% is the temperature at which 95% mass loss occurs in the thermogravimetric analysis (TGA) of the compound. Such Td 5% is obtained by thermogravimetric analysis (TGA), and the thermogravimetric analysis (TGA) method is described in "3. Thermal Decomposition Temperature (Td 5%) Analysis" of the embodiments of this specification.

[0081] The compound may contain anions. Examples of anions may include halogen anions, hexafluoroantimonate anions (SbF 6- ), perchlorate anions, thiocyanate anions (SCN - ), hexafluorophosphate anions (PF 6- ), phosphate anions, bis(trifluoromethanesulfonyl)imide anions, tetrafluoroborate anions (BF 4- ), trifluoromethylcarboxylate anions, alkylsulfonate anions, benzenesulfonate anions, toluenesulfonate anions, benzenecarboxylate anions, alkylcarboxylate anions, periodate anions, hydrofluoroborate anions, and tetraphenylborate anions, but are not limited thereto.

[0082] The above compound can be obtained by known organic compound synthesis methods and deuterium substitution methods.

[0083] The structure of Formula 1 is the structure of an absorbent called a so-called diammonium salt-based compound. Various methods for producing diammonium salt-based compounds are known industrially. Thus, for example, the compound of Formula 1 replaces the reactants used in the production process of a known diammonium salt-based absorbent with deuterium, and can be manufactured by applying the reactant to the absorbent synthesis process. In addition, for example, the compound can be prepared by synthesizing a diammonium salt-based absorbent according to a known synthesis method and then replacing at least part or all of the hydrogen in the synthesized absorbent with deuterium.

[0084] There is no particular limitation on the above deuterium substitution method. For example, a method of mixing the compound to be deuterium-substituted with deuterium at an appropriate temperature can be applied. The lower limit of the mixing temperature can be, for example, about 90 °C, 95 °C, 100 °C, 105 °C, 110 °C, 115 °C, or 120 °C, and the upper limit can be about 300 °C, 280 °C, 260 °C, 240 °C, 220 °C, 200 °C, 180 °C, 160 °C, 140 °C, or 120 °C. The mixing temperature can be in a range equal to and higher than or higher than any one of the above lower limits; in a range equal to and lower than or lower than any one of the above upper limits; or in a range equal to and higher than or higher than any one of the above lower limits and equal to and lower than or lower than any one of the above upper limits.

[0085] The mixing time may not be particularly limited, and for example, it can be adjusted by considering the required substitution rate and the like. For example, the lower limit of the mixing time can be about 3 hours, 6 hours, 9 hours, 12 hours, 15 hours, 18 hours, 21 hours or 24 hours, and the upper limit can be about 72 hours, 36 hours or 24 hours. The mixing time can be within a range equal to and greater than or greater than any one of the above lower limits; within a range equal to and less than or less than any one of the above upper limits; or within a range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits.

[0086] In addition, the mixing can be carried out in the presence of additional compounds that can, for example, assist, facilitate, or initiate deuterium substitution. For example, the compounds used as catalysts for deuterium substitution can include any one of the following: silver oxide (Ag2O), silver acetate (AgOAc), silver trifluoroacetate (CF3COOAg), silver carbonate (Ag2CO3), and palladium acetate (Pd(OAc)2), palladium chloride (PdCl2), bis(acetonitrile)dichloropalladium (PdCl2(CH3CN)2), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), and bis(dibenzylideneacetone)palladium (Pd(dba)2), but there is no particular limitation as long as the compound can act as a catalyst during the deuterium substitution process.In addition, the compound acting as a ligand in the deuterium substitution process may include, for example, any one of the following: allyldiphenylphosphine, allyldiphenylphosphine oxide, benzyldiphenylphosphine, 1-[2-[bis(tert-butyl)phosphino]phenyl]-3,5-diphenyl-1H-pyrazole, bis[2-(diadamantylphosphino)ethyl]amine, bis(5H-dibenzo[a,d]cyclohepten-5-yl)phenylphosphine, bis(5-H-dibenzo[a,d]cyclohepten-5-yl)phenylphosphine, 2-[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]benzaldehyde, 2,6-bis(di-tert-butylphosphinomethyl)pyridine, bis(dicyclohexylphosphinophenyl)ether, bis(diethylamino)phenylphosphine, 1,3-bis-(2,6-diisopropylphenyl)-[1,3,2]diazaphospholane 2-oxide, bis(dimethylamino)chlorophosphine, 2-[bis(3,5-dimethylphenyl)phosphino]benzaldehyde, 2,2'-bis(diphenylphosphino)-1,1'-biphenyl, bis(4-fluorophenyl)phenylphosphine oxide, bis[4-(3,3,4,4,5,5,5-heptafluoro-2,2-bis(trifluoromethyl)pentyl)phenyl]phenylphosphine, 1,1'-bis(phenylphosphino)ferrocene, (2-bromophenyl)dicyclohexylphosphine, (2-bromophenyl)diphenylphosphine, tert-butyldicyclohexylphosphine, tert-butyldiisopropylphosphine, tert-butyldiphenylphosphine, di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine, 2-chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholane, 2-dicyclohexylphosphino-2',6'-bis(N,N-dimethylamino)biphenyl, 1-(dicyclohexylphosphino)-2,2-diphenyl-1-methylcyclopropane, dicyclohexyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine, cyclohexyldiphenylphosphine, 2-(dicyclohexylphosphino)-1,1-diphenyl-1-propene, dicyclohexyl(1-methyl-2,2-diphenylvinyl)phosphine, di(1-adamantyl)-2-dimethylaminophenylphosphine, di-1-adamantylphosphine, di(1-adamantyl)-(2-triisopropylsilyloxyphenyl)phosphine, (5H-dibenzo[a,d]cyclohepten-5-yl)diphenylphosphine, (R)-(-)-1-[(S)-2-(bis(3,5-bistrifluoromethylphenyl)phosphino)ferrocene]ethyldicyclohexylphosphine, (R)-(-)-1-[(S)-2-(bis(3,5-bistrifluoromethylphenyl)phosphino)ferrocene]ethylbis(3,5-dimethylphenyl)phosphine, P,P-dichlorodiferrocenylphosphine, (R)-(-)-N,N-dimethyl-1-[(S)-2-(diphenylphosphino)ferrocene]ethylamine, and 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene, but not limited thereto, as long as it is a compound that can be used as a ligand in the deuterium substitution process.

[0087] This specification also discloses compositions containing these compounds. The term "composition" may refer to a mixture containing the compound and other components, or a mixture containing two or more types of compounds.

[0088] The composition containing this compound essentially includes the compound of formula 1 above, and may additionally contain other necessary components.

[0089] For example, the composition may further include a resin component used as an adhesive. In this case, there is no particular limitation on the type of resin component to be applied, and known resin components for forming a resin film (such as a near-infrared resin film) can be applied. In this specification, the compound component can exhibit appropriate compatibility or solubility with various known resin components.

[0090] Examples of the resin component may include one or more selected from the following: cycloolefin (COP)-based resin, polyarylate resin, polyester resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyaryletherphosphine oxide resin, polyimide resin, polyetherimide resin, polyamideimide resin, acrylic resin, polycarbonate resin, polyethylene naphthalate resin, or silicone resin, or various other organic resins or organic-inorganic hybrid resins, but are not limited thereto.

[0091] Although not particularly limited, the compounds of this specification can be mixed with a cycloolefin-based resin among the resin components used as known adhesives to form a resin film showing excellent properties. Therefore, in one example, the resin component may be a cycloolefin-based resin.

[0092] When applying the resin component, there is no particular limitation on its ratio. For example, the resin component may be present such that the weight ratio of the compound to 100 parts by weight of the resin component is in the range of 0.001 part by weight to 10 parts by weight. In other examples, the lower limit of the weight ratio of the compound to 100 parts by weight of the resin component may 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 part by weight, 1.2 part by weight, 1.3 part by weight, or 1.4 part by weight, and the upper limit 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 part by weight. The ratio may be in the range equal to and greater than or greater than any of the above lower limits; in the range equal to and less than or less than any of the above upper limits; or in the range equal to and greater than or greater than any of the above lower limits and equal to and less than or less than any of the above upper limits.

[0093] For example, the composition may further include a solvent in which the compound and / or resin component is dispersed. In this case, there is no particular limitation on the type of solvent to be applied, and any known solvent for forming a resin film (e.g., a near-infrared resin film) can be applied. In the present specification, the compound component may exhibit appropriate compatibility or solubility in various known solvents.

[0094] Examples of the solvent may include dichloromethane, cyclohexanone, toluene, methyl ethyl ketone, methyl isobutyl ketone, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether 3-methoxybutanol, ethylene glycol monobutyl ether acetate, 4-hydroxy-4-methyl-2-pentanone, γ-butyrolactone, pyridone, chloroform, 1,4-dioxane, o-dichlorobenzene, chlorobenzene, fatty alcohols having 2 or more carbon atoms (e.g., isobutanol, isopropanol, ethanol, isopropanol, butanol, etc.), butyl acetate, tetrahydrofuran, or xylene, but are not limited thereto.

[0095] When applying the solvent, there is no particular limitation on the ratio, and the ratio can be adjusted within a range that allows the compound and / or resin component to be appropriately dispersed.

[0096] In addition to the above components, the composition may further contain any other necessary components. Optional components may include, for example, an adhesion promoter, a leveling agent, an antistatic agent, a heat stabilizer, a light stabilizer, an antioxidant, a dispersant, a flame retardant, a lubricant, or a plasticizer, but are not limited thereto.

[0097] The present specification also relates to the use of the compound or composition.

[0098] For example, the present specification may be about a resin film applying the above compound or composition. The resin film may at least contain a resin component and the above compound. In this case, the specific type of the resin component and the ratio of the resin component to the compound are as described in the compound composition section.

[0099] The resin film may be a film capable of absorbing light in a predetermined wavelength range. In one example, the resin film may be an infrared resin film or a near-infrared resin film. For example, such a resin film may exhibit absorption characteristics in at least a part of the wavelength range from about 690 nm to 1,200 nm.

[0100] For example, the resin film can exhibit a maximum absorption wavelength in the range of 690 nm to 1,200 nm. In other examples, the lower limit of the maximum absorption wavelength can be about 690 nm, 700 nm, 710 nm, 720 nm, 730 nm, 740 nm, 750 nm, 760 nm, 770 nm, 780 nm, 790 nm, 810 nm, 820 nm, 830 nm, 840 nm, 850 nm, 860 nm, 870 nm, 880 nm, 890 nm, 900 nm, 910 nm, or 920 nm. Additionally, the upper limit of the maximum absorption wavelength can be about 1,200 nm, 1,190 nm, 1,180 nm, 1,170 nm, 1,160 nm, 1,150 nm, 1,140 nm, 1,130 nm, 1,120 nm, or 1,100 nm. The maximum absorption wavelength can be in a range equal to and longer than or longer than any one of the above lower limits; in a range equal to and shorter than or shorter than any one of the above upper limits; or in a range equal to and longer than or longer than any one of the above lower limits and equal to and shorter than or shorter than any one of the above upper limits.

[0101] Due to these properties, the resin film can be applied to various devices such as filters and infrared sensors. Thus, the resin film can provide excellent optical and physical properties to the devices, such as excellent heat resistance.

[0102] For example, the transmittance of the resin film at the absorption maximum can be lower than a certain level. The upper limit can be about 50%, 49%, 48%, 47%, 46%, 45%, 44%, 43%, 42%, 41%, or 40%, and the lower limit can be about 0.1%, 1%, 10%, 15%, 20%, 25%, 30%, 35%, or 39%. The transmittance at the absorption maximum can be in a range equal to and greater than or greater than any one of the above lower limits; in a range equal to and less than or less than any one of the above upper limits; or in a range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits.

[0103] For example, assume that the transmittance of the resin film at the maximum absorption wavelength after being kept at 85 °C and 85% relative humidity for 120 hours is 'A f ', and the transmittance of the resin film at the maximum absorption wavelength before being kept at 85 °C and 85% relative humidity for 120 hours is 'A i ', then the upper limit of the absolute value of A f - A i can be about 40%, 35%, 30%, 25%, 20%, 15%, 10%, or 5%, and the lower limit can be about 0%, 5%, 10%, 15%, 20%, or 25%. A f - Ai The absolute value can be within a range equal to and greater than or greater than any one of the above lower limits; within a range equal to and less than or less than any one of the above upper limits; or within a range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits.

[0104] For example, in the resin film, the absolute value of ΔA in Equation 1 can be less than or equal to a predetermined value.

[0105] [Equation 1]

[0106] △A = 100×(A f - A i ) / A i .

[0107] In Equation 1, A f is the transmittance at the maximum absorption wavelength of the resin film after maintaining the resin film at 85 °C and 85% relative humidity for 120 hours, and A i is the transmittance at the maximum absorption wavelength of the resin film before maintaining the resin film at 85 °C and 85% relative humidity for 120 hours. The maximum absorption wavelength exists in the wavelength range of 690 nm to 1,200 nm.

[0108] The upper limit of the absolute value of ΔA in Equation 1 can be about 80%, 70%, 60%, 50%, 45%, 40%, 35%, 30%, 25%, 20%, 15% or 10%, and the lower limit can be about 0%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 20%, 30%, 40%, 50%, 60% or 70%. The absolute value of ΔA can be within a range equal to and greater than or greater than any one of the above lower limits; within a range equal to and less than or less than any one of the above upper limits; or within a range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits.

[0109] In Equation 1, A f 's upper limit can be about 80%, 75%, 70%, 65%, 60%, 55%, 50% or 45%, and the lower limit can be about 10%, 20%, 30%, 40%, 50%, 60% or 65%. A f can be within a range equal to and greater than or greater than any one of the above lower limits; within a range equal to and less than or less than any one of the above upper limits; or within a range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits.

[0110] In the resin film, the absolute value of Δλ in Equation 2 can be less than or equal to a predetermined value.

[0111] [Equation 2]

[0112] △λ = 100×(λ f - λ i ) / λ i .

[0113] In Equation 2, λ f is the maximum absorption wavelength of the resin film after being kept at 85 °C and 85% relative humidity for 120 hours, and λ i is the maximum absorption wavelength of the resin film before being kept at 85 °C and 85% relative humidity for 120 hours. The maximum absorption wavelength exists in the wavelength range of 690 nm to 1,200 nm.

[0114] The upper limit of the absolute value of △λ in Equation 2 is about 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1% or 0.5%, and the lower limit can be 0%. The absolute value of △λ can be in the range equal to and greater than or greater than any one of the above lower limits; in the range equal to and less than or less than any one of the above upper limits; or in the range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits.

[0115] In Equation 2, λ f and λ i can be respectively in the range of 690 nm to 1,200 nm. In other examples, the lower limit of each of λ f and λ i can be about 690 nm, 700 nm, 710 nm, 720 nm, 730 nm, 740 nm, 750 nm, 760 nm, 770 nm, 780 nm, 790 nm, 810 nm, 820 nm, 830 nm, 840 nm, 850 nm, 860 nm, 870 nm, 880 nm, 890 nm, 900 nm, 910 nm or 920 nm. In addition, the upper limit of λ f and λ i can be respectively about 1,200 nm, 1,190 nm, 1,180 nm, 1,170 nm, 1,160 nm, 1,150 nm, 1,140 nm, 1,130 nm, 1,120 nm or 1,100 nm. λ f and λ iEach of them can be within a range equal to and longer than or longer than any one of the above lower limits; within a range equal to and shorter than or shorter than any one of the above upper limits; or within a range equal to and longer than or longer than any one of the above lower limits and equal to and shorter than or shorter than any one of the above upper limits.

[0116] Due to the absorption characteristics, the resin film can be applied to various devices such as filters and infrared sensors. Therefore, the resin film can enable the devices to effectively achieve the desired performance.

[0117] In this specification, as long as the compounds or compositions of this specification are applied, the resin film can be formed in a known manner. For example, the resin film can be formed by coating the compound composition in an appropriate manner and performing a curing or drying process if necessary.

[0118] There is no particular limitation on the thickness of the resin film, and the thickness can be adjusted considering the desired characteristics. In one example, the thickness of the resin film can be in the range of about 0.5 to 20 μm.

[0119] This specification also relates to a filter. The filter can include a substrate and a resin film formed on one or both sides of the substrate.

[0120] Figure 1 is an example of a filter showing the case where the resin film 200 is formed on one surface of the substrate 100.

[0121] By including the above resin film, the filter of this specification can exhibit excellent performance. For example, the filter can effectively and accurately block unnecessary infrared light and achieve a visible light transmission band with a high transmittance.

[0122] There is no particular limitation on the type of the transparent substrate applied to the filter, and known filter transparent substrates can be used. In one example, the substrate can be a so-called near-infrared absorbing substrate. A near-infrared absorbing substrate is a substrate that exhibits absorption characteristics in at least a part of the near-infrared region. The so-called blue glass is a representative example of a near-infrared absorbing substrate, which exhibits the above characteristics by containing copper. Such a near-infrared absorbing substrate can be used to construct a filter that blocks light in the near-infrared region, but due to its absorption characteristics, it is disadvantageous in ensuring a high transmittance in the visible light region and is also disadvantageous in terms of durability. In this specification, by appropriately selecting a near-infrared absorbing substrate and combining it with a specific resin film, a filter that can effectively block the desired light, exhibits high transmittance characteristics in the visible light region, and has excellent durability can be provided.

[0123] For an infrared absorption substrate, a substrate that exhibits an average transmittance higher than a certain level in the wavelength range of 425 nm to 560 nm can be used. The lower limit of the average transmittance can be about 75%, 77%, 79%, 81%, 83%, 85%, 87% or 89%, and the upper limit can be about 98%, 96%, 94%, 92% or 90%. The average transmittance can be in the range equal to and greater than or greater than any of the above lower limits; in the range equal to and less than or less than any of the above upper limits; or in the range equal to and greater than or greater than any of the above lower limits and equal to and less than or less than any of the above upper limits.

[0124] For an infrared absorption substrate, a substrate that exhibits a maximum transmittance higher than a certain level in the wavelength range of 425 nm to 560 nm can be used. The lower limit of the maximum transmittance can be about 80%, 82%, 84%, 86%, 88% or 90%, and the upper limit can be about 100%, 98%, 96%, 94%, 92% or 90%. The maximum transmittance can be in the range equal to and greater than or greater than any of the above lower limits; in the range equal to and less than or less than any of the above upper limits; or in the range equal to and greater than or greater than any of the above lower limits and equal to and less than or less than any of the above upper limits.

[0125] For an infrared absorption substrate, a substrate that exhibits an average transmittance higher than a certain level in the wavelength range of 350 nm to 390 nm can be used. The lower limit of the average transmittance can be about 75%, 77%, 79%, 81% or 83%, and the upper limit can be about 98%, 96%, 94%, 92%, 90%, 88%, 86% or 84%. The average transmittance can be in the range equal to and greater than or greater than any of the above lower limits; in the range equal to and less than or less than any of the above upper limits; or in the range equal to and greater than or greater than any of the above lower limits and equal to and less than or less than any of the above upper limits.

[0126] For an infrared absorption substrate, a substrate that exhibits a maximum transmittance higher than a certain level in the wavelength range of 350 nm to 390 nm can be used. The lower limit of the maximum transmittance can be about 80%, 82%, 84%, 86% or 87%, and the upper limit can be about 100%, 98%, 96%, 94%, 92%, 90% or 88%. The maximum transmittance can be in the range equal to and greater than or greater than any of the above lower limits; in the range equal to and less than or less than any of the above upper limits; or in the range equal to and greater than or greater than any of the above lower limits and equal to and less than or less than any of the above upper limits.

[0127] Using an infrared absorption substrate, the transmittance at a wavelength of 700 nm can be within a certain range. The lower limit can be about 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26% or 28%, and the upper limit can be about 45%, 43%, 41%, 39%, 37%, 35%, 33%, 31% or 29%. The transmittance can be within a range equal to and greater than or greater than any of the above lower limits; within a range equal to and less than or less than any of the above upper limits; or within a range equal to and greater than or greater than any of the above lower limits and equal to and less than or less than any of the above upper limits.

[0128] The infrared absorption substrate can have an average transmittance in the wavelength range of 700 nm to 800 nm. The lower limit can be about 5%, 7%, 9%, 11%, 13%, 15%, 15.5%, 16% or 16.5%, and the upper limit can be 30%, 28%, 26%, 24%, 22%, 20%, 18% or 17%. The average transmittance can be within a range equal to and greater than or greater than any of the above lower limits; within a range equal to and less than or less than any of the above upper limits; or within a range equal to and greater than or greater than any of the above lower limits and equal to and less than or less than any of the above upper limits.

[0129] For the infrared absorption substrate, the maximum transmittance can be within a specific wavelength range of 700 nm to 800 nm. The lower limit can be about 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26% or 28%, and the upper limit can be about 43%, 41%, 39%, 37%, 35%, 33%, 31% or 29%. The maximum transmittance can be within a range equal to and greater than or greater than any of the above lower limits; within a range equal to and less than or less than any of the above upper limits; or within a range equal to and greater than or greater than any of the above lower limits and equal to and less than or less than any of the above upper limits.

[0130] The infrared absorption substrate can have an average transmittance in the specific wavelength range of 800 nm to 1,000 nm. The lower limit can be about 3%, 5%, 7%, 9% or 11%, and the upper limit can be about 20%, 18%, 16%, 14% or 12%. The average transmittance can be within a range equal to and greater than or greater than any of the above lower limits; within a range equal to and less than or less than any of the above upper limits; or within a range equal to and greater than or greater than any of the above lower limits and equal to and less than or less than any of the above upper limits.

[0131] The infrared absorption substrate may have a maximum transmittance in a specific wavelength range of 800 nm to 1,000 nm. The lower limit may be about 5%, 7%, 9%, 11%, 13% or 15%, and the upper limit may be about 30%, 28%, 26%, 24%, 22%, 20%, 18% or 16%. The maximum transmittance may be in a range equal to and greater than or greater than any one of the above lower limits; in a range equal to and less than or less than any one of the above upper limits; or in a range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits.

[0132] The infrared absorption substrate may have an average transmittance in a specific wavelength range of 1,000 nm to 1,200 nm. The lower limit may be about 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24% or 25%, and the upper limit may be about 50%, 48%, 46%, 44%, 42%, 40%, 38%, 36%, 34%, 32%, 30%, 28% or 26%. The average transmittance may be in a range equal to and greater than or greater than any one of the above lower limits; in a range equal to and less than or less than any one of the above upper limits; or in a range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits.

[0133] The infrared absorption substrate may have a maximum transmittance in a specific wavelength range of 1,000 nm to 1,200 nm. The lower limit may be about 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34% or 36%, and the upper limit may be about 70%, 68%, 66%, 64%, 62%, 60%, 58%, 56%, 54%, 52%, 50%, 48%, 46%, 44%, 42%, 40%, 38% or 36%. The maximum transmittance may be in a range equal to and greater than or greater than any one of the above lower limits; in a range equal to and less than or less than any one of the above upper limits; or in a range equal to and greater than or greater than any one of the above lower limits and equal to and less than or less than any one of the above upper limits.

[0134] The infrared absorption substrate can be combined with the resin film of the present specification to form a desired filter. As such a substrate, a substrate known as so-called infrared absorption glass can be used. This glass is an absorption-type glass manufactured by adding CuO or a similar composition to a fluorophosphate-based glass or a phosphate-based glass. Therefore, in one embodiment of the present specification, a CuO-containing fluorophosphate glass substrate or a CuO-containing phosphate glass substrate can be used as the infrared absorption substrate. Phosphate glass also includes K phosphate glass, in which a part of the glass structure is composed of SiO2. Since such absorption-type glass is well-known, for example, the glass disclosed in Korean Patent No. 10-2056613 or other commercially available absorption-type glass (e.g., commercially available products of Hoya, Schott, PTOT, etc.) can be used.

[0135] This infrared absorption substrate contains copper. In the present specification, a substrate with a copper content in the range of 1 wt% to 7 wt% can be used. In other examples, the copper content can be about 1.5 wt% or higher, 2 wt% or higher, 2.5 wt% or higher, 2.6 wt% or higher, 2.7 wt% or higher, or 2.8 wt% or higher, or 6.5 wt% or lower, 6 wt% or lower, 5.5 wt% or lower. It can be lower than 5 wt%, lower than 4.5 wt%, lower than 4 wt%, lower than 3.5 wt%, lower than 3 wt% or lower than 2.9 wt%. A substrate with such a copper content may exhibit the above optical properties and can be combined with the resin film to form a filter with desired properties.

[0136] The copper content can be confirmed by using X-ray fluorescence analysis equipment (WD XRF, wavelength-dispersive X-ray fluorescence spectrometry). When X-rays are irradiated from the equipment to the sample (substrate), each element of the sample generates characteristic secondary X-rays, and the equipment can detect the secondary X-rays regarding the wavelength of each element. The intensity of the secondary X-rays is proportional to the element content, so quantitative analysis can be performed through the intensity of the secondary X-rays.

[0137] The thickness of the infrared absorption substrate can be adjusted within a wavelength range of, for example, about 0.03 mm to 5 mm, but is not limited thereto.

[0138] In addition to the substrate and the resin film, the filter of the present specification can also include other required known components. For example, the filter can also include a dielectric film. For example, the dielectric layer can additionally include a so-called dielectric layer located on one or both sides of the substrate.

[0139] Figure 2 and Figure 3 are examples of filters with a dielectric film 300 added, and show the case where the dielectric layer 300 is formed on one or both sides of a stacked structure including a substrate 100 and a resin film 200.

[0140] This dielectric film is a film composed of repeatedly stacking a dielectric material with a low refractive index and a dielectric material with a high refractive index. It is also used to form a so-called IR reflection layer and an antireflection (AR) layer. In this specification, this known IR reflection layer or the dielectric film for forming an AR layer can be applied.

[0141] Therefore, the dielectric film can have a multilayer structure that includes at least two types of sublayers, each sublayer having a different refractive index, and can include a multilayer structure in which two types of sublayers are repeatedly stacked.

[0142] The material for forming the dielectric film, in other words, the material for forming each sublayer, is not particularly limited, and known materials can be applied. Generally, SiO2 or fluorides such as Na5Al3F14, Na3AlF6, or MgF2 can be used to manufacture the low-refractive-index sublayer, and amorphous silicon, TiO2, Ta2O5, Nb2O5, ZnS, or ZnSe, etc. can be used to manufacture the high-refractive-index sublayer, but the materials applied in this specification are not limited thereto.

[0143] The method for forming the above dielectric film is not particularly limited, and for example, it can be formed by applying a known deposition method. In the industry, there are known methods for controlling the reflection or transmission characteristics of the dielectric film by considering the deposition thickness or the number of layers of the sublayer, and in this specification, the dielectric film can be formed according to this known method.

[0144] In addition, the filter can further include a resin film exhibiting ultraviolet absorption characteristics (referred to as an ultraviolet resin film) as a resin film different from the above resin film. However, this resin film may not be an essential component, and for example, an ultraviolet compound described later can be introduced into one resin film together with the compound of Formula 1.

[0145] In one example, the ultraviolet resin film can be designed to exhibit maximum absorption in the wavelength range of about 300 nm to 390 nm. The ultraviolet resin film can contain only an ultraviolet compound, or if necessary, can contain two or more types of ultraviolet compounds.

[0146] For example, as the ultraviolet compound, a known compound that exhibits maximum absorption in the wavelength range of about 300 nm to 390 nm can be used. The material and the construction method for constructing such an ultraviolet resin film are not particularly limited, and known materials and construction methods can be applied.

[0147] Generally, an ultraviolet resin film is formed by using a material obtained by mixing a transparent resin and an ultraviolet compound capable of exhibiting a desired maximum absorption. At this time, the transparent resin can be a resin component applied to the compound composition. In addition to the above layers, the filter may include various necessary layers within a range that does not impair the desired effects.

[0148] This specification also relates to an image capturing device including a filter. At this time, the configuration of the image capturing device or the application method of the filter is not particularly limited, and known configurations and application methods can be applied.

[0149] Furthermore, the use of the filter of this specification is not limited to image capturing devices. It can be applied to various other applications that require near-infrared cutting, such as display devices including PDPs.

[0150] This specification also relates to an infrared sensor including a resin film. The configuration of the infrared sensor is not particularly limited as long as it includes the resin film disclosed in this specification. For example, it can be configured by introducing the resin film of this specification into a known motion sensor, proximity sensor, or gesture sensor.

[0151] In addition, the use of the compound composition or resin film of this specification is not limited to filters, infrared sensors, and / or image capturing devices. It can also be applied to various other applications that require infrared cutting, such as electronic components such as LiDAR.

[0152] The compounds disclosed in this specification will be described in detail through examples and comparative examples, but the scope of the compounds is not limited by the examples.

[0153] 1. Maximum Absorption Measurement Method

[0154] The maximum absorption of the compound is evaluated by a conventional method. Specifically, the sample (compound) is dissolved in chloroform at a concentration of about 10 -5 M, and then evaluated by using a measuring device (Agilent, Varian Cary 4000).

[0155] 2. Transmittance Spectrum Evaluation

[0156] The absorption maximum of the compound was measured from the sample using a spectrophotometer (Perkinelmer, Lambda 750 spectrophotometer). The sample was obtained by cutting the measurement object (e.g., resin film) so that the width and height of the sample were 10 mm and 10 mm, respectively. The transmission spectrum at each wavelength was measured according to the equipment manual. The sample was placed on the straight line between the measurement beam and the detector of the spectrophotometer, and the transmission spectrum was confirmed by setting the incident angle of the measurement beam to 0°. The incident angle of 0° is a direction substantially parallel to the normal direction of the sample surface.

[0157] The average transmittance in a specific wavelength range in the transmission spectrum is the result of measuring the transmittance at each wavelength while increasing the wavelength by 1 nm starting from the shortest wavelength in the wavelength range, and then calculating the arithmetic mean of the measured transmittances. The maximum transmittance is the highest transmittance among the transmittances measured while increasing the wavelength by 1 nm, and the minimum transmittance is the lowest transmittance among the transmittances measured while increasing the wavelength by 1 nm. For example, the average transmittance in the wavelength range of 350 nm to 360 nm is the arithmetic mean of the transmittances measured at 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 in the wavelength range of 350 nm to 360 nm is the highest transmittance among the transmittances measured at 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 minimum transmittance in the wavelength range of 350 nm to 360 nm is the lowest transmittance among the transmittances measured at 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.

[0158] 3. Pyrolysis temperature (Td 5%) analysis

[0159] Thermogravimetric analysis (TGA) of the compound was performed using a Scinco TGA N-1000 device. Analysis was performed using approximately 3 mg of the sample (compound), 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 value at 95% weight loss (Td 5%) was used as the Td decomposition temperature.

[0160] 4. Mass analysis (MALDI-TOF)

[0161] The mass analysis of the compound was performed using a MALDI-TOF Voyager DE-STR device (Applied Biosystems, USA). It was measured in positive mode in reflector mode and analyzed using anthralin matrix.

[0162] 5. Deuterium substitution rate

[0163] The deuterium substitution rate of the compound was measured by hydrogen nuclear magnetic resonance ( 1 H NMR) analysis. H-NMR analysis was performed on the deuterium-substituted compound (sample compound) and the compound having the same structure before deuterium substitution (reference compound). 1 The position and area of the hydrogen peaks of the reference compound were confirmed by 1 H-NMR analysis of the reference compound, and the positions and areas of the non-deuterium hydrogen peaks and deuterium peaks of the sample compound were confirmed by 1 H-NMR analysis of the sample compound. The deuterium substitution rate was confirmed by comparing the positions and areas of the peaks.

[0164] The substitution rate was calculated using Equation A.

[0165] [Equation A]

[0166] Substitution rate = 100 × D / H

[0167] In Equation A, D is the integral value of the deuterium peak in the 1 H-NMR analysis of the sample compound. H is the integral value of the hydrogen peak in the 1 H-NMR analysis of the reference compound.

[0168] Meanwhile, H-NMR analysis was performed using JEOL's JNM-ECX400 by dissolving in CDCl3 containing TMS. The chemical shift was expressed in ppm. 1 H-NMR analysis. The chemical shift was expressed in ppm.

[0169] Embodiment 1

[0170] Compound A of the following formula A was synthesized in the following manner.

[0171] [Formula A]

[0172]

[0173] In Formula A, D is hydrogen or deuterium, and at least one of the Ds is deuterium. In a three-necked flask equipped with a reflux device, N,N,N,N-tetra(p-diisobutylaminophenyl)-p-phenylenediammonium-d20 (Compound A1) was prepared by deuterium substitution of N,N,N,N-tetra(p-diisobutylaminophenyl)-p-phenylenediamine (Compound D of Formula D in Comparative Example 1).

[0174] The deuterium-substituted compound A1 was synthesized as follows. 9.21 g of the compound D of Comparative Example 1, 0.54 g of silver carbonate (Ag2CO3), and 1.34 g of cyclohexyldiphenylphosphine were added to a three-necked flask equipped with a reflux device. Then, 1 mL of toluene and an excess of deuterium oxide were added, and the mixture was stirred at about 120 °C for 24 hours. 15 mL of dichloromethane and 15 mL of water were added to the flask, and the mixture was stirred and mixed for 30 minutes. The dichloromethane layer was separated from the mixture using a separatory funnel, and methanol was added to precipitate the target compound (compound A1) by recrystallization.

[0175] 0.5 g of compound A1, 0.7 g of lithium bis(trifluoromethanesulfonyl)imide, and 5 mL of dichloromethane were added to a three-necked flask and stirred. Then, 0.7 g of nitric acid and 1 mL of water were further added, and the mixture was stirred at room temperature (25 °C) for 2 hours. After stirring, additional dichloromethane and water were added to the flask, the dichloromethane layer was separated using a separatory funnel, and methanol was added to obtain the target compound (N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediammonium bis(trifluoromethanesulfonyl)imide-d20) (compound A of formula A) (MALDI-TOF m / z 1481.5 [M+H] + ).

[0176] The deuterium substitution rate of the target compound A was approximately 92%.

[0177] Embodiment 2

[0178] The following compound B of formula B was synthesized in the following manner.

[0179] [Formula B]

[0180]

[0181] In formula B, D is hydrogen or deuterium, but at least one of D is deuterium. 1-Iodo-4-nitrobenzene is deuterium-substituted. The deuterium substitution was carried out according to the deuterium substitution method of compound A1 in Embodiment 1, but the deuterium substitution was carried out by using 2.49 g of 1-iodo-4-nitrobenzene instead of using 9.21 g of the compound D of Comparative Example 1.

[0182] Add 2.0 g of deuterium-substituted 1-iodo-4-nitrobenzene, 0.2 g of 1,4-phenylenediamine, 0.04 g of copper powder, and 0.59 g of potassium carbonate into a three-necked flask, and add dimethylformamide (DMF) as a solvent. After adding the solvent, carry out the reaction under reflux at room temperature (25 °C) for about 12 hours. Remove the copper powder and potassium carbonate through a filter to obtain N,N,N,N-tetrakis(4-nitrophenyl)-1,4-phenylenediamine. Add 1.5 g of N,N,N,N-tetrakis(4-nitrophenyl)-1,4-phenylenediamine and 0.5 g of stannous chloride into the three-necked flask, further add 10 mL of HCl as a solvent, and then carry out the reaction at room temperature (25 °C). After the reaction is fully carried out, add 5 mL of methanol to the reaction solution to obtain N,N,N,N-tetrakis(4-aminophenyl)-1,4-phenylenediamine.

[0183] Add 1 g of N,N,N,N-tetrakis(4-aminophenyl)-1,4-phenylenediamine, 4 g of isobutyl bromide, and 0.6 g of potassium carbonate into a three-necked flask, and add DMF as a solvent. Then, carry out the reaction under reflux at room temperature (25 °C) for about 9 hours. After the reaction is completed, remove the potassium carbonate through a filter, place the reaction solution in a separatory funnel, add 10 mL of dichloromethane and 10 mL of water, and then separate the dichloromethane layer. Add methanol to the separated dichloromethane layer to obtain N,N,N,N-tetrakis(p-diisobutylaminophenyl)-1,4-phenylenediamine.

[0184] Add 1 g of N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediamine, 1.4 g of lithium bis(trifluoromethanesulfonyl)imide, and 20 mL of dichloromethane into a three-necked flask, and then stir. Further add 0.14 g of nitric acid and 2 mL of water, and stir the mixture for another 2 hours to react. After the reaction, add additional dichloromethane and water to the flask, separate the dichloromethane layer by using a separatory funnel, and add methanol to obtain bis(trifluoromethanesulfonyl)imide N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediammonium-d16 (Compound B of Formula B) (MALDI-TOF m / z 1496.2 [M+H] + )

[0185] The deuterium substitution rate of Compound B is about 74%.

[0186] Embodiment 3

[0187] Synthesize the following Compound C of Formula C in the following manner.

[0188] [Formula C]

[0189]

[0190] In formula C, D is hydrogen or deuterium, and at least one of the Ds is deuterium. First, deuterium-substituted 1,4-benzenediamine was synthesized. The deuterium substitution was carried out according to the deuterium substitution method of compound A1 in Embodiment 1, but the deuterium substitution was carried out by using 1 g of 1,4-benzenediamine instead of using 9.21 g of compound D in Comparative Example 1.

[0191] 2.0 g of 1-iodo-4-nitrobenzene, 0.2 g of 1,4-benzenediamine with long-term deuterium substitution, 0.04 g of copper powder, and 0.59 g of potassium carbonate were added to a three-necked flask, dimethylformamide (DMF) was added as a solvent, and then the reaction was carried out under reflux conditions at room temperature (25 °C) for about 12 hours. The copper powder and potassium carbonate were removed by filtration to obtain N,N,N,N-tetrakis(4-nitrophenyl)-1,4-benzenediamine. 1.5 g of N,N,N,N-tetrakis(4-nitrophenyl)-1,4-benzenediamine and 0.5 g of stannous chloride were added to the three-necked flask, 10 mL of HCl was further added as a solvent, and then the reaction was carried out at room temperature (25 °C). After the reaction was sufficiently carried out, 5 mL of methanol was added to the reaction solution to obtain N,N,N,N-tetrakis(4-aminophenyl)-1,4-benzenediamine.

[0192] 1 g of N,N,N,N-tetrakis(4-aminophenyl)-1,4-benzenediamine, 4 g of isobutyl bromide, and 0.6 g of potassium carbonate were added to a three-necked flask, and DMF was added as a solvent. Then, the reaction was carried out under reflux conditions at room temperature (25 °C) for about 9 hours. After the reaction was completed, the potassium carbonate was removed by filtration, the reaction solution was placed in a separatory funnel, 10 mL of dichloromethane and 10 mL of water were further added, and then the dichloromethane layer was separated. Methanol was added to the separated dichloromethane layer to obtain N,N,N,N-tetrakis(p-diisobutylaminophenyl)-1,4-benzenediamine.

[0193] 1 g of N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediamine, 1.4 g of lithium bis(trifluoromethanesulfonyl)imide, and 20 mL of dichloromethane were added to a three-necked flask, and then stirred. After stirring, 0.14 g of nitric acid and 2 mL of water were further added, and then the mixture was stirred for another 2 hours to react. After the reaction, dichloromethane and water were additionally added to the flask, the dichloromethane layer was separated by using a separatory funnel, and methanol was added to obtain N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediammonium bis(trifluoromethanesulfonyl)imide-d4 (compound C of formula C) (MALDI-TOF m / z 1485.2 [M+H] + )

[0194] The deuterium substitution rate of compound C was about 17%.

[0195] Comparative Example 1

[0196] The compound D of the following formula D was synthesized in the following manner.

[0197] [Formula D]

[0198]

[0199] 2.0 g of 1-iodo-4-nitrobenzene, 0.2 g of 1,4-phenylenediamine, 0.04 g of copper powder and 0.59 g of potassium carbonate were added to a three-necked flask, and dimethylformamide (DMF) was added as a solvent, and then the reaction was carried out under reflux at room temperature (25 °C) for about 12 hours. The copper powder and potassium carbonate were removed by filtration to obtain N,N,N,N-tetrakis(4-nitrophenyl)-1,4-phenylenediamine. 1.5 g of N,N,N,N-tetrakis(4-nitrophenyl)-1,4-phenylenediamine and 0.5 g of tin chloride were added to a three-necked flask, and 10 mL of HCl was added as a solvent, and the reaction was carried out at room temperature (25 °C). After the reaction was carried out sufficiently, 5 mL of methanol was added to the reaction solution to obtain N,N,N,N-tetrakis(4-aminophenyl)-1,4-phenylenediamine.

[0200] 1 g of N,N,N,N-tetrakis(4-aminophenyl)-1,4-phenylenediamine, 4 g of isobutyl bromide and 0.6 g of potassium carbonate were added to a three-necked flask, and then DMF was added as a solvent. Then, the reaction was carried out under reflux at room temperature (25 °C) for about 9 hours. After the reaction was completed, potassium carbonate was removed by filtration, the reaction solution was placed in a separatory funnel, 10 mL of dichloromethane and 10 mL of water were added, and then the dichloromethane layer was separated. Methanol was added to the separated dichloromethane layer to obtain N,N,N,N-tetrakis(p-diisobutylaminophenyl)-1,4-phenylenediamine.

[0201] 1 g of N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediamine, 1.4 g of lithium bis(trifluoromethanesulfonyl)imide and 20 mL of dichloromethane were added to a three-necked flask, and then stirred. Then, 0.14 g of nitric acid and 2 mL of water were further added, and the mixture was stirred for another 2 hours to react. After the reaction, dichloromethane and water were additionally added to the flask, the dichloromethane layer was separated using a separatory funnel, and methanol was added to obtain N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediammonium (Compound D of formula D) (MALDI-TOF m / z 1481.5 [M+H] + )

[0202] The deuterium substitution rate of Comparative Example 1 was about 0%.

[0203] Table 1 summarizes the absorption capacities of each compound in Examples 1 to 3 and Comparative Example 1. In Table 1, T% (λ max) is the transmittance at each maximum absorption wavelength. Td 5% in Table 1 is the temperature (Td 5%) at which 95% weight loss of the compound occurs in thermogravimetric analysis (TGA).

[0204] [Table 1]

[0205] Maximum absorption wavelength (nm) <![CDATA[T%(λ max )]]> Td5% (°C) Embodiment 1 1,100 39.2 300 Embodiment 2 1,100 39.2 294 Embodiment 3 1,100 39.5 289 Comparative Example 1 1,100 40.0 286

[0206] As can be confirmed from Table 1, each compound of Embodiments 1 to 3 exhibits excellent heat resistance while showing light absorption characteristics comparable to those of Comparative Example 1.

[0207] Test Example 1

[0208] A coating solution was prepared by mixing a cycloolefin resin (TOPAS, 5013F-04), a compound, and a solvent (cyclohexanone). The compound synthesized in the embodiment or comparative example was used as the compound. The mixing ratio of the cycloolefin-based resin, the compound, and the solvent was approximately 69.3:0.99:29.7 (weight ratio of cycloolefin-based resin: compound: solvent). The coating solution was coated on a transparent substrate (a glass substrate manufactured by SCHOTT Co., Ltd.) and kept at 140 °C for about 2 hours to form a resin film with a thickness of about 6 μm.

[0209] The following Table 2 summarizes the transmittance of the resin film before and after reliability evaluation in the visible and infrared regions. The reliability evaluation refers to the evaluation of keeping the resin film at 85 °C and 85% relative humidity for 120 hours. In Table 2, "B" refers to the result before the reliability evaluation, and "A" refers to the result after the reliability evaluation. In addition, in Table 2, Λ max is the transmittance at the absorption maximum (1,100 nm).

[0210] In Table 2, Δ is the change rate (%) of each property before and after the reliability evaluation, which is the result calculated by 100×(A - B) / B, where A is the value represented by A in Table 2 and B is the value represented by B in Table 2. In Table 2, T is the transmittance at the corresponding wavelength, T min is the minimum transmittance within the corresponding wavelength range, and T ave is the average transmittance within the corresponding wavelength range.

[0211] [Table 2]

[0212]

[0213]

[0214] Test Example 2

[0215] Figures 4 to 7The evaluation results of the resin films prepared in the manner of Test Example 1 using the compounds of Embodiments 1 to 3 and Comparative Example 1 are shown respectively. In Figures 4 to 7 , the horizontal axis represents the wavelength (nm), and the vertical axis represents the transmittance (%). In addition, the results disclosed as "before reliability test" are the results just after manufacturing the resin film but before placing the resin under high temperature and high humidity conditions, and the results disclosed as "after reliability test" are the results after performing a reliability evaluation (under the same conditions as Test Example 1) on the resin film after placing the resin film under high temperature and high humidity conditions.

[0216] Referring to Figures 4 to 7 , for the resin films using the compounds of the embodiments, the light absorption characteristics hardly changed before and after the high temperature and high humidity conditions. In contrast, it was confirmed that for the resin films using the compounds of the comparative example, very large changes occurred in the light absorption characteristics before and after the high temperature and high humidity conditions, and thus, the light absorption characteristics were almost lost.

[0217] The following Table 3 summarizes the Figures 4 to 7 main content. In Table 3, A f is the transmittance at the maximum absorption wavelength of the resin film maintained at 85 °C for 120 hours at 85% relative humidity, λ f is the maximum absorption wavelength at this time, and A i is the transmittance at the maximum absorption wavelength of the resin film before being maintained at 85 °C for 120 hours at 85% relative humidity, and λ i is the maximum absorption wavelength at this time.

[0218] In Table 3, △A is a value calculated as 100×(A f -A i ) / A i , and △λ is a value calculated as 100×(λ f -λ i ) / λ i .

[0219] [Table 3]

[0220] Embodiment 1 Embodiment 2 Embodiment 3 Comparative Example 1 <![CDATA[A i > 39.2% 39.20% 39.5% 40.0% <![CDATA[A f > 42.5% 51.4% 67.9% 84.50% △A 8.4 31.1 71.9 111.3 <![CDATA[λ i > 1,100 nm 1,100 nm 1,100 nm 1,100 nm <![CDATA[λ f > 1,100 nm 1,100 nm 1,100 nm 1,100 nm △λ 0% 0% 0% 0%

[0221] Comparing the results of Tables 1 to 3 and Figures 4 to 7 , the compounds of the embodiments and the comparative examples have spectral characteristics similar to those of the compounds themselves, but it can be confirmed that there are significant differences in the absorption characteristics when applied to the resin film and / or the absorption characteristics after evaluation under high temperature and high humidity. From this, it can be confirmed that due to its unique structure, the compound can absorb light in the infrared region. In addition, the compound can effectively form a resin film with excellent performance because it also has excellent heat resistance at the same time.

Claims

1. A compound represented by Formula 1: [Formula 1] in R1 to R 28 are each independently hydrogen, deuterium, alkyl, alkenyl, alkynyl, alkoxy, aryl, aryloxy, arylamino, alkylamino, heteroaryl, alkylsilyl, arylsilyl, amino, nitro, nitrile, hydroxyl or cyano; and R1 to R 28 At least one of them is deuterium.

2. The compound according to claim 1, wherein the deuterium substitution rate of the compound is 10% or more. 3 . The compound according to claim 1 , wherein the compound exhibits maximum absorption in a wavelength range of 690 nm to 1,200 nm. The compound according to claim 3 , wherein the transmittance of the compound at the maximum absorption is 50% or less. The compound according to claim 1 , wherein the compound has a molar mass of 900 g / mol to 3,000 g / mol.

6. The compound of claim 1, wherein the compound has a 5% pyrolysis temperature of at least 285°C. 7 . An ionic compound comprising the compound according to claim 1 ; and an anion.

8. A composition comprising: a resin component; and The compound according to claim 1.

9. The composition according to claim 8, wherein the resin component comprises at least one or more selected from the group consisting of cycloolefin resins, polyarylate resins, polyester 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. 10 . The composition according to claim 8 , wherein the compound is contained in an amount of 0.001 to 10 parts by weight relative to 100 parts by weight of the resin component.

11. A resin film, comprising: a resin component; and The compound according to claim 1.

12. The resin film according to claim 11, wherein the resin component includes at least one or more selected from the group consisting of cycloolefin resins, polyarylate resins, polyester 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. 13 . The resin film according to claim 11 , wherein the resin component comprises a cycloolefin resin. 14 . The resin film according to claim 11 , wherein the resin film exhibits maximum absorption in a wavelength range of 690 nm to 1,200 nm.

15. The resin film according to claim 11, wherein an absolute value of ΔA of the following equation 1 is 80% or less: [Equation 1] △A=100×(A f -A i ) / A i Among them A f is the transmittance of the resin film at the maximum absorption wavelength of the resin film after the resin film is maintained at 85° C. and 85% relative humidity for 120 hours, and A i It is the transmittance of the resin film at the maximum absorption wavelength of the resin film before the resin film is kept at 85° C. and 85% relative humidity for 120 hours.

16. The resin film according to claim 11, wherein an absolute value of Δλ of the following Equation 2 is 10% or less: [Equation 2] △λ=100×(λ f -l i ) / min i in λ f is the maximum absorption wavelength of the resin film after the resin film is kept at 85° C. and 85% relative humidity for 120 hours, and λ i It is the maximum absorption wavelength of the resin film before the resin film is kept at 85° C. and 85% relative humidity for 120 hours. 17 . The resin film according to claim 15 , wherein the maximum absorption wavelength of the resin film exists in a wavelength range of 690 nm to 1,200 nm.

18. An optical filter, comprising: substrate; and The resin film according to claim 11 is formed on one side or both sides of the substrate.

19. An image capturing device comprising the filter according to claim 18. 20 . An infrared sensor comprising the resin film according to claim 11 .

Citation Information

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