compound

Abstract

To provide a compound having superior heat resistance and capable of stably maintaining optical absorption characteristics even when high temperature conditions or high temperature and high humidity conditions are maintained, further provide a resin film in which desired optical properties are secured by applying the compound, and further provide uses of the compound.SOLUTION: The present invention provides a compound represented by the following structural formula. In the formula, R1 to R28 each independently represent hydrogen, deuterium, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryl group, an aryloxy group, an arylamino group, an alkylamino group, a heteroaryl group, an alkylsilyl group, or an arylsilyl group or the like. At least one of R1 to R28 is deuterium.SELECTED DRAWING: None

Description

[Technical Field]

[0001] This specification discloses compounds and their uses. [Background technology]

[0002] Compounds that can be used as absorbers, for example compounds that can absorb light in the infrared region, may be applied in a variety of applications.

[0003] For example, imaging devices (also called solid-state imaging devices) and infrared sensors that use CCD (Charge-Coupled Device) or CMOS (Complementary Metal-Oxide-Semiconductor) image sensors contain silicon photodiodes that are sensitive to the near-infrared region, so absorbents may be used.

[0004] Known examples of absorbents include phthalocyanine-based, cyanine-based, metal dithiol complex-based, squarylium-based, and diimonium salt-based compounds.

[0005] Phthalocyanine compounds are known as near-infrared compounds, but they have a problem of high absorption in the visible light region. Furthermore, cyanine compounds have a problem of having to be used in combination with other compounds because the near-infrared region that can be absorbed by a single compound is narrow. Furthermore, metal dithiol complex compounds have a problem of low solubility, which requires additional dispersion equipment when applied to films, making them difficult to use in applications requiring high transmittance.

[0006] In addition, squarylium compounds are known to have excellent heat resistance. However, squarylium compounds have difficulty absorbing light in the long wavelength region of 900 nm or more. In addition, iminium or diimonium compounds are known to be compounds capable of absorbing light having a wavelength of 900 nm or more. However, iminium or diimonium compounds have a problem in that they lose their light absorption properties in high temperature and / or high humidity environments due to their low thermal stability. Summary of the Invention [Problem to be solved by the invention]

[0007] This specification discloses compounds and their uses.

[0008] The present specification aims to disclose a compound that has excellent heat resistance and can stably maintain its absorption characteristics even under high temperature conditions or high temperature and high humidity conditions. Another object of the present specification is to ensure desired optical characteristics by applying the compound. Another object of the present specification is to disclose uses of the compound. [Means for solving the problem]

[0009] Of the physical properties mentioned in this specification, those whose results are affected by the measurement temperature are the results measured at room temperature unless otherwise specified.

[0010] The term "room temperature" refers to a natural temperature that has not been artificially heated or cooled, and means, for example, any temperature within the range of 10°C to 30°C, or a temperature of about 23°C or about 25°C.

[0011] Unless otherwise specified herein, temperatures are in °C.

[0012] In the present specification, when pressure affects the physical properties, the physical properties are measured at atmospheric pressure unless otherwise specified. The term "atmospheric pressure" refers to natural pressure that is not artificially increased or decreased, and generally refers to a pressure in the range of approximately 700 mmHg to 800 mmHg.

[0013] When a physical property referred to in this specification is affected by humidity, the property is measured at standard humidity unless otherwise specified. Standard humidity refers to a relative humidity of 40% to 60%, for example, a relative humidity of about 40% or 60%.

[0014] When an optical property (for example, refractive index) referred to in this specification is a property that varies with wavelength, the optical property in question is a property for light with a wavelength of 520 nm, unless otherwise specified.

[0015] In this specification, unless otherwise specified, the terms transmittance and absorptance refer to the actual transmittance (measured transmittance) or actual absorptance (measured absorptance) confirmed at a specific wavelength or within a predetermined wavelength range, and are transmittance or absorptance based on an incident angle of 0 degrees.

[0016] Unless otherwise specified, the term "average transmittance" or "average absorbance" refers to the result of measuring the transmittance or absorbance at each wavelength in a given wavelength range, increasing the wavelength by 1 nm from the shortest wavelength, and then calculating the arithmetic mean of the measured transmittance or absorbance. For example, the average transmittance or average absorbance within the wavelength range of 350 nm to 360 nm is 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.

[0017] The term "maximum transmittance" or "maximum absorptance" refers to the maximum transmittance or maximum absorptance measured at wavelengths increasing in 1 nm increments from the shortest wavelength within a given wavelength range. For example, the maximum transmittance or maximum absorptance within a wavelength range of 350 nm to 360 nm is the highest transmittance or absorptance 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.

[0018] The term "minimum transmittance" or "minimum absorptance" refers to the minimum transmittance or minimum absorptance measured at wavelengths increasing in 1 nm increments from the shortest wavelength within a given wavelength range. For example, the minimum transmittance or minimum absorptance within the wavelength range of 350 nm to 360 nm is the lowest transmittance or absorptance 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.

[0019] In this specification, the term "incident angle" refers to an angle relative to the normal to the surface of the object to be evaluated. For example, the transmittance of an optical filter at an incident angle of 0 degrees refers to the transmittance of light incident in a direction substantially parallel to the normal to the surface of the optical filter. This definition of the incident angle also applies to other properties such as transmittance and absorptance.

[0020] As used herein, the term "alkyl group" refers to an alkyl group having 1 to 30, 1 to 24, 1 to 20, 1 to 16, 1 to 12, 1 to 8, or 1 to 4 carbon atoms. The alkyl group may be linear, branched, or cyclic. The alkyl group may be optionally substituted with at least one substituent. Unless otherwise specified, this applies to all alkyl groups referred to in this specification.

[0021] As used herein, the term "alkenyl group" refers to an alkenyl group having 2 to 30, 2 to 24, 2 to 20, 2 to 16, 2 to 12, 2 to 8, or 2 to 4 carbon atoms. The alkenyl group may be linear, branched, or cyclic. The alkenyl group may be optionally substituted with at least one substituent. Unless otherwise specified, the above applies to all alkenyl groups referred to in this specification.

[0022] As used herein, the term "alkynyl group" refers to an alkynyl group having 2 to 20, 2 to 16, 2 to 12, 2 to 8, or 2 to 4 carbon atoms. The alkynyl group may be linear, branched, or cyclic. The alkynyl group may be optionally substituted with at least one substituent. Unless otherwise specified, this applies to all alkynyl groups referred to in this specification.

[0023] As used herein, the term "alkoxy group" refers to an alkoxy group having 1 to 30, 1 to 24, 1 to 20, 1 to 16, 1 to 12, 1 to 8, or 1 to 4 carbon atoms. The alkoxy group may be linear, branched, or cyclic. The alkoxy group may be optionally substituted with at least one substituent. Unless otherwise specified, this applies to all alkoxy groups referred to in this specification.

[0024] As used herein, the term "aryl group" refers to a monovalent residue derived from an aromatic hydrocarbon, and the aryl group may be an aryl group having 6 to 48, 6 to 42, 6 to 36, 6 to 30, 6 to 24, 6 to 18, or 6 to 12 carbon atoms, such as a phenyl group, a tolyl group, a xylyl group, or a naphthyl group. The aryl group may also be optionally substituted with at least one substituent. Unless otherwise specified, this applies to all aryl groups referred to in this specification.

[0025] In addition, the aryl group in this specification may be, for example, a heteroaryl group, and the heteroaryl group has a structure containing a heteroatom other than a carbon atom, such as O, N, or S, in the ring structure of the aryl group. The heteroaryl group may also be optionally substituted with at least one substituent. Unless otherwise specified, this applies to all heteroaryl groups mentioned in this specification.

[0026] The present specification discloses a compound. The compound may be an absorber. The term absorber refers to a compound that can absorb light in any wavelength range.

[0027] The compound may be a compound represented by the following formula 1.

[0028] [ka] 1

[0029] In Chemical Formula 1, R1 to R 28 may each independently be hydrogen, deuterium, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryl group, an aryloxy group, an arylamino group, an alkylamino group, a heteroaryl group, a silyl group, an amino group, a nitro group, a nitrile group, a hydroxy group, or a cyano group.

[0030] The silyl group may be a silyl group in which at least one alkyl group is bonded to silicon (an alkylsilyl group) or a silyl group in which at least one aryl group is bonded to silicon (an arylsilyl group).

[0031] In Chemical Formula 1, the alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, aryloxy group, arylamino group, alkylamino group, heteroaryl group, alkylsilyl group, or arylsilyl group may be optionally substituted with at least one substituent, such as deuterium, boron, halogen, hydroxy group, nitro group, phosphoryl group, alkyl group, alkenyl group, alkynyl group, heteroalkyl group, aryl group, arylalkyl group, heteroaryl group, heteroarylalkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, alkylsilyl group, arylsilyl group, and aryloxy group, but is not limited thereto.

[0032] More specifically, in Chemical Formula 1, R1 to R20 may be, but is not limited to, hydrogen, deuterium, an alkyl group, an alkenyl group, an alkynyl group, a deuterium-substituted alkyl group, a deuterium-substituted alkenyl group, or a deuterium-substituted alkynyl group, and the substituents may be any of the R to R groups described above. 28 As explained in.

[0033] In addition, in Chemical Formula 1, R1 to R 28 Among these, any pair of substituents (e.g., adjacent substituents) may be bonded to each other to form an aliphatic, aromatic, aliphatic hetero, or aromatic hetero fused ring structure. The pair of adjacent substituents refers to a pair of a substituent and a substituent substituted on an atom directly linked to the atom on which the substituent is substituted, a pair of a substituent and a substituent positioned sterically closest to the substituent, or a pair of a substituent and another substituent substituted on the atom on which the substituent is substituted. 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 are adjacent groups.

[0034] Chemical formula 1 may have a structure including an absorption edge and capable of absorbing light of a desired wavelength. For example, the absorption edge may be a skeleton or structure having a so-called resonance structure and / or a conjugated bond.

[0035] It is known that the absorption of light by compounds, especially organic compounds, is due to the energy difference (ΔE) between the ground state and the excited state, which can also be explained as the energy difference between the HOMO (Highest Unoccupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital).

[0036] Generally, organic absorbers may contain resonance structures and / or conjugated bonds as absorption edges that can exhibit light absorption effects, thereby forming a skeleton that can exhibit desired overall light absorption properties.

[0037] The specific type of the absorption edge or skeleton is not particularly limited. The well-known resonance effect refers to the interaction between a lone electron pair of a molecule and an adjacent π-bond electron pair, and 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 connected via one single bond, and it is known that as the length of such a conjugated bond increases, the energy difference between the HOMO and LUMO decreases, and the absorption band shifts to the longer wavelength side.

[0038] For example, the absorption edge may be a skeleton or structure in which the compound disclosed herein exhibits an absorption maximum in the wavelength range of 690 nm to 1200 nm.

[0039] The compounds disclosed herein exhibit an absorption maximum wavelength within the range of 690 nm to 1200 nm. In other examples, the lower limit of the absorption maximum wavelength may be approximately 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 absorption maximum wavelength may be approximately 1200 nm, 1190 nm, 1180 nm, 1170 nm, 1160 nm, 1150 nm, 1140 nm, 1130 nm, 1120 nm, or 1100 nm. The absorption maximum wavelength may be within a range equal to or greater than any one of the aforementioned lower limits, or may be within a range equal to or greater than any one of the aforementioned lower limits but less than or equal to any one of the aforementioned upper limits.

[0040] 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 Unoccupied Molecular Orbital) and the LUMO (Lowest Unoccupied Molecular Orbital), and the absorption maximum wavelength is determined by such an energy difference. Therefore, the structure of the absorption edge may be determined so that the compound has an absorption maximum wavelength within the aforementioned range.

[0041] The compounds disclosed herein are those in which R1 to R 28 At least one of R to R contains deuterium. 28 At least one of R1 to R2 is deuterium. 28 wherein at least one of is an alkyl group substituted with at least one deuterium, an alkenyl group substituted with at least one deuterium, an alkynyl group substituted with at least one deuterium, an alkoxy group substituted with at least one deuterium, an aryl group substituted with at least one deuterium, an aryloxy group substituted with at least one deuterium, an arylamino group substituted with at least one deuterium, an alkylamino group substituted with at least one deuterium, a heteroaryl group substituted with at least one deuterium, an alkylsilyl group substituted with at least one deuterium, or an arylsilyl group substituted with at least one deuterium.

[0042] The compound represented by Chemical Formula 1 is R1 to R 28 The deuterium contained in the compound can ensure excellent heat resistance without affecting the absorption characteristics of the compound. More specifically, the compound represented by Chemical Formula 1 can be obtained by adding R1 to R 20 The deuterium contained in the material can ensure excellent heat resistance.

[0043] In Chemical Formula 1, R1 to R 28The lower limit of the number of deuterium atoms contained in may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, and the upper limit may 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 number of deuterium atoms may be greater than or exceeding any of the aforementioned lower limits, less than or equal to any of the aforementioned upper limits, or greater than or equal to or exceeding any of the aforementioned lower limits but less than or equal to any of the aforementioned upper limits.

[0044] The deuterium substitution rate of the compound disclosed herein may be equal to or higher than a certain level. The deuterium substitution rate is theoretically the ratio of the number of moles of deuterium after deuterium substitution to the number of moles of all hydrogen contained in 1 mole of the compound before deuterium substitution. The lower limit of the deuterium substitution rate may 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 may 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%. The ratio may be greater than or exceeding any of the lower limits, less than or equal to any of the upper limits, or greater than or exceeding any of the lower limits but less than or equal to any of the upper limits. The deuterium substitution ratio refers to the degree to which hydrogen directly bonded to carbon is replaced with deuterium. A method for measuring the deuterium substitution ratio is described in "5. Deuterium Substitution Ratio" in the Examples section of this specification.

[0045] The compounds disclosed herein can ensure heat resistance by controlling the deuterium substitution rate. The carbon-deuterium bond has lower stretching and bending energy than the carbon-hydrogen bond. Therefore, it is understood that the carbon-deuterium bond can reduce the intramolecular vibrational energy compared to the carbon-hydrogen bond, thereby maintaining the absorption properties and ensuring heat resistance even in high-temperature and high-humidity environments.

[0046] The compound may have a molar mass of an appropriate level, for example, the lower limit of the molar mass may 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 may 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 may be greater than or exceeding any of the lower limits, less than or equal to any of the upper limits, or greater than or equal to any of the lower limits but less than or equal to any of the upper limits.

[0047] The compound may have excellent heat resistance. For example, the 5% thermal decomposition temperature (hereinafter, "Td 5%") of the compound may be within a predetermined range. For example, the lower limit of the Td 5% of the compound may be approximately 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 the Td 5% may be approximately 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. The Td 5% may be within a range equal to or greater than any one of the lower limits mentioned above, or within a range equal to or less than any one of the upper limits mentioned above, or within a range equal to or greater than any one of the lower limits but less than or equal to any one of the upper limits mentioned above.

[0048] The Td 5% is the temperature at which 95% weight loss occurs in the thermogravimetric analysis (TGA) of the compound. The Td 5% is determined through the thermogravimetric analysis (TGA), and the method for the thermogravimetric analysis is described in "3. Thermal decomposition temperature (Td 5%) analysis" in the Examples section of this specification.

[0049] The compound may contain an anion, such as a halogen ion, a hexafluoroantimonate ion (SbF6-), a perchlorate ion, a thiocyanate ion (SCN-), a hexafluorophosphate ion (PF6-), a phosphate ion, a bis(trifluoromethanesulfonyl)imide ion, or a tetrafluoroborate ion (BF 4-), trifluoromethylcarboxylic acid anion, alkylsulfonic acid anion, benzenesulfonic acid anion, toluenesulfonic acid ion, benzenecarboxylic acid anion, alkylcarboxylic acid anion, periodic acid anion, hydrofluoroborate ion, tetraphenylboric acid anion, and the like, but are not limited to these.

[0050] The compounds can be obtained by known organic compound synthesis methods and deuterium substitution methods.

[0051] The structure of Chemical Formula 1 is the structure of an absorbent known as a diimonium salt-based compound. Various methods for preparing diimonium salt-based compounds are known in the art. For example, the compound of Chemical Formula 1 may be prepared by substituting deuterium for a reactant used in the preparation of a known diimonium salt-based absorbent, and then applying this reactant to the synthesis of the diimonium salt-based absorbent. Alternatively, the compound may be prepared by synthesizing a diimonium salt-based absorbent using a known synthesis method, and then substituting at least some or all of the hydrogen atoms in the synthesized absorbent with deuterium.

[0052] The deuterium substitution method is not particularly limited. For example, a method of mixing deuterium in a compound to be substituted with deuterium at an appropriate temperature may be used. The lower limit of the mixing temperature may be, for example, about 90°C, 95°C, 100°C, 105°C, 110°C, 115°C, or 120°C, and the upper limit may 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 may be equal to or greater than any of the lower limits, or may be equal to or greater than any of the upper limits but less than any of the upper limits.

[0053] The mixing time is also not particularly limited and may be adjusted taking into account, for example, the desired substitution rate. For example, the lower limit of the mixing time may be about 3 hours, 6 hours, 9 hours, 12 hours, 15 hours, 18 hours, 21 hours, or 24 hours, and the upper limit may be about 72 hours, 36 hours, or 24 hours. The mixing time may be equal to or greater than any of the lower limits mentioned above, or may be less than or equal to any of the upper limits mentioned above, or may be equal to or greater than any of the lower limits but less than or equal to any of the upper limits mentioned above.

[0054] The mixing may be carried out in the presence of an additional compound that can assist, promote, or initiate the substitution with deuterium. For example, the compound that functions as a catalyst for the substitution with deuterium may be any of silver oxide (AgO), silver acetate (AgOAc), silver trifluoroacetate (CFCOOAg), silver carbonate (AgCO), palladium acetate (Pd(OAc)), palladium chloride (PdCl), bis(acetonatriyl)dichloropalladium (PdCl(CHCN)), tris(dibenzylideneacetone)dipalladium (Pd(dba)), tetrakis(triphenylphosphine)palladium (Pd(PPh)), and bis(dibenzylideneacetone)palladium (Pd(dba)). However, the compound is not limited thereto as long as it functions as a catalyst for the substitution with deuterium. Examples of compounds that function as ligands during deuterium substitution include allyldiphenylphosphine, allyldiphenylphosphine oxide, benzyldiphenylphosphine, 1-[2-[bis(tert-butyl)phosphino]phenyl]-3,5-diphenyl-1H-pyrazole, bis[2-(adamantylphosphino)ethyl]amine, and bis(5H-dibenzo[a,d]cyclohepten-5-yl)phenylphosphine. Bis(5H-dibenzo[a,d]cyclohepten-5-yl)phenylphosphine, Bis(5H-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]-diazaphospholidine 2-oxide 2-oxide), Bis(dimethylamino)chlorophosphine, 2-[Bis(3,5-dimethylphenyl)phosphino]benzaldehyde, 2,2'-Bis(diphenylphosphino)-1,1'-biphenyl, Bis(4-fluorophenyl)phenylphosphine oxide oxide), Bis[4-(3,3,4,4,5,5,5-heptafluoro-2,2-bis(trifluoromethyl)pentyl)phenyl]phenylphosphine, 1,1'-bis(phenylphosphinidene)ferrocene (1,1'-bis(phenylphosphinidene)ferrocene), (2-Bromophenyl)dicyclohexylphosphine, (2-Bromophenyl)diphenylphosphine, tert-butyldicyclohexylphosphine, tert-butyldiisopropylphosphine diisopropylphosphine, tert-butyldiphenylphosphine, di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine, 2-chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphosphoridine isopropylphenyl)-1,3,2-diazaphospholidine), 2-Dicyclohexylphosphino-2',6'-bis(N,N-dimethylamino)biphenyl, 1-(Dicyclohexylphosphino)-2,2-diphenyl-1-methylcyclopropane ane), dicyclohexyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine, cyclohexyldiphenylphosphine, 2-(dicyclohexylphosphino)-1,1-diphenyl-1-propene1-diphenyl-1-propene), Dicyclohexyl(1-methyl-2,2-diphenylvinyl)phosphine, Di(1-adamantyl)-2-dimethylaminophenylphosphine, Di-1-adamantylphosphine, Di(1-adamantyl)-(2-triisopropyl)phosphine Di(1-adamantyl)-(2-triisopropylsiloxyphenyl)phosphine, (5H-Dibenzo[a,d]cyclohepten-5-yl)diphenylphosphine, (R)-(-)-1-[(S)-2-(di(3,5-bis-trifluoromethylphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, (R)-(-)-1-[(S)-2-(d i(3,5-bis-trifluoromethylphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine), (R)-(-)-1-[(S)-2-(di(3,5-bis-trifluoromethylphenyl)phosphino)ferrocenyl]ethyldi(3,5-dimethylphenyl)phosphine lphenyl)phosphine), P,P-Dichloroferrocenylphosphine, (R)-(-)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine, and 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferroceneHowever, the compound may be any of the compounds that function as ligands upon deuterium substitution, and is not limited to these.

[0055] The present specification further discloses compositions comprising said compounds. The term composition refers to a mixture comprising a compound and other components, or a mixture comprising two or more compounds.

[0056] The composition containing such a compound essentially contains the compound of Chemical Formula 1 above, and may further contain other necessary components.

[0057] For example, the composition may further contain a resin component that functions as a binder. In this case, the type of resin component to be applied is not particularly limited, and a known resin component used to form a resin film, for example, a near-infrared resin film, may be applied. In this specification, the compound component may exhibit appropriate compatibility or solubility with the various known resin components.

[0058] Examples of the resin component include at least one of cycloolefin (COP) 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, silicone resins, and various other organic resins or organic-inorganic hybrid resins, but are not limited to these.

[0059] Although not particularly limited, the compound of the present specification may be mixed with a cyclic olefin resin, which is one of the known resin components that function as binders, to form a resin film that exhibits excellent performance. Thus, in one example, the resin component may be a cyclic olefin resin.

[0060] When a resin component is used, its proportion is not particularly limited. For example, the resin component may be present so that the weight proportion of the compound relative to 100 parts by weight of the resin component is in the range of 0.001 to 10 parts by weight. In other examples, the lower limit of the weight proportion of the compound relative to 100 parts by weight of the resin component may be approximately 0.001 parts by weight, 0.005 parts by weight, 0.01 parts by weight, 0.05 parts by weight, 0.1 parts by weight, 0.5 parts 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 may be approximately 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 ratio may be greater than or equal to any of the aforementioned lower limits, or less than or equal to any of the aforementioned upper limits, or greater than or equal to any of the aforementioned lower limits but less than or equal to any of the aforementioned upper limits.

[0061] For example, the composition may further contain a solvent in which the compound and / or the resin component is dispersed. In this case, the type of solvent to be used is not particularly limited, and any known solvent used to form a resin film, for example, a near-infrared resin film, may be used. In this specification, the compound component may exhibit appropriate compatibility or solubility in various known solvents.

[0062] 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, pyridone, chloroform, 1,4-dioxane, ortho-dichlorobenzene, chlorobenzene, aliphatic alcohols having two or more carbon atoms (e.g., isobutyl alcohol, isopropyl alcohol, ethanol, isopropanol, butanol, etc.), butyl acetate, tetrahydrofuran, or xylene.

[0063] When a solvent is used, the ratio thereof is not particularly limited, and the ratio may be adjusted within a range that allows appropriate dispersion of the compound and / or resin component.

[0064] The composition may contain other optional components in addition to the above-mentioned components, such as, but not limited to, 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.

[0065] The present specification further relates to uses of said compounds or said compositions.

[0066] For example, the present specification may relate to a resin film to which the compound or composition is applied.

[0067] Such a resin film may contain at least a resin component and the compound.

[0068] In this case, the specific type of resin component and the ratio of the resin component to the compound are as described in the section on the compound composition.

[0069] The resin film may be a film capable of absorbing light within a predetermined wavelength range. In one example, the resin film may be an infrared resin film or a near-infrared resin film. Such a resin film may exhibit absorption characteristics in at least a part of a wavelength range, for example, within a wavelength range of approximately 690 nm to 1200 nm.

[0070] For example, the resin film may exhibit a maximum absorption wavelength in the range of 690 nm to 1200 nm. In other examples, the lower limit of the maximum absorption wavelength may be approximately 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. Furthermore, the upper limit of the maximum absorption wavelength may be approximately 1200 nm, 1190 nm, 1180 nm, 1170 nm, 1160 nm, 1150 nm, 1140 nm, 1130 nm, 1120 nm, or 1100 nm. The absorption maximum wavelength may be within a range equal to or greater than any one of the aforementioned lower limits, or within a range equal to or less than any one of the aforementioned upper limits, or within a range equal to or greater than any one of the aforementioned lower limits but less than or equal to any one of the aforementioned upper limits.

[0071] Due to these properties, the resin film may be applied to various devices such as optical filters and infrared sensors, and may have excellent optical properties and physical properties such as excellent heat resistance.

[0072] For example, the transmittance at the absorption maximum of the resin film may be equal to or less than a certain level. The upper limit may be approximately 50%, 49%, 48%, 47%, 46%, 45%, 44%, 43%, 42%, 41%, or 40%, and the lower limit may be approximately 0.1%, 1%, 10%, 15%, 20%, 25%, 30%, 35%, or 39%. The transmittance at the absorption maximum may be equal to or greater than any of the lower limits, or may be less than or equal to any of the upper limits, or may be equal to or greater than any of the lower limits but less than or equal to any of the upper limits.

[0073] For example, the resin film is maintained at 85°C and 85% relative humidity for 120 hours, and the transmittance at the absorption maximum wavelength of the resin film is A f The transmittance at the absorption maximum wavelength of the resin film before being kept at 85°C and 85% relative humidity for 120 hours is A i When A f -A i The upper limit of the absolute value of A may be about 40%, 35%, 30%, 25%, 20%, 15%, 10%, or 5%, and the lower limit may be about 0%, 5%, 10%, 15%, 20%, or 25%. f -A i The absolute value of may be in a range that is less than or equal to any of the aforementioned upper limits, or greater than or equal to or exceeding any of the aforementioned lower limits while still being less than or equal to any of the aforementioned upper limits.

[0074] For example, the resin film may have an absolute value of ΔA in the following formula 1 that is equal to or less than a predetermined value.

[0075] [Formula 1] ΔA=100×(A f -A i ) / A i

[0076] In Equation 1, A fis the transmittance at the absorption maximum wavelength of the resin film maintained at 85°C and 85% relative humidity for 120 hours, and A i is the transmittance at the absorption maximum wavelength of the resin film before being kept at 85° C. and 85% relative humidity for 120 hours, and the absorption maximum wavelength is within the wavelength range of 690 nm to 1200 nm.

[0077] In Formula 1, the upper limit of the absolute value of ΔA may be about 80%, 70%, 60%, 50%, 45%, 40%, 35%, 30%, 25%, 20%, 15%, or 10%, and the lower limit may 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 may be less than or equal to any of the upper limits, or may be greater than or equal to or exceeding any of the lower limits while still being less than or equal to any of the upper limits.

[0078] In the formula 1, A f The upper limit of A may be about 80%, 75%, 70%, 65%, 60%, 55%, 50%, or 45%, and the lower limit may be about 10%, 20%, 30%, 40%, 50%, 60%, or 65%. f may be in a range that is less than or equal to any of the aforementioned upper limits, or greater than or equal to or exceeding any of the aforementioned lower limits while still being less than or equal to any of the aforementioned upper limits.

[0079] The resin film may have an absolute value of Δλ in the following formula 2 that is equal to or less than a predetermined value.

[0080] [Formula 2] Δλ=100×(λ f -λ i ) / λ i

[0081] In Equation 2, λ fis the absorption maximum wavelength of the resin film maintained 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, and the maximum absorption wavelength is within the wavelength range of 690 nm to 1200 nm.

[0082] In Equation 2, the upper limit of the absolute value of Δλ may be about 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1%, or 0.5%, and the lower limit may be 0%. The absolute value of Δλ may be within a range that is less than or equal to any of the upper limits, or may be greater than or equal to any of the lower limits but is less than or equal to any of the upper limits.

[0083] In the above formula 2, λ f and λ i and may each be in the range of 690 nm to 1200 nm. f and λ i In other examples, the lower limit of each of the λ may 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. f and λ i The upper limit of each of the λ may be about 1200 nm, 1190 nm, 1180 nm, 1170 nm, 1160 nm, 1150 nm, 1140 nm, 1130 nm, 1120 nm, or 1100 nm. f and λ i may be in a range equal to or greater than any one of the aforementioned lower limits, or in a range equal to or less than any one of the aforementioned upper limits, or in a range equal to or greater than any one of the aforementioned lower limits but less than or equal to any one of the aforementioned upper limits.

[0084] Due to its absorption properties, the resin film can be applied to various devices such as optical filters and infrared sensors to efficiently achieve desired properties.

[0085] In the present specification, the resin film may be formed by a known method as long as the compound or composition of the present application is used. For example, the resin film may be formed by coating the compound composition by an appropriate method and, if necessary, performing a curing or drying process.

[0086] The thickness of the resin film is not particularly limited, and may be adjusted in consideration of the desired properties. In one example, the resin film may have a thickness in the range of about 0.5 to 20 μm.

[0087] The present specification further relates to an optical filter, which may include a base layer and the resin film formed on one or both sides of the base layer.

[0088] FIG. 1 shows an example of the optical filter in which the resin film 200 is formed on one surface of a base layer 100. In FIG.

[0089] The optical filter of the present application may exhibit excellent performance by including the resin film described above. For example, the optical filter may realize a visible light transmission band with high transmittance while efficiently and accurately blocking unwanted infrared light.

[0090] There is no particular limitation on the type of transparent substrate applied to the optical filter, and known transparent substrates for optical filters may be used.

[0091] In one example, the base layer may be a so-called near-infrared absorbing substrate. A near-infrared absorbing substrate is a substrate that exhibits absorption characteristics in at least a portion of the near-infrared region. So-called blue glass, which exhibits this characteristic by containing copper, is a typical example of the near-infrared absorbing substrate. Such near-infrared absorbing substrates are useful for constructing optical filters that block light in the near-infrared region, but are disadvantageous in terms of ensuring high transmittance in the visible light region due to their absorption characteristics, and also in terms of durability. In this specification, by selecting a near-infrared absorbing substrate and combining it with a specific resin film, an optical filter can be provided that efficiently blocks desired light, exhibits high transmittance characteristics in the visible light region, and has excellent durability.

[0092] The infrared-absorbing substrate may be a substrate exhibiting a certain level or higher of average transmittance in the range of 425 nm to 560 nm. The lower limit of the average transmittance may be approximately 75%, 77%, 79%, 81%, 83%, 85%, 87%, or 89%, and the upper limit may be approximately 98%, 96%, 94%, 92%, or 90%. The average transmittance may be equal to or greater than any of the lower limits, or may be equal to or greater than any of the lower limits but less than or equal to any of the upper limits.

[0093] The infrared-absorbing substrate may be a substrate exhibiting a maximum transmittance of a certain level or higher in the range of 425 nm to 560 nm. The lower limit of the maximum transmittance may be approximately 80%, 82%, 84%, 86%, 88%, or 90%, and the upper limit may be approximately 100%, 98%, 96%, 94%, 92%, or 90%. The maximum transmittance may be equal to or greater than any of the lower limits, or may be equal to or greater than any of the lower limits but less than or equal to any of the upper limits.

[0094] The infrared-absorbing substrate may be a substrate exhibiting a certain level or higher of average transmittance in the range of 350 nm to 390 nm. The lower limit of the average transmittance may be about 75%, 77%, 79%, 81%, or 83%, and the upper limit may be about 98%, 96%, 94%, 92%, 90%, 88%, 86%, or 84%. The average transmittance may be equal to or greater than any of the lower limits, or may be equal to or greater than any of the lower limits but less than or equal to any of the upper limits.

[0095] The infrared-absorbing substrate may be a substrate exhibiting a maximum transmittance of a certain level or higher in the range of 350 nm to 390 nm. The lower limit of the maximum transmittance may be about 80%, 82%, 84%, 86%, or 87%, and the upper limit may be about 100%, 98%, 96%, 94%, 92%, 90%, or 88%. The maximum transmittance may be equal to or higher than any of the lower limits, or may be equal to or higher than any of the lower limits but lower than or equal to any of the upper limits.

[0096] The infrared-absorbing substrate may have a transmittance at a wavelength of 700 nm within a certain range. The lower limit may be approximately 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, or 28%, and the upper limit may be approximately 45%, 43%, 41%, 39%, 37%, 35%, 33%, 31%, or 29%. The transmittance may be greater than or exceeding any of the lower limits, less than or equal to any of the upper limits, or greater than or exceeding any of the lower limits but less than or equal to any of the upper limits.

[0097] The infrared-absorbing substrate may have a certain range of average transmittance in the wavelength range of 700 nm to 800 nm. The lower limit may be about 5%, 7%, 9%, 11%, 13%, 15%, 15.5%, 16%, or 16.5%, and the upper limit may be about 30%, 28%, 26%, 24%, 22%, 20%, 18%, or 17%. The average transmittance may be equal to or greater than any of the lower limits, or may be less than or equal to any of the upper limits, or may be equal to or greater than any of the lower limits but less than or equal to any of the upper limits.

[0098] The infrared-absorbing substrate may have a maximum transmittance within a certain range in the wavelength range of 700 nm to 800 nm. The lower limit may be approximately 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, or 28%, and the upper limit may be approximately 43%, 41%, 39%, 37%, 35%, 33%, 31%, or 29%. The maximum transmittance may be equal to or greater than any of the lower limits, or may be less than or equal to any of the upper limits, or may be equal to or greater than any of the lower limits but less than or equal to any of the upper limits.

[0099] The infrared-absorbing substrate may have an average transmittance within a certain range in the range of 800 nm to 1000 nm. The lower limit may be about 3%, 5%, 7%, 9%, or 11%, and the upper limit may be about 20%, 18%, 16%, 14%, or 12%. The average transmittance may be equal to or greater than any of the lower limits mentioned above, or may be less than or equal to any of the upper limits mentioned above, or may be equal to or greater than any of the lower limits but less than or equal to any of the upper limits mentioned above.

[0100] The infrared-absorbing substrate may have a maximum transmittance within a certain range in the wavelength range of 800 nm to 1000 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 equal to or greater than any of the lower limits, or may be less than or equal to any of the upper limits, or may be equal to or greater than any of the lower limits but less than or equal to any of the upper limits.

[0101] The infrared-absorbing substrate may have an average transmittance within a certain range in the wavelength range of 1000 nm to 1200 nm. The lower limit may be approximately 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, or 25%, and the upper limit may be approximately 50%, 48%, 46%, 44%, 42%, 40%, 38%, 36%, 34%, 32%, 30%, 28%, or 26%. The average transmittance may be equal to or greater than any of the lower limits, or may be less than or equal to any of the upper limits, or may be equal to or greater than any of the lower limits but less than or equal to any of the upper limits.

[0102] The infrared-absorbing substrate may have a maximum transmittance within a certain range in the wavelength range of 1000 nm to 1200 nm. The lower limit may be approximately 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, or 36%, and the upper limit may be approximately 70%, 68%, 66%, 64%, 62%, 60%, 58%, 56%, 54%, 52%, 50%, 48%, 46%, 44%, 42%, 40%, 38%, or 36%. The maximum transmittance may be greater than or exceeding any of the lower limits, or less than or equal to any of the upper limits, or greater than or exceeding any of the lower limits but less than or equal to any of the upper limits.

[0103] The infrared absorbing substrate may be combined with the resin film of this specification to form a desired optical filter.

[0104] Such a substrate may be a substrate known as infrared absorbing glass. Such glass is an absorbing glass manufactured by adding CuO or the like to a fluorophosphate glass or a phosphate glass. Therefore, in one example, a CuO-containing fluorophosphate glass substrate or a CuO-containing phosphate glass substrate may be used as the infrared absorbing substrate in this specification. Phosphate glass also includes K-phosphate glass, in which part of the glass skeleton is made of SiO2. Such absorbing glass is well known, and for example, the glass disclosed in Korean Patent Registration No. 10-2056613 or other commercially available absorbing glass (e.g., commercially available products from Hoya, Short, PTOT, etc.) may be used.

[0105] Such an infrared-absorbing substrate contains copper. In this specification, a substrate having a copper content in the range of 1% to 7% by weight may be used. In other examples, the copper content may be about 1.5% by weight or more, 2% by weight or more, 2.5% by weight or more, 2.6% by weight or more, 2.7% by weight or more, or 2.8% by weight or more, or about 6.5% by weight or less, 6% by weight or less, 5.5% by weight or less, 5% by weight or less, 4.5% by weight or less, 4% by weight or less, 3.5% by weight or less, 3% by weight or less, or 2.9% by weight or less. Substrates having such copper contents are likely to exhibit the optical properties described above and may be combined with the resin film to form an optical filter with desired properties.

[0106] The copper content can be confirmed using a Wavelength Dispersive X-ray Fluorescence Spectrometry (WD XRF) analyzer. When a sample (substrate layer) is irradiated with X-rays using this analyzer, characteristic secondary X-rays are generated from the individual elements of the sample, and the analyzer detects the secondary X-rays according to the wavelengths of each element. The intensity of the secondary X-rays is proportional to the element content, so quantitative analysis can be performed based on the intensity of the secondary X-rays measured according to the wavelengths of each element.

[0107] The thickness of the infrared absorbing substrate may be adjusted within a range of, for example, about 0.03 mm to 5 mm, but is not limited thereto.

[0108] The optical filter of the present specification may further include other known components necessary in addition to the substrate layer and resin film.

[0109] For example, the optical filter may further include a dielectric film, which may be provided on one or both surfaces of the base layer.

[0110] 2 and 3 are examples of optical filters to which a dielectric film 300 is added, and show cases in which the dielectric film 300 is formed on one or both sides of a laminated structure including a base layer 100 and a resin film 200.

[0111] Such a dielectric film is a film formed by repeatedly stacking a dielectric material with a low refractive index and a dielectric material with a high refractive index, and is used to form a so-called IR reflective layer and an AR (Anti-reflection) layer. In the present application, such a known dielectric film for forming an IR reflective layer or an AR layer may also be applied.

[0112] Therefore, the dielectric film may have a multilayer structure including at least two types of sub-layers having different refractive indices from each other, or may have a multilayer structure in which the two types of sub-layers are repeatedly stacked.

[0113] The material for forming the dielectric film, i.e., the material for forming each of the sub-layers, is not particularly limited, and known materials may be used. Typically, low-refractive-index sub-layers are made of SiO2 or fluorides such as Na5Al3F14, Na3AlF6, or MgF2, and high-refractive-index sub-layers are made of amorphous silicon, TiO2, Ta2O5, Nb2O5, ZnS, or ZnSe, but the materials used in this specification are not limited to these.

[0114] The method for forming the dielectric film is not particularly limited, and may be, for example, a known deposition method. Methods for controlling the reflection or transmission characteristics of the dielectric film by taking into account the deposition thickness and number of sub-layers are known in the art, and in this specification, the dielectric film may be formed by such a known method.

[0115] The optical filter may further include a resin film (hereinafter referred to as an ultraviolet resin film) that exhibits ultraviolet absorption properties as a resin film distinct from the resin film. However, such a resin film is not an essential component, and for example, an ultraviolet compound described below may be incorporated into one resin film together with the compound of Chemical Formula 1.

[0116] In one example, the ultraviolet resin film may be designed to exhibit an absorption maximum in a wavelength range of approximately 300 nm to 390 nm.

[0117] The ultraviolet resin film may contain only an ultraviolet compound, or may contain two or more types of ultraviolet compounds as required.

[0118] For example, as the ultraviolet compound, a known compound that exhibits an absorption maximum in the wavelength region of approximately 300 nm to 390 nm may be applied.

[0119] The material and method for forming such an ultraviolet resin film are not particularly limited, and known materials and methods may be used.

[0120] Typically, the UV resin film is formed using a material in which a UV compound capable of exhibiting a desired absorption maximum is blended with a transparent resin, and the transparent resin may be a resin component applied to the compound composition.

[0121] In addition to the above-mentioned layers, various other necessary optical filters may be added as long as the desired effect is not impaired.

[0122] The present specification further relates to an imaging device including the optical filter. In this case, the configuration of the imaging device and the application of the optical filter are not particularly limited, and known configurations and application methods may be applied.

[0123] Furthermore, the use of the optical filter of this specification is not limited to the imaging device, but may also be applied to various other uses that require blocking of near-infrared rays, such as display devices such as PDPs.

[0124] The present specification further relates to an infrared sensor including the resin film. The configuration of the infrared sensor is not particularly limited as long as it includes the resin film of the present application. For example, the infrared sensor may be configured by introducing the resin film of the present application into a known motion sensor, proximity sensor, or gesture sensor.

[0125] Furthermore, the applications of the compound composition or resin film of the present specification are not limited to the optical filters, infrared sensors and / or imaging devices, but may also be applied to various other applications requiring infrared blocking, such as electrical components for LiDAR and the like. [Effects of the Invention]

[0126] The present specification discloses a compound and uses thereof. The present specification can provide a compound that has excellent heat resistance and can stably maintain its light absorption properties even when high-temperature conditions or high-temperature and high-humidity conditions are maintained. The present specification can further provide a resin film that ensures desired optical properties by applying the compound. The present specification can further provide uses of the compound. [Brief explanation of the drawings]

[0127] [Figure 1] FIG. 1 is a diagram illustrating an exemplary structure of an optical filter of the present application. [Figure 2] FIG. 2 is a diagram illustrating an exemplary structure of an optical filter of the present application. [Figure 3] FIG. 3 is a diagram illustrating an exemplary structure of an optical filter of the present application. [Figure 4] FIG. 4 is a diagram showing the light absorption characteristics of resin films containing the compounds of Examples and Comparative Examples before and after evaluation under high temperature and high humidity conditions. [Figure 5] FIG. 5 is a diagram showing the light absorption characteristics of resin films containing the compounds of Examples and Comparative Examples before and after evaluation under high temperature and humidity conditions. [Figure 6] FIG. 6 is a diagram showing the light absorption characteristics of resin films containing the compounds of Examples and Comparative Examples before and after evaluation under high temperature and high humidity conditions. [Figure 7] FIG. 7 is a diagram showing the light absorption characteristics of resin films containing the compounds of Examples and Comparative Examples before and after evaluation under high temperature and humidity conditions. DETAILED DESCRIPTION OF THE INVENTION

[0128] The compounds disclosed herein will be described in more detail through the following examples and comparative examples, but the scope of the compounds is not limited to the following examples.

[0129] 1. Absorption maximum measurement method The absorption maximum of the compound was evaluated by a conventional method. Specifically, the sample (compound) was dissolved in chloroform for about 10 minutes. -5 After dissolving at a concentration of M, the sample was evaluated using a measuring device (Agilent, Varian Cary 4000).

[0130] 2. Evaluation of transmittance spectrum The transmittance spectrum was measured using a spectrophotometer (PerkinElmer Lambda 750 spectrophotometer) for a specimen obtained by cutting the measurement object (e.g., a resin film) to a width and length of 10 mm. The transmittance spectrum was measured for each wavelength according to the instrument's manual. The specimen was placed on a straight line between the measurement beam and detector of the spectrophotometer, and the transmittance spectrum was measured with the measurement beam at an incident angle of 0 degrees. The incident angle of 0 degrees is a direction substantially parallel to the normal direction of the specimen surface.

[0131] The average transmittance within a given wavelength range in a transmittance spectrum is the result of measuring the transmittance at each wavelength while increasing the wavelength by 1 nm 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 within a 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 within a 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 minimum transmittance within the wavelength range of 350nm to 360nm is the lowest transmittance measured at wavelengths of 350nm, 351nm, 352nm, 353nm, 354nm, 355nm, 356nm, 357nm, 358nm, 359nm, and 360nm.

[0132] 3.Thermal decomposition temperature (Td 5%) analysis Thermogravimetric analysis (TGA) of the compound was carried out using a TGA N-1000 instrument manufactured by Scinco. Approximately 3 mg of sample (compound) was used for the analysis. The temperature range was 25°C to 800°C, the heating rate was 10°C / min, and the heating time was 60 cm. 3 The analysis was carried out under nitrogen (N2) atmosphere at a rate of 1 / min. The Td decomposition temperature was used as the value at 95% weight loss (Td 5%).

[0133] 4.Mass analysis (Maldi-tof) Mass analysis of the compounds was performed using a MALDI TOF Voyager DE-STR instrument (Applied Biosystems, USA) in reflector mode and positive mode, using a dithranol matrix.

[0134] 5. Deuterium substitution rate The deuterium substitution rate of a compound can be measured by hydrogen nuclear magnetic resonance ( 1 The results were measured through H NMR analysis. The deuterium-substituted compound (sample compound) and the compound with the same structure before deuterium substitution (reference compound) were compared. 1 H-NMR analysis was carried out for each of the above-mentioned reference compounds. 1 The position and area of ​​the hydrogen peak of the compound was confirmed by H-NMR analysis, and the sample compound 1 H-NMR analysis was performed to confirm the position and area of ​​the hydrogen peak (not deuterium) and the position and area of ​​the deuterium peak of the compound. The deuterium substitution rate was confirmed by comparing the peak positions and areas.

[0135] The substitution rate was calculated using the following formula A.

[0136] [Formula A] Replacement rate=100×D / H

[0137] In formula A, D is the 1 is the integral value of the deuterium peak in H-NMR analysis, and H is the integral value of the deuterium peak in the reference compound. 1 This is the integral value of the hydrogen peak in H-NMR analysis.

[0138] On the other hand, 1 H-NMR analysis was performed using a JEOL JNM-ECX400 in CDCl3 containing TMS, and chemical shifts were expressed in ppm.

[0139] Example 1 Compound A shown below was synthesized by the following method.

[0140] [ka] Chemical A

[0141] In formula A, D is hydrogen or deuterium, and at least one of D is deuterium.

[0142] N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenedimonium (Compound D of Chemical Formula D in Comparative Example 1) was deuterium-substituted in a three-necked flask equipped with a reflux apparatus to produce N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenedimonium-d20 (Compound A1).

[0143] The deuterium-substituted compound A1 was synthesized as follows: 9.21 g of compound D from Comparative Example 1, 0.54 g of silver carbonate (AgCO), and 1.34 g of cyclohexyldiphenylphosphine were placed in a three-neck flask equipped with a reflux apparatus. Next, 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 for an additional 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) through recrystallization.

[0144] 10.5 g of Compound A, 0.7 g of lithium bistrifluoromethanesulfonylimide, and 5 mL of dichloromethane were added to a three-neck flask and stirred. Then, 0.7 g of silver nitrate and 1 mL of water were added and stirred at room temperature (25 °C) for another 2 hours. After stirring, dichloromethane and water were further added to the flask, and the dichloromethane layer was separated using a separatory funnel. Methanol was added to obtain the target compound (bistrifluoromethanesulfonylimide N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenedimonium-d20) (Compound A of Chemical Formula A) (Maldi-tof m / z 1481.5 [M+H] + ).

[0145] The deuterium substitution rate of the target compound A was about 92%.

[0146] Example 2. Compound B of the following formula B was synthesized by the following method.

[0147] [ka] B

[0148] In formula B, D is hydrogen or deuterium, and at least one of D is deuterium.

[0149] 1-Iodo-4-nitrobenzene was substituted with deuterium by the same method as used for compound A1 in Example 1, except that 2.49 g of 1-iodo-4-nitrobenzene was used instead of 9.21 g of compound D in Comparative Example 1.

[0150] 2.0 g of the 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 were added to a three-neck flask, and dimethylformamide (DMF) was added as a solvent. The mixture was then reacted at room temperature (25°C) and refluxed for approximately 12 hours. The copper powder and potassium carbonate were removed through a filter, yielding N,N,N,N-tetrakis(4-nitrophenyl)-1,4-phenylenediamine. 1.5 g of the N,N,N,N-tetrakis(4-nitrophenyl)-1,4-phenylenediamine and 0.5 g of tin chloride were added to a three-neck flask, and 10 mL of HCl was added as a solvent. The reaction was then carried out at room temperature (25°C). After the reaction was complete, 5 mL of methanol was added to the reaction solution to yield N,N,N,N-tetrakis(4-aminophenyl)-1,4-phenylenediamine.

[0151] 1 g of the N,N,N,N-tetrakis(4-aminophenyl)-1,4-phenylenediamine, 4 g of isobutyl bromide, and 0.6 g of potassium carbonate were placed in a three-neck flask, and DMF was added as a solvent. The reaction was carried out at room temperature (25°C) under reflux conditions for approximately 9 hours. After the reaction was completed, the potassium carbonate was removed through a filter, and the reaction solution was placed in a separatory funnel. 10 mL of dichloromethane and 10 mL of water were added, and 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.

[0152] 1 g of N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediamine, 1.4 g of lithium bistrifluoromethanesulfonylimide, and 20 mL of dichloromethane were added to a three-neck flask and stirred. Then, 0.14 g of silver nitrate and 2 mL of water were added and the mixture was stirred for another 2 hours to react. After the reaction, dichloromethane and water were further added to the flask, and the dichloromethane layer was separated using a separatory funnel. Methanol was added to obtain bistrifluoromethanesulfonylimide N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenedimonium-d16 (compound B of formula B) (Maldi-tof m / z 1496.2 [M+H] + ).

[0153] The deuterium substitution rate of the compound B was about 74%.

[0154] Example 3 Compound C shown below was synthesized by the following method.

[0155] [ka] cation C

[0156] In formula C, D is hydrogen or deuterium, and at least one of D is deuterium.

[0157] First, deuterium-substituted 1,4-phenylenediamine was synthesized by the same method as used for compound A1 in Example 1, except that 1 g of 1,4-phenylenediamine was used instead of 9.21 g of compound D in Comparative Example 1.

[0158] A three-neck flask was charged with 2.0 g of 1-iodo-4-nitrobenzene, 0.2 g of the deuterium-substituted 1,4-phenylenediamine, 0.04 g of copper powder, and 0.59 g of potassium carbonate. Dimethylformamide (DMF) was added as a solvent, and the mixture was allowed to react at room temperature (25°C) under reflux for approximately 12 hours. The copper powder and potassium carbonate were removed through a filter, yielding N,N,N,N-tetrakis(4-nitrophenyl)-1,4-phenylenediamine. 1.5 g of the N,N,N,N-tetrakis(4-nitrophenyl)-1,4-phenylenediamine and 0.5 g of tin chloride were added to the three-neck flask, and 10 mL of HCl was added as a solvent. The reaction was allowed to proceed at room temperature (25°C). After the reaction was complete, 5 mL of methanol was added to the reaction solution to yield N,N,N,N-tetrakis(4-aminophenyl)-1,4-phenylenediamine.

[0159] 1 g of the 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-neck flask, and DMF was added as a solvent. The reaction was carried out at room temperature (25°C) under reflux conditions for approximately 9 hours. After the reaction was completed, the potassium carbonate was removed through a filter, and the reaction solution was placed in a separatory funnel. 10 mL of dichloromethane and 10 mL of water were added, and 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.

[0160] 1 g of N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediamine, 1.4 g of lithium bistrifluoromethanesulfonylimide, and 20 mL of dichloromethane were added to a three-neck flask and stirred. Then, 0.14 g of silver nitrate and 2 mL of water were added and the mixture was stirred for another 2 hours to react. After the reaction, dichloromethane and water were further added to the flask, and the dichloromethane layer was separated using a separatory funnel. Methanol was added to obtain bistrifluoromethanesulfonylimide N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenedimonium-d4 (compound C of formula C) (Maldi-tof m / z 1485.2 [M+H] + ).

[0161] The deuterium substitution rate of the compound C was about 17%.

[0162] Comparative Example 1 Compound D of the following formula D was synthesized by the following method.

[0163] [ka] D

[0164] A three-neck flask was charged with 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. Dimethylformamide (DMF) was added as a solvent, and the mixture was allowed to react at room temperature (25°C) under reflux for approximately 12 hours. The copper powder and potassium carbonate were removed through a filter, yielding N,N,N,N-tetrakis(4-nitrophenyl)-1,4-phenylenediamine. 1.5 g of the N,N,N,N-tetrakis(4-nitrophenyl)-1,4-phenylenediamine and 0.5 g of tin chloride were added to the three-neck flask, and 10 mL of HCl was added as a solvent. The reaction was allowed to proceed at room temperature (25°C). After the reaction was complete, 5 mL of methanol was added to the reaction solution to yield N,N,N,N-tetrakis(4-aminophenyl)-1,4-phenylenediamine.

[0165] 1 g of the 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-neck flask, and DMF was added as a solvent. The reaction was carried out at room temperature (25°C) under reflux conditions for approximately 9 hours. After the reaction was completed, the potassium carbonate was removed through a filter, and the reaction solution was placed in a separatory funnel. 10 mL of dichloromethane and 10 mL of water were added, and 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.

[0166] 1 g of the N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediamine, 1.4 g of lithium bistrifluoromethanesulfonylimide, and 20 mL of dichloromethane were added to a three-neck flask and stirred. Then, 0.14 g of silver nitrate and 2 mL of water were added and the mixture was stirred for another 2 hours to react. After the reaction, dichloromethane and water were further added to the flask, and the dichloromethane layer was separated using a separatory funnel. Methanol was added to obtain N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenedimonium (Compound D) (Maldi-tof m / z 1481.5 [M+H] + ).

[0167] The deuterium substitution rate in Comparative Example 1 was approximately 0%.

[0168] Table 1 summarizes the absorption ability of each compound in Examples 1 to 3 and Comparative Example 1. In Table 1, T%(λmax) is the transmittance at each absorption maximum wavelength. In Table 1, Td 5% is the temperature (Td 5%) at which a 95% weight loss of the compound occurs in TGA (thermogravimetric analysis).

[0169] [Table 1]

[0170] It can be seen from Table 1 that each of the compounds of Examples 1 to 3 exhibits the same light absorption characteristics as Comparative Example 1, and also exhibits excellent heat resistance.

[0171] Test example 1. A coating liquid was prepared by mixing a cyclic olefin resin (TOPAS, 5013F-04), a compound, and a solvent (cyclohexanone). The compound used was the compound synthesized in the Examples or Comparative Examples. The mixing ratio of the cyclic olefin resin, compound, and solvent was approximately 69.3:0.99:29.7 by weight (cyclic olefin resin: compound: solvent). The coating liquid was coated onto a transparent substrate (glass substrate manufactured by SCHOTT) and maintained at 140°C for approximately 2 hours to form a resin film with a thickness of approximately 6 μm.

[0172] Table 2 below summarizes the transmittance of the resin film in the visible and infrared regions before and after reliability evaluation. The reliability evaluation involved holding the resin film 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 represents the transmittance at the absorption maximum (1100 nm).

[0173] In Table 2 below, Δ is the rate of change (%) of each characteristic before and after the reliability evaluation, and is the result calculated by 100 × (AB) / B, where A is the value represented by A in Table 2 below, and B is the value represented by B in Table 2 below. In Table 2 below, T is the transmittance at the corresponding wavelength, and T min is the minimum transmittance in the wavelength range, T ave means the average transmittance within the wavelength range.

[0174] [Table 2]

[0175] Test example 2. 4 to 7 show the evaluation results for resin films produced by the method of Test Example 1 using the compounds of Examples 1 to 3 and Comparative Example 1, respectively. In Figs. 4 to 7, the horizontal axis represents wavelength (nm) and the vertical axis represents transmittance (%). The results shown before high temperature and high humidity are the results immediately after the resin film was produced, and the results shown after high temperature and high humidity are the results after the resin film was subjected to a reliability evaluation (under the same conditions as Test Example 1).

[0176] 4 to 7, the resin film using the compound of the example shows little change in light absorption characteristics before and after high temperature and humidity. In contrast, the resin film using the compound of the comparative example shows a very large change in light absorption characteristics before and after high temperature and humidity, and it can be seen that the light absorption characteristics are almost completely lost.

[0177] The main contents of Figures 4 to 7 are summarized in Table 3 below. f is the transmittance at the absorption maximum wavelength of the resin film maintained at 85°C and 85% relative humidity for 120 hours, and λ f is the absorption maximum wavelength at this time, and A i is the transmittance at the absorption maximum wavelength of the resin film before being kept at 85°C and 85% relative humidity for 120 hours, and λ i is the absorption maximum wavelength at this time.

[0178] In Table 3 below, ΔA is 100 × (A f -A i ) / A i Δλ is the value calculated by 100×(λ f -λ i ) / λ i This is the value calculated using

[0179] [Table 3]

[0180] Comparing the results in Tables 1 to 3 and Figures 4 to 7, it can be seen that the compounds of the Examples and the Comparative Examples have similar spectroscopic properties, but show large differences in absorption properties when applied to a resin film and / or absorption properties after evaluation under high temperature and humidity. From these points, it can be confirmed that the compounds can absorb light in the infrared region due to their unique structure, and at the same time, have excellent heat resistance, and can effectively form a resin film with excellent performance. [Explanation of symbols]

[0181] 100 Base material layer 200 Resin Film 300 Dielectric Film

Claims

1. A compound represented by the following formula 1. 【Chemistry 1】 Chemical 1 In Chemical Formula 1, R １ ~R ２８ are each independently hydrogen, deuterium, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryl group, an aryloxy group, an arylamino group, an alkylamino group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, an amino group, a nitro group, a nitrile group, a hydroxy group, or a cyano group; R １ ~R ２８ At least one of the atoms is deuterium.

2. The compound according to claim 1, wherein the deuterium substitution rate is 10% or more.

3. The compound of claim 1, which exhibits an absorption maximum in the wavelength range of 690 nm to 1200 nm.

4. The compound according to claim 3, having a transmittance at the absorption maximum of 50% or less.

5. 2. The compound according to claim 1, having a molar mass in the range of 900 g / mol to 3,000 g / mol.

6. The compound according to claim 1, having a 5% thermal decomposition temperature of 285°C or higher.

7. The compound of claim 1 further comprising an anion.

8. A composition comprising a resin component and the compound according to any one of claims 1 to 7.

9. 9. The composition according to claim 8, wherein the resin component comprises at least one selected from the group consisting of a cyclic olefin resin, a polyarylate resin, a polyester resin, a polysulfone resin, a polyethersulfone resin, a polyparaphenylene resin, a polyarylene ether phosphine oxide resin, a polyimide resin, a polyetherimide resin, a polyamideimide resin, an acrylic resin, a polycarbonate resin, a polyethylene naphthalate resin, and a silicone resin.

10. The composition according to claim 8, comprising 0.001 to 10 parts by weight of the compound per 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 comprises at least one selected from the group consisting of cyclic olefin 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 cyclic olefin resin.

14. The resin film according to claim 11, which exhibits an absorption maximum in the wavelength range of 690 nm to 1200 nm.

15. The resin film according to claim 11, wherein the absolute value of ΔA in the following formula 1 is 80% 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 resin film maintained at 85°C and 85% relative humidity for 120 hours, and A ｉ is the transmittance at the absorption maximum wavelength of the resin film before being kept at 85° C. and 85% relative humidity for 120 hours.

16. The resin film according to claim 11, wherein the absolute value of Δλ in the following formula 2 is 10% or less. [Formula 2] λ=100×(λ) ｆ -l ｉ ) / l ｉ In Equation 2, λ ｆ is the absorption maximum wavelength of the resin film maintained at 85°C and 85% relative humidity for 120 hours, and λ ｉ is the absorption maximum wavelength of the resin film before being kept at 85° C. and 85% relative humidity for 120 hours.

17. The resin film according to claim 15 or 16, wherein the absorption maximum wavelength is within a wavelength range of 690 nm to 1200 nm.

18. a substrate layer, and An optical filter comprising the resin film according to claim 11 formed on one or both surfaces of the substrate layer.

19. An imaging device comprising the optical filter of claim 18.

20. An infrared sensor comprising the resin film according to claim 11.

Images