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 Art

[0002] Compounds that can be used as absorbers, for example, compounds that can absorb light in the infrared region, may be applied to various uses.

[0003] For example, in imaging devices (also called solid-state imaging devices) using CCD (Charge-Coupled Device) or CMOS (complementary metal-oxide-semiconductor) image sensors, infrared sensors, etc., since they include silicon photodiodes that are sensitive to the near-infrared region, an absorber may be used.

[0004] As absorbers, for example, phthalocyanine-based, cyanine-based, metal dithiols complex-based, squarylium-based, and diimonium salt-based compounds are known.

[0005] Phthalocyanine-based compounds are known as near-infrared compounds, but have the problem of high absorption in the visible light region. Also, cyanine-based compounds have a narrow near-infrared region that can be absorbed by only a single compound, and have the problem that they must be used in mixture with other compounds. Also, metal dithiols complex-based compounds have low solubility, and when applied to a film, additional dispersion equipment is required, and they are difficult to apply to uses that require high transmittance.

[0006] Also, squarylium-based compounds are known as compounds having excellent heat resistance. However, squarylium-based compounds are difficult to absorb light in the long wavelength region of 900 nm or more. Also, iminium or diimonium-based compounds are known as compounds that can absorb light having a wavelength of 900 nm or more. However, iminium or diimonium-based compounds have the problem of losing their light absorption characteristics in an environment of high temperature and / or high humidity due to their low thermal stability.

Summary of the Invention

Problems to be Solved by the Invention

[0007] This specification discloses a compound and its uses.

[0008] The purpose of this specification is to disclose a compound that has excellent heat resistance and can stably maintain its light absorption characteristics even when high-temperature conditions or high-temperature and high-humidity conditions are maintained. In addition, this specification aims to ensure desired light characteristics by applying the above compound. Further, this specification aims to disclose the uses of the above compound.

Means for Solving the Problems

[0009] Among the physical properties mentioned in this specification, unless otherwise specified, the physical properties whose measurement temperature affects the results are the results measured at normal temperature.

[0010] The term "normal temperature" means the natural temperature without artificial heating and cooling, for example, any temperature within the range of 10°C to 30°C, a temperature of about 23°C or about 25°C.

[0011] Unless otherwise specified in this specification, the unit of temperature is °C.

[0012] Among the physical properties mentioned in this specification, when the pressure affects the results, unless otherwise specified, the physical properties are the physical properties measured under normal pressure. The term "normal pressure" means the natural pressure without artificial pressurization and depressurization, and usually, a pressure within the range of about 700 mmHg to 800 mmHg is referred to as normal pressure.

[0013] Among the physical properties mentioned in this specification, when the humidity affects the results, unless otherwise specified, the physical properties are the physical properties measured under the humidity of the standard state. The humidity of the standard state means any humidity within the range of 40% to 60% in relative humidity, for example, a relative humidity of about 40% or 60%.

[0014] When the optical properties (e.g., refractive index) referred to in this specification are properties that vary with wavelength, unless otherwise specified, the applicable optical property is the property with respect to light having a wavelength of 520 nm.

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

[0016] Unless otherwise specified, the terms average transmittance or average absorbance are the results obtained by measuring the transmittance or absorbance at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength within a predetermined wavelength region, and then obtaining the arithmetic mean of the measured transmittances or absorbances. For example, the average transmittance or average absorbance within the wavelength range of 350 nm to 360 nm is the arithmetic mean of the transmittances or absorbances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

[0017] Unless otherwise specified, the terms maximum transmittance or maximum absorbance are the maximum transmittance or maximum absorbance when measuring the transmittance or absorbance at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength within a predetermined wavelength region. For example, the maximum transmittance or maximum absorbance within the wavelength range of 350 nm to 360 nm is the highest transmittance or absorbance among the transmittances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

[0018] The minimum transmittance or minimum absorbance of a term refers to the minimum transmittance or minimum absorbance when measuring the transmittance or absorbance at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength within a predetermined wavelength range. For example, the minimum transmittance or minimum absorbance within the wavelength range of 350 nm to 360 nm is the lowest transmittance or absorbance among the transmittances or absorbances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

[0019] In this specification, the incident angle is an angle based on the normal line of the surface to be evaluated. For example, the transmittance at an incident angle of 0 degrees of an optical filter means the transmittance for light incident in a direction substantially parallel to the normal line of the surface of the optical filter. Such a definition of the incident angle is similarly applicable to other characteristics such as transmittance and absorbance.

[0020] In this specification, the term "alkyl group" means 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 may be linear, branched, or cyclic. The alkyl group may optionally be substituted with at least one substituent. Such content is applicable to all alkyl groups mentioned in this specification unless otherwise specified.

[0021] In this specification, the term "alkenyl group" means 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 may be linear, branched, or cyclic. The alkenyl group may optionally be substituted with at least one substituent. Such content is applicable to all alkenyl groups mentioned in this specification unless otherwise specified.

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

[0023] As used herein, the term "alkoxy group" means 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 may be linear, branched, or cyclic. The alkoxy group may optionally be substituted by at least one substituent. Such content applies to all alkoxy groups mentioned in this specification unless otherwise specified.

[0024] As used herein, the term "aryl group" means a monovalent residue derived from an aromatic hydrocarbon, and the aryl group may be an aryl group having 6 to 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, and may be, for example, a phenyl group, a tolyl group, a xylyl group, or a naphthyl group. The aryl group may also optionally be substituted by at least one substituent. Such content applies to all aryl groups mentioned in this specification unless otherwise specified.

[0025] Also, as used herein, the aryl group may be, for example, a heteroaryl group, and the heteroaryl group is 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 optionally be substituted by at least one substituent. Such content applies to all heteroaryl groups mentioned in this specification unless otherwise specified.

[0026] This specification discloses a compound. The compound may be an absorbent. The term absorbent means a compound capable of absorbing light in any wavelength range.

[0027] The compound may be a compound represented by Chemical Formula 1 below.

[0028]

Chemical Formula

[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 (alkylsilyl group) or a silyl group in which at least one aryl group is bonded to silicon (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 optionally be substituted by at least one substituent. At this time, examples of any at least one substituent include, but are not limited to, 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.

[0032] More specifically, in Chemical Formula 1, R1 to R20 may be hydrogen, deuterium, an alkyl group, an alkenyl group, an alkynyl group, an alkyl group substituted with deuterium, an alkenyl group substituted with deuterium or an alkynyl group substituted with deuterium, but is not limited thereto, where the substituent is as described for the aforementioned R1 to R 28 as described above.

[0033] Also, in Chemical Formula 1, among the aforementioned R1 to R 28 , any pair of substituents (for example, substituents adjacent to each other) may be bonded to each other to form an aliphatic, aromatic, aliphatic hetero or aromatic hetero fused ring structure. The pair of adjacent substituents means a pair of a substituent and a substituent substituted on an atom directly connected to the atom substituted with the substituent, a pair of a substituent and a substituent that is sterically closest to the substituent, or a pair of a substituent and another substituent substituted on the atom substituted with the substituent. For example, two substituents substituted at the ortho position in a benzene ring or two substituents substituted at the same carbon in an aliphatic ring correspond to groups adjacent to each other.

[0034] Also, Chemical Formula 1 may have a structure that includes an absorption edge and can exhibit the property 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 a compound, particularly an organic compound, is caused by the energy difference (ΔE) between the ground state and the excited state, and this difference is also explained as the energy difference between the HOMO (Highest Unoccupied Molecular Orbital) and the LUMO (Lowest Unnoccupied Molecular Orbital).

[0036] Generally, the organic absorbent may include a resonance structure and / or a conjugated bond as an absorption edge capable of exhibiting a light absorption effect. Thereby, the compound may form a skeleton that can exhibit desired light absorption characteristics as a whole.

[0037] The specific types of the absorption edge or the skeleton as described above are not particularly limited. The known resonance effect means the interaction between the π-bond electron pair adjacent to the lone pair of electrons of the molecule, and the substituents or skeletons that cause such a resonance effect are known. Also, a conjugated bond is a system in which two or more double bonds are constituted via a single bond, and it is known that as the length of such a conjugated bond increases, the energy difference between HOMO and LUMO becomes smaller and the absorption band moves to the long wavelength side.

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

[0039] The compound disclosed in the present specification exhibits an absorption maximum wavelength within the range of 690 nm to 1200 nm. The lower limit of the absorption maximum wavelength 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 in other examples. Also, the upper limit of the absorption maximum wavelength may be about 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 the range that is greater than or exceeds any of the lower limits described above, or within the range that is less than or equal to any of the upper limits described above while being greater than or exceeding any of the lower limits described above.

[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 highest unoccupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), 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 in the above-mentioned range.

[0041] The compound disclosed herein is a compound represented by the formula 1 in which R 28 At least one of R1 to R2 contains deuterium. 28 At least one of R1 to R2 is deuterium. 28 at least one of which 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 does not affect the light absorption characteristics of the compound, and excellent heat resistance can be ensured. More specifically, the compound represented by Chemical formula 1 has R1 to R 20 The deuterium contained in the material ensures excellent heat resistance.

[0043] In Chemical Formula 1, R1 to R 28The lower limit of the number of deuteriums contained therein 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 thereof 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 deuteriums may be within the range greater than or exceeding any of the lower limits described above, or within the range less than or equal to any of the upper limits described above, or within the range greater than or exceeding any of the lower limits described above while being less than or equal to any of the upper limits described above.

[0044] The deuterium substitution rate of the compounds disclosed in this specification may be at a certain level or higher. 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 that 1 mole of the compound has 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 thereof 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 within the range greater than or exceeding any of the lower limits described above, within the range less than or equal to any of the upper limits described above, or within the range greater than or exceeding any of the lower limits described above while being less than or equal to any of the upper limits described above. Also, the deuterium substitution rate means the degree to which the hydrogen directly bonded to carbon is substituted with deuterium. The method for measuring such a deuterium substitution rate is described in "5. Deuterium Substitution Rate" in the Examples section of this specification.

[0045] 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 is understood that the bond between carbon and deuterium can reduce the intramolecular vibration energy with respect to the carbon-hydrogen bond and can maintain the light absorption characteristics and ensure heat resistance even in a high-temperature and high-humidity environment.

[0046] The compound may have an appropriate level of molar weight. For example, the lower limit of the molar weight 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 weight 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 weight may be within the range above or exceeding any of the lower limits described above, or within the range below or equal to any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being below or equal to any of the upper limits described above.

[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 Td5% of the compound may 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 the Td 5% may 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. The Td 5% may be within a range above or exceeding any of the lower limits described above, or within a range less than or equal to any of the upper limits described above, or within a range above or exceeding any of the lower limits described above while being less than or equal to any of the upper limits described above.

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

[0049] The compound may contain anions. Examples of the anion include, for example, halogen ions, hexafluoroantimonate ions (SbF6-), perchlorate ions, thiocyanate ions (SCN-), hexafluorophosphate ions (PF6-), phosphate ions, bis(trifluoromethanesulfonyl)imide ions (Bis trifluoromethanesulfonyl imide anion), tetrafluoroborate ions (BF 4-) Trifluoro methylcarboxylic acid anion, Alkylsulfonic acid anion, Benzenesulfonic acid anion, Toluenesulfonic acid anion, Benzenecarboxylic acid anion, Alkylcarboxylic acid anion, Periodic acid anion, Hydro fluoro borate anion, Tetraphenylboricacid anion, etc. are included, but are not limited thereto.

[0050] The compound is obtained by a known method for synthesizing organic compounds and a method for deuterium substitution.

[0051] The structure of Chemical Formula 1 is the structure of an absorbent known as a so-called dimonium salt-based compound. In the art, various methods for producing dimonium salt-based compounds are known. Therefore, for example, the compound of Chemical Formula 1 may be produced by, for example, substituting the reactant used in the production process of a known dimonium salt-based absorbent with deuterium and applying this reactant to the synthesis process of the dimonium salt-based absorbent. Also, for example, after synthesizing a dimonium salt-based absorbent by a known synthesis method, the compound may also be produced by a method of substituting at least a part or all of the hydrogen of the synthesized absorbent with deuterium.

[0052] There is no particular limitation on the deuterium substitution method in the above. For example, a method of mixing deuterium of a compound to be substituted with deuterium at an appropriate temperature may be applied. In the above, 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 thereof 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 within the range above any of the lower limits described above or exceeding the range, or within the range below or equal to any of the upper limits described above, or within the range below or equal to any of the upper limits described above while being above or exceeding any of the lower limits described above.

[0053] The mixing time is also not particularly limited and may be adjusted, for example, in consideration of a desired substitution rate or the like. 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 thereof may be about 72 hours, 36 hours or 24 hours. The mixing time may be within the range above any of the lower limits described above or exceeding the range, or within the range below or equal to any of the upper limits described above, or within the range below or equal to any of the upper limits described above while being above or exceeding any of the lower limits described above.

[0054] Also, the mixing may be performed, for example, in the presence of additional compounds that can assist, promote, or initiate the substitution with deuterium. For example, compounds that function as catalysts for the substitution with deuterium may include any of silver oxide (Ag2O), silver acetate (AgOAc), silver trifluoroacetate (CF3COOAg), silver carbonate (Ag2CO3), 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 are not limited thereto as long as they are compounds that function as catalysts during deuterium substitution. Also, compounds that function as ligands during deuterium substitution may include, for example, 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, 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, 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(phenylphosphinidene)ferrocene, 1,1’-bis(phenylphosphinidene)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-diazaphospholidine, 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, 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-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-(di(3,5-bis-trifluoromethylphenyl)phosphino)ferrocenyl]ethyldi(3,5-dimethylphenyl)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)ferrocene(1,2,3,4,It may be any of 5-Pentaphenyl-1’-(di-tert-butylphosphino)ferrocene), but is not limited thereto as long as it is a compound that functions as a ligand upon deuterium substitution.

[0055] This specification further discloses a composition containing the above compound. The term "composition" means a mixture containing a compound and other components or a mixture containing two or more compounds.

[0056] A composition containing such a compound basically contains the compound of Chemical Formula 1 and may further contain other necessary components.

[0057] For example, the composition may further contain a resin component that functions as a binder. There is no particular limitation on the type of resin component applicable in this case, and known resin components used to form a resin film, for example, a near-infrared resin film, may be applicable. In this specification, the compound component can exhibit appropriate compatibility or solubility with the various known resin components.

[0058] Examples of the resin component include at least one of cyclic olefin (COP, Cycloolefin)-based resins, polyarylate resins, polyester resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyetherimide resins, polyamideimide resins, acrylic resins, polycarbonate resins, polyethylene naphthalate resins, or silicone resins, etc., and various other organic resins or organic-inorganic hybrid resins, but are not limited thereto.

[0059] Although not particularly limited, the compound of this specification may form a resin film that exhibits excellent performance when mixed with a cyclic olefin-based resin among the resin components that function as the known binder. Therefore, in one example, the resin component may be a cyclic olefin-based resin.

[0060] When the resin component is applied, its proportion is not particularly limited. For example, the resin component may be present such that the weight proportion of the compound relative to 100 parts by weight of the resin component is in the range of 0.001 part by weight to 10 parts by weight. The lower limit of the weight proportion of the compound relative to 100 parts by weight of the resin component may, in other examples, be about 0.001 part by weight, 0.005 part by weight, 0.01 part by weight, 0.05 part by weight, 0.1 part by weight, 0.5 part by weight, 1 part by weight, 1.1 parts by weight, 1.2 parts by weight, 1.3 parts by weight or 1.4 parts by weight, and the upper limit may be about 10 parts by weight, 9 parts by weight, 8 parts by weight, 7 parts by weight, 6 parts by weight, 5 parts by weight, 4 parts by weight, 3 parts by weight, 2 parts by weight or 1.5 parts by weight. The proportion may be within the range that is equal to or greater than any of the lower limits described above or exceeds the range, or within the range that is less than or equal to any of the upper limits described above or below the range, or within the range that is equal to or greater than any of the lower limits described above or exceeds the range while being less than or equal to any of the upper limits described above or below the range.

[0061] For example, the composition may further contain a solvent in which the compound and / or the resin component is dispersed. There is no particular limitation on the type of solvent applied in this case, and known solvents used for forming a resin film, for example, a near-infrared resin film, may be applied. In the present specification, the compound component can exhibit appropriate compatibility or solubility with respect to the various known solvents.

[0062] Examples of solvents 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 2 or more carbon atoms (e.g., isobutyl alcohol, isopropyl alcohol, ethanol, isopropanol, butanol, etc.), butyl acetate, tetrahydrofuran or xylene, etc.

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

[0064] The composition may further contain any other optional components necessary for the foregoing components. Examples of the optional components include, but are not limited to, adhesion promoters, leveling agents, antistatic agents, heat stabilizers, light stabilizers, antioxidants, dispersants, flame retardants, lubricants or plasticizers, etc.

[0065] This specification further relates to the use of the compound or the composition.

[0066] For example, this specification may relate to a resin film to which the compound or the 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 the resin component and the ratio between the resin component and the compound, etc. are as described in the item of 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 can exhibit absorption characteristics, for example, in at least a part of the wavelength range within the range of about 690 nm to 1200 nm.

[0070] For example, the resin film can exhibit a maximum absorption wavelength within the range of 690 nm to 1200 nm. The lower limit of the maximum absorption wavelength 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 in other examples. Also, the upper limit of the maximum absorption wavelength may be about 1200 nm, 1190 nm, 1180 nm, 1170 nm, 1160 nm, 1150 nm, 1140 nm, 1130 nm, 1120 nm or 1100 nm. The maximum absorption wavelength may be within the range above or exceeding any of the lower limits described above, or within the range below or equal to any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being within the range below or equal to any of the upper limits described above.

[0071] Due to such characteristics, the resin film can 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 below a certain level. The upper limit may be about 50%, 49%, 48%, 47%, 46%, 45%, 44%, 43%, 42%, 41% or 40%, and the lower limit may be about 0.1%, 1%, 10%, 15%, 20%, 25%, 30%, 35% or 39%. The transmittance at the absorption maximum may be within the range above any of the lower limits described above or in excess, or within the range below or less than any of the upper limits described above, or within the range above or in excess of any of the lower limits described above while being below or less than any of the upper limits described above.

[0073] For example, for the resin film, let the transmittance at the absorption maximum wavelength of the resin film held at 85 °C and 85% relative humidity for 120 hours be A f and the transmittance at the absorption maximum wavelength of the resin film before being held at 85 °C and 85% relative humidity for 120 hours be A i When doing so, A f - A i The upper limit of the absolute value 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%. For the said A f - A i The absolute value may be within the range below or less than any of the upper limits described above, or within the range above or in excess of any of the lower limits described above while being below or less than any of the upper limits described above.

[0074] For example, in the resin film, the absolute value of ΔA in the following formula 1 may be below a predetermined value.

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

[0076] In formula 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 maintained at 85 °C and 85% relative humidity for 120 hours, and the absorption maximum wavelength exists 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 is less than or within the range of any of the upper limits described above, or is greater than or exceeds any of the lower limits described above, but is less than or within the range of any of the upper limits described above.

[0078] In the above Formula 1, A f The upper limit of may be about 80%, 75%, 70%, 65%, 60%, 55%, 50% or 45%, and the lower limit thereof may be about 10%, 20%, 30%, 40%, 50%, 60% or 65%. The A f is less than or within the range of any of the upper limits described above, or is greater than or exceeds any of the lower limits described above, but is less than or within the range of any of the upper limits described above.

[0079] The absolute value of Δλ in the following Formula 2 for the resin film may be less than or equal to a predetermined value.

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

[0081] In Formula 2, λ fis the absorption maximum wavelength of the resin film maintained at 85 °C and 85% relative humidity for 120 hours, λ i is the absorption maximum wavelength of the resin film before being maintained at 85 °C and 85% relative humidity for 120 hours, and the absorption maximum wavelength exists within the wavelength range of 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 the Δλ is less than any of the upper limits described above or within the following ranges, or is greater than or exceeds any of the lower limits described above while being less than or within any of the upper limits described above.

[0083] In the above Equation 2, λ f and λ i may each be within the range of 690 nm to 1200 nm. The lower limit of each of the λ f and λ i in other examples 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. Also, the upper limit of each of the λ f and λ i may be about 1200 nm, 1190 nm, 1180 nm, 1170 nm, 1160 nm, 1150 nm, 1140 nm, 1130 nm, 1120 nm or 1100 nm. Each of the λ f and λ i is within the range greater than or exceeding any of the lower limits described above, or within the range less than or below any of the upper limits described above, or is greater than or exceeds any of the lower limits described above while being less than or within any of the upper limits described above.

[0084] Through the absorption characteristics, the resin film is applied to devices such as various optical filters and infrared sensors, and desired characteristics can be efficiently achieved.

[0085] In this specification, the resin film may be formed by a known method as long as the compound or composition of the present application is applied. For example, the compound composition may be coated by an appropriate method, and a curing or drying process may be performed as necessary to form the resin film.

[0086] There is no particular limitation on the thickness of the resin film, and the thickness may be adjusted in consideration of desired characteristics. In one example, the resin film may have a thickness in the range of about 0.5 to 20 μm.

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

[0088] FIG. 1 shows an example of the optical filter, in which the resin film 200 is formed on one side of the substrate layer 100.

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

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

[0091] In one example, the substrate layer may be a so-called near-infrared absorption substrate. A near-infrared absorption substrate is a substrate that exhibits absorption characteristics in at least a part of the near-infrared region. So-called Blue Glass, which exhibits the above characteristics by containing copper, is a typical example of the near-infrared absorption substrate. Such a near-infrared absorption substrate is useful for constituting an optical filter that blocks light in the near-infrared region, but is disadvantageous in terms of ensuring a high transmittance in the visible light region due to the absorption characteristics, and is also disadvantageous in terms of durability. In this specification, by selecting a near-infrared absorption substrate and combining it with a specific resin film, it is possible to provide an optical filter that efficiently blocks desired light, exhibits high transmittance characteristics in the visible light region, and has excellent durability.

[0092] As the infrared absorption substrate, a substrate that exhibits an average transmittance of a certain level or higher within the range of 425 nm to 560 nm may be used. The lower limit of the average transmittance may be about 75%, 77%, 79%, 81%, 83%, 85%, 87% or 89%, and the upper limit thereof may be about 98%, 96%, 94%, 92% or 90%. The average transmittance may be within the range of equal to or exceeding any of the lower limits described above, or within the range of less than or equal to any of the upper limits described above while being equal to or exceeding any of the lower limits described above.

[0093] As the infrared absorption substrate, a substrate that exhibits a maximum transmittance of a certain level or higher within the range of 425 nm to 560 nm may be used. The lower limit of the maximum transmittance may be about 80%, 82%, 84%, 86%, 88% or 90%, and the upper limit thereof may be about 100%, 98%, 96%, 94%, 92% or 90%. The maximum transmittance may be within the range of equal to or exceeding any of the lower limits described above, or within the range of less than or equal to any of the upper limits described above while being equal to or exceeding any of the lower limits described above.

[0094] As the infrared absorption substrate, a substrate showing an average transmittance of a certain level or higher within the range of 350 nm to 390 nm may be used. The lower limit of the average transmittance may be about 75%, 77%, 79%, 81% or 83%, and the upper limit thereof may be about 98%, 96%, 94%, 92%, 90%, 88%, 86% or 84%. The average transmittance may be within the range of equal to or higher than any of the lower limits described above or exceeding the lower limits, or while being equal to or higher than any of the lower limits described above or exceeding the lower limits, within the range of less than or equal to any of the upper limits described above.

[0095] As the infrared absorption substrate, a substrate showing a maximum transmittance of a certain level or higher within the range of 350 nm to 390 nm may be used. The lower limit of the maximum transmittance may be about 80%, 82%, 84%, 86% or 87%, and the upper limit thereof may be about 100%, 98%, 96%, 94%, 92%, 90% or 88%. The maximum transmittance may be within the range of equal to or higher than any of the lower limits described above or exceeding the lower limits, or while being equal to or higher than any of the lower limits described above or exceeding the lower limits, within the range of less than or equal to any of the upper limits described above.

[0096] As the infrared absorption substrate, the transmittance at a wavelength of 700 nm may be within a certain range. The lower limit may be about 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26% or 28%, and the upper limit thereof may be about 45%, 43%, 41%, 39%, 37%, 35%, 33%, 31% or 29%. The transmittance may be within the range of equal to or higher than any of the lower limits described above or exceeding the lower limits, or within the range of less than or equal to any of the upper limits described above, or while being equal to or higher than any of the lower limits described above or exceeding the lower limits, within the range of less than or equal to any of the upper limits described above.

[0097] As for the infrared absorption substrate, the average transmittance may be within a certain range within the 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 within the range above or exceeding any of the lower limits described above, or within the range below or equal to any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being below or equal to any of the upper limits described above.

[0098] As for the infrared absorption substrate, the maximum transmittance may be within a certain range within the range of 700 nm to 800 nm. The lower limit may be about 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26% or 28%, and the upper limit may be about 43%, 41%, 39%, 37%, 35%, 33%, 31% or 29%. The maximum transmittance may be within the range above or exceeding any of the lower limits described above, or within the range below or equal to any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being below or equal to any of the upper limits described above.

[0099] As for the infrared absorption substrate, the average transmittance may be within a certain range within 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 within the range above or exceeding any of the lower limits described above, or within the range below or equal to any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being below or equal to any of the upper limits described above.

[0100] As for the infrared absorption substrate, the maximum transmittance may be within a certain range within the 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 within the range above or exceeding any of the lower limits described above, or within the range below or equal to any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being within the range below or equal to any of the upper limits described above.

[0101] As for the infrared absorption substrate, the average transmittance may be within a certain range within the range of 1000 nm to 1200 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 within the range above or exceeding any of the lower limits described above, or within the range below or equal to any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being within the range below or equal to any of the upper limits described above.

[0102] As for the infrared absorption substrate, the maximum transmittance may be within a certain range within the range of 1000 nm to 1200 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 within the range above or exceeding any of the lower limits described above, or within the range below or less than any of the upper limits described above, or within the range above or exceeding any of the lower limits described above while being below or less than any of the upper limits described above.

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

[0104] As such a substrate, a substrate known as so-called infrared absorption glass may be used. Such glass is an absorption-type glass produced by adding CuO or the like to phosphate fluoride glass, phosphate glass, or the like. Therefore, in one example, in this specification, as the infrared absorption substrate, a CuO-containing phosphate fluoride glass substrate or a CuO-containing phosphate glass substrate may be used. The phosphate glass includes K phosphate glass in which a part of the glass skeleton is composed of SiO2. Such absorption-type glass is known, and for example, glass disclosed in Korean Registered Patent No. 10-2056613 or other commercially available absorption-type glass (for example, commercially available products from Hoya, Schott, PTOT, etc.) may be used.

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

[0106] The copper content can be confirmed using a wavelength dispersive X-ray fluorescence spectrometry (WD XRF) apparatus. When the specimen (substrate layer) is irradiated with X-rays using the apparatus, characteristic secondary X-rays are generated from the individual elements of the specimen, and the apparatus detects the secondary X-rays according to the wavelength for each element. The intensity of the secondary X-rays is proportional to the content of the element, and thus, quantitative analysis may be performed through the intensity of the secondary X-rays measured according to the wavelength for each element.

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

[0108] The optical filter of this specification may further include other known configurations necessary for the substrate layer and the resin film.

[0109] For example, the optical filter may further include a dielectric film. The dielectric film may further include, for example, a so-called dielectric film on one or both sides of the substrate layer.

[0110] Figures 2 and 3 are illustrations of an optical filter with a dielectric film 300 added, showing a case where the dielectric film 300 is formed on one or both sides of a laminated structure including a substrate layer 100 and a resin film 200.

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

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

[0113] The material for forming the dielectric film, that is, the type of the material for forming each sub-layer is not particularly limited, and known materials may be applied. Usually, for the production of the low refractive index sub-layer, fluorides such as SiO2 or Na5Al3F14, Na3AlF6 or MgF2 are applied, and for the production of the high refractive index sub-layer, amorphous silicon, TiO2, Ta2O5, Nb2O5, ZnS or ZnSe may be applied, but the materials applied in this specification are not limited to the above.

[0114] The method for forming the dielectric film as described above is not particularly limited. For example, a known vapor deposition method may be applied for formation. In the art, a method for controlling the reflection or transmission characteristics of the dielectric film by considering the vapor deposition thickness and the number of layers of the sub-layer is known, and in this specification, the dielectric film may be formed by such a known method.

[0115] Further, the optical filter may further include a resin film that exhibits absorption characteristics with respect to ultraviolet rays (hereinafter referred to as an ultraviolet resin film) as a resin film that is distinguished from the resin film. However, such a resin film is not an essential component. For example, an ultraviolet compound described later may be introduced 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 region of about 300 nm to 390 nm.

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

[0118] For example, as the ultraviolet compound, a known compound showing an absorption maximum in the wavelength range of about 300 nm to 390 nm may be applied.

[0119] The materials and configuration methods for constituting such an ultraviolet resin film are not particularly limited, and known materials and configuration methods may be applied.

[0120] Generally, the ultraviolet resin film is formed using a material in which an ultraviolet compound capable of showing a desired absorption maximum is blended with a transparent resin. At this time, as the transparent resin, the resin component applied to the compound composition may be applied.

[0121] In addition to the aforementioned layers, various necessary layers may be added to the optical filter as long as the desired effect is not impaired.

[0122] This specification further relates to an imaging device including the optical filter. At this time, the configuration method of the imaging device and the application method of the optical filter are not particularly limited, and known configurations and application methods may be applied.

[0123] In addition, the use of the optical filter in this specification is not limited to the imaging device, and it may be applied to various other applications requiring near-infrared cut, for example, display devices such as PDPs.

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

[0125] In addition, the uses of the compound compositions or resin films described in this specification are not limited to the optical filters, infrared sensors, and / or imaging devices described above, and may also be applied to various other uses that require infrared cut-off, such as electrical components such as LiDAR.

Advantages of the Invention

[0126] This specification discloses a compound and its uses. This specification can provide a compound that has excellent heat resistance and can stably maintain its light absorption characteristics even when high-temperature conditions or high-temperature and high-humidity conditions are maintained. This specification can further provide a resin film to which the compound is applied and which ensures desired optical characteristics. This specification can further provide uses of the compound.

Brief Description of the Drawings

[0127]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Modes for Carrying Out the Invention

[0128] The compounds and the like disclosed in this specification will be specifically described through the following examples and comparative examples, but the scope of the compounds and the like is not limited by the following examples.

[0129] 1. Absorption maximum measurement method The absorption maximum of the compound was evaluated by a conventional method. Specifically, after dissolving the sample (compound) in chloroform at a concentration of about 10 -5 M, it 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 target (for example, a resin film) so that the horizontal and vertical sides were 10 mm and 10 mm, respectively. The transmittance spectrum was measured for each wavelength according to the manual of the said device. The specimen was placed on a straight line between the measurement beam and the detector of the spectrophotometer, and the transmittance spectrum was confirmed with the incident angle of the measurement beam being 0 degrees. The incident angle of 0 degrees is a direction substantially parallel to the normal direction of the surface of the specimen.

[0131] In the transmittance spectrum, the average transmittance within a predetermined wavelength range is the arithmetic mean of the transmittances measured after measuring the transmittance at each wavelength while increasing the wavelength by 1 nm from the shortest wavelength of the wavelength range. The maximum transmittance is the highest transmittance among the transmittances measured while increasing the wavelength by 1 nm each time, and the minimum transmittance is the lowest transmittance among the transmittances measured while increasing the wavelength by 1 nm each time. For example, the average transmittance within the wavelength range of 350 nm to 360 nm is the arithmetic mean of the transmittances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm. The maximum transmittance within the wavelength range of 350 nm to 360 nm is the highest transmittance among the transmittances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm, and the minimum transmittance within the wavelength range of 350 nm to 360 nm is the lowest transmittance among the transmittances measured at the wavelengths of 350 nm, 351 nm, 352 nm, 353 nm, 354 nm, 355 nm, 356 nm, 357 nm, 358 nm, 359 nm, and 360 nm.

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

[0133] 4. Mass analysis (Maldi-tof) Mass spectrometry of the compound was performed using a MALDI TOF Voyager DE-STR instrument (Applied Biosystems, USA), measured in Positive mode in Reflector mode, and analyzed using a Dithranol matrix.

[0134] 5. Deuterium substitution rate The deuterium substitution rate of the compound was measured through hydrogen nuclear magnetic resonance ( 1 H NMR) analysis. For the compound substituted with deuterium (sample compound) and the compound with the same structure before substitution with deuterium (Reference compound), 1 H-NMR analysis was performed respectively. Through the 1 H-NMR analysis of the Reference compound, the position and area of the hydrogen peak of the compound were confirmed. 1 H-NMR analysis of the sample compound was performed to confirm the position and area of the peak of hydrogen rather than deuterium and the position and area of the peak of deuterium in the compound. The deuterium substitution rate was confirmed by comparing the peak positions and areas.

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

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

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

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

[0139] Example 1. Compound A of the following Chemical A was synthesized by the following method.

[0140] [Chemical formula] Compound A

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

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

[0143] The deuterium-substituted Compound A1 was synthesized by the following method. 9.21 g of Compound D of Comparative Example 1, 0.54 g of silver carbonate (Ag2CO3), and 1.34 g of cyclohexyldiphenylphosphine were placed in a three-necked flask equipped with a reflux device. 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 further stirred for about 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] 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 silver nitrate and 1 mL of water were added, and the mixture was further stirred at room temperature (25 °C) for about 2 hours. After stirring, dichloromethane and water were further added to the flask, and the dichloromethane layer was separated with a separatory funnel. Methanol was added to obtain the target compound (bis(trifluoromethanesulfonyl)imide N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediimmonium-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 Chemical Formula B was synthesized by the following method.

[0147]

Chemical Formula

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

[0149] 1-Iodo-4-nitrobenzene was substituted with deuterium. The deuterium substitution was carried out by the deuterium substitution method of Compound A1 in Example 1 above, but using 2.49 g of 1-iodo-4-nitrobenzene instead of 9.21 g of Compound D in Comparative Example 1.

[0150] 2.0 g of the 1-iodo-4-nitrobenzene substituted with deuterium, 0.2 g of 1,4-phenylenediamine, 0.04 g of copper powder, and 0.59 g of potassium carbonate were charged into a three-necked flask. After charging dimethylformamide (DMF) as a solvent, the reaction was carried out at room temperature (25 °C) and reflux conditions for about 12 hours. The copper powder and potassium carbonate were removed through a filter to obtain 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-necked flask, 10 mL of HCl was charged as a solvent, and 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-phenylenediamine.

[0151] 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 placed in a three - necked flask. After adding DMF as a solvent, the reaction was carried out at room temperature (25 °C) and reflux conditions for about 9 hours. After the reaction was completed, potassium carbonate was removed through a filter. The reaction solution was put into a separatory funnel, then 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 bis(trifluoromethanesulfonyl)imide, and 20 mL of dichloromethane were added to a three - necked flask and stirred. Then 0.14 g of silver nitrate and 2 mL of water were added, and the mixture was stirred for about 2 hours to react. After the reaction, dichloromethane and water were further added to the flask. The dichloromethane layer was separated with a separatory funnel, and methanol was added to obtain bistrifluoromethanesulfonylimide N,N,N,N - tetrakis(p - diisobutylaminophenyl)-p - phenylene diimonium - d16 (Compound B of Chemical Formula B) (Maldi - tof m / z1496.2[M + H] + )。

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

[0154] Example 3. Compound C of the following Chemical Formula C was synthesized by the following method.

[0155]

Chemical Formula

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

[0157] First, deuterium-substituted 1,4-phenylenediamine was synthesized. The deuterium substitution was carried out by the deuterium substitution method of Compound A1 in Example 1, but 1 g of 1,4-phenylenediamine was used instead of 9.21 g of Compound D9 in Comparative Example 1.

[0158] 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 were charged into a three-necked flask, and dimethylformamide (DMF) was charged as a solvent, and the reaction was carried out at room temperature (25 °C) and reflux conditions for about 12 hours. The copper powder and potassium carbonate were removed through a filter to obtain 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-necked flask, 10 mL of HCl was charged as a solvent, and 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-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-necked flask, and after DMF was charged as a solvent, the reaction was carried out at room temperature (25 °C) and reflux conditions for about 9 hours. After the reaction was completed, potassium carbonate was removed through a filter, the reaction solution was put into 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 bis(trifluoromethanesulfonyl)imide, and 20 mL of dichloromethane were added to a three-necked flask and stirred. Then, 0.14 g of silver nitrate and 2 mL of water were added, and the mixture was stirred for about 2 hours to cause a reaction. After the reaction, dichloromethane and water were further added to the flask, and the dichloromethane layer was separated with a separatory funnel. Methanol was added to obtain bistrifluoromethanesulfonylimide N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediimmonium-d4 (Compound C of Chemical Formula C) (Maldi-tof m / z 1485.2 [M+H] + ).

[0161] The deuterium substitution rate of Compound C was about 17%

[0162] Comparative Example 1 Compound D of the following Chemical Formula D was synthesized by the following method

[0163] [Chemical Formula] Chemical Formula D

[0164] 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. The reaction was carried out at room temperature (25°C) and reflux conditions for about 12 hours. The copper powder and potassium carbonate were removed through a filter to obtain 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-necked flask, and 10 mL of HCl was added as a solvent. 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-phenylenediamine

[0165] 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. After adding DMF as a solvent, the mixture was reacted at room temperature (25 °C) and reflux conditions for about 9 hours. After the reaction was completed, potassium carbonate was removed through a filter. 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 bis(trifluoromethanesulfonyl)imide, and 20 mL of dichloromethane were added to a three-necked flask and stirred. Then, 0.14 g of silver nitrate and 2 mL of water were added, and the mixture was further stirred and reacted for about 2 hours. After the reaction, dichloromethane and water were further added to the flask, the dichloromethane layer was separated with a separatory funnel, and methanol was added to obtain N,N,N,N-tetrakis(p-diisobutylaminophenyl)-p-phenylenediimonium (Compound D of Chemical Formula D) (Maldi-tof m / z 1481.5 [M+H] + )

[0167] The deuterium substitution rate of Comparative Example 1 was about 0%.

[0168] Table 1 summarizes the absorption capabilities of the compounds of 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 95% of the weight loss of the compound occurs in the TGA (Thermogravimetric analysis) analysis.

[0169]

Table 1

[0170] From Table 1, it can be confirmed that each of the compounds in Examples 1 to 3 exhibits light absorption characteristics equivalent to those of Comparative Example 1 and excellent heat resistance.

[0171] Test Example 1. A coating solution was prepared by mixing a cyclic olefin resin (TOPAS, 5013F-04), a compound, and a solvent (Cyclohexanone). As the compound, the compound synthesized in the example or comparative example was used. The mixing ratio of the cyclic olefin resin, the compound, and the solvent was about 69.3:0.99:29.7 as a weight ratio (cyclic olefin resin:compound:solvent). The coating solution was coated on a transparent substrate (SCHOTT glass substrate) and held at 140 °C for about 2 hours to form a resin film having a thickness of about 6 μm.

[0172] Table 2 below summarizes the transmittance before and after the evaluation of the reliability in the visible light and infrared regions of the resin film. The evaluation of the reliability is an evaluation in which the resin film is held at 85 °C and 85% relative humidity for 120 hours. In Table 2 below, B represents the result before the reliability evaluation, and A represents the result after the reliability evaluation. Also, in Table 2 below, Λmax means the transmittance at the absorption maximum (1100 nm).

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

[0174]

Table 2

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

[0176] Referring to Figures 4 to 7, the resin films using the compounds of the examples have little change in light absorption characteristics before and after high temperature and high humidity. In contrast, it can be confirmed that the resin films using the compounds of the comparative example have a very large change in light absorption characteristics before and after high temperature and high humidity, and the light absorption characteristics are almost lost.

[0177] Summarizing the main content of Figures 4 to 7, it is as shown in Table 3 below. In Table 3 below, A f is the transmittance at the maximum absorption wavelength of the resin film held at 85°C and 85% relative humidity for 120 hours, λ f is the maximum absorption wavelength at this time, A i is the transmittance at the maximum absorption wavelength of the resin film before being held at 85°C and 85% relative humidity for 120 hours, and λ i is the maximum absorption wavelength at this time.

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

[0179]

Table 3

[0180] Comparing the results of Tables 1 to 3 and Figures 4 to 7, it can be seen that the compounds of the examples and the compounds of the comparative examples have similar spectroscopic properties of the compounds themselves, but show a large difference in the absorption properties when applied to the resin film and / or the absorption properties after the high-temperature and high-humidity evaluation. From such a point, it can be confirmed that the said compound can absorb light in the infrared region due to its unique structure, and at the same time has excellent heat resistance and can effectively form a resin film with excellent performance.

Explanation of symbols

[0181] 100 Substrate 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 hydroxyl group, or a cyano group; R １ ~R ２８ At least one of is deuterium.

2. The compound according to claim 1, having a deuterium substitution rate of 10% or more.

3. The compound according to 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. 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 held 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 held 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 sides 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.

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