Organic dye compound, optical film, and display device

Abstract

The invention discloses an organic dye compound, an optical film and a display device, and the organic dye compound has a structure as shown in a formula I. According to the application, a fluorine-containing substituent group with low molecular weight is introduced into a phthalocyanine compound, so that the organic dye compound has low molecular weight, good solubility and excellent optical performance.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of display, in particular to an organic dye compound, an optical film and a display device. BACKGROUND

[0002] Traditional methods for improving the solubility of phthalocyanine organic dyes mainly include introducing high molecular weight steric groups or long alkyl chains into phthalocyanine compounds to achieve solubilization effect, but this method will significantly increase the molecular weight of the organic dye, resulting in a decrease in the molar absorption coefficient of the organic dye under the same mass concentration, affecting the light absorption performance of the organic dye. SUMMARY

[0003] The present application provides an organic dye compound, an optical film and a display device, which have low molecular weight, good solubility and excellent optical performance.

[0004] The present application provides an organic dye compound, which has a structure shown in Formula I:

[0005]

[0006] wherein R1, R2, R3, R4, R5, R6, R7, R8 are selected from substituents having 1 to 10 carbon atoms, at least one of R1, R2, R3, R4, R5, R6, R7, R8 contains a fluorine atom, and the total number of fluorine atoms on adjacent two carbon atoms in R1, R2, R3, R4, R5, R6, R7 or R8 is less than 5.

[0007] M is selected from a divalent metal atom, a trivalent metal atom-ligand or a tetravalent metal atom-ligand.

[0008] In some embodiments, R1, R2, R3, R4, R5, R6, R7, R8 are selected from alkyl groups having 4 to 10 carbon atoms.

[0009] wherein one or more -H in R1, R2, R3, R4, R5, R6, R7, R8 is not substituted or is substituted with -N(R9)2;

[0010] one or more -CH2- in R1, R2, R3, R4, R5, R6, R7, R8 is not substituted or is substituted with at least one of -O-, -NR9-, -CO-, -C(O)O-, -OC(O)-, and R9 is selected from hydrogen, an alkyl group having 1 to 10 carbon atoms or an alkylene group having 1 to 10 carbon atoms.

[0011] In some embodiments, R1, R2, R3, R4, R5, R6, R7 or R8 contains a fluorine atom on any carbon atom, wherein the substituents on adjacent two carbon atoms are not all fluorine atoms at the same time.

[0012] In some embodiments, R1, R2, R3, R4, R5, R6, R7, or R8comprises 1 to 3 fluorine atoms.

[0013] In some embodiments, R1, R2, R3, R4, R5, R6, R7, R8is selected from the structure shown in Formula II:

[0014]

[0015] wherein m is selected from 1, 2, 3, 4, 5, 6, or 7;

[0016] n is selected from 1, 2, or 3.

[0017] In some embodiments, R1, R2, R3, R4, R5, R6, R7, and R8are selected from the same substituent.

[0018] In some embodiments, the divalent metal atom comprises Co, Ni, Cu, Zn, Pd, or Mg, the trivalent metal atom-ligand comprises Fe-Cl, Mn-Cl, or In-Cl, and the tetravalent metal atom-ligand comprises V=O.

[0019] In some embodiments, the maximum absorption wavelength λ max of the organic dye compound is in the range of 743 nm to 791 nm.

[0020] The present application also provides an optical film prepared from the organic dye compound as described above.

[0021] The present application also provides a display device comprising a display panel and an optical film as described above, the optical film being located on one side of the display panel.

[0022] The application provides an organic dye compound, an optical film and a display device. The organic dye compound is a metal phthalocyanine complex. R1, R2, R3, R4, R5, R6, R7 and R8 are introduced into benzene rings of the phthalocyanine structure respectively, the groups are selected from substituents with 1-10 carbon atoms, and at least one of the groups contains fluorine atoms, and the total number of fluorine atoms on adjacent two carbon atoms in R1, R2, R3, R4, R5, R6, R7 or R8 is less than 5. The number of carbon atoms of R1, R2, R3, R4, R5, R6, R7 and R8 is less than 10, the molecular weight is low, the high molar absorption coefficient of the organic dye is ensured, a limited amount of fluorine atoms is introduced, the solubility of the organic compound is further increased, and the environmental protection requirement is ensured. The synergistic effect of the low molecular weight substituent group and the fluorine atom is utilized, the organic dye compound with the low molecular weight, the good solubility and the excellent optical performance can be obtained, and the optical film and the display device prepared based on the organic dye compound have excellent optical performance. BRIEF DESCRIPTION OF DRAWINGS

[0023] In order to more clearly illustrate the technical solutions in the embodiments of the application, the drawings needed in the embodiment description will be briefly introduced. Obviously, the drawings in the following description are only some embodiments of the application, and other drawings can be obtained by those skilled in the art without creative effort.

[0024] Figure 1 The ultraviolet-visible absorption spectrum of the organic dye compounds I-1-1, I-1-2, I-1-3 and Ref-1 provided in the embodiments of the application is shown in the figure.

[0025] Figure 2 The structural schematic diagram of a display device provided in the embodiments of the application is shown in the figure.

[0026] Explanation of reference signs:

[0027] 10, display device; 100, display panel; 200, optical film. DETAILED DESCRIPTION

[0028] The technical solutions in the embodiments of the application will be described clearly and completely in combination with the drawings in the embodiments of the application. Obviously, the described embodiments are only some of the embodiments of the application, not all the embodiments. Based on the embodiments in the application, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of the application.

[0029] The application provides an organic dye compound, which has the structure shown in formula I.

[0030]

[0031] wherein R1, R2, R3, R4, R5, R6, R7, R8 are selected from substituents having 1 to 10 carbon atoms, at least one of R1, R2, R3, R4, R5, R6, R7, R8 contains a fluorine atom, and the total number of fluorine atoms on adjacent two carbon atoms in R1, R2, R3, R4, R5, R6, R7 or R8 is less than 5;

[0032] M is selected from a divalent metal atom, a trivalent metal atom-ligand or a tetravalent metal atom-ligand.

[0033] wherein the divalent metal atom includes Co, Ni, Cu, Zn, Pd or Mg, the trivalent metal atom-ligand includes Fe-Cl, Mn-Cl or In-Cl, and the tetravalent metal atom-ligand includes V=O. Preferably, M is selected from Cu, Zn, Pd or V=O, and the organic dye compound has better solubility, better stability, weaker absorption in the visible region (i.e. does not block visible light) and the like when the above metal or metal-ligand is selected.

[0034] In the present application, the maximum absorption wavelength λ max of the organic dye compound is in the range of 743 nm to 791 nm, i.e. the organic dye compound represented by formula I can absorb light in the near-infrared band, and is a near-infrared light absorbing dye. In the structure of the organic dye compound, the phthalocyanine molecule is a macrocyclic conjugated system composed of 18 π electrons, and the basic structure is a planar macrocycle formed by connecting four isoindole rings through imine bridges. This highly delocalized conjugated system makes the energy level difference between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of the molecule smaller, and the corresponding electronic transition (π-π* transition) energy lower, so that the absorption wavelength is easily red-shifted to the near-infrared region. In the structure of the organic dye compound of formula I of the present application, R1 and R2, R3 and R4, R5 and R6, R7 and R8 are respectively located at the 4th and 7th positions of the isoindole ring (with N of the isoindole ring as the 1st position), and when R1, R2, R3, R4, R5, R6, R7, R8 are respectively located at the positions shown in the structure of formula I, it is determined that the organic dye compound absorbs light in the near-infrared band, and the maximum absorption wavelength λ max is in the range of 743 nm to 791 nm, and the other substituents on the isoindole ring except R1, R2, R3, R4, R5, R6, R7, R8 are hydrogen, which can avoid the increase of the molecular weight of the organic dye compound. Therefore, the organic dye compound of formula I of the present application has a relatively low molecular weight while ensuring the absorption of light in the near-infrared band.

[0035] In addition, the central metal atom M is coordinated with the four nitrogen atoms of the phthalocyanine ring, significantly affects the electronic structure of the macrocycle through charge transfer, coordination bond strength, etc., can change the absorption wavelength, and the substituents R1-R8 on the phthalocyanine ring change the conjugated electron density of the macrocycle through electronic effect or steric effect, which can indirectly adjust the HOMO-LUMO energy level difference, so that the maximum absorption wavelength of the organic dye compound represented by formula I can be adjusted within a certain range to meet the application of different scenes. In summary, the organic dye compound represented by formula I adjusts the HOMO-LUMO energy level difference or the charge transfer transition energy through the combined action of the inherent π-π* transition characteristics of the phthalocyanine macrocycle conjugated system, the regulation of the central metal atom M, and the position selection of the substituents R1-R8 on the phthalocyanine ring, so that its absorption wavelength falls in the near-infrared region, especially the maximum absorption wavelength λ max in the range of 743 nm to 791 nm.

[0036] In some embodiments, R1, R2, R3, R4, R5, R6, R7, R8 are selected from alkyl groups having 4 to 10 carbon atoms, wherein one or more -H in R1, R2, R3, R4, R5, R6, R7, R8 is not substituted or substituted with -N(R9)2, one or more -CH2- in R1, R2, R3, R4, R5, R6, R7, R8 is not substituted or substituted with at least one of -O-, -NR9-, -CO-, -C(O)O-, -OC(O)-, R9 is selected from hydrogen, alkyl group having 1 to 10 carbon atoms or alkylene group having 1 to 10 carbon atoms.

[0037] In the present embodiment, R1-R8 are selected from low molecular weight substituent groups having 4 to 10 carbon atoms, which will not significantly increase the molecular weight of the organic dye compound, avoiding the problem of reducing the molar absorption coefficient of the organic dye caused by introducing a group with too large molecular weight, affecting the light absorption performance of the organic dye compound. At the same time, when the substituents R1-R8 are selected from the above groups, the electronic effect or steric effect of the molecule can be changed according to the type of the selected group (such as electron-donating group or electron-withdrawing group, etc.), molecular size, to adjust the absorption wavelength of the organic dye compound, so that it can be applied to different scene requirements.

[0038] In some embodiments, any carbon atom in R1, R2, R3, R4, R5, R6, R7, or R8 can contain a fluorine atom, that is, the fluorine atom can be located on any carbon atom of R1, R2, R3, R4, R5, R6, R7, or R8 to improve the solubility of the organic dye compound.

[0039] The total number of fluorine atoms on adjacent two carbon atoms in R1, R2, R3, R4, R5, R6, R7or R8is less than 5, but the substituents on adjacent two carbon atoms are not all fluorine atoms at the same time, for example, a group containing -CF2CF2- or -CF2CF3cannot appear in R1, R2, R3, R4, R5, R6, R7and R8to avoid affecting the stability of the organic dye compound, causing the dissolution regulation of the organic dye compound to fail, the synthesis and purification to be difficult, and other problems, and to avoid excessive fluorine content to ensure environmental protection requirements.

[0040] In some embodiments, R1, R2, R3, R4, R5, R6, R7or R8contains 1 to 3 fluorine atoms, that is, the number of fluorine atoms contained in R1, R2, R3, R4, R5, R6, R7and R8is less than or equal to 3. Because, when the fluorine atoms contained in R1, R2, R3, R4, R5, R6, R7or R8are too much, it will cause the organic dye compound to be difficult to purify, and cause the molecular weight of the organic dye compound to increase, and reduce the molar absorption coefficient of the organic dye. By introducing the solubilizing chain R1-R8 containing a limited number of fluorine atoms into the phthalocyanine molecule, the present application successfully prepared a new type of organic dye compound formula I with low molecular weight, good solubility and excellent optical performance. This clever design skillfully utilizes the solubilizing effect of fluorine atoms, while avoiding a sharp increase in molecular weight, thereby ensuring a high molar absorption coefficient of the organic dye. At the same time, through the modification mode of low molecular weight + low fluorine substitution, the solubility is improved while fully meeting the current environmental protection regulations, and has great application prospect.

[0041] In some embodiments, R1, R2, R3, R4, R5, R6, R7, R8is selected from the structure shown in formula II:

[0042]

[0043] wherein m is selected from 1, 2, 3, 4, 5, 6 or 7;

[0044] n is selected from 1, 2 or 3.

[0045] In the present embodiment, R1, R2, R3, R4, R5, R6, R7, R8is selected from an alkoxy group having 4 to 10 carbon atoms, and the oxygen atom is connected to the phthalocyanine ring, because the oxygen atom is easier to combine with the phthalocyanine ring, so that the organic dye compound is easier to synthesize and prepare, and the preparation method and process can be simplified.

[0046] At the same time, the terminal carbon atom of R1, R2, R3, R4, R5, R6, R7, R8contains 1 to 3 fluorine atoms, because the reagent with fluorine atoms at the terminal is easier to obtain and has lower cost, which is conducive to reducing the preparation cost of the organic dye compound, and simplifying the process.

[0047] And, R1, R2, R3, R4, R5, R6, R7 or R8 is a linear substituent, and when R1, R2, R3, R4, R5, R6, R7 or R8 contains a long alkyl chain, the solubilizing effect can be further improved, and the solubility of the organic dye compound is improved.

[0048] In some embodiments, R1, R2, R3, R4, R5, R6, R7 and R8 are selected from the same substituent. When R1, R2, R3, R4, R5, R6, R7 and R8 are the same, R is used instead of R1, R2, R3, R4, R5, R6, R7 and R8, and the structure represented by formula I can be represented as:

[0049]

[0050] wherein the selection range of R is the same as that of R1, R2, R3, R4, R5, R6, R7 and R8, which will not be repeated here.

[0051] When R1, R2, R3, R4, R5, R6, R7 and R8 are the same, the organic dye compound I-1 has a symmetrical structure, which is beneficial to reduce the "imbalance effect" between molecules, improve the solvation efficiency, and further improve the solubility of the organic dye compound.

[0052] The application also provides a preparation method of an organic dye compound, comprising:

[0053] 1. Preparation reaction path of the organic dye compound:

[0054]

[0055] wherein,

[0056] (1) In the first step reaction:

[0057] The base can be an inorganic base or an organic base, the inorganic base can be at least one of sodium carbonate, potassium carbonate, potassium phosphate, sodium tert-butoxide, potassium tert-butoxide, and the organic base can be at least one of triethylamine, 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU);

[0058] The solvent can be at least one of acetonitrile, N,N-dimethylformamide (DMF), and dimethyl sulfoxide (DMSO);

[0059] The heating temperature is selected according to the solvent, and ranges from 70°C to 120°C.

[0060] (2) In the second step reaction:

[0061] The metal salt is an acetate or chloride salt of the corresponding metal, for example, M II (OAc)2or M II Cl2;

[0062] The base can be an inorganic base or an organic base, the inorganic base can be at least one of sodium carbonate, potassium carbonate, potassium phosphate, sodium tert-butoxide, potassium tert-butoxide, and the organic base can be at least one of triethylamine, 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

[0063] The solvent can be at least one of n-butanol, n-pentanol, and n-hexanol.

[0064] The heating temperature is selected according to the solvent and ranges from 100°C to 180°C.

[0065] 2. The preparation steps of the organic dye compound include:

[0066] (1) mixing 3,6-dihydroxyphthalonitrile, a halogenated alkane, a base, and a solvent, heating the mixture under nitrogen protection for 12 hours, and then separating and purifying to obtain an intermediate;

[0067] (2) mixing the intermediate, a metal salt, a base, and a solvent, heating the mixture under nitrogen protection for 24 hours, and then separating and purifying to obtain the organic dye compound.

[0068] In the present application, based on the above synthesis method, the maximum absorption wavelength of the organic dye compound can be adjusted by adjusting the groups M and R1, R2, R3, R4, R5, R6, R7, and R8 in the reactants, so that the organic dye compound can be applied to more scenarios.

[0069] The present application also provides an optical film prepared from the organic dye compound as described above. The optical film can absorb near-infrared light, and the maximum absorption wavelength λ max ranges from 743 nm to 791 nm. Specifically, the optical film can be used as a near-infrared filter film, and the optical film has excellent visible light transmittance while maintaining effective absorption in the near-infrared band.

[0070] In some embodiments, the material of the optical film includes a UV curing adhesive and the organic dye compound I as described above. The content of the organic dye compound I in the total amount of the UV curing adhesive and the organic dye compound I is 0.1 wt% to 2.0 wt%.

[0071] The UV curing adhesive can be an acrylic resin system UV curing adhesive, which includes a semi-cured resin, a monomer, a leveling agent, a dispersant, an initiator, and a solvent.

[0072] Specifically, the optical film can be obtained by dissolving the organic dye compound I in UV curing glue, then coating, leveling, drying, and UV curing.

[0073] The organic dye compound and the optical film of the present application are further described below through specific examples.

[0074] I. Synthesis of the organic dye compound

[0075] Example 1

[0076] Intermediate 1

[0077]

[0078] Synthesis of Intermediate 1: 3,6-dihydroxyphthalonitrile (10 mmol), 1-bromo-4-fluorobutane (25 mmol), potassium carbonate (40 mmol) and anhydrous DMF (50 mL) were mixed, the mixture was degassed and heated to 100°C and stirred for 12 h. After the reaction was cooled to room temperature, the mixture was poured into ice water, and the solid was precipitated. The filter cake was washed with water and methanol, and dried to obtain white powder product Intermediate 1 with a yield of 93%. Nuclear magnetic resonance hydrogen spectrum (H NMR, CDC13): 7.20 (s, 2H), 3.92 (t, 4H), 1.78 (m, 4H), 1.28 (m, 4H), 0.99 (t, 4H); mass spectrum: 309.34 [M+H+]; elemental analysis: C 61.89, H 5.95, O 10.41, N 9.11. 1 H NMR, CDC13): 7.20 (s, 2H), 3.92 (t, 4H), 1.78 (m, 4H), 1.28 (m, 4H), 0.99 (t, 4H); mass spectrum: 309.34 [M+H+]; elemental analysis: C 61.89, H 5.95, O 10.41, N 9.11.

[0079] Organic dye compound I-1-1

[0080]

[0081] Synthesis of organic dye compound I-1-1: Intermediate 1 (2 mmol), anhydrous copper chloride (0.75 mmol), DBU (2 mmol) and n-pentanol (10 mL) were mixed, the mixture was degassed and heated to 160°C and stirred for 24 h. After the reaction was cooled to room temperature, methanol was added to the mixture to precipitate the solid. The filter cake was washed with methanol to obtain the crude product. The crude product was further purified by column chromatography, concentrated and recrystallized to obtain green powder organic dye compound I-1-1 with a yield of 28%. Mass spectrum: 1297.88 [M+H+]; elemental analysis: C 58.90, H 5.83, O 10.12, N 8.72. UV-vis: λ max = 748 nm, where UV-vis represents ultraviolet-visible absorption spectrum.

[0082] Example 2

[0083] Organic dye compound I-1-2

[0084]

[0085] The synthesis method and reaction amounts of the organic dye compound I-1-2 were the same as those of the organic dye compound I-1-1 in Example 1, except that the reaction raw material anhydrous copper chloride was replaced with vanadium trichloride. The product was the black green solid organic dye compound I-1-2, with a yield of 24%. Mass spectrum: 1300.26 [M+]; elemental analysis: C 58.99, H 5.67, O 11.53, N 8.72. UV-vis: λ max = 791 nm.

[0086] Example 3

[0087] Intermediate 2

[0088]

[0089] The synthesis method and reaction amounts of the intermediate 2 were the same as those of the intermediate 1 in Example 1, except that the reaction raw material 1-bromo-4-fluorobutane was changed to 1-bromo-4,4,4-trifluorobutane. The product was the white solid intermediate 2, with a yield of 90%. Nuclear magnetic hydrogen spectrum (1H NMR, CDC13): 7.21 (s, 2H), 3.96 (t, 4H), 1.85 (m, 4H), 1.36 (t, 4H); mass spectrum: 381.30 [M+H+]; elemental analysis: C 50.20, H 3.79, O 8.54, N 7.42. 1

[0090] Organic dye compound I-1-3

[0091]

[0092] The synthesis method and reaction amounts of the organic dye compound I-1-3 were the same as those of the organic dye compound I-1-1 in Example 1, except that the reaction raw material intermediate 1 was changed to intermediate 2. The product was the green solid organic dye compound I-1-3, with a yield of 32%. Mass spectrum: 1584.71 [M+]; elemental analysis: C 48.56, H 3.62, O 8.24, N 7.11. UV-vis: λ max = 743 nm.

[0093] Comparative Example 1

[0094] Organic compound Ref-1

[0095] ​

[0096] A mixture of 3,6-dibutyloxy phthalonitrile (3 mmol), cuprous chloride (1.4 mmol), DBU (10 mmol) and n-pentanol (5 mL) was stirred at 140°C for 10 h after degassing. After the reaction was cooled to room temperature, methanol was added to the mixture to precipitate the solid. The filter cake was washed with methanol to obtain the crude product. The crude product was purified by column chromatography, concentrated and recrystallized to obtain a green powder. UV-vis: λ max = 752 nm.

[0097] Comparative Example 2

[0098] Organic compound Ref-2

[0099]

[0100] A mixture of 3,6-dibutyloxy phthalonitrile (3 mmol), cuprous chloride (1.4 mmol), DBU (10 mmol) and n-pentanol (5 mL) was stirred at 140°C for 10 h after degassing. After the reaction was cooled to room temperature, methanol was added to the mixture to precipitate the solid. The filter cake was washed with methanol to obtain the crude product. The crude product was purified by column chromatography, concentrated and recrystallized to obtain a green powder. UV-vis: λ max = 764 nm.

[0101] II. Solubility test of organic dye compounds

[0102] A certain mass of an organic dye compound was placed in a bottle, and a solvent was gradually added and shaken until the dye was completely dissolved, and was classified according to the solubility. The solubility test results of the organic dye compounds are shown in Table 1.

[0103] Table 1

[0104]

[0105] Wherein, o represents solubility ≥ 5 mg / mL, Δ represents solubility 1-5 mg / mL, and x represents solubility ≤ 1 mg / mL.

[0106] As can be seen from the results in Table 1, the solubility of the organic dye compounds I-1-1, I-1-2 and I-1-3 of the present application is obviously better than that of the organic dye compound Ref-1 of Comparative Example 1 and the organic dye compound Ref-2 of Comparative Example 2. By introducing a low-molecular-weight R group and 1 to 3 fluorine atoms into the R group in the organic dye compounds of the present application, the solubility can be effectively improved by introducing a solubilizing chain R containing a limited number of fluorine atoms in the phthalocyanine molecule without significantly increasing the molecular weight.

[0107] III. Preparation of optical film and optical performance test

[0108] (1) Preparation method of optical film

[0109] 0.1wt%-2.0wt% of organic dye compound I-1-1 was dissolved in UV curing glue, and then optical film 1 was obtained after coating, leveling, drying and UV curing. The UV curing glue includes semi-cured resin, monomer, leveling agent, dispersing agent, initiator and solvent, the semi-cured resin can be acrylic resin prepolymer (KAYARAD, UA-306H), the monomer can be dipentaerythritol hexaacrylate, the leveling agent can be BYK-3931P (BYK-chemie), the dispersing agent can be BYK-2013 (BYK-chemie), and the solvent can be ethyl acetate.

[0110] Similarly, using the above method, the organic dye compound I-1-2 was used to replace the above organic dye compound I-1-1 to obtain optical film 2; the organic dye compound I-1-3 was used to replace the above organic dye compound I-1-1 to obtain optical film 3; the compound Ref-1 of Comparative Example 1 was used to replace the above organic dye compound I-1-1 to obtain optical film 4; the compound Ref-2 of Comparative Example 2 was used to replace the above organic dye compound I-1-1 to obtain optical film 5.

[0111] (2) Optical performance test

[0112] The above optical film 1, optical film 2, optical film 3, optical film 4 and optical film 5 were tested for ultraviolet-visible absorption spectrum on an ultraviolet-visible spectrophotometer (instrument model Shimidzu UV-2600) to obtain the maximum absorption wavelength (λ max ), and the related test results are shown in Table 2 and Figure 1 .

[0113] Table 2

[0114]

[0115] Note: The maximum absorption values in Table 2 are the absorption values after subtracting the absorption value of the coated substrate (i.e. the baseline, about 0.04).

[0116] As shown in Table 2 and Figure 1 , the maximum absorption wavelengths of the organic dye compound I-1-1, the organic dye compound I-1-2 and the organic dye compound I-1-3 are all in the range of 743nm-791nm, which proves that the organic dye compound I-1-1, the organic dye compound I-1-2 and the organic dye compound I-1-3 can absorb light in the near-infrared light band, and have excellent optical performance.

[0117] As shown in Table 2 andFigure 1 It can be seen that the maximum absorption values of the organic dye compound I-1-1, the organic dye compound I-1-2 and the organic dye compound I-1-3 are 0.244, 0.208 and 0.257 respectively, all of which have relatively high maximum absorption values, and the above maximum values are positively correlated with the molar absorption coefficient, which reflects that the organic dye compound of the present application still ensures a relatively high molar absorption coefficient while improving the solubility (the maximum absorption value of a material with a large molecular weight is usually lower, slightly higher than the baseline).

[0118] The present application also provides a display device 10, please refer to Figure 2 The display device 10 comprises a display panel 100 and an optical film 200 as described above, and the optical film 200 is arranged on one side of the display panel 100.

[0119] The display panel 100 can be an OLED display panel, a liquid crystal display panel, etc., but is not limited thereto.

[0120] In the present application, the optical film 200 is arranged on the light-emitting side of the display panel 100, and the optical film 200 comprises an organic dye compound selected from the above formula I, so it can selectively absorb the maximum absorption wavelength λ max The near-infrared light is between 743 nm and 791 nm.

[0121] The display device 10 of the present application can be a mobile phone, a tablet, a computer, a smart display and an outdoor display, etc., but is not limited thereto.

[0122] The present application provides an organic dye compound, an optical film and a display device. The organic dye compound provided by the present application is a metal phthalocyanine complex, wherein R1, R2, R3, R4, R5, R6, R7 and R8 groups are introduced on the benzene ring of the phthalocyanine structure, respectively. These groups are selected from substituents with 1 to 10 carbon atoms, and at least one contains a fluorine atom. The total number of fluorine atoms on adjacent two carbon atoms in R1, R2, R3, R4, R5, R6, R7 or R8 is less than 5. The number of carbon atoms of the R1, R2, R3, R4, R5, R6, R7 and R8 groups introduced by the present application is less than 10, which ensures a high molar absorption coefficient of the organic dye. At the same time, a limited amount of fluorine atoms is introduced, which further increases the solubility of the organic compound and also ensures the environmental protection requirements. The present application utilizes the synergistic effect of low molecular weight substituent groups and fluorine atoms to obtain an organic dye compound with low molecular weight, good solubility and excellent optical performance. The optical film and the display device prepared based on the organic dye compound both have excellent optical performance.

[0123] Any combination of the technical features in the above-described embodiments can be made, and for the sake of brevity, not all possible combinations are described, however, as long as there is no conflict, any combination of the technical features should be considered within the scope of the present disclosure.

[0124] The above-described embodiments only express several implementation manners of the present application, and the description is relatively specific and detailed, but it should not be understood as a limitation on the patent scope of the present application. It should be pointed out that, for ordinary skilled persons in the art, several modifications and improvements can be made without departing from the concept of the present application, and these all belong to the protection scope of the present application. Therefore, the patent protection scope of the present application should be subject to the appended claims.

Claims

1. An organic dye compound, characterized in that, The organic dye compound has the structure shown in Formula I: R1, R2, R3, R4, R5, R6, R7, and R8 are selected from substituents having 1 to 10 carbon atoms, at least one of R1, R2, R3, R4, R5, R6, R7, and R8 contains a fluorine atom, and the total number of fluorine atoms on two adjacent carbon atoms in R1, R2, R3, R4, R5, R6, R7, or R8 is less than 5. M is selected from divalent metal atoms, trivalent metal atoms-ligands, or tetravalent metal atoms-ligands.

2. The organic dye compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, and R8 are selected from alkyl groups having 4 to 10 carbon atoms; Among them, one or more of -H in R1, R2, R3, R4, R5, R6, R7, and R8 are not substituted, or are substituted by -N(R9)2; One or more of R1, R2, R3, R4, R5, R6, R7, and R8 are not substituted, or are substituted by at least one of -O-, -NR9-, -CO-, -C(O)O-, and -OC(O)-, wherein R9 is selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, or an alkylene group having 1 to 10 carbon atoms.

3. The organic dye compound according to claim 2, characterized in that, Any carbon atom in R1, R2, R3, R4, R5, R6, R7, or R8 contains a fluorine atom, wherein the substituents on two adjacent carbon atoms are not all fluorine atoms at the same time.

4. The organic dye compound according to claim 3, characterized in that, R1, R2, R3, R4, R5, R6, R7, or R8 contain 1 to 3 fluorine atoms.

5. The organic dye compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, and R8 are selected from the structure shown in Equation II: Where m is selected from 1, 2, 3, 4, 5, 6 or 7; n is selected from 1, 2, or 3.

6. The organic dye compound according to claim 5, characterized in that, R1, R2, R3, R4, R5, R6, R7, and R8 are selected from the same substituents.

7. The organic dye compound according to claim 1, characterized in that, The divalent metal atoms include Co, Ni, Cu, Zn, Pd, or Mg; the trivalent metal atom-ligand includes Fe-Cl, Mn-Cl, or In-Cl; and the tetravalent metal atom-ligand includes V=O.

8. The organic dye compound according to any one of claims 1 to 7, characterized in that, The maximum absorption wavelength λ of the organic dye compound max The range is 743nm to 791nm.

9. An optical film, characterized in that, The optical film is prepared from the organic dye compound as described in any one of claims 1 to 8.

10. A display device, characterized in that, It includes a display panel and an optical film as described in claim 9, wherein the optical film is located on one side of the display panel.

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