Organic compound, optical film, and display device

Abstract

The invention relates to an organic compound, an optical film and a display device, and the organic compound has a structure as shown in a formula I. The organic compound provided by the invention can selectively absorb cyan light and can be applied to the optical film to absorb cyan stray light of a non-display wave band emitted by a display panel so as to reduce color crosstalk and improve the display quality. And the color purity and the display contrast of the display device are improved.

Description

Technical Field

[0001] The present application relates to the field of displays, and particularly to an organic compound, an optical film, and a display device. Background Art

[0002] A color optical film (OCF) is a layer of film material with specific optical absorption function disposed on the surface of an optical element, used to reduce the ambient light reflection of a display panel, improve the transmittance of the emission spectrum, and enhance the visibility of the screen. The color optical film can be used to replace a polarizer and has great development potential in the Polarizer less (POL-Less) technology.

[0003] The color optical film can replace the polarizer and selectively absorb ambient light. The color optical film can absorb light in non-display bands to reduce the reflectance of ambient light, and at the same time transmit light in the display band, increasing the transmittance to 70% - 90%, which can reduce power consumption and increase the lifespan of the light-emitting device.

[0004] In order to absorb light in non-display bands, that is, light other than red (R), green (G), and blue (B), the color optical film needs to contain dyes that absorb stray light such as cyan light (light in the band between G and B) and yellow-orange light (light in the band between R and G). Since there are differences in the light-emitting materials of different display panels, the maximum absorption wavelength λ max and the full width at half maxima (FWHM) will also vary. Therefore, the position of the maximum absorption wavelength of the dye needs to be adjusted according to different application scenarios. However, in the prior art, there are few choices of dyes that absorb cyan light, which limits the application of color optical films in the display field. Summary of the Invention

[0005] The present application provides an organic compound, an optical film, and a display device. The organic compound can selectively absorb cyan light and can be applied to an optical film to absorb stray cyan light in non-display bands emitted from a display panel, so as to reduce color crosstalk and improve the color purity and display contrast of the display device.

[0006] The present application provides an organic compound having the structure shown in Formula I:

[0007]

[0008] Wherein, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7Selected from hydrogen or a substituent having 1 to 10 carbon atoms;

[0009] M represents a divalent transition metal atom.

[0010] In some embodiments, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is selected from hydrogen or an alkyl group having 1 to 10 carbon atoms, wherein one or more of -H in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is not substituted, or is substituted by -N(R 0 )2, -COOH, one or more of -CH2- in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is not substituted, or is substituted by -O-, -NR 0 -, -CO-, -C(O)O-, -OC(O)-, and R 0 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, R 1 , R 3 , R 5 , R 7 is selected from alkyl groups having 1 to 5 carbon atoms, and R 4 is selected from hydrogen or an alkyl group having 1 to 5 carbon atoms.

[0012] In some embodiments, at least one of R 2 and R 6 contains an ester group or a carboxyl group.

[0013] In some embodiments, the organic compound has the structure shown in Formula I-1:

[0014]

[0015] wherein, R 4 , R 8 is selected from hydrogen or an alkyl group having 1 to 5 carbon atoms;

[0016] n is selected from 0, 1, 2, 3, 4, or 5.

[0017] In some embodiments, M is selected from Co, Ni, Cu, Zn, Pd, or Mg.

[0018] In some embodiments, the maximum absorption wavelength λ of the organic compound max ranges from 498 nm to 502 nm, and the absorption full width at half maximum of the organic compound is less than or equal to 40 nm.

[0019] This application also provides an optical film, which includes a first light-absorbing dye, and the first light-absorbing dye includes the organic compound as described above.

[0020] In some embodiments, the optical film further includes a second light-absorbing dye, and the absorption wavelength of the second light-absorbing dye is in the range of 570 nm to 620 nm.

[0021] This application also provides a display device, which includes a display panel and the optical film as described above, and the optical film is disposed on the light-emitting side of the display panel.

[0022] This application provides an organic compound, an optical film, and a display device. The organic compound provided by this application includes a conjugate system formed by bonding two methylene dipyrrole units to a metal M through a coordination bond as a main structure, so it has excellent stability, and a benzene ring is connected to the methylene group, that is, benzene ring groups are introduced at the upper and lower opposite ends of the main structure respectively, further expanding the conjugate structure, causing the absorption of the organic compound to redshift, and enabling it to absorb cyan light. At the same time, by selecting the R 1 -R 7 groups and the metal M, the maximum absorption wavelength λ max and the absorption full width at half maximum FWHM of the organic compound can be adjusted to realize the regulation of the light absorption performance of the organic compound, so that the organic compound can selectively absorb cyan light in the band between green light and blue light, and has a narrow absorption full width at half maximum and excellent optical properties. The organic compound of this application is applied in the optical film, which can effectively absorb cyan stray light in the non-display band, reduce color crosstalk, and further improve the color purity and display contrast of the display device. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 is the ultraviolet-visible absorption spectrum of the organic compound I-1-1 provided by the embodiment of this application;

[0024] Figure 2 is the ultraviolet-visible absorption spectrum of the organic compound I-1-2 provided by the embodiment of this application;

[0025] Figure 3The ultraviolet-visible absorption spectrum of organic compound I-1-3 provided by the embodiments of the present application;

[0026] Figure 4 The structural schematic diagram of a display device provided by the embodiments of the present application.

[0027] Explanation of reference numerals:

[0028] 10. Display device; 100. Display panel; 110. Array substrate; 120. Light-emitting device layer; 130. Encapsulation layer; 200. Optical film. Detailed implementation manners

[0029] Next, the technical solutions in the embodiments of the present application will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without making creative efforts belong to the scope of protection of the present application. In addition, it should be understood that the specific implementation manners described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, unless otherwise stated, the orientation terms such as "upper" and "lower" usually refer to the upper and lower in the actual use or working state of the device, specifically the drawing direction in the accompanying drawings. In the present application, "optionally", "optional", "optional" mean that it can be there or not, that is, it refers to any one of the two parallel options of "yes" or "no". If there are multiple "optional" in a technical solution, without special instructions and without conflict or mutual restriction relationship, each "optional" is independent. In the present application, for the technical features described in an open-ended manner, it includes the closed technical solutions composed of the listed features, and also includes the open technical solutions of the listed features.

[0030] The present application provides an organic compound, and the organic compound has the structure shown in Formula I:

[0031]

[0032] Wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are selected from hydrogen or substituents having 1 to 10 carbon atoms;

[0033] M is selected from divalent transition metal atoms.

[0034] The organic compound provided by this application is a light-absorbing dye based on an organometallic complex. The main structure of this organic compound is a conjugated system formed by two methylene dipyrrole units and metal M. Among them, the nitrogen atoms in the methylene dipyrrole units are bonded to metal M through coordination bonds to form a metal complex structure, endowing this organic compound with a large conjugated system and thus excellent stability. At the same time, a benzene ring is connected to the methylene group in the methylene dipyrrole unit, further expanding the conjugated structure, causing a red shift in the absorption of the organic compound, enabling this organic compound to have a unique absorption spectrum and be able to absorb cyan light. In addition, in this application, by selecting the R 1 -R 7 groups on the methylene dipyrrole unit of this organic compound, the maximum absorption wavelength λ max and the full width at half maximum FWHM of the absorption can be adjusted, realizing the regulation of the light absorption performance of this organic compound, enabling this organic compound to selectively absorb cyan light in the wavelength range between green light and blue light, having a narrow full width at half maximum of absorption, and excellent optical properties.

[0035] In some embodiments, the range of the maximum absorption wavelength λ max of the organic compound is 498 nm to 502 nm. For example, the maximum absorption wavelength λ max of the organic compound can be selected as 498 nm, 499 nm, 500 nm, 501 nm, 502 nm. When the maximum absorption wavelength λ max of the organic compound in this application is within the above range, it has a specific absorption spectrum and can absorb cyan stray light with λ max ranging from 498 nm to 502 nm.

[0036] The full width at half maximum FWHM of the absorption of the organic compound in this application is less than or equal to 40 nm. Further, the range of the full width at half maximum FWHM of the absorption of the organic compound is 30 nm to 40 nm. For example, the full width at half maximum FWHM of the absorption of the organic compound can be selected as 30 nm, 31 nm, 32 nm, 33 nm, 34 nm, 35 nm, 36 nm, 37 nm, 38 nm, 39 nm, 40 nm. Because when the full width at half maximum of the absorption is too large, the organic compound will absorb part of the green light and blue light, resulting in a decrease in the light intensity and color purity of the green light and blue light emitted during display. The organic compound in this application has a narrow full width at half maximum of the absorption, can more precisely absorb cyan stray light in the wavelength range between green light and blue light, reduce the absorption of green light and blue light, make the boundary between green light and blue light clearer, improve the utilization rate of green light and blue light, and is more conducive to improving the color purity and contrast of the display.

[0037] In this application, R 1 、R 2 、R 3 、R4 , R 5 , R 6 , R 7 is selected from hydrogen or a substituent having 1 to 10 carbon atoms. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 It is necessary to select a group with an appropriate carbon chain length, that is, a group with an appropriate molecular weight, to meet the requirements for solubility and purification during the preparation of the organic compound. Because when R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 the selected group has too long a carbon chain, the organic compound or its precursor will be in the form of a viscous oil rather than a solid powder, which is not conducive to the purification during the preparation process and the preparation of organic compound I. When R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 When the substituents within the above range are selected, the molecular weight of the substituents is appropriate, making the organic compound have good solubility and being in powder form, which is easy for purification and preparation.

[0038] Furthermore, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is selected from hydrogen or an alkyl group having 1 to 10 carbon atoms, where one or more -H in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is not substituted, or is substituted by -N(R 0 )2, -COOH, and one or more -CH2- in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is not substituted, or is substituted by -O-, -NR0 -CO-, -C(O)O-, -OC(O)-substituted; wherein R 0 is selected from hydrogen, an alkyl group having 1 to 10 carbon atoms or an alkylene group having 1 to 10 carbon atoms.

[0039] In some embodiments, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is selected from hydrogen or a substituent having 1 to 5 carbon atoms. When R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 selects substituents within the above range, the molecular weight of the substituents is more appropriate, and it is easier to prepare, and at the same time, it is more conducive to purification treatment.

[0040] Furthermore, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is selected from hydrogen or an alkyl group having 1 to 5 carbon atoms, wherein one or more -H in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is not substituted, or is substituted by -N(R 0 )2, -COOH, and one or more -CH2- in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is not substituted, or is substituted by -O-, -NR 0 -, -CO-, -C(O)O-, -OC(O)-; wherein R 0 is selected from hydrogen, an alkyl group having 1 to 5 carbon atoms or an alkylene group having 1 to 5 carbon atoms.

[0041] In some embodiments, R 1 , R 7Selected from alkyl groups having 1 to 5 carbon atoms. As shown in the structure of Formula I, the groups R 1 and R 7 are in close positions. When the groups at the positions of R 1 and R 7 are too small, the overall structure of the organic compound tends to be planar, and it is easy to stack and aggregate between molecules, and the material is difficult to disperse in the solvent, resulting in a decrease in the solubility of the organic compound. Therefore, in this embodiment, R 1 and R 7 do not select hydrogen, but preferably an alkyl group with a larger molecular weight relative to hydrogen. However, the groups at the positions of R 1 and R 7 should not be too large either. When the groups at the positions of R 1 and R 7 are too large, a large steric hindrance will be formed, and more drastic reaction conditions are required during the metallization reaction of the organic compound, such as higher reaction temperature, longer reaction time, etc., which will lead to an increase in production cost. Therefore, in this embodiment, R 1 and R 7 do not select alkyl groups with more than 5 carbon atoms. Considering all aspects, it is preferable that R 1 and R 7 are selected from alkyl groups having 1 to 5 carbon atoms. On the one hand, the appropriate steric hindrance of the groups is beneficial to the interlacing between the planes where the two methylene dipyrrole units connected to M are located, that is, the two methylene dipyrrole units connected to M are not coplanar, avoiding the overall structure of the organic compound from tending to be planar, and further avoiding stacking and aggregation between molecules, thereby improving solubility. On the other hand, the groups at the positions of R 1 and R 7 will not be too large, and drastic reaction conditions are not required, and the cost is low.

[0042] In some embodiments, R 3 and R 5 are selected from alkyl groups having 1 to 5 carbon atoms. When R 3 and R 5 select groups within this range, on the one hand, the molecular solubility can be improved and the purification treatment is facilitated, and on the other hand, the stability of the molecular structure can be ensured, and at the same time, the reaction can be simplified and the cost can be reduced.

[0043] In some embodiments, at least one of R 2 and R 6 contains an ester group or a carboxyl group. In this application, the conjugation effect and inductive effect of different groups selected for R 2 and R 6 are different, and the solubility and optical properties of the molecule can be adjusted. Among them, R 2 and R 6The selection of groups at the [position] has a relatively large impact on the optical properties of the organic compound, especially on the full width at half maximum (FWHM) of the absorption of the organic compound. When R 2 and R 6 are selected from an ester group or a carboxyl group, the organic compound has a narrow FWHM of absorption, meeting the requirement that the FWHM of absorption is less than or equal to 40 nm. For example, when R 2 and R 6 are selected from an ester group (such as -COOEt, etc.), the more ester groups in the organic compound, the smaller the FWHM of absorption. When R 2 and R 6 are selected from a carboxyl group, they have similar properties to the ester group.

[0044] In addition, in terms of the feasibility of the synthesis route and the convenience of synthesis, it is easier to realize the selection of alkyl groups or hydrogen for the groups at R 1 , R 3 , R 4 , R 5 , R 7 . When other groups are selected at R 1 , R 3 , R 4 , R 5 , R 7 , the synthesis is relatively difficult. When carboxyl groups or ester groups are selected at R 2 , R 6 , it is relatively easier to realize in terms of synthesis factors.

[0045] In some embodiments, the organic compound has the structure shown in Formula I-1:

[0046]

[0047] wherein, R 4 and R 8 are selected from hydrogen or alkyl groups having 1 to 5 carbon atoms;

[0048] n is selected from 0, 1, 2, 3, 4 or 5.

[0049] In this embodiment, when methyl groups are selected for the groups at R 1 , R 3 , R 5 , R 7 , it is easy to realize in synthesis, has a small steric hindrance, and has a high solubility; when hydrogen or alkyl groups having 1 to 5 carbon atoms are selected for R 4 , it is easy to realize in synthesis and has a high solubility; when groups with a carboxyl group or an ester group at the end are selected for R 2 , R 6 , it is easier to realize in terms of synthesis factors, has better optical properties, and has a smaller FWHM of absorption.

[0050] In some embodiments, the metal M is selected from Co, Ni, Cu, Zn, Pd, or Mg. In the organic compound structure of the present application, two methylene dipyrrole units are bonded to the metal M through a coordination bond, and the optical properties of the organic compound are also related to the selection of the central metal atom M. When M is selected from one of Co, Ni, Cu, Zn, Pd, or Mg, the organic compound can selectively absorb cyan light with a maximum absorption wavelength λ max between 498 nm and 502 nm, and has an optical property with a full width at half maximum absorption less than or equal to 40 nm. Further, when M is selected from Co or Zn, the organic compound has better optical properties.

[0051] In some embodiments, the organic compound I can be selected from any one of the following structures:

[0052]

[0053] The present application also provides a preparation method of an organic compound. The organic compound can be synthesized by an in-situ one-pot method, and the specific reaction path is as follows:

[0054]

[0055] The preparation steps of the organic compound include:

[0056] (1) Add the pyrrole derivative and the benzaldehyde derivative to dichloromethane for mixing, then add a trifluoroacetic acid (TFA) catalyst, and stir at room temperature to obtain a mixed solution containing intermediate A;

[0057] (2) Add 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) to the mixed solution containing intermediate A, and stir at room temperature to obtain a mixed solution containing intermediate B;

[0058] (3) Add methanol, triethylamine, and a metal salt (such as acetate M(OAc)2 or chloride M(Cl)2) to the mixed solution containing intermediate B, and stir under heating conditions to obtain a mixed solution containing organic compound I;

[0059] (4) Evaporate and concentrate, perform column chromatography, then concentrate, recrystallize, and filter the mixed solution containing organic compound I to obtain a powder of organic compound I.

[0060] The present application synthesizes the organic compound I by a one-pot synthesis method, which can effectively reduce the operation steps and reaction time, and is beneficial to large-scale synthesis and production.

[0061] In the present application, based on the above synthesis method, the groups R 1 , R 2 , R 3 , R4 , R 5 , R 6 , R 7 and metal M to adjust the maximum absorption wavelength and full width at half maximum of the organic compound, so that the organic compound can be applied to more scenarios.

[0062] This application also provides an optical film, which includes a first light-absorbing dye, and the first light-absorbing dye includes the organic compound I as described above.

[0063] The optical film further includes a polymer substrate, and the first light-absorbing dye is doped in the polymer substrate. Among them, the polymer can be an acrylic polymer. For example, it is an organic compound with a cross-linked structure polymerized from acrylic monomers, but not limited thereto. This polymer is used as the substrate of the optical film for film formation, and the organic compound I is doped in the polymer film material, so that the optical film has a specific light-absorbing effect.

[0064] In some embodiments, the optical film can be formed by curing a composition under light irradiation. Among them, the composition includes monomers of the polymer, organic compound I, a solvent, a photoinitiator, and functional additives (such as a leveling agent), etc. Specifically, the optical film can be formed by mixing acrylic monomers, organic compound I, a solvent, a photoinitiator, and functional additives, followed by coating and ultraviolet light curing. During the curing process, ultraviolet light initiates the initiator to generate free radicals, and the free radicals polymerize the acrylic monomers to form a cross-linked polymer network, thereby forming a solid optical film. Among them, the organic compound I is doped in the optical film, so that the optical film can absorb cyan light and the full width at half maximum of the absorption is less than or equal to 40 nm.

[0065] In some embodiments, organic compound I accounts for 0.1% to 2% of the total mass of the composition. Optionally, organic compound I accounts for 0.1%, 0.5%, 1%, 1.5%, 2%, etc. of the total mass of the composition. When the content of the organic compound is within the above range, the formed optical film has good optical effects.

[0066] The optical film of this application can replace the polarizer in the prior art. The optical film can absorb visible light other than R / G / B and only transmit R / G / B, thereby improving the display contrast. In this application, the material of the optical film contains the organic compound selected from the above formula I. Due to the adoption of the organic compound of this application, the optical film can selectively absorb the maximum absorption wavelength λ between green light and blue light max in the cyan light range of 498 nm to 502 nm, and the full width at half maximum of the absorption is less than or equal to 40 nm. The optical film of this application has a narrow full width at half maximum of the absorption and strong absorption ability, can reduce the absorption of green light and blue light, improve the color purity, and further improve the display contrast. At the same time, the preparation process of the optical film is simple, and there is no need to adopt a complex support such as a polarizer, which can achieve the effect of cost reduction and efficiency improvement.

[0067] It is understandable that, in order to absorb visible light other than R / G / B, the material of the optical film further includes a second light-absorbing dye. The absorption wavelength of the second light-absorbing dye is in the range of 570 nm to 620 nm. The second light-absorbing dye can absorb yellow-orange light in the band between red light and green light. Specifically, the second light-absorbing dye for absorbing yellow-orange light can be a known organic compound in the prior art, and the present application does not make specific limitations. The present application aims to provide an organic compound of formula I that absorbs cyan light in the band between green light and blue light, and the maximum absorption wavelength λ max is in the range of 498 nm to 502 nm, and the absorption half-peak width is less than or equal to 40 nm. The optical film of the present application can effectively improve color purity and contrast by using the organic compound selected from formula I.

[0068] The organic compounds and optical films of the present application will be further described below through specific examples.

[0069] I. Synthesis of Organic Compounds

[0070] Example 1

[0071] Synthesis of organic compound I-1-1:

[0072]

[0073] Ethyl 2,4-dimethyl-3-pyrrolepropionate (10 mmol to 15 mmol) and benzaldehyde (5 mmol) were added to dichloromethane and stirred for 10 min to dissolve completely. Then trifluoroacetic acid was added as a catalyst, and the reaction was stirred at room temperature for 24 h to obtain a brown solution. 2,3-Dichloro-5,6-dicyano-p-benzoquinone (5 mmol to 8 mmol) was added to the above brown solution, and the reaction was stirred at room temperature for 1 h to obtain a purple-red solution. Triethylamine (40 mmol to 80 mmol), cobalt acetate (5 mmol) and methanol were added to the above purple-red solution, and the temperature was raised to 35 - 40 °C, and the reaction was stirred for 24 h. After the reaction stopped, it was cooled to room temperature, the solvent was distilled off under reduced pressure, and then purified by column chromatography and recrystallization to obtain a dark green solid, namely organic compound I-1-1. The yield of organic compound I-1-1 was 65%; the mass spectrometry detection result was: 1010.45[M + H + ; the elemental analysis result was: C 68.74, H 7.23, O 12.37, N 5.84.

[0074] Example 2

[0075] Synthesis of organic compound I-1-2:

[0076]

[0077] Ethyl 2,4-dimethyl-3-pyrrolepropionate (10 mmol to 15 mmol) and benzaldehyde (5 mmol) were added to dichloromethane and stirred for 10 min to dissolve completely. Then trifluoroacetic acid was added as a catalyst and the mixture was stirred at room temperature for 24 h to obtain a brown solution. 2,3-Dichloro-5,6-dicyano-p-benzoquinone (5 mmol to 8 mmol) was added to the above brown solution and the mixture was stirred at room temperature for 1 h to obtain a purplish-red solution. Triethylamine (40 mmol to 80 mmol), zinc acetate (5 mmol) and methanol were added to the above purplish-red solution, and the temperature was raised to 35 - 40 °C and stirred for 24 h. After the reaction stopped, it was cooled to room temperature, the solvent was distilled off under reduced pressure, and then purified by column chromatography and recrystallization to obtain a dark green solid, namely organic compound I-1-2. The yield of organic compound I-1-2 was 73%; the mass spectrometry detection result was: 1015.45 [M + H + ; The elemental analysis results were: C 68.12, H 7.31, O 12.28, N 5.79.

[0078] Example 3

[0079] Synthesis of organic compound I-1-3:

[0080]

[0081] Ethyl 2,4-dimethyl-3-pyrrolepropionate (10 mmol to 15 mmol) and 4-n-propylbenzaldehyde (5 mmol) were added to dichloromethane and stirred for 10 min to dissolve completely. Then trifluoroacetic acid was added as a catalyst and the mixture was stirred at room temperature for 24 h to obtain a brown solution. 2,3-Dichloro-5,6-dicyano-p-benzoquinone (5 mmol to 8 mmol) was added to the above brown solution and the mixture was stirred at room temperature for 1 h to obtain a purplish-red solution. Triethylamine (40 mmol to 80 mmol), cobalt acetate (5 mmol) and methanol were added to the above purplish-red solution, and the temperature was raised to 35 - 40 °C and stirred for 24 h. After the reaction stopped, it was cooled to room temperature, the solvent was distilled off under reduced pressure, and then purified by column chromatography and recrystallization to obtain a dark green solid, namely organic compound I-1-3. The yield of organic compound I-1-3 was 71%; the mass spectrometry detection result was: 1094.55 [M + H + ; The elemental analysis results were: C 69.99, H 7.97, O 11.98, N 5.34.

[0082] Comparative Example

[0083] The structures of the comparative compounds are as follows:

[0084]

[0085] II. Preparation of the optical film The preparation method of the optical film is as follows:

[0086] 0.1 wt% - 2.0 wt% of organic compound I-1-1 is mixed with an acrylic monomer, a solvent, a photoinitiator, and a leveling agent, and after processes such as coating, leveling, heat baking, and ultraviolet light curing, a light red optical film 1 is obtained.

[0087] Similarly, using the above method, by replacing organic compound I-1-1 with organic compound I-1-2, an optical film 2 is obtained; by replacing organic compound I-1-1 with organic compound I-1-3, an optical film 3 is obtained; by replacing organic compound I-1-1 with comparative compound D-1, an optical film 4 is obtained.

[0088] III. Optical property testing

[0089] The above optical films 1, 2, 3, and 4 are tested for ultraviolet-visible absorption spectra on an ultraviolet-visible spectrophotometer (instrument model Shimidzu UV-2600) to obtain the maximum absorption wavelength (λ max ), the full width at half maximum of absorption (FWHM), and the transmittance (T), and the haze (Haze) is measured by a haze meter. The relevant test results are shown in Table 1.

[0090] Table 1 Optical property parameters

[0091] Optical film Organic compound <![CDATA[λ max (nm)]]> FWHM (nm) T(％) Haze (%) Optical film 1 I-1-1 501 34 83.22 1.12 Optical film 2 I-1-2 498 37 79.83 1.26 Optical film 3 I-1-3 502 34 84.85 1.21 Optical film 4 D-1 493 28 85.49 1.23

[0092] From Table 1 and Figure 1 - Figure 3 it can be seen that the maximum absorption wavelengths of organic compound I-1-1, organic compound I-1-2, and organic compound I-1-3 are all in the range of 498 nm to 502 nm, and the full width at half maximum of absorption is between 30 nm and 40 nm, proving that organic compound I-1-1, organic compound I-1-2, and organic compound I-1-3 can all absorb cyan light between the green light and blue light bands, and have a narrow full width at half maximum of absorption and excellent optical properties.

[0093] This application also provides a display device 10. Please refer to Figure 4 . The display device 10 includes a display panel 100 and the above-mentioned optical film 200, and the optical film 200 is disposed on the light-emitting side of the display panel 100. Among them, the display panel 100 can be an OLED display panel, including an array substrate 110 and a light-emitting device layer 120.

[0094] The array substrate 110 includes a substrate and a thin-film transistor layer disposed on the substrate, and is used to drive the light-emitting device layer 120 to emit light.

[0095] The light-emitting device layer 120 is disposed above the array substrate 110. Specifically, the light-emitting device layer 120 includes an anode located on the array substrate 110, a light-emitting layer located on the side of the anode away from the array substrate 110, and a cathode located on the side of the light-emitting layer away from the anode. Among them, the light-emitting layer may include at least one of a red sub-light-emitting layer, a green sub-light-emitting layer, and a blue sub-light-emitting layer.

[0096] The display panel 100 further includes a packaging layer 130, and the packaging layer 130 covers the light-emitting device layer 120 to protect the light-emitting device layer 120 and block the erosion of water and oxygen. The packaging layer 130 may include at least one of an inorganic film layer or an organic film layer.

[0097] In the present application, the optical film 200 is disposed on the side of the light-emitting device layer 120 away from the array substrate 110, and includes an organic compound selected as above in Formula I. Therefore, it can selectively absorb cyan light with a maximum absorption wavelength λ max between 498 nm and 502 nm, and the absorption half-peak width is less than or equal to 40 nm, which can effectively improve the color purity and display contrast of the display device.

[0098] The display device 10 of the present application may be a mobile phone, a tablet computer, an eye-protecting display product, an outdoor display product, etc., but is not limited thereto.

[0099] The present application provides an organic compound, an optical film, and a display device. The organic compound provided by the present application includes a conjugated system formed by bonding two methylene dipyrrole units to a metal M through a coordination bond as a main structure. Therefore, it has excellent stability, and a benzene ring is connected to the methylene group, that is, benzene ring groups are introduced at the upper and lower opposite ends of the main structure respectively, further expanding the conjugated structure, causing the absorption of the organic compound to redshift, and being able to absorb cyan light. At the same time, by selecting the R 1 -R 7 groups and the metal M, the maximum absorption wavelength λ max of the organic compound and the absorption half-peak width FWHM can be adjusted, realizing the regulation of the light absorption performance of the organic compound, enabling the organic compound to selectively absorb cyan light in the wavelength band between green light and blue light, and having a narrow absorption half-peak width, and having excellent optical properties. The organic compound of the present application is applied to the optical film, and can effectively absorb cyan stray light in the non-display wavelength band, reduce color crosstalk, and further improve the color purity and display contrast of the display device.

[0100] The technical features of the above-described embodiments can be combined arbitrarily. For the sake of brevity of description, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, it should be considered as the scope recorded in this specification.

[0101] The above-described embodiments merely represent several implementation manners of the present application. The description is relatively specific and detailed, but it should not be construed as a limitation on the scope of the invention patent. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present application, several modifications and improvements can still be made, and these all belong to the protection scope of the present application. Therefore, the protection scope of the patent of the present application shall be subject to the appended claims.

Claims

1. An organic compound, characterized in that, The organic compound has a structure shown in Formula I: Among them, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 is selected from hydrogen or a substituent having 1 to 10 carbon atoms; M represents a divalent transition metal atom.

2. The organic compound according to claim 1, characterized in that, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 is selected from hydrogen or an alkyl group having 1 to 10 carbon atoms, wherein one or more of -H in R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 is unsubstituted or is substituted by -N(R 0 )2, -COOH, one or more of -CH2- in R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 is unsubstituted or is substituted by -O-, -NR 0 -, -CO-, -C(O)O-, -OC(O)-, and R 0 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 compound according to claim 1, wherein R 1 、R 3 、R 5 、R 7 is selected from alkyl groups having 1 to 5 carbon atoms, R 4 is selected from hydrogen or alkyl groups having 1 to 5 carbon atoms.

4. The organic compound according to claim 1, wherein R 2 and R 6 at least one of which contains an ester group or a carboxyl group.

5. The organic compound according to claim 1, characterized in that, The organic compound has a structure shown in Formula I-1: wherein, R 4 , R 8 is selected from hydrogen or an alkyl group having 1 to 5 carbon atoms; n is selected from 0, 1, 2, 3, 4 or 5.

6. The organic compound according to any one of claims 1 to 5, characterized in that, M is selected from Co, Ni, Cu, Zn, Pd or Mg.

7. The organic compound according to claim 6, characterized in that, The maximum absorption wavelength λ of the organic compound max is in the range of 498 nm to 502 nm, and the full width at half maximum of the absorption of the organic compound is less than or equal to 40 nm.

8. An optical film, characterized in that, The optical film includes a first light-absorbing dye, and the first light-absorbing dye includes the organic compound according to any one of claims 1 to 7.

9. The optical film according to claim 8, wherein, The optical film further includes a second light-absorbing dye, and the absorption wavelength of the second light-absorbing dye is in the range of 570 nm to 620 nm.

10. A display device, characterized in that, The display device includes a display panel and the optical film according to claim 8 or 9, and the optical film is disposed on the light-emitting side of the display panel.

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