Light-absorbing material, optical film, and display panel

Abstract

The application discloses an optical material, an optical film and a display panel. The structural formula of the optical material is shown in the specification. The structural formula of Ar is shown in the specification. The optical material provided by the application can be applied to the preparation of the optical film. The absorption peak of the optical material can cover a wider absorption wave band, and the absorption range of the optical material in the infrared wave band can be expanded, so that the inhibition ability of the optical material to external stray light and ambient light is improved, and the contrast, color saturation and display stability of the optical film and the display panel are significantly improved, and the application prospect of the optical film and the display panel in the display field is expanded.

Description

Technical Field

[0001] This application relates to the field of display technology, specifically to a light-absorbing material, an optical film, and a display panel. Background Technology

[0002] Porphyrins and their derivatives can be applied to a variety of fields such as coloring dyes and colored photoresists. Fused ring derivatives based on porphyrin skeletons are considered to be next-generation functional materials with broad application prospects.

[0003] However, the design and development of existing porphyrin molecular systems mainly focus on utilizing the absorption properties in the blue light band, resulting in insufficient light absorption modulation capabilities in the infrared light band, which significantly limits their application range and efficiency in optoelectronic devices and displays.

[0004] Therefore, there is an urgent need to develop new porphyrin-based materials to expand their application scenarios in the display field. Summary of the Invention

[0005] This application provides a light-absorbing material, an optical film, and a display panel. The light-absorbing material can be used in the preparation of the optical film. The absorption peak of the light-absorbing material undergoes a red shift, thereby expanding its absorption range in visible light and broadening its application prospects in the display field.

[0006] In a first aspect, this application provides a light-absorbing material, the structural formula of which is shown in formula (1): (1); When multiple Ar appear simultaneously, they may be the same or different from each other, and the structural formula of Ar is shown in equation (2): (2); R1 to R6 are independently selected from hydrogen atoms, halogen atoms, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 10 carbon atoms, substituted or unsubstituted thio groups, cyano groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryl groups having 1 to 20 cyclic atoms, and substituted or unsubstituted heteroaryl groups having 1 to 20 cyclic atoms. One or more combinations thereof; Indicates the connection site with L; a and b are selected from 0, 1, or 2; c, d, e, and f are selected from 0, 1, 2, or 3; L is selected from one or more combinations of single bond, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted alkenyl with 1 to 10 carbon atoms, substituted or unsubstituted alkoxy with 1 to 10 carbon atoms, substituted or unsubstituted thiol, substituted or unsubstituted amino, substituted or unsubstituted aryl with 1 to 20 ring atoms, and substituted or unsubstituted heteroaryl with 1 to 20 ring atoms; m is selected from 0 or 1, and when m=0, two adjacent Ar are either fused or screwed together; n is any integer from 1 to 10; The substituted or unsubstituted substituents in R1 to R6 and L are independently selected from one or more combinations of deuterium, cyano, isocyano, nitro, halogen atom, alkyl containing 1 to 20 carbon atoms, heterocyclic group having 3 to 20 ring atoms, aryl group having 6 to 20 ring atoms, heteroaryl group having 5 to 20 ring atoms, -NR'R'', silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, and trifluoromethyl. In -NR'R'', R' and R'' are independently selected from one or more combinations of H, deuterium atom, cyano, isocyano, nitro, halogen atom, alkyl with 1 to 10 carbon atoms, heterocyclic group with 3 to 20 carbon atoms, aryl with 6 to 20 ring atoms, and heteroaryl with 5 to 20 ring atoms.

[0007] Secondly, this application provides an optical film, the material of which includes the light-absorbing material described above.

[0008] Thirdly, this application provides a display panel, the display panel including the above-mentioned optical film.

[0009] This application provides a light-absorbing material, an optical film, and a display panel. The light-absorbing material shown in formula (1) can be used in the preparation of the optical film. The light-absorbing material is an oligomer structure with porphyrin derivative monomers. By introducing the porphyrin derivative unit shown in formula (2) into the oligomer backbone, the absorption peak of the light-absorbing material is red-shifted and continuously covers a wider near-infrared light band, thereby expanding its absorption range in the infrared band, improving the ability to suppress stray light and ambient light, and thus significantly improving the contrast, color saturation, and display stability of the optical film and the display panel, expanding its application prospects in the display field. Attached Figure Description

[0010] Figure 1 This is the UV-Vis absorption spectrum of CP dimer I-2 provided in an exemplary embodiment of this disclosure; Figure 2This is the UV-Vis absorption spectrum of CP dimer II-1 provided in an exemplary embodiment of this disclosure; Figure 3 This is the UV-Vis absorption spectrum of the comparative compound Ref1 provided in the exemplary embodiments of this disclosure; Figure 4 This is a schematic diagram of a display panel provided in an exemplary embodiment of this disclosure; Figure 5 This is another structural schematic diagram of the display panel provided in an exemplary embodiment of this disclosure.

[0011] Explanation of reference numerals in the attached figures: 100. Display panel; 10. Light-emitting component; 20. Optical film; 30. Functional layer. Detailed Implementation

[0012] The technical solutions in the embodiments of this application will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments in this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application.

[0013] This application provides a light-absorbing material, an optical film, and a display panel. These are described in detail below. It should be noted that the order of description of the following embodiments is not intended to limit the preferred order of the embodiments. Furthermore, in the description of this application, the term "comprising" means "including but not limited to". The terms first, second, third, etc., are used merely as illustrative and do not impose numerical requirements or establish an order. Various embodiments of the present invention may exist in the form of a range; it should be understood that the description in the form of a range is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of the invention; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within that range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Additionally, whenever a numerical range is indicated herein, it means including any referenced number (fraction or integer) within the indicated range.

[0014] In the embodiments of this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0015] In the embodiments of this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0016] In the embodiments of this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

[0017] In the embodiments of this application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0018] In the embodiments of this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that the defined group can be substituted by one or more substituents R, wherein R is selected from, but is not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R'', silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, etc. Formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R'' in -NR'R'' are independently selected from, but not limited to: H, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, and heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, trifluoromethyl, and the above groups may also be further substituted with substituents acceptable in the art.

[0019] In the embodiments of this application, "ring atom number" refers to the number of atoms in the ring-forming structure of a compound (e.g., monocyclic compound, fused ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by atomic bonding. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thiophene group has 5 ring atoms.

[0020] In the embodiments of this application, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluoranthracene, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl and their derivatives. It is understandable that multiple aryl groups can also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9'-diarylfluorene, triarylamine, and diaryl ether systems should also be included in the definition of aryl.

[0021] In the embodiments of this application, "heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to, thiophene, furanyl, pyrrole, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, and pyrimidine. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0022] In the embodiments of this application, "alkyl" may refer to a straight-chain, branched, and / or cyclic alkyl group. The number of carbon atoms in an alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, such as "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each time it appears, it can independently be C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, or C9 alkyl. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-butyl... Pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3 7-Dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-hepta ...

[0023] In the embodiments of this application, "amine group" refers to an amine derivative having the structural feature of formula -N(X)2, wherein each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amine groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0024] In the embodiments of this application, unless otherwise defined, hydroxyl group refers to -OH, carboxyl group refers to -COOH, carbonyl group refers to -C(=O)-, amino group refers to -NH2, formyl group refers to -C(=O)H, haloformyl group refers to -C(=O)Z (where Z represents halogen), carbamoyl group refers to -C(=O)NH2, isocyanate group refers to -NCO, and isothiocyanate group refers to -NCS.

[0025] In the embodiments of this application, the term "alkoxy" refers to a group with the structure "-O-alkyl", that is, an alkyl group as defined above that is attached to other groups via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and tert-butoxy (-OC(CH3)3 or -OtBu).

[0026] In the embodiments of this application, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0027] In the embodiments of this application, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, and preferably two or more sites in the adjacent position of the group are fusion sites.

[0028] In the embodiments of this application, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six Rs on the benzene ring can be the same or different from each other.

[0029] Currently, the design and development of porphyrin molecular systems mainly focus on utilizing their absorption properties in the blue light band, resulting in insufficient light absorption modulation capabilities in the infrared light band. Consequently, their application range and efficiency in optoelectronic devices and displays are significantly limited.

[0030] Porphyrin is an organic molecule consisting of four pyrroles linked by methylene groups in a ring, and its structural formula is shown below: .

[0031] Porphyrins possess excellent chemical and thermal stability and exhibit a significant characteristic absorption peak in the blue light region, making them suitable for applications in coloring dyes, photocatalysis, and color resists. Porphyrin-based fused-ring derivatives are potential next-generation materials. On one hand, the introduction of fused-ring structures in these derivatives enhances their photothermal stability. On the other hand, by partially replacing the nitrogen atoms in the four pyrrole atoms with other non-metallic elements (such as oxygen and sulfur), the characteristic absorption, color appearance, and luminescence properties of porphyrin-based materials can be modulated.

[0032] For example, CP is a porphyrin derivative based on a biscarbazole fused ring structure, in which two nitrogen atoms in the porphyrin are replaced by sulfur atoms, and its structural formula is shown below: .

[0033] Due to the increased conjugation of CP and the replacement of two pyrrole structures with thiophene, CP exhibits a significant redshift in its absorption peak compared to porphyrins. It possesses characteristic absorption in the infrared region of 600 nm–1100 nm, making it suitable as an infrared light absorbing material. However, the absorption of CP in the 600 nm–1100 nm infrared region is not complete; it exhibits an absorption trough at approximately 900 nm.

[0034] Based on this, this application provides an oligomer of CP that exhibits stronger absorption in the infrared region, particularly filling the absorption gap of CP monomers at approximately 900 nm. The oligomer light-absorbing material provided by this application can serve as a novel infrared light-absorbing material, applicable to optical films or filter components requiring controlled infrared light transmission, such as display devices, infrared cut-off filters, and automotive windshields, achieving the effect of blocking heat while maintaining high visible light transmittance.

[0035] This application provides a light-absorbing material, the structural formula of which is shown in formula (1): (1); When multiple Ar appear simultaneously, they may be the same or different from each other, and the structural formula of Ar is shown in equation (2): (2); R1 to R6 are independently selected from hydrogen atoms, halogen atoms, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 10 carbon atoms, substituted or unsubstituted thio groups, cyano groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryl groups having 1 to 20 cyclic atoms, and substituted or unsubstituted heteroaryl groups having 1 to 20 cyclic atoms. One or more combinations thereof; Indicates the connection site with L; a and b are selected from 0, 1, or 2; c, d, e, and f are selected from 0, 1, 2, or 3; L is selected from one or more combinations of single bond, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted alkenyl with 1 to 10 carbon atoms, substituted or unsubstituted alkoxy with 1 to 10 carbon atoms, substituted or unsubstituted thiol, substituted or unsubstituted amino, substituted or unsubstituted aryl with 1 to 20 ring atoms, and substituted or unsubstituted heteroaryl with 1 to 20 ring atoms; m is selected from 0 or 1. When m=0, two adjacent Ar are fused or screwed together; when m=1, one of the multiple R1s, one of the multiple R2s, one of the multiple R3s, one of the multiple R4s, one of the multiple R5s, and one of the multiple R6s are selected from... .

[0036] n is any integer from 1 to 10; The substituted or unsubstituted substituents in R1 to R6 and L are independently selected from one or more combinations of deuterium, cyano, isocyano, nitro, halogen atom, alkyl containing 1 to 20 carbon atoms, heterocyclic group having 3 to 20 ring atoms, aryl group having 6 to 20 ring atoms, heteroaryl group having 5 to 20 ring atoms, -NR'R'', silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, and trifluoromethyl. In -NR'R'', R' and R'' are independently selected from one or more combinations of H, deuterium atom, cyano, isocyano, nitro, halogen atom, alkyl with 1 to 10 carbon atoms, heterocyclic group with 3 to 20 carbon atoms, aryl with 6 to 20 ring atoms, and heteroaryl with 5 to 20 ring atoms.

[0037] It is understood that in the embodiments of this application, when multiple R1s appear simultaneously in the light-absorbing material shown in formula (1), they are the same or different from each other; when multiple R2s appear simultaneously, they are the same or different from each other; when multiple R3s appear simultaneously, they are the same or different from each other; when multiple R4s appear simultaneously, they are the same or different from each other; when multiple R5s appear simultaneously, they are the same or different from each other; when multiple R6s appear simultaneously, they are the same or different from each other.

[0038] This application provides a light-absorbing material, wherein the light-absorbing material shown in formula (1) can be used in the preparation of optical films. The light-absorbing material is an oligomer structure with porphyrin derivative monomers. By introducing the porphyrin derivative unit shown in formula (2) into the oligomer backbone, the absorption peak of the light-absorbing material is red-shifted and continuously covers a wider near-infrared light band, thereby expanding its absorption range in the infrared band, improving the ability to suppress stray light and ambient light, and thus significantly improving the contrast, color saturation and display stability of optical films and display panels, expanding its application prospects in the display field.

[0039] In some embodiments, in the light-absorbing material shown in formula (1), multiple Ar atoms are the same as each other. In this way, when the absorption band covers the near-infrared region of 900nm~1100nm, the same monomer can be used to prepare the material, shorten the material development cycle, reduce the synthesis difficulty, and reduce the preparation cost.

[0040] In some embodiments, n=1; at this time, the compound shown in formula (1) is a dimer, and the absorption band can cover the near-infrared region of 900nm~1100nm. While increasing the absorption band range of infrared light, it also makes the light-absorbing material have better solubility in organic solvents, making it more suitable for industrial production.

[0041] In some embodiments, m=1, and the light-absorbing material has a structure as shown in formula (1-2): .

[0042] In this embodiment of the application, when two adjacent Ar atoms are connected by a single bond, the light-absorbing material has a large absorption rate for light in the 800 nm to 1100 nm wavelength band.

[0043] In some embodiments, the light-absorbing material is selected from compounds with structures such as CP dimer I: (CP dimer I).

[0044] In one specific embodiment, in CP dimer I, R4, R5, and R6 are selected from groups that are not hydrogen, d, e, and f are selected from 1; R1, R2, and R3 are selected from hydrogen or deuterium, a and b are selected from 2, and c is selected from 3.

[0045] In some embodiments, the structural formula of Ar is shown in formula (2-1): (2-1).

[0046] It is understandable that any one of R3 to R6 can be a single bond, used to connect with another Ar.

[0047] In one specific embodiment, in formula (2-1), three of R3 to R6 are selected from the same functional group. Thus, the light-absorbing material can be generated from a single intermediate, reducing the synthesis process and lowering preparation costs.

[0048] In some embodiments, CP dimer I has any of the following structural formulas: I-1 I-2 I-3 I-4.

[0049] It is understandable that in the above structural formula, Mes represents 2,4,6-trimethylphenyl, tBu represents tert-butyl, and Me represents methyl.

[0050] It is understood that the light-absorbing material structures in the embodiments of this application are not limited to those listed above.

[0051] In this embodiment of the application, the preparation process of one of the CP dimers I is as follows:

[0052] .

[0053] It is understandable that in the above preparation process of CP dimer I, R4 to R6 are selected from the same group R, and CP dimer I is the aforementioned light-absorbing material.

[0054] The specific steps of the above preparation process are as follows: Step 1: Using 3-bromocarbazole (I) as a raw material, react it with substituted boric acid or borate ester under the action of Pd catalyst to generate carbazole (II) substituted at the 3-position. Step 2: Under the action of FeCl3, the Scholl reaction occurs to form a 3 / 3' substituted carbazole dimer (III); Step 3: Under the action of Ir catalyst and ligand, carbazole dimer (III) reacts with 4 molecules of pinacol diboronic acid ester to generate a boronic acid ester product with tetrasubstituted 1 / 1' / 8 / 8' position; the obtained product then reacts with Br-C≡C-TIPS under the action of Pd catalyst and ligand to obtain a tetra-tetryyne product (IV) protected by 1 / 1' / 8 / 8' position tetrasubstituted TIPS (triisopropylsilyl); Step 4: TIPS in the tetrayne product (IV) are removed by TBAF (tetra-n-butylammonium fluoride) to generate an unprotected tetrayne product (V); Step 5: The tetrayne product (V) reacts with two molecules of diyne monocarbazole precursor (VI) under the action of Cu catalyst, resulting in two intermolecular cyclizations; the product then reacts with Na2S, causing four pairs of adjacent yyn groups to undergo intramolecular cyclization, forming four thiophene units, to obtain the target molecular skeleton (VII). Step 6: Under the action of the oxidant, the target molecular skeleton (VII) undergoes dehydrogenation, ultimately forming the target product CP dimer I.

[0055] In some embodiments, m=0, and the light-absorbing material has the structure shown in formula (1-1) (also known as CP polymer II): (1-1).

[0056] In this embodiment, when two adjacent Ar atoms are fused together, the molecular structure becomes more rigid, which is beneficial to improving the stability of the light-absorbing material. This makes it easier to extend the lifespan of the display device when the light-absorbing material is used in the display device. Moreover, the light-absorbing material shown in formula (1-1) has a large absorption rate for light in the 900 nm to 1300 nm wavelength range.

[0057] In one specific embodiment, in CP dimer II, R4, R5, and R6 are selected from groups that are not hydrogen, d, e, and f are selected from 1; R1, R2, and R3 are selected from hydrogen or deuterium, and a and b are selected from 2.

[0058] In some embodiments, the structural formula of Ar is shown in equation (2-2): (2-2); Where * represents a fusion site.

[0059] In some embodiments, CP dimer II is selected from any of the following structural formulas: II-1 II-2 II-3 II-4.

[0060] It is understood that the structural formula of the light-absorbing material in the embodiments of this application is not limited to the compounds listed above.

[0061] In this embodiment of the application, the preparation process of CP dimer II is as follows:

[0062] It is understandable that in the above flowchart for the preparation of CP dimer II, R3 to R6 are selected from the same group R, and CP dimer II is a light-absorbing material; The specific steps of the above preparation process are as follows: Step 1: 1,5-diboron ester naphthalene (I) and two molecules of substituted o-nitrobromobenzene (II) undergo a Suzuki coupling reaction in the presence of a Pd catalyst to form the compound shown in Formula III; Step 2: The compound shown in Formula III undergoes a heating reaction under the action of PPh3, the NO2 group is reduced and intramolecular cyclization occurs, forming a biscarbazole core structure with a fused ring (IV). The synthesis steps from the third to the sixth are the same as those for the synthesis of CP dimer I.

[0063] In some embodiments, R1 to R6 are independently selected from groups containing F atoms, alkyl groups containing 2 or more carbon atoms, or groups containing phenyl groups. When R1 to R6 are selected from the above groups, the solubility of the light-absorbing material in organic solvents can be further improved, making it more suitable for the process preparation of optical film 20.

[0064] In some embodiments, when R1 to R6 are independently selected from at least one of an alkyl group containing 4 or more carbon atoms or a group containing 3 or more fluorine atoms, the substituents have a better solubilizing effect, making the light-absorbing material soluble in various common organic solvents.

[0065] In one specific embodiment, R1 to R6 are independently selected from any one of hydrogen atom, fluorine atom, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, neopentyl, isopentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 1,3-butadienyl, ethynyl, 1-propynyl, 2-propynyl, methylamino, ethylamino, methylamino, diethylamino, phenyl, methoxy, ethoxy, propoxy, butoxy, methylthio, ethylthio, cyano, trifluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, phenyl, 2,6-dimethylphenyl, and 2,4,6-trimethylphenyl.

[0066] In one specific embodiment, R1 to R3 are independently selected from hydrogen atoms.

[0067] In some embodiments, the light-absorbing material's absorption spectrum continuously covers the near-infrared band from 700 nm to 1400 nm. This enables absorption of infrared light across a wide wavelength range of 700 nm to 1400 nm, improving the material's ability to modulate infrared light.

[0068] In some embodiments, the light-absorbing material's absorption spectrum continuously covers the near-infrared band from 700 nm to 1300 nm. This enables absorption of infrared light across a wide wavelength range of 700 nm to 1300 nm, improving the material's ability to modulate infrared light.

[0069] In some embodiments, the wavelength of one of the absorption troughs in the absorption spectrum of the light-absorbing material lies in the green to red light band. In this case, the embodiments of this application can be applied to the preparation of materials that selectively transmit green light, such as green color resists in color filters.

[0070] In some embodiments, the light-absorbing material has a first absorption peak and a second absorption peak in its absorption spectrum, wherein the first absorption peak is located in the ultraviolet to blue light band, and the second absorption peak is located in the near-infrared band. In this case, the embodiments of this application can be used to prepare optical films that absorb ultraviolet to blue light and near-infrared light. When applied to display devices, these films can prevent infrared interference, provide heat insulation, and suppress ambient light infrared crosstalk.

[0071] This application also provides an optical film, the material of which includes the light-absorbing material described in the foregoing embodiments.

[0072] In some embodiments, the optical film includes a substrate and a light-absorbing dye dispersed in the substrate, wherein the mass ratio of the light-absorbing material to the substrate is (0.005~0.08):1.

[0073] In some embodiments, the mass ratio of light-absorbing material to substrate in the optical film is 0.75% to 7.5%. This further enhances the optical film's ability to absorb infrared light.

[0074] In some embodiments, the substrate material includes an optical resin material, such as an acrylic resin. This allows the optical film to possess better optical properties.

[0075] In some embodiments, the optical film has a transmittance of less than 50% for light in the 900 nm to 1100 nm wavelength range. In this case, when the optical film is applied to a display device, it can absorb infrared light, thereby achieving the effect of blocking heat while maintaining high visible light transmittance.

[0076] This application also provides a composition for preparing the optical film described in the foregoing embodiments, the composition comprising a resin, a monomer, an initiator, and the light-absorbing material described in the foregoing embodiments.

[0077] Specifically, after the resin and monomer are mixed with the light-absorbing material, the resin and monomer polymerize under the action of the initiator to form a substrate, while the light-absorbing material is dispersed in the substrate to form an optical film.

[0078] In some embodiments, the composition further includes at least one of a leveling agent, a dispersant, and a solvent, thereby further improving the performance of the optical film and / or making the composition more suitable for optical film preparation processes.

[0079] In some embodiments, the mass ratio of the light-absorbing material to other solids in the composition is 0.75% to 7.5%. This further enhances the absorption capacity of the optical film for infrared light.

[0080] This application also provides a method for preparing the optical film described in the foregoing embodiments, comprising the following steps: Step S1: Mix the above composition to form a fluid material, and apply the mixed composition to the surface of the substrate using a coating process; Step S2: Remove the solvent from the composition and perform a curing process to obtain an optical film.

[0081] The optical film of the aforementioned embodiment can be obtained by using the above process.

[0082] This application provides different light-absorbing materials and their preparation methods through Examples 1 to 8.

[0083] The molecular formula of the light-absorbing material in Example 1 is shown below: (CP dimer I-1).

[0084] The light-absorbing material (CP dimer I-1) in Example 1 was prepared using the following steps: (i) Under a nitrogen atmosphere, 3-bromocarbazole (3 mmol), 2,4,6-trimethylphenylboronic acid (3.6 mmol), potassium carbonate (9.4 mmol), and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.06 mmol) were heated to 100 °C and reacted for 24 h in a mixed solvent of toluene / ethanol / water (10 / 5 / 5 mL). After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was extracted with dichloromethane, washed with water, dried over sodium sulfate, and concentrated to obtain a crude product. The crude product was then purified by silica gel column chromatography (using a mixed solvent of n-hexane and dichloromethane as eluent) to obtain 3-(2,4,6-trimethylphenyl)carbazole in 70% yield.

[0085] 1H NMR spectrum of the product 1 The ¹H NMR (CDCl₃, 400 MHz) results are as follows: 8.08 (s, 1H), 8.03 (d, 1H), 7.83 (d, 1H), 7.49–7.42 (m, 3H), 7.23 (d, 1H), 7.18 (d, 1H), 6.98 (s, 2H), 2.36 (s, 3H), 2.04 (s, 6H); MS mass spectrometry: 285.1447 [M]. + ].

[0086] (ii) Under a nitrogen atmosphere, 3-(2,4,6-trimethylphenyl)carbazole (3.6 mmol) and ferric chloride (14.4 mmol) were reacted in anhydrous chloroform (45 mL) at room temperature with stirring for 1 h. After the reaction was complete, the reaction solution was extracted with dichloromethane, washed with water, dried over sodium sulfate, and concentrated to obtain a crude product. The crude product was then purified by silica gel chromatography (using a mixed solvent of n-hexane and dichloromethane as eluent) to obtain 6,6'-(2,4,6-trimethylphenyl)-3,3'-bicarbazole in 68% yield.

[0087] The 1H NMR (CDCl3, 400 MHz) results of the product are as follows: 8.39 (s, 2H), 7.97 (s, 2H), 7.92 (s, 2H), 7.80 (d, 2H), 7.47 (d, 2H), 7.46 (d, 2H), 7.26 (d, 2H), 7.07 (s, 4H), 2.45 (s, 6H), 2.14 (s, 12H); MS mass spectrometry: 568.2808 [M]. + ].

[0088] (iii) Under a nitrogen atmosphere, 6,6'-(2,4,6-trimethylphenyl)-3,3'-bicarbazole (3.9 mmol), pinacol diborate (11.8 mmol), bis(1,5-cyclooctadiene)di-μ-methoxydiiridium(I) ([Ir(OMe)(cod)]2, 0.39 mmol), and 4,4'-di-tert-butyl-2,2'-bipyridine (dtbpy, 0.78 mmol) were heated to 70 °C and reacted for 24 h in anhydrous tetrahydrofuran (3 mL). After the reaction was complete, the reaction solution was filtered through diatomaceous earth to remove insoluble matter, and the filter cake was washed with dichloromethane. The filtrate was concentrated to obtain the crude intermediate product, which was used directly in the next step. Under a nitrogen atmosphere, the above crude product, (2-bromoethynyl)triisopropylsilane (20 mmol), tris(dibenzylacetone)dipalladium (Pd2(dba)3, 2 mmol), 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (Xantphos, 4 mmol), and potassium phosphate (80 mmol) were heated to 110 °C and reacted for 24 h in a dioxane / water mixed solvent (45 / 5 mL). After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was extracted with dichloromethane, washed with water, dried over sodium sulfate, and concentrated to obtain the crude product. The crude product was then purified by silica gel column chromatography (eluting with a mixed solvent of n-hexane and dichloromethane) to obtain the TIPS-protected tetraynebicarbazole product in 25% yield.

[0089] The 1H NMR (CDCl3, 400 MHz) results of the product are as follows: 8.52 (s, 2H), 8.27 (d, 2H), 7.91 (d, 2H), 7.89 (d, 2H), 7.41 (d, 2H), 6.98 (s, 4H), 2.37 (s, 6H), 2.09 (s, 12H), 1.27 – 1.24 (m, 84H); MS: 1289.8170 [M]. + ].

[0090] (iv) The product (3.7 mmol) from step (iii) was dissolved in anhydrous tetrahydrofuran (50 mL), and a tetrahydrofuran solution of tetra-n-butylammonium fluoride (TBAF, 1.0 M, 15 mL) was added. The mixture was heated to 60 °C and reacted for 1 h. After the reaction was complete, the product was concentrated, and the crude product was purified by silica gel chromatography (eluting solvent was a mixture of n-hexane and dichloromethane) to give the deprotected tetraynebicarbazole product in 90% yield.

[0091] The 1H NMR (CDCl3, 400 MHz) results of the product are as follows: 8.68 (s, 2H), 8.28 (d, 2H), 7.92 (s, 2H), 7.91 (s, 2H), 7.41 (d, 2H), 6.97 (s, 4H), 3.54 (s, 2H), 3.53 (s, 2H), 2.36 (s, 6H), 2.05 (s, 12H); MS mass spectrometry: 664.2802 [M]. + ].

[0092] (v) Copper acetate monohydrate (5 mmol) was added to pyridine (40 mL) to obtain suspension A. The product from step (iv) (0.12 mmol) was dissolved in toluene (135 mL) with 1,8-diethynyl-3,6-bis(2,4,6-trimethylphenyl)carbazole to obtain solution B. Solution B was slowly added dropwise to solution A. After the addition was complete, the reaction temperature was raised to 50 °C and the reaction was carried out for 72 h. After the reaction was completed, the reaction solution was filtered through diatomaceous earth to remove insoluble matter, and the filter cake was washed with dichloromethane. The filtrate was concentrated to obtain the crude intermediate product, which was used directly in the next step. The above crude product was dissolved in sodium sulfide nonahydrate (10 mmol) in a mixed solvent of toluene / 2-methoxyethanol (10 / 10 mL), heated to 100 °C and reacted for 12 h. After the reaction was completed, the solution was cooled to room temperature, extracted with dichloromethane, washed with water, dried with sodium sulfate, and concentrated to obtain the crude product. The crude product was then purified by silica gel chromatography (using a mixed solvent of n-hexane and dichloromethane as the eluent) to obtain unoxidized CP dimer I-1 in 10% yield.

[0093] The 1H NMR (CDCl3, 400 MHz) results of the product are as follows: 10.76 (s, 2H), 10.57 (s, 2H), 8.46 (s, 2H), 8.21 (d, 2H), 8.13 (s, 4H), 8.00 (s, 2H), 7.86 (d, 2H), 7.84 (d, 2H), 7.62 (d, 2H), 7.59 (d, 2H), 7.47 (d, 2H), 7.43 (d, 2H), 7.42 (d, 2H), 7.16 (s, 8H), 7.04 (s, 4H), 2.40 (s, 6H), 2.37 (s, 6H), 2.25 (s, 6H). 2.18 (s, 12H), 2.17 (s, 12H), 2.09 (s, 12H); MS: 1696.6360 [M+].

[0094] (vi) The product (1 mmol) from step (v) was dissolved in dichloromethane (150 mL), lead dioxide was added, and the mixture was stirred vigorously for 12 h. After the reaction was completed, the product was filtered through diatomaceous earth, washed with dichloromethane, and concentrated to obtain dark green CP dimer I-1, with a yield of 91%.

[0095] The 1H NMR (CDCl3, 400 MHz) results of the product are as follows: 10.90 (s, 2H), 10.76 (d, 2H), 10.32 (d, 2H), 10.28 (d, 2H), 10.24 (d, 2H), 10.18 (s, 2H), 9.95 (s, 2H), 9.94 (s, 2H), 9.67 (s, 2H), 9.19 (s, 4H), 8.73 (s, 2H), 7.56 (s, 8H), 7.25 (s, 4H), 2.50 (s, 6H, Me), 2.48 (s, 6H), 2.44 (s, 6H), 2.43 (s, 12H), 2.41 (s, Me). 12H), 2.40 (s, 12H); Mass spectrometry (MS): 1692.6082 [M] + ].

[0096] The molecular formula of the light-absorbing material in Example 2 is shown below: (CP dimer I-2).

[0097] The synthesis steps of CP dimer I-2 are the same as those of CP dimer I-1, except that the starting material 3-(2,4,6-trimethylphenyl)carbazole in step (ii) is replaced with 3-tert-butylcarbazole, and the 1,8-diethynyl-3,6-bis(2,4,6-trimethylphenyl)carbazole in step (v) is replaced with 1,8-diethynyl-3,6-ditert-butylcarbazole, thus obtaining the product CP dimer I-2. The mass spectrometry (MS) results of CP dimer I-2 are as follows: 1318.5109 [M + ].

[0098] The molecular formula of the light-absorbing material in Example 3 is shown below: (CP dimer I-3).

[0099] The synthesis steps of CP dimer I-3 were the same as those of CP dimer I-1, except that the starting material 3-(2,4,6-trimethylphenyl)carbazole in step (ii) was replaced with 3-trifluoromethylcarbazole, and the 1,8-diethynyl-3,6-bis(2,4,6-trimethylphenyl)carbazole in step (v) was replaced with 1,8-diethynyl-3,6-bistrifluoromethylcarbazole, yielding the product CP dimer I-3. The mass spectrometry (MS) results of CP dimer I-3 are as follows: 1390.0596 [M + ].

[0100] The molecular formula of the light-absorbing material in Example 4 is shown below: (CP dimer I-4).

[0101] The synthesis steps of CP dimer I-4 were the same as those of CP dimer I-1, except that the starting material 3-(2,4,6-trimethylphenyl)carbazole in step (ii) was replaced with 3-methoxycarbazole, and the 1,8-diethynyl-3,6-bis(2,4,6-trimethylphenyl)carbazole in step (v) was replaced with 1,8-diethynyl-3,6-dimethoxycarbazole, yielding the product CP dimer I-4. The mass spectrometry (MS) results of CP dimer I-4 are as follows: 1162.1987 [M + ].

[0102] The molecular formula of the light-absorbing material in Example 5 is shown below: (CP dimer II-1).

[0103] The specific synthetic steps of CP dimer II-1 are as follows: (i) Under a nitrogen atmosphere, 1,5-bis(pinacol diborate)naphthalene (9.2 mmol), 2-bromo-4-tert-butyl-1-nitrobenzene (2.95 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.18 mmol), and potassium carbonate (8.8 mmol) were heated to 100 °C and reacted for 24 h in a mixed solvent of toluene / ethanol / water (20 / 10 / 10 mL). After the reaction was completed, the mixture was cooled to room temperature, and the reaction solution was extracted with ethyl acetate, washed with water, dried over sodium sulfate, and concentrated to obtain a crude product. The crude product was then purified by silica gel column chromatography (using a mixed solvent of n-hexane and dichloromethane as eluent) to obtain 1,5-bis(2-nitro-5-tert-butylphenyl)naphthalene in 93% yield.

[0104] The 1H NMR spectra of the product (CDCl3, 400 MHz) are as follows: 8.07 (d, 2H), 7.62 (d, 2H), 7.55 (d, 2H), 7.51 7.41 (m, 4H), 7.35 (d, 2H), 1.41 (s, 18H); Mass spectrometry (MS): 483.2209 [M] + ].

[0105] (ii) Under a nitrogen atmosphere, 1,5-bis(2-nitro-5-tert-butylphenyl)naphthalene (3 mmol) and triphenylphosphine (15 mmol) were heated to 180 °C and reacted for 12 h in o-dichlorobenzene (20 mL). After the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was then purified by silica gel chromatography (eluent: dichloromethane) to obtain a bis-tert-butyl-substituted fused-ring carbazole dimer in 70% yield.

[0106] The 1H NMR (DMSO-d6, 400 MHz) results of the product are as follows: 11.56 (s, 2H), 8.85 (d, 2H), 8.57 (s, 2H), 7.98 (d, 2H), 7.58 (d, 2H), 7.54 (d, 2H), 1.51 (s, 18H); MS: 418.2342 [M+].

[0107] (iii) The reaction steps and feed amounts are the same as in step (iii) of CP dimer I-2, except that the bicarbazole precursor is replaced with the corresponding fused-ring carbazole dimer, and the yield is 40%.

[0108] The 1H NMR (CDCl3, 400 MHz) results of the product are as follows: 9.03 (s, 2H), 8.75 (s, 2H, NH), 8.61 (s, 2H), 7.70 (s, 2H), 1.53 (s, 18H), 1.27 (s, 42H), 1.24 (s, 42H); MS mass spectrometry: 1139.7676 [M + ].

[0109] (iv) The reaction steps and feed amounts are the same as in step (iv) of CP dimer I-2, except that the bicarbazole precursor is replaced with the corresponding fused-ring carbazole dimer, and the yield is 72%.

[0110] The 1H NMR (CDCl3, 400 MHz) results of the product are as follows: 8.95 (s, 2H), 8.88 (s, 2H), 8.62 (d, 2H), 7.76 (d, 2H), 3.68 (s, 2H), 3.52 (s, 2H), 1.56 (s, 18H); MS mass spectrometry: 514.2341 [M + ].

[0111] (v) The reaction steps and feed amounts are the same as in step (v) of CP dimer I-2, except that the bicarbazole precursor is replaced with the corresponding fused-ring carbazole dimer, and 1,8-dieethynyl-3,6-bis(2,4,6-trimethylphenyl)carbazole is replaced with 1,8-dieethynyl-3,6-di-tert-butylcarbazole, with a yield of 11%.

[0112] The 1H NMR spectrum (CDCl3, 400 MHz) of the product is as follows: 10.82 (s, 2H), 10.56 (s, 2H), 9.28 (s, 2H), 8.83 (s, 2H), 8.15 (s, 2H), 8.13 (s, 2H), 7.94 (s, 2H), 7.91 (d, 2H), 7.85 (s, 2H), 7.80 (d, 2H), 7.60 (d, 2H), 7.51 (s, 2H), 7.45 (s, 2H), 1.68 (s, 54H); MS mass spectrometry: 1297.5168 [M + ].

[0113] (vi) The reaction steps and feed amounts are the same as in step (vi) of CP dimer I-2, except that the bicarbazole core dimer precursor is replaced with the corresponding fused-ring carbazole core dimer, and the yield is 59%.

[0114] The 1H NMR (CDCl3, 400 MHz) results of the product are as follows: 11.11 (d, 2H), 10.40 (s, 2H), 10.19 (d, 2H), 9.96 (s, 2H), 9.92 (s, 2H), 9.77 (s, 2H), 9.71 (s, 2H), 9.65 (s, 2H), 9.18 (s, 2H), 9.06 (s, 2H), 9.05 (s, 2H), 2.01 (s, 54H); MS mass spectrometry: 1293.4992 [M]. + ].

[0115] The molecular formula of the light-absorbing material in Example 6 is shown below: (CP dimer II-2).

[0116] The specific synthesis steps for CP dimer II-2 are the same as those for CP dimer II-1, with the following differences: Starting from step (i), the starting material 2-bromo-4-tert-butyl-1-nitrobenzene was replaced with 2-bromo-4-(2,4,6-trimethylphenyl)-1-nitrobenzene, and the 1,8-diethynyl-3,6-di-tert-butylcarbazole in step (v) was replaced with 1,8-diethynyl-3,6-di(2,4,6-trimethylphenyl)carbazole, yielding product CP dimer II-2. The mass spectrometry (MS) result of the product was: 1665.5925 [M + ].

[0117] The molecular formula of the light-absorbing material in Example 7 is shown below: (CP dimer II-3).

[0118] The specific synthesis steps for CP dimer II-3 are the same as those for CP dimer II-1, with the following differences: Starting from step (i), the starting material 2-bromo-4-tert-butyl-1-nitrobenzene was replaced with 2-bromo-4-trifluoromethyl-1-nitrobenzene, and the 1,8-diethynyl-3,6-di-tert-butylcarbazole in step (v) was replaced with 1,8-diethynyl-3,6-bistrifluoromethylcarbazole, yielding product CP dimer II-3. The mass spectrometry (MS) result of the product was: 1364.0440 [M + ].

[0119] The molecular formula of the light-absorbing material in Example 8 is shown below: (CP dimer II-4).

[0120] The specific synthesis steps for CP dimer II-4 are the same as those for CP dimer II-1, with the following differences: Starting from step (i), the starting material 2-bromo-4-tert-butyl-1-nitrobenzene was replaced with 2-bromo-4-methoxy-1-nitrobenzene, and the 1,8-diethynyl-3,6-di-tert-butylcarbazole in step (v) was replaced with 1,8-diethynyl-3,6-dimethoxycarbazole, yielding the product CP dimer II-4. The mass spectrometry (MS) result of the product was: 1136.1831 [M + ].

[0121] CP dimer I-2 and CP dimer II-1 were formulated into a 1×10⁻⁶ solution. -6 A xylene solution of mol / L was used to measure the UV-Vis absorption spectrum on a Shimidzu UV-2600 UV-Vis spectrophotometer. Comparative compounds were also used. (Ref 1) UV-Vis absorption spectra of xylene solutions at the same concentration, results refer to Figures 1 to 3 As shown, where, Figure 1 The UV-Vis absorption spectrum of CP dimer I-2 is shown. Figure 2 The UV-Vis absorption spectrum of CP dimer II-1 is shown. Figure 3 This is the UV-Vis absorption spectrum of compound Ref1.

[0122] according to Figures 1 to 3 It can be seen that CP dimer I 2 and CP dimer II The absorption band of Ref1 continuously covers 700 nm to 1200 nm, while Ref1 shows an absorption trough at approximately 900 nm. Furthermore, the light-absorbing material of this application also exhibits a significant absorption peak in the range of 300 nm to 500 nm, enabling it to absorb light from the ultraviolet to the blue light band simultaneously. Therefore, the light-absorbing material of this application not only continuously covers the entire near-infrared band (780 nm to 1100 nm) but also simultaneously achieves absorption from the ultraviolet to the blue light band. As a light-absorbing material, the solution of this application can achieve synergistic absorption of multiple light bands through a single material and possesses wide-band infrared light absorption capability, thus showing broad and significant application prospects as an infrared light-absorbing material.

[0123] Furthermore, in comparison Figure 1 and Figure 2 It can be seen that when the light-absorbing material is polymerized by single bond, the light absorption intensity is greater in the range of 700 nm to 1200 nm. When the light-absorbing material is polymerized by fusion, its infrared light absorption is further extended to the 1400 nm band, and the absorption band coverage is wider.

[0124] This application provides various optical films and their preparation methods through application examples 1 to 8, wherein: The preparation steps of the optical film provided in Application Example 1 are as follows: (1) Provide the resin system as shown in Table 1. Table 1 Ingredient name Supplier and Product Code mass content resin acrylic resin prepolymer Kyoeisha Chemical UA-306H 28% monomer Dipentaerythritol hexaacrylate Commercial reagents 8% Leveling agent / BYK-3931P 1% dispersant / BYK-2013 1% Initiator 2,4,6-Trimethylbenzoyldiphenylphosphine oxide (TPO) Commercial reagents 2% solvent Ethyl acetate Commercial reagents 60% (2) Dissolve the light-absorbing material CP dimer I-1 in the resin system shown in Table 1. The mass ratio of CP dimer I-1 to the resin system is 0.5% to obtain the coating system.

[0125] (3) The coating system is applied to a polyethylene terephthalate (PET) substrate, and after leveling, drying and UV curing, the corresponding optical film is obtained, and the thickness of the optical film is 5 μm.

[0126] The optical films provided in Application Examples 2 to 8 are prepared using the same methods as in Application Example 1, except that the light-absorbing material is replaced with CP dimer I. 2. CP dimer I 3. CP dimer I 4. CP dimer II 1. CP dimer II 2. CP dimer II 3 and CP dimer II 4.

[0127] This application also provides two contrasting optical films by applying Comparative Examples 1 to 2.

[0128] The preparation method of the comparative optical film provided in Comparative Example 1 is the same as that of the optical film in Application Example 1, except that the light-absorbing material is replaced with comparative compound Ref1.

[0129] The preparation method of the comparative optical film provided in Comparative Example 2 is the same as that of the optical film in Application Example 1, except that the light-absorbing material is replaced with comparative compound Ref2, wherein the chemical formula of comparative compound Ref2 is as follows: .

[0130] The light transmittance of the optical films provided in Application Examples 1 to 8 and the comparative optical films provided in Application Comparative Examples 1 to 2 were tested, and the results are shown in Table 2.

[0131] Table 2 400nm 800nm 900nm 1000nm 1100nm 1200nm 1300nm Application Example 1 15.49% 32.69% 25.95% 10.24% 36.75% 82.05% 36.53% Application Example 2 13.66% 43.55% 21.86% 15.02% 9.39% 41.26% 84.16% Application Example 3 12.87% 38.56% 23.45% 11.63% 28.62% 49.25% 41.23% Application Example 4 17.34% 42.19% 28.71% 18.58% 21.90% 51.27% 56.74% Application Example 5 19.23% 47.64% 26.49% 24.58% 23.97% 28.07% 22.69% Application Example 6 12.37% 33.67% 25.89% 27.02% 31.52% 22.14% 28.33% Application Example 7 18.45% 69.12% 22.81% 28.46% 26.34% 19.03% 20.45% Application Example 8 14.99% 62.33% 22.67% 33.45% 29.15% 24.63% 23.78% Application Comparative Example 1 98.47% 37.27% 58.22% 11.07% 97.14% 100% 100% Application Comparative Example 2 25.93% 100% 100% 100% 100% 100% 100% As can be seen from the data in Table 2, the optical films provided in Application Examples 1 to 8, compared to the comparative optical films provided in Application Examples 1 to 2, employ a porphyrin derivative polymer structure. Their infrared absorption band continuously covers the 900 nm to 1100 nm band, while also exhibiting high absorption for light in the 400 nm band. Furthermore, the light-absorbing material using a single-bonded porphyrin derivative polymer structure exhibits high absorption at 800 nm; while the absorption band of the fused porphyrin derivative polymer structure is further extended to the 1300 nm band.

[0132] See Figures 4 to 5 This application embodiment also provides a display panel 100, which includes the optical film 20 described in the foregoing embodiments.

[0133] When the display panel 100 of this application embodiment has the optical film 20 of the aforementioned embodiment, it can prevent infrared light from entering the device, thereby blocking heat from entering the display panel 100.

[0134] In some embodiments, the display panel 100 further includes a light-emitting component 10, and an optical film 20 is located on the light-emitting side of the light-emitting component 10.

[0135] In some embodiments, the display panel 100 further includes a remaining functional layer 30, which includes at least one of a hardened coating and an anti-reflection coating, and the remaining functional layer 30 is located on the light-emitting side of the light-emitting component 10.

[0136] In some embodiments, the remaining functional layers 30 are located on the side of the optical film 20 away from the light-emitting component 10, but are not limited thereto.

[0137] The above provides a detailed description of a light-absorbing material, optical film, and display panel provided in the embodiments of this application. Specific examples have been used to illustrate the principles and implementation methods of this application. The description of the above embodiments is only for the purpose of helping to understand the method and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. A light-absorbing material, characterized in that, The structural formula of the light-absorbing material is shown in formula (1): （1）； When multiple Ar appear simultaneously, they may be the same or different from each other, and the structural formula of Ar is shown in equation (2): （2）； R1 to R6 are independently selected from hydrogen atoms, halogen atoms, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 10 carbon atoms, substituted or unsubstituted thio groups, cyano groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryl groups having 1 to 20 cyclic atoms, and substituted or unsubstituted heteroaryl groups having 1 to 20 cyclic atoms. One or more combinations thereof; Indicates the connection site with L; a and b are selected from 0, 1, or 2; c, d, e, and f are selected from 0, 1, 2, or 3; L is selected from one or more combinations of single bond, substituted or unsubstituted alkyl with 1 to 10 carbon atoms, substituted or unsubstituted alkenyl with 1 to 10 carbon atoms, substituted or unsubstituted alkoxy with 1 to 10 carbon atoms, substituted or unsubstituted thiol, substituted or unsubstituted amino, substituted or unsubstituted aryl with 1 to 20 ring atoms, and substituted or unsubstituted heteroaryl with 1 to 20 ring atoms; m is selected from 0 or 1, and when m=0, two adjacent Ar are either fused or screwed together; n is any integer from 1 to 10; The substituted or unsubstituted substituents in R1 to R6 and L are independently selected from one or more combinations of deuterium, cyano, isocyano, nitro, halogen atom, alkyl containing 1 to 20 carbon atoms, heterocyclic group having 3 to 20 ring atoms, aryl group having 6 to 20 ring atoms, heteroaryl group having 5 to 20 ring atoms, -NR'R'', silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halocarbamoyl, formyl, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl, and trifluoromethyl. In -NR'R'', R' and R'' are independently selected from one or more combinations of H, deuterium atom, cyano, isocyano, nitro, halogen atom, alkyl with 1 to 10 carbon atoms, heterocyclic group with 3 to 20 carbon atoms, aryl with 6 to 20 ring atoms, and heteroaryl with 5 to 20 ring atoms.

2. The light-absorbing material according to claim 1, characterized in that, m=0, and the light-absorbing material has the structure shown in formula (1-1): （1-1）。 3. The light-absorbing material according to claim 1, characterized in that, m=1, and the light-absorbing material has the structure shown in formula (1-2): （1-2）。 4. The light-absorbing material according to claim 2 or 3, characterized in that, R1 to R6 are independently selected from one or more combinations of groups containing F atoms, alkyl groups containing 2 or more carbon atoms, and groups containing phenyl groups.

5. The light-absorbing material according to any one of claims 1 to 3, characterized in that, The light-absorbing material is selected from compounds represented by any of the following structural formulas: I-1 I-2 I-3 I-4 II-1 II-2 II-3 II-4.

6. The light-absorbing material according to any one of claims 1 to 3, characterized in that, The light-absorbing material has an absorption spectrum that continuously covers the near-infrared band from 700 nm to 1400 nm.

7. An optical film, characterized in that, The material of the optical film includes the light-absorbing material as described in any one of claims 1 to 6.

8. The optical film according to claim 7, characterized in that, The optical film further includes a substrate, the light-absorbing material is dispersed in the substrate, and the mass ratio of the light-absorbing material to the mass of the substrate is (0.005~0.08):

1.

9. The optical film according to claim 7 or 8, characterized in that, The optical film has a transmittance of less than 50% for light in the 900 nm to 1100 nm wavelength range.

10. A display panel, characterized in that, The display panel includes the optical film as described in claim 8 or 9.

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