An aromatic compound and use thereof

Abstract

This invention provides an aromatic compound and its applications. The aromatic compound comprises a structure having Formula I. By designing the specific structure of the aromatic compound, employing a double-boron structure on the parent core, and designing tunable peripheral groups, this invention achieves a wider range of spectral emission. This structure, on the one hand, lowers the HOMO energy level of the material, reducing hole trapping and making the transport of holes and electrons in the device more balanced, thus improving device performance; on the other hand, the double-boron structure can narrow the full width at half maximum (FWHM), improving PLQY and contributing to improved device efficiency. Through ingenious molecular design, this invention provides an aromatic compound that is highly suitable for application in OLEDs and enhances device performance.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials technology, specifically relating to an aromatic compound and its applications. Background Technology

[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them ideal for fabrication on flexible substrates, allowing for the design and production of aesthetically pleasing and stylish optoelectronic products, offering unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, and organic sensors. OLEDs, in particular, have developed rapidly and have already achieved commercial success in the information display field. OLEDs can provide highly saturated red, green, and blue colors, and full-color displays made with them do not require an additional backlight, offering advantages such as vibrant colors, thinness, and flexibility.

[0003] The core of an OLED device is a thin-film structure containing various organic functional materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, as well as light-emitting host materials and light-emitting guest materials (dyes). When an electric current is applied, electrons and holes are injected and transported to the light-emitting region, where they recombine, thereby generating excitons and emitting light.

[0004] Various organic materials have been developed and combined with unique device structures to improve carrier mobility, regulate carrier balance, break through electroluminescence efficiency barriers, and delay device decay. For quantum mechanical reasons, common fluorescent emitters primarily utilize singlet excitons generated when electrons and holes combine to emit light, and are still widely used in various OLED products. Some metal complexes, such as iridium complexes, can simultaneously utilize triplet and singlet excitons for light emission, and are called phosphorescent emitters, with energy conversion efficiencies up to four times higher than traditional fluorescent emitters. Thermally excited delayed fluorescence (TADF) technology promotes the transition from triplet to singlet excitons, achieving high luminescence efficiency without the use of metal complexes, while still effectively utilizing triplet excitons. Thermally excited sensitized fluorescence (TASF) technology uses materials with TADF properties to sensitize the emitter through energy transfer, also achieving high luminescence efficiency.

[0005] In 2016, Professor Takuji Hatakeyama of Japan proposed a design strategy for TADF (Thermally Activated Delayed Fluorescence) materials based on BN resonance (Adv. Mater. 2016, 28, 2777-2781). These materials, composed of boron atoms, nitrogen atoms, and multiple benzene rings, exhibit a rigid polycyclic aromatic hydrocarbon structure and high fluorescence quantum yield. In particular, compared to traditional blue fluorescent dyes, they have a narrower spectrum and higher color purity, showing significant advantages. However, due to their particularly planar and rigid structure, they are prone to molecular stacking and exciton annihilation, resulting in a severe efficiency roll-off. Therefore, there is still considerable room for improvement in the luminescence performance of this type of organic electroluminescent material.

[0006] As OLED products gradually enter the market, people have increasingly higher requirements for their performance. Current OLED materials and device structures cannot fully address the issues of efficiency, lifespan, and cost in OLED products. Therefore, there is an urgent need in this field to develop more diverse and higher-performance organic materials for application in organic electroluminescent devices, enabling these devices to achieve better luminescence and longer lifespans. Summary of the Invention

[0007] To address the shortcomings of existing technologies, the present invention aims to provide an aromatic compound and its applications. This invention designs the specific structure of the aromatic compound, employing a double-B structure on the parent core and designing tunable peripheral groups to achieve a wider spectral range of luminescence. This structure, on the one hand, lowers the HOMO energy level of the material, reducing hole trapping and creating a more balanced transport of holes and electrons in the device, thus improving device performance; on the other hand, the double-B structure can narrow the full width at half maximum (FWHM), improving PLQY and contributing to increased device efficiency. Through ingenious molecular design, the aromatic compound provided by this invention is highly suitable for application in OLEDs and for enhancing device performance.

[0008] To achieve this objective, the present invention adopts the following technical solution:

[0009] In a first aspect, the present invention provides an aromatic compound having a structure as shown in Formula I:

[0010]

[0011] Among them, ring A and ring B are each independently selected from one of substituted or unsubstituted C6-C60 aromatic rings and substituted or unsubstituted C2-C60 heteroaromatic rings;

[0012] The substituents in ring A and ring B are each independently selected from halogens, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, unsubstituted or R'-substituted C6-C30 heteroarylsilyl groups, unsubstituted or R'-substituted C1-C20 alkylamino groups, cyano groups, nitrate groups, etc. The substituted group comprises any one of the following: aryl, amino, hydroxyl, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; wherein the substituted substituents are not connected to each other or are linked to form a ring by chemical bonds; wherein each substituted substituent is independently not connected to or linked to an adjacent ring structure by chemical bonds.

[0013] Y1 and Y2 are each independently selected from any one of CR1R2, SiR3R4, NR5, Se, O, or S.

[0014] M is selected from single bonds, CR6R7, SiR8R9, O, S, Se, NR 10 Any one of them;

[0015] X1 to X7 are each independently selected from N or CR 11 Furthermore, X6 is not connected to ring B to form a ring;

[0016] R'、R1-R 11 Selected from hydrogen atoms, halogens, substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 heteroarylsilyl groups, substituted or unsubstituted C1-C20 alkylamino groups, cyano groups, nitro groups, etc. The amino group, hydroxyl group, substituted or unsubstituted C6-C30 arylamino group, substituted or unsubstituted C3-C30 heteroarylamino group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C3-C30 heteroaryloxy group, substituted or unsubstituted C6-C60 aryl group, and substituted or unsubstituted C3-C60 heteroaryl group; and at least two any two adjacent R groups between R1 and R2, R3 and R4, R6 and R7, and R8 and R9. 11 Between R 11 They are either not connected or linked by chemical bonds to form a ring, R1-R11 Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds.

[0017] R'、R1-R 11 The substituents described herein are each independently selected from any one or a combination of at least two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; the substituents are not connected to each other or are linked to form a ring by chemical bonds; the substituents are each independently not connected to adjacent ring structures or are linked to form a ring by chemical bonds.

[0018] Adjacent R's are either not connected to each other or are linked to each other by chemical bonds to form a ring; each R' is independently not connected to its adjacent ring structure or is linked to each other by chemical bonds to form a ring.

[0019] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents (at least two), they can be the same or different substituents. The same expression used below has the same meaning, and the selection range of substituents is as shown above, and will not be repeated one by one.

[0020] This invention designs specific structures for aromatic compounds, employing a double-boron structure on the core of the aromatic compound and designing tunable peripheral groups to achieve a wider spectral range of luminescence. This structure lowers the HOMO energy level of the material, reducing hole trapping and creating a more balanced transport of holes and electrons in the device, thus improving device performance. Furthermore, the double-boron structure combined with M-bonds enhances molecular rigidity, effectively suppressing excited-state vibrations, narrowing the full width at half maximum (FWHM), and improving PLQY, which is beneficial for improving device efficiency. Through ingenious molecular design, this invention provides aromatic compounds highly suitable for application in OLEDs and for enhancing device performance.

[0021] It should be noted that in this invention, M represents a single bond, and a ring containing M is a five-membered ring with the following structural formula: M represents CR6R7, SiR8R9, O, S, Se, NR 10 When any of the following conditions are met, the ring containing M is a six-membered ring, and its structural formula is:

[0022] It should be noted that in the present invention, for the convenience of description, the possible functions of each group / feature are described separately, but this does not mean that these groups / features act independently. In fact, the reason for obtaining good performance is essentially the optimized combination of the entire molecule, which is the result of the synergistic effect between each group, rather than the effect of a single group.

[0023] In the present invention, for the expression of chemical elements, unless otherwise specified, it includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) includes 12 C, 13 C, etc.

[0024] In the present invention, unless otherwise specified, the heteroatoms of heteroaryl are selected from atoms or atomic groups of N, O, S, P, B, Si or Se, preferably N, O, S.

[0025] In the present invention, the expression of the ring structure crossed by “—” or “------” means that the connection site is at any position on the ring structure where bonding can occur.

[0026] In the present invention, the expression Ca-Cb represents that the group has a carbon atom number of a-b. Unless otherwise specified, generally speaking, the carbon atom number does not include the carbon atom number of substituents.

[0027] In the present invention, “independently of each other” means that when the subject has multiple ones, they can be the same or different from each other.

[0028] In the present invention, the C6-C60 aryl groups can all be aryl groups such as C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C36, C42, C48, C50, C54 or C60, etc. Preferably, C6-C20 aryl groups, including monocyclic aryl groups or fused-ring aryl groups. The monocyclic aryl group means that the group contains at least 1 phenyl group. When it contains at least 2 phenyl groups, the phenyl groups are connected by single bonds. Exemplarily, it includes but is not limited to: phenyl, biphenyl, terphenyl, etc.; the fused-ring aryl group means that the group contains at least 2 aromatic rings, and the aromatic rings are fused to each other by sharing two adjacent carbon atoms. Exemplarily, it includes but is not limited to: naphthyl, naphthylphenyl, phenylnaphthyl, anthryl, phenanthryl, indenyl, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl or naphthacenyl, etc.; the groups listed above include all their feasible connection modes.

[0029] In this invention, the C3-C60 heteroaryl groups can be heteroaryl groups of C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C36, C42, C48, C50, C54, or C60, including monocyclic heteroaryl groups or fused-ring heteroaryl groups. A monocyclic heteroaryl group means that the molecule contains at least one heteroaryl group. When the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and other groups are connected by a single bond, exemplarily including but not limited to: furanyl, thiophene, pyrrole, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, oxazolyl, thiazolyl, imidazole, etc. The term "fused-ring heteroaryl" refers to a molecule containing at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring), and the two share two adjacent atoms fused together in a group. Examples include, but are not limited to: benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl and its derivatives (N-phenylcarbazoleyl, N-naphthylcarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, azacarbazoleyl, etc.), acridineyl, phenazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, pyridinylpyrimidinyl, pyridopyrazinyl, etc.; the aforementioned groups include all possible linkages.

[0030] The C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, or C300, etc.) arylamino groups described in this invention are groups formed by replacing at least one H on the -NH2 group with one of the aryl groups listed above. Exemplary examples include, but are not limited to, phenylamino, biphenylamino, naphthylamino, etc.

[0031] The C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, or C30, etc.) heteroarylamino groups described in this invention are groups formed by replacing at least one H on the -NH2 group with the heteroaryl groups listed above. Exemplary examples include, but are not limited to, pyrroloamino, pyrimidinylamino, furanylamino, etc.

[0032] In this invention, the C1-C20 straight-chain or branched alkyl groups can be straight-chain or branched alkyl groups of C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc., and are further preferably C1-C10 straight-chain or branched alkyl groups; exemplary, including but not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl or n-decyl, etc.

[0033] Specific examples of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkoxy groups can be exemplified by the monovalent groups obtained by connecting the above-mentioned straight-chain or branched alkyl groups with O.

[0034] In this invention, the C3-C20 cycloalkyl groups can all be cycloalkyl groups of C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C20, etc.; exemplary, including but not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0035] In this invention, the C2-C20 alkenyl groups can all be alkenyl groups of C2, C4, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C20, etc.; exemplary, including but not limited to: vinyl, propenyl, butenyl, etc.

[0036] Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryloxy groups can be exemplified by the monovalent group obtained by attaching the aforementioned aryl group to O; specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryloxy groups can be exemplified by the monovalent group obtained by attaching the aforementioned aryl group to the aforementioned heteroatom.

[0037] The C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, or C20, etc.) alkylamino group is a monovalent group formed when at least one H on the -NH2 group is replaced by one of the straight-chain or branched alkyl groups listed above.

[0038] In this invention, the halogen includes fluorine, chlorine, bromine, or iodine; the same descriptions used below have the same meaning.

[0039] In this invention, "halogenated" means that at least one H in the group is replaced by a halogen (fluorine, chlorine, bromine or iodine).

[0040] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. The purpose and beneficial effects of the present invention can be better achieved and realized through the following preferred technical solutions.

[0041] As a preferred embodiment of the present invention, ring A and ring B each independently have the structure shown in formula a or formula b:

[0042]

[0043] Among them, Q1-Q8 are each independently selected from CR 12 Or N;

[0044] In Q1-Q8, R 12 Each is independently selected from hydrogen atoms, halogens, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, unsubstituted or R'-substituted C6-C30 heteroarylsilyl groups, unsubstituted or R'-substituted C1-C20 alkylamino groups, cyano groups, nitro groups, and amino groups. The R12 is any one of the following: hydroxyl, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; two adjacent R12 are not connected or are linked to each other by chemical bonds to form a ring; each R12 is independently not connected to the adjacent ring structure or is linked to the adjacent ring structure by chemical bonds to form a ring.

[0045] Xa is selected from CR 16 R 17 SiR 18 R 19 , O, S, Se, NR 20 Any one of them.

[0046] R 16 -R 20Selected from any one of hydrogen atoms, halogens, substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 heteroarylsilyl groups, substituted or unsubstituted C1-C20 alkylamino groups, cyano groups, nitro groups, amino groups, hydroxyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C3-C30 heteroarylamino groups, substituted or unsubstituted C6-C30 aryloxy groups, substituted or unsubstituted C3-C30 heteroaryloxy groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups; The R 16 With R 17 Between, R 18 With R 19 They are either not connected to each other or linked together by chemical bonds to form a ring;

[0047] Preferably, R in Q1-Q8 12 Each of the substituents is independently selected from any one of hydrogen atom, halogen, cyano group, substituted or unsubstituted C1-C20 straight-chain or branched alkyl group, substituted or unsubstituted C2-C20 alkenyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C30 arylamino group, substituted or unsubstituted C3-C30 heteroarylamino group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group; each of the substituted substituents is independently selected from at least one of C1-C10 alkyl group, C2-C10 alkenyl group, C6-C15 aryl group, and C3-C15 heteroaryl group.

[0048] Two adjacent R 12 The R are either not connected or linked by chemical bonds to form a ring; 12 Each ring is independent and not connected to adjacent ring structures or is linked to form a ring by chemical bonds;

[0049] Preferably, X a Choose from O or S.

[0050] Preferably, ring A and ring B each have the structure shown in the following formula:

[0051]

[0052]

[0053] Among them, R a1 -Ra7 Each is independently selected from halogens, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, unsubstituted or R'-substituted C6-C30 heteroarylsilyl groups, unsubstituted or R'-substituted C1-C20 alkylamino groups, cyano groups, nitro groups, amino groups, and hydroxyl groups. The following are possible interpretations: unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; the substituted substituents are not connected to each other or are linked to form a ring by chemical bonds; each substituted substituent is independently not connected to or linked to an adjacent ring structure by chemical bonds.

[0054] n1 and n7 represent integers from 0 to 4 (e.g., 0, 1, 2, 3, or 4), and n2-n6 represent integers from 0 to 6 (e.g., 0, 1, 2, 3, 4, 5, or 6).

[0055] Preferably, R a1 -R a7 Each of the following is independently selected from any one of substituted or unsubstituted C1-C5 alkyl, substituted or unsubstituted C2-C5 alkenyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C12 heteroaryl, and substituted or unsubstituted C6-C12 arylamino, wherein the substituent is selected from at least one of methyl, ethyl, propyl, butyl, phenyl, naphthyl, or carbazole; the two adjacent R a1 They are either not connected or linked by chemical bonds to form a ring; two adjacent Rs a1 Between, two adjacent R a2 Between, two adjacent R a3 Between, two adjacent R a4 Between, two adjacent R a5 Between, two adjacent R a6 The R are either not connected or linked by chemical bonds to form a ring; a1 -R a6 Each ring is independent and not connected to adjacent ring structures or is linked to form a ring by chemical bonds;

[0056] As a preferred embodiment of the present invention, Y1 and Y2 are each independently selected from any one of CR1R2, SiR3R4, NR5, O or S, preferably any one of CR1R2, NR5 or O, and more preferably any one of NR5, S or O.

[0057] Preferably, at least one of Y1 and Y2 is selected from NR5.

[0058] Preferably, Y1 and Y2 are each independently selected from NR5.

[0059] Preferably, either Y1 or Y2 is selected from NR5, and the other is selected from O.

[0060] Preferably, each of R1-R5 is independently selected from any one of substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C2-C10 alkenyl groups, substituted or unsubstituted C1-C20 alkoxy groups, cyano groups, substituted or unsubstituted C6-C20 aryl groups, and substituted or unsubstituted C3-C20 heteroaryl groups; R1 and R2, and R3 and R4 are not connected or are linked to each other by chemical bonds to form a ring, and each of R1-R5 is independently not connected to the adjacent ring structure or is linked to the adjacent ring structure by chemical bonds to form a ring;

[0061] The substituents in R1-R5 are each independently selected from any one or a combination of at least two of the following: C1-C6 straight-chain or branched alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C6-C12 aryl, C3-C12 heteroaryl, and C6-C10 arylamino; the substituents are not connected to each other or are linked to form a ring by chemical bonds; and each substituent is independently not connected to the adjacent ring structure or is linked to form a ring by chemical bonds.

[0062] Preferably, each of R1-R4 is independently selected from any one of C1-C5 straight-chain or branched alkyl, C2-C5 alkenyl, C6-C12 aryl, and C3-C12 heteroaryl; R1 and R2, and R3 and R4 are not connected or are connected to each other by chemical bonds to form a ring, and each of R1-R5 is independently not connected to the adjacent ring structure or is connected to each other by chemical bonds to form a ring.

[0063] Preferably, R5 is selected from groups having the following structure:

[0064]

[0065] Among them, R Y1 -R Y9Each is independently selected from any one or a combination of at least two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0066] m1 represents an integer from 0 to 5 (e.g., 0, 1, 2, 3, 4, or 5), m2 represents an integer from 0 to 4 (e.g., 0, 1, 2, 3, or 4), and m3 represents an integer from 0 to 7 (e.g., 0, 1, 2, 3, 4, 5, 6, or 7).

[0067] Preferably, R Y1 -R Y9 Each is independently selected from any one of C1-C6 straight-chain or branched alkyl, -SiH(CH3)2, C6-C12 aryl, C3-C12 heteroaryl, and C6-C10 arylamino; adjacent R Y1 Between, adjacent R Y3 Between, adjacent R Y4 Between, R Y5 -R Y7 Between, R Y8 -R Y9 They are either not connected or linked by chemical bonds to form a ring; R Y1 -R Y9 Each ring is independent and not connected to adjacent ring structures or is linked to form a ring by chemical bonds;

[0068] As a preferred embodiment of the present invention, M represents a single bond, CR6R7, SiR8R9, O, S, Se, or NR. 10 Any one of them:

[0069] The R6-R 10 Each is independently selected from any one of the following: substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C2-C10 alkenyl groups, substituted or unsubstituted C1-C20 alkoxy groups, cyano groups, substituted or unsubstituted C6-C20 aryl groups, and substituted or unsubstituted C3-C20 heteroaryl groups; R6 and R7, and R8 and R9, are not connected or are linked by chemical bonds to form a ring, R6-R 10 Each ring is independent and not connected to adjacent ring structures or is linked to form a ring by chemical bonds;

[0070] The R6-R 10The substituents described herein are each independently selected from any one or at least a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; the substituents are not connected to each other or are linked to form a ring by chemical bonds; the substituents are each independently not connected to the adjacent ring structure or are linked to form a ring by chemical bonds.

[0071] Preferably, the R6-R 10 The substituents described herein are each independently selected from any one or a combination of at least two of the following: C1-C6 straight-chain or branched alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C6-C12 aryl, C3-C12 heteroaryl, and C6-C10 arylamino; the substituents are not connected to each other or are linked to form a ring by chemical bonds; and each substituent is independently not connected to an adjacent ring structure or is linked to form a ring by chemical bonds.

[0072] Preferably, M represents any one of a single bond, CR6R7, O, S, and Se; more preferably, a single bond or CR6R7; and even more preferably, a single bond.

[0073] R6-R7 are selected from any one or a combination of at least two of C1-C10 straight-chain or branched alkyl, C6-C12 aryl, C3-C12 heteroaryl, and C6-C10 arylamino; the substituted substituents are not connected to each other or are linked to form a ring by chemical bonds; each substituted substituent is independently not connected to the adjacent ring structure or is linked to form a ring by chemical bonds.

[0074] As a preferred embodiment of the present invention, X1 to X7 are CR 11 .

[0075] Preferably, the R 11Selected from any one of hydrogen atoms, halogens, substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 heteroarylsilyl groups, substituted or unsubstituted C1-C20 alkylamino groups, cyano groups, nitro groups, amino groups, hydroxyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C3-C30 heteroarylamino groups, substituted or unsubstituted C6-C30 aryloxy groups, substituted or unsubstituted C3-C30 heteroaryloxy groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups; at least two any two adjacent R groups. 11 They are either not connected or linked by chemical bonds to form a ring, R 11 It is not connected to adjacent ring structures or is linked to them by chemical bonds to form a ring.

[0076] Preferably, the R 11 It is selected from any one of hydrogen atom, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C6-C20 aryl, and C3-C20 heteroaryl, more preferably any one of hydrogen atom, C1-C5 straight-chain or branched alkyl, C6-C12 aryl, and C3-C10 heteroaryl, and even more preferably any one of methyl, ethyl, tert-butyl, phenyl, or naphthyl.

[0077] Preferably, X1, X3, X4, X6, and X7 are CH, and X2 and X5 are each independently CR. 11 R 11 It is selected from any one of hydrogen atom, methyl, ethyl, tert-butyl, phenyl or naphthyl.

[0078] As a preferred embodiment of the present invention, the aromatic compound comprises a structure having the structure shown in Formula I-1, Formula I-2, Formula I-3, Formula I-4 or Formula I-5:

[0079]

[0080]

[0081] Among them, Q1-Q 16 Each independently selected from CR 12 ;

[0082] R 12 It has the same definition as above;

[0083] Y1, Y2, and X1 to X7 each have the same definitions as above.

[0084] As a preferred embodiment of the present invention, the aromatic compounds include the following compounds:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] In a second aspect, the present invention provides an application of an aromatic compound as described in the first aspect, said aromatic compound being used to prepare organic electronic devices.

[0104] Preferably, the organic electronic device includes any one or a combination of at least two of the following: organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper.

[0105] Preferably, the aromatic compound is used as a light-emitting layer material in organic electronic devices, and more preferably as a light-emitting dye in the light-emitting layer.

[0106] Thirdly, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprising at least one aromatic compound as described in the first aspect.

[0107] Preferably, the organic layer includes a light-emitting layer, wherein the light-emitting layer includes at least one aromatic compound as described in the first aspect.

[0108] Preferably, the light-emitting layer comprises a host material and a light-emitting dye, wherein the light-emitting dye comprises at least one aromatic compound as described in the first aspect.

[0109] An OLED includes a first electrode and a second electrode, and an organic material layer located between the electrodes. This organic material layer can be further divided into multiple regions. For example, the organic material layer may include a hole transport region, a light-emitting layer, and an electron transport region.

[0110] In specific embodiments, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, thin-film transistors (TFTs) can also be incorporated into the substrate used for displays.

[0111] The first electrode can be formed by sputtering or depositing the material to be used as the first electrode on a substrate. When the first electrode is used as the anode, it can be a transparent conductive oxide material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode is used as the cathode, it can be a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0112] Organic material layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used as organic material layers can be small organic molecules, large organic molecules, polymers, and combinations thereof.

[0113] The hole transport region is located between the anode and the emissive layer. The hole transport region can be a single-layer hole transport layer (HTL), including a single-layer hole transport layer containing only one compound or a single-layer hole transport layer containing multiple compounds. Alternatively, the hole transport region can be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the emissive layer.

[0114] The material for the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives; wherein, aromatic amine derivatives include compounds shown below HT-1 to HT-51; or any combination thereof.

[0115]

[0116]

[0117]

[0118]

[0119] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can be one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1 to HI-3 described below; it can also be one or more compounds of HT-1 to HT-51 doped with one or more compounds of HI-1 to HI-3 described below.

[0120]

[0121] The emissive layer includes luminescent dyes (i.e., dopants) that can emit different wavelengths of light, and may also include a host material. The emissive layer can be a monochromatic emissive layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that can simultaneously emit different colors such as red, green, and blue.

[0122] Depending on the technology used, the light-emitting layer material can be various, including fluorescent electroluminescent materials, phosphorescent electroluminescent materials, and thermally activated delayed fluorescence materials. An OLED device can employ a single light-emitting technology or a combination of different technologies. These different light-emitting materials, categorized by technology, can emit light of the same color or different colors.

[0123] In one aspect of the invention, the light-emitting layer employs fluorescent electroluminescence technology. The fluorescent dopant in the light-emitting layer may be selected from, but not limited to, one or more combinations of M1 to M265 listed above.

[0124] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The host material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-117.

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The phosphorescent dopant of the light-emitting layer may be selected from, but is not limited to, one or more combinations of BPD-1 to BPD-16 listed below.

[0132]

[0133]

[0134] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The phosphorescent dopant of the light-emitting layer may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-60 listed below.

[0135]

[0136]

[0137]

[0138] Where D represents deuterium.

[0139] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light-emitting layer. The electron blocking layer may employ, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-75 to PH-117 described above; or a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-75 to PH-117 may be employed.

[0140] The OLED organic material layer may also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including single-layer electron transport layers containing only one compound and single-layer electron transport layers containing multiple compounds. Alternatively, the electron transport region can be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0141] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0142]

[0143]

[0144]

[0145]

[0146] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer may employ, but is not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-74; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-74 may be employed.

[0147] Organic electroluminescent devices may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg or Yb.

[0148] Fourthly, the present invention provides a display device, characterized in that the display device includes an organic electroluminescent device as described in the third aspect.

[0149] Compared with the prior art, the present invention has the following beneficial effects:

[0150] This invention designs specific structures for aromatic compounds, employing a double-B structure on the parent core and designing tunable peripheral groups to achieve a wide range of spectral emission. This structure lowers the HOMO level of the material, reducing hole trapping and creating a more balanced transport of holes and electrons in the device, thus improving device performance. Furthermore, the double-B structure narrows the full width at half maximum (FWHM), increasing PLQY and contributing to improved device efficiency. Through ingenious molecular design, this invention provides aromatic compounds highly suitable for OLED applications and enhancing device performance. Detailed Implementation

[0151] To facilitate understanding of the present invention, the following embodiments are provided. Those skilled in the art should understand that these embodiments are merely illustrative and should not be construed as limiting the scope of the invention.

[0152] The preparation methods of the compounds of Formula I of this invention include, but are not limited to, the following synthesis methods. Those skilled in the art can also make conventional adjustments to the preparation methods according to actual needs. Compounds with the structure shown in Formula I obtained by other methods are also within the protection scope of this invention.

[0153] The present invention provides illustrative methods for synthesizing representative compounds through the following synthetic examples. The solvents and reagents used in the synthetic examples can be purchased from the chemical product market or customized.

[0154] In one specific implementation, the core structure can be obtained through the following synthetic steps:

[0155]

[0156] Among them, rings A, B, Y1, Y2, X1-X7, and M have the same defined range as Equation I; Hal 1 Hal 2 Hal 3 Hal 4 Each is an independent halogen, and is further preferably F, Br or I.

[0157] The specific preparation methods of the polycyclic aromatic compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0158] The structural analysis of intermediates and compounds in this invention was performed using an ABSCIEX mass spectrometer (4000QTRAP).

[0159] Synthesis Example 1

[0160] This synthetic example provides compound M7 and its synthetic method, which is as follows:

[0161]

[0162] (1) Synthesis of intermediate M7-1:

[0163] At room temperature, compound M7-0 (20.0 g), compound A1 (16.3 g), Pd2(dba)3 (2.6 g), tri-tert-butylphosphide tetrafluoroborate (1.7 g), sodium tert-butoxide (11.1 g), and toluene (500 mL) were added to a 1 L single-necked flask. The mixture was purged with nitrogen three times and heated to 100 °C overnight. The reaction solution was cooled to room temperature, concentrated, extracted with dichloromethane, washed with plenty of water, dried, and concentrated for column chromatography (PE:DCM = 2:1, v / v) to obtain the crude product, which was directly added to the next step without further purification.

[0164] The molecular ion mass [M] of intermediate M7-1 was determined by mass spectrometry analysis. + H] + 547.33 (Theoretical value: 546.32).

[0165] (2) Synthesis of intermediate M7-2:

[0166] At room temperature, the crude intermediate M7-1 was added to a 1L single-necked flask, followed by 300mL of tetrahydrofuran and 17.3mL of concentrated hydrochloric acid (10mol / L). The mixture was heated to reflux and stirred overnight. The organic phase was then concentrated and subjected to column chromatography (PE:DCM = 5:1, volume ratio) to obtain the crude product. Methanol was then added and the mixture was stirred to obtain 22.4g of white solid, with a yield of 86.9%.

[0167] Mass spectrometry analysis determined the molecular ion mass [M] of intermediate M7-2. + H] + : 447.31 (Theoretical value: 446.27).

[0168] (3) Synthesis of intermediate M7-3:

[0169] At room temperature, intermediate M7-2 (20.0 g), 1,3-dibromo-2-fluoro-4-iodobenzene (17.0 g), and cesium carbonate (14.6 g) were dissolved in 300 mL of DMF. After purging with nitrogen three times, the reaction system was heated to 100 °C and reacted for 15 h. After the reaction was cooled to room temperature, water was added to precipitate the solid, which was then filtered. The filter cake was dissolved, and the organic phase was concentrated with silica gel. Column chromatography (PE:DCM = 5:1, volume ratio) was performed to obtain the crude product, which was then slurried with methanol to obtain 31.7 g of white solid, with a yield of 87.8%.

[0170] Mass spectrometry analysis determined the molecular ion mass of intermediate M7-3 [M + H]+ : 807.01 (Theoretical value: 806.02).

[0171] (4) Synthesis of intermediate M7-4:

[0172] At room temperature, intermediate M7-3 (20.0 g), p-tert-butylphenol (3.7 g), cuprous iodide (2.4 g), 1,10-phenanthroline (4.5 g), potassium phosphate (10.5 g), and DMF (500 mL) were added to a 1 L single-necked flask. The mixture was purged with nitrogen three times and heated to 100 °C overnight. The reaction solution was cooled to room temperature, water was added to precipitate the solid, and the mixture was filtered. After the filter cake dissolved, the organic phase was concentrated and precipitated by silica gel column chromatography (PE:DCM = 4:1, volume ratio) to obtain the crude product. Methanol was then added and the mixture was stirred to obtain 18.6 g of white solid, with a yield of 90.5%.

[0173] Mass spectrometry analysis determined the molecular ion mass [M] of intermediate M7-4. + H] + : 829.24 (Theoretical value: 828.21).

[0174] (5) Synthesis of compound M7:

[0175] At room temperature, intermediate M7-4 (15.0 g) was dissolved in 120 mL of xylene. After purging with nitrogen three times, the reaction system was cooled to -70 °C, and then 18.1 mL of n-butyllithium (2.5 M) was added. The mixture was stirred for 30 minutes while maintaining the low temperature. Subsequently, 10.5 mL of boron tribromide was added under nitrogen protection, and the mixture was heated to 80 °C and stirred for 60 minutes. Finally, 25.3 mL of diisopropylethylamine was added at low temperature, and the reaction system was heated to 120 °C and reacted for 8 hours. After the reaction was cooled to room temperature, methanol was added to precipitate the solid. The solid was filtered, and the filter cake was dissolved and concentrated by silica gel column chromatography (PE:DCM = 4:1, volume ratio) to obtain the crude product. The crude product was then recrystallized to give 2.1 g of yellow solid, with a yield of 16.9%.

[0176] Mass spectrometry analysis determined the molecular ion mass of compound M7 [M + H] + 687.35 (Theoretical value: 686.36).

[0177] Synthesis Example 2

[0178] This synthetic example provides compound M85 and its synthetic method, which is as follows:

[0179]

[0180] (1) Synthesis of intermediate M85-1

[0181] Following the synthesis method of intermediate M7-1 in Synthesis Example 1, the only difference is that compound A1 is replaced by compound A2 to obtain intermediate M85-1;

[0182] Mass spectrometry analysis determined the molecular ion mass of intermediate M85-1 [M + H] + 585.31 (Theoretical value: 584.25).

[0183] (2) Synthesis of intermediate M85-2

[0184] The synthesis method of intermediate M7-2 in Synthesis Example 1 is the same as that used in Synthesis Example 1, except that intermediate M7-1 is replaced by intermediate M85-1 to obtain intermediate M85-2;

[0185] Mass spectrometry analysis determined the molecular ion mass [M] of intermediate M85-2. + H] + : 485.22 (Theoretical value: 484.19).

[0186] (3) Synthesis of intermediate M85-3

[0187] The synthesis method of intermediate M7-3 in Synthesis Example 1 is the same as that in Synthesis Example 1, except that intermediate M7-2 is replaced by intermediate M85-2 to obtain intermediate M85-3;

[0188] Mass spectrometry analysis determined the molecular ion mass [M] of intermediate M85-3. + H] + : 844.97 (Theoretical value: 843.94).

[0189] (4) Synthesis of intermediate M85-4

[0190] The synthesis method of intermediate M7-4 in Synthesis Example 1 is the same as that used in Synthesis Example 1, except that intermediate M7-4 is replaced by intermediate M85-3 and p-tert-butylphenol is replaced by 3,6-diphenylcarbazole to obtain intermediate M85-4.

[0191] Mass spectrometry analysis determined the molecular ion mass of intermediate M85-4 [M + H] + : 1036.19 (Theoretical value: 1035.16).

[0192] (5) Synthesis of compound M85:

[0193] The synthesis method of compound M7 in Synthesis Example 1 was followed, except that intermediate M7-4 was replaced with intermediate M85-4 to obtain compound M85;

[0194] Mass spectrometry analysis determined the molecular ion mass of compound M85 [M+ H] + : 894.35 (Theoretical value: 893.32).

[0195] Synthesis Example 3

[0196] This synthetic example provides compound M226 and its synthetic method, which is as follows:

[0197]

[0198] (1) Synthesis of intermediate M226-1

[0199] The intermediate M7-1 was synthesized using the same method as in Example 1, except that compound A1 was replaced with compound A3, to obtain intermediate M226-1.

[0200] Mass spectrometry analysis determined the molecular ion mass of intermediate M85-1 [M + H] + 587.42 (Theoretical value: 586.36).

[0201] (2) Synthesis of intermediate M226-2

[0202] The synthesis method of intermediate M7-2 in Synthesis Example 1 is the same as that of intermediate M7-1, except that intermediate M226-1 is used to replace intermediate M7-1 to obtain intermediate M226-2;

[0203] Mass spectrometry analysis determined the molecular ion mass [M] of intermediate M226-2. + H] + : 487.36 (Theoretical value: 486.30).

[0204] (3) Synthesis of intermediate M226-3

[0205] The synthesis method of intermediate M7-3 in Synthesis Example 1 is the same as that used in Synthesis Example 1, except that intermediate M7-2 is replaced by intermediate M226-2 to obtain intermediate M226-3;

[0206] Mass spectrometry analysis determined the molecular ion mass [M] of intermediate M226-3. + H] + : 805.06 (Theoretical value: 804.00).

[0207] (4) Synthesis of intermediate M226-4

[0208] The synthesis method of intermediate M7-4 in Synthesis Example 1 is the same as that used in Synthesis Example 1, except that intermediate M7-4 is replaced by intermediate M226-3 to obtain intermediate M226-4;

[0209] Mass spectrometry analysis determined the molecular ion mass [M] of intermediate M226-4. + H] + 1009.17 (Theoretical value: 1008.22).

[0210] (5) Synthesis of compound M226:

[0211] The synthesis method of compound M7 in Synthesis Example 1 was followed, except that intermediate M7-4 was replaced with intermediate M226-4 to obtain compound M226;

[0212] Mass spectrometry analysis determined the molecular ion mass of compound M226 [M + H] + : 909.46 (Theoretical value: 908.42).

[0213] This invention provides exemplary methods for synthesizing representative intermediate core compounds, as well as examples of synthesizing compounds of this invention by reacting a portion of the core with raw materials. For other compounds for which no specific synthesis method is given, they can also be prepared by similar methods, requiring only the replacement of raw materials. These methods will not be elaborated here, or those skilled in the art can prepare them using other methods in the prior art.

[0214] Device Example 1

[0215] This embodiment provides an organic electroluminescent device, comprising, sequentially arranged, an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al). The fabrication method of this organic electroluminescent device is as follows:

[0216] (1) The glass substrate coated with ITO transparent conductive layer was ultrasonically treated in commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone / ethanol mixed solvent, baked in a clean environment until the moisture was completely removed, cleaned with ultraviolet light and ozone, and bombarded with low-energy cation beam.

[0217] (2) Place the glass substrate with the anode in the vacuum chamber and evacuate it to a vacuum level of less than 1×10⁻⁶. -5 Pa, a mixture of compound HT-4:HI-3 (97 / 3, w / w) was vacuum-deposited on the above anodic layer as a hole injection layer at a deposition rate of 0.1 nm / s and a film thickness of 10 nm.

[0218] (3) The compound HT-4 was vacuum-deposited on the hole injection layer as a hole transport layer at a deposition rate of 0.1 nm / s and a total film thickness of 105 nm.

[0219] (4) The compound PH-86 was vacuum-deposited on the hole transport layer as an electron blocking layer at a deposition rate of 0.1 nm / s and a total film thickness of 5 nm.

[0220] (5) A light-emitting layer is vacuum-deposited on the electron blocking layer. The light-emitting layer comprises a quaternary mixture of host material PH-86:PH-89 (60:40, w / w), sensitizer BPD-1 (doped 13%) and dye (polycyclic aromatic compound M7 provided by the present invention, doped 1%). The total evaporation rate is 0.1 nm / s and the total evaporation film thickness is 35 nm.

[0221] (6) The compound PH-89 was vacuum-deposited on the light-emitting layer as a hole blocking layer at a deposition rate of 0.1 nm / s and a total film thickness of 5 nm.

[0222] (7) A mixture of compound ET-69:ET-57 (50 / 50, w / w) was vacuum-deposited on the hole blocking layer as an electron transport layer at a deposition rate of 0.1 nm / s and a total film thickness of 25 nm.

[0223] (8) LiF was vacuum-deposited on the electron transport layer as an electron injection layer at a deposition rate of 0.1 nm / s and a thickness of 1 nm.

[0224] (9) An Al layer with a thickness of 150 nm is vacuum-deposited on the electron injection layer as the cathode of the device at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0225] Device Examples 2-5, Device Comparative Example 1

[0226] Device Examples 2-5 and Device Comparative Example 1 each provide an organic electroluminescent device. The only difference between them and Device Example 1 is that the dyes of the light-emitting layer are the compounds shown in Table 1. Other layers, thicknesses, materials, and preparation methods are the same as those in Device Example 1.

[0227] Comparative Example 1 uses compound D2 as a dye. The structural formula of compound D2 is shown below:

[0228]

[0229] Device performance testing:

[0230] (1) λmax and FWHM: directly measured by organic electroluminescent devices;

[0231] (1) LT95 lifespan: tested with a luminance meter at 40mA / cm 2The initial brightness value of the device under the current density is measured. The current density is kept constant, and the time it takes for the device brightness to drop to 95% of the initial brightness is measured in hours. The LT95 lifetime test value of device Comparative Example 1 is recorded as 1.0. The ratio of the LT95 lifetime test value of other devices to the LT95 lifetime test value of device Comparative Example 1 is calculated.

[0232] (2) External quantum efficiency: The device efficiency was measured using the integrating sphere method at 10 mA / cm². 2 The external quantum efficiency (EQE, %) at current density is calculated by setting the external quantum efficiency test value of device comparison example 1 as 1.0, and calculating the ratio of the external quantum efficiency test values ​​of other devices to the external quantum efficiency test value of device comparison example 1.

[0233] The test results are shown in Table 1:

[0234] Table 1

[0235] dye <![CDATA[λ max (nm)]]> FWHM(nm) EQE LT95 Device Example 1 Compound M7 447 20 1.2 1.4 Device Example 2 Compound M11 457 21 1.4 1.7 Device Example 3 Compound M46 463 21 1.4 1.5 Device Example 4 Compound M104 467 20 1.3 1.6 Device Example 5 Compound M259 459 22 1.4 1.4 Device Example 6 Compound M262 468 21 1.5 1.4 Device Example 7 Compound M263 465 21 1.4 1.5 Device Comparison Example 1 Compound D2 484 23 1 1

[0236] Device Example 8

[0237] This embodiment of the device provides an organic electroluminescent device, comprising an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) arranged sequentially; the fabrication method of this organic electroluminescent device is as follows:

[0238] (1) The glass substrate coated with ITO transparent conductive layer was ultrasonically treated in commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone / ethanol mixed solvent, baked in a clean environment until the moisture was completely removed, cleaned with ultraviolet light and ozone, and bombarded with low-energy cation beam.

[0239] (2) Place the glass substrate with the anode in the vacuum chamber and evacuate it to a vacuum level of less than 1×10⁻⁶. -5 Pa, a mixture of compound HT-4:HI-3 (97 / 3, w / w) was vacuum-deposited on the above anodic layer as a hole injection layer at a deposition rate of 0.1 nm / s and a film thickness of 10 nm.

[0240] (3) The compound HT-4 was vacuum-deposited on the hole injection layer as a hole transport layer at a deposition rate of 0.1 nm / s and a total film thickness of 105 nm.

[0241] (4) The compound HT-40 was vacuum-deposited on the hole transport layer as an electron blocking layer at a deposition rate of 0.1 nm / s and a total film thickness of 5 nm.

[0242] (5) A light-emitting layer is vacuum-deposited on the electron blocking layer. The light-emitting layer comprises a quaternary mixture of host material PH-89:PH-3 (50:50, w / w), GPD-12 (doped 10%) and dye (the polycyclic aromatic compound M27 provided by this invention, doped 1%). The total evaporation rate is 0.1 nm / s and the total evaporation film thickness is 40 nm.

[0243] (6) The compound ET23 was vacuum-deposited on the light-emitting layer as a hole blocking layer at a deposition rate of 0.1 nm / s and a total film thickness of 5 nm.

[0244] (7) A mixture of compound ET-69:ET-57 (50 / 50, w / w) was vacuum-deposited on the hole blocking layer as an electron transport layer at a deposition rate of 0.1 nm / s and a total film thickness of 25 nm.

[0245] (8) LiF was vacuum-deposited on the electron transport layer as an electron injection layer at a deposition rate of 0.1 nm / s and a thickness of 1 nm.

[0246] (9) An Al layer with a thickness of 150 nm is vacuum-deposited on the electron injection layer as the cathode of the device at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0247] Device Examples 9-20, Device Comparative Examples 2-3

[0248] Device Examples 9-20 and Device Comparative Examples 2-3 each provide an organic electroluminescent device. The only difference between them and Device Example 8 is that the dyes of the light-emitting layer are the compounds shown in Table 2. The other layers, thicknesses, materials and preparation methods are the same as those of Device Example 8.

[0249] The dyes used in Comparative Examples 2-3 of the devices were compounds D1 and D2 as described above.

[0250] Device performance testing

[0251] (1) λmax and FWHM: directly measured by organic electroluminescent devices;

[0252] (1) LT95 lifespan: tested with a luminance meter at 40mA / cm 2 The initial brightness value of the device under the current density is measured. The current density is kept constant, and the time it takes for the device brightness to drop to 95% of the initial brightness is measured in hours. The LT95 lifetime test value of device Comparative Example 1 is recorded as 1.0. The ratio of the LT95 lifetime test value of other devices to the LT95 lifetime test value of device Comparative Example 1 is calculated.

[0253] (2) External quantum efficiency: The device efficiency was measured using the integrating sphere method at 10 mA / cm². 2The external quantum efficiency (EQE, %) at current density is calculated by setting the external quantum efficiency test value of device comparison example 1 as 1.0, and calculating the ratio of the external quantum efficiency test values ​​of other devices to the external quantum efficiency test value of device comparison example 1.

[0254] The test results are shown in Table 2:

[0255] Table 2

[0256] dye <![CDATA[λ max (nm)]]> FWHM(nm) EQE LT95 Device Example 9 Compound M27 509 22 1.4 1.2 Device Example 10 Compound M53 525 21 1.2 1.5 Device Example 11 Compound 76 521 20 1.4 1.6 Device Example 2 Compound M83 516 19 1.3 1.5 Device Example 13 Compound M85 522 20 1.5 1.6 Device Example 14 Compound M98 526 23 1.3 1.4 Device Example 15 Compound 101 528 19 1.6 1.6 Device Example 16 Compound M111 521 22 1.5 1.3 Device Example 17 Compound M127 526 20 1.5 1.2 Device Example 18 Compound M165 528 23 1.4 1.6 Device Example 19 Compound M226 526 23 1.5 1.5 Device Example 20 Compound M241 526 20 1.5 1.6 Device Comparison Example 2 Compound D1 520 26 1 1 Device Comparison Example 3 Compound D2 486 26 0.6 0.5

[0257] As can be seen from the above devices, the compound of the present invention has a narrower half-peak width than the comparative compound 1. The modification of the peripheral groups can achieve the adjustment from blue light to green light. At the same time, in phosphorus-sensitized fluorescent devices, the compound of the present invention has significant advantages over the comparative compound in terms of both efficiency and lifetime.

[0258] In summary, this invention, through the special design of its molecular structure, enables the polycyclic aromatic compounds to effectively suppress vibrations in the excited state, narrow the half-peak width, and exhibit superior color purity compared to the comparative compounds. Furthermore, as a dye in the luminescent layer of a device, it extends device lifespan, improves luminous efficiency, and significantly optimizes the device's luminescent performance.

[0259] This invention designs specific structures for aromatic compounds, employing a double-boron structure on the core of the aromatic compound with tunable peripheral groups to achieve a wide range of spectral emission. This structure lowers the HOMO level of the material, reducing hole trapping and creating a more balanced transport of holes and electrons in the device, thus improving device performance. Furthermore, the double-boron structure narrows the full width at half maximum (FWHM), increasing PLQY and contributing to improved device efficiency. Through ingenious molecular design, this invention provides aromatic compounds highly suitable for OLED applications and enhancing device performance.

[0260] The applicant declares that the detailed process flow of this invention is illustrated by the above embodiments, but this invention is not limited to the above detailed process flow, that is, it does not mean that this invention must rely on the above detailed process flow to be implemented. Those skilled in the art should understand that any improvements to this invention, equivalent substitutions of raw materials for the product of this invention, addition of auxiliary components, and selection of specific methods, etc., all fall within the protection scope and disclosure scope of this invention.

Claims

1. An aromatic compound, characterized in that, The aromatic compounds include those having the structure shown in Formula I: Among them, ring A and ring B are each independently selected from one of substituted or unsubstituted C6-C60 aromatic rings and substituted or unsubstituted C2-C60 heteroaromatic rings; The substituents in ring A and ring B are each independently selected from halogens, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, unsubstituted or R'-substituted C6-C30 heteroarylsilyl groups, unsubstituted or R'-substituted C1-C20 alkylamino groups, cyano groups, nitrate groups, etc. The substituted group comprises any one of the following: aryl, amino, hydroxyl, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; wherein the substituted substituents are not connected to each other or are linked to form a ring by chemical bonds; wherein each substituted substituent is independently not connected to or linked to an adjacent ring structure by chemical bonds. Y1 and Y2 are each independently selected from any one of CR1R2, SiR3R4, NR5, Se, O, or S. M is selected from single bonds, CR6R7, SiR8R9, O, S, Se, NR 10 Any one of them; X1 to X7 are each independently selected from N or CR 11 Furthermore, X6 is not connected to ring B to form a ring; R'、R1-R 11 Selected from hydrogen atoms, halogens, substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 heteroarylsilyl groups, substituted or unsubstituted C1-C20 alkylamino groups, cyano groups, and nitro groups. Any one of the following: amino, hydroxyl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; and at least two any two adjacent R1 and R2, R3 and R4, R6 and R7, R8 and R9. 11 They are either not connected or linked by chemical bonds to form a ring, R1-R 11 Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds; R'、R1-R 11 The substituents described herein are each independently selected from any one or a combination of at least two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; the substituents are not connected to each other or are linked to form a ring by chemical bonds; the substituents are each independently not connected to adjacent ring structures or are linked to form a ring by chemical bonds. Adjacent R's are either not connected to each other or are linked to each other by chemical bonds to form a ring; each R' is independently not connected to its adjacent ring structure or is linked to each other by chemical bonds to form a ring.

2. The aromatic compound according to claim 1, characterized in that, Ring A and ring B each independently have the structure shown in equation a or equation b: Among them, Q1-Q8 are each independently selected from CR 12 Or N; In Q1-Q8, R 12 Each is independently selected from hydrogen atoms, halogens, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, unsubstituted or R'-substituted C6-C30 heteroarylsilyl groups, and unsubstituted... Or R'-substituted C1-C20 alkylamino, cyano, nitro, amino, hydroxyl, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; any one of the following: two adjacent R 12 The R are either not connected or linked by chemical bonds to form a ring; 12 Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds; X a Selected from CR 16 R 17 SiR 18 R 19 , O, S, Se, NR 20 Any one of the O or S; R 16 -R 20 Selected from any one of hydrogen atoms, halogens, substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 heteroarylsilyl groups, substituted or unsubstituted C1-C20 alkylamino groups, cyano groups, nitro groups, amino groups, hydroxyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C3-C30 heteroarylamino groups, substituted or unsubstituted C6-C30 aryloxy groups, substituted or unsubstituted C3-C30 heteroaryloxy groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups; The R 16 With R 17 Between, R 18 With R 19 They are either not connected to each other or linked together by chemical bonds to form a ring; Preferably, ring A and ring B each have the structure shown in the following formula: Among them, R a1 -R a7 Each is independently selected from halogens, unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl groups, unsubstituted or R'-substituted C3-C20 cycloalkyl groups, unsubstituted or R'-substituted C2-C20 alkenyl groups, unsubstituted or R'-substituted C1-C20 alkoxy groups, unsubstituted or R'-substituted C1-C20 alkylsilyl groups, unsubstituted or R'-substituted C6-C30 arylsilyl groups, unsubstituted or R'-substituted C6-C30 heteroarylsilyl groups, and unsubstituted or Any one of the following: R'-substituted C1-C20 alkylamino, cyano, nitro, amino, hydroxyl, unsubstituted or R'-substituted C6-C30 arylamino, unsubstituted or R'-substituted C3-C30 heteroarylamino, unsubstituted or R'-substituted C6-C30 aryloxy, unsubstituted or R'-substituted C3-C30 heteroaryloxy, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; wherein R a1 -R a7 The R are either not connected or linked by chemical bonds to form a ring; a1 -R a7 Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds; n1 and n7 represent integers from 0 to 4, and n2-n6 represent integers from 0 to 6.

3. The aromatic compound according to claim 1 or 2, characterized in that, Y1 and Y2 are each independently selected from any one of CR1R2, SiR3R4, NR5, O or S, preferably any one of CR1R2, NR5, S or O, and more preferably any one of NR5, S or O; Preferably, at least one of Y1 and Y2 is selected from NR5; Preferably, Y1 and Y2 are each independently selected from NR5; Preferably, either Y1 or Y2 is selected from NR5, and the other is selected from O; Preferably, each of R1-R5 is independently selected from any one of substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C2-C10 alkenyl groups, substituted or unsubstituted C1-C20 alkoxy groups, cyano groups, substituted or unsubstituted C6-C20 aryl groups, and substituted or unsubstituted C3-C20 heteroaryl groups; R1 and R2, and R3 and R4 are not connected or are linked to each other by chemical bonds to form a ring, and each of R1-R5 is independently not connected to the adjacent ring structure or is linked to the adjacent ring structure by chemical bonds to form a ring; Each of the substituents in R1-R5 is independently selected from any one or a combination of at least two of the following: C1-C6 straight-chain or branched alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C6-C12 aryl, C3-C12 heteroaryl, and C6-C10 arylamino; the substituents are not connected to each other or are linked to form a ring by chemical bonds; each substituent is independently not connected to an adjacent ring structure or is linked to form a ring by chemical bonds. Preferably, each of R1-R4 is independently selected from any one of C1-C5 straight-chain or branched alkyl, C2-C5 alkenyl, C6-C12 aryl, and C3-C12 heteroaryl; R1 and R2, and R3 and R4 are not connected or are connected to each other by chemical bonds to form a ring, and each of R1-R5 is independently not connected to the adjacent ring structure or is connected to each other by chemical bonds to form a ring; Preferably, R5 is selected from groups having the following structure: Among them, R Y1 -R Y9 Each is independently selected from any one or a combination of at least two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. m1 represents integers from 0 to 5, m2 represents integers from 0 to 4, and m3 represents integers from 0 to 7; Preferably, R Y1 -R Y9 Each is independently selected from any one or a combination of at least two of the following: C1-C6 straight-chain or branched alkyl, -SiH(CH3)2, C6-C12 aryl, C3-C12 heteroaryl, and C6-C10 arylamino; adjacent R Y1 Between, adjacent R Y3 Between, adjacent R Y4 Between, R Y5 -R Y7 Between, R Y8 -R Y9 They are either not connected or linked by chemical bonds to form a ring; R Y1 -R Y9 Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds.

4. The aromatic compound according to any one of claims 1-3, characterized in that, The M represents a single bond, CR6R7, SiR8R9, O, S, Se, NR. 10 Any one of them: The R6-R 10 Each is independently selected from any one of the following: substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C2-C10 alkenyl groups, substituted or unsubstituted C1-C20 alkoxy groups, cyano groups, substituted or unsubstituted C6-C20 aryl groups, and substituted or unsubstituted C3-C20 heteroaryl groups; R6 and R7, and R8 and R9, are not connected or are linked by chemical bonds to form a ring, R6-R 10 Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds; The R6-R 10 The substituents described herein are each independently selected from any one or a combination of at least two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; the substituents are not connected to each other or are linked to form a ring by chemical bonds; the substituents are each independently not connected to adjacent ring structures or are linked to form a ring by chemical bonds. Preferably, the R6-R 10 The substituents described herein are each independently selected from any one or a combination of at least two of the following: C1-C6 straight-chain or branched alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C6-C12 aryl, C3-C12 heteroaryl, and C6-C10 arylamino; the substituents are not connected to each other or are linked to form a ring by chemical bonds; the substituents are each independently not connected to adjacent ring structures or are linked to form a ring by chemical bonds. Preferably, M represents any one of a single bond, CR6R7, O, S, and Se; more preferably, a single bond or CR6R7; and even more preferably, a single bond. R6-R7 are selected from any one or a combination of at least two of C1-C10 straight-chain or branched alkyl, C6-C12 aryl, C3-C12 heteroaryl, and C6-C10 arylamino; the substituted substituents are not connected to each other or are linked to form a ring by chemical bonds; each substituted substituent is independently not connected to the adjacent ring structure or is linked to form a ring by chemical bonds.

5. The aromatic compound according to any one of claims 1-4, characterized in that, X1 to X7 are CR 11 ; Preferably, the R 11 Selected from any one of hydrogen atoms, halogens, substituted or unsubstituted C1-C20 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C2-C20 alkenyl groups, substituted or unsubstituted C1-C20 alkoxy groups, substituted or unsubstituted C1-C20 alkylsilyl groups, substituted or unsubstituted C6-C30 arylsilyl groups, substituted or unsubstituted C6-C30 heteroarylsilyl groups, substituted or unsubstituted C1-C20 alkylamino groups, cyano groups, nitro groups, amino groups, hydroxyl groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C3-C30 heteroarylamino groups, substituted or unsubstituted C6-C30 aryloxy groups, substituted or unsubstituted C3-C30 heteroaryloxy groups, substituted or unsubstituted C6-C60 aryl groups, and substituted or unsubstituted C3-C60 heteroaryl groups; at least two any two adjacent R groups. 11 They are either not connected or linked by chemical bonds to form a ring, R 11 Each ring is independent and not connected to the adjacent ring structure or is connected to form a ring by chemical bonds; Preferably, the R 11 It is selected from any one of hydrogen atom, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C6-C20 aryl, and C3-C20 heteroaryl, more preferably any one of hydrogen atom, C1-C5 straight-chain or branched alkyl, C6-C12 aryl, and C3-C10 heteroaryl, and even more preferably any one of methyl, ethyl, tert-butyl, phenyl, or naphthyl; Preferably, X1, X3, X4, X6, and X7 are CH, and X2 and X5 are each independently CR. 11 R 11 It is selected from any one of hydrogen atom, methyl, ethyl, tert-butyl, phenyl or naphthyl.

6. The aromatic compound according to any one of claims 1-5, characterized in that, The aromatic compounds include those having the structures shown in Formula I-1, Formula I-2, Formula I-3, Formula I-4 or Formula I-5: Among them, Q1-Q 16 Each independently selected from CR 12 ; R 12 It has the same definition as claim 2; Y1, Y2, and X1 to X7 each have the same definition as in claim 1.

7. The aromatic compound according to any one of claims 1-6, characterized in that, The aromatic compounds include the following compounds:

8. An application of an aromatic compound as described in any one of claims 1-7, characterized in that, The aromatic compounds are used to prepare organic electronic devices; Preferably, the organic electronic device includes any one or a combination of at least two of the following: organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper; Preferably, the aromatic compound is used as a light-emitting layer material in organic electronic devices, and more preferably as a light-emitting dye in the light-emitting layer.

9. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; the organic layer includes at least one aromatic compound as described in any one of claims 1-7; Preferably, the organic layer includes a light-emitting layer, wherein the light-emitting layer includes at least one aromatic compound as described in any one of claims 1-7; Preferably, the light-emitting layer comprises a host material and a light-emitting dye, wherein the light-emitting dye comprises at least one aromatic compound as described in any one of claims 1-7.

10. A display device, characterized in that, The display device includes the organic electroluminescent device as described in claim 9.

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