Aromatic compound and application thereof

Abstract

The invention provides an aromatic compound and application thereof. The aromatic compound has a structure as shown in a formula (1). The aromatic compound provided by the invention has good stability and steric configuration, has excellent carrier transport efficiency, and can effectively prolong the service life of an organic electroluminescent device and improve the luminous efficiency when being used as a material of a luminous layer for the organic electroluminescent device.

Description

Technical Field

[0001] This invention belongs to the field of organic light-emitting materials technology, and relates to an aromatic compound and its applications, specifically a polycyclic 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 possess high fluorescence quantum yields. In particular, compared to traditional blue fluorescent dyes, they exhibit narrower spectra and higher color purity, demonstrating 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 solve the problems related to efficiency, lifespan, and cost of OLED products.

[0007] Therefore, there is an urgent need in this field to develop more types and higher performance organic materials for use in organic electroluminescent devices, so that the devices can have better light emission effects and longer lifespans. Summary of the Invention

[0008] To address the shortcomings of existing technologies, the present invention aims to provide an aromatic compound and its applications, specifically a polycyclic aromatic compound and its applications. The polycyclic aromatic compound provided by the present invention incorporates a group (e.g., a benzo[a]benzyl] group) as shown in formula (2) on or around a parent nucleus (e.g., a BN parent nucleus). This group, on the one hand, helps suppress shoulder peaks, significantly narrowing the half-width at half-maximum (WHM) of the material and improving the color purity of the blue light material; on the other hand, the presence of this structure lowers the triplet energy level of the molecule, which is beneficial for improving the color purity, luminous efficiency, and lifetime of the device. Through ingenious molecular / device design, the aromatic compound provided by the present invention is highly suitable for application in OLEDs and enhances device performance.

[0009] To achieve this objective, the present invention adopts the following technical solution:

[0010] In a first aspect, the present invention provides an aromatic compound having the structure shown in formula (1):

[0011]

[0012] In formula (1), ring A, ring D, and ring E are each independently selected from any one of the following: substituted or unsubstituted C6-C50 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, etc.) aromatic rings, and substituted or unsubstituted C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaromatic rings;

[0013] X1 and X2 are each independently O, S or NAr1, and Ar1 is each independently selected from any one of the groups shown in formula (2), substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups;

[0014] Furthermore, at least one of ring A, ring D, ring E, and Ar1 is substituted with a group as shown in formula (2), and / or Ar1 is a group as shown in formula (2);

[0015] The group shown in formula (2) is connected to formula (1) through any chemically permissible site;

[0016] In equation (2), X3 represents O and NR. 11 Or S;

[0017] Y1-Y 10 Each is independently selected from N and CR 12 Or C, and at least one of them is C, said C being connected to equation (1); or, Y1-Y 10 Each is independently selected from N or CR 12 And there are two adjacent R 12 The rings are connected by chemical bonds and are connected to formula (1);

[0018] R 11 R 12 Each is independently selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 straight-chain or branched alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; two adjacent R 12 They are either not connected or linked by chemical bonds to form a ring;

[0019] Ring A, Ring D, Ring E, Ar1, R 11 , R 12 The substituents in 11 are each independently selected from any one or a combination of at least two of halogen, cyano, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, C3-C30 heteroaryl, and C6-C30 silylaryl.

[0020] The aromatic compound provided by the present invention has good stability and spatial configuration, and has excellent carrier transport efficiency. As a material for the light-emitting layer in an organic electroluminescent device, it can effectively extend the life of the device and improve the light-emitting efficiency.

[0021] In the present invention, the group of "substituted or unsubstituted" can be substituted with one substituent or multiple substituents. When there are multiple (at least 2) substituents, they can be the same or different substituents; when the same expression is involved hereinafter, it has the same meaning, and unless otherwise specified, the selection range of substituents is as shown above and will not be elaborated one by one.

[0022] It should be noted that in this application, 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 various groups, rather than the effect of a single group.

[0023] In the present invention, for the description 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 the heteroaryl are selected from atoms or atomic groups of N, O, S, P, B, Si or Se, preferably N, O, S, Si, Se.

[0025] In the present invention, the expression of the ring structure with a "-" or "------" drawn across it indicates that the connection site is at any position on the ring structure where bonding can occur.

[0026] In this invention, the expression Ca-Cb represents that the group has ab carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0027] In this invention, "each independently" means that when there are multiple subjects, they can be the same or different from each other.

[0028] In this invention, the C6-C30 aryl groups can all be aryl groups of C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc., including monocyclic aryl or fused-ring aryl groups. The monocyclic aryl group refers to a group containing at least one phenyl group. When it contains at least two phenyl groups, the phenyl groups are linked by single bonds. Examples include, but are not limited to, phenyl, biphenyl, and terphenyl groups. The fused-ring aryl group refers to a group containing at least two aromatic rings, where the aromatic rings share two adjacent carbon atoms fused together. Examples include, but are not limited to, naphthyl, naphthylphenyl, phenylnaphthyl, anthraceneyl, phenanthryl, indene, fluorenyl and its derivatives (9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirodifluorenyl, benzo[a]fluorenyl, etc.), fluoranyl, triphenylene, pyrene, perylene, etc. Groups such as alkyl or tetraphenyl; the aforementioned groups include all possible linkages.

[0029] In this invention, the C3-C30 heteroaryl groups can be heteroaryl groups of C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc., 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] 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, C18, etc., preferably C1-C10 straight-chain or branched alkyl groups; exemplary examples include but are 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.

[0031] In this invention, the C2-C20 alkenyl groups can all be alkenyl groups of C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.

[0032] 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, C18, etc.; exemplary, including but not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0033] In this invention, specific examples of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, 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 C6-C30 arylamino groups can all be arylamino groups of C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc., that is, groups formed by replacing at least one H on -NH2 with the aryl group listed above, including but not limited to: phenylamino, biphenylamino, naphthylamino, etc.

[0035] In this invention, the C3-C30 heteroarylamino groups can all be heteroarylamino groups of C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.

[0036] In this invention, the C1-C20 silane groups can all be silane groups such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, and C18.

[0037] In this invention, the C6-C30 aryloxy groups can all be aryloxy groups of C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.

[0038] In this invention, the C3-C30 heteroaryloxy groups can all be heteroaryloxy groups of C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.

[0039] In this invention, the C6-C30 silyl groups can all be silyl groups of C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.

[0040] In this invention, the halogen includes fluorine, chlorine, bromine, or iodine; the same descriptions used below have the same meaning.

[0041] Preferably, ring A and ring D each independently have the structure shown in equation (a) or equation (b):

[0042]

[0043] In this context, the dashed lines represent the connection sites of functional groups;

[0044] X4 is selected from O or S;

[0045] U1-U8 are each independently selected from CR2 or N;

[0046] R2 is independently selected from groups shown in formula (2), hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl, substituted or unsubstituted (e.g., C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) C2-C20 alkenyl, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C18, etc.) straight-chain or branched alkyl, substituted or unsubstituted (e.g., C3, C4, C5, C6, C18, etc.) C2-C20 alkenyl, substituted or unsubstituted C3-C20 (e.g. ...3-C20 alkenyl, C3-C20 alkenyl, C4, C5, C6, C18, C19, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) C2-C20 alkenyl, C3-C20 alkenyl, C3-C20 alkenyl, C3-C20 alkenyl, C3-C20 alkenyl, C3-C20 alkenyl, C3-C20 alkenyl, C3-C20 alkenyl, C3-C 7. Cycloalkyl groups (C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.), substituted or unsubstituted C1-C20 groups (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.), substituted or unsubstituted C6-C30 groups (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.), substituted or unsubstituted C3-C30 groups (e.g., C... 4. Heteroaryl amino groups (C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.), substituted or unsubstituted C6-C30 groups (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.), substituted or unsubstituted C3-C30 groups (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.), substituted or unsubstituted C3-C30 groups (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.). 8. Any one of the following: heteroaryl groups (C20, C22, C24, C26, C28, etc.); substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.); substituted or unsubstituted C3-C30 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.); two adjacent R2 groups are not connected or are linked by chemical bonds to form a ring.

[0047] For example, R2 is independently selected from one or a combination of two of the following groups: group (2), hydrogen, halogen, cyano, methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, 2,2-dimethylbutyl, butadiene, 2,2,5,5-tetramethylhexyl, phenyl, naphthyl, biphenyl, tert-butylphenyl, phenyl tert-butyl, carbazole, dibenzofuranyl, dibenzothiophene, diphenylamino, dipyridylamino, methoxy, and oxynaphthyl.

[0048] Preferably, each of the R2 groups is independently selected from the groups shown in formula (2), hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) cycloalkyl groups, substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, etc.) cycloalkyl groups, and substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, etc.). The substituted group is any one of the following: aryl (C18, C20, C22, C24, C26, C28, etc.), heteroaryl (C3-C30, e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.), and arylamino (C6-C30, e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.), wherein the substituted group is any one of halogen and any one of C1-C5 (e.g., C1, C2, C3, C4, C5) straight-chain or branched alkyl.

[0049] Preferably, the ring E has the structure shown in formula (c):

[0050]

[0051] In this context, the dashed lines represent the connection sites of functional groups;

[0052] Z1, Z2, and Z3 are each independently selected from CR3 or N;

[0053] R3 is independently selected from groups shown in formula (2), hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) cycloalkyl, substituted or unsubstituted C1-C20 (e.g., C2, C3 ...2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) cycloalkyl, substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) 3. Alkoxy groups (C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.), substituted or unsubstituted C6-C30 groups (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.), arylamino groups (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C...), substituted or unsubstituted C3-C30 groups (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C...). 24, C26, C28, etc.) heteroarylamino groups; substituted or unsubstituted C6-C30 groups (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryloxy groups; substituted or unsubstituted C3-C30 groups (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.) heteroaryloxy groups; substituted or unsubstituted C6-C30 groups (e.g., C8, C9, C10, C26, C28, etc.) heteroaryloxy groups; substituted or unsubstituted C6-C30 groups (e.g., C8, C9, C10, C26, C28, etc.) heteroaryloxy groups. Aryl groups of C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.; substituted or unsubstituted C3-C30 heteroaryl groups of C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.; and substituted or unsubstituted C6-C30 silyl groups of C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.

[0054] For example, R3 is independently selected from one or a combination of two of the following groups: group (2), hydrogen, halogen, cyano, methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, 2,2-dimethylbutyl, 2,2,5,5-tetramethylhexyl, phenyl, biphenyl, naphthyl, fluorophenyl, mesitylene, triphenylsilyl, tert-butylphenyl, phenyl tert-butyl, carbazole, diphenylamino, dipyridylamino, methoxy, and oxynaphthyl.

[0055] Preferably, each of the R3 groups is independently selected from the group shown in formula (2), hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) cycloalkyl groups, substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20 ... 2. Any one of the following: C24, C26, C28, etc.) aryl; C3-C30 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.) heteroaryl, wherein the substituent is halogen; any one of the following: C1-C5 (e.g., C1, C2, C3, C4, C5) straight-chain or branched alkyl; C6-C18 (e.g., C8, C9, C10, C12, C14, C16, etc.) aryl; C3-C18 (e.g., C4, C5, C6, C8, C9, C10, C12, C14, C16, etc.) heteroaryl.

[0056] Preferably, formula (1) has the following structure:

[0057]

[0058] Among them, X1 and X2 have the same limited range as described above;

[0059] X4 is selected from O or S;

[0060] x and y are each independent integers from 0 to 3 (e.g., 0, 1, 2, or 3); z is an integer from 0 to 2 (e.g., 0, 1, or 2);

[0061] R2 is independently selected from groups shown in formula (2), halogens, cyano groups, substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) cycloalkyl groups, substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, etc.) cycloalkyl groups, and substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, etc.) cycloalkyl groups. 18. Any one of the following: aryl (C20, C22, C24, C26, C28, etc.); heteroaryl (C3-C30, e.g., C4, C6, C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.); arylamino (C6-C30, e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.); wherein the substituent is halogen, or any one of the following: straight-chain or branched alkyl (C1-C5, e.g., C2, C3, C4, etc.); adjacent R2 groups are not connected or are linked by chemical bonds to form a ring.

[0062] R3 is independently selected from groups shown in formula (2), halogens, cyano groups, substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) cycloalkyl groups, substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, etc.) cycloalkyl groups, and substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, etc.). The substituted group is any one of the following: aryl (C18, C20, C22, C24, C26, C28, etc.) and heteroaryl (C3-C30, e.g., C4, C6, C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.), wherein the substituted group is any one of the following: halogen, straight-chain or branched alkyl (C1-C5, e.g., C2, C3, C4, etc.), aryl (C6-C18, e.g., C8, C9, C10, C12, C14, C16, etc.), and heteroaryl (C3-C18, e.g., C4, C5, C6, C8, C9, C10, C12, C14, C16, etc.).

[0063] Preferably, X1 and X2 are both NAr1, and each of the two Ar1 is independently selected from the group shown in formula (2) or any one of the groups shown below:

[0064]

[0065] In this context, the dashed lines represent the connection sites of functional groups;

[0066] R 21 -R 24Each group is independently selected from the group shown in formula (2), halogen, cyano, substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl, substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) alkoxy, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, etc.) alkoxy, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, etc.) alkoxy Cycloalkyl groups (C13, C14, C15, C16, C17, C18, etc.), substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) arylamino groups, substituted or unsubstituted C3-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroarylamino groups, substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryloxy groups, and substituted... Substituted or unsubstituted C3-C30 (e.g., C4, C6, C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl groups; substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl groups; substituted or unsubstituted C3-C30 (e.g., C4, C6, C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) heteroaryl groups; C6-C30 (e.g., C8, C9, C10, C12, C13 ... The substituted group is any one of the following: C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups; C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) silyl groups; C6-C20 (e.g., C8, C9, C10, C12, C14, C16, C18, etc.) aryl groups; and C3-C20 (e.g., C4, C6, C8, C9, C10, C12, C14, C16, C18, etc.) heteroaryl groups; the two adjacent R groups are also included. 21 Two adjacent R 22 They can be either not connected or linked together by chemical bonds to form a ring.

[0067] n1 is an integer from 0 to 5 (e.g., 0, 1, 2, 3, 4, or 5), n2 is an integer from 0 to 5 (e.g., 0, 1, 2, 3, 4, or 5), n3 is an integer from 0 to 4 (e.g., 0, 1, 2, 3, or 4), and n4 is an integer from 0 to 5 (e.g., 0, 1, 2, 3, 4, or 5).

[0068] Preferably, X1 and X2 are both NAr1, and each of the two Ar1 is independently selected from the group shown in formula (2) or any one of the groups shown below:

[0069]

[0070] R 21 Selected from the groups shown in formula (2).

[0071] Preferably, R 21 -R 24 Each group is independently selected from the groups shown in formula (2), substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl groups, or substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl groups. 5. A cycloalkyl group (C16, C17, C18, etc.) or a substituted or unsubstituted aryl group (C6-C30, e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.); the substituted group is any one of deuterium, halogen, or a straight-chain or branched alkyl group (C1-C10, e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.); two adjacent R groups... 21 Two adjacent R 22 Two adjacent R 24 They can be either not connected or linked together by chemical bonds to form a ring.

[0072] n1 is an integer from 0 to 5 (e.g., 0, 1, 2, 3, 4, or 5), n2 is an integer from 0 to 5 (e.g., 0, 1, 2, 3, 4, or 5), n3 is an integer from 0 to 4 (e.g., 0, 1, 2, 3, or 4), and n4 is an integer from 0 to 5 (e.g., 0, 1, 2, 3, 4, or 5).

[0073] Preferably, R 21 -R 24Each group is independently selected from the group shown in formula (2), C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) cycloalkyl groups, and C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl groups; wherein the substituted substituent is any one of deuterium, halogen, or C1-C5 (e.g., C2, C3, C4) straight-chain or branched alkyl groups.

[0074] Preferably, X1 and X2 are both NAr1, and each of the two Ar1 is independently selected from the group shown in formula (2) or any one of the groups shown below:

[0075] R 21 Selected from the groups shown in formula (2).

[0076] Preferably, at least one of Y1-Y4 is C, and the C is connected to equation (1).

[0077] Preferably, at least one of Y1-Y4 is C, which is connected to equation (1), and at most one of the remaining Ys is N, with the remaining Ys each independently selected from CR. 12 ;R 12Each is independently selected from hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl, C2-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) alkenyl, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C18, etc.) alkenyl, or substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C18, etc.) alkenyl. 6. Cycloalkyl (C17, C18, etc.), alkoxy (C1-C20, e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.), arylamino (C6-C30, e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.), arylamino (C3-C30, e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.). 8, etc.) heteroarylamino, C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) silyl, C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryloxy, C3-C30 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.) heteroaryloxy The substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl group, or the substituted or unsubstituted C3-C30 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.) heteroaryl group, wherein the substituted substituent is any one of deuterium, halogen, or C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl group.

[0078] Preferably, at least one of Y1-Y4 is C, which is connected to equation (1), and at most one of the remaining Ys is N, with the remaining Ys each independently selected from CR. 12 ;R 12 Each is independently selected from hydrogen, halogen, cyano, C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) straight-chain or branched alkyl, C2-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) alkenyl, C3-C20 (e.g., C4, C5, C6, C7, C8, C9, etc.) alkenyl, and C3-C20 (e.g., C4, C5, C6, C7, C8, C9, etc.) alkenyl, ... Cycloalkyl groups (C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.), alkoxy groups (C1-C20, e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.), alkoxy groups (C6-C30, e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.), arylamino groups (C3-C30, e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.), arylamino groups (C3-C30, e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.), arylamino groups (C6 ... 5. C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.) heteroarylamino, C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryloxy, C3-C30 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C 16, C17, C18, C20, C22, C24, C26, C28, etc.) heteroaryl group; C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl group; C3-C30 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.) heteroaryl group.

[0079] Preferably, the R 12Each is independently selected from hydrogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, etc.). Any one of the following: aryl (C26, C28, etc.), heteroaryl (C3-C30, such as C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.), and arylamino (C6-C30, such as C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.).

[0080] Preferably, the R 11 It is selected from any one of hydrogen, cyano, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, substituted or unsubstituted C3-C30 (e.g., C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26, C28, etc.) heteroaryl.

[0081] Preferably, the R 11 It is selected from any one of hydrogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, wherein the substituted group is a C1-C5 straight-chain or branched alkyl.

[0082] Preferably, equation (2) has the following structure:

[0083]

[0084] In this context, the dashed lines represent the connection sites of functional groups;

[0085] X3 represents O and NR. 11 Or S, R 11 It is selected from any one of hydrogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, wherein the substituted group is a C1-C5 straight-chain or branched alkyl.

[0086] Preferably, equation (2) has the following structure:

[0087]

[0088] In this context, the dashed lines represent the connection sites of functional groups;

[0089] X3 represents O and NR. 11 Or S, R 11 It is selected from any one of hydrogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, substituted or unsubstituted C6-C30 (e.g., C8, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc.) aryl, wherein the substituted group is a C1-C5 straight-chain or branched alkyl.

[0090] Preferably, the aromatic compound has any one of the following structures, but is not limited to the following structures:

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] In a second aspect, the present invention provides an application of an aromatic compound as described in the first aspect, wherein the aromatic compound is applied to an organic electronic device.

[0122] 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.

[0123] 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.

[0124] 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.

[0125] 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.

[0126] 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.

[0127] Preferably, the light-emitting layer further includes a sensitizer.

[0128] Preferably, the organic layer further includes a hole transport region and an electron transport region.

[0129] Preferably, the hole transport region includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, or an electron blocking layer.

[0130] Preferably, the electron transport region includes any one or a combination of at least two of the following: an electron injection layer, an electron transport layer, or a hole blocking layer.

[0131] 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.

[0132] 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.

[0133] 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.

[0134] 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 single-layer hole transport layers containing only one compound and single-layer hole transport layers 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.

[0135] 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 as shown in HT-1 to HT-51 below; or any combination thereof.

[0136]

[0137]

[0138]

[0139] 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 mentioned above, or one or more compounds of HI-1 to HI-3 mentioned 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 mentioned below.

[0140]

[0141] 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.

[0142] 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.

[0143] In one aspect of the invention, the light-emitting layer employs fluorescent electroluminescence technology. The fluorescent host material of the light-emitting layer may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.

[0144]

[0145] 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 M441 listed above.

[0146] In one aspect of the invention, the light-emitting layer employs phosphorescent photoluminescence technology. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-117.

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] 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.

[0153]

[0154] 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-51 to PH-77, PH-86 to PH-88, PH-92, PH-94 to PH-105 described above; or it may employ, but is not limited to, one or more compounds of HT-1 to HT-51 and one or more compounds of PH-51 to PH-77, PH-86 to PH-88, PH-92, PH-94 to PH-105.

[0155] 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).

[0156] 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.

[0157]

[0158]

[0159]

[0160]

[0161] 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-50, PH-78 to PH-85, PH-89 to PH-91, PH-93, PH-106 to PH-117; or it may employ, but is not limited to, one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-50, PH-78 to PH-85, PH-89 to PH-91, PH-93, PH-106 to PH-117.

[0162] The device may also include an electron injection layer located between the electron transport layer and the cathode, and the electron injection layer material includes, but is not limited to, one or more combinations of the following.

[0163] LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0164] Fourthly, the present invention provides a display device comprising the organic electroluminescent device as described in the third aspect.

[0165] Compared with the prior art, the present invention has at least the following beneficial effects:

[0166] (1) The aromatic compound provided by the present invention can improve the rigidity of the molecule and suppress the vibration of the molecular skeleton by introducing the group shown in formula (2) into the core or its periphery, which is beneficial to narrowing the half width at half maximum. The presence of the group shown in formula (2) can reduce the triplet energy level of the entire molecule to 2.2 eV. Using the aromatic compound in organic electroluminescent devices can reduce exciton quenching and material decomposition caused by excessive exciton energy in the device.

[0167] (2) The aromatic compounds provided by the present invention have good stability and spatial configuration, and excellent carrier transport efficiency. When used as materials for the light-emitting layer in organic electroluminescent devices, they can effectively extend the device life and improve the luminous efficiency. Detailed Implementation

[0168] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0169] The aromatic compounds provided by this invention can be obtained by known methods, such as synthesis using well-known organic synthesis methods. Exemplary synthetic routes are given below, but those skilled in the art can also obtain them using other known methods.

[0170] In one specific implementation, X1 and X2 are NAr1, and ring E is... For example, the aromatic compound can be prepared via the following synthetic route:

[0171]

[0172] Among them, rings A, D, Z1, Z2, Z3, and Ar1 have the same defined range as in equation (1); Hal 1 Hal 2 Hal 3 Each is an independent halogen, and Cl or Br is preferred.

[0173] It should be noted that obtaining the aromatic compounds is not limited to the synthetic methods and raw materials used in this invention. Those skilled in the art can also select other methods or routes to obtain the polycyclic aromatic compounds proposed in this invention. Compounds for which synthetic methods are not mentioned in this invention are all commercially available raw material products, or are prepared in-house using these raw material products according to known methods.

[0174] The solvents and reagents used in this invention can all be purchased from the chemical product market.

[0175] 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.

[0176] The structural analysis of intermediates and compounds in this invention was performed using an ABSCIEX mass spectrometer (4000QTRAP).

[0177] Synthesis Example 1: Synthesis of M8

[0178]

[0179] Synthesis of intermediate A1-1:

[0180] At room temperature, A1-0 (20.0 g), p-aminophenylboronic acid pinacol ester (17.4 g), Pd2(dba)3 (3.6 g), Sphos (3.3 g), sodium tert-butoxide (15.2 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 20.2 g of a white solid, yield 82.4%.

[0181] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + 310.15 (Theoretical value: 309.12).

[0182] Synthesis of intermediate A1:

[0183] At room temperature, Al-1 (20.0 g), p-tert-butylbromobenzene (13.7 g), Pd(dppf)Cl2 (2.4 g), sodium tert-butoxide (12.4 g), and toluene (400 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 22.3 g of a white solid, with a yield of 78.2%.

[0184] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 442.18 (Theoretical value: 441.21).

[0185] Synthesis of intermediate M8-1:

[0186] At room temperature, M8-0 (20.0 g), bis(p-tert-butyl)aniline (20 g), Pd2(dba)3 (3.2 g), tri-tert-butylphosphine (1.4 g), sodium tert-butoxide (13.6 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 mixture was cooled to room temperature, concentrated, extracted with dichloromethane, washed thoroughly with water, dried, and concentrated for column chromatography (PE:DCM = 10:1) to obtain 27.8 g of product, with a yield of 81.3%.

[0187] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 482.24 (Theoretical value: 481.23).

[0188] Synthesis of intermediate M8-2:

[0189] At room temperature, M8-1 (20.0 g), Al (18.3 g), Pd2(dba)3 (1.9 g), tri-tert-butylphosphine (0.8 g), sodium tert-butoxide (8.0 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 30.5 g of a white solid, with a yield of 82.9%.

[0190] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 887.40 (Theoretical value: 886.46).

[0191] Synthesis of compound M8:

[0192] At room temperature, M8-2 (20.0 g) was dissolved in 120 mL of xylene. After purging with nitrogen three times, the reaction system was cooled to -20 °C, and then tert-butyllithium (21 mL, 1.6 M) was added. The mixture was stirred at this low temperature for 30 minutes. The temperature was then gradually increased to 60 °C and maintained for 2 hours. Finally, the temperature of the reaction system was lowered back to -20 °C, and boron tribromide (5 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (17 mL) was added. The reaction system was then heated to 120 °C and reacted for 8 hours. After cooling to room temperature, the organic phase was evaporated to dryness under reduced pressure. The organic phase was extracted three times with dichloromethane (200 mL), and the two phases were combined, dried over anhydrous sodium sulfate, concentrated with silica gel, and subjected to column chromatography (PE:DCM = 20:1) to obtain a crude product. Recrystallization yielded 2.8 g of a yellow solid, with a yield of 12.4%.

[0193] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 861.54 (Theoretical value: 860.49).

[0194] Synthesis Example 2: Synthesis of M113

[0195]

[0196] Synthesis of intermediate A2-1:

[0197] At room temperature, A2-0 (20.0 g), p-aminophenylboronic acid pinacol ester (17.4 g), Pd2(dba)3 (3.6 g), Sphos (3.3 g), sodium tert-butoxide (15.2 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 20.1 g of a white solid, yield 82.4%.

[0198] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + 310.17 (Theoretical value: 309.12).

[0199] Synthesis of intermediate A2:

[0200] At room temperature, A2-1 (20.0 g), p-(4-tert-butylphenyl)bromobenzene (18.7 g), Pd(dppf)Cl2 (2.4 g), sodium tert-butoxide (12.4 g), and toluene (400 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 28.7 g of a white solid, with a yield of 85.7%.

[0201] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + 518.23 (Theoretical value: 517.24).

[0202] Synthesis of intermediate M113-1:

[0203] At room temperature, M113-0 (16.0 g) and p-tert-butyl (4 g) were added. ， 25.4 g of tert-butylbiphenyl aniline, 3.2 g of Pd₂(dba)₃, 1.4 g of tri-tert-butylphosphine, 13.6 g of sodium tert-butoxide, and 500 mL of toluene 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with plenty of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to give 27.4 g of product, with a yield of 76.8%.

[0204] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + 502.35 (Theoretical value: 501.20).

[0205] Synthesis of intermediate M113-2:

[0206] At room temperature, M113-1 (18.0 g), A2 (18.5 g), Pd2(dba)3 (1.6 g), tri-tert-butylphosphine (0.7 g), sodium tert-butoxide (6.9 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 29.8 g of a white solid, with a yield of 89.8%.

[0207] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 983.40 (Theoretical value: 982.46).

[0208] Synthesis of compound M113:

[0209] At room temperature, M113-2 (20.0 g) was dissolved in 120 mL of xylene. After purging with nitrogen three times, the reaction system was cooled to -20 °C, and then tert-butyllithium (19 mL, 1.6 M) was added. The mixture was stirred at this low temperature for 30 minutes. The temperature was then gradually increased to 60 °C and maintained for 2 hours. Finally, the temperature of the reaction system was lowered back to -20 °C, and boron tribromide (5 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (17 mL) was added. The reaction system was then heated to 120 °C and reacted for 8 hours. After cooling to room temperature, the organic phase was evaporated to dryness under reduced pressure. The organic phases were extracted three times with dichloromethane (200 mL), combined, dried over anhydrous sodium sulfate, concentrated with silica gel, and subjected to column chromatography (PE:DCM = 20:1) to obtain a crude product. Recrystallization yielded 2.1 g of a yellow solid, with a yield of 10.8%.

[0210] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 957.63 (Theoretical value: 956.49).

[0211] Synthesis Example 3: Synthesis of M252

[0212]

[0213] Synthesis of intermediate A3:

[0214] At room temperature, Al-O (20.0 g), N1,N1-diphenyl-1,3-phenylenediamine (20.6 g), Pd(dppf)Cl2 (2.9 g), sodium tert-butoxide (15.2 g), and toluene (400 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 29.5 g of a white solid, with a yield of 78.2%.

[0215] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 477.22 (Theoretical value: 476.19).

[0216] Synthesis of intermediate M252-1:

[0217] At room temperature, M252-0 (20.0 g), N1,N1-diphenyl-1,3-phenylenediamine (22.3 g), Pd(dppf)Cl2 (3.1 g), sodium tert-butoxide (16.5 g), and toluene (400 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 mixture was cooled to room temperature, concentrated, extracted with dichloromethane, washed thoroughly with water, dried, and concentrated for column chromatography (PE:DCM = 10:1) to obtain 30.2 g of product, with a yield of 85.4%.

[0218] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + 413.25 (Theoretical value: 412.19).

[0219] Synthesis of intermediate M252-2:

[0220] At room temperature, M252-1 (20.0 g), 1-bromo-2,3-dichlorobenzene (11.0 g), Pd2(dba)3 (2.2 g), tri-tert-butylphosphine (1.0 g), sodium tert-butoxide (9.3 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 22.3 g of a white solid, with a yield of 82.7%.

[0221] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + 557.26 (Theoretical value: 556.15).

[0222] Synthesis of intermediate M252-3:

[0223] At room temperature, M252-2 (20.0 g), A3 (17.1 g), Pd2(dba)3 (1.6 g), tri-tert-butylphosphine (0.7 g), sodium tert-butoxide (6.9 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 29.4 g of a white solid, with a yield of 82.2%.

[0224] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 997.41 (Theoretical value: 996.36).

[0225] Synthesis of compound M252:

[0226] At room temperature, M252-3 (20.0 g) was dissolved in 120 mL of xylene. After purging with nitrogen three times, the reaction system was cooled to -20 °C, and then tert-butyllithium (19 mL, 1.6 M) was added. The mixture was stirred at this low temperature for 30 minutes. The temperature was then gradually increased to 60 °C and maintained for 2 hours. Finally, the temperature of the reaction system was lowered back to -20 °C, and boron tribromide (5 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (17 mL) was added. The reaction system was then heated to 120 °C and reacted for 8 hours. After cooling to room temperature, the organic phase was evaporated to dryness under reduced pressure. The organic phases were extracted three times with dichloromethane (200 mL), combined, dried over anhydrous sodium sulfate, concentrated with silica gel, and subjected to column chromatography (PE:DCM = 20:1) to obtain a crude product. Recrystallization yielded 3.6 g of a yellow solid, with a yield of 18.5%.

[0227] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 971.26 (Theoretical value: 970.38).

[0228] Synthesis Example 4: Synthesis of M345

[0229]

[0230] Synthesis of intermediate A4-1:

[0231] At room temperature, A4-0 (20.0 g), pinacol ester of p-aminophenylboronic acid (17.4 g), Pd2(dba)3 (3.6 g), Sphos (3.3 g), sodium tert-butoxide (15.2 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 20.2 g of a white solid, with a yield of 82.6%.

[0232] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + 326.03 (Theoretical value: 325.09).

[0233] Synthesis of intermediate A4:

[0234] At room temperature, A4-1 (20.0 g), 3-bromo-5-(tert-butyl)benzo[b]thiophene (16.5 g), Pd(dppf)Cl2 (2.2 g), sodium tert-butoxide (11.8 g), and toluene (400 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 26.4 g of a white solid, with a yield of 83.8%.

[0235] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + 514.12 (Theoretical value: 513.16).

[0236] Synthesis of intermediate M8-1:

[0237] At room temperature, M8-0 (20.0 g), bis(p-tert-butyl)aniline (20 g), Pd2(dba)3 (3.2 g), tri-tert-butylphosphine (1.4 g), sodium tert-butoxide (13.6 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 mixture was cooled to room temperature, concentrated, extracted with dichloromethane, washed thoroughly with water, dried, and concentrated for column chromatography (PE:DCM = 10:1) to obtain 27.8 g of product, with a yield of 81.3%.

[0238] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 482.24 (Theoretical value: 481.23).

[0239] Synthesis of intermediate M345-2:

[0240] At room temperature, M8-1 (20.0 g), A4 (21.3 g), Pd2(dba)3 (1.9 g), tri-tert-butylphosphine (0.8 g), sodium tert-butoxide (8.0 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 30.2 g of a white solid, with a yield of 76.1%.

[0241] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 959.32 (Theoretical value: 958.41).

[0242] Synthesis of compound M345:

[0243] At room temperature, M345-2 (20.0 g) was dissolved in 120 mL of xylene. After purging with nitrogen three times, the reaction system was cooled to -20 °C, and then tert-butyllithium (20 mL, 1.6 M) was added. The mixture was stirred at this low temperature for 30 minutes. The temperature was then gradually increased to 60 °C and maintained for 2 hours. Finally, the temperature of the reaction system was lowered back to -20 °C, and boron tribromide (5 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (17 mL) was added. The reaction system was then heated to 120 °C and reacted for 8 hours. After cooling to room temperature, the organic phase was evaporated to dryness under reduced pressure. The organic phases were extracted three times with dichloromethane (200 mL), combined, dried over anhydrous sodium sulfate, concentrated with silica gel, and subjected to column chromatography (PE:DCM = 20:1) to obtain a crude product. Recrystallization yielded 3.5 g of a yellow solid, with a yield of 18.0%.

[0244] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 933.34 (Theoretical value: 932.44).

[0245] Synthesis Example 5: Synthesis of M414

[0246]

[0247] Synthesis of intermediate A5:

[0248] At room temperature, A5-0 (15.0 g), 4-tert-butylaniline (7.4 g), Pd(dppf)Cl2 (1.8 g), sodium tert-butoxide (9.5 g), and toluene (400 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 17.6 g of a white solid, with a yield of 85.4%.

[0249] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 416.17 (Theoretical value: 415.19).

[0250] Synthesis of intermediate M414-1:

[0251] At room temperature, M8-0 (20.0 g) and p-tert-butyl (4 g) were added. ， 25.4 g of tert-butylbiphenyl aniline, 3.2 g of Pd₂(dba)₃, 1.4 g of tri-tert-butylphosphine, 13.6 g of sodium tert-butoxide, and 500 mL of toluene 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to give 29.5 g of product, a yield of 74.3%.

[0252] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + 558.21 (Theoretical value: 557.26).

[0253] Synthesis of intermediate M414-2:

[0254] At room temperature, M414-1 (22.0 g), A5 (16.5 g), Pd2(dba)3 (1.8 g), tri-tert-butylphosphine (0.8 g), sodium tert-butoxide (7.6 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 mixture was cooled to room temperature, concentrated, and extracted with dichloromethane. After washing with copious amounts of water, the organic phase was dried and concentrated for column chromatography (PE:DCM = 10:1) to obtain a crude product. Methanol was then added and the mixture was stirred to obtain 29.7 g of a white solid, with a yield of 79.8%.

[0255] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 937.41 (Theoretical value: 936.48).

[0256] Synthesis of compound M414:

[0257] At room temperature, M414-2 (20.0 g) was dissolved in 120 mL of xylene. After purging with nitrogen three times, the reaction system was cooled to -20 °C, and then tert-butyllithium (20 mL, 1.6 M) was added. The mixture was stirred at this low temperature for 30 minutes. The temperature was then gradually increased to 60 °C and maintained for 2 hours. Finally, the temperature of the reaction system was lowered back to -20 °C, and boron tribromide (5 mL) was added under nitrogen protection. After stirring for 30 minutes, diisopropylethylamine (17 mL) was added. The reaction system was then heated to 120 °C and reacted for 8 hours. After cooling to room temperature, the organic phase was evaporated to dryness under reduced pressure. The organic phases were extracted three times with dichloromethane (200 mL), combined, dried over anhydrous sodium sulfate, concentrated with silica gel, and subjected to column chromatography (PE:DCM = 20:1) to obtain a crude product. Recrystallization yielded 3.6 g of a yellow solid, with a yield of 18.5%.

[0258] The molecular ion mass [M+H] determined by ESI source analysis of mass spectrometry + : 911.42 (Theoretical value: 910.50).

[0259] Device Example 1

[0260] An organic electroluminescent device includes 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:

[0261] (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.

[0262] (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.

[0263] (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 60 nm.

[0264] (4) The compound HT-14 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.

[0265] (5) A light-emitting layer is vacuum-deposited on the electron blocking layer. The light-emitting layer comprises a binary mixture of the host material BFH-4 and the dye (the aromatic compound M8 provided by the present invention), BFH-4:M8 (100:3, w / w), the deposition rate is 0.1 nm / s, and the total deposition film thickness is 20 nm.

[0266] (6) The compound ET-23 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.

[0267] (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.

[0268] (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.

[0269] (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.

[0270] Device Examples 2-14, Device Comparative Examples 1-2

[0271] An organic electroluminescent device is disclosed, which differs from device example 1 only in that the dyes of the light-emitting layer are the compounds shown in Table 1; the other layers, thicknesses, materials and preparation methods are the same as those of device example 1.

[0272] The dyes used in Comparative Examples 1-2 of the devices are shown below:

[0273]

[0274] Device performance testing:

[0275] (1) Maximum emission wavelength (λ) max ) and FWHM: by fluorescence spectroscopy at 1.0*10 -5 Measured in a toluene solution of mol / L;

[0276] (2) LT97 lifespan: using a luminance meter at 40mA / cm 2 The initial brightness value of the device was tested under current density. A constant current was maintained, and the time it took for the device brightness to drop to 97% of the initial brightness was measured in hours. The LT97 lifetime test value of device Comparative Example 1 was recorded as 1.0, and the ratio of the LT97 lifetime test value of other devices to the LT97 lifetime test value of device Comparative Example 1 was calculated.

[0277] (3) External quantum efficiency: 10 mA / cm² was measured using the integrating sphere method. 2 The external quantum efficiency (EQE, %) of the device at current density is calculated, with the external quantum efficiency test value of device comparison example 1 recorded as 1.0. The ratio of the external quantum efficiency test value of other devices to the external quantum efficiency test value of device comparison example 1 is calculated.

[0278] The test results are shown in Table 1:

[0279] Table 1

[0280]

[0281]

[0282] As can be seen from Table 1, the aromatic compounds provided by this invention are suitable as dyes for use in organic electroluminescent devices, and can effectively improve the luminous efficiency and lifespan of the devices.

[0283] Device Example 15

[0284] An organic electroluminescent device includes 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:

[0285] (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.

[0286] (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.

[0287] (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.

[0288] (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.

[0289] (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 (5:4, w / w), sensitizer BPD-1 (13% doped based on 100% of the total host material) and dye (1% doped with polycyclic aromatic compound M8 provided by the present invention). The total evaporation rate is 0.1 nm / s and the total evaporation film thickness is 35 nm.

[0290] (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.

[0291] (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.

[0292] (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.

[0293] (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.

[0294] Device Examples 16-25, Device Comparative Examples 3-4

[0295] An organic electroluminescent device is disclosed, which differs from device example 15 only in 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 15.

[0296] The dyes used in Comparative Examples 3-4 of the devices are C1 and C2 as described above.

[0297] Device performance testing:

[0298] (1)λ max FWHM: directly measured by organic electroluminescent devices;

[0299] (2) LT95 lifespan: using a luminance meter at 40mA / cm 2 The initial brightness value of the device was tested under the current density. The current was kept constant, and the time it took for the device brightness to drop to 95% of the initial brightness was measured in hours. The LT95 lifetime test value of device Comparative Example 3 was recorded as 1.0, and the ratio of the LT95 lifetime test value of other devices to the LT95 lifetime test value of device Comparative Example 3 was calculated.

[0300] (3) External quantum efficiency: 10 mA / cm² was measured using the integrating sphere method. 2The external quantum efficiency (EQE, %) of the device at current density is calculated, with the external quantum efficiency test value of device comparison example 3 recorded as 1.0. The ratio of the external quantum efficiency test values ​​of other devices to the external quantum efficiency test value of device comparison example 3 is calculated.

[0301] The test results are shown in Table 2:

[0302] Table 2

[0303] dye <![CDATA[λ max (nm)]]> FWHM(nm) LT95 EQE Device Example 15 M8 463 29 1.9 1.5 Device Example 16 M97 461 28 1.7 1.4 Device Example 17 M113 465 29 2.1 1.5 Device Example 18 M146 464 28 1.9 1.6 Device Example 19 M176 463 27 2.3 1.4 Device Example 20 M251 462 28 2.4 1.5 Device Example 21 M290 463 28 1.9 1.5 Device Example 22 M345 463 27 2.2 1.6 Device Example 23 M414 464 28 2.0 1.6 Device Example 24 M421 460 28 2.1 1.5 Device Example 25 M426 464 29 1.9 1.4 Device Comparison Example 3 C1 464 30 1 1 Device Comparison Example 4 C2 462 32 1.3 1.2

[0304] As can be seen from Table 2, the aromatic compounds provided by this invention are suitable as dyes for use in organic electroluminescent devices, and can effectively improve the luminous efficiency and lifespan of the devices.

[0305] In summary, using the aromatic compounds provided by this invention in organic electroluminescent devices can effectively narrow the full width at half maximum (FWHM), improve color purity, increase efficiency and lifespan, making them high-performance blue light materials.

[0306] The applicant declares that the present invention illustrates the aromatic compounds and their applications through the above embodiments, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An aromatic compound, characterized by, The aromatic compound has a structure as shown in formula (1): In formula (1), each of ring A, ring D, and ring E is independently selected from any one of a substituted or unsubstituted C6-C50 aromatic ring and a substituted or unsubstituted C3-C30 heteroaromatic ring; Each of X1 and X2 is independently O, S, or NAr1, and each of Ar1 is independently selected from any one of a group shown in formula (2), a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; At least one of ring A, ring D, ring E, and Ar1 is substituted by the group shown in formula (2), and / or Ar1 is the group shown in formula (2); The group shown in formula (2) is connected to formula (1) at any site allowed by a chemical environment; In formula (2), X3is O, NR 11 or S; Y1-Y 10 each independently selected from N, CR 12 or C, and wherein at least one is C, said C being attached to formula (1); or, Y1-Y 10 each independently selected from N or CR 12 , and having two adjacent R 12 are attached to form a ring by a chemical bond, said ring being attached to formula (1); R 11 , R 12 each independently is selected from any one of hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; two adjacent R 12 are not connected or connected by a chemical bond to form a ring; Rings A, D, E, Ar1, R 11 , R 12 each independently of one another are selected from the group consisting of any one of or a combination of at least two of halogen, cyano, C1-C20 linear or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 silylaryl.

2. The aromatic compound according to claim 1, characterized by Each of ring A and ring D independently has a structure as shown in formula (a) or formula (b): The dotted line represents a connection site of the group; X4 is selected from O or S; Each of U1 to U8 is independently selected from CR2 or N; Each of R2 is independently selected from any one of a group shown in formula (2), hydrogen, halogen, cyano, a substituted or unsubstituted C1-C20 straight-chain or branched alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C3-C30 heteroarylamino group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C3-C30 heteroaryloxy group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group; two adjacent R2 are not connected or are connected into a ring by a chemical bond; Preferably, each of R2 is independently selected from any one of a group shown in formula (2), hydrogen, halogen, cyano, a substituted or unsubstituted C1-C20 straight-chain or branched alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a C3-C30 heteroaryl group, and the substituent is any one of halogen and a C1-C5 straight-chain or branched alkyl group.

3. The aromatic compound according to claim 1 or 2, characterized by The ring E has a structure as shown in formula (c): The dotted line represents a connection site of the group; Each of Z1, Z2, and Z3 is independently selected from CR3 or N; Each of R3 is independently selected from any one of a group shown in formula (2), hydrogen, halogen, cyano, a substituted or unsubstituted C1-C20 straight-chain or branched alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C3-C30 heteroarylamino group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C3-C30 heteroaryloxy group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, and a substituted or unsubstituted C6-C30 silyl aryl group; Preferably, each of R3 is independently selected from any one of a group represented by formula (2), hydrogen, halogen, cyano, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, C3-C30 heteroaryl, wherein the substituted substituent is any one of halogen, C1-C5 linear or branched alkyl, C6-C18 aryl, C3-C18 heteroaryl; Preferably, the formula (1) has a structure as shown in the following formula (1): wherein X1, X2 have the same defined range as claim 1; X4 is selected from O or S; x, y are each independently an integer from 0 to 3; z is an integer from 0 to 2; each of R2 is independently selected from any one of a group represented by formula (2), halogen, cyano, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino, wherein the substituted substituent is any one of halogen, C1-C5 linear or branched alkyl; two adjacent R2 are not connected or connected into a ring by a chemical bond; each of R3 is independently selected from any one of a group represented by formula (2), halogen, cyano, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, C3-C30 heteroaryl, wherein the substituted substituent is any one of halogen, C1-C5 linear or branched alkyl, C6-C18 aryl, C3-C18 heteroaryl.

4. The aromatic compound according to claim 1, characterized by each of X1, X2 is NAr1, and two Ar1 are each independently selected from any one of a group represented by formula (2) or the following formula (2a): wherein the dotted line represents a connecting site of a group; R 21 -R 24 each independently is selected from any one of a group represented by formula (2), a substituted or unsubstituted C1-C20 linear or branched alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group; the substituted substituent is any one of deuterium, halogen, C1-C10 linear or branched alkyl group; two adjacent R 21 , two adjacent R 22 , two adjacent R 24 are not connected or are connected into a ring by a chemical bond; n1 is selected from an integer from 0 to 5, n2 is selected from an integer from 0 to 5, n3 is selected from an integer from 0 to 4, n4 is selected from an integer from 0 to 5; Preferably, R 21 -R 24 Each group is independently selected from any one of the groups shown in formula (2), C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, and C6-C30 aryl groups; the substituted substituents are any one of deuterium, halogen, and C1-C5 straight-chain or branched alkyl groups; Preferably, each of X1, X2 is NAr1, and two Ar1 are each independently selected from any one of a group represented by formula (2) or the following formula (2a): R 21 is selected from the group consisting of radicals of formula (2).

5. The aromatic compound according to claim 1, wherein at least one of Y1-Y4 is C, and the C is connected to formula (1); Preferably, at least one of Y1-Y4 is C, said C being attached to formula (1), and at most one of the remaining Y is N, the remaining Y each being independently selected from the group consisting of CR 12 ; R 12 each independently is selected from the group consisting of any one of hydrogen, halogen, cyano, C1-C20 straight chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, C3-C30 heteroaryl; Preferably, said R 12 each independently is selected from any one of hydrogen, cyano, C1-C10 linear or branched alkyl, C2-C10 alkenyl, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamino; Preferably, said R 11 any one selected from the group consisting of hydrogen, cyano, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; Preferably, said R 11 any one selected from the group consisting of hydrogen, cyano, C1-C10 straight chain or branched chain alkyl, C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, the substituent of which is C1-C5 straight chain or branched chain alkyl.

6. The aromatic compound according to claim 1, wherein the formula (2) has a structure as shown in the following formula (2): wherein the dotted line represents a connecting site of a group; X3is O, NR 11 or S, R 11 is selected from any one of hydrogen, cyano, C1-C10straight chain or branched alkyl, C3-C10cycloalkyl, substituted or unsubstituted C6-C30aryl, the substituents of which are C1-C5straight chain or branched alkyl.

7. The aromatic compound according to any one of claims 1 to 6, characterized by the aromatic compound has any one of a structure as shown in the following formula (3a) or (3b):

8. Use of an aromatic compound as claimed in any one of claims 1 to 7, characterized in that, the aromatic compound is applied to an organic electronic device; Preferably, the organic electronic device includes any one or a combination of at least two of an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper; Preferably, the aromatic compound is used as a light-emitting layer material in an organic electronic device, and more preferably as a light-emitting dye in a light-emitting layer.

9. An organic electroluminescent device, characterized by The organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer arranged between the first and second electrodes; the organic layer comprises at least one aromatic compound according to any one of claims 1 to 7; Preferably, the organic layer comprises an emission layer, the emission layer comprises at least one aromatic compound according to any one of claims 1 to 7; Preferably, the emission layer comprises a host material and an emission dye, the emission dye comprises at least one aromatic compound according to any one of claims 1 to 7.

10. A display device, characterized by comprising: The display device comprises the organic electroluminescent device according to claim 9.

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