Organic compound and use thereof, and organic electroluminescent device

Abstract

Disclosed are an organic compound and the use thereof, and an organic electroluminescent device. The organic compound has a structure as represented by formula I. By means of a structural design and the interaction between groups, the organic compound has good photoelectric properties and good hole transport / injection performance. The organic compound is used in an organic electroluminescent device as a host material of a light-emitting layer, has good carrier transport performance, and enables energy transfer between a host and a guest to be more effective, thereby improving the utilization rate of excitons; therefore, the luminous efficiency of the device is effectively improved, the service life of the device is significantly prolonged, the voltage is reduced, and the comprehensive light-emitting performance of the device is optimized.

Description

An organic compound and its applications, organic electroluminescent devices Technical Field

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

[0002] In recent years, optoelectronic devices based on organic materials have developed rapidly and have gradually become a research hotspot in the field. Examples of organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors, organic photovoltaic cells, and organic sensors. Among them, the development of OLEDs has been particularly rapid, and they have already achieved commercial success in the field of information display. OLEDs can provide highly saturated red, green, and blue colors. Full-color display devices made with OLEDs do not require an additional backlight and have advantages such as vibrant colors, flexibility, thinness, low cost, high efficiency, and low energy consumption.

[0003] The core of OLED devices is a multilayer thin-film structure containing various functionalized organic materials. Common functionalized organic materials include: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, 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] Currently, OLEDs can be categorized by their light-emitting mechanism into fluorescence, phosphorescence, thermally excited delayed fluorescence (TADF), and thermally excited sensitized fluorescence (TASF). Common phosphors 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 and platinum complexes) can simultaneously utilize both triplet and singlet excitons for light emission, and are called phosphors, with energy conversion efficiencies up to four times higher than traditional phosphors. Thermally excited delayed fluorescence (TADF) promotes the conversion of triplet excitons to singlet excitons, achieving high luminous 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 luminous efficiency.

[0005] Although products using OLED technology are commercialized, there is still a need to continuously improve the efficiency, voltage, and lifespan of these devices to meet people's demands for high-quality display effects. Therefore, there is an urgent need in this field to develop more types and higher-performance organic materials for use in organic electroluminescent devices, enabling the devices to have better light-emitting effects. Summary of the Invention

[0006] To address the shortcomings of existing technologies, the purpose of this disclosure is to provide an organic compound and its applications, as well as an organic electroluminescent device. Through molecular structure design, the organic compound possesses excellent photoelectric properties, making it particularly suitable as a host material for the light-emitting layer in organic electroluminescent devices. This effectively improves the luminous efficiency and lifespan of the device while reducing voltage.

[0007] To achieve this objective, the present disclosure adopts the following technical solution:

[0008] In a first aspect, this disclosure provides an organic compound having the structure shown in Formula I:

[0009] In Equation I, X1 and X2 are each independently selected from N, O or S, and there is one and only one of them being N.

[0010] In Formula I, Ar1 and Ar2 are each independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups.

[0011] In Formula I, L1, L2, and L3 are each independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene. When L1 is a single bond, it represents that Ar1 and N atoms are directly connected by a single bond; when L2 is a single bond, it represents that a fused ring structure is directly connected to N atoms by a single bond; when L3 is a single bond, it represents that a dibenzofuran structure is directly connected to N atoms by a single bond.

[0012] In Formula I, R1 is selected from any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino.

[0013] In Formula I, R2, R3, R4, and R5 are each independently selected from any one of deuterium, halogen, cyano, substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino.

[0014] R1 and R2 are each independently unconnected to adjacent ring structures or connected to each other via chemical bonds to form a ring. In this disclosure, "each R1 is independently unconnected to adjacent ring structures" means that R1 is only connected to C atoms via single bonds; "each R1 is independently connected to adjacent ring structures via chemical bonds" means that R1, in addition to being connected to C atoms via chemical bonds, is also connected to adjacent rings via chemical bonds, thereby forming a fused ring structure. R2 is similar, and for the sake of simplicity, it will not be described in detail.

[0015] In this disclosure, R3, R4, and R5 are only connected to C atoms through single bonds and are not connected to or fused with adjacent rings.

[0016] In Formula I, a, b, c, d, and e represent the number of substituents R1, R2, R3, R4, and R5, respectively. a is an integer selected from 1 to 3, for example, 1, 2, or 3; b and c are each independently selected from 0 to 4, for example, 0, 1, 2, 3, or 4; d and e are each independently selected from 0 to 2, for example, 0, 1, or 2; 0 ≤ c + d + e ≤ 7.

[0017] It should be noted that when a≥2, multiple (at least 2) R1s are the same or different groups; when b≥2, multiple (at least 2) R2s are the same or different groups; the same applies to c, d, and e. For the sake of brevity, they will not be elaborated further.

[0018] The substituents in Ar1, Ar2, L1, L2, L3, R1, R2, R3, R4, and R5 are each independently selected from at least one of deuterium, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; each substituent is independently not connected to the adjacent ring structure or is connected to the ring structure by a chemical bond.

[0019] In this disclosure, "each of the substituents is independently not connected to the adjacent ring structure" means that the substituent is only connected to the C atom through a single bond; "each of the substituents is independently connected to the adjacent ring structure through chemical bonds to form a ring" means that the substituent is connected to the C atom through chemical bonds, and also to the adjacent ring through chemical bonds, thereby forming a fused ring structure. The same descriptions will have the same meaning in the following text and will not be repeated hereafter.

[0020] In the present disclosure, the "substituted or unsubstituted" group may be substituted with one substituent or multiple substituents. When there are multiple substituents (at least two), they may be the same or different substituents; when the same expression is involved hereinafter, it shall have the same meaning. Unless otherwise specified, the selection range of the substituents in Formula I and Formula II is as shown above and will not be elaborated further.

[0021] In the present disclosure, the hydrogen at any position on the organic compound having the structure shown in Formula I may be optionally substituted with deuterium.

[0022] In the present disclosure, the dashed arc in Formula I represents the conjugated double bond in the five-membered ring, that is, the structure of the organic compound may be any one of the following:

[0023] In Formula IA, X1 is O or S. In Formula IB, X2 is O or S.

[0024] The organic compound provided by the present disclosure is as shown in Formula I, and its parent nucleus structure includes an aromatic amine structure. A dibenzofuran (DBF) group is connected to the aromatic amine structure, and a group R1 with strong conjugation is introduced from the same side where the DBF is connected to the aromatic amine. At the same time, a heteroaromatic group containing a phenanthrene structure is also connected to the aromatic amine to construct a larger conjugated system. Through the structural design and the interaction between groups in the present disclosure, the organic compound has excellent optoelectronic properties and hole transport / injection performance. As a host material for the light-emitting layer in an organic electroluminescent device, it has excellent carrier transport performance, makes the host-guest energy transfer more effective, improves the exciton utilization rate, thereby effectively enhancing the light-emitting efficiency of the device, prolonging the lifespan, and reducing the voltage. <​​​​​​​​​​​​​​​​C, etc. Hydrogen at any site on the compound shown in Formula I may optionally be substituted with deuterium.

[0028] In this disclosure, unless otherwise specified, the heteroatom of the heteroaryl group is selected from N, O, S, P, B, Si or Se, or may be N, O or S.

[0029] In this disclosure, the way a ring structure is represented by a dash ("—") indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0030] In this disclosure, "——*" and "*" both represent the linking sites of functional groups.

[0031] In this disclosure, “each independently” means that when there are multiple subjects, they may be the same or different from each other.

[0032] In this disclosure, the halogens mentioned can be fluorine, chlorine, bromine, or iodine. The same descriptions used below have the same meaning.

[0033] In this disclosure, the expression Ca-Cb represents that the group has ab carbon atoms. Unless otherwise specified, the number of carbon atoms does not include the number of carbon atoms of the substituents.

[0034] In this disclosure, C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0035] C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0036] C1-C30 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C20, C22, C24, C26 or C28, etc.

[0037] C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0038] C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0039] C3-C20 can all be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.

[0040] C6-C60 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56 or C58, etc.

[0041] C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, or C58, etc.

[0042] In this disclosure, the C6-C60 aryl, C6-C30 aryl, or C6-C25 aryl, and further, C6-C20 aryl, include monocyclic aryl and fused-ring aryl; the monocyclic aryl means that the group contains at least one phenyl group, and when it contains at least two phenyl groups, the phenyl groups are linked by single bonds, including but not limited to: phenyl, biphenyl, terphenyl, tetraphenyl, etc. The term "fused-ring aryl" refers to a group containing at least two aromatic rings, wherein the aromatic rings share two adjacent carbon atoms fused together. Exemplary examples include, but are not limited to: naphthyl (1-naphthyl, 2-naphthyl), anthraceneyl (1-anthrayl, 2-anthrayl, 9-anthrayl), phenanthryl, indene, fluorenyl and their derivatives (9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, phenylmethylfluorenyl, spirodifluorenyl, benzo[a]fluorenyl, etc.), fluoranyl, triphenylene, pyrene (1-pyrene, 2-pyrene, 4-pyrene), peryl, Aryl, tetraphenyl (1-benzotetraphenyl, 2-benzotetraphenyl, 9-benzotetraphenyl), acenaphthenyl, benzo[a]acenaphthenyl, etc. It should be noted that monocyclic aryl and fused-ring aryl groups linked by single bonds also fall under the aryl group category, such as phenylnaphthyl and naphthylphenyl.

[0043] The C3-C60 and C3-C30 heteroaryl groups can be C3-C20 heteroaryl groups, 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, etc.), the heteroaryl group and other groups are connected by a single bond, exemplarily including but not limited to: pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophene, pyrroleyl, bipyridinyl, phenylpyridinyl, pyridylphenyl, pyrimidinylphenyl, 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: quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, isobenzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, carbazoleyl and its derivatives (N-phenylcarbazoleyl, N-naphthylcarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, azacarbazoleyl, indocarbazoleyl, etc.), benzoxazolyl, acridineyl, phenazinyl, phenothiazinyl, phenothiazinyl, hydrogenated acridineyl, etc. It should be noted that heteroaryl groups connected by single bonds, as well as aryl groups connected by single bonds, also fall under the category of heteroaryl groups, such as phenyldibenzofuranyl and phenyldibenzothiopheneyl.

[0044] Specific examples of the C6-C30 arylene group can be exemplified by removing one hydrogen atom from the aryl group examples above, resulting in a divalent group; specific examples of the C3-C30 heteroarylene group can be exemplified by removing one hydrogen atom from the heteroaryl group examples above, resulting in a divalent group.

[0045] Specific examples of the C6-C30 aryloxy group can be exemplified by the monovalent group obtained by attaching the aforementioned aryl group to O. Specific examples of the C3-C30 heteroaryloxy group can be exemplified by the monovalent group obtained by attaching the aforementioned heteroaryl group to O.

[0046] Specific examples of the C6-C30 arylamino group are monovalent groups formed by substituting at least one hydrogen atom in the -NH2 group with the aforementioned aryl group, including but not limited to: phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, biphenylamino, etc. Specific examples of the C3-C30 heteroarylamino group are monovalent groups formed by substituting at least one hydrogen atom in the -NH2 group with the aforementioned heteroaryl group, including but not limited to: pyridinylamino, pyrimidinylamino, dibenzofuranylamino, etc.

[0047] The C1-C30 straight-chain or branched alkyl group, or the C1-C20 straight-chain or branched alkyl group, can be a C1-C16 straight-chain or branched alkyl group, and can further be a C1-C10 straight-chain or branched alkyl group. Exemplary examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, 2-methylbutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, neohexyl, 2-ethylhexyl, n-octyl, n-heptyl, n-nonyl, n-decyl, etc.

[0048] Specific examples of the C1-C30 alkoxy and C1-C20 alkoxy groups can be given by connecting the above-mentioned straight-chain or branched alkyl groups with O to obtain monovalent groups.

[0049] A specific example of the C1-C20 alkylsilyl group is a monovalent group obtained by replacing at least one hydrogen in -SiH3 with the above-mentioned straight-chain or branched alkyl group; a specific example of the C1-C20 alkylamino group is a monovalent group obtained by replacing at least one hydrogen in -NH2 with the above-mentioned straight-chain or branched alkyl group.

[0050] The C2-C20 alkenyl group can also be a C2-C10 alkenyl group, which contains at least one C=C, including but not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0051] The C3-C30 cycloalkyl and C3-C20 cycloalkyl groups can be C3-C10 cycloalkyl groups, including monocycloalkyl or polycycloalkyl groups. Monocycloalkyl refers to an alkyl group containing a single ring structure, while polycycloalkyl refers to a structure formed by two or more cycloalkyl groups sharing one or more carbon atoms on a ring; exemplary examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0052] Specific examples of the C2-C20 heterocyclic alkyl group include groups formed by replacing at least one C atom in the aforementioned cycloalkyl group with a heteroatom (e.g., N, O, S, etc.), including but not limited to: epoxy group, oxetane, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydropyrroleyl, tetrahydropyranyl, piperidinyl, piperazineyl, dioxaneyl, morpholinyl, etc.

[0053] A specific example of the C1-C30 alkylsilyl group is a monovalent group formed by replacing at least one H on -SiH3 with one of the straight-chain or branched alkyl groups listed above.

[0054] In one embodiment, the organic compound has a structure as shown in Formula II:

[0055] Where X1 is O or S; Ar1, Ar2, L1, L2, L3, R1, R2, R3, R4, R5, a, b, c, d and e have the same range of limitation as in Equation I.

[0056] In one embodiment, L3 is selected from any one of single-bonded, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16 or C18, etc.) arylene groups, and may further be any one of single-bonded, substituted or unsubstituted groups such as: phenylene, biphenylene, naphthylene. In one embodiment, L3 is a single bond.

[0057] In one embodiment, the organic compound has a structure as shown in any one of formulas III-1 to III-12:

[0058] Wherein, X1 is O or S, and in one embodiment it can also be O; Ar1, Ar2, L1, L2, R1, R2, R3, R4, R5, b, c, d, e have the same range of definition as in Formula I.

[0059] In one embodiment, the organic compound has a structure as shown in any one of Formula III-1, Formula III-2, Formula III-3, or Formula III-4.

[0060] In one embodiment, Ar1 and Ar2 are each independently selected from any one of substituted or unsubstituted C6-C25 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, C22, or C24, etc.) aryl groups and substituted or unsubstituted C5-C20 (e.g., C5, C6, C9, C10, C12, C14, C15, C16, or C18, etc.) heteroaryl groups.

[0061] In one embodiment, Ar1 and Ar2 are each independently selected from any one of the following groups, either substituted or unsubstituted:

[0062] In this context, —* represents the linking site of a functional group.

[0063] Y1 is selected from O, S, NR 11 or CR 12 R 13 Any one of them.

[0064] R A R 11 R 12 R 13Each is independently selected from any one or a combination of at least two of the following: C1-C20 straight-chain or branched alkyl, C6-C30 aryl, C3-C30 heteroaryl, and C2-C20 alkenyl; The R 12 and R 13 They can be either not connected or linked together by chemical bonds to form a ring.

[0065] In one implementation, the R A R 11 R 12 R 13 Each of the following is independently selected from any one or a combination of at least two of the following: C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl groups, and C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, or C18, etc.). It can also be any one of C1-C6 straight-chain or branched alkyl groups, phenyl, naphthyl, biphenyl, terphenyl, phenylnaphthyl, naphthylphenyl, and even further, it can be methyl or phenyl.

[0066] In one implementation, the R 12 and R 13 They can be formed into spirofluorene groups either without bonding or by chemical bonds.

[0067] In one embodiment, the substituents in Ar1 and Ar2 are each independently selected from deuterium, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aryl groups, and C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaryl groups, or combinations of at least two of these substituents; each substituent is independently not connected to the adjacent ring structure or is connected to the ring structure by a chemical bond to form a ring.

[0068] In one embodiment, the substituents in Ar1 and Ar2 are each independently selected from any one of deuterium, C1-C6 straight-chain or branched alkyl, phenyl, naphthyl, biphenyl, and pyridyl. In another embodiment, they are selected from any one of deuterium, methyl, ethyl, isopropyl, isobutyl, tert-butyl, tert-amyl, phenyl, naphthyl, biphenyl, and pyridyl.

[0069] In one embodiment, Ar1 and Ar2 are each independently selected from any one of the following unsubstituted or deuterated groups:

[0070] In this context, —* represents the linking site of a functional group.

[0071] Furthermore, in one embodiment, the Ar2 is selected from any one of the following groups: phenyl, naphthyl, biphenyl, terphenyl, pyridyl.

[0072] In one embodiment, L1 and L2 are each independently selected from any one of single-bonded, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C13, C14, C15, C16 or C18, etc.) arylene, and substituted or unsubstituted C5-C20 (e.g., C6, C7, C8, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl.

[0073] In one embodiment, L1 and L2 are each independently selected from any one of the following groups: single bond, substituted or unsubstituted: In this context, —* represents the linking site of a functional group.

[0074] In one embodiment, R1 is selected from substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy groups, substituted or unsubstituted C2-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) alkenyl groups, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, and substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, etc.) groups. Any one of aryl groups (C16, C18, C20, C22, C24, C26 or C28, etc.) or substituted or unsubstituted C3-C30 heteroaryl groups (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.). Further, in one embodiment, it is selected from any one of substituted or unsubstituted C6-C20 aryl groups or substituted or unsubstituted C3-C20 heteroaryl groups. Further, in one embodiment, it is selected from any one of substituted or unsubstituted groups: phenyl, naphthyl, biphenyl, terphenyl, pyridyl.

[0075] In one embodiment, R1 is not connected to adjacent ring structures or is connected to them by chemical bonds to form a benzene ring.

[0076] In one embodiment, the substituents in R1 are each independently selected from at least one of deuterium, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, and C3-C20 heteroaryl, and may further be at least one of deuterium and C1-C6 straight-chain or branched alkyl.

[0077] In one embodiment, R2 is selected from any one of deuterium, substituted or unsubstituted C1-C10 straight-chain or branched alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl. It can also be any one of deuterium, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl. Furthermore, it can be any one of deuterium and substituted or unsubstituted groups such as phenyl, naphthyl, biphenyl, terphenyl, and pyridyl.

[0078] In one embodiment, R2 is not connected to the adjacent ring structure or is connected to the benzene ring by chemical bonds;

[0079] In one embodiment, the substituents in R2 are each independently selected from deuterium, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy groups, and C6-C20 (e.g., C6... It may be at least one of the following: aryl (C9, C10, C12, C13, C14, C15, C16 or C18, etc.), heteroaryl (C3-C20, such as C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.), and may further be at least one of deuterium, C1-C6 straight-chain or branched alkyl, and may also be deuterium, methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl or tert-pentyl.

[0080] In one preferred embodiment, R3, R4, and R5 are each independently selected from deuterium, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, substituted or unsubstituted C3-C10 (e.g., C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, and substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, etc.). Any of the following groups: C16 or C18 aryl, substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16 or C18, etc.) heteroaryl, or deuterium, substituted or unsubstituted C6-C20 aryl. Further, in one embodiment, it is selected from any of the following groups: deuterium, substituted or unsubstituted: phenyl, naphthyl, biphenyl, terphenyl.

[0081] It should be noted that the organic compounds described in this disclosure may optionally be substituted with deuterium; the number of deuterium substituted organic compounds is denoted as n, where the total number of hydrogen atoms in the organic compound (the total number of hydrogen atoms before deuteration) is 100%. D Then n D It can range from 0% to 100%, for example, it can be 0, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 100%, etc.

[0082] The number of deuterium (n) D A value of 0 indicates that the organic compound has not been substituted with deuterium, and the number of deuterium (n) D The value of 100% indicates that all hydrogen atoms in the organic compound are replaced by deuterium.

[0083] In one implementation, n D =0, or 5%≤n D ≤100%, and further, it can be 10%≤n D ≤100%, or 20%≤n D ≤90%.

[0084] In one embodiment, the organic compound is selected from any one of the following compounds:

[0085] It should be noted that in the aforementioned compound P2-57, the "d15" outside the square brackets indicates that 15 hydrogen atoms in the compound are replaced by deuterium.

[0086] In a second aspect, this disclosure provides an application of an organic compound as described in the first aspect, wherein the organic compound is used in an organic electronic device.

[0087] In one embodiment, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin-film transistor, an organic field-effect transistor, an organic thin-film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper.

[0088] In one embodiment, the organic compound is applied to an organic electroluminescent device, and may further be applied to a red-light organic electroluminescent device.

[0089] In one embodiment, the organic compound serves as a light-emitting layer material in an organic electroluminescent device, and may further serve as a host material for the light-emitting layer, or as a host material for a red light-emitting layer.

[0090] Thirdly, this disclosure provides an organic electroluminescent material, the organic electroluminescent material comprising a combination of a first host material and a second host material; the first host material comprising an organic compound as described in the first aspect, and the second host material being a triazine compound.

[0091] In this disclosure, the organic compound with the structure shown in Formula I serves as the first host material, possessing excellent hole transport and injection performance. It is a hole-type host material with easy injection and high mobility. When combined with the second host material (electronic host) containing a triazine structure, it can effectively regulate and achieve a balance between hole and electron transport, thereby improving the efficiency and lifetime of the device and enhancing its overall performance.

[0092] In one embodiment, the triazine compound has the structure shown in Formula II:

[0093] In Formula IV, Ar3, Ar4, and Ar5 are each independently selected from any one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl groups; the substituents in Ar3, Ar4, and Ar5 are each independently selected from any one or a combination of at least two of the following: deuterium, halogen, C1-C20 straight-chain or branched alkyl, C2-C10 alkenyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0094] In one embodiment, the mass ratio of the first main material to the second main material is (0.1-2):1, for example, it can be 0.2:1, 0.3:1, 0.4:1, 0.5:1, 0.6:1, 0.7:1, 0.8:1, 0.9:1, 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1, 1.5:1, 1.6:1, 1.7:1, 1.8:1 or 1.9:1, and further, it can be (0.5-1.5):1.

[0095] Fourthly, this disclosure provides an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer comprising at least one of the organic compounds as described in the first aspect and the organic electroluminescent materials as described in the third aspect.

[0096] In one embodiment, the organic layer includes a light-emitting layer, which includes at least one of the organic compounds as described in the first aspect and the organic electroluminescent materials as described in the third aspect.

[0097] In one embodiment, the light-emitting layer includes a host material and a dopant material, wherein the host material includes at least one of the organic compounds described in the first aspect and the organic electroluminescent materials described in the third aspect.

[0098] In one embodiment, the organic layer includes a light-emitting layer, which includes at least one of the organic compounds as described in the first aspect and the organic electroluminescent materials as described in the third aspect.

[0099] In one embodiment, the light-emitting layer includes a host material and a dopant material, wherein the host material includes at least one of the organic compounds described in the first aspect and the organic electroluminescent materials described in the third aspect.

[0100] In one embodiment, the dopant material (also known as "dye", "guest material", "dopant") is a phosphorescent dopant material, and may further be a red phosphorescent dopant material.

[0101] In one embodiment, with the mass of the host material being 100%, the mass of the dopant material is 0.1-10%, for example, it can be 0.2%, 0.5%, 0.8%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, or 9%, etc.

[0102] In one embodiment, the mass of the doped material is 1-10% based on 100% of the organic electroluminescent material, for example, it can be 1.5%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, or 9%.

[0103] In one embodiment, the organic layer further includes a hole transport region and an electron transport region.

[0104] In one embodiment, the electron transport region includes any one or a combination of at least two of the electron injection layer, electron transport layer, and hole blocking layer.

[0105] In one embodiment, the electron transport region includes any one or a combination of at least two of the electron injection layer, electron transport layer, and hole blocking layer.

[0106] In one embodiment, the organic electroluminescent device (OLED device) includes a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer can be further divided into multiple regions, such as a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer comprises at least one of the organic compounds and organic electroluminescent materials disclosed herein.

[0107] In one embodiment, the organic electroluminescent device includes a first electrode, a plurality of light-emitting functional layers (organic layers), and a second electrode arranged sequentially. The organic layers include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer arranged sequentially, with the hole injection layer in contact with the first electrode (anode). The organic layer (which may also be a light-emitting layer) comprises at least one of the organic compounds and organic electroluminescent materials provided in this disclosure.

[0108] In one embodiment, 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 a display.

[0109] In one embodiment, the first electrode can be formed by sputtering or depositing a material used as the first electrode on a substrate. When the first electrode is used as an 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 a 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.

[0110] Organic layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used as organic layers can be small organic molecules, large organic molecules, or polymers, as well as combinations thereof.

[0111] 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.

[0112] The material for the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0113] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can be one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1 to HI-3 described below; it can also be one or more compounds of HT-1 to HT-51 doped with one or more compounds of HI-1 to HI-3 described below.

[0114] The light-emitting layer includes a host material (the organic compound and / or organic electroluminescent material provided in this disclosure) and light-emitting dyes (i.e., dopants) capable of emitting different wavelength spectra. The light-emitting layer can also be a monochromatic light-emitting layer emitting a single color such as red, green, or blue. Multiple monochromatic light-emitting 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 light-emitting layer. When different colored light-emitting layers are stacked together, they can be separated from each other or connected to each other. The light-emitting layer can also be a single colored light-emitting layer capable of simultaneously emitting different colors such as red, green, and blue.

[0115] 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.

[0116] In one aspect of this disclosure, the light-emitting layer employs phosphorescent electroluminescence technology. The host material of the light-emitting layer includes the organic electroluminescent material provided in this disclosure, namely, a combination of a first host material and a second host material, wherein the first host material includes at least one organic compound with a structure shown in Formula I.

[0117] In one embodiment, the second host material is a triazine compound having the structure shown in Formula IV; specifically, the triazine compound may be selected from, but not limited to, one or more combinations of the following specific compounds H1-H24.

[0118] In one aspect of this disclosure, the light-emitting layer employs phosphorescent photoluminescence technology. The phosphorescent doping material of the light-emitting layer may be selected from, but is not limited to, one or more combinations of RPD-1 to RPD-28 listed below.

[0119] In one aspect of this disclosure, an electron blocking layer (EBL) is located between the hole transport layer and the light-emitting layer. The electron blocking layer may be one or more compounds of HT-1 to HT-51 described above.

[0120] The organic layer may further 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); wherein the HBL is located between the light-emitting layer and the ETL, and the EIL is located between the cathode and the ETL.

[0121] In one aspect of this disclosure, 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.

[0122] In one aspect of this disclosure, a hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer may employ one or more compounds of ET-1 to ET-73 described above.

[0123] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0124] Fifthly, this disclosure also provides a display device, the display device comprising the organic electroluminescent device as described in the fourth aspect.

[0125] In one embodiment, the display device includes a display screen or a display panel.

[0126] This disclosure also provides an electronic device, which includes the aforementioned display device.

[0127] Compared with the prior art, this disclosure has the following beneficial effects:

[0128] The organic compound disclosed herein has the structure shown in Formula I, comprising an aromatic amine structure with a dibenzofuran (DBF) group attached thereto. A specific group R1 with strong conjugation is introduced on the same side of the DBF and aromatic amine attachment. Simultaneously, a heteroaromatic group containing a phenanthrene structure is introduced into the aromatic amine structure, constructing a large conjugated system. Through structural design and interactions between groups, this disclosure endows the organic compound with excellent photoelectric properties and hole transport / injection performance. As a host material for the luminescent layer in organic electroluminescent devices, it exhibits excellent carrier transport performance, making energy transfer between host and guest components more efficient, improving exciton utilization, thereby effectively enhancing the device's luminous efficiency, significantly extending device lifetime, reducing voltage, and optimizing the overall luminous performance of the device. Detailed Implementation

[0129] The technical solutions of this disclosure will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of this disclosure and should not be construed as specific limitations thereof.

[0130] In one specific embodiment, the organic compound can be prepared via the following representative synthetic route:

[0131] Among them, X1, X2, Ar1, Ar2, L1, L2, L3, R1, R2, R3, R4, R5, a, b, c, d and e have the same definition as in Formula I; Hal1 and Hal2 are each independently selected from any one of the halogens, for example, they can be F, I, Br or Cl, or they can be Cl or Br.

[0132] In one specific embodiment, reactions I and II are carried out in the presence of a palladium catalyst. The order of reactions I and II can be adjusted according to the synthesis situation; that is, reaction I can be carried out first, followed by reaction II, or reaction II can be carried out first, followed by reaction I. Usually, reaction I is carried out first, followed by reaction II.

[0133] In one specific embodiment, reaction I is carried out in the presence of tris(dibenzylacetone)dipalladium(O)Pd2(dba)3, 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride IPr·HCl, and a basic substance (e.g., sodium tert-butoxide t-BuONa). Reaction II is carried out in the presence of Pd2(dba)3, tri-tert-butylphosphine tetrafluoroborate (t-Bu)3PBF4, and a basic substance (e.g., sodium tert-butoxide t-BuONa).

[0134] In one specific embodiment, the organic compound is deuterated to form a deuterated compound, which can be prepared from a deuterated raw material through the aforementioned reaction; or, the deuterated compound can be obtained by reacting an undeuterated organic compound with a deuterated reagent (e.g., per-deuterated benzene, benzene-D6).

[0135] The specific preparation methods of the organic compounds described in this disclosure will be detailed below using several synthetic examples, but the preparation methods of this disclosure are not limited to these synthetic examples.

[0136] It should be noted that obtaining the organic compounds is not limited to the synthetic methods and raw materials used in this disclosure. Those skilled in the art can also select other methods or routes to obtain the organic compounds proposed in this disclosure. Organic compounds of Formula I synthesized by those skilled in the art using other methods are also within the protection scope of this disclosure.

[0137] The compounds, solvents, and reagents used in the synthetic methods not mentioned in this disclosure are all commercially available raw material products that can be purchased or customized from the domestic chemical market, or can be prepared in-house using these raw material products according to known methods.

[0138] The intermediates and target products in the following specific embodiments of this disclosure were analyzed and detected using an Agilent HPLC-6500 series Q-TOF liquid chromatography-mass spectrometry system to determine their molecular weights. An atmospheric pressure chemical ionization (APCI) source was used, and the ionization method was [M+H]. + .

[0139] Synthesis Example 1: Synthesis of Organic Compound P1-1

[0140] (1) Synthesis of M1

[0141] In a 1000 mL single-necked flask, 24 g of SM1, 17.9 g of SM2, 0.5 g of catalyst Pd2(dba)3, 0.4 g of 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride IPr·HCl, 21.3 g of sodium tert-butoxide, and 400 mL of toluene were added. The mixture was evacuated under vacuum and purged with nitrogen three times. The reaction was heated to 90 °C and reacted for 5 h. After the reaction was complete, it was stopped. The mixture was cooled to room temperature, and the reaction solution was separated. The organic phase was filtered twice through silica gel column chromatography. The concentrated organic phase was then added to methanol and refluxed for 1 h. The mixture was filtered to obtain a pale yellow powder M1, which was then recrystallized from ethyl acetate to obtain 26.4 g of pure product.

[0142] Theoretical m / z value: 538.20; Measured m / z value: 539.39 (APCI source, [M+H]) + ).

[0143] (2) Synthesis of P1-1

[0144] In a 1000 mL single-necked flask, add 26.4 g of M1, 15.0 g of SM3, 0.5 g of Pd2(dba)3, 0.4 g of tri-tert-butylphosphine tetrafluoroborate (t-Bu)3PBF4, 12.4 g of sodium tert-butoxide, and 400 mL of toluene. Vacuum the mixture and replace with nitrogen three times. Heat the mixture to 110 °C and react for 5 h. After the reaction is complete, stop the reaction. Cool to room temperature, separate the reaction mixture, filter the organic phase twice through silica gel column chromatography, concentrate the organic phase, add methanol, reflux and stir for 1 h, filter to obtain a pale yellow powder P1-1, and recrystallize three times from ethyl acetate to obtain 17.6 g of pure product.

[0145] Theoretical m / z value: 780.28; Measured m / z value: 781.36 (APCI source, [M+H]) + ).

[0146] The process routes for synthesis examples 2-20 are the same as those for synthesis example 1, except that the raw materials used are different. The raw materials, target products and result characterization data are shown in Table 1.

[0147] Table 1

[0148] This disclosure provides exemplary methods for synthesizing the above-mentioned compounds. Other organic compounds for which no specific synthesis method is provided can also be prepared by similar methods, requiring only the replacement of raw materials. These methods will not be elaborated here. Alternatively, those skilled in the art can prepare them using other methods in the prior art.

[0149] Example 1-1

[0150] 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:

[0151] (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.

[0152] (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. -5Pa, a mixture of compound HT-29:HI-1 (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.

[0153] (3) The compound HT-29 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.

[0154] (4) The compound HT-37 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 60 nm.

[0155] (5) A light-emitting layer is vacuum-deposited on the electron blocking layer. The light-emitting layer includes a host material and a dopant material (dye, RPD-18). The mass ratio (w / w) of the host material and the dopant material is 100:3. The host material is a mixture of a first host material (organic compound P1-1 provided in this disclosure) and a second host material (compound H13) (the mass ratio of P1-1 and H13 is 1:1). The evaporation is carried out using a dual-source co-evaporation method. The evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 40 nm.

[0156] (6) The compound ET-17 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.

[0157] (7) A mixture of compound ET-66: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.

[0158] (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.

[0159] (9) A 150 nm thick layer of metallic Al is vacuum-deposited on the electron injection layer as a cathode at a deposition rate of 1 nm / s to obtain the organic electroluminescent device.

[0160] Examples 1-2 to 30, Comparative Examples 1 to 4

[0161] An organic electroluminescent device differs from device example 1 only in that the main materials of the light-emitting layer are the compounds shown in Table 2, and the mass ratio of the first main material to the second main material is 1:1; other layers, thicknesses, materials, and preparation methods are the same as those in device example 1.

[0162] The structures of the main materials in Comparative Examples 1 to 4 are as follows:

[0163] The performance of the above-mentioned organic electroluminescent devices was tested using the following methods:

[0164] (1) Under the same brightness, the driving voltage and current efficiency of the organic electroluminescent device were measured using a digital source meter and a luminance meter; specifically, the voltage was increased at a rate of 0.1V per second, and the efficiency was measured when the brightness of the organic electroluminescent device reached 10mA / cm². 2 The voltage at that time is the operating voltage. At the same time, the brightness at that time is measured. The ratio of brightness to current density is the current efficiency.

[0165] (2) The LT97 lifetime was tested as follows: at a constant current density of 60 mA / cm² 2 The time taken for the brightness to decay during testing, such as LT97 lifetime, refers to the time it takes for the brightness to decay to 97% of the initial brightness, in hours.

[0166] With the test values ​​of each performance indicator of Comparative Example 1 recorded as 100%, the ratios of the test values ​​of the performance indicators of other devices to the test values ​​of Comparative Example 1 were calculated; the test results are shown in Table 2:

[0167] Table 2

[0168] As shown in Table 2, the organic compounds provided in this disclosure possess excellent hole transport performance and photoelectric properties. As the main material for the light-emitting layer of organic electroluminescent devices, they can effectively improve the luminous efficiency of the device, significantly extend its lifetime, and reduce voltage. Specifically, comparing compounds P1-4 of this disclosure with Comparative Example 1, it can be seen that the dibenzofuranyl (DBF) group in Comparative Example 1 is unsubstituted, while compounds P1-4 of this disclosure have a substituent R1 inside the DBF group, significantly enhancing its transport performance and increasing its energy transfer efficiency. Comparing compounds P1-17 of this disclosure with Comparative Example 2, it can be seen that the effect of the benzene ring being connected inside the DBF is significant; compared to the connection outside the DBF, the lifetime is greatly improved. Comparing Example 18 with Comparative Example 3, it can be seen that the structure designed in this disclosure, and the molecular configuration of connecting the benzene ring at the meta position inside the DBF, is more conducive to charge injection and energy transport, resulting in a significant improvement in device performance. Combining the compounds P5-6 disclosed herein with Comparative Example 4, it can be seen that devices containing the substituent DBF on the aromatic amine N exhibit better performance than devices containing dibenzothiophene DBS.

[0169] Based on the above-mentioned device mechanism research, this disclosure presents quantitative calculations for compounds A, B, and C with similar structures. The calculations were performed using Gaussian 16 software at the B3LYP / 6-31G* level, with the SMD model describing the solvation effect, and toluene as the solvent. The data are shown in Table 3 below.

[0170] Table 3

[0171] As can be seen from the above data, compound A is an organic compound provided in this disclosure, which has a higher intrinsic dipole moment. This difference leads to the material of this disclosure exhibiting better performance in molecular stacking and film formation as well as host-guest energy transfer, resulting in improved efficiency.

[0172] The applicant declares that this disclosure illustrates the organic compounds and their applications, as well as organic electroluminescent devices, through the above embodiments. However, this disclosure is not limited to the above embodiments, meaning that this disclosure does not necessarily rely on the above embodiments for implementation. Those skilled in the art should understand that any improvements to this disclosure, equivalent substitutions of raw materials for the products of this disclosure, additions of auxiliary components, and selection of specific methods all fall within the protection and disclosure scope of this disclosure.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in Formula I: Among them, X1 and X2 are each independently selected from N, O or S, and one and only one of them is N; Ar1 and Ar2 are each independently selected from any one of substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; L1, L2, and L3 are each independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C3-C30 heteroarylene. R1 is selected from any one of the following: substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino. R2, R3, R4, and R5 are each independently selected from any one of deuterium, halogen, cyano, substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamino, and substituted or unsubstituted C3-C30 heteroarylamino. R1 and R2 are each independently unconnected to the adjacent ring structure or connected to form a ring by chemical bonds; a is an integer selected from 1 to 3; b and c are each independently selected from 0 to 4; d and e are each independently selected from 0 to 2; 0 ≤ c + d + e ≤ 7. The substituents in Ar1, Ar2, L1, L2, L3, R1, R2, R3, R4, and R5 are each independently selected from at least one of deuterium, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 heterocycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; each substituent is independently not connected to the adjacent ring structure or is connected to form a ring by a chemical bond; Hydrogen at any site on the organic compound with the structure shown in Formula I may optionally be replaced by deuterium.

2. The organic compound according to claim 1, characterized in that, The organic compound has the structure shown in Formula II: Where X1 is O or S; Ar1, Ar2, L1, L2, L3, R1, R2, R3, R4, R5, a, b, c, d and e have the same range of limitation as in Equation I.

3. The organic compound according to claim 1, characterized in that, The organic compound has a structure as shown in any one of Formula III-1 to III-12: Where X1 is O or S; Ar1, Ar2, L1, L2, R1, R2, R3, R4, R5, b, c, d, and e have the same range of limitation as in Equation I; In one embodiment, the organic compound has a structure as shown in any one of Formula III-1, Formula III-2, Formula III-3, or Formula III-4.

4. The organic compound according to any one of claims 1-3, characterized in that, Ar1 and Ar2 are each independently selected from any one of substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C5-C20 heteroaryl; In one embodiment, Ar1 and Ar2 are each independently selected from any one of the following groups, either substituted or unsubstituted: Wherein, —* represents the linking site of the group; Y1 is selected from O, S, NR 11 or CR 12 R 13 Any one of them; R A R 11 R 12 R 13 Each is independently selected from any one or a combination of at least two of the following: C1-C20 straight-chain or branched alkyl, C6-C30 aryl, C3-C30 heteroaryl, and C2-C20 alkenyl; The R 12 and R 13 They are either not connected or linked by chemical bonds to form a ring; In one implementation, the R A R 11 R 12 R 13 Each is independently selected from any one or a combination of at least two of the following: C1-C10 straight-chain or branched alkyl, C2-C10 alkenyl, and C6-C20 aryl; In one embodiment, the substituents in Ar1 and Ar2 are each independently selected from any one or a combination of at least two of deuterium, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C6-C20 aryl, and C3-C20 heteroaryl; and each substituent is independently not connected to the adjacent ring structure or is connected to the ring structure by a chemical bond to form a ring.

5. The organic compound according to any one of claims 1-3, characterized in that, Ar1 and Ar2 are each independently selected from any one of the following unsubstituted or deuterated groups: In this context, —* represents the linking site of a functional group.

6. The organic compound according to any one of claims 1-3, characterized in that, L1 and L2 are each independently selected from any one of single bond, substituted or unsubstituted C6-C20 arylene, or substituted or unsubstituted C5-C20 heteroarylene; In one embodiment, L1 and L2 are each independently selected from any one of the following groups: single bond, substituted or unsubstituted: In this context, —* represents the linking site of a functional group.

7. The organic compound according to any one of claims 1-3, characterized in that, R1 is selected from any one of substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C1-C10 alkoxy groups, substituted or unsubstituted C2-C10 alkenyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaryl groups. It can also be any one of substituted or unsubstituted C6-C20 aryl groups and substituted or unsubstituted C3-C20 heteroaryl groups. Furthermore, it can be any one of substituted or unsubstituted groups of the following: phenyl, naphthyl, biphenyl, terphenyl, and pyridyl. In one embodiment, R1 is not connected to adjacent ring structures or is connected to a benzene ring by chemical bonds; In one embodiment, the substituents in R1 are each independently selected from at least one of deuterium, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, and C3-C20 heteroaryl, and may further be at least one of deuterium and C1-C6 straight-chain or branched alkyl.

8. The organic compound according to any one of claims 1-3, characterized in that, The R2 is selected from any one of deuterium, substituted or unsubstituted C1-C10 straight-chain or branched alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl. It can also be any one of deuterium, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C3-C20 heteroaryl. Furthermore, it can be any one of deuterium and substituted or unsubstituted groups of the following: phenyl, naphthyl, biphenyl, terphenyl, and pyridyl. In one embodiment, R2 is not connected to the adjacent ring structure or is connected to the benzene ring by chemical bonds; In one embodiment, the substituents in R2 are each independently selected from at least one of deuterium, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, and C3-C20 heteroaryl, and may further be at least one of deuterium and C1-C6 straight-chain or branched alkyl.

9. The organic compound according to any one of claims 1-3, characterized in that, R3, R4, and R5 are each independently selected from any one of deuterium, substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C20 aryl groups, and substituted or unsubstituted C3-C20 heteroaryl groups. They can also be any one of deuterium, substituted or unsubstituted C6-C20 aryl groups, and further can be any one of deuterium, substituted or unsubstituted groups of the following: phenyl, naphthyl, biphenyl, and terphenyl.

10. The organic compound according to claim 1, characterized in that, The organic compound may optionally be substituted with deuterium; the number of deuterium is denoted as n, with the total number of hydrogen atoms in the organic compound being 100%. D n D =0, or 5%≤n D ≤100%, or 10%≤n D ≤100%, and further, it can be 20%≤n D ≤90%.

11. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the following compounds:

12. An application of an organic compound as described in any one of claims 1-11, characterized in that, The organic compounds are used in organic electronic devices; In one embodiment, the organic compound is applied to an organic electroluminescent device; In one embodiment, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.

13. An organic electroluminescent material, characterized in that, The organic electroluminescent material comprises a combination of a first host material and a second host material; the first host material comprises an organic compound as described in any one of claims 1-11, and the second host material is a triazine compound; In one embodiment, the mass ratio of the first main material to the second main material is (0.1-2):1, or it can be (0.5-1.5):

1.

14. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes at least one of the organic compounds as described in any one of claims 1-11 and the organic electroluminescent material as described in claim 13; In one embodiment, the organic layer includes a light-emitting layer, the light-emitting layer comprising at least one of the organic compounds as described in any one of claims 1-11 and the organic electroluminescent material as described in claim 13; In one embodiment, the light-emitting layer includes a host material and a dopant material, wherein the host material includes at least one of the organic compounds as described in any one of claims 1-11 and the organic electroluminescent material as described in claim 13.

15. A display device, characterized in that, The display device includes the organic electroluminescent device as described in claim 14.

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