Organic compound, electroluminescent material and use thereof
Patent Information
- Application Number
- CN202611382967.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2026-09-08
- Publication Date
- 2026-10-13
AI Technical Summary
目前的OLED材料难以兼顾高效率、长寿命以及低驱动电压多重性能需求,设计一种可以使器件兼具高效率、长寿命和低驱动电压的有机化合物是刻不容缓的
[0266]本申请提供的有机化合物可以作为OLED器件的发光主体材料,能有效降低器件的驱动电压,并且其优异的空穴迁移能力可以促进载流子传输平衡,抑制激子淬灭并提高激子利用率,从而显著提升器件的发光效率与寿命;同时,所述有机化合物具有卓越的热稳定性,有效避免了蒸镀工艺过程中的热分解风险,确保了薄膜形态的稳定性,防止器件性能劣化,进一步延长了器件的使用寿命。
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Figure CN122897769A_ABST
Abstract
Description
Technical Field
[0001] This application belongs to the field of organic electroluminescent materials technology, specifically relating to an organic compound, an electroluminescent material, and its applications. Background Technology
[0002] In recent years, optoelectronic devices based on organic materials have become increasingly popular. Their development is closely related to technological breakthroughs in transparent conductive thin-film materials and thick-film materials specifically for electronic components, while also providing new development directions for the semiconductor light-emitting diode (LED) and integrated circuit manufacturing fields. The inherent flexibility of organic materials makes them ideal for manufacturing 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 (FETs), organic photovoltaic cells, and organic sensors. OLEDs, in particular, have developed rapidly, achieving commercial success in the information display field. Their production process also widely utilizes transparent conductive thin-film materials and thick-film materials specifically for electronic components, supporting improvements in device performance. OLEDs can provide highly saturated red, green, and blue colors. Full-color displays made with OLEDs do not require an additional backlight, offering advantages such as vibrant colors, thinness, and flexibility. They complement semiconductor light-emitting diodes, jointly driving the diversified development of the optoelectronic display field.
[0003] The core of OLED devices lies in their thin-film structures containing various organic functional materials. Their fabrication process requires combining specialized thick-film and thin-film materials for electronic components with transparent conductive thin-film materials to ensure both conductivity and light transmittance. 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 luminescent host materials and luminescent guest materials (dyes). When an electric current is applied, electrons and holes are injected and transported to the luminescent region, where they recombine to generate excitons and emit light. The stability of this process provides a foundation for the integrated application of related devices in integrated circuit manufacturing.
[0004] Various organic materials have been developed and, combined with device structure design, can improve carrier mobility, regulate carrier balance, enhance electroluminescence efficiency, and delay device decay. The optimization of these materials has also driven the upgrading of transparent conductive thin-film materials and thick-film materials specifically for electronic components, further adapting to the needs of semiconductor light-emitting diodes and integrated circuit manufacturing. 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 complexes, can simultaneously utilize 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) 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 (TSF) technology uses materials with TADF properties to sensitize the emitter through energy transfer, also achieving high luminescence efficiency. Furthermore, scientists have proposed a strategy for phosphorescently assisted thermally activated sensitized fluorescence (pTSF), which involves transferring the excited-state energy of phosphorescent materials to fluorescent materials for luminescence. This achieves theoretically 100% exciton utilization while simultaneously realizing high luminous efficiency, long lifetime, and high color purity. This technological breakthrough also provides new insights for improving the performance of semiconductor light-emitting diodes and for miniaturizing and increasing the efficiency of integrated circuit manufacturing.
[0005] In the prior art, some progress has been made in organic electroluminescent materials based on polycyclic aromatic hydrocarbon derivatives. CN114181095A discloses an aromatic amine compound with benzo[c]phenanthrene as the parent nucleus. This technical solution limits the amino substitution site to the 1-position of benzo[c]phenanthrene. This type of compound increases the rigidity of triarylamines, has a high triplet energy level, and improves the thermal stability and carrier transport capacity of the material. When used as a hole transport material and electron blocking material in organic electroluminescent devices, it can reduce the driving voltage of the device and improve the luminous efficiency and lifetime of the device.
[0006] CN116239479A discloses an aromatic amine compound with benzo[g]ch as the parent nucleus. This type of compound has a rigid benzo[g]ch structure with large planar conjugation, and has the characteristics of high carrier mobility, high internal quantum efficiency, stable thin film state and excellent heat resistance. When used as a hole transport material, it can improve the efficiency, lifetime and voltage of the device.
[0007] CN119173497A discloses an aromatic amine compound with benzo[g]ch as the parent nucleus, which can improve the voltage, efficiency and lifetime of the device when used in the blue light hole auxiliary layer.
[0008] While the aforementioned aromatic amine compounds can improve the luminescence performance of devices to some extent, the accelerated commercialization of organic light-emitting diodes (OLEDs) has led to more stringent requirements for the overall performance of OLED devices. Current OLED materials struggle to simultaneously meet the multiple performance demands of high efficiency, long lifespan, and low driving voltage. Therefore, designing an organic compound that can achieve these three combined properties is urgently needed. Summary of the Invention
[0009] To address the shortcomings of existing technologies, the purpose of this application is to provide an organic compound, an electroluminescent material, and their applications. By designing the structure of the organic compound, it can achieve excellent charge transport capabilities. When applied to organic electroluminescent devices, it can improve the luminous efficiency of the device, reduce the driving voltage of the device, and extend the lifespan of the device.
[0010] To achieve this objective, the following technical solution is adopted in this application:
[0011] In a first aspect, this application provides an organic compound having the structure shown in Formula I:
[0012] Formula I.
[0013] Among them, L1, L2, and L3 are each independently selected from any one of single bond, substituted or unsubstituted C6-C60 arylene, or substituted or unsubstituted C3-C60 heteroarylene; when L1 is a single bond, it means that the structures at both ends (Ar1 and N atoms) are directly connected by a single bond; the same applies when L2 and L3 are single bonds. For the sake of simplicity, it will not be elaborated further.
[0014] R1, R2, R3, and R4 are each independently selected from any one of the following: deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, C1-C20 ester, substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino.
[0015] At least two adjacent groups in R1, R2, R3, and R4 are either not connected or are linked by chemical bonds to form a ring.
[0016] It should be noted that, in this application, any adjacent group among R1, R2, R3, and R4 can refer to two adjacent groups on the same benzene ring, such as two adjacent R2 or two adjacent R3, that is, two adjacent R2 can be connected to form a ring by chemical bonds, and two adjacent R3 can be connected to form a ring by chemical bonds; any adjacent group among R1, R2, R3, and R4 can also refer to adjacent groups located on different benzene rings, such as adjacent R1 and R2 or adjacent R2 and R3, that is, adjacent R2 and R3 can be connected to form a ring by chemical bonds, and adjacent R1 and R2 can be connected to form a ring by chemical bonds.
[0017] Ar2 is selected from any one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino.
[0018] Ar1 is selected from any one of the following groups:
[0019] .
[0020] The linking site of the representative group.
[0021] The substituents described in L1, L2, L3, R1, R2, R3, R4, and Ar2 are each independently selected from deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, C1-C20 ester group, unsubstituted or R'-substituted C1-C30 straight-chain or branched alkyl group, unsubstituted or R'-substituted C2-C20 alkenyl group, unsubstituted or R'-substituted C1-C30 alkoxy group, unsubstituted or R'-substituted C3-C30 cycloalkyl group, unsubstituted or R'-substituted C3-C30 heterocyclic alkyl group, unsubstituted or R'-substituted C1-C20 alkylsilyl group, unsubstituted or R'-substituted C3-C30 alkylsilyl group, and unsubstituted or R'-substituted C3-C30 alkylsilyl group. At least one of the following: substituted C6-C60 aryloxy, unsubstituted or R'-substituted C6-C60 arylamino, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; the substituents described in L1, L2, L3, R1, R2, R3, R4, and Ar2 are each independently not connected to adjacent ring structures or are connected to form a ring by chemical bonds; at least two adjacent groups among the substituents described in L1, L2, L3, R1, R2, R3, R4, and Ar2 are not connected to each other or are connected to form a ring by chemical bonds.
[0022] In this application, the term "substituted or unsubstituted" can refer to the substitution of one or more substituents. When there are multiple substituents (at least two), they can be the same or different substituents. The same expression used below has the same meaning. Unless otherwise specified, the selection range of substituents in L1, L2, L3, R1, R2, R3, R4, and Ar2 is as shown above and will not be repeated.
[0023] Each R' is independently selected from at least one of deuterium, halogen, cyano, C1-C30 straight-chain or branched alkyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C3-C30 heterocyclic alkyl, C6-C60 aryl, and C3-C60 heteroaryl; at least two adjacent R's are not connected to each other or are linked to each other by chemical bonds to form a ring; each R' is independently not connected to the adjacent ring structure or is linked to each other by chemical bonds to form a ring.
[0024] In this application, the "unsubstituted or R'-substituted" group can be substituted with one substituent R' or multiple substituents R'. When there are multiple substituents R' (at least two), they can be the same or different substituents; the same expression used below has the same meaning. Unless otherwise specified, the selection range of R' is as shown above and will not be repeated.
[0025] a and d are each independently selected from integers between 0 and 4, for example, they can be 0, 1, 2, 3 or 4.
[0026] b and c are each independently selected from integers between 0 and 2, for example, they can be 0, 1 or 2.
[0027] When there are multiple (at least 2) R1s, the multiple R1s can be the same or different; when there are 2 R2s, the 2 R2s can be the same or different; when there are 2 R3s, the 2 R3s can be the same or different; when there are multiple (at least 2) R4s, the multiple R4s can be the same or different.
[0028] In organic compounds with the structure shown in Formula I, any hydrogen may be optionally substituted with deuterium.
[0029] In Formula I, Includes any of the following structures:
[0030] ; The linking site of the representative group.
[0031] The organic compound provided by the present application is a triarylamine-based organic compound constructed from a bis-large conjugated skeleton and an Ar2 group. By expanding the delocalization range of π electrons, the hole mobility of the material is significantly improved, thereby optimizing the hole injection and transport performance. In terms of molecular configuration, the introduced benzo[g]chrysene or benzo[c]phenanthrene unit has a large π-conjugated system, but its inherent helical three-dimensional configuration induces moderate distortion of the molecular plane. This non-planar structure effectively inhibits excessive close packing between molecules, thereby alleviating problems such as charge transport imbalance, luminescence quenching, and efficiency roll-off caused by aggregation. In addition, the introduction of the Ar2 group can finely regulate the spatial configuration and charge transport characteristics of the molecule, optimize the energy level arrangement, and enhance the carrier transition, injection and transport capabilities.
[0032] It should be noted that in the present application, for the convenience of description, the possible functions of each group / feature of the organic compound are described respectively, but this does not mean that these groups / features act in isolation. In fact, the reason for obtaining good performance is essentially the optimized design of the entire molecular structure, which is the result of the synergistic effect between various groups, rather than the effect of a single group.
[0033] In the present application, the hydrogen atoms in the organic compound having the structure represented by Formula I may be replaced by its isotope deuterium atoms, so as to form a deuterated compound. The deuteration content (T%) may be 0-100%, preferably 10-90%, more preferably 20-80%, particularly preferably 30-70%, and most preferably 40-60%; 0% means that the hydrogen atoms in the organic compound are not replaced by deuterium atoms.
[0034] In the present application, when the number of hydrogen atoms in the organic compound is T1, and the number of deuterium atoms substituted after deuterium substitution is T2, the deuteration content T% of the organic compound after deuteration can be defined as T%=T2 / T1×100%; for example, the number of hydrogen atoms contained in a benzene substituent is 5 (T1), and the number of deuterium atoms after deuterium substitution is 1 (T2), then the deuteration content of the phenyl group is 20%. The phenyl structure with 20% deuteration content can be represented by the following structural formula:
[0035]
[0036] In the present application, when the hydrogen atoms in the organic compound having the structure represented by Formula I are not all replaced by deuterium atoms, that is, when the deuteration content is less than 100%, the number of deuterium atoms in the structure can be expressed as Dn, where n represents the number of deuterium atoms.
[0037] In the present application, for the expression of chemical elements, unless otherwise specified, it includes the concept of isotopes with the same chemical properties. For example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3H (tritium, T), etc.; carbon (C) includes 12 C 13 C, etc.
[0038] In this application, unless otherwise specified, the heteroatoms in the heteroaryl group are selected from N, O, S, P, Si or Se, preferably N, O or S; the heteroatoms in the heterocycloalkyl group are selected from N, O, S, P, Si or Se, preferably N, O or S.
[0039] Examples of halogens in this application include fluorine, chlorine, bromine, iodine, etc.
[0040] In this application, the way the ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.
[0041] In this application, " " "" all indicate the linking site of the group.
[0042] In this application, 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.
[0043] In this application, "each independently" means that when there are multiple subjects, they may be the same or different from each other.
[0044] In this application, 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.
[0045] 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.
[0046] C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.
[0047] C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.
[0048] C2-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.
[0049] 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.
[0050] C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.
[0051] C2-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.
[0052] In this application, the C6-C60 aryl group, preferably C6-C30 aryl group, includes monocyclic aryl and fused-ring aryl groups. A monocyclic aryl group refers to a group containing at least one phenyl atom. When it contains at least two phenyl atomes, the phenyl atomes are linked by a single bond. Examples include, but are not limited to, phenyl, biphenyl, terphenyl, tetraphenyl, etc. A 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 (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). Aryl groups include 9,9-dibutylfluorenel, 9,9-dipentylfluorenel, 9,9-dihexylfluorenel, 9,9-diphenylfluorenel, 9,9-dinaphthylfluorenel, phenylmethylfluorenel, spirodifluorenel, benzo[a]fluorenel, etc.), fluoranyl, triphenylene, pyrene (1-pyrene, 2-pyrene, 4-pyrene), peryl, phenyl, and tetraphenyl (1-tetraphenyl, 2-tetraphenyl, 9-tetraphenyl), etc. It should be noted that monocyclic aryl groups and fused-ring aryl groups linked by single bonds also fall under the category of aryl groups, such as phenylnaphthyl, naphthylphenyl, and binaphthyl.
[0053] In this application, the C3-C60 heteroaryl group, preferably C3-C30 heteroaryl group, includes 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, including but not limited to: quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, isobenzofuranyl, isobenzothiopheneyl, indolyl, dibenzofuranyl, dibenzothiopheneyl, naphthobenzofuranyl, naphthobenzothiopheneyl, carbazoleyl and its derivatives (N-phenylcarbazoleyl, N-naphthylcarbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, indolocarbazoleyl, azacarbazoleyl, etc.), acridineyl, phenothiazinyl, phenotoxazinyl, 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, phenyldibenzothiophenyl, dibenzothiophenylphenyl, dibenzofuranylphenyl, etc.
[0054] Specific examples of the C6-C60 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-C60 heteroarylene group can be exemplified by removing one hydrogen atom from the heteroaryl group examples above, resulting in a divalent group.
[0055] The C6-C60 aryloxy group is a monovalent group formed by attaching the aforementioned aryl group to O; the C3-C60 heteroaryloxy group is a monovalent group formed by attaching the aforementioned heteroaryl group to O.
[0056] Specific examples of the C6-C60 arylamino group are monovalent groups obtained by substituting at least one hydrogen atom in -NH2 with the aforementioned aryl group, including but not limited to: phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, biphenylamino, etc.; specific examples of the C3-C60 heteroarylamino group are monovalent groups obtained by substituting at least one hydrogen atom in -NH2 with the aforementioned heteroaryl group, including but not limited to: pyridinylamino, pyrimidinylamino, dibenzofuranylamino, etc.
[0057] A specific example of the C6-C30 arylsilyl group is a monovalent group obtained by replacing at least one hydrogen in -SiH3 with the aforementioned aryl group.
[0058] The C1-C30 straight-chain or branched alkyl group, preferably C1-C20 straight-chain or branched alkyl group, more preferably C1-C10 straight-chain or branched alkyl group, includes, but is 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.
[0059] The C1-C30 alkoxy group, preferably C1-C20 alkoxy group, is a monovalent group obtained by connecting the above-mentioned straight-chain or branched alkyl groups to O.
[0060] The C3-C30 cycloalkyl group, preferably C3-C20 cycloalkyl group, more preferably C3-C10 cycloalkyl group, includes, but is not limited to: cyclopropyl, cyclobutyl, cyclopentyl, tert-amyl, cyclohexyl, adamantyl, etc.
[0061] The C3-C30 heterocyclic alkyl group, preferably C3-C20 heterocyclic alkyl group, more preferably C3-C10 heterocyclic alkyl group, is a group 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, oxocyclic butyl group, tetrahydrofuranyl group, tetrahydrothiophenyl group, tetrahydropyrryl group, tetrahydropyranyl group, piperidinyl group, piperazinyl group, dioxaneyl group, morpholinyl group, etc.
[0062] The C2-C30 alkenyl group, preferably C2-C20 alkenyl group, more preferably C2-C10 alkenyl group, contains at least one C=C group, and includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.
[0063] The C1-C30 alkylsilyl group, preferably C1-C20 alkylsilyl group, is a monovalent group obtained by substituting at least one hydrogen in -SiH3 with the above-mentioned straight-chain or branched alkyl group; exemplary, including but not limited to: tri(methyl)silyl, dimethylsilyl, di(methyl)ethylsilyl, di(methyl)propylsilyl, tri(ethyl)silyl, tri(propyl)silyl, etc.
[0064] The structure of the C1-C20 ester group is -C(=O)-OM; wherein M is selected from any one of hydrogen, C1-C19 straight-chain or branched alkyl groups.
[0065] In one specific embodiment, the organic compound has a structure as shown in any one of formula II-1, formula II-2, formula II-3, or formula II-4:
[0066] .
[0067] Among them, L1, L2, L3, Ar2, R1, R2, R3, R4, a, b, c, and d have the same limited range as in Equation I.
[0068] In one specific embodiment, the organic compound has a structure as shown in any one of formulas III-1 to III-22:
[0069] .
[0070] Among them, L1, L2, L3, Ar2, R1, R2, R3, R4, a, b, c, and d have the same limited range as in Equation I.
[0071] Ar1' is selected from any one of the following groups:
[0072] .
[0073] The linking site of the representative group.
[0074] a1 is selected from integers from 0 to 3, for example, it can be 0, 1, 2 or 3.
[0075] b1 is selected from 0 or 1.
[0076] In Forms III-12 to III-22 of this application, Includes any one of the following groups:
[0077] .
[0078] Preferably, Includes any one of the following groups:
[0079] .
[0080] Preferably, the Ar1' is selected from any one of the following groups:
[0081] .
[0082] Preferably, the organic compound has the structure shown in any one of Formula III-2, Formula III-3, Formula III-4, Formula III-7, Formula III-8, Formula III-11, Formula III-13, Formula III-19 or Formula III-22.
[0083] Preferably, L1, L2, and L3 are each independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) arylene, or substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroarylene.
[0084] Preferably, L1, L2, and L3 are each independently selected from any one of the following groups: single bond, substituted, or unsubstituted:
[0085] .
[0086] in, The linking site of the representative group.
[0087] Z1 is selected from O, S, and NAr. 11 CR 11 R 12 Any one of them.
[0088] Z2 is selected from N or CR 13 .
[0089] L' is selected from any one of C6-C30 arylene or C3-C30 heteroarylene.
[0090] Ar 11 It is selected from any one of unsubstituted or R'-substituted C6-C60 aryl groups and unsubstituted or R'-substituted C3-C60 heteroaryl groups.
[0091] R 11 R 12 R 13 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, C1-C20 ester, unsubstituted or R'-substituted C1-C30 straight-chain or branched alkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C3-C30 cycloalkyl, unsubstituted or R'-substituted C3-C30 heterocycloalkyl, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C60 aryloxy, unsubstituted or R'-substituted C6-C60 arylamino, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.
[0092] Preferably, L' is a phenylene oxide.
[0093] Preferably, the R 11 R 12 R 13 Each is independently selected from any one of hydrogen, deuterium, unsubstituted or R'-substituted C1-C10 straight-chain or branched alkyl, unsubstituted or R'-substituted C6-C30 aryl, and unsubstituted or R'-substituted C3-C30 heteroaryl; more preferably, each is selected from any one of hydrogen, deuterium, unsubstituted or R'-substituted C1-C3 straight-chain alkyl, and unsubstituted or R'-substituted C6-C20 aryl.
[0094] Preferably, L1, L2, and L3 are each independently selected from any one of the following groups: single bond, substituted, or unsubstituted:
[0095] .
[0096] in, The linking site of the representative group.
[0097] Preferably, the Ar2 is selected from substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl, substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryl, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryloxy, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryloxy, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryloxy, and substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C13, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryloxy. Any one of the following: arylamino groups (C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.); heteroaryloxy groups (C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) with substituted or unsubstituted arylamino groups (C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.); and heteroarylamino groups (C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.) with substituted or unsubstituted arylamino groups (C6-C30, etc.); preferably any one of the following: arylamino groups (C6-C30, etc.) with substituted or unsubstituted arylamino groups (C3-C30, etc.).
[0098] Preferably, the Ar2 is selected from any one of the following groups, whether substituted or unsubstituted:
[0099] .
[0100] in, The linking site of the representative group.
[0101] Z3 is selected from O, S, and CR. 21 R 22 SiR 23 R 24 ,NAr 21 Any one of them.
[0102] Z4 is selected from N or CR. 25 .
[0103] L'' is selected from any one of C6-C30 arylene or C3-C30 heteroarylene.
[0104] R 21 R 22 R 23 R 24 R 25 Each is independently selected from any one of hydrogen, deuterium, unsubstituted or R'-substituted C1-C30 straight-chain or branched alkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C3-C30 cycloalkyl, unsubstituted or R'-substituted C3-C30 heterocycloalkyl, unsubstituted or R'-substituted C6-C60 aryloxy, unsubstituted or R'-substituted C6-C60 arylamino, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R 21 With R 22 They are either not connected or linked by chemical bonds to form a ring, R 23 With R 24 They are either not connected to each other or are linked together by chemical bonds to form a ring.
[0105] Ar 21 It is selected from any one of unsubstituted or R'-substituted C6-C60 aryl groups and unsubstituted or R'-substituted C3-C60 heteroaryl groups.
[0106] Preferably, the R 21 R 22 R 23 R 24 R 25Each is independently selected from any one of the following: unsubstituted or R'-substituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9) straight-chain or branched alkyl groups; unsubstituted or R'-substituted C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9) cycloalkyl groups; unsubstituted or R'-substituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl groups; and unsubstituted or R'-substituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryl groups.
[0107] Preferably, the R 21 R 22 R 23 R 24 R 25 Each group is independently selected from any one of the following groups, either unsubstituted or R'-substituted: C1-C3 straight-chain alkyl, C3-C6 cycloalkyl, phenyl, naphthyl, biphenyl.
[0108] Preferably, the Ar 21 It is selected from any one of unsubstituted or R'-substituted C6-C30 aryl groups and unsubstituted or R'-substituted C3-C30 heteroaryl groups, and more preferably any one of unsubstituted or R'-substituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, etc.) aryl groups and unsubstituted or R'-substituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, etc.) heteroaryl groups.
[0109] Preferably, the Ar 21 Selected from any one of the following groups, either unsubstituted or R'-substituted: phenyl, naphthyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzo[a]fluorenyl, benzo[a]furanyl, benzo[a]thiopheneyl, dibenzo[a]furanyl, dibenzo[a]thiopheneyl, carbazoleyl, benzimidazolyl, benzo[a]indazolyl, benzo[a]carbazoleyl, benzo[a]furan ... The following groups are preferred: benzo[carbazole], benzo[thiophene]carbazole, benzo[furan]dibenzofuran, benzo[furan]dibenzothiophene, benzo[thiophene]dibenzothiophene, indol[carbazole], azadibenzothiophene, azadibenzofuran, and more preferably any one of the following groups that are unsubstituted or R'-substituted: phenyl, naphthyl, biphenyl, terphenyl, 9,9-dimethylfluorenyl, dibenzofuran, dibenzothiophene.
[0110] Preferably, Ar21 The R' mentioned herein is independently selected from deuterium, halogen, cyano, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl, C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy, C3-C10 (e.g., C3, C4, C5, C6, C8, C9, etc.) alkoxy, C3-C10 (e.g., C3, C4, C5, C6, C8, C9, etc.) alkyl, ... At least one of the following: heterocyclic alkyl groups (C7, C8, C9, etc.), aryl groups (C6-C20, e.g., C6, C9, C10, C12, C14, C15, C16, C18, C20, etc.), and heteroaryl groups (C3-C20, e.g., C3, C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, C20, etc.), and more preferably at least one of deuterium, C6-C15 aryl, and C3-C15 heteroaryl.
[0111] Preferably, the Ar2 is selected from any one of the following groups, whether substituted or unsubstituted:
[0112] .
[0113] in, The linking site of the representative group.
[0114] Preferably, R1, R2, R3, and R4 are each independently selected from deuterium, halogen, substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9) straight-chain or branched alkyl groups, substituted or unsubstituted C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9) alkenyl groups, and substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9) groups. Alkoxy, substituted or unsubstituted C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9) cycloalkyl, substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl, substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, etc.) Heteroaryl groups (C20, C22, C24, C26, or C28, etc.), substituted or unsubstituted C6-C30 groups (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryloxy groups, substituted or unsubstituted C6-C30 groups (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) arylamino groups, Any one of the following: substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryloxy groups; substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroarylamino groups.
[0115] Preferably, R1, R2, R3, and R4 are each independently selected from deuterium, substituted or unsubstituted groups from any of the following: C1-C3 straight-chain alkyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophene, and biphenyl.
[0116] Preferably, at least two adjacent groups among R1, R2, R3, and R4 are not connected or are linked by chemical bonds to form a ring Cy1. The ring Cy1 is selected from any one of substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) alicyclic rings, substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C15, C16, C18, etc.) aromatic rings, and substituted or unsubstituted C3-C20 (e.g., C4, C5, C6, C9, C10, C12, C14, C15, C16, C18, etc.) heteroaromatic rings. More preferably… The dashed lines represent the fusion sites of the Cy1 ring.
[0117] Preferably, a is 0.
[0118] Preferably, b is 0.
[0119] Preferably, c is 0.
[0120] Preferably, d is 0.
[0121] Preferably, a1 is 0.
[0122] Preferably, b1 is 0 or 1.
[0123] Preferably, the organic compound has the structure shown in any one of the following:
[0124]
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133]
[0134]
[0135]
[0136]
[0137]
[0138]
[0139]
[0140]
[0141]
[0142]
[0143]
[0144]
[0145]
[0146]
[0147]
[0148]
[0149]
[0150] .
[0151] In the aforementioned compound structures, the number in the upper right corner of the square brackets indicates the number of D atoms in the molecular structure. For example, in B305, "D19" means that any 19 H atoms in the molecular structure are replaced by D atoms. Other similar expressions in this application are similar and will not be repeated here.
[0152] In a second aspect, this application provides an application of the organic compound as described in the first aspect, wherein the organic compound is used in an organic electronic device.
[0153] Preferably, 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.
[0154] Preferably, the organic compound is used in an organic electroluminescent device.
[0155] Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device.
[0156] Thirdly, this application provides an electroluminescent material, the 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 comprising at least one compound having a structure as shown in Formula II;
[0157] Formula II.
[0158] Among them, Y1, Y2, and Y3 are each independently selected from N or CR, and at least two (2 or 3) of Y1, Y2, and Y3 are N.
[0159] R is selected from any one of R0-substituted or unsubstituted C6-C60 aryl groups and R0-substituted or unsubstituted C3-C60 heteroaryl groups.
[0160] L 11 L 12 L 13 Each is independently selected from any one of single bond, R0 substituted or unsubstituted C6-C60 arylene, or R0 substituted or unsubstituted C3-C60 heteroarylene.
[0161] Ar 31 Ar 32 Ar 33 Each is independently selected from any one of R0-substituted or unsubstituted C6-C60 aryl groups or R0-substituted or unsubstituted C3-C60 heteroaryl groups.
[0162] R0 is independently selected from at least one of the following: deuterium, R0' substituted or unsubstituted C1-C30 straight-chain or branched alkyl, R0' substituted or unsubstituted C3-C30 cycloalkyl, R0' substituted or unsubstituted C1-C30 alkoxy, R0' substituted or unsubstituted C1-C30 alkylsilyl, R0' substituted or unsubstituted C6-C30 arylsilyl, R0' substituted or unsubstituted C6-C60 aryl, and R0' substituted or unsubstituted C3-C60 heteroaryl.
[0163] In this application, the "R0 substituted or unsubstituted" group can replace one substituent R0 or multiple substituent R0s. When there are multiple substituent R0s (at least two), they can be the same or different substituents. The same expression used below has the same meaning. Unless otherwise specified, the selection range of R0 is as shown above and will not be repeated.
[0164] R0' is independently selected from at least one of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, C1-C20 ester, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C20 alkylsilyl, C6-C60 aryloxy, C6-C60 arylamino, C6-C30 aryl, and C3-C30 heteroaryl.
[0165] In this application, the group referred to as "R0' substituted or unsubstituted" can replace one substituent R0' or multiple substituents R0'. When there are multiple substituents R0' (at least two), they can be the same or different substituents; the same expression used below has the same meaning. Unless otherwise specified, the selection range of R0' is as shown above and will not be repeated.
[0166] Preferably, the Ar 31 Ar 32 Ar 33 At least one of the following groups is selected from any one of the following groups:
[0167] ;in, The linking site of the representative group.
[0168] U1 is selected from O or S.
[0169] R a R b R c R d R e R f R g Each is independently selected from any one of the following: deuterium, R0'-substituted or unsubstituted C1-C30 straight-chain or branched alkyl, R0'-substituted or unsubstituted C3-C30 cycloalkyl, R0'-substituted or unsubstituted C1-C30 alkoxy, R0'-substituted or unsubstituted C1-C30 alkylsilyl, R0'-substituted or unsubstituted C6-C30 arylsilyl, R0'-substituted or unsubstituted C6-C60 aryl, and R0'-substituted or unsubstituted C3-C60 heteroaryl.
[0170] m is selected from integers from 0 to 3, for example, it can be 0, 1, 2 or 3.
[0171] k is an integer selected from 0 to 4, for example, it can be 0, 1, 2, 3 or 4.
[0172] h is an integer selected from 0 to 7, for example, it can be 0, 1, 2, 3, 4, 5 or 6.
[0173] f and j are each independently selected from integers between 0 and 5, for example, they can be 0, 1, 2, 3, 4 or 5.
[0174] n is an integer selected from 0 to 11, such as 0, 1, 2, 3, 4, 5, 6, 8, 10, etc.
[0175] g is an integer selected from 0 to 6, for example, it can be 0, 1, 2, 3, 4, 5 or 6.
[0176] Preferably, the R a R b R c R d R e R f R gEach is independently selected from deuterium, R0'-substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) straight-chain or branched alkyl groups, R0'-substituted or unsubstituted C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, etc.) cycloalkyl groups, R0'-substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkoxy groups, R0'-substituted or unsubstituted C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, etc.) alkylsilyl groups, and R0'-substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C1... 2. Any one of the following: arylsilyl (C14, C15, C16, C18, C20, etc.), R0'-substituted or unsubstituted C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) aryl, R0'-substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28, etc.) heteroaryl, further preferably deuterium, R0'-substituted or unsubstituted C6-C20 aryl, R0'-substituted or unsubstituted C3-C20 heteroaryl.
[0177] Preferably, the Ar 31 Ar 32 Ar 33 Each group is independently selected from either group A or group B, and the Ar group... 31 Ar 32 Ar 33 At least one of the groups is selected from any one of the groups in group A; the groups in group A include unsubstituted or deuterated groups such as:
[0178] The group B groups include unsubstituted or deuterated groups such as: .
[0179] Preferably, the L 11 L 12 L 13Each is independently selected from any one of single-bonded, R0-substituted or unsubstituted C6-C30 arylene, or R0-substituted or unsubstituted C3-C30 heteroarylene; more preferably, any one of single-bonded, R0-substituted or unsubstituted C6-C20 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, etc.) arylene, or R0-substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, etc.) heteroarylene.
[0180] Preferably, the L 11 L 12 L 13 Each group is independently selected from any one of the following groups: single bond, R0 substituted or unsubstituted:
[0181] .
[0182] Preferably, the second host material comprises at least one of the following compounds:
[0183]
[0184]
[0185]
[0186]
[0187]
[0188]
[0189]
[0190]
[0191] .
[0192] In one specific embodiment, the mass ratio of the first main material to the second main material is (0.1-4):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, 1.9:1, 2.0:1, 2.2:1, 2.3:1, 2.5:1, 3.0:1, 3.5:1, 4.0:1, etc., and is further preferably (0.8-1.5):1.
[0193] Fourthly, this application provides an application of the electroluminescent material as described in the third aspect, wherein the electroluminescent material is applied to an organic electronic device.
[0194] Fifthly, this application 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 the electroluminescent material as described in the third aspect.
[0195] In one embodiment, the organic layer includes a light-emitting layer, which includes an electroluminescent material as described in the third aspect.
[0196] In one specific embodiment, the thickness of the light-emitting layer is 10-60 nm, for example, it can be 12 nm, 15 nm, 18 nm, 20 nm, 22 nm, 25 nm, 28 nm, 30 nm, 32 nm, 35 nm, 38 nm, 40 nm, 42 nm, 45 nm, 48 nm, 50 nm, 52 nm, 55 nm or 58 nm, more preferably 20-50 nm, and more preferably 30-45 nm.
[0197] Preferably, the electroluminescent material serves as the main material of the light-emitting layer.
[0198] In one specific embodiment, the light-emitting layer further includes a doped material.
[0199] In this application, the term "doped material" is also referred to as "dye", "luminescent dye", or "guest material".
[0200] In one specific embodiment, the doping material is a phosphorescent doping material.
[0201] In one specific embodiment, the emission wavelength of the doped material is 500-650 nm, for example, it can be 510 nm, 520 nm, 530 nm, 540 nm, 550 nm, 560 nm, 580 nm, 600 nm, 620 nm or 640 nm, and more preferably 500-550 nm.
[0202] In one specific embodiment, with the electroluminescent material as 100% by mass, the mass of the doped material is 0.1-15%, for example, it can be 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, or 14%, etc.
[0203] In one specific embodiment, the light-emitting layer is prepared by vacuum thermal evaporation.
[0204] In one specific embodiment, the vacuum thermal evaporation method includes: premixing a first host material and a second host material to obtain the electroluminescent material; and evaporating the electroluminescent material and the doped material using a dual-source co-evaporation method to obtain the luminescent layer.
[0205] As a preferred technical solution of this application, the first main material and the second main material are premixed and then vapor-deposited, which has excellent vapor deposition stability, ensuring that the proportion of the main material changes little during the continuous vapor deposition process, thereby ensuring the stability of device performance and further improving the performance consistency in device fabrication.
[0206] In one specific embodiment, the OLED includes a first electrode and a second electrode, and an organic layer located between the electrodes. This organic layer can be further divided into multiple regions. For example, the organic layer may include a hole transport region, a light-emitting layer, and an electron transport region.
[0207] 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.
[0208] 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.
[0209] Organic layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. Compounds used as organic layers can be small organic molecules, large organic molecules, polymers, and combinations thereof.
[0210] 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.
[0211] 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.
[0212]
[0213]
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224]
[0225] .
[0226] 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.
[0227] .
[0228] 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.
[0229] Depending on the technology used, the light-emitting layer can employ various techniques such as fluorescent electroluminescence, phosphorescent electroluminescence, thermally activated delayed fluorescence, thermally activated sensitized fluorescence (TSF), and phosphorescent-assisted thermally activated sensitized fluorescence (pTSF). An OLED device can utilize 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.
[0230] In one embodiment of this application, the material of the light-emitting layer includes a phosphorescent host material, which is the electroluminescent material provided in this application, including a combination of a first host material (structure shown in Formula I) and a second host material (structure shown in Formula II).
[0231] In one embodiment of this application, 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. Wherein D represents deuterium.
[0232]
[0233]
[0234]
[0235]
[0236] .
[0237] In one aspect of this application, 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.
[0238] The organic layer of an OLED 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).
[0239] In one aspect of this application, the electron transport layer material may be selected from, but is not limited to, one or more combinations of ET-1 to ET-73 listed below.
[0240]
[0241]
[0242]
[0243]
[0244]
[0245]
[0246]
[0247]
[0248]
[0249]
[0250]
[0251]
[0252]
[0253]
[0254]
[0255]
[0256]
[0257]
[0258] .
[0259] In one aspect of this application, 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.
[0260] 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.
[0261] In a sixth aspect, this application provides a display device that includes an organic electroluminescent device as described in the fifth aspect.
[0262] In one embodiment, the display device includes a display screen or a display panel.
[0263] In one specific embodiment, the display device is an OLED display.
[0264] This application also provides an electronic device, which includes the aforementioned display device.
[0265] Compared with the prior art, this application has the following beneficial effects:
[0266] The organic compound provided in this application can be used as the main light-emitting material for OLED devices, effectively reducing the driving voltage of the device. Its excellent hole migration ability can promote carrier transport balance, suppress exciton quenching and improve exciton utilization, thereby significantly improving the luminous efficiency and lifetime of the device. At the same time, the organic compound has excellent thermal stability, effectively avoiding the risk of thermal decomposition during the evaporation process, ensuring the stability of the thin film morphology, preventing device performance degradation and further extending the device's lifespan. Attached Figure Description
[0267] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent device provided in Device Example 1;
[0268] Among them, 1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-electron blocking layer, 6-light emitting layer, 7-hole blocking layer, 8-electron transport layer, 9-electron injection layer, 10-cathode, 11-external power supply. Detailed Implementation
[0269] The technical solution of this application will be further described below with reference to the accompanying drawings and specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of this application and should not be construed as specific limitations thereof.
[0270] In one specific embodiment, the organic compound can be prepared via the following exemplary synthetic route:
[0271]
[0272] In one specific embodiment, the organic compound can be prepared via the following exemplary synthetic route:
[0273]
[0274] Among them, L1, L2, L3, R1, R2, R3, R4, Ar1, Ar2, a, b, c, and d have the same limited range as in Equation I;
[0275] Hal represents a halogen or halogen-like group, including but not limited to chlorine, bromine, iodine, methanesulfonyl, trifluoromethanesulfonyl, etc.; Pd2(dba)3 represents tris(dibenzylideneacetone)dipalladium(0), t-BuONa represents sodium tert-butoxide, and SPhos represents 2-biscyclohexylphosphine-2',6'-dimethoxybiphenyl.
[0276] The methods for preparing organic compounds provided in this application include, but are not limited to, the methods described above. Organic compounds synthesized by those skilled in the art using other methods are also within the scope of protection of this application.
[0277] In one specific embodiment, the second host material can be prepared via the following exemplary synthetic route:
[0278]
[0279] Among them, L 11 L 12 L 13 Ar 31 Ar 32 Ar 33 It has the same limiting range as in Equation II;
[0280] K2CO3 represents potassium carbonate, Pd(PPh3)4 represents tetrakis(triphenylphosphine palladium), toluene represents toluene, and EtOH represents ethanol.
[0281] The preparation method of the second main material of this application includes, but is not limited to, the above-described method. Compounds synthesized by those skilled in the art using other methods are also within the scope of protection of this application.
[0282] More specifically, the following synthetic examples exemplify specific methods for synthesizing the organic compounds, and the chemical reagents or raw materials used can be purchased from the chemical product market or custom-made. Alternatively, those skilled in the art can also synthesize them using other known methods.
[0283] The mass spectrometry (m / z) characterization data of the intermediates and target products in the following synthesis examples of this application were obtained by testing with an Agilent 6530 LC / Q-TOF mass spectrometer (APCI ion source).
[0284] Synthesis Example 1: Synthesis of Compound B1:
[0285]
[0286] (1) Synthesis of intermediate IM-1:
[0287] In a 500 mL three-necked flask, SM-1 (2-chlorobenzo[C]phenanthrene, 15.0 g), SM-2 (aniline, 10.6 g), sodium tert-butoxide (5.5 g), toluene (200 mL), Pd2(dba)3 (0.5 g), and SPhos (0.5 g) were added. The mixture was evacuated to nitrogen three times, then heated to 100 °C and reacted for 8 h. After the reaction was complete, the reaction solution was cooled to 50 °C and passed through a silica gel short column to remove insoluble matter. The solution was washed with toluene until no product was obtained. The filtrate was concentrated to give a yellow solid. The crude product was recrystallized from toluene to give 13 g of a pale yellow solid IM-1, MS (M+H): 320.16.
[0288] (2) Synthesis of compound B1:
[0289] In a 250 mL three-necked flask, add IM-1 (8.0 g), SM-3 (7.3 g), sodium tert-butoxide (3.1 g), toluene (120 mL), Pd2(dba)3 (0.25 g), and SPhos (0.22 g). Purge with nitrogen three times under vacuum, then heat to 120 °C and stir for 18 h. A large amount of solid will precipitate during the reaction. After the reaction is complete, cool the reaction solution to room temperature and collect the solid by filtration. Dissolve the crude product in xylene by heating, remove insoluble matter by passing through a short silica gel column, and wash with xylene until no product remains. Concentrate the filtrate to obtain a yellow solid. Recrystallize the solid in xylene to obtain product B1, MS (M+H): 546.33.
[0290] Synthesis Examples 2-48
[0291] The process routes of synthesis examples 2-48 are the same as those of 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 below (the raw materials not listed in the table are the same as those in synthesis example 1).
[0292] Table 1
[0293]
[0294]
[0295]
[0296]
[0297]
[0298]
[0299]
[0300]
[0301] Synthesis Example 49: Compound B305
[0302]
[0303] In a 250 mL three-necked flask, 5 g of B117, 3.5 g of trifluoromethanesulfonic acid, and 50 mL of benzene-D6 were added. The reaction mixture was stirred at 30 °C for 4 h. After the reaction was complete, the temperature was lowered to 0 °C, and the reaction was quenched with 1 N K3PO4 solution. The mixture was then extracted with dichloromethane, and the organic phase was concentrated to give a yellow solid. The solid was recrystallized in xylene and further purified by sublimation to give compound B305, whose molecular weight (M+H) was determined to be 615.57 by mass spectrometry.
[0304] Device Example 1
[0305] A schematic diagram of an organic electroluminescent device is shown below. Figure 1 As shown, the substrate includes a substrate 1, an anode (ITO) 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode (Al) 10 stacked in sequence. The anode 2 and the cathode 10 are connected to an external power supply 11.
[0306] The method for fabricating the organic electroluminescent device is as follows:
[0307] (1) The glass substrate coated with ITO transparent conductive layer was ultrasonically treated in commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone / ethanol, baked in a clean environment until the moisture was completely removed, cleaned with ultraviolet light and ozone, and bombarded with low-energy cation beam.
[0308] (2) Place the glass substrate with the anode in the vacuum chamber and evacuate it to <1×10 -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, and the thickness of the deposited film was 10 nm;
[0309] (3) A 100 nm layer of compound HT-4 was vacuum-deposited on the hole injection layer as a hole transport layer;
[0310] (4) HT-48 compound with a diameter of 87 nm was vacuum-deposited on the hole transport layer as an electron blocking layer;
[0311] (5) Vacuum evaporation of the light-emitting layer of the device on the electron blocking layer. The light-emitting layer includes a mixture of host material (electroluminescent material, B97:C49=50:50, w / w) and dopant material (dye, RPD-10). The mass ratio of host material to dopant material is 100:2.5. The evaporation is carried out by dual-source co-evaporation. The evaporation rate of host material is 0.1 nm / s, the evaporation rate of RPD-10 is 0.002 nm / s, and the total evaporation film thickness is 40 nm.
[0312] (6) A 5 nm layer of compound ET-23 was vacuum-deposited on the light-emitting layer as a hole blocking layer for the device;
[0313] (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 with a film thickness of 25 nm;
[0314] (8) A 1 nm thick LiF layer was vacuum-deposited on the electron transport layer as an electron injection layer;
[0315] (9) A 150 nm thick layer of aluminum is vacuum-deposited on the electron injection layer as a cathode; the total deposition rate of all organic layers and LiF is controlled at 0.1 nm / s, and the deposition rate of the metal electrode is 1 nm / s, to obtain the organic electroluminescent device.
[0316] Device Examples 2-21, Device Comparative Example 1
[0317] An organic electroluminescent device differs from Device Example 1 only in that the host material of the light-emitting layer is replaced with the compounds in Table 2. All other structures, materials, and preparation methods of the device are the same as in Device Example 1. The structure of the first host material in Device Comparative Example 1 is as follows:
[0318] R-1.
[0319] Device performance testing:
[0320] Under the same brightness, the operating voltage, current efficiency, and lifetime of the organic electroluminescent devices prepared in Device Examples 1-21 and Device Comparative Example 1 were measured using a digital source meter and luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, and the current density of the organic electroluminescent device was measured when it reached 10mA / cm². 2 The voltage at that time is the operating voltage; at the same time, the current density at that time is measured, and the ratio of brightness to current density is the current efficiency.
[0321] The LT97's lifespan was tested as follows: at a constant current density of 60 mA / cm². 2 The time taken for the brightness to decay during the test, such as LT97, refers to the time it takes for the brightness to decay to 97% of the initial brightness, in hours;
[0322] The test results are shown in Table 2:
[0323] Table 2
[0324]
[0325]
[0326] As shown in Table 2, compared with Comparative Example 1, the organic electroluminescent device using the organic compound provided in this application as the light-emitting host material has higher luminous efficiency, longer lifespan, and relatively lower driving voltage.
[0327] A comparison of Device Comparative Example 1 and Device Example 1 shows that the OLED device using the organic compound provided in this application exhibits significant improvements in performance indicators such as driving voltage, luminous efficiency, and lifespan. The structural difference between compound R-1 and compound B97 lies solely in that R-1 is an ortho-substituted biphenyl group, while B97 is replaced by a 2-substituted C-type trefoil group. Since the C-type trefoil group has a larger conjugated structure than the biphenyl group, the B97 molecule has better charge transport capability than R-1, resulting in a more balanced carrier transport in the device, reducing exciton and charge quenching phenomena, improving energy transfer efficiency, and thus enhancing the overall performance of the device.
[0328] As can be seen from Device Comparative Example 1 and Device Example 4, although both benzo[C]phenanthrene and triphenylene are fused aromatic rings with large conjugated structures, the device using compound B17 of this application has superior luminescence performance. This may be because benzo[C]phenanthrene of this application has better π-electron delocalization ability, thus having a faster hole mobility. On the other hand, since the fused ring of benzo[C]phenanthrene has a small-angle twisted helical structure in spatial structure, while triphenylene has a planar structure, benzo[C]phenanthrene containing a non-planar structure can prevent exciton quenching caused by overly tight molecular arrangement, thereby improving the efficiency and lifetime of the device.
[0329] Device Examples 22-44, Device Comparative Examples 2-5
[0330] An organic electroluminescent device, differing from Device Example 1 only in that the host material of the light-emitting layer is replaced with the compounds in Table 3; the other structures, materials, and preparation methods of the device are the same as those of Device Example 1. The structures of the first host material in Device Comparative Examples 2-5 are as follows:
[0331] .
[0332] The performance of devices 22-44 and 2-5 were tested using the above testing methods. The test results are shown in Table 3 below:
[0333] Table 3
[0334]
[0335] The comparison between Device Comparative Example 2 and Device Example 22, Device Comparative Example 3 and Device Example 23, and Device Comparative Example 4 and Device Example 24 shows that the benzophenanthrene group has better π electron delocalization ability, thus having a faster hole mobility, and therefore the device has better light-emitting performance.
[0336] As can be seen from Comparative Example 5 and Example 25, fused aromatic ring groups of the benzo[c]phenanthrene type have a larger π conjugation range and better π electron delocalization ability, thus having a faster hole mobility, making the molecule as a whole have better hole injection and transport capabilities, thereby enabling the device to obtain better light-emitting performance.
[0337] Device Examples 45-47
[0338] An organic electroluminescent device is disclosed, which differs from device example 1 only in that the main material of the light-emitting layer is replaced with the compound in Table 4. The other structures, materials and preparation methods of the device are the same as those of device example 1.
[0339] The performance of devices 45-47 was tested using the above testing methods, and the test results are shown in Table 4 below:
[0340] Table 4
[0341]
[0342] As shown in Device Examples 45 and 46, the device lifetime is improved by approximately 19.2% after the organic compound provided in this application is deuterated. As shown in Device Examples 45 and 47, when both the first and second host materials are deuterated compounds, the device lifetime is improved by approximately 30.1%, and the current efficiency is also improved by 3.3%, without any degradation in the driving voltage. This indicates that the organic compound provided in this application has superior stability after deuteration treatment, meeting the performance requirements of long-life devices.
[0343] The applicant declares that this application illustrates the organic compounds, electroluminescent materials, and their applications through the above embodiments, but this application is not limited to the above embodiments, that is, it does not mean that this application must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to this application, equivalent substitutions of the raw materials of the product, addition of auxiliary components, and selection of specific methods, etc., all fall within the protection scope and disclosure scope of this application.
Claims
1. An organic compound, characterized in that, The organic compound has the structure shown in Formula I: Formula I; Among them, L1, L2, and L3 are each independently selected from any one of single bond, substituted or unsubstituted C6-C60 arylene, or substituted or unsubstituted C3-C60 heteroarylene; R1, R2, R3, and R4 are each independently selected from any one of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, C1-C20 ester, substituted or unsubstituted C1-C30 straight-chain or branched alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino; at least two adjacent groups in R1, R2, R3, and R4 are not connected or are linked by chemical bonds to form a ring; Ar2 is selected from any one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C60 heteroaryloxy, substituted or unsubstituted C6-C60 arylamino, and substituted or unsubstituted C3-C60 heteroarylamino. Ar1 is selected from any one of the following groups: ; The linking site of the representative group; The substituents described in L1, L2, L3, R1, R2, R3, R4, and Ar2 are each independently selected from deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, C1-C20 ester group, unsubstituted or R'-substituted C1-C30 straight-chain or branched alkyl group, unsubstituted or R'-substituted C2-C20 alkenyl group, unsubstituted or R'-substituted C1-C30 alkoxy group, unsubstituted or R'-substituted C3-C30 cycloalkyl group, unsubstituted or R'-substituted C3-C30 heterocyclic alkyl group, unsubstituted or R'-substituted C1-C20 alkylsilyl group, unsubstituted or R'-substituted C3-C30 alkylsilyl group, and unsubstituted or R'-substituted C3-C30 alkylsilyl group. At least one of the following: substituted C6-C60 aryloxy, unsubstituted or R'-substituted C6-C60 arylamino, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; the substituents described in L1, L2, L3, R1, R2, R3, R4, and Ar2 are each independently not connected to adjacent ring structures or are connected to form a ring by chemical bonds; at least two adjacent groups in the substituents described in L1, L2, L3, R1, R2, R3, R4, and Ar2 are not connected to each other or are connected to form a ring by chemical bonds; Each R' is independently selected from at least one of deuterium, halogen, cyano, C1-C30 straight-chain or branched alkyl, C3-C30 cycloalkyl, C1-C30 alkoxy, C3-C30 heterocyclic alkyl, C6-C60 aryl, and C3-C60 heteroaryl; at least two adjacent R's are not connected to each other or are linked to each other by chemical bonds to form a ring; each R' is independently not connected to the adjacent ring structure or is linked to each other by chemical bonds to form a ring. a and d are each independently selected from integers between 0 and 4; b and c are each independently selected from integers between 0 and 2. In organic compounds with the structure shown in Formula I, any hydrogen may be optionally substituted with deuterium.
2. The organic compound according to claim 1, characterized in that, The organic compound has a structure as shown in any one of formula II-1, II-2, II-3 or II-4: ; Among them, L1, L2, L3, Ar2, R1, R2, R3, R4, a, b, c, and d have the same limited range as in Equation I.
3. The organic compound according to claim 2, characterized in that, The organic compound has a structure as shown in any one of formulas III-1 to III-22: ; Among them, L1, L2, L3, Ar2, R1, R2, R3, R4, a, b, c, and d have the same limited range as in Equation I; Ar1' is selected from any one of the following groups: ; The linking site of the representative group; a1 is an integer between 0 and 3; b1 is 0 or 1.
4. The organic compound according to any one of claims 1-3, characterized in that, L1, L2, and L3 are each independently selected from any one of the following groups: single bond, substituted, or unsubstituted: ; in, The linking site of the representative group; Z1 is selected from O, S, and NAr. 11 CR 11 R 12 Any one of them; Z2 is selected from N or CR 13 ; L' is selected from any one of C6-C30 arylene or C3-C30 heteroarylene; Ar 11 Selected from any one of unsubstituted or R'-substituted C6-C60 aryl groups and unsubstituted or R'-substituted C3-C60 heteroaryl groups; R 11 R 12 R 13 Each is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, C1-C20 ester, unsubstituted or R'-substituted C1-C30 straight-chain or branched alkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C3-C30 cycloalkyl, unsubstituted or R'-substituted C3-C30 heterocyclic alkyl, unsubstituted or R'-substituted C1-C20 alkylsilyl, unsubstituted or R'-substituted C6-C60 aryloxy, unsubstituted or R'-substituted C6-C60 arylamino, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.
5. The organic compound according to any one of claims 1-3, characterized in that, L1, L2, and L3 are each independently selected from any one of the following groups: single bond, substituted, or unsubstituted: ; in, The linking site of the representative group.
6. The organic compound according to any one of claims 1-3, characterized in that, The Ar2 is selected from any one of the following groups, substituted or unsubstituted: ; in, The linking site of the representative group; Z3 is selected from O, S, and CR. 21 R 22 SiR 23 R 24 ,NAr 21 Any one of them; Z4 is selected from N or CR. 25 ; L'' is selected from any one of C6-C30 arylene or C3-C30 heteroarylene; R 21 R 22 R 23 R 24 R 25 Each is independently selected from any one of hydrogen, deuterium, unsubstituted or R'-substituted C1-C30 straight-chain or branched alkyl, unsubstituted or R'-substituted C2-C20 alkenyl, unsubstituted or R'-substituted C1-C30 alkoxy, unsubstituted or R'-substituted C3-C30 cycloalkyl, unsubstituted or R'-substituted C3-C30 heterocycloalkyl, unsubstituted or R'-substituted C6-C60 aryloxy, unsubstituted or R'-substituted C6-C60 arylamino, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl; R 21 With R 22 They are either not connected or linked by chemical bonds to form a ring, R 23 With R 24 They are either not connected to each other or linked together by chemical bonds to form a ring; Ar 21 It is selected from any one of unsubstituted or R'-substituted C6-C60 aryl groups and unsubstituted or R'-substituted C3-C60 heteroaryl groups.
7. The organic compound according to claim 6, characterized in that, The R 21 R 22 R 23 R 24 R 25 Each group is independently selected from any one of the following groups, either unsubstituted or R'-substituted: C1-C3 straight-chain alkyl, C3-C6 cycloalkyl, phenyl, naphthyl, biphenyl; And / or, the Ar 21 Selected from any one of the following groups, either unsubstituted or R'-substituted: phenyl, naphthyl, anthracene, phenanthrene, biphenyl, terphenyl, tetraphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, benzo[fluorenyl], benzo[furanyl], benzo[thiophene], dibenzo[furanyl], dibenzo[thiophene], carbazole, benzimidazolyl, benzo[indazole], benzo[carbazole], benzo[furanyl], benzo[thiophene], benzo[dibenzofuranyl], benzo[furanyl], benzo[dibenzo[thiophene], indolyl, azadibenzo[thiophene], azadibenzofuranyl.
8. The organic compound according to any one of claims 1-3, characterized in that, The Ar2 is selected from any one of the following groups, whether substituted or unsubstituted: ; in, The linking site of the representative group.
9. The organic compound according to any one of claims 1-3, characterized in that, R1, R2, R3, and R4 are each independently selected from any one of deuterium, halogen, substituted or unsubstituted C1-C10 straight-chain or branched alkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryloxy, and substituted or unsubstituted C3-C30 heteroarylamino.
10. The organic compound according to claim 3, characterized in that, a1 is 0; And / or, the b1 is 0; And / or, the a is 0; And / or, the b is 0; And / or, the c is 0; And / or, the d is 0 or 1.
11. The organic compound according to claim 1, characterized in that, The organic compound has any of the following structures: 。 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.
13. An electroluminescent material, characterized in that, The 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 comprises at least one compound having a structure as shown in Formula II; Formula II; Among them, Y1, Y2, and Y3 are each independently selected from N or CR, and at least two of Y1, Y2, and Y3 are N; R is selected from any one of R0-substituted or unsubstituted C6-C60 aryl groups and R0-substituted or unsubstituted C3-C60 heteroaryl groups; L 11 L 12 L 13 Each is independently selected from any one of single bond, R0 substituted or unsubstituted C6-C60 arylene, or R0 substituted or unsubstituted C3-C60 heteroarylene; Ar 31 Ar 32 Ar 33 Each is independently selected from any one of R0-substituted or unsubstituted C6-C60 aryl groups and R0-substituted or unsubstituted C3-C60 heteroaryl groups; R0 is independently selected from at least one of the following: deuterium, R0' substituted or unsubstituted C1-C30 straight-chain or branched alkyl, R0' substituted or unsubstituted C3-C30 cycloalkyl, R0' substituted or unsubstituted C1-C30 alkoxy, R0' substituted or unsubstituted C1-C30 alkylsilyl, R0' substituted or unsubstituted C6-C30 arylsilyl, R0' substituted or unsubstituted C6-C60 aryl, and R0' substituted or unsubstituted C3-C60 heteroaryl. R0' is independently selected from at least one of deuterium, halogen, cyano, nitro, hydroxyl, amino, aldehyde, C1-C20 ester, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C1-C20 alkoxy, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C20 alkylsilyl, C6-C60 aryloxy, C6-C60 arylamino, C6-C30 aryl, and C3-C30 heteroaryl.
14. The electroluminescent material according to claim 13, characterized in that, The Ar 31 Ar 32 Ar 33 At least one of the following groups is selected from any one of the following groups: ; in, The linking site of the representative group; U1 is selected from O or S; R a R b R c R d R e R f R g Each of the following is independently selected from deuterium, R0'-substituted or unsubstituted C1-C30 straight-chain or branched alkyl, R0'-substituted or unsubstituted C3-C30 cycloalkyl, R0'-substituted or unsubstituted C1-C30 alkoxy, R0'-substituted or unsubstituted C1-C30 alkylsilyl, R0'-substituted or unsubstituted C6-C30 arylsilyl, R0'-substituted or unsubstituted C6-C60 aryl, and R0'-substituted or unsubstituted C3-C60 heteroaryl; m is selected from integers from 0 to 3; k is selected from integers from 0 to 4; h is selected from integers from 0 to 7; f and j are each independently selected from integers from 0 to 5; n is selected from integers from 0 to 11; g is selected from integers from 0 to 6; And / or, the mass ratio of the first main material to the second main material is (0.1-4):
1.
15. The electroluminescent material according to claim 13, characterized in that, The second host material includes at least one of the following compounds: 。 16. An application of the electroluminescent material as described in any one of claims 13-15, characterized in that, The electroluminescent material is used in organic electronic devices.
17. 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 the electroluminescent material as described in any one of claims 13-15.
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