Organic compound and organic light-emitting device

By incorporating deuterium-substituted organic compounds in specific positions of fluorene, the lifespan and efficiency of OLED devices are enhanced, addressing the balance of longevity, efficiency, and capacitance issues.

CN120309490APending Publication Date: 2025-07-15SHANGHAI SANFAN TECHNOLOGY CO LTD
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Patent Information

Application Number
CN202510328394.1
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-03-19
Publication Date
2025-07-15

AI Technical Summary

Technical Problem

The prior art is difficult to effectively reduce device capacitance and improve efficiency while increasing the life of OLED devices.

Method used

Organic compounds with structural formula (I) are prepared by introducing deuterium atoms at specific locations, especially in methylfluorene, and applying them to hole transport layer materials of OLED.

Benefits of technology

Significantly improves the life of OLED devices, reduces device capacitance, and reduces driving voltage and power consumption.

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Abstract

The invention discloses an organic compound which is mainly used for preparing an organic light-emitting device and has a structure as shown in a structural formula (I): # imgabs0 # (I). The organic compound is mainly based on spirofluorene, isotope atoms are introduced at specific positions, the luminous efficiency of the organic compound can be improved through the structural design, and it is found through further in-depth research that the organic compound can be used for preparing the organic light-emitting device. The service life of the organic light-emitting device is greatly prolonged unexpectedly, particularly, it is surprisingly found that capacitance in the organic light-emitting device can be greatly reduced, the driving voltage of the organic light-emitting device can be further reduced through reduction of the capacitance, and therefore power consumption of the organic light-emitting device is greatly reduced.
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Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescent materials, and specifically relates to an organic compound and an organic electroluminescent device comprising such an organic compound. Background Art

[0002] Organic light-emitting devices such as OLEDs are also known as organic electrolaser displays and organic light-emitting semiconductors. The general structure of an OLED device includes an anode, a cathode, and an organic layer between the two electrodes. The commonly used OLED structure currently consists of a substrate, a cathode, an anode, a hole injection layer (HIL), an electron injection layer (EIL), a hole transport layer (HTL), an electron transport layer (ETL), an electron blocking layer (EBL), a hole blocking layer (HBL), a light-emitting layer (EML), etc. Under the action of an electric field, the holes generated by the anode and the electrons generated by the cathode move, are respectively injected into the hole transport layer and the electron transport layer, and migrate to the light-emitting layer. When the two meet in the light-emitting layer, energy excitons are generated, which excite the light-emitting molecules to finally generate visible light.

[0003] There are many factors affecting the lifespan of OLED devices. The internal factors are mainly non-external factors such as the materials or structure of the device itself. Generally speaking, multi-layer structure OLED devices have a longer lifespan than single-layer structure OLED devices; compared with single-layer structure devices, multi-layer structure devices have a smaller energy level barrier that electrons and holes need to overcome when being injected into the cathode and anode, so electrons and holes can be injected into the device interior with a lower driving voltage; in addition, due to the addition of functional layers such as an electron blocking layer, a hole blocking layer, an electron transport layer, and a hole transport layer in multi-layer structure devices, the light-emitting efficiency of the device will be higher. The stability of the materials used in the device will also affect the lifespan of the OLED device; since the device will generate more heat under the drive of an externally applied driving voltage, if the stability of the materials used in the device is poor, the lifespan of the device will also be reduced.

[0004] CN119306618A proposes that performing D substitution (deuteration) at the active sites and the sites with higher electron cloud density of small molecule compounds can obtain good thermal stability, chemical stability, and light stability, and improve the lifespan and efficiency of organic light-emitting devices. However, the applicant has found that after deuteration at the sites of the small branched compounds in this patent, the voltage and capacitance will increase slightly, resulting in an insignificant improvement in this efficiency.

[0005] Therefore, how to improve the efficiency of the device while effectively increasing the lifespan of the device and reducing the capacitance inside the device has become a topic for in-depth research in the academic and industrial circles at the present stage. Summary of the Invention

[0006] The present invention provides an organic compound and an organic light-emitting device containing the organic compound to solve the problems raised in the above technical background.

[0007] The first aspect of this application is to provide an organic compound, preferably an organic compound that can be used to prepare an organic light-emitting device, such as an organic compound for the hole transport layer material of an organic light-emitting device, having the structure shown in formula (I):

[0008]

[0009] Wherein, L1 is selected from a single bond, an arylene group; Ar1 is selected from a substituted or unsubstituted phenyl-containing group, and preferably the phenyl group is connected to L1.

[0010] Wherein, R1-R6 are each independently selected from hydrogen, deuterium, a C1-C6 hydrocarbon group, a C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aromatic group, a substituted or unsubstituted C3-C20 heteroaromatic group;

[0011] At least one or both of R7 and R8 are selected from deuterium or a deuterated hydrocarbon group;

[0012] b, p, m, n are each independently selected from numbers from 0 to 4, and a, q are each independently selected from numbers from 0 to 3.

[0013] In a preferred embodiment, when a is not 0, each R5 can be the same or different.

[0014] In a preferred embodiment, when b is not 0, each R6 can be the same or different.

[0015] In a preferred embodiment, when m is not 0, each R1 can be the same or different.

[0016] In a preferred embodiment, when n is not 0, each R2 can be the same or different.

[0017] In a preferred embodiment, when p is not 0, each R3 can be the same or different.

[0018] In a preferred embodiment, when q is not 0, each R4 can be the same or different.

[0019] In a preferred embodiment, R7 or R8 are each independently selected from one or more of -H, -D, an alkyl group, a deuterated hydrocarbon group, but at least one or both are D or a deuterated hydrocarbon group.

[0020] In a preferred embodiment, the "hydrocarbyl group" in the hydrocarbyl group or deuterated hydrocarbyl group is preferably, independently of each other, a C1-C6 hydrocarbyl group, and may be a saturated or unsaturated aliphatic chain hydrocarbyl group, a saturated or unsaturated aliphatic or aromatic cyclic (monocyclic, fused-ring, spirocyclic, bridged-ring, condensed-ring, etc.) hydrocarbyl group, or one or more of a combination of the aliphatic chain hydrocarbyl group and the aliphatic or aromatic cyclic hydrocarbyl group. For example, it may be an alkyl group, an aliphatic chain hydrocarbon group containing C═C (such as an alkenyl group) or an aliphatic cycloalkyl group, an aliphatic chain hydrocarbon group containing C≡C (such as an alkynyl group) or an aliphatic cycloalkyl group, an aryl group. For example, it may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an allyl group, a benzyl group, a phenyl group, etc.

[0021] In a preferred embodiment, R7 or R8 is preferably at least one or both are deuterated alkyl groups, such as deuterated C1-C6 alkyl groups, for example, -CHD2, -CH2D, -CD3.

[0022] In a preferred embodiment, the arylene group is preferably a C5-C15 arylene group, more preferably a C5-C12 arylene group, and even more preferably a C6-C10 arylene group.

[0023] In a preferred embodiment, the phenyl-containing group may be a single benzene ring, biphenyl, condensed ring, or benzofused aliphatic ring structure. For example, it may be selected from one or more of: phenyl group, fluorenyl group, dibenzofuranyl group, dibenzothiophenyl group.

[0024] In a preferred embodiment, in the term "substituted or unsubstituted phenyl-containing group", the substitution may mean being substituted by the following groups: deuterium, halogen atom, C1-C6 alkyl group, C3-C10 cycloalkyl group, C6-C20 aryl group, C3-C20 heteroaryl group.

[0025] In a preferred embodiment, in the terms "substituted or unsubstituted C6-C20 aryl group" and "substituted or unsubstituted C3-C20 heteroaryl group", the substitution may mean being substituted by the following groups: deuterium, halogen atom, C1-C6 alkyl group, C3-C10 cycloalkyl group, C6-C20 aryl group, C3-C20 heteroaryl group.

[0026] In a preferred embodiment, the halogen atom may be one or more of F, Cl, Br, I.

[0027] In a preferred embodiment, the C1-C6 alkyl group may be one or more of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, CH3-CH2-CH2-CH(CH3)-, CH3-CH2-C(CH3)2-, (CH3-CH2)2C-, CH3-CH2-CH(CH3)-CH2-, CH(CH3)2-(CH3)CH-, CH(CH3)2-CH2-CH2-, (CH3)3C-CH2-, n-hexyl, CH3-CH(CH3)-CH2-CH2-CH2-, CH3-CH2-CH(CH3)-CH2-CH2-, CH3-CH2-CH2-CH(CH3)-CH2-, CH3-CH2-CH2-CH2-CH(CH3)-, CH3-CH(CH3)-CH(CH3)-CH2-, CH3-CH2-CH(CH3)-CH(CH3)-, CH3-CH(CH3)-CH2-CH(CH3)-, CH3-C(CH3)2-CH2-CH2-, CH3-CH2-C(CH3)2-CH2-, CH3-CH2-CH2-C(CH3)2-, CH3-CH(CH3)-C(CH3)2-, CH3-C(CH3)2-CH(CH3)-.

[0028] In a preferred embodiment, the C3-C10 cycloalkyl group may be a carbocyclic ring or an aliphatic heterocyclic structure of C3-10 formed by substituting at least one C on the carbocyclic ring with a heteroatom. For example, it may be one or more of cycloalkyl, cyclohexyl, cyclopentyl, cyclobutyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, dioxane, propylene oxide, ethylene oxide, aziridine, oxetane, piperazine.

[0029] In a preferred embodiment, the C6-C20 aryl group may be selected from

[0030] one or more of them.

[0031] In a preferred embodiment, the C3-C20 heteroaryl group may be one or more of furan, imidazole, pyridine, quinoline, isoquinoline, pyrrole, thiophene, pyrazole, oxazole, isoxazole, thiazole, isothiazole, pyran, pyridazine, pyrimidine, pyrazine, indole, carbazole, benzimidazole, pteridine, 7H-purine, acridine, phenazine, which do not contain a benzene ring or contain a benzene ring.

[0032] In a preferred embodiment, b, p, m, and n are each independently selected from 0, 1, 2, 3, 4. Among them, b, p, m, and n may be 0 simultaneously or not 0 simultaneously.

[0033] In a preferred embodiment, a and q are each independently selected from 0, 1, 2, or 3. Among them, a and q can be 0 simultaneously or not 0 simultaneously.

[0034] In a preferred embodiment, at least one of R3 and R4 is deuterium.

[0035] In a preferred embodiment, Ar1 is preferably a deuterated group.

[0036] In a preferred embodiment, Ar1 is selected from one or more of the following substituted or unsubstituted Among them, and more preferably, the substituents of Ar1 can be one or more (at least 2) deuterium, methyl, -CHD2, -CH2D, -CD3.

[0037] In a preferred embodiment, the organic compound has the structure shown in formula (II):

[0038]

[0039] In a more preferred embodiment, the compound has the structure shown in formula (III):

[0040]

[0041] In a preferred embodiment, the compound has the structure shown in formula (IV):

[0042]

[0043] In a preferred embodiment, the compound is selected from:

[0044]

[0045]

[0046]

[0047]

[0048]

[0049] In a preferred embodiment, the organic compound is selected from one or more of the following structures:

[0050]

[0051]

[0052]

[0053]

[0054]

[0055] Among them, g, h, e, f, and t are numbers from 0 to 3, s is a number from 0 to 4, g + h = 3, and e + f = 3.

[0056] In a preferred embodiment, the organic compound is selected from

[0057]

[0058]

[0059] The second aspect of the present application provides an organic light-emitting device, such as an OLED, which includes a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode. Among them, the organic layer contains the organic compound.

[0060] In a preferred embodiment, the organic layer includes a hole transport layer, an electron blocking layer, an electron transport layer, a hole blocking layer, and a light-emitting layer. More preferably, any one or more (at least 2) of the hole transport layer, the electron blocking layer, the electron transport layer, the hole blocking layer, and the light-emitting layer contain the organic compound. For example, the host material of the hole transport layer is the organic compound. More preferably, all layers contain the organic compound.

[0061] In a preferred embodiment, the hole transport layer further contains a metal oxide hole dopant.

[0062] The applicant found that based on spirofluorene, introducing deuterium atoms at specific positions can significantly improve the lifetime of the device. Moreover, in further in-depth research, it was found that when the hydrogen of the methyl group in methylfluorene is replaced by deuterium, the lifetime of the device has an unexpectedly large increase. In particular, it was unexpectedly found that the capacitance in the device has a significant decrease. The decrease in capacitance can further reduce the driving voltage of the device and significantly reduce the power consumption of the device. Detailed implementation mode

[0063] The present invention provides an organic compound and an organic light-emitting device. To make the purpose, technical solution, and effects of the present invention clearer and more definite, the following examples are given to further illustrate the present invention in detail. It should be understood that the specific embodiments described here are only used to explain the present invention and are not used to limit the present invention.

[0064] It should be noted that the terms "first", "second", etc. in the description and claims of the present invention are used to distinguish similar objects and do not necessarily describe a specific order or sequence. It should be understood that the data used in this way can be interchanged under appropriate circumstances. In addition, the terms "comprising" and "having" and any variations thereof are intended to cover non-exclusive inclusion. For example, a process, method, system, product or device comprising a series of steps or units need not be limited to those steps or units clearly listed, but may include other steps or units not clearly listed or inherent to these processes, methods, products or devices.

[0065] In the following embodiments of the present application, the deuterated compounds are customized from OLED intermediate manufacturers, other initial raw materials and solvents are purchased from the National Pharmaceutical Group, and some common OLED intermediate products are purchased from domestic OLED intermediate manufacturers. If palladium catalysts, ligands, etc. are involved, they are purchased from Shaanxi Ruike New Materials Co., Ltd. Unless otherwise specified, all percentages are weight percentages and all dosage ratios are weight ratios.

[0066] 1 The 1H NMR data was measured using a Varian 400-MR nuclear magnetic resonance spectrometer; LC-MS (liquid chromatography-mass spectrometry) was tested on a UPLC+SQD2 model instrument from Waters Corporation. The experimental methods without specific conditions noted in the following examples are generally determined according to national standards. If there is no corresponding national standard, they are determined according to general international standards, conventional methods and conditions, or according to the conditions recommended by the manufacturer, or according to the product instructions.

[0067] Example 1:

[0068]

[0069] The preparation method steps include:

[0070] Step 1, Synthesis of Intermediate 1

[0071] In a three-necked flask controlled under an argon atmosphere, 50 mmol of raw material 11, 50 mmol of raw material 12 and 120 mmol of NaOt-Bu were successively added, and then 5 mol‰ of Pd(dba)2 and 6 mol‰ of t-Bu3PHBF4 were added. 800 ml of xylene was injected as a solvent, and an argon displacement circulation system was established. The system was heated to 140 ± 2 °C through an oil bath temperature control device, and mechanical stirring was maintained for 20 hours to complete the metal-catalyzed coupling process.

[0072] After the reaction was terminated, the temperature was lowered to 20 °C, and deionized water was injected to initiate precipitation. Solid-liquid separation was carried out, and the obtained off-white precipitate was washed with deionized water and dried to obtain a crude product in the form of a white powder. It was purified by gradient elution column chromatography (n-hexane:ethyl acetate = 5:1 → 3:1), and finally intermediate 1 was obtained. HPLC detection showed a single main peak (99.5%), LCMS: M / Z 526.25 (M+), and the theoretical yield was 76%.

[0073] Step 2, Synthesis of Compound 1

[0074] Referring to the method of step 1, intermediate 1 was reacted with raw material 13 to obtain compound 1.

[0075] LCMS: M / Z 724.38 (M+), the chromatographic purity was increased to 99.9%, and the total yield was 48%.

[0076] Example 2:

[0077]

[0078] The preparation method of compound 2 refers to Example 1. In step 1, raw material 21 was used to replace raw material 11 in Example 1, and raw material 22 was used to replace raw material 12 in Example 1; in step 2, intermediate 2 was used to replace intermediate 1 in Example 1, and raw material 23 was used to replace raw material 13 in Example 1.

[0079] Total yield: 36%; HPLC purity: 99.9%; LCMS: M / Z 664.29 (M+).

[0080] Example 3:

[0081]

[0082] The preparation method of compound 3 refers to Example 1. In step 1, raw material 31 was used to replace raw material 11 in Example 1, and raw material 32 was used to replace raw material 12 in Example 1; in step 2, intermediate 3 was used to replace intermediate 1 in Example 1, and raw material 33 was used to replace raw material 13 in Example 1.

[0083] Total yield: 32%; HPLC purity: 99.9%; LCMS: M / Z 728.41 (M+).

[0084] Example 4:

[0085]

[0086] The preparation method of Compound 4 refers to Example 1. In Step 1, raw material 41 is used to replace raw material 11 in Example 1, and raw material 42 is used to replace raw material 12 in Example 1; in Step 2, intermediate 4 is used to replace intermediate 1 in Example 1, and raw material 43 is used to replace raw material 13 in Example 1.

[0087] Total yield: 37%; HPLC purity: 99.9%; LCMS: M / Z 697.32 (M+).

[0088] Example 5:

[0089]

[0090] The preparation method of Compound 5 refers to Example 1. In Step 1, raw material 51 is used to replace raw material 11 in Example 1, and raw material 52 is used to replace raw material 12 in Example 1; in Step 2, intermediate 5 is used to replace intermediate 1 in Example 1, and raw material 53 is used to replace raw material 13 in Example 1.

[0091] Total yield: 35%; HPLC purity: 99.9%; LCMS: M / Z 741.33 (M+).

[0092] Example 6:

[0093]

[0094] The preparation method of Compound 6 refers to Example 1. In Step 1, raw material 61 is used to replace raw material 11 in Example 1, and raw material 62 is used to replace raw material 12 in Example 1; in Step 2, intermediate 6 is used to replace intermediate 1 in Example 1, and raw material 63 is used to replace raw material 13 in Example 1.

[0095] Total yield: 36%; HPLC purity: 99.9%; LCMS: M / Z 840.53 (M+).

[0096] Example 7:

[0097]

[0098] The preparation method of Compound 7 refers to Example 1. In Step 1, raw material 71 is used to replace raw material 11 in Example 1, and raw material 72 is used to replace raw material 12 in Example 1; in Step 2, intermediate 7 is used to replace intermediate 1 in Example 1, and raw material 73 is used to replace raw material 13 in Example 1.

[0099] Total yield: 34%; HPLC purity: 99.9%; LCMS: M / Z 845.39 (M+).

[0100] Example 8:

[0101]

[0102] For the preparation method of Compound 8, refer to Example 1. In Step 1, replace raw material 11 in Example 1 with raw material 81 and replace raw material 12 in Example 1 with raw material 82; in Step 2, replace intermediate 1 in Example 1 with intermediate 8 and replace raw material 13 in Example 1 with raw material 83.

[0103] Total yield: 33%; HPLC purity: 99.9%; LCMS: M / Z 700.34 (M+).

[0104] Example 9:

[0105]

[0106] For the preparation method of Compound 9, refer to Example 1. In Step 1, replace raw material 11 in Example 1 with raw material 91 and replace raw material 12 in Example 1 with raw material 92; in Step 2, replace intermediate 1 in Example 1 with intermediate 9 and replace raw material 13 in Example 1 with raw material 93.

[0107] Total yield: 36%; HPLC purity: 99.9%; LCMS: M / Z 722.37 (M+).

[0108] Example 10

[0109] The preparation method of the organic electroluminescent device is as follows:

[0110] 1. First, deposit a mixed material of H1 and H2 (mass ratio 1:99) on the anode reflective layer by co-evaporation technology to prepare a hole injection thin film with a thickness of 10 nm.

[0111] 2. After the preparation of the hole injection layer is completed, vapor deposition is carried out using a single-component H2 material to construct a first hole transport functional layer with a thickness of about 100 nm.

[0112] 3. Use Compound 1 of the present invention as the functional material to form a second hole transport layer with a thickness of 40 nm through vacuum evaporation process.

[0113] 4. The light-emitting matrix material H3 and the dopant H4 are compounded and deposited in a ratio of 95:5 by dual-source co-evaporation method to construct a 40-nm light-emitting layer on the surface of the pre-functional layer.

[0114] 5. A charge control layer with a precisely controlled thickness of 5 nm is constructed at the interface of the light-emitting layer, and H5 is used as the hole blocking material.

[0115] 6. Prepare a 30-nm electron transport functional thin film by binary co-blending deposition process (mass ratio of H6 to LiQ is 4:6).

[0116] 7. Implement the deposition process of ytterbium (Yb) thin film at the electron transport interface to form a 5-nm electron injection transition layer.

[0117] 8. Finally, adopt the co-evaporation method of two metals (the deposition rate ratio of Mg / Ag is 1:9) to form a 15-nm composite cathode layer on the device surface.

[0118]

[0119] Examples 11 - 19

[0120] The difference from Example 10 is only that when forming the second hole transport layer, Compounds 2 - 9 are respectively used to replace Compound 1.

[0121] Comparative Examples 1 - 6

[0122] The difference from Example 10 is only that when forming the second hole transport layer, Compounds D1 - D6 are respectively used to replace Compound 1.

[0123] Compounds D1 - D6 can be prepared by referring to the method of Example 1.

[0124]

[0125] Device performance test

[0126] Based on the light attenuation monitoring system (McScience Polaronix platform), configure a multi-channel optoelectronic sensing array and a constant current driving module to establish an accelerated aging test model in a light-free environment. By recording the light intensity attenuation curve in real time, deduce the reliability index of the device under standard working conditions. All test samples are prepared in the same batch for synchronous verification, and the reference group (Comparative Example 2) is used as the reference unit. By introducing the relative performance coefficient evaluation system, the voltage characteristics, device efficiency, device life, and capacitance at the threshold voltage of the control group (Comparative Example 1) are set as the normalized reference value 1, and the parameters of the experimental group (Examples 1 - 10) and other comparison groups are all converted into proportional factors relative to this reference.

[0127] Table 1 Test results of device voltage, efficiency, life, and capacitance

[0128]

[0129] According to the results in Table 1, when used as the second hole transport layer of the light-emitting device, compared with the comparative compounds D1-D6, the voltages of the compounds 1-10 of the present application are all reduced, the lifetime is significantly improved, and the device capacitance is reduced. Among them, when comparing Compound 1 with D4 and Compound 10 with D5, after introducing deuterated groups at the R8 or R7 position in the present application, the voltage and capacitance of the device are reduced, the efficiency is improved, and especially the lifetime is greatly improved; when comparing Compound 1 and Compound 10, although the D content of Compound 1 is higher, the performance of the device is basically the same as that of the device of Compound 10. The reason may be that the position of D substitution is more critical than the number of deuterium atoms, and deuterium at the R8 or R7 position has higher efficiency in improving the lifetime.

[0130] Introducing deuterium atoms into the OLED material (especially H in the benzene ring is replaced by D) can improve the lifetime of the device, but the voltage will increase slightly, resulting in an insignificant change in efficiency. The reason may be that the D atom has a larger mass and spatial volume than the H atom, which can inhibit spatial rotation. Therefore, the C-D bond is more stable than the C-H bond and can extend the service life. Therefore, when deuterium atoms are introduced into the spirofluorene structure, the lifetime of the device is improved.

[0131] However, the research of the present application finds that introducing deuterium atoms into specific positions (such as CD3 replacing CH3 in methylfluorene) can better improve the lifetime and efficiency than the comparative compounds D1-D6. In particular, the present application unexpectedly finds that introducing D into the methyl group of methylfluorene can significantly reduce the capacitance of the device compared with directly replacing H in the benzene ring with D. Thus, the present application can achieve the technical effects of improving efficiency, increasing the lifetime, and reducing capacitance.

[0132] In summary, the organic light-emitting device prepared by using the compound of the present invention has a lower voltage, high efficiency, especially a high lifetime, and a small capacitance. The compound of the present invention is more suitable for OLEDs.

[0133] The specific embodiments of the present invention have been described in detail above, but they are only examples, and the present invention is not limited to the specific embodiments described above. For those skilled in the art, any equivalent modifications and substitutions to the present invention are also within the scope of the present invention. Therefore, all equivalent transformations and modifications made without departing from the spirit and scope of the present invention should be covered within the scope of the present invention.

Claims

1. An organic compound, characterized in that, It contains the structure shown in the structural formula (I): (I) Wherein, L1 is selected from a single bond or an arylene group; Ar1 is selected from a substituted or unsubstituted phenyl-containing group, and preferably the phenyl is connected to L1; Wherein, R1-R6 are each independently selected from hydrogen, deuterium, a C1-C6 alkyl group, a C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, and a substituted or unsubstituted C3-C20 heteroaryl group; At least one or both of R7 and R8 are selected from deuterium or a deuterated hydrocarbon group; b, p, m, n are each independently selected from numbers from 0 to 4, and a, q are each independently selected from numbers from 0 to 3.

2. The organic compound according to claim 1, characterized in that, It contains the structure shown in the structural formula (II), (III), or (IV): (II) (III) (IV).

3. The compound according to claim 1, characterized in that, The compound is selected from: 。 4. The compound according to claim 1, wherein Selected from one or more of the following structures: ; Wherein, g, h, e, f, t are numbers from 0 to 3, s is a number from 0 to 4, and g + h = 3, e + f = 3.

5. The compound according to claim 1, wherein The arylene group is a C5-C15 arylene group, more preferably a C5-C12 arylene group, and even more preferably a C6-C10 arylene group; the phenyl-containing group is selected from one or more of phenyl, fluorenyl, dibenzofuranyl, and dibenzothiophenyl.

6. The compound according to claim 1, wherein, At least one of R3 and R4 is deuterium, and Ar1 is a deuterated group.

7. The compound according to claim 1, characterized in that, The Ar1 is selected from substituted or unsubstituted one or more of those in , more preferably, the substituent of Ar1 may be one or more deuterium, methyl, -CHD2, -CH2D, -CD3.

8. The compound according to claim 1, wherein R7 or R8 are each independently selected from one or more of -H, -D, an alkyl group, and a deuterated hydrocarbon group, but at least one or both are D or a deuterated hydrocarbon group; preferably at least one or both are deuterated alkyl groups, such as deuterated C1-C6 alkyl groups, such as -CHD2, -CH2D, -CD3.

9. An organic light-emitting device, characterized in that, It contains a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer contains the organic compound.

10. The organic light emitting device according to claim 9, wherein The organic layer includes a hole transport layer, an electron blocking layer, an electron transport layer, a hole blocking layer, and a light-emitting layer. More preferably, the organic compound is contained in any one or more of the hole transport layer, the electron blocking layer, the electron transport layer, the hole blocking layer, and the light-emitting layer. For example, the host material of the hole transport layer is the organic compound.

Citation Information

Patent Citations

  • Compound and organic light-emitting device

    CN119306618A