An organic compound, an OLED having the same, and a display or lighting device

By designing a seven-membered heterocyclic parent core structure containing silicon and combining with aryl substitution modified organic compounds, the problems of high driving voltage and short display life in OLED display technology are solved, and higher luminescence efficiency and longer life are achieved .

CN118812579BActive Publication Date: 2025-02-07ZHEJIANG HUAXIAN PHOTOELECTRICITY TECHNOLOGY CO LTD
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Patent Information

Application Number
CN202411296607.9
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-09-18
Publication Date
2025-02-07
Estimated Expiration
2044-09-18

AI Technical Summary

Technical Problem

The existing OLED display technology has problems such as high driving voltage and short display life, which affects its further application.

Method used

By designing a silicon-containing seven-membered heterocyclic parent core structure and combining with suitable aryl substitution modified organic compounds, charge transport performance and molecular stability are improved, steric hindrance is increased, and molecules are prevented from excessive planarization and crystallization.

Benefits of technology

This compound acts as a hole transport layer or a light emitting auxiliary layer in an OLED device, which can improve luminescence efficiency and life, suppress device efficiency roll-off, and ensure excellent luminescence performance.

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Abstract

The present invention relates to the technical field of preparation of organic optoelectronic materials, and specifically to an organic compound, an OLED having the compound, and a display or lighting device. The organic compound involved in the present invention has a silicon-containing seven-membered heterocyclic mother core structure, which is beneficial to the transmission of charges and the stability of molecules after being substituted and modified with specific aromatic groups, and can also increase the steric hindrance of the molecules, preventing the molecules from being excessively planarized and forming crystals at high temperatures. Based on the unique structural characteristics of the present invention, it has good hole injection and migration performance. When it is used as an electron blocking layer and a light-emitting auxiliary layer material, it can suppress the efficiency roll-off of the device and effectively improve the hole injection and migration efficiency in the device, thereby ensuring that the device obtains excellent luminous efficiency and device life. The preparation process of the compound of the present invention is simple and easy, the raw materials are easily available, it is suitable for mass production and amplification, and has good industrialization prospects.
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Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric material preparation, and in particular to an organic compound, an OLED having the compound, and a display or lighting device. Background Art

[0002] Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, are a technology that allows organic materials to emit light through carrier injection and recombination under the action of an electric field. It can convert electrical energy into light energy through organic light-emitting materials. OLED is essentially a thin-film stacking device. In theory, when both the anode and the cathode are transparent electrodes, the light emitted by the light-emitting layer can be transmitted from the anode to the outside of the device and from the cathode to the outside of the device. Therefore, according to the different paths of light transmission, devices can be divided into bottom-emitting devices and top-emitting devices. The light of the bottom-emitting device is transmitted from the anode to the outside of the device through the substrate, and the light of the top-emitting device is transmitted to the outside of the device through the cathode. The light emission direction of the top-emitting device is on the cathode side, without passing through the substrate, and the image is more delicate and clear, and the color is also higher. However, in the structure of the top-emitting organic electroluminescent device, the brightness and color observed at different viewing angles will be very different, which seriously affects the product performance.

[0003] At present, OLED display technology still has the problems of high driving voltage and short display life, which seriously affect the further application of this technology. Therefore, it is necessary to continue to work hard to develop organic light-emitting devices with low voltage drive, high brightness and long life. Organic hole materials play an important role in transferring holes injected from the anode to the light-emitting layer. Hole transport materials with excellent hole mobility are beneficial to the injection balance of carriers in the device, thereby reducing the driving voltage of the device. On the other hand, in order to prevent the excitons generated in the light-emitting layer from diffusing to the hole transport layer, resulting in color cast and reduced luminous efficiency, the hole transport layer is also required to block the excitons from diffusing outward, prevent efficiency roll-off and improve the stability of the device.

[0004] In order to continuously improve the performance of OLED devices, it is necessary not only to innovate the structure and manufacturing process of OLED devices, but also to continuously research and innovate on OLED optoelectronic functional materials, create higher-performance OLED functional materials, and reasonably match them with existing materials to improve the luminous efficiency and service life of the device. Therefore, finding suitable OLED optoelectronic functional materials for OLED devices to solve the above problems is a long-term demand in the field. Summary of the invention

[0005] The object of the present invention is to provide an organic compound, an OLED having the compound, and a display or lighting device in view of the problems existing in the prior art. The present invention obtains a new organic compound by modifying a silicon-containing seven-membered heterocyclic core structure with appropriate aromatic substitution, which can improve the charge transfer performance and molecular stability, increase molecular steric hindrance, and prevent the molecule from being excessively planarized and forming crystals at high temperatures. It is particularly suitable for use in light-related devices or components. In particular, the compound of the present invention can be used as a hole transport layer or a light-emitting auxiliary layer in the device or component to improve the luminous efficiency and life of the light-emitting device.

[0006] In order to achieve the purpose of the present invention, the technical solution of the present invention is as follows:

[0007] According to one or more embodiments, the present invention provides an organic compound having a structure shown in the following formula (I):

[0008] ;

[0009] In formula (I), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group;

[0010] R1 and R2 are each independently selected from hydrogen, deuterium, C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl;

[0011] R3-R5 represent a polysubstituted group, which may be unsubstituted, monosubstituted or polysubstituted; each time R3-R5 appears, R3-R5 are independently selected from one or more of hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;

[0012] In formula (I), adjacent substituents may be connected to form a ring; when there is substitution, the substituent is selected from one or more of hydrogen, deuterium, C1-C12 alkyl, and C6-C18 aryl.

[0013] Preferably, in formula (I), R1 and R2 may be connected to form a ring, and R3 and R4 may be connected to form a ring.

[0014] Preferably, in formula (I), Ar1 and Ar2 are independently selected from any one or more of phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, dimethylfluorenyl and terphenyl.

[0015] Preferably, L1 and L2 are each independently selected from a single bond or a C6-C18 aromatic group; further preferably, L1 and L2 are each independently selected from any one or more of a single bond, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

[0016] Preferably, R1 and R2 are each independently selected from hydrogen, deuterium, C1-C12 alkyl, C6-C18 aryl; further preferably, R1 and R2 are each independently selected from hydrogen, deuterium, methyl, phenyl; when R1 and R2 are both selected from phenyl, R1 and R2 can be connected to form a ring;

[0017] Preferably, R3 to R5 are each independently selected from any one or more of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, and dimethylindenyl, and adjacent substituents may be connected to form a ring.

[0018] Optionally, at least one hydrogen in the compounds of the present invention may be replaced by deuterium.

[0019] According to one or more embodiments, the compound of the present invention is selected from any one of the chemical structures shown below:

[0020] .

[0021] According to one or more embodiments, the present invention also provides use of an organic compound having a structure as shown in the above formula (I) in preparing an organic electroluminescent device.

[0022] According to one or more embodiments, the present invention also provides an organic electroluminescent device, which includes: a substrate layer; a first electrode, which is on the substrate; an organic light-emitting functional layer, which is on the first electrode; a second electrode, which is on the organic light-emitting functional layer; the organic light-emitting functional layer contains an organic compound with a structure as shown in the above formula (I).

[0023] In a preferred embodiment, the organic light-emitting functional layer includes a hole transport layer, a light-emitting layer, and a light-emitting auxiliary layer located between the hole transport layer and the light-emitting layer; the hole transport layer or the light-emitting auxiliary layer contains an organic compound having a structure as shown in the above formula (I).

[0024] Optionally, the light-emitting layer of the organic electroluminescent device comprises a light-emitting composition component, wherein the light-emitting composition component comprises a compound having a structure represented by the following formula (II) and a compound having a structure represented by the following formula (III);

[0025] ;

[0026] In formula (II), Q1-Q2 are each independently selected from hydrogen, deuterium, and a C6-C30 aryl group; in formula (III), Q3-Q5 are each independently selected from hydrogen, deuterium, and a C6-C30 aryl group.

[0027] In some embodiments, Q1-Q2, Q3-Q4 are each independently selected from hydrogen, deuterium, phenyl, biphenyl or naphthyl.

[0028] Preferably, the compound of the structure represented by formula (II) and the compound of the structure represented by formula (III) in the light-emitting composition are combined in equal proportions.

[0029] In some embodiments, the compound represented by formula (II) is selected from any one of the following chemical structures:

[0030] .

[0031] In some embodiments, the compound of formula (III) is selected from any one of the following chemical structures, wherein "D" represents deuterium:

[0032] .

[0033] Preferably, different organic light-emitting material layers in the organic electroluminescent device are stacked and combined laterally or vertically.

[0034] According to one or more embodiments, the organic electroluminescent device of the present invention can be used in OLED display or lighting devices. Specifically, it can be used in the commercial field, such as display screens of products and equipment such as POS machines and ATM machines, copiers, vending machines, game machines, gas stations, card machines, access control systems, electronic scales, etc.; in the communication field, such as display screens of products such as mobile phones, various video intercom systems (videophones), mobile network terminals, ebooks (electronic books), etc.; in the computer field, such as display screens of home and / or commercial computers (PC / workstations, etc.), PDAs and laptops; in consumer electronic products, such as display screens of decorative items (soft screens) and lamps, various audio equipment, MP3, calculators, digital cameras, head-mounted displays, digital video cameras, portable DVDs, portable televisions, electronic clocks, handheld game consoles, various household appliances (OLED TVs), etc.; in the transportation field, such as various indicator and symbol display screens such as GPS, car audio, car phones, aircraft instruments and equipment.

[0035] Preferably, the organic electroluminescent device prepared by the present invention is used in smart phones, tablet computers, smart wearable devices, televisions, VR, micro-display fields, and automobile central control screens or automobile taillights.

[0036] According to one or more embodiments, the present invention further provides a composition comprising an organic compound having a structure as shown in the above formula (I).

[0037] According to one or more embodiments, the present invention further provides a preparation comprising an organic compound having a structure as shown in the above formula (I) and at least one solvent.

[0038] According to one or more embodiments, the present invention further provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

[0039] Compared with the prior art, the present invention has the following beneficial effects:

[0040] The organic compound involved in the present invention has a silicon-containing seven-membered heterocyclic core structure, which is beneficial to the transfer of charge and the stability of the molecule after being substituted with a specific aromatic group, and can also increase the steric hindrance of the molecule, preventing the molecule from being excessively planarized and forming crystals at high temperatures. Based on the unique structural characteristics of the present invention, it has good hole injection and migration performance. When it is used as an electron blocking layer and a light-emitting auxiliary layer material, the efficiency roll-off of the device can be suppressed and the hole injection and migration efficiency in the device can be effectively improved, thereby ensuring that the device obtains excellent luminous efficiency and device life. The preparation process of the compound of the present invention is simple and easy, the raw materials are easily available, it is suitable for mass production and amplification, and has good industrialization prospects. DETAILED DESCRIPTION

[0041] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments in the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention. Unless otherwise specified, all commercial reagents involved in the following tests are used directly after purchase, and specific reagents are directly customized and used directly at Tianjin Zhujinshi Chemical Co., Ltd.

[0042] The "alkyl" of the present invention refers to a monovalent alkyl group having 1 to 30 carbon atoms, preferably 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms. Examples of this term include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, etc. In addition, the alkyl group may be optionally substituted.

[0043] The "cycloalkyl" of the present invention refers to a cyclic alkyl group having 3 to 30 carbon atoms and a monocyclic or polycyclic condensed ring, preferably 3 to 14 carbon atoms, more preferably 3 to 9 carbon atoms, which can be arbitrarily substituted by 1 to 3 alkyl groups. Such cycloalkyl groups include, for example, monocyclic structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexane, cyclooctyl, 1-methylcyclopropyl, 2-methylcyclopentyl, 2-methylcyclooctyl, methylcyclohexane, etc., or polycyclic structures such as adamantyl, etc.

[0044] The "aryl" of the present invention refers to an unsaturated aromatic carbocyclic ring having 6-30 carbon atoms and having a monocyclic (such as phenyl) or polycyclic condensation (such as naphthyl or anthracenyl). Preferably 6-18 carbon atoms, more preferably 6-12 carbon atoms. Preferred aryl groups include phenyl, biphenyl, naphthyl, terphenyl, etc. Unless otherwise defined for individual substituents, such aryl groups may be optionally substituted by 1-3 of the following substituents: hydroxyl, acyl, acyloxy, alkyl, alkoxy, alkenyl, alkynyl, amino, aminoacyl, aryl, aryloxy, carboxyl, carboxyl ester, aminocarboxyl ester, cyano, halogen, nitro, heteroaryl, heterocycle, thioalkoxy, trihalomethyl, etc. Preferred substituents include alkyl, alkoxy, halogen, cyano, nitro, trihalomethyl and thioalkoxy. But not limited thereto.

[0045] The "heteroaryl" described in the present invention refers to a general term for groups having 6-30 carbon atoms and in which one or more aromatic carbon atoms in the aromatic group are replaced by heteroatoms; preferably 6-18 carbon atoms, and the heteroatoms include but are not limited to oxygen (O), sulfur (S), nitrogen (N), silicon (Si) or germanium (Ge) atoms. The heteroaryl group can be a monocyclic heteroaryl group or a condensed ring heteroaryl group, and examples may include pyridyl, pyrrolyl, pyridyl, thienyl, furanyl, indolyl, quinolyl, isoquinolyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

[0046] The "substitution" of the present invention is mono-, di-, tri-, tetra- or penta-substitution, independently selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, biphenyl or benzyl, etc. The substitution can be carried out by a single bond or fusion.

[0047] Throughout the specification, unless explicitly described to the contrary, "comprising" any component will be understood to imply the inclusion of other elements, rather than excluding any other elements. In addition, it should be understood that throughout the specification, when an element such as a layer, film, region or substrate is referred to as being "on" or "above" another element, it can be "directly on" another element, or there may be intervening elements. In addition, "on..." or "above..." means being located above the target portion, and does not necessarily mean being located above according to the direction of gravity.

[0048] An object of the present invention is to provide an organic electroluminescent device (OLED), which comprises: a substrate layer; a first electrode, which is on the substrate; an organic light-emitting functional layer, which is on the first electrode; a second electrode, which is on the organic light-emitting functional layer; preferably, the organic light-emitting functional layer comprises a hole transport layer, a light-emitting layer, and a light-emitting auxiliary layer located between the hole transport layer and the light-emitting layer; more preferably, the hole transport layer or the light-emitting auxiliary layer comprises an organic compound having a structure represented by formula (I).

[0049] In a preferred embodiment of the present invention, the light-emitting layer comprises a light-emitting composition compound, and the light-emitting composition comprises a compound having a structure represented by formula (II) and a compound having a structure represented by formula (III).

[0050] The substrate of the present invention can be any substrate used in typical organic light-emitting devices. It can be a glass or transparent plastic substrate, or a substrate of an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and waterproofness. Depending on the properties of the substrate, the use direction is different. Other materials in the organic electroluminescent device can be selected from the known related materials used in OLED devices.

[0051] As a guest material capable of producing blue fluorescence, blue phosphorescence, green fluorescence, green phosphorescence and blue-green fluorescence, it is not only required to have an extremely high fluorescence quantum luminescence efficiency, but also to have an appropriate energy level that can effectively absorb the excitation energy of the host material to emit light. Such materials are not particularly limited.

[0052] Example 1: Synthesis of Compound P1

[0053] ;

[0054] A1 (10 mmoL), B1 (22 mmoL), sodium tert-butoxide (22 mmoL), and 200 mL of toluene were added to a three-necked reaction flask. After nitrogen substitution, Pd2(dba)3 (5×10 -2 mmoL), tri-tert-butylphosphine (5×10 -2 100mL), heated to 110°C, reacted under reflux for 6 hours, and then stopped the reaction. Cooled to room temperature, then added 200mL of water and layered. After washing twice, concentrated to remove toluene, added 100mL of methanol, pulped for 6 hours, filtered, and the obtained solid was recrystallized from ethyl acetate twice to obtain the target product P1, LC-MS (m / z) (M+): theoretical value is 729.29, and the test value is 729.52.

[0055] Example 2: Synthesis of Compound P9

[0056] ;

[0057] (1) Add A1 (10 mmol), B1 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of toluene to a three-necked reaction flask. After vacuuming and replacing nitrogen three times, add Pd2(dba)3 (5×10 -2 mmoL)、S-Phos(5×10 -2 mmoL), heated to 110°C, reacted under reflux for 6 hours, and then stopped the reaction. Cooled to room temperature, then added 200mL of water, and layered. After washing twice, concentrated to remove toluene, then added 100mL of n-heptane, and slurried for 2 hours to obtain the intermediate product P 9-1;

[0058] (2) Add P to the three-necked reaction bottle. 9-1 (10 mmoL), C1 (12 mmoL), sodium tert-butoxide (12 mmoL), toluene 200 mL, after nitrogen replacement, add Pd2 (dba) 3 (5 × 10 -2 mmoL), tri-tert-butylphosphine (5×10 -2 100mL), heated to 110°C, reacted under reflux for 6 hours, and then stopped the reaction. Cooled to room temperature, then added 200mL of water, and layered. After washing twice, concentrated to remove toluene, added 100mL of methanol, pulped for 6 hours, filtered, and the obtained solid was recrystallized from ethyl acetate twice to obtain the target product P9, LC-MS (m / z) (M+): theoretical value is 769.32, and the test value is 769.58.

[0059] Example 3: Compound P 10 Synthesis

[0060] ;

[0061] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 10 LC-MS (m / z) (Μ+): theoretical value is 845.39, measured value is 845.57.

[0062] Example 4: Compound P 22 Synthesis

[0063] ;

[0064] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 22LC-MS (m / z)(Μ+): theoretical value is 783.30, measured value is 783.61.

[0065] Example 5: Compound P 30 Synthesis

[0066] ;

[0067] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 30 LC-MS (m / z)(Μ+): theoretical value is 875.30, measured value is 875.45.

[0068] Example 6: Compound P 42 Synthesis

[0069] ;

[0070] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 42 LC-MS (m / z)(Μ+): theoretical value is 951.34, measured value is 951.42.

[0071] Example 7: Compound P 59 Synthesis

[0072] ;

[0073] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 59 LC-MS (m / z)(Μ+): theoretical value is 707.31, and the measured value is 707.38.

[0074] Example 8: Compound P 63 Synthesis

[0075] ;

[0076] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 63 LC-MS (m / z)(Μ+): theoretical value is 859.36, measured value is 859.41.

[0077] Example 9: Compound P 84 Synthesis

[0078] ;

[0079] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 84LC-MS (m / z)(Μ+): theoretical value is 797.31, and the measured value is 797.61.

[0080] Example 10: Compound P 108 Synthesis

[0081] ;

[0082] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 108 LC-MS (m / z) (Μ+): theoretical value is 645.29, measured value is 645.71.

[0083] Example 11: Compound P 110 Synthesis

[0084] ;

[0085] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 110 LC-MS (m / z) (Μ+): theoretical value is 721.32, and the measured value is 721.45.

[0086] Example 12: Compound P 152 Synthesis

[0087] ;

[0088] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 152 LC-MS (m / z) (Μ+): theoretical value is 843.33, measured value is 843.66.

[0089] Example 13: Compound P 161 Synthesis

[0090] ;

[0091] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 161 LC-MS (m / z) (Μ+): theoretical value is 797.26, and the measured value is 797.36.

[0092] Example 14: Compound P 165 Synthesis

[0093] ;

[0094] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 165LC-MS (m / z) (Μ+): theoretical value is 807.33, measured value is 807.46.

[0095] Example 15: Compound P 169 Synthesis

[0096] ;

[0097] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 169 LC-MS (m / z) (Μ+): theoretical value is 767.30, measured value is 767.61.

[0098] Example 16: Compound P 218 Synthesis

[0099] ;

[0100] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 218 LC-MS (m / z) (Μ+): theoretical value is 883.36, measured value is 883.72.

[0101] Example 17: Compound P 223 Synthesis

[0102] ;

[0103] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 223 LC-MS (m / z) (Μ+): theoretical value is 837.29, measured value is 837.53.

[0104] Example 18: Compound P 233 Synthesis

[0105] ;

[0106] Reference Examples 1-2 Synthesis of Compound P Using the Synthesis Method and Synthesis Route of the Compounds 233 LC-MS (m / z) (Μ+): theoretical value is 919.36, measured value is 919.42.

[0107] Several examples of the application of the organic compounds of the present invention in OLED devices are listed below to further illustrate the beneficial effects of the compounds of the present invention. The materials used in the examples are purchased commercially or synthesized by themselves:

[0108] Fabrication of OLED devices:

[0109] As a reference preparation method for a device embodiment, the light-emitting device structure provided by the present invention is preferably: first, use an ultrasonic cleaner to wash the alkali-free glass substrate with isopropyl alcohol for 15 minutes, and then perform UV ozone cleaning in air for 30 minutes. The treated substrate is firstly evaporated with ITO / Ag / ITO 100nm as an anode by vacuum evaporation, and then the hole injection layer (HT:PD, 10nm), hole transport layer (HT, 120nm), luminescent auxiliary material (P1, 50nm), luminescent layer (compound H1-002: H2-003 (50:50), 27nm, and doping material GD, 3nm), electron transport layer (ET:Liq (50:50), 30nm), electron injection layer (Yb, 1nm) are sequentially stacked and evaporated, and Mg and Ag (weight ratio 10:1, 15nm) are co-evaporated to make a semi-transparent cathode, and then compound CPL (65nm) is evaporated as a covering layer. Finally, the light-emitting device was prepared by encapsulating with epoxy resin adhesive in a nitrogen atmosphere, which is recorded as Application Example 1.

[0110] Referring to the device structure provided in Application Example 1, the light-emitting auxiliary materials listed in Table 1 are selected as the implementation objects to replace compound P1 to prepare OLED light-emitting devices, which are recorded as Application Examples 2 to 18 and Comparative Example 1. The current efficiency, voltage, life and other characteristics of the device embodiments and comparative examples prepared above are tested by standard methods, and the device light-emitting characteristic data are shown in Table 1. The molecular structure formula of the relevant materials is as follows:

[0111]

[0112] As can be seen from Table 1, the compounds of the present invention have higher current efficiency and better lifespan after being prepared into electronic devices as luminescent auxiliary materials. Compared with Comparative Example 1, Application Examples 1 to 18 all show good device performance in terms of BI luminescent efficiency and lifespan, and the improvement in the performance of each device is achieved based on the better electron transmission ability of the specific compound materials of the present invention. This shows that the compounds provided by the present invention have certain commercial application value.

[0113] The above shows and describes the basic principles, main features and advantages of the present invention. Those skilled in the art should understand that the present invention is not limited to the above embodiments. The above embodiments and descriptions are only for explaining the principles of the present invention. The present invention may be subject to various changes and improvements without departing from the spirit and scope of the present invention. These changes and improvements fall within the scope of the present invention. The scope of protection of the present invention is defined by the attached claims and their equivalents.

Claims

1. An organic compound, characterized in that It has the structure shown in the following formula (I): In formula (I), Ar1 and Ar2 are each independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; L1 and L2 are each independently selected from a single bond, a C6-C30 aryl group; R1 and R2 are each independently selected from hydrogen, deuterium, C1-C30 alkyl, C6-C30 aryl, and R1 and R2 may be connected to form a ring; R3-R5 represent a multi-substituted group, which may be unsubstituted, monosubstituted or multi-substituted; each time R3 and R4 appear, they are independently selected from one or more of hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl; R3 and R4 may be connected to form a ring; the R5 is selected from hydrogen and deuterium; when there is substitution, the substituent is selected from one or more of hydrogen, deuterium, C1-C12 alkyl, C6-C18 aryl.

2. The organic compound according to claim 1, characterized in that In formula (I), Ar1 and Ar2 are independently selected from any one or more of phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl and terphenyl.

3. The organic compound according to claim 1, characterized in that In formula (I), L1 and L2 are independently selected from any one or more of a single bond, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

4. The organic compound according to claim 1, characterized in that R1 and R2 are each independently selected from hydrogen, deuterium, methyl, and phenyl; when R1 and R2 are both selected from phenyl, R1 and R2 can be connected to form a ring.

5. The organic compound according to claim 1, characterized in that The R3 and R4 are each independently selected from any one or more of hydrogen, deuterium, methyl, ethyl, isopropyl, and tert-butyl.

6. An organic compound, characterized in that The compound is selected from any one of the following chemical structures:

7. Use of the organic compound according to any one of claims 1 to 6 in the preparation of an organic electroluminescent device.

8. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises: a substrate layer; a first electrode, which is on the substrate; an organic light-emitting functional layer, which is on the first electrode; a second electrode, which is on the organic light-emitting functional layer; the organic light-emitting functional layer contains the organic compound described in any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer includes a light-emitting composition, and the light-emitting composition includes a compound having a structure represented by formula (II) and a compound having a structure represented by formula (III); In formula (II), Q1-Q2 are each independently selected from hydrogen, deuterium, and a C6-C30 aryl group; in formula (III), Q3-Q5 are each independently selected from hydrogen, deuterium, and a C6-C30 aryl group.

10. The organic electroluminescent device according to claim 9, characterized in that: Q1-Q2, Q3-Q5 are each independently selected from hydrogen, deuterium, phenyl, biphenyl or naphthyl.

11. The organic electroluminescent device according to claim 9, characterized in that: The luminescent composition comprises a compound having a structure represented by formula (II) and a compound having a structure represented by formula (III) in an equal proportion.

12. The organic electroluminescent device according to claim 9, characterized in that: The compound of the structure shown in formula (II) is selected from any one of the following chemical structures:

13. The organic electroluminescent device according to claim 9, characterized in that: The compound of the structure represented by formula (III) is selected from any one of the following chemical structures, wherein "D" represents deuterium:

14. Use of the organic electroluminescent device according to any one of claims 8 to 13 in a display or lighting device.

15. A display or lighting device, characterized in that: The device comprises the organic electroluminescent device according to any one of claims 8 to 13.

Citation Information

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