Organic electroluminescent compound, organic electroluminescent material containing double hosts and luminescent device

Abstract

The invention provides an organic electroluminescent compound, a double-host-containing organic electroluminescent material and a luminescent device.The organic electroluminescent compound has a structure as shown in a general formula (1), and the double-host-containing organic electroluminescent material comprises a first host material and a second host material, the first main body material is a compound with a structure shown in a general formula (1), the second main body material is a compound with a structure shown in a general formula (2), and the luminous efficiency and the service life of the device can be effectively improved by using the specific combination of the compounds as the main body material in the organic electroluminescent device.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials, specifically relating to an organic electroluminescent compound, an organic electroluminescent material containing two main components, and a light-emitting device. Background Technology

[0002] Organic electroluminescent devices are self-emissive devices that have attracted widespread attention in the panel display device industry due to their characteristics such as low driving voltage, high resolution, high brightness, fast response time, and flexibility, as well as the low production cost, easy processing, and high purity of raw materials.

[0003] Currently, OLED display technology has been applied in fields such as smartphones and tablets, and will be expanded to large-size applications such as televisions. However, compared with the requirements of actual product applications, the performance of OLED, such as luminous efficiency and lifespan, still needs to be further improved.

[0004] The luminescent material of an organic light-emitting diode (OLED) device is the most important factor determining the device's luminous efficiency. Functionally, it can be divided into host materials and dopant materials. The luminescent material can be used by mixing the host and dopants to improve color purity, luminous efficiency, and stability. Devices with excellent electroluminescence (EL) characteristics typically have a structure where a luminescent layer is formed by incorporating dopants into the host. When using such a dopant / host material system as the luminescent material, the host material significantly affects the efficiency and lifespan of the OLED device; therefore, selecting a suitable host material is crucial.

[0005] Therefore, the urgent task at present is to develop OLEDs with high efficiency and long lifespan. In particular, considering the EL characteristics required for medium and large OLED panels, it is imperative to develop luminescent materials that are superior to conventional luminescent materials and have excellent performance. Summary of the Invention

[0006] In view of the shortcomings of the prior art, the purpose of this invention is to provide an organic electroluminescent compound, an organic electroluminescent material containing a dual host, and a light-emitting device.

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

[0008] On the one hand, the present invention provides an organic electroluminescent compound having the structure shown in general formula (1):

[0009] ;

[0010] Where X and Y are each independently selected from -N=, -NR1-, -O- or -S-, and one of X and Y is -N= or -NR1-, and the other is -O- or -S-;

[0011] R1 is selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C group. 12 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups.

[0012] A is selected from substituted or unsubstituted phenyl groups and is fused with the adjacent benzene ring;

[0013] R is selected from substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C 12 -C 30 Aromatic amino groups, substituted or unsubstituted C 12 -C 30 The heteroaryl group is a monocyclic aromatic group or a polycyclic aromatic system comprising at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S or N;

[0014] L1 and L2 are each independently selected from the connecting bond, with or without substitution of C6-C. 30 β-C, substituted or unsubstituted C6-C 30 Heteroaryl, wherein the heteroaryl is a monocyclic aromatic group or a polycyclic aromatic system comprising at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S or N;

[0015] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C. 30 Aryl, substituted or unsubstituted C6-C 30 heteroaryl, substituted or unsubstituted C 10 -C 30 The fused ring group; its heteroaryl group is a monocyclic aromatic group or a polycyclic aromatic system including at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S, and N;

[0016] All hydrogen atoms in the general formula (1) can be completely unsubstituted by deuterium, completely substituted by deuterium, or partially substituted by deuterium.

[0017] Preferably, R1 is a methyl group.

[0018] Furthermore, R is selected from groups capable of being linked at any substituted site, or R is selected from deuterium-substituted groups:

[0019] .

[0020] L1-L3 are each independently selected from the linking bond, phenyl or naphthyl group.

[0021] Furthermore, the organic electroluminescent compound has the compound structures shown in I-1 to I-24:

[0022] .

[0023] According to one embodiment of the present invention, Ar1 and Ar2 are selected from the following groups or from the following groups substituted with deuterium, and are attached at any substituted site:

[0024] .

[0025] Furthermore, in this invention, "substituted or unsubstituted C6-C" 30 "Aryl", "substituted or unsubstituted C3-C" 30 "Heteroaryl", "substituted or unsubstituted C" 10 -C 30 The number of carbon atoms in "fused cyclic group" represents the number of carbon atoms constituting the unsubstituted aryl group, unsubstituted fused cyclic group, unsubstituted heterocyclic alkyl group, or the total number of carbon atoms constituting the heteroaryl group, without considering the number of carbon atoms in the substituents.

[0026] The term "substitution" means substitution by a substituent selected from the following: deuterium, cyano, methyl, tert-butyl, C6-C. 24 Aryl, C6-C 24 A heteroaryl group, wherein the heteroatom is one or a combination of at least two of O, S or N.

[0027] According to one embodiment of the present invention, the organic electroluminescent compound is selected from any one of H1-1 to H1-384:

[0028]

[0029]

[0030] .

[0031] The above are some specific structural forms of organic electroluminescent compounds, but are not limited to the chemical structures listed. All compounds with simple transformations of groups within the defined range based on the general structural formula shown in formula (1) should be included.

[0032] On the other hand, the present invention also provides an organic electroluminescent material containing two hosts, the organic electroluminescent material comprising a first host material and a second host material, wherein the first host material is an organic electroluminescent compound as described above; and the second host material is a compound having the structure shown in general formula (2):

[0033] ;

[0034] H1 to H3 are each independently selected from the linking bond, substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C6-C 30 Heteroaryl groups, wherein the heteroaryl group comprises a monocyclic aromatic group or a polycyclic aromatic system having at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S, N, P or Si;

[0035] D1 to D3 are each independently selected from substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C6-C 30 heteroaryl, substituted or unsubstituted C 10 -C 30 Fused ring group, substituted or unsubstituted C 18 -C 30 Phospho-oxygen, substituted or unsubstituted C 18 -C 30 Silyl groups; wherein the heteroaryl group comprises a monocyclic aromatic group or a polycyclic aromatic system with at least one heteroatom, the heteroatom being one or a combination of at least two of O, S, N, P or Si;

[0036] All hydrogen atoms in the general formula (2) can be completely unsubstituted by deuterium, completely substituted by deuterium, or partially substituted by deuterium.

[0037] According to one embodiment of the present invention, D1 is selected from the following groups or deuterated groups, wherein the connection position is at any substituted site:

[0038] .

[0039] Preferably, D2 and D3 are each independently selected from the following groups or deuterated groups, and are attached at any substituted site:

[0040] .

[0041] Preferably, H2 and H3 are each independently selected from the linking bond, phenyl, and naphthyl groups.

[0042] Preferably, H1 is selected from the linking bond, substituted or unsubstituted C6-C. 18 aryl, substituted or unsubstituted C6-C 18 A heteroaryl group comprising a monocyclic aromatic group or a polycyclic aromatic system containing at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S, N, P or Si.

[0043] Preferably, the "substitution" is selected from deuterium, cyano, methyl, tert-butyl, C6-C. 24 Aryl, C6-C 24 A heteroaryl group comprising a monocyclic aromatic group or a polycyclic aromatic system containing at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S, N, P or Si.

[0044] In this invention, the second body material has any one of the following structures, but is not limited thereto:

[0045]

[0046]

[0047]

[0048]

[0049] .

[0050] The above is the specific structural formula of the second main material. The present invention prefers the above structure but is not limited to it. All compounds based on the structure shown in general formula (2), with simple transformations of H1 to H3 and D1 to D3 groups within all ranges defined above, should be included.

[0051] This invention also provides a method for preparing an organic electroluminescent material containing two main bodies, specifically including methods for preparing the first main body material and the second main body material, the specific steps of which are as follows:

[0052] 1. The synthesis method of the first main material is as follows:

[0053] Raw material A (1 eq), raw material B (1-1.3 eq), and sodium tert-butoxide (2-3 eq) were added sequentially to a reaction vessel. Toluene was then added as the reaction solvent. Under nitrogen protection, catalysts Pd2(dba)3 (0.005-0.02 eq) and P(t-Bu)3 (tri-tert-butylphosphine, 0.01-0.04 eq) were added. The mixture was refluxed at 120-130°C for 16-28 hours under nitrogen protection, then cooled to 23-28°C. Pure water was added, and the mixture was stirred for 30-50 minutes. After standing and separating the layers, the mixture was separated and subjected to column chromatography to obtain the final product, general formula 1.

[0054] The reaction route is shown below, where Hal in raw material A can be arbitrarily and independently selected from Cl, Br, or I.

[0055]

[0056] 2. The synthesis of the second main material is as follows:

[0057] (1) Weigh reactant 1 (1 eq), reactant 2 (1-1.5 eq), and potassium carbonate (2-3 eq) and add them to the reaction vessel in sequence. Then add tetrahydrofuran and water as reaction solvents. Add catalyst Pd(PPh3)4 (tetra(triphenylphosphine)palladium, 0.01-0.03 eq) under nitrogen protection. Reflux at 70-90℃ for 16-28 hours under nitrogen protection. Then cool to 23-28℃, add pure water, stir for 30-50 minutes, let stand for layering, separate the liquid and liquid, and perform column chromatography to obtain intermediate 2-1.

[0058] (2) Weigh intermediate 2-1 (1 eq), reactant 3 (1-1.5 eq), and potassium carbonate (2-3 eq) and add them to the reaction vessel in sequence. Then add tetrahydrofuran and water as reaction solvents. Add catalyst Pd(PPh3)4 (0.01-0.03 eq) under nitrogen protection. Reflux at 70-90℃ for 16-28 hours under nitrogen protection. Then cool to 23-28℃, add pure water, stir for 30-50 minutes, let stand for layering, separate the liquid and liquid, and perform column chromatography to obtain the final product of general formula 2.

[0059]

[0060] The present invention also provides an organic electroluminescent device, which includes the organic electroluminescent compound as described above or the organic electroluminescent material containing a dual host as described above.

[0061] In one embodiment of the present invention, the organic electroluminescent device includes a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a second electrode arranged sequentially; the material of the light-emitting layer includes the organic electroluminescent compound as described above or the organic electroluminescent material containing a dual host as described above.

[0062] Preferably, the material of the light-emitting layer further includes a doped material.

[0063] Furthermore, in one embodiment of the present invention, the mass ratio of the organic electroluminescent material containing two main bodies to the doped material in the light-emitting layer is (5~199):1, for example 5:1, 10:1, 15:1, 20:1, 30:1, 35:1, 40:1, 45:1, 50:1, 60:1, 70:1, 80:1, 90:1, 100:1, 120:1, 140:1, 160:1, 180:1 or 199:1, preferably (5~100):1, more preferably (5~15):1.

[0064] In one embodiment of the present invention, the method for preparing the light-emitting layer includes, but is not limited to, forming the light-emitting layer from the organic electroluminescent material by solution coating and vacuum deposition; here, solution coating means spin coating, dip coating, inkjet printing, screen printing, spraying, etc., but is not limited thereto.

[0065] In one embodiment of the present invention, the first electrode is an anode.

[0066] As the anode material, a material with a high work function is preferred to facilitate the injection of holes into the organic layer. Anode materials usable in this invention include: metals, such as vanadium, chromium, copper, zinc, or their alloys; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO / Al or SnO2 / Sb; conductive polymers, such as poly(3-methylthiophene), polypyrrole, or polyaniline; but not limited thereto. In some embodiments of this invention, the anode is an ITO anode.

[0067] In one embodiment of the present invention, the material of the hole injection layer is selected from one or more of metalloporphyrin, oligothiophene, arylamine-based organic materials, benzonitrile-based organic materials, quinacridone-based organic materials, polyaniline-based and polythiophene-based conductive polymers.

[0068] The material of the hole injection layer is a material that receives holes from the anode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection layer material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.

[0069] In one embodiment of the present invention, the material of the hole transport layer is selected from one or more of arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions. The material of the hole transport layer is capable of receiving holes from the anode or hole injection layer and transporting the holes to the light-emitting layer, exhibiting high hole mobility.

[0070] In one embodiment of the present invention, the electron transport layer is selected from one or more of 8-hydroxyquinoline Al complexes, organic free radical compounds, but is not limited thereto.

[0071] In one embodiment of the present invention, the thickness of the electron transport layer is from 1 nm to 50 nm, for example, 1 nm, 2 nm, 4 nm, 6 nm, 8 nm, 10 nm, 15 nm, 20 nm, 25 nm, 30 nm, 35 nm, 40 nm, 45 nm, or 50 nm.

[0072] The electron transport layer prevents a decrease in electron transport characteristics and avoids an increase in driving voltage due to excessive thickness, thus promoting electron transport. The material of the electron transport layer is used to receive electrons from the cathode and transport them to the light-emitting layer, exhibiting high electron mobility.

[0073] In one embodiment of the present invention, the electron-injected layer is selected from one or more of fluorenone, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, imidazole, perylenetetracarboxylic acid, fluorenemethane, anthrone or its derivatives, metal complexes, and nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0074] The electron injection layer can promote electron injection, and the electron injection material preferably has the ability to transport electrons, has the electron injection effect from the cathode, has excellent electron injection effect on the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film forming ability.

[0075] In one embodiment of the present invention, the second electrode is a cathode.

[0076] As a cathode material, a material with a low work function is generally preferred to facilitate the injection of electrons into the organic layer. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, and other metals or alloys thereof; multilayer materials, such as LiF / Al or LiO2 / Al; but are not limited thereto. In some embodiments of the present invention, the cathode material is Al.

[0077] In one embodiment of the present invention, the organic electroluminescent device may be a top-emitting type, a bottom-emitting type, or a dual-sided emitting type.

[0078] The numerical range described in this invention includes not only the point values ​​listed above, but also any point values ​​within the numerical ranges not listed above. Due to space limitations and for the sake of brevity, this invention will not exhaustively list all the specific point values ​​included in the range.

[0079] Compared with the prior art, the present invention has the following beneficial effects:

[0080] The present invention provides an organic electroluminescent material containing two main bodies, wherein the organic electroluminescent material containing two main bodies includes a first main body material and a second main body material. The first main body material is a compound having the structure shown in general formula (1), and the second main body material is a compound having the structure shown in general formula (2). By using a specific combination of compounds as the main body material in an organic electroluminescent device, the luminous efficiency and service life of the device can be effectively improved.

[0081] Specifically, this invention employs a combination of a first host compound with a specific structure and a second host compound with a specific structure. The first host material is a molecule with a triarylamine backbone. This molecule, with a phenanthrenebenzoxazole / thiazole core structure, possesses a high glass transition temperature and molecular thermal stability. The compound also has a large conjugated system, thus significantly enhancing the hole transport capability and lifetime of the compound. Simultaneously, the second host compound, with a triazine structure, enhances both hole and electron transport capabilities. Therefore, when holes are injected into the p-type host and electrons are injected into the n-type host, the driving voltage is reduced while the lifetime is also enhanced. Attached Figure Description

[0082] Figure 1 The image shows the hydrogen nuclear magnetic resonance spectrum of compound H1-99 provided in the embodiments of the present invention. Detailed Implementation

[0083] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0084] Additionally, it should be noted that the values ​​given in the following embodiments are as accurate as possible; however, those skilled in the art will understand that due to unavoidable measurement errors and experimental issues, each number should be understood as an approximation rather than an absolutely accurate value.

[0085] The following are common knowledge references:

[0086] Organometallic Chemistry (6th Edition), Robert H. Crabtree, published by East China University of Science and Technology Press, Shanghai, September 00, 2017, ISBN: 978-7-5628-5111-0, page 388.

[0087] Organic Chemistry and Optoelectronic Materials Experiment Tutorial, Chen Runfeng, Publisher: Southeast University Press, Publication Date: 2019-11-00, ISBN: 9787564184230, Page 174.

[0088] The features and performance of the present invention will be further described in detail below with reference to specific embodiments.

[0089] Example 1: Preparation of the first host compound H1-99

[0090] (1) Raw materials H1-99-a (1 eq, CAS: 537025-33-5), H1-99-b (1 eq, CAS: 3033730-02-5), and potassium carbonate (2 eq) were added to the reactor and purged with nitrogen three times. A mixture of water and tetrahydrofuran was added as a solvent and purged with nitrogen three times. Pd(PPh3)4 (0.01 eq) was added and purged with nitrogen three times. The mixture was heated to 80 °C and reacted for 12 hours under nitrogen protection. After the reaction was completed, the mixture was cooled to room temperature. Then, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography to obtain intermediate H1-99-1 (yield 73%).

[0091] (2) Intermediate H1-99-1 (1 eq), (methoxymethyl)triphenylphosphine chloride (1.3 eq) and tetrahydrofuran were added to the reaction vessel and stirred at room temperature for 10 minutes. Potassium tert-butoxide solution was slowly added dropwise at 0 °C. Then the temperature was slowly increased and stirred at room temperature for 3 hours. Distilled water was added. After the reaction was completed, the organic layer was extracted with ethyl acetate and the organic phase was dried with sodium sulfate. The solvent was removed by rotary evaporator and purified by column chromatography to obtain compound intermediate H1-99-2 (yield 62%).

[0092] (3) The intermediate H1-99-2 (1 eq), boron trifluoride ether (0.15 eq) and dichloromethane were added to the reaction vessel and stirred at 25°C for 3 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and water, and then the organic layer was dried with sodium sulfate. The solvent was removed by rotary evaporator and purified by column chromatography to obtain the intermediate compound H1-99-3 (yield 57%).

[0093] (4) The intermediate compound H1-99-3 (1 eq), the starting material H1-99-c (1 eq, CAS: 1427556-45-3), and sodium tert-butoxide (2 eq) were added sequentially to a reaction vessel. Toluene was then added as the reaction solvent. Under nitrogen protection, catalysts Pd2(dba)3 (0.01 eq) and P(t-Bu)3 (0.02 eq) were added. The mixture was refluxed at 120°C for 24 hours under nitrogen protection, then cooled to 25°C. Pure water was added, and the mixture was stirred for 30 minutes. After standing and separating the layers, the mixture was separated and subjected to column chromatography to obtain the final product H1-99 (yield 71%, HPLC > 99%, mass spectrometry value 678.61, elemental analysis C, 86.63; H, 4.52; N, 4.19; O, 4.77). The proton NMR spectrum of H1-99 is shown below. Figure 1 As shown.

[0094]

[0095] Example 2: Preparation of the first host compound H1-174

[0096] (1) Raw materials H1-174-a (1 eq, CAS: 866332-17-4), H1-174-b (1 eq, CAS: 1331895-48-7), and potassium carbonate (2 eq) were added to the reactor and purged with nitrogen three times. A mixture of water and tetrahydrofuran was added as a solvent and purged with nitrogen three times. Pd(PPh3)4 (0.01 eq) was added and purged with nitrogen three times. The mixture was heated to 80 °C under nitrogen protection and reacted for 12 hours. After the reaction was completed, the mixture was cooled to room temperature. Then, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography to obtain intermediate H1-174-1 (yield 75%).

[0097] (2) Intermediate H1-174-1 (1 eq), (methoxymethyl)triphenylphosphine chloride (1.3 eq) and tetrahydrofuran were added to the reaction vessel and stirred at room temperature for 10 minutes. Potassium tert-butoxide solution was slowly added dropwise at 0 °C. Then the temperature was slowly increased and stirred at room temperature for 3 hours. Distilled water was added. After the reaction was completed, the organic layer was extracted with ethyl acetate and the organic phase was dried with sodium sulfate. The solvent was removed by rotary evaporator and purified by column chromatography to obtain intermediate H1-174-2 (yield 61%).

[0098] (3) The intermediate H1-174-2 (1 eq), boron trifluoride ether (0.15 eq) and dichloromethane were added to the reaction vessel and stirred at 25°C for 3 hours. After the reaction was completed, the organic layer was extracted with dichloromethane and water, and then the organic layer was dried with sodium sulfate. The solvent was removed by rotary evaporator and purified by column chromatography to obtain the intermediate compound H1-174-3 (yield 63%).

[0099] (4) The intermediate compound H1-174-3 (1 eq), the raw material H1-99-c (1 eq, CAS: 1427556-45-3), and sodium tert-butoxide (2 eq) were added sequentially into a reaction vessel. Toluene was then added as the reaction solvent. Under nitrogen protection, catalysts Pd2(dba)3 (0.01 eq) and P(t-Bu)3 (0.02 eq) were added. The mixture was refluxed at 120°C for 24 hours under nitrogen protection. Then, it was cooled to 25°C, purified water was added, and the mixture was stirred for 30 minutes. After standing and separating the layers, the mixture was separated and subjected to column chromatography to obtain the final product H1-174 (yield 75%, HPLC > 99%, mass spectrometry value 678.45, elemental analysis: C, 86.62; H, 4.53; N, 4.19; O, 4.77).

[0100]

[0101] Example 3: Preparation of the second host compound H2-1

[0102] The raw materials H2-1-a (1 eq, CAS: 1698859-04-9), H2-1-b (1 eq, CAS: 1883265-32-4), and potassium carbonate (2 eq) were added to a reactor. A mixture of water and tetrahydrofuran was added as a solvent. Under nitrogen protection, Pd(PPh3)4 (0.01 eq) was added, and the mixture was heated to 80 °C for 12 hours under nitrogen protection. After the reaction was completed, the mixture was cooled to room temperature. Subsequently, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography to obtain the final product H2-1 (yield 68%, HPLC > 99%, mass spectrometry value 549.55, elemental analysis: C, 85.12; H, 4.28; N, 7.72; O, 2.97).

[0103]

[0104] Example 4: Preparation of the second host compound H2-216

[0105] The raw materials H2-216-a (1 eq, CAS: 876442-90-9), H2-216-b (1 eq, CAS: 2418528-30-8), and potassium carbonate (2 eq) were added to a reactor. A mixture of water and tetrahydrofuran was added as a solvent. Under nitrogen protection, Pd(PPh3)4 (0.01 eq) was added, and the mixture was heated to 80°C for 12 hours under nitrogen protection. After the reaction was completed, the mixture was cooled to room temperature. Subsequently, the solvent was removed under reduced pressure, and the crude product was purified by column chromatography to obtain the final product H2-216 (yield 65%, HPLC > 99%, mass spectrometry value 575.43, elemental analysis: C, 85.46; H, 4.46; N, 7.37; O, 2.82).

[0106]

[0107] The other compounds were prepared using the same method as described above, and will not be repeated here.

[0108] Fabrication of organic electroluminescent devices

[0109] The fabrication method of organic electroluminescent devices is as follows:

[0110] (1) The ITO (indium tin oxide) glass substrate with a thickness of 1500 angstroms was washed twice with distilled water and ultrasonically washed for 30 minutes. Then it was washed twice with distilled water and ultrasonically washed for 10 minutes. After washing, it was ultrasonically washed sequentially with methanol, acetone and isopropanol (5 minutes each time), dried, and then transferred to a plasma cleaner for 5 minutes to obtain the ITO anode.

[0111] (2) In the vapor deposition machine, HIL is vacuum vapor deposited on the ITO anode surface obtained in step (1) with a thickness of 700 angstroms to obtain a hole injection layer.

[0112] (3) HTL is vacuum-deposited on the surface of the hole injection layer obtained in step (2) with a thickness of 750 angstroms to form a hole transport layer.

[0113] (4) The light-emitting layer material is deposited on the surface of the hole transport layer obtained in step (3) by linear gradient co-evaporation using a multi-source co-evaporation method, with a thickness of 300 angstroms, to obtain the light-emitting layer. The light-emitting layer material includes a dual host material and a dopant material. The mass ratio of the first host compound and the second host compound in the dual host material is 60:40, and the mass ratio of the dual host material to the dopant material is 10:1. The dual host materials are the host materials provided in device examples 1-36, comparative examples 1-10, and parallel comparative examples 1-8, respectively.

[0114] (5) HBL is deposited on the surface of the light-emitting layer obtained in step (4) with a thickness of 100 angstroms to form a hole blocking layer.

[0115] (6) Vacuum vapor deposition of ETL on the surface of the hole blocking layer obtained in step (5) with a thickness of 300 angstroms is obtained to obtain the electron transport layer.

[0116] (7) A Liq (EIL) layer with a thickness of 15 angstroms is vacuum-deposited on the surface of the electron transport layer obtained in step (6) to obtain an electron injection layer.

[0117] (8) A 1200 angstrom layer of Al is deposited on the surface of the electron injection layer obtained in step (7) to form a cathode, thereby obtaining the organic electroluminescent device.

[0118] Materials used in each functional layer of the device:

[0119] .

[0120] Device Examples 1-125, Comparative Examples 1-10, and Parallel Comparative Examples 1-8:

[0121] Device Examples 1-125 employ the dual host material of the present invention. The combination of the dual host materials is shown in Table 1. For the dual host material scheme including a compound of the first host material and a compound of the second host material, the mass ratio of the compound of the first host material and the compound of the second host material is 60:40.

[0122] Comparative Examples 1-10 use a compound with the structure shown in E or general formula (2) as a single host material.

[0123] In parallel comparative examples 1-8, a host material compound with the structure shown in general formula (2) of the present invention and a compound with the structure shown in E are respectively used for cross-matching.

[0124] In Table 1, "-" indicates that the compound is not present in the host material; the structure of E is shown below.

[0125] .

[0126] The driving voltage, luminous efficiency, and time (lifetime; T95) of the organic electroluminescent device at a brightness of 2500 nits were tested. The test results are shown in Table 1.

[0127] Table 1

[0128]

[0129] As can be seen from device examples 1-125, when the main material of the light-emitting layer is compounded with the compound of the first main material and the compound of the second main material of the present invention, its application in the device can significantly improve the luminous efficiency and service life.

[0130] A comparison of the device performance of Device Examples 1-125 and Parallel Comparative Examples 1-8 shows that the organic electroluminescent devices prepared in Parallel Comparative Examples 1-8 have an efficiency of 21.01-21.97 cd / A, a driving voltage of 3.32-3.50 V, and a lifetime of 811-839 h. In contrast, the organic electroluminescent devices prepared using dual host materials in Device Examples 1-125 of the present invention have a luminous efficiency of 30.01-33.26 cd / A, which is significantly higher than that of the devices in Parallel Comparative Examples 1-8. The driving voltage of Device Examples 1-125 of the present invention is 3.05-3.18 V, which is significantly lower than that of the devices in Parallel Comparative Examples 1-8. The lifetime of the devices in Device Examples 1-125 of the present invention is 1098-1510 h, which is much longer than that of the devices in Parallel Comparative Examples 1-8.

[0131] The organic compound structure of this invention uses phenanthrene-oxazole / thiazolylbenzene as the parent core structure. This parent core has a large conjugated system, which, after being linked with the triarylamine structure, enhances intermolecular forces and improves the charge carrier mobility of the compound. Compared with the other parent core structures in the comparative examples, this parent core has better steric hindrance, allowing molecules to form a good stacking structure in the thin film, enhancing intermolecular π-π interactions, promoting charge transport, and the benzene ring in the parent core has a greater degree of fusion, resulting in stronger thermal stability, which helps to improve device efficiency and lifetime. Mixing the compound of this invention with electron transport materials can form a hybrid host material, which can improve the charge carrier balance in the light-emitting layer, widen the charge carrier recombination region, improve exciton generation and utilization efficiency, and improve device luminous efficiency and lifetime.

[0132] The applicant declares that the present invention is illustrated through the above embodiments to describe the organic electroluminescent compound, the organic electroluminescent material containing two main components, and the light-emitting device of the present invention. However, the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above process steps to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials used in the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic electroluminescent compound, characterized in that, The organic electroluminescent compound has the structure shown in general formula (1): ； Where X and Y are each independently selected from -N=, -NR1-, -O- or -S-, and one of X and Y is -N= or -NR1-, and the other is -O- or -S-; R1 is selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C group. 12 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups. A is selected from substituted or unsubstituted phenyl groups and is fused with the adjacent benzene ring; R is selected from substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl, substituted or unsubstituted C 12 -C 30 Aromatic amino groups, substituted or unsubstituted C 12 -C 30 The heteroaryl group is a monocyclic aromatic group or a polycyclic aromatic system comprising at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S or N; L1 and L2 are each independently selected from the connecting bond, with or without substitution of C6-C. 30 β-C, substituted or unsubstituted C6-C 30 Heteroaryl, wherein the heteroaryl is a monocyclic aromatic group or a polycyclic aromatic system comprising at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S or N; Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C. 30 Aryl, substituted or unsubstituted C6-C 30 heteroaryl, substituted or unsubstituted C 10 -C 30 The fused ring group; its heteroaryl group is a monocyclic aromatic group or a polycyclic aromatic system including at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S, and N; All hydrogen atoms in the general formula (1) can be completely unsubstituted by deuterium, completely substituted by deuterium, or partially substituted by deuterium.

2. The organic electroluminescent compound according to claim 1, characterized in that, R1 is a methyl group; R is selected from the following groups, which can be linked at any substituted site, or R is selected from the following deuterated groups: ； L1-L3 are each independently selected from the linking bond, phenyl or naphthyl group.

3. The organic electroluminescent compound according to claim 1, characterized in that, The organic electroluminescent compound has the compound structures shown in I-1 to I-24: 。 4. The organic electroluminescent compound according to claim 1, characterized in that, The Ar1 and Ar2 are selected from the following groups or from the following groups substituted with deuterium, and are attached at any substituted site: 。 5. The organic electroluminescent compound according to claim 1, characterized in that, The term "substitution" means substitution by a substituent selected from the following: deuterium, cyano, methyl, tert-butyl, C6-C. 24 Aryl, C6-C 24 A heteroaryl group, wherein the heteroatom is one or a combination of at least two of O, S or N.

6. The organic electroluminescent compound according to claim 1, characterized in that, The organic electroluminescent compound is selected from any one of H1-1 to H1-384: 。 7. An organic electroluminescent material containing two main components, characterized in that, The organic electroluminescent material comprises a first host material and a second host material, wherein the first host material is an organic electroluminescent compound according to any one of claims 1-6; and the second host material is a compound having the structure shown in general formula (2): ； H1 to H3 are each independently selected from the linking bond, substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C6-C 30 Heteroaryl groups, wherein the heteroaryl group comprises a monocyclic aromatic group or a polycyclic aromatic system having at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S, N, P or Si; D1 to D3 are each independently selected from substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C6-C 30 heteroaryl, substituted or unsubstituted C 10 -C 30 Fused ring group, substituted or unsubstituted C 18 -C 30 Phospho-oxygen, substituted or unsubstituted C 18 -C 30 Silyl groups; wherein the heteroaryl group comprises a monocyclic aromatic group or a polycyclic aromatic system with at least one heteroatom, the heteroatom being one or a combination of at least two of O, S, N, P or Si; All hydrogen atoms in the general formula (2) are either completely unsubstituted by deuterium, completely substituted by deuterium, or partially substituted by deuterium.

8. The organic electroluminescent material containing two main bodies according to claim 7, characterized in that, D1 is selected from the following groups or deuterated groups, and its attachment position is at any substituted site: ； D2 and D3 are each independently selected from the following groups or deuterated groups, and are attached at any substituted site: ； H2 and H3 are each independently selected from the linking bond, phenyl, and naphthyl groups; H1 is selected from the linker, substituted or unsubstituted C6-C. 18 aryl, substituted or unsubstituted C6-C 18 Heteroaryl groups, wherein the heteroaryl group comprises a monocyclic aromatic group or a polycyclic aromatic system having at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S, N, P or Si; Preferably, the "substitution" is selected from deuterium, cyano, methyl, tert-butyl, C6-C. 24 Aryl, C6-C 24 A heteroaryl group comprising a monocyclic aromatic group or a polycyclic aromatic system containing at least one heteroatom, wherein the heteroatom is one or a combination of at least two of O, S, N, P or Si.

9. The organic electroluminescent material containing two main bodies according to claim 7, characterized in that, The second main material has any one of the following structures: 。 10. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises the organic electroluminescent compound of any one of claims 1-6 or the organic electroluminescent material containing a dual host of any one of claims 7-9; Preferably, the organic electroluminescent device comprises a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a second electrode arranged sequentially; the material of the light-emitting layer comprises the organic electroluminescent compound of any one of claims 1-6 or the organic electroluminescent material containing a dual host of any one of claims 7-9; Preferably, the material of the light-emitting layer further includes a doped material; the mass ratio of the organic electroluminescent material containing two main bodies to the doped material in the light-emitting layer is (5~199):1.

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