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

Abstract

The present invention belongs to the technical field of organic electroluminescent materials, and provides an organic electroluminescent compound, an organic electroluminescent material containing double hosts, and an organic electroluminescent device. The organic electroluminescent material comprises an organic electroluminescent compound LA and an organic electroluminescent compound LB, the mass ratio of LA to LB being 1:99-99:1, and the general structure formulas of LA and LB being shown in the description. The organic electroluminescent device of the present invention is manufactured by means of a specific heterocycle combination and deuteration at specific positions and thus has obviously reduced driving voltage, remarkably improved current efficiency and remarkably prolonged service life.

Description

Organic electroluminescent compound, organic electroluminescent material containing dual hosts, and organic electroluminescent device

[0001] The present disclosure claims the priority benefit of the applicant's prior application filed with the State Intellectual Property Office of China on January 18, 2024, with patent application number 2024100720186, entitled "Organic electroluminescent compounds, organic electroluminescent materials containing dual hosts, and organic electroluminescent devices"; the full text of the prior application is incorporated into the disclosure by reference. Technical Field

[0002] The present invention belongs to the field of organic electroluminescent materials, and in particular relates to an organic electroluminescent material containing a dual-host organic electroluminescent compound and an organic electroluminescent device containing the same. Background Art

[0003] Organic electroluminescence technology is the latest generation of flat-panel display technology. Among organic luminescence, phosphorescence has been highly sought after since its discovery. This is because the luminous efficiency of phosphorescent materials is significantly higher than that of fluorescent materials, and theoretically can reach 100%. Therefore, many scientific research institutions are increasing their research and development efforts in phosphorescent materials, attempting to accelerate industrial development through phosphorescent materials. For long-term use and high-resolution displays, OLEDs with high luminous efficiency and / or long life are required.

[0004] However, existing phosphorescent materials used in organic light-emitting devices suffer from low efficiency and short lifespan. Therefore, how to provide an organic electroluminescent material with long lifespan, high efficiency, and low driving voltage is an urgent problem to be solved by those skilled in the art. Summary of the Invention

[0005] In view of this, the present invention provides an organic electroluminescent material containing a dual host and an organic electroluminescent device containing the same. The organic electroluminescent material containing a dual host described in the present invention is applied to a specific light-emitting device, which has low driving voltage, high luminous efficiency and long service life.

[0006] It should be noted that the present invention provides an organic electroluminescent device with a dual-host structure. The light-emitting device is made by a specific heterocyclic combination and deuteration at a specific position. Not only is the driving voltage significantly reduced, but the current efficiency and life are also significantly improved.

[0007] In order to achieve the above object, the present invention adopts the following technical solutions:

[0008] The first technical purpose of the present invention is to provide an organic electroluminescent compound, which is represented by the following formula LA:

[0009] in:

[0010] f and n are both integers, f+n=1;

[0011] Ar1 is

[0012] R4, R5, R6, R7, and R8 are all D;

[0013] Ar2 and Ar3 are independently selected from:

[0014] R1, R2, R3, Ar4, Ar5, Ar6 and Ar7 are independently selected from C6-C30 aryl groups, C4-C20 heteroaryl groups and combinations thereof; the aryl group is selected from substituted and unsubstituted benzene, naphthalene, anthracene, phenanthrene, biphenyl, terphenyl, quaterphenyl, fluorene, diphenylfluorene and dibenzofluorene; the heteroaryl group is selected from substituted and unsubstituted pyridine, dibenzofuran, dibenzothiophene, quinoline, carbazole, benzonaphthofuran, benzonaphthothiophene, quinoxaline, quinazoline, benzocarbazole and dibenzocarbazole; the substituents in the aryl and heteroaryl groups are D, F or phenyl groups; when substituted by phenyl groups, the phenyl groups may be fused with adjacent groups to form a ring.

[0015] Furthermore, the organic electroluminescent compound LA is selected from any one of the following structures:

[0016] The second technical purpose of the present invention is to provide a dual-host organic electroluminescent material, wherein the dual-host organic electroluminescent material comprises the organic electroluminescent compound LA and the organic electroluminescent compound LB as described above, and the mass ratio of LA to LB is 1:99-99:1.

[0017] The structural formula of LB is as follows:

[0018] Wherein, La, Lb, Lc, X1, X2 and X3 are selected from single bonds, substituted and unsubstituted C6-C30 aryl groups, substituted and unsubstituted C4-C20 heteroaryl groups, the heteroatom in the heteroaryl group is O, S or N, and the substituents of the aryl and heteroaryl groups are D, F or phenyl.

[0019] Furthermore, the organic electroluminescent compound LB is selected from any one of the following structures:

[0020] The third technical purpose of the present invention is to provide an organic electroluminescent device.

[0021] The organic electroluminescent device comprises a first electrode, a second electrode, and an organic electroluminescent material layer disposed between the first electrode and the second electrode; the organic electroluminescent material layer comprises a light-emitting layer; the light-emitting layer comprises a dopant material and a host material, and the host material comprises the dual-host organic electroluminescent material described above;

[0022] Wherein, the mass ratio of the main material to the doping material is 5-99.5:1.

[0023] It can be seen from the above technical solutions that compared with the prior art, the present invention has the following beneficial effects:

[0024] The light-emitting device of the present invention, which is made by a specific heterocyclic combination and deuteration at a specific position, not only significantly reduces the driving voltage, but also significantly improves the current efficiency and lifespan; specifically,

[0025] 1. In the present invention, the phenyl hydrogen of the connected benzene in the specific heterocycle is cationized to reduce the breakage of the CH bond, and the amorphous film formed after deuteration is better. The triarylamine-type main material formed by the deuterated benzene and the N is connected to form a triarylamine-type main material. The triarylamine-type main material has a more suitable spatial structure than the main structure containing a double triarylamine structure, and has better hole transport ability. The driving voltage of the light-emitting device made with the N-type triarylamine structure is significantly reduced, and the current efficiency and life are significantly improved.

[0026] 2. In the present invention, the compound formed by the specific combination of O and N heterocycles is more stable than the compound formed by the combination of S and N heterocycles. The driving voltage of the light-emitting device made of the compound of the present invention is significantly reduced, and the current efficiency and life are significantly improved.

[0027] 3. The first host LA of the present invention is combined with the second host LB containing a triazine structure to form a host material. The first host LA has a strong hole transport capability, and the second host LB has a strong electron transport capability. This allows for higher recombination efficiency of holes and electrons in the light-emitting layer, significantly reducing the driving voltage of the light-emitting device and significantly improving the current efficiency and lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the following briefly introduces the drawings required for use in the embodiments or the description of the prior art. Obviously, the drawings described below are merely embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on the provided drawings without paying any creative work.

[0029] FIG1 is a mass spectrum of LA-002 of the present invention.

[0030] FIG2 is a hydrogen nuclear magnetic resonance spectrum of LA-002 of the present invention.

[0031] FIG3 is a mass spectrum of LA-006 of the present invention

[0032] FIG4 is a hydrogen nuclear magnetic resonance spectrum of LA-006 of the present invention.

[0033] FIG5 is a mass spectrum of LA-019 of the present invention.

[0034] FIG6 is a hydrogen nuclear magnetic resonance spectrum of LA-019 of the present invention

[0035] FIG7 is a mass spectrum of LA-020 of the present invention.

[0036] FIG8 is a hydrogen nuclear magnetic resonance spectrum of LA-020 of the present invention.

[0037] FIG9 is a mass spectrum of LA-021 of the present invention.

[0038] FIG10 is a hydrogen nuclear magnetic resonance spectrum of LA-021 of the present invention

[0039] Figure 11 is a mass spectrum of LA-023 of the present invention

[0040] FIG12 is a hydrogen nuclear magnetic resonance spectrum of LA-023 of the present invention DETAILED DESCRIPTION

[0041] The following is a clear and complete description of the technical solutions in the embodiments of the present invention. Obviously, the embodiments described are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making any creative efforts are within the scope of protection of the present invention.

[0042] The embodiment of the present invention discloses a method for preparing an organic electroluminescent material containing two hosts.

[0043] In addition, it should be noted that the numerical values ​​given in the following examples are as accurate as possible, but those skilled in the art understand that due to unavoidable measurement errors and experimental operation problems, each number should be understood as an approximate number rather than an absolutely accurate value.

[0044] Example 1 Preparation of Compound LA-002

[0045] 1) Preparation of compound 1-1

[0046] Under nitrogen protection, 2-amino-6-bromophenol (compound A) (159.56 mmol) (CAS: 28165-50-6), benzaldehyde-D6 (191.47 mmol) (CAS: 17901-93-8) and sodium cyanide (159.56 mmol) (CAS: 143-33-9) were added sequentially to a 1000 ml three-necked reaction flask and dissolved in 600 ml of N, N-dimethylformamide solvent. The mixture was reacted in an oil bath at 100 ° C for 6 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. Then, compound 1-1 (26.0 g, yield 58.4%) was purified by column chromatography.

[0047] 2) Preparation of compound 1-2

[0048] Under nitrogen protection, compound 1-1 (82.39 mmol), 4-chloro-2-formylphenylboronic acid (90.76 mmol) (CAS: 913835-76-4), tetrakis(triphenylphosphine)palladium (3.28 mmol), and sodium carbonate (205.98 mmol) were added in sequence to a 1000 ml three-necked reaction flask and dissolved in a mixed solvent of toluene (500 ml), EtOH (125 ml) and pure water (125 ml). The mixture was reacted in an oil bath at 140 ° C for 5 hours, and a precipitated solid was precipitated. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the precipitated solid product was washed with pure water and methanol to obtain compound 1-2 (19.5 g, yield 69.9%).

[0049] 3) Preparation of Compound 1-3

[0050] Under nitrogen protection, compound 1-2 (47.23 mmol) and (methoxymethyl)triphenylphosphine chloride (70.89 mmol) (CAS: 4009-98-7) were dissolved in tetrahydrofuran (500 ml) solvent, and the reaction mixture was stirred for 10 min. The reaction solution was cooled to 0°C, and potassium tert-butoxide was slowly added. After completion, it was stirred for 30 min, and the temperature was raised to room temperature and stirred for another 3 hours. After the reaction was completed by TLC monitoring, pure water was added to the reaction solution to terminate the reaction. The reaction solution was extracted with ethyl acetate, and the extracted organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporator, the organic phase was concentrated, and then purified by column chromatography to obtain compound 1-3 (15.1 g, yield 87.1%).

[0051] 4) Preparation of Compound 1-4

[0052] Under nitrogen protection, compound 1-3 (39.8 mmol) and Eaton's reagent (1.4 ml) (CAS: 39394-84-8) were dissolved in chlorobenzene (200 ml) solvent and reacted in an 80°C oil bath for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and the reaction liquid was extracted with dichloromethane. The extracted organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by a rotary evaporator. The organic phase was concentrated and then purified by column chromatography to obtain compound 1-4 (10.6 g, yield 79.5%).

[0053] 5) Preparation of compound LA-002

[0054] Under nitrogen protection, compound 1-4 (14.93 mmol), N-phenyl-4-benzidine (14.93 mmol) (CAS: 32228-99-2), tris(dibenzylideneacetone)dipalladium (0.75 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (1.493 mmol), and sodium tert-butoxide (30.0 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-002 product (4.2 g, yield 51.7%).

[0055] The mass spectrum is shown in Figure 1 , and the hydrogen nuclear magnetic resonance spectrum is shown in Figure 2 .

[0056] Example 2 Preparation of Compound LA-006

[0057] 1) Preparation of compound 2-1

[0058] Under nitrogen protection, 3-bromoisoquinoline (144.19 mmol), (4-(phenylamino)phenyl)boric acid (158.61 mmol) (CAS: 1228183-40-1), tetrakis(triphenylphosphine)palladium (5.74 mmol), and sodium carbonate (360.48 mmol) were added in sequence to a 1000 ml three-necked reaction flask and dissolved in a mixed solvent of toluene (500 ml), EtOH (125 ml) and pure water (125 ml). The reaction was carried out in an oil bath at 140 ° C for 6 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. Then, it was purified by column chromatography to obtain compound 2-1 (19.9 g, yield 66.3%).

[0059] 2) Preparation of compound LA-006

[0060] Under nitrogen protection, compound 2-1 (59.74 mmol), compound 1-4 (59.74 mmol), tris(dibenzylideneacetone)dipalladium (3.0 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (5.974 mmol), and sodium tert-butoxide (120.0 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-006 product (20.1 g, yield 56.6%).

[0061] The mass spectrum is shown in FIG3 , and the H NMR spectrum is shown in FIG4 .

[0062] Example 3 Preparation of Compound LA-019

[0063] Under nitrogen protection, N-([[1,1'-biphenyl]-3-yl]dibenzo[B,D]thiophene-3-amine (59.74 mmol) (CAS: 1923735-65-2), compound 1-4 (59.74 mmol), tris(dibenzylideneacetone)dipalladium (3.0 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (5.974 mmol), and sodium tert-butoxide (120.0 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-019 product (23.6 g, yield 60.8%).

[0064] The mass spectrum is shown in FIG5 , and the H NMR spectrum is shown in FIG6 .

[0065] Example 4 Preparation of Compound LA-020

[0066] Under nitrogen protection, N-([1,1'-biphenyl]-3-yl)dibenzo[b,d]furan-3-amine (59.74mmol) (CAS: 1427556-46-3), compound 1-4 (59.74mmol), tris(dibenzylideneacetone)dipalladium (3.0mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (5.974mmol), and sodium tert-butoxide (120.0mmol) were dissolved in o-xylene (100ml) solvent and reacted in an oil bath at 170°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-020 product (24.1g, yield 63.7%).

[0067] The mass spectrum is shown in FIG7 , and the H NMR spectrum is shown in FIG8 .

[0068] Example 5 Preparation of Compound LA-021

[0069] 1) Preparation of compound 3-1

[0070] Under nitrogen protection, 3-bromo-1.1`:2`,1"-terphenyl (64.68 mmol) (CAS: 1222633-95-5), 3-aminodibenzofuran (64.68 mmol) (CAS: 4106-66-5), tris(dibenzylideneacetone)dipalladium (1.3 mmol), tri-tert-butylphosphine (25.87 mmol), and sodium tert-butoxide (161.7 mmol) were added to a 500 ml three-necked reaction flask in sequence and dissolved in toluene (500 ml) solvent. The mixture was reacted in an oil bath at 60 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. Then, compound 3-1 (22.9 g, yield 86.0%) was purified by column chromatography.

[0071] 2) Preparation of compound LA-021

[0072] Under nitrogen protection, compound 3-1 (48.60 mmol), compound 1-4 (48.60 mmol), tris(dibenzylideneacetone)dipalladium (2.4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (0.486 mmol), and sodium tert-butoxide (97.6 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-021 product (17.5 g, yield 50.7%).

[0073] The mass spectrum is shown in FIG9 , and the H NMR spectrum is shown in FIG10 .

[0074] Example 6 Preparation of Compound LA-023

[0075] 1) Preparation of compound 4-4

[0076] Compound 4-4 was prepared in the same manner as described for compound 1-4, except that 4-chloro-2-formylphenylboronic acid was replaced by 5-chloro-2-formylphenylboronic acid, and the reaction molar ratios of other raw materials were the same.

[0077] 2) Preparation of compound LA-023

[0078] Under nitrogen, compound 4-4 (14.93 mmol), N-([1,1'-biphenyl]-3-yl)-[1,1':3',1'-triphenyl]-4-amine (14.93 mmol) (CAS: 1609484-77-6), tris(dibenzylideneacetone)dipalladium (0.75 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (1.493 mmol), and sodium tert-butoxide (30.0 mmol) were dissolved in o-xylene (100 ml). The mixture was reacted in an oil bath at 170°C for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature and then added dropwise to methanol to precipitate a solid, which was filtered to obtain the product LA-023 (6.7 g, 64.5% yield). Mass spectrum: calculated value: 695.88; assay value: 695.82.

[0079] The mass spectrum is shown in FIG11 , and the H NMR spectrum is shown in FIG12 .

[0080] Example 7 Preparation of Compound LA-028

[0081] The difference from Example 5 is that 3-bromo-1.1`:2`,1"-terphenyl is replaced by 4'-bromo-1,1':2',1"-terphenyl (CAS: 24253-40-5), compound 1-4 is replaced by 4-4, and the other components and synthesis conditions remain unchanged to obtain LA-028 product (21.2 g, yield 61.4%).

[0082] Mass spectrum: calculated value 709.86; tested value 709.88.

[0083] Example 8 Preparation of Compound LA-029

[0084] 1) Preparation of compound 6-1

[0085] Under nitrogen protection, 3-bromobenzo[B]naphtho[2,3-D]furan (64.68 mmol) (CAS: 1256544-32-7), 3-aminobiphenyl (64.68 mmol) (CAS: 2243-47-2), tris(dibenzylideneacetone)dipalladium (1.3 mmol), tri-tert-butylphosphine (25.87 mmol), and sodium tert-butoxide (161.7 mmol) were added to a 500 ml three-necked reaction flask in sequence and dissolved in toluene (500 ml) solvent. The mixture was reacted in an oil bath at 60 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. Then, compound 6-1 (16.8 g, yield 67.4%) was purified by column chromatography.

[0086] 2) Preparation of compound LA-029

[0087] Under nitrogen protection, compound 6-1 (48.60 mmol), compound 4-4 (48.60 mmol), tris(dibenzylideneacetone)dipalladium (2.4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (0.486 mmol), and sodium tert-butoxide (97.6 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170 ° C for 3 hours. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-029 product (17.5 g, yield 52.7%).

[0088] Mass spectrum: calculated value 683.82; tested value 683.81.

[0089] Example 9 Preparation of Compound LA-031

[0090] The difference from Example 8 is that 3-bromobenzo[B]naphtho[2,3-D]furan is replaced by 3-bromobenzo[B]naphtho[2,3-D]thiophene (CAS: 2189692-44-0), and the other components and synthesis conditions remain unchanged to obtain LA-031 product (16.9 g, yield 49.9%).

[0091] Mass spectrum: calculated value 699.88; tested value 699.79.

[0092] Example 10 Preparation of Compound LA-033

[0093] Under nitrogen protection, N-(4-(-1-naphthyl)phenyl)-4-benzidine (59.74mmol) (CAS: 897921-59-4), compound 4-4 (59.74mmol), tris(dibenzylideneacetone)dipalladium (3.0mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (5.974mmol), and sodium tert-butoxide (120.0mmol) were dissolved in o-xylene (100ml) solvent and reacted in an oil bath at 170°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-033 product (27.3g, yield 68.2%).

[0094] Mass spectrum: calculated value 669.84; tested value 669.91.

[0095] Example 11 Preparation of Compound LA-058

[0096] 1) Preparation of compound 8-1

[0097] Under nitrogen protection, 9-(4-bromophenyl)carbazole (64.68mmol) (CAS: 57102-42-8), 3-aminobiphenyl (64.68mmol) (CAS: 2243-47-2), tris(dibenzylideneacetone)dipalladium (1.3mmol), tri-tert-butylphosphine (25.87mmol), and sodium tert-butoxide (161.7mmol) were added sequentially to a 500ml three-necked reaction flask and dissolved in toluene (500ml) solvent. The mixture was reacted in an oil bath at 60°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. The mixture was then purified by column chromatography to obtain compound 8-1 (18.5g, yield 69.7%).

[0098] 2) Preparation of compound LA-058

[0099] Under nitrogen protection, compound 8-1 (48.60 mmol), compound 1-4 (48.60 mmol), tris(dibenzylideneacetone)dipalladium (2.4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (0.486 mmol), and sodium tert-butoxide (97.6 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-058 product (26.8 g, yield 77.8%).

[0100] Mass spectrum: calculated value 708.88; tested value 708.91.

[0101] Example 12 Preparation of Compound LA-060

[0102] 1) Preparation of compound 9-1

[0103] Under nitrogen protection, 2-(4-bromophenyl)pyridine (64.68 mmol) (CAS: 63996-36-1), 3-aminobiphenyl (64.68 mmol) (CAS: 2243-47-2), tris(dibenzylideneacetone)dipalladium (1.3 mmol), tri-tert-butylphosphine (25.87 mmol), and sodium tert-butoxide (161.7 mmol) were added sequentially to a 500 ml three-necked reaction flask and dissolved in toluene (500 ml) solvent. The mixture was reacted in an oil bath at 60°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. The mixture was then purified by column chromatography to obtain compound 9-1 (17.1 g, yield 82.0%).

[0104] 2) Preparation of compound LA-060

[0105] Under nitrogen protection, compound 9-1 (48.60 mmol), compound 1-4 (48.60 mmol), tris(dibenzylideneacetone)dipalladium (2.4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (0.486 mmol), and sodium tert-butoxide (97.6 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-060 product (26.3 g, yield 87.2%).

[0106] Mass spectrum: calculated value 620.77; tested value 620.73.

[0107] Example 13 Preparation of Compound LA-079

[0108] 1) Preparation of compound 10-1

[0109] Under nitrogen protection, 2-bromo-9-phenyl-9H-carbazole (64.68 mmol) (CAS: 94994-62-4), 3-aminobiphenyl (64.68 mmol) (CAS: 2243-47-2), tris(dibenzylideneacetone)dipalladium (1.3 mmol), tri-tert-butylphosphine (25.87 mmol), and sodium tert-butoxide (161.7 mmol) were added sequentially to a 500 ml three-necked reaction flask and dissolved in toluene (500 ml) solvent. The mixture was reacted in an oil bath at 60° C. for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. The mixture was then purified by column chromatography to obtain compound 10-1 (18.2 g, yield 52.8%).

[0110] 2) Preparation of compound LA-079

[0111] Under nitrogen protection, compound 10-1 (48.60 mmol), compound 4-4 (48.60 mmol), tris(dibenzylideneacetone)dipalladium (2.4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (0.486 mmol), and sodium tert-butoxide (97.6 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-079 product (27.1 g, yield 78.7%).

[0112] Mass spectrum: calculated value 708.88; tested value 708.92.

[0113] Example 14 Preparation of Compound LA-081

[0114] Under nitrogen, N-[1,1'-biphenyl-3-yl]-9,9-dimethyl-9H-fluoren-2-amine (59.74 mmol) (CAS: 1372778-66-9), compound 4-4 (59.74 mmol), tris(dibenzylideneacetone)dipalladium (3.0 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (5.974 mmol), and sodium tert-butoxide (120.0 mmol) were dissolved in o-xylene (100 ml) and reacted in an oil bath at 170°C for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature and then added dropwise to methanol to precipitate a solid, which was filtered to obtain the product LA-081 (31.3 g, 79.4% yield). Mass spectrum: calculated value: 659.84; assay value: 659.77.

[0115] Example 15 Preparation of Compound LA-173

[0116] 1) Preparation of compound 11-1

[0117] Under nitrogen protection, 4-bromodibenzothiophene (64.68 mmol) (CAS: 97511-05-2), o-aminobiphenyl (64.68 mmol) (CAS: 90-41-5), tris(dibenzylideneacetone)dipalladium (1.3 mmol), tri-tert-butylphosphine (25.87 mmol), and sodium tert-butoxide (161.7 mmol) were added sequentially to a 500 ml three-necked reaction flask and dissolved in toluene (500 ml) solvent. The mixture was reacted in an oil bath at 60°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. The mixture was then purified by column chromatography to obtain compound 11-1 (14.9 g, yield 65.6%).

[0118] 2) Preparation of compound LA-173

[0119] Under nitrogen protection, compound 11-1 (48.60 mmol), compound 4-4 (48.60 mmol), tris(dibenzylideneacetone)dipalladium (2.4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (0.486 mmol), and sodium tert-butoxide (97.6 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-173 product (22.5 g, yield 71.2%).

[0120] Mass spectrum: calculated value 649.82; tested value 649.85.

[0121] Example 16 Preparation of Compound LA-422

[0122] Under nitrogen protection, 4-[N-(biphenyl-4-yl)-N-anilino]phenylboronic acid (71.69 mmol) (CAS: 1084334-86-0), compound 1-4 (59.74 mmol), tetrakistriphenylphosphine palladium (0.7 mmol), and potassium carbonate (215.1 mmol) were dissolved in a mixed solvent of toluene (500 ml), EtOH (125 ml), and pure water (125 ml). The mixture was reacted in an oil bath at 140°C for 5 hours, and a precipitated solid was precipitated. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature, and the precipitated solid product was washed with pure water and methanol to obtain compound LA-422 (24.2 g, yield 65.4%).

[0123] Mass spectrum: calculated value 619.78; tested value 619.85.

[0124] Example 17 Preparation of Compound LA-443

[0125] 1) Preparation of compound 2-5

[0126] Under nitrogen protection, compound 4-4 (59.74 mmol), diboronic acid pinacol ester (77.66 mmol), tris(dibenzylideneacetone)dipalladium (1.8 mmol), tricyclohexylphosphine (11.9 mmol), and potassium acetate (149.4 mmol) were dissolved in dioxane (200 ml) solvent and reacted in an oil bath at 110 ° C for 5 hours. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain compound 2-5 product (19.6 g, yield 77.0%).

[0127] 2) Preparation of Compound 2-6

[0128] Under nitrogen protection, compound 2-5 (33.28 mmol), m-chlorobromobenzene (30.25 mmol), tetrakistriphenylphosphine palladium (0.3 mmol), and potassium carbonate (90.7 mmol) were dissolved in a mixed solvent of toluene (400 ml), EtOH (100 ml), and pure water (100 ml). The mixture was reacted in an 85°C oil bath for 6 hours, and a precipitated solid was precipitated. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature, and the precipitated solid product was washed with pure water and methanol to obtain compound 2-6 (9.5 g, yield 76.4%).

[0129] 3) Preparation of compound LA-443

[0130] Under nitrogen protection, N-biphenyl-4-yl-3-dibenzo[B,D]furanamine (59.74 mmol) (CAS: 1290039-85-8), compound 2-6 (59.74 mmol), tris(dibenzylideneacetone)dipalladium (3.0 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (5.974 mmol), and sodium tert-butoxide (120.0 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-443 product (28.1 g, yield 66.3%).

[0131] Mass spectrum: calculated value 709.86; tested value 709.85.

[0132] Example 18 Preparation of Compound LA-444

[0133] The difference from Example 17 is that N-biphenyl-4-yl-3-dibenzo[B,D]furanamine is replaced with N-[1,1'-biphenyl-4-yl]-9,9-dimethyl-9H-fluoren-2-amine (CAS: 897671-69-1), and the other components and synthesis conditions remain unchanged to obtain LA-444 product (31.3 g, yield 71.2%).

[0134] Mass spectrum: calculated value 735.94; tested value 735.90.

[0135] Example 19 Preparation of Compound LA-548

[0136] 1) Preparation of compound 4-5

[0137] Under nitrogen protection, compound 4-4 (59.74 mmol), diboronic acid pinacol ester (77.66 mmol), tris(dibenzylideneacetone)dipalladium (1.8 mmol), tricyclohexylphosphine (11.9 mmol), and potassium acetate (149.4 mmol) were dissolved in dioxane (200 ml) solvent and reacted in an oil bath at 110 ° C for 5 hours. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain compound 4-5 product (16.2 g, yield 63.6%).

[0138] 2) Preparation of Compound 4-6

[0139] Under nitrogen protection, compound 4-5 (33.28 mmol), 1-chloro-4-bromonaphthalene (30.25 mmol), tetrakistriphenylphosphine palladium (0.3 mmol), and potassium carbonate (90.7 mmol) were dissolved in a mixed solvent of toluene (400 ml), EtOH (100 ml) and pure water (100 ml). The mixture was reacted in an 85°C oil bath for 6 hours, and a precipitated solid was precipitated. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature, and the precipitated solid product was washed with pure water and methanol to obtain compound 4-6 (10.6 g, yield 76.0%).

[0140] 3) Preparation of compound LA-548

[0141] Under nitrogen protection, N-[1,1'-biphenyl]-3-yl-[1,1'-biphenyl]-4-amine (59.74 mmol) (CAS: 570391-47-8), compound 4-6 (59.74 mmol), tris(dibenzylideneacetone)dipalladium (3.0 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (5.974 mmol), and sodium tert-butoxide (120.0 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was added dropwise to methanol to precipitate the solid, which was filtered to obtain the LA-548 product (30.7 g, yield 68.9%).

[0142] Mass spectrum: calculated value 745.94; tested value 745.87.

[0143] Example 20 Preparation of Compound LA-590

[0144] The difference from Example 19 is that N-[1,1'-biphenyl]-3-yl-[1,1'-biphenyl]-4-amine is replaced by N-(4-biphenyl)dibenzo[b,d]thiophene-3-amine (CAS: 1290039-87-0), and the other components and synthesis conditions remain unchanged to obtain LA-590 product (33.9 g, yield 72.5%).

[0145] Mass spectrum: calculated value 775.98; tested value 775.93.

[0146] Example 21 Preparation of Compound LA-157

[0147] The difference from Example 4 is that compound 1-4 is replaced by 4-4, and other components and synthesis conditions remain unchanged, to obtain LA-157 product (25.6 g, yield 67.6%).

[0148] Mass spectrum: calculated value is 633.76; tested value is 633.79.

[0149] Example 22 Preparation of Compound LA-169

[0150] The difference from Example 22 is that N-([1,1'-biphenyl]-3-yl)dibenzo[b,d]furan-3-amine is replaced by N-([[1,1'-biphenyl]-3-yl]dibenzo[B,D]thiophene-3-amine (CAS: 1923735-65-2), and the other components and synthesis conditions remain unchanged to obtain LA-169 product (21.9 g, yield 56.4%).

[0151] Mass spectrum: calculated value 649.82; tested value 649.80.

[0152] Example 23 Preparation of Compound LA-182

[0153] 1) Preparation of compound 13-1

[0154] Under nitrogen protection, 2-bromodibenzofuran (64.68 mmol) (CAS: 86-76-0), 3,4-diphenylaniline (64.68 mmol) (CAS: 10569-67-2), tris(dibenzylideneacetone)dipalladium (1.3 mmol), tri-tert-butylphosphine (25.87 mmol), and sodium tert-butoxide (161.7 mmol) were added sequentially to a 500 ml three-necked reaction flask and dissolved in toluene (500 ml) solvent. The mixture was reacted in an oil bath at 60 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. Then, compound 13-1 (15.9 g, yield 59.7%) was purified by column chromatography.

[0155] 2) Preparation of compound LA-182

[0156] Under nitrogen protection, compound 13-1 (48.60 mmol), compound 4-4 (48.60 mmol), tris(dibenzylideneacetone)dipalladium (2.4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (0.486 mmol), and sodium tert-butoxide (97.6 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-182 product (19.5 g, yield 56.5%).

[0157] Mass spectrum: calculated value 709.86; tested value 709.88.

[0158] Example 24 Preparation of Compound LA-232

[0159] The difference from Example 22 is that N-([1,1'-biphenyl]-3-yl)dibenzo[b,d]furan-3-amine is replaced with 3,6-diphenyl-9H-carbazole (CAS: 56525-79-2), and the other components and synthesis conditions remain unchanged to obtain LA-232 product (27.5 g, yield 74.5%).

[0160] Mass spectrum: calculated value is 617.76; tested value is 617.71.

[0161] Example 25 Preparation of Compound LA-259

[0162] 1) Preparation of compound 14-1

[0163] Under nitrogen protection, dibenzofuran-2-boric acid (71.69 mmol) (CAS: 402936-15-6), 3-bromo-6-phenyl-9H-carbazole (59.74 mmol) (CAS: 1303472-72-1), tetrakistriphenylphosphine palladium (0.7 mmol), and potassium carbonate (215.1 mmol) were dissolved in a mixed solvent of toluene (500 ml), EtOH (125 ml), and pure water (125 ml). The mixture was reacted in an oil bath at 140°C for 5 hours, and a precipitated solid was precipitated. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature, and the precipitated solid product was washed with pure water and methanol to obtain compound 14-1 (19.1 g, yield 78.1%).

[0164] 2) Preparation of compound LA-259

[0165] Under nitrogen protection, compound 14-1 (48.60 mmol), compound 1-4 (48.60 mmol), tris(dibenzylideneacetone)dipalladium (2.4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (0.486 mmol), and sodium tert-butoxide (97.6 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-259 product (22.6 g, yield 65.7%).

[0166] Mass spectrum: calculated value 707.74; tested value 707.83.

[0167] Example 26 Preparation of Compound LA-486

[0168] 1) Preparation of compound 15-1

[0169] Under nitrogen protection, compound 2-5 (33.28 mmol), p-chlorobromobenzene (30.25 mmol), tetrakistriphenylphosphine palladium (0.3 mmol), and potassium carbonate (90.7 mmol) were dissolved in a mixed solvent of toluene (400 ml), EtOH (100 ml), and pure water (100 ml). The mixture was reacted in an 85°C oil bath for 6 hours, and a precipitated solid was precipitated. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature, and the precipitated solid product was washed with pure water and methanol to obtain compound 15-1 (9.8 g, yield 78.8%).

[0170] 2) Preparation of compound LA-486

[0171] Under nitrogen protection, N-phenyl-4-benzidine (59.74 mmol) (CAS: 32228-99-2), compound 15-1 (59.74 mmol), tris(dibenzylideneacetone)dipalladium (3.0 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (5.974 mmol), and sodium tert-butoxide (120.0 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170°C for 3 hours. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature and then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-486 product (24.9 g, yield 67.2%).

[0172] Mass spectrum: calculated value 619.78; tested value 619.66.

[0173] Example 27 Preparation of Compound LA-503

[0174] The difference from Example 27 is that N-phenyl-4-benzidine is replaced by N-phenyl-3-dibenzofuran-2-amine (CAS: 406488-21-9), and the other components and synthesis conditions remain unchanged to obtain LA-503 product (25.2 g, yield 66.5%).

[0175] Mass spectrum: calculated value: 633.76; tested value: 633.71.

[0176] Example 28 Preparation of Compound LA-555

[0177] 1) Preparation of compound 12-1

[0178] Under nitrogen protection, N-(3-bromophenyl)-N-phenyl-[1,1-biphenyl]-4-amine (64.68 mmol) (CAS: 1134188-19-4), aniline (64.68 mmol), tris(dibenzylideneacetone)dipalladium (1.3 mmol), tri-tert-butylphosphine (25.87 mmol), and sodium tert-butoxide (161.7 mmol) were added sequentially to a 500 ml three-necked reaction flask and dissolved in toluene (500 ml) solvent. The mixture was reacted in an oil bath at 60 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. Then, compound 12-1 (24.1 g, yield 90%) was purified by column chromatography.

[0179] 2) Preparation of compound LA-555

[0180] Under nitrogen protection, compound 12-1 (48.60 mmol), compound 4-4 (48.60 mmol), tris(dibenzylideneacetone)dipalladium (2.4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (0.486 mmol), and sodium tert-butoxide (97.6 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-555 product (30.3 g, yield 88%).

[0181] Example 29 Preparation of Compound LA-556

[0182] 1) Preparation of compound 16-1

[0183] Under nitrogen protection, 3-bromo-N,N-diphenylaniline (64.68 mmol) (CAS: 78600-33-6), aniline (64.68 mmol), tris(dibenzylideneacetone)dipalladium (1.3 mmol), tri-tert-butylphosphine (25.87 mmol), and sodium tert-butoxide (161.7 mmol) were added sequentially to a 500 ml three-necked reaction flask and dissolved in toluene (500 ml) solvent. The mixture was reacted in an oil bath at 60°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic phase was concentrated. The mixture was then purified by column chromatography to obtain compound 12-1 (24.1 g, yield 75%).

[0184] 2) Preparation of compound LA-556

[0185] Under nitrogen protection, compound 16-1 (48.60 mmol), compound 4-4 (48.60 mmol), tris(dibenzylideneacetone)dipalladium (2.4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (0.486 mmol), and sodium tert-butoxide (97.6 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170°C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-556 product (21.3.3 g, yield 69%).

[0186] Example 30 Preparation of Compound LA-607

[0187] Under nitrogen protection, N-phenyl-3-dibenzofuran-2-amine (59.74 mmol) (CAS: 406488-21-9), compound 4-6 (59.74 mmol), tris(dibenzylideneacetone)dipalladium (3.0 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (5.974 mmol), sodium tert-butoxide (120.0 mmol) were dissolved in o-xylene (100 ml) solvent and reacted in an oil bath at 170 ° C for 3 hours. After the reaction was completed by TLC monitoring, the reaction solution was cooled to room temperature, and the reaction solution was then added dropwise to methanol to precipitate a solid, which was filtered to obtain the LA-607 product (30.3 g, yield 74.2%).

[0188] Mass spectrum: calculated value 683.82; tested value 683.87.

[0189] Device Example 1

[0190] The organic electroluminescent device was prepared using the compounds LA-002 and LB-001 prepared in Example 1. The specific steps are as follows:

[0191] 1) Substrate processing:

[0192] Select ITO / Ag / ITO glass with an anode surface as the substrate. First, use a stripping liquid to remove the protective film on the substrate surface. Then, use deionized water to perform ultrasonic and spray processes on the substrate after film removal. Finally, bake the substrate.

[0193] 2) Evaporation process:

[0194] ①Select the cleaned glass substrate and deposit the hole injection material HI-01 on the substrate with the anode by vacuum evaporation to form a thickness of The hole injection layer is co-evaporated with HT-01 and HI-01, and the doping ratio of HI-01 is 3%.

[0195] ②Vacuum evaporation is used to deposit the hole transport material HT-01 on the hole injection layer to form a thickness of hole transport layer.

[0196] ③ The light-emitting host material (LA-002:LB-001=1:1) and the doping material RD-01 were mixed and deposited on the hole transport layer in a mass ratio of 97:3 by vacuum evaporation to form a layer with a thickness of luminescent layer.

[0197] ④ Vacuum evaporation is used to deposit the hole blocking layer material HB-01 on the light emitting layer to form a thickness of hole blocking layer.

[0198] ⑤ The electron transport material ET-01 and Liq were mixed and evaporated on the hole blocking layer in a mass ratio of 50:50 by vacuum evaporation to form a layer with a thickness of electron transport layer.

[0199] ⑥Electron injection material YB is evaporated on the electron transport layer by vacuum evaporation to form a thickness of electron injection layer.

[0200] ⑦ Vacuum evaporation is used to deposit cathode material Mg:Ag (1:9) on the electron injection layer to form a layer with a thickness of cathode.

[0201] ⑧ CP-01 material is deposited on the cathode by vacuum evaporation to form a thickness of A light-emitting device can be obtained by adding a light extraction layer.

[0202] The other device embodiments and device comparative examples are compared with device embodiment 1 except that the main material and doping material of the light-emitting layer are different. The manufacturing methods are the same as those of device embodiment 1, which are not described in detail here. The details are shown in Table 1:

[0203] Table 1 Materials for the light-emitting layers of various device examples and comparative examples

[0204] The structure of the device is as follows:

[0205] Table 2 Test results of the light emitting devices in device examples 1-30 and device comparison examples 1-47

[0206] In summary, it can be seen from Table 2 that the light-emitting device made by using the specific heterocyclic combination and deuteration at specific positions provided by the present application has the effect of significantly reducing the driving voltage and significantly improving the current efficiency and life, specifically:

[0207] 1. In the present invention, the phenyl hydrogen of the connected benzene in the specific heterocycle is cationized after deuteration to reduce the breakage of the CH bond, and the amorphous film formed after deuteration is better. At the same time, by comparing the device examples 1-29 with the device comparison examples 1-29, the driving voltage of the light-emitting device made of the compound of the present invention after deuteration of benzene is significantly reduced, and the current efficiency and life are significantly improved.

[0208] 2. In the present invention, the compound formed by the specific combination of O and N heterocycles is more stable than the compound formed by the combination of S and N heterocycles. At the same time, by comparing the device example 7 with the device comparative example 30, the driving voltage of the light-emitting device made of the compound of the present invention is significantly reduced, and the current efficiency and life are significantly improved.

[0209] 3. In the present invention, a triarylamine-type main material is formed by a specific heterocycle and deuterated and connected to N, which has better hole transport ability than the triarylamine structure without N in the structure. At the same time, by comparing device Example 7 with device comparisons 31-35, the driving voltage of the light-emitting device made with the N-type triarylamine structure is significantly reduced, and the current efficiency and life are significantly improved.

[0210] 4. In the present invention, only after the benzene ring connected by specific O and N heterocycles is deuterated, the compound is more stable and has a stronger ability to transport holes and electrons. At the same time, by comparing device examples 1, 6, 30 with device comparisons 36, 37, 38, 39, 46, and 47, the driving voltage of the light-emitting device made of the deuterated compound on the benzene ring is significantly lower than that of the compound deuterated at other positions, and the current efficiency and life are significantly improved.

[0211] 5. The first host of the present invention is combined with the second host containing a triazine structure to form a host material. The first host has a strong hole transport capability, and the second host has a strong electron transport capability. In this way, the recombination efficiency of holes and electrons in the light-emitting layer is higher. At the same time, by comparing device embodiments 1, 6, 11, 17, 14, 25 with device pairs 40-45, the driving voltage of the light-emitting device made using the second host compound provided by the present invention is significantly lower than that made with a compound not containing a triazine group, and the current efficiency and life are significantly improved.

[0212] 6. In the present invention, partial deuteration can improve the current efficiency and lifespan of the device. As can be seen from Device Example 30 and Comparative Example 47, deuteration is generally believed to improve efficiency and extend lifespan, presumably due to the lower activity of D compared to H. However, chemical reaction activity does not fully correspond to the activity under OLED electroluminescent conditions. For example, data from the examples of prior art patent CN112812106B demonstrate that deuteration of compounds in the green light-emitting host material shown there has a suboptimal effect on device efficiency and lifespan. Therefore, strictly speaking, there is no definitive directional guidance for the effect of deuteration or partial deuteration on the performance of OLED materials, and the current efficiency of the partially deuterated device in Device Example 30 of the present invention is significantly higher than that of Comparative Example 47.

[0213] The above description of the disclosed embodiments is intended to enable one skilled in the art to implement or use the present invention. Various modifications to these embodiments will be readily apparent to one skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention is not limited to the embodiments shown herein but is intended to conform to the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. An organic electroluminescent compound, characterized in that, The organic electroluminescent compound is represented by the following formula LA: Wherein: Both f and n are integers, and f + n = 1; Ar1 is R4, R5, R6, R7, and R8 are all D; Ar2 and Ar3 are independently selected from: R1, R2, R3, Ar4, Ar5, Ar6, and Ar7 are independently selected from aryl groups having 6 to 30 carbon atoms, heteroaryl groups having 4 to 20 carbon atoms, and combinations thereof; the aryl groups are selected from substituted and unsubstituted benzene, naphthalene, anthracene, phenanthrene, biphenyl, terphenyl, quaterphenyl, fluorene, diphenylfluorene, dibenzofluorene; the heteroaryl groups are selected from substituted and unsubstituted pyridine, dibenzofuran, dibenzothiophene, quinoline, carbazole, benzonaphthofuran, benzonaphthothiophene, quinoxaline, quinazoline, benzocarbazole, dibenzocarbazole; the substituents in the aryl groups and heteroaryl groups are D, F, or phenyl; when substituted with phenyl, the phenyl can be fused with adjacent groups to form a ring.

2. The organic electroluminescent compound according to claim 1, wherein The organic electroluminescent compound LA described above is selected from any one of the following structures:

3. A dual-host organic electroluminescent material, characterized in that, The dual-host organic electroluminescent material includes the organic electroluminescent compound LA and the organic electroluminescent compound LB as described in Claim 1, and the mass ratio of LA to LB is 1:99 - 99:

1. The structural formula of LB is as follows: Wherein, La, Lb, Lc, X1, X2, and X3 are selected from single bonds, substituted and unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted and unsubstituted heteroaryl groups having 4 to 20 carbon atoms, the heteroatoms in the heteroaryl groups are O, S, or N, and the substituents of the aryl groups and heteroaryl groups are D, F, or phenyl.

4. The dual-host organic electroluminescent material according to claim 3, wherein The organic electroluminescent compound LB described above is selected from any one of the following structures:

5. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and an organic electroluminescent material layer disposed between the first electrode and the second electrode; and, the organic electroluminescent material layer includes a light-emitting layer; the light-emitting layer includes a doping material and a host material, and the host material includes the dual-host organic electroluminescent material as described in claim 1.

6. The organic electroluminescent device according to claim 5, wherein, The mass ratio of the host material to the doping material is 5 - 99.5:1.

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