Organic electroluminescent compound, host materials, and light-emitting device and light-emitting apparatus comprising same

Abstract

The present invention relates to the technical field of organic electroluminescent materials and provides an organic electroluminescent compound, host materials, and a light-emitting device and light-emitting apparatus comprising same. The host materials comprise an organic electroluminescent compound Lx and an organic electroluminescent compound Ly, wherein the mass ratio of Lx to Ly is 1:99-99:1, and the general structural formula of Lx and Ly are as shown in the description. In the present invention, a specific combination of host materials solves the problems in the prior art of low efficiency and short service life of a phosphorescent material applied to an organic electroluminescent device.

Description

An organic electroluminescent compound, multiple host materials, and light-emitting devices and light-emitting apparatus containing the same

[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 26, 2024, with patent application number 2024101128468, entitled "An organic electroluminescent compound, multiple host materials, and light-emitting devices and light-emitting devices containing the same"; 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 compound, a plurality of host materials, and a light-emitting device and a light-emitting apparatus 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 compound, multiple host materials, and light-emitting devices and light-emitting apparatuses containing the same. The present invention solves the problems of low efficiency and short lifespan of phosphorescent materials used in organic electroluminescent devices in the prior art by using a specific combination of multiple host materials.

[0006] In order to achieve the above object, the present invention adopts the following technical solutions:

[0007] The first technical purpose of the present invention is to provide an organic electroluminescent compound, which is represented by the following formula Lx:

[0008] in:

[0009] Both m and n are integers, and m+n=1;

[0010] Ar1, Ar2, Ar3, Ar4 and Ar5 are all D;

[0011] La and Lb are A1, and the structure is as follows:

[0012] Lc, Ld and Le are independently selected from the group consisting of a linker, a substituted and unsubstituted C6-C 30 Aryl, substituted and unsubstituted C4-C 20 heteroaryl;

[0013] X1 and X2 are independently selected from substituted and unsubstituted C6-C 30 Aryl, substituted and unsubstituted C4-C 20 Heteroaryl and combinations thereof;

[0014] The substituted group is selected from D, F and phenyl.

[0015] Further, the aryl group is selected from substituted and unsubstituted benzene, substituted and unsubstituted naphthalene, substituted and unsubstituted anthracene, substituted and unsubstituted phenanthrene, substituted and unsubstituted biphenyl, substituted and unsubstituted terphenyl, substituted and unsubstituted quaterphenyl, substituted and unsubstituted fluorene, substituted and unsubstituted diphenylfluorene, and combinations thereof;

[0016] The heteroaryl group is selected from substituted and unsubstituted pyridine, substituted and unsubstituted dibenzofuran, substituted and unsubstituted dibenzothiophene, substituted and unsubstituted quinoline, substituted and unsubstituted carbazole, substituted and unsubstituted benzonaphthofuran, substituted and unsubstituted benzonaphthothiophene, substituted and unsubstituted quinoxaline, substituted and unsubstituted quinazoline, substituted and unsubstituted benzocarbazole, substituted and unsubstituted dibenzofluorene, substituted and unsubstituted dibenzocarbazole;

[0017] The substituted group is selected from D, F and phenyl.

[0018] Furthermore, the organic electroluminescent compound Lx is selected from any one of the following structures:

[0019] The second technical object of the present invention is to provide a plurality of host materials, wherein the plurality of host materials include the organic electroluminescent compound Lx and the organic electroluminescent compound Ly as described above, and the mass ratio of Lx to Ly is 1:99-99:1, and the organic electroluminescent compound Ly is selected from Ly1 or Ly2:

[0020] wherein R1, R2, R3, R4, R5 and R6 are independently selected from substituted and unsubstituted C6-C30 aryl groups, substituted and unsubstituted C4-C20 heteroaryl groups, wherein the heteroatom in the heteroaryl group is O, S or N;

[0021] The substituted group is selected from D, F and phenyl.

[0022] Furthermore, the organic electroluminescent compound Ly is selected from any one of the following structures:

[0023] The present invention also provides a light-emitting device, which includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode; and the organic layer includes a light-emitting layer; the light-emitting layer includes the multiple host materials described above.

[0024] Furthermore, the organic layer further comprises one or more of a hole injection layer, a hole transport layer, a layer having both hole injection and hole transport functions, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a layer having both electron transport and electron injection functions; wherein,

[0025] At least one organic layer contains the organic electroluminescent compound Lx and the organic electroluminescent compound Ly as described above.

[0026] Furthermore, the light-emitting layer includes a host material and a doping material, and the mass ratio of the host material to the doping material is 10-99.5:1.

[0027] It should be noted that the present applicant has conducted relevant tests on the above LA-001-LA-676 and found that when the above compounds are combined with compounds LB-001-LB-163 as the main body for use in light-emitting devices, they can significantly improve the luminous efficiency, increase the service life, and reduce the starting voltage.

[0028] Furthermore, the present invention further seeks to protect a light-emitting device, including an organic solar cell, electronic paper, an organic photoreceptor, or an organic thin-film transistor. By introducing the inventive Lx and Ly compounds into the light-emitting layer, the device is endowed with superior performance.

[0029] It can be seen from the above technical solutions that compared with the prior art, the present invention has the following beneficial effects:

[0030] The present invention solves the problems of low efficiency and short life when phosphorescent materials are applied to organic electroluminescent devices in the prior art by using a specific combination of multiple host materials. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] 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.

[0032] FIG1 is a mass spectrum of LA-007 of the present invention.

[0033] FIG2 is a hydrogen nuclear magnetic resonance spectrum of LA-007 of the present invention.

[0034] FIG3 is a mass spectrum of LA-051 of the present invention

[0035] FIG4 is a hydrogen nuclear magnetic resonance spectrum of LA-051 of the present invention.

[0036] FIG5 is a mass spectrum of LA-156 of the present invention.

[0037] FIG6 is a hydrogen nuclear magnetic resonance spectrum of LA-156 of the present invention

[0038] FIG7 is a mass spectrum of LA-196 of the present invention.

[0039] FIG8 is a hydrogen nuclear magnetic resonance spectrum of LA-196 of the present invention.

[0040] FIG9 is a mass spectrum of LA-210 of the present invention.

[0041] FIG10 is a hydrogen nuclear magnetic resonance spectrum of LA-210 of the present invention

[0042] FIG11 is a mass spectrum of LA-274 of the present invention

[0043] FIG12 is a hydrogen nuclear magnetic resonance spectrum of LA-274 of the present invention DETAILED DESCRIPTION

[0044] The technical solutions in the embodiments of the present application will be clearly and completely described below in combination with the organic electroluminescent compounds of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all the embodiments.

[0045] The mass spectrometer model used in the mass spectrometry test in this application is Waters XEVO TQD, low precision, ESI source test.

[0046] 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.

[0047] Example 1 Preparation of Compound LA-007

[0048] 1) Preparation of compound 1-1

[0049] 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.

[0050] 2) Preparation of compound 1-2

[0051] Under nitrogen protection, compound 1-1 (82.39 mmol), 5-chloro-2-formylphenylboronic acid (90.76 mmol) (CAS: 870238-36-1), 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 (250 ml) and pure water (250 ml). The mixture was reacted in an oil bath at 100 ° 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%).

[0052] 3) Preparation of Compound 1-3

[0053] 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%).

[0054] 4) Preparation of Compound 1-4

[0055] 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%).

[0056] 5) Preparation of Compound 1-5

[0057] Under nitrogen protection, compound 1-4 (30 mmol), pinacol borate (60 mmol), tris(dibenzylideneacetone)dipalladium (1.5 mmol), tricyclohexylphosphine (15 mmol), and potassium acetate (120 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 give compound 1-5 (9.59 g, yield 75%).

[0058] 6) Preparation of compound LA-007

[0059] Under nitrogen protection, compound 1-5 (22 mmol), 2-([1,1'-biphenyl]-2-yl)-4-([1,1]-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (20 mmol) (CAS: 2279137-61-8), tetrakistriphenylphosphine palladium (0.3 mmol), and potassium carbonate (90.7 mmol) were dissolved in a mixed solvent of toluene (400 ml), EtOH (200 ml), and pure water (200 ml). The mixture was reacted in an oil bath at 85°C 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 LA-007 (8.73 g, yield 63.8%).

[0060] Mass spectrum: as shown in Figure 1 below.

[0061] NMR: as shown in Figure 2 below.

[0062] Example 2 Preparation of Compound LA-051

[0063] 1) Preparation of compound 2-1

[0064] Under nitrogen protection, dibenzothiophene-2-boric acid (71.69 mmol) (CAS: 668983-97-9), 2,4-dichloro-6-phenyl-1,3,5-triazine (59.74 mmol) (CAS: 1700-02-3), tetrakistriphenylphosphine palladium (0.7 mmol), and potassium carbonate (215.1 mmol) were dissolved in a mixed solvent of toluene (500 ml), EtOH (250 ml) and pure water (250 ml). The reaction was carried out in an oil bath at 100°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 2-1 (12.6 g, yield 56.4%).

[0065] 2) Preparation of compound LA-051

[0066] Under nitrogen protection, compound 1-5 (33.28 mmol), compound 2-1 (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 (200 ml), and pure water (200 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 LA-051 (14.8 g, yield 76.7%).

[0067] Mass spectrum: as shown in Figure 3 below.

[0068] NMR: as shown in Figure 4 below.

[0069] Example 3 Preparation of Compound LA-156

[0070] 1) Preparation of compound 3-1

[0071] Under nitrogen protection, 11,11-dimethyl-11H-benzo[B]fluoren-2-yl)boric acid (71.69 mmol) (CAS: 1198396-40-5), 2-([1,1'-biphenyl]-2-yl)-4,6-dichloro-1,3,5-triazine (59.74 mmol) (CAS: 2134165-04-9), tetrakistriphenylphosphine palladium (0.7 mmol), and potassium carbonate (215.1 mmol) were dissolved in a mixed solvent of toluene (500 ml), EtOH (250 ml), and pure water (250 ml). The mixture was reacted in an oil bath at 100°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 3-1 (21.7 g, yield 71.2%).

[0072] 2) Preparation of compound LA-156

[0073] Under nitrogen protection, compound 1-5 (33.28 mmol), compound 3-1 (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 (200 ml), and pure water (200 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 LA-156 (15.5 g, yield 66.2%).

[0074] Mass spectrum: as shown in Figure 5 below.

[0075] NMR: As shown in Figure 6 below.

[0076] Example 4 Preparation of Compound LA-196

[0077] 1) Preparation of compound LA-196

[0078] Under nitrogen protection, compound 1-5 (33.28 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (30.25 mmol) (CAS: 1883265-32-4), tetrakistriphenylphosphine palladium (0.3 mmol), and potassium carbonate (90.7 mmol) were dissolved in a mixed solvent of toluene (400 ml), EtOH (200 ml), and pure water (200 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 LA-196 (11.3 g, yield 60.1%).

[0079] Mass spectrum: as shown in Figure 7 below.

[0080] NMR: as shown in Figure 8 below.

[0081] Example 5 Preparation of Compound LA-210

[0082] 1) Preparation of compound LA-210

[0083] Under nitrogen protection, compound 1-5 (33.28 mmol), 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-(dibenzo[b,d]furan-1-yl)-1,3,5-triazine (30.25 mmol) (CAS: 2639487-21-9), tetrakistriphenylphosphine palladium (0.3 mmol), and potassium carbonate (90.7 mmol) were dissolved in a mixed solvent of toluene (400 ml), EtOH (200 ml), and pure water (200 ml). The mixture was reacted in an oil bath at 85°C 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 LA-210 (13.9 g, yield 65.8%).

[0084] Mass spectrum: as shown in Figure 9 below.

[0085] NMR: as shown in Figure 10 below.

[0086] Example 6 Preparation of Compound LA-274

[0087] 1) Preparation of compound 4-1

[0088] Under nitrogen protection, (9-phenyl-9H-carbazol-4-yl)boric acid (71.69 mmol) (CAS: 1370555-65-9), 2,4-dichloro-6-([1,1'-biphenyl]-3-yl)-1,3,5-triazine (59.74 mmol) (CAS: 1002225-89-1), tetrakistriphenylphosphine palladium (0.7 mmol), and potassium carbonate (215.1 mmol) were dissolved in a mixed solvent of toluene (500 ml), EtOH (250 ml), and pure water (250 ml). The mixture was reacted in an oil bath at 100°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 4-1 (18.5 g, yield 60.8%).

[0089] 2) Preparation of compound LA-274

[0090] Under nitrogen protection, compound 1-5 (33.28 mmol), compound 4-1 (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 (200 ml) and pure water (200 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 LA-274 (17.6 g, yield 75.3%).

[0091] Mass spectrum: as shown in Figure 11 below.

[0092] NMR: As shown in Figure 12 below.

[0093] Example 7 Preparation of Compound LA-334

[0094] 1) Preparation of compound 5-1

[0095] Under nitrogen protection, 2-naphthaleneboronic acid (71.69 mmol) (CAS: 32316-92-0), 2-([1,1'-biphenyl]-2-yl)-4,6-dichloro-1,3,5-triazine (59.74 mmol) (CAS: 2134165-04-9), tetrakistriphenylphosphine palladium (0.7 mmol), and potassium carbonate (215.1 mmol) were dissolved in a mixed solvent of toluene (500 ml), EtOH (250 ml), and pure water (250 ml). The mixture was reacted in an oil bath at 100°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 5-1 (17.1 g, yield 72.7%).

[0096] 2) Preparation of compound LA-334

[0097] Under nitrogen protection, compound 1-5 (33.28 mmol), compound 5-1 (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 (200 ml), and pure water (200 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 LA-334 (15.1 g, yield 75.9%).

[0098] Mass spectrum: calculated value is 657.26; tested value is 658.29.

[0099] Example 8 Preparation of Compound LA-424

[0100] 1) Preparation of compound LA-424

[0101] Under nitrogen protection, compound 2-5 (33.28 mmol), 2-[1,1'-biphenyl]-2-yl-4-chloro-6-phenyl-1,3,5-triazine (30.25 mmol) (CAS: 1835683-68-5), tetrakistriphenylphosphine palladium (0.3 mmol), and potassium carbonate (90.7 mmol) were dissolved in a mixed solvent of toluene (400 ml), EtOH (200 ml), and pure water (200 ml). The mixture was reacted in an oil bath at 85°C 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 LA-424 (15.0 g, yield 81.6%).

[0102] Mass spectrum: calculated value is 607.24; measured value is 608.25.

[0103] Example 9 Preparation of Compound LA-464

[0104] 1) Preparation of compound 2-5

[0105] Compound 2-5 was prepared in the same manner as described for compound 1-5, except that 5-chloro-2-formylphenylboronic acid was replaced by 4-chloro-2-formylphenylboronic acid, and the reaction molar ratios of other raw materials were the same.

[0106] 2) Preparation of compound LA-464

[0107] Under nitrogen protection, compound 2-5 (33.28 mmol), 2-chloro-4-(dibenzo[b,d]thiophene-3-yl)-6-phenyl-1,3,5-triazine (30.25 mmol) (CAS: 2172889-29-9), tetrakistriphenylphosphine palladium (0.3 mmol), and potassium carbonate (90.7 mmol) were dissolved in a mixed solvent of toluene (400 ml), EtOH (200 ml), and pure water (200 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 LA-464 (15.8 g, yield 81.9%).

[0108] Mass spectrum: calculated value is 637.20; measured value is 638.22.

[0109] Example 10 Preparation of Compound LA-514

[0110] 1) Preparation of compound LA-514

[0111] Under nitrogen protection, compound 2-5 (33.28 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (30.25 mmol) (CAS: 1883265-32-4), tetrakistriphenylphosphine palladium (0.3 mmol), and potassium carbonate (90.7 mmol) were dissolved in a mixed solvent of toluene (400 ml), EtOH (200 ml), and pure water (200 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 LA-514 (14.2 g, yield 75.5%).

[0112] Mass spectrum: calculated value: 621.22; tested value: 622.20.

[0113] Example 11 Preparation of Compound LA-562

[0114] 1) Preparation of compound 6-1

[0115] Under nitrogen protection, (3-(dibenzo[B,D]furan-1-yl)phenyl)boronic acid (71.69mmol) (CAS: 2229864-76-8), 2,4-dichloro-6-phenyl-1,3,5-triazine (59.74mmol) (CAS: 1700-02-3), tetrakistriphenylphosphine palladium (0.7mmol), and potassium carbonate (215.1mmol) were dissolved in a mixed solvent of toluene (500ml), EtOH (250ml) and pure water (250ml). The reaction was carried out in an oil bath at 100°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 6-1 (20.6g, yield 79.5%).

[0116] 2) Preparation of compound LA-562

[0117] Under nitrogen protection, compound 2-5 (33.28 mmol), compound 6-1 (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 (200 ml) and pure water (200 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 LA-562 (18.8 g, yield 89.1%).

[0118] Mass spectrum: calculated value is 697.25; measured value is 698.27.

[0119] Example 12 Preparation of Compound LA-592

[0120] 1) Preparation of compound 7-1

[0121] Under nitrogen protection, 2-naphthaleneboric acid (71.69 mmol) (CAS: 32316-92-0), 2-(4-biphenyl)-4,6-dichloro-1,3,5-triazine (59.74 mmol) (CAS: 10202-45-6), tetrakistriphenylphosphine palladium (0.7 mmol), and potassium carbonate (215.1 mmol) were dissolved in a mixed solvent of toluene (500 ml), EtOH (250 ml) and pure water (250 ml). The reaction was carried out in an oil bath at 100°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 7-1 (17.4 g, yield 73.9%).

[0122] 2) Preparation of compound LA-592

[0123] Under nitrogen protection, compound 2-5 (33.28 mmol), compound 7-1 (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 (200 ml) and pure water (200 ml). The mixture was reacted in an 85°C oil bath for 6 hours. A precipitated solid was precipitated. After the reaction was completed as monitored by TLC, the reaction solution was cooled to room temperature. The precipitated solid product was washed with pure water and methanol to obtain compound LA-592 (11.7 g, yield 58.8%).

[0124] Mass spectrum: calculated value 657.26; tested value 658.27.

[0125] Device Example 1

[0126] The organic electroluminescent device was prepared using the compounds LA-007 and LB-001 prepared in Example 1. The specific steps are as follows:

[0127] 1) Substrate processing:

[0128] 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.

[0129] 2) Evaporation process:

[0130] 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%.

[0131] 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.

[0132] ③ The light-emitting host material (LA-007: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.

[0133] 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.

[0134] 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.

[0135] ⑥Electron injection material YB is evaporated on the electron transport layer by vacuum evaporation to form a thickness of electron injection layer.

[0136] 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.

[0137] 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.

[0138] 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:

[0139] Table 1 Materials for the light-emitting layers of various device examples and comparative examples

[0140] The structure of the device is as follows:

[0141] In addition, the light emitting devices obtained from the device examples 1-12 and the device comparative examples 1-19 were subjected to a current density of 10 mA / cm 2 The various performances were tested under the conditions of , and the test results are shown in Table 2.

[0142] Table 2 Test results of the light emitting devices in device examples 1-12 and device comparison examples 1-19

[0143] In summary, it can be seen from Table 2 that

[0144] The light-emitting device provided by the present application, which is made by using a specific heterocyclic combination and deuteration at a specific position, has the effects of significantly reducing the driving voltage and significantly improving the current efficiency and lifespan, specifically:

[0145] 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 C-H bond, and the amorphous film formed after deuteration is better. At the same time, by comparing the device examples 1-12 with the device comparative examples 1-12, 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.

[0146] 2. In the present invention, the main material formed by a specific heterocycle and deuterated and connected to triazine has better electron transmission ability than the structure without triazine. At the same time, by comparing device example 1 with device comparisons 13-16, the driving voltage of the light-emitting device made with the triazine structure is significantly reduced, and the current efficiency and life are significantly improved.

[0147] 3. The first host of the present invention is combined with a second host containing a triarylamine or carbazole derivative to form a host material. The first host has a strong electron transport capability, and the second host has a strong hole 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, 4, and 7 with device comparative examples 17-19, the driving voltage of the light-emitting device made of the second host compound provided by the present invention is significantly lower than that of the compound not containing a triarylamine or carbazole derivative, and the current efficiency and life are significantly improved.

[0148] 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 Lx: Wherein: Both m and n are integers, and m + n = 1; Ar1, Ar2, Ar3, Ar4 and Ar5 are all D; La and Lb are A1, with the following structure: Lc, Ld, and Le are independently selected from a linking bond, a substituted and unsubstituted C6-C 30 aryl, a substituted and unsubstituted C4-C 20 heteroaryl; X1 and X2 are independently selected from substituted and unsubstituted C6-C 30 aryl, substituted and unsubstituted C4-C 20 heteroaryl, and combinations thereof; The substitution is selected from D, F and phenyl.

2. The organic electroluminescent compound according to claim 1, characterized in that, The aryl group is selected from substituted and unsubstituted benzene, substituted and unsubstituted naphthalene, substituted and unsubstituted anthracene, substituted and unsubstituted phenanthrene, substituted and unsubstituted biphenyl, substituted and unsubstituted terphenyl, substituted and unsubstituted quaterphenyl, substituted and unsubstituted fluorene, substituted and unsubstituted diphenylfluorene, and combinations thereof; The heteroaryl group is selected from substituted and unsubstituted pyridine, substituted and unsubstituted dibenzofuran, substituted and unsubstituted dibenzothiophene, substituted and unsubstituted quinoline, substituted and unsubstituted carbazole, substituted and unsubstituted benzonaphthofuran, substituted and unsubstituted benzonaphthothiophene, substituted and unsubstituted quinoxaline, substituted and unsubstituted quinazoline, substituted and unsubstituted benzocarbazole, substituted and unsubstituted dibenzofluorene, substituted and unsubstituted dibenzocarbazole; The substitution is selected from D, F and phenyl.

3. The organic electroluminescent compound according to claim 1, wherein The organic electroluminescent compound Lx is selected from any one of the following structures:

4. A multi-main body material, characterized in that, The multiple host materials include the organic electroluminescent compound Lx and the organic electroluminescent compound Ly as described in claim 1, and the mass ratio of Lx to Ly is 1:99 to 99:

1. The organic electroluminescent compound Ly is selected from Ly1 or Ly2: Wherein, R1, R2, R3, R4, R5 and R6 are independently selected from substituted and unsubstituted C6-C30 aryl groups, substituted and unsubstituted C4-C20 heteroaryl groups, and the heteroatoms in the heteroaryl groups are O, S or N; The substitution is selected from D, F and phenyl.

5. The multiple main materials according to claim 4, characterized in that, The organic electroluminescent compound Ly described above is selected from any one of the following structures:

6. A light-emitting device, characterized in that, The light-emitting device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode; and, the organic layer includes a light-emitting layer; the light-emitting layer includes a plurality of host materials as described in claim 4.

7. The light-emitting device according to claim 6, wherein, The organic layer further includes one or more of a hole injection layer, a hole transport layer, a layer having both hole injection and hole transport functions, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a layer having both electron transport and electron injection functions; wherein, At least one organic layer contains the organic electroluminescent compound Lx as described in claim 1 and the organic electroluminescent compound Ly.

8. The light-emitting device according to claim 6, characterized in that, The light-emitting layer includes a host material and a doping material, and the mass ratio of the host material to the doping material is 10-99.5:

1.

9. A light-emitting device, characterized in that, The light-emitting device contains the light-emitting device as described in claim 6, and the light-emitting device includes an organic solar cell, an electronic paper, an organic photoreceptor or an organic thin film transistor.

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