Organic electroluminescent compound and application thereof

Abstract

The invention relates to an organic electroluminescent compound and application thereof, and belongs to the technical field of photoelectric materials, the organic electroluminescent compound is a compound as shown in a formula 1: # imgabs0. HOMO and LUMO energy levels of the organic electroluminescent compound provided by the invention have high matching degree with adjacent energy levels, and the organic electroluminescent compound has high photoelectric conversion efficiency. According to the organic electroluminescent compound, the mobility of carriers containing the organic electroluminescent compound is relatively balanced, so that the organic electroluminescent device containing the organic electroluminescent compound has relatively low driving voltage, relatively high luminous efficiency and relatively long service life.

Description

Technical Field

[0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to an organic electroluminescent compound and application thereof. Background Art

[0002] Organic electroluminescent devices (OLEDs) are a technology that uses specific organic materials to emit light when electrically stimulated. The basic structure of this device includes an anode, a cathode, and an organic material layer located between the two. The organic material layer can be further subdivided into multiple functional layers based on their functions, such as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (which contains a host material and a dopant), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. During the operation of an OLED, when a voltage is applied between the anode and the cathode, the anode injects positive charge carriers (i.e., holes) into the light-emitting layer, while the cathode injects negative charge carriers (i.e., electrons) into the same layer. When these holes and electrons meet and combine in the light-emitting layer, high-energy particles - excitons - are generated. As the energy of the excitons is released, it causes the organic light-emitting material to enter an excited state. Subsequently, when these materials return from the excited state to a stable state, they release the previously absorbed energy in the form of light, thereby achieving a light-emitting effect. The most important factor determining the light-emitting efficiency in an organic EL device is the light-emitting material.

[0003] The luminescent material must have high quantum efficiency and high electron and hole mobility, and the luminescent material layer formed must be uniform and stable. The luminescent material is divided into blue luminescent material, green luminescent material and red luminescent material according to the color of the light emitted, and further yellow luminescent material or orange luminescent material. In addition, the luminescent material can also be divided into a main material and a doping material according to its function.

[0004] At present, one of the main challenges facing organic electroluminescent materials is their relatively low stability. In addition, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of organic electroluminescent materials are not well matched with other related energy levels, which leads to an unbalanced rate of the two carriers, holes and electrons, during the transmission process. This imbalance not only leads to a higher operating voltage of the organic electroluminescent device, but also leads to a decrease in luminous efficiency, shortening the service life of the device. These problems greatly limit the potential and development of organic electroluminescent devices in practical applications. In view of this, the present invention provides an organic electroluminescent compound and its application. Summary of the invention

[0005] The technical problem to be solved by the present invention is to provide an organic electroluminescent compound and its application. The purpose is to solve the problems of the energy level difference between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), the operating voltage, the luminous efficiency and the service life of the device faced by the existing organic electroluminescent materials.

[0006] The technical solution of the present invention to solve the above technical problems is as follows:

[0007] In a first aspect, an organic electroluminescent compound is characterized in that the organic electroluminescent compound is a compound represented by Formula 1:

[0008]

[0009] In formula 1, R 1 -R 10 1-2 of them with L 1 or / and L 2 Connected, the remaining R 1 -R 10 The same or different groups are independently selected from any one of the following groups: hydrogen, deuterium, cyano, C 1 -C 10 Alkyl, C 1 -C 10 Alkylsilyl, C 6 -C 12 The aromatic group;

[0010] In formula 1, L 1 -L 2 The same or different are independently selected from any of the following: single bond, unsubstituted or substituted with deuterium, C 1 -C 5 Alkyl, cyano, nitro substituted C 6 -C 15 Arylene, unsubstituted or substituted with deuterium, C 1 -C 5 Alkyl, cyano, nitro substituted C 4 -C 12 Heteroarylene;

[0011] In formula 1, R 11 Any one selected from the following groups: hydrogen, N(R 18 )(R 19 ), C 6 -C 25 The aromatic group, C 4 -C 25 A heteroaryl group, a structure shown in Formula 2;

[0012] In formula 1, R 12 Selected from the structure shown in Formula 2:

[0013]

[0014] In formula 2, R 13 -R 16 The same or different groups are independently selected from the following groups: 1 -C 10 The alkyl group;

[0015] In formula 2, R 17 Selected from the following groups: hydrogen, C 1 -C 10 Alkyl, unsubstituted or substituted with deuterium, C 1 -C 5 Alkyl, cyano, nitro substituted C 6 -C 15 The aromatic group;

[0016] In formula 2 Represents: empty or single key;

[0017] R 18 -R 19 The same or different are independently selected from any one of the following groups: C 6 -C 25 The aromatic group, C 4 -C 25 The heteroaryl group.

[0018] Furthermore, the structure represented by Formula 1 is selected from any one of the following structures:

[0019]

[0020] Furthermore, when L 1 -L 2 C 6 -C 15 Arylene or C 4 -C 12 When the heteroarylene group is 1 -L 2 The structure is shown in formula 3:

[0021]

[0022] In formula 3 represents the junction site;

[0023] X 1 At least one selected from the following groups: CH, CD, N; or two adjacent X 1 It forms a fused ring structure with the phenyl group by sharing a chemical bond.

[0024] The number of N is 0, 1, 2, or 3; the preferred number of N is 0 or 1.

[0025] Furthermore, L 1 -L 2 Preferred structures are: phenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl;

[0026] Furthermore, when R 11 Selected from C 6 -C 25 The aromatic group, C 4 -C 25 When the heteroaryl group is 11 The structure shown in Formula 4 or the structure shown in Formula 4 and The fused ring structure is formed by sharing chemical bonds:

[0027]

[0028] In formula 4, X 2a -X 2c is selected from the following groups: CH or N;

[0029] R 20 -R 21 The same or different groups are independently selected from any one of the following groups: hydrogen, cyano, C 1 -C 10 Alkyl, C 6 -C 15 The aromatic group, C 6 -C 12 Aromatic hetero groups;

[0030] X 3 Selected from the following groups: O, S, C(CH 3 , CH 3 ), N, NR 22 ;

[0031] n and m are the same or different and are selected from: 1, 2, 3;

[0032] * is the connection site;

[0033] R 22 Selected from the following groups: C 6 -C 15 The aryl group; R 22 Preferred are: phenyl, naphthyl, biphenyl.

[0034] Furthermore, when R 11 Selected from C 6 -C 25 When the aryl group is 11 The structure is shown in formula 4-1:

[0035]

[0036] In formula 4-1, R23 -R 27 The same or different groups are independently selected from any one of the following groups: hydrogen, deuterium, cyano, C 1 -C 10 Alkyl, deuterated C 1 -C 10 an alkyl group containing at least one N-containing six-membered heteroaryl group; or R 23 -R 27 The two adjacent substituents in the formula are connected to —CH=CH—CH=CH— through a common chemical bond to form a condensed ring structure; or R 23 -R 27 The two adjacent substituents in Connected to form a condensed ring structure;

[0037] When R 11 Selected from C 4 -C 25 When the heteroaryl group is 11 It is the structure shown in Formula 4-2 or Formula 4-3:

[0038]

[0039] Where R 20 -R 22 The same or different groups are independently selected from the following groups: hydrogen, deuterium, C 1 -C 10 Alkyl, six-membered aryl, six-membered heteroaryl containing at least one N, benzo six-membered aryl, formula 4-3;

[0040] When R 11 Selected from N(R 18 )(R 19 ), R 11 The structure is shown in Formula 5:

[0041]

[0042] In formula 5, R 28 -R 33 The same or different groups are independently selected from any one of the following groups: hydrogen, deuterium, cyano, C 1 -C 10 An alkyl group, a six-membered aryl group; or R 28 -R 33 The two adjacent substituents in the cyclohexane are connected to —CH═CH—CH═CH— through a common chemical bond to form a condensed ring structure, preferably R 29 -R 30 or R 31 -R 32 Any one of them is connected to —CH=CH—CH=CH— through a common chemical bond to form a condensed ring structure; or R28 -R 33 The two adjacent substituents in connected to form a condensed ring structure, preferably R 29 -R 30 or R 31 -R 32 Any of them shares a chemical bond with Connected to form a condensed ring structure;

[0043] X 4 Selected from any of the following groups: O, S, NR 34 ;

[0044] NR 34 Selected from: phenyl.

[0045] The six-membered heteroaryl group containing at least one N is selected from: pyridyl; the six-membered aryl group is selected from: phenyl.

[0046] Further, R 12 The structure is selected from any one of the following groups:

[0047]

[0048] R in Formula 2-1 and Formula 2-2 17 Any one selected from the following groups: hydrogen, deuterium, C 1 -C 5 The preferred R 17 Middle C 1 -C 5 The alkyl group is preferably tert-butyl.

[0049] Further, C 1 -C 10 The alkyl group is selected from: C 1 -C 5 The alkyl group is an alkyl group, wherein the hydrogen on the alkyl group is not deuterated or is replaced by at least one deuterium; preferably C 1 -C 10 The alkyl group is selected from: C 1 -C 8 , C 1 -C 6 , C 1 -C 5 , C 1 -C 4 , C 1 -C 3 Alkyl; further preferably C 1 -C 10 The alkyl group is selected from the group consisting of methyl, ethyl, propyl and tert-butyl;

[0050] When R 1-R 10 One or more of them is C 1 -C 10 The alkylsilyl group, whose C 1 -C 10 The alkylsilyl group is selected from: C 1 -C 5 Alkylsilyl; preferably C 1 -C 10 The alkyl group is selected from: C 1 -C 8 , C 1 -C 6 , C 1 -C 5 , C 1 -C 4 , C 1 -C 3 Alkylsilyl;

[0051] When R 1 -R 10 One or more of them is C 6 -C 12 The aryl group, whose C 6 -C 12 The aryl group is selected from: phenyl;

[0052] When R 1 -R 10 At most 2 substituents are C 1 -C 10 Alkyl, or / and C 1 -C 10 Alkylsilyl, or / and C 6 -C 12 The aromatic group.

[0053] Furthermore, the structure of the organic electroluminescent compound is any one of the following:

[0054]

[0055]

[0056]

[0057]

[0058]

[0059] In a second aspect, an application of an organic electroluminescent compound is used to prepare a luminescent host material or a luminescent guest material.

[0060] In a third aspect, an organic electroluminescent device comprises an organic material layer, wherein the organic material layer comprises the organic electroluminescent compound.

[0061] The organic electroluminescent device further comprises a cathode and an anode, and the organic material layer is located between the cathode and the anode;

[0062] Preferably, the organic material layer further comprises one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0063] Furthermore, the light-emitting layer includes the organic electroluminescent compound.

[0064] The present invention provides the use of the above-mentioned organic electroluminescent device in optical fiber equipment, lighting equipment, electronic photographic photosensitive body equipment, photoelectric converter, organic solar cell, switch element equipment, organic light-emitting field effect transistor, image sensor or dye laser.

[0065] The beneficial effects of the present invention are:

[0066] (1) The HOMO and LUMO energy levels of the organic electroluminescent compound provided by the present invention have a high degree of matching with the adjacent energy levels, so that the carrier mobility of the organic electroluminescent compound is relatively balanced, thereby making the organic electroluminescent device containing the organic electroluminescent compound have a lower driving voltage, higher luminous efficiency and longer life; compared with traditional materials, the use of the organic electroluminescent compound described in the present invention as a luminescent host material can emit higher quality blue light, which can improve the color expression and visual effect of display or lighting products.

[0067] (2) Devices using the organic electroluminescent compounds of the present invention have efficient charge transfer paths, thereby reducing voltage drops and energy losses; this enables the devices to operate stably at low voltages, helping to improve the energy efficiency of the overall system; it also means that the need for high-power power supplies is reduced, thereby reducing system complexity and cost.

[0068] (3) Current efficiency and LT (life test) 95 value of devices using the organic electroluminescent compound of the present invention; the light absorption capacity and charge separation efficiency of the main material are enhanced, so that the unit current output is higher and the service life of the device is extended; high current efficiency means that under the same input conditions, higher output power can be obtained, which is particularly important for application scenarios that pursue high energy density; and the improvement of LT95 value indicates that the device can still maintain high efficiency and low failure rate after long-term operation, which is particularly critical for equipment with extremely high requirements for stability and reliability.

[0069] (3) The present invention also successfully increases the glass transition temperature (Tg) of the material, effectively improving its thermal stability, so that the device can maintain structural integrity and performance stability even in high-temperature environments; this feature has important application value for electronic devices that need to operate under high-temperature conditions, and ensures the reliability and durability of the device in extreme environments. BRIEF DESCRIPTION OF THE DRAWINGS

[0070] Figure 1 It is the NMR image of the compound shown in Example 1 of the present invention. DETAILED DESCRIPTION

[0071] The following will be clearly and completely described in conjunction with the examples, and the described examples are only a part of the examples of the present invention, rather than all the examples. The following description of at least one exemplary embodiment is actually only illustrative and is not intended to be any limitation to the present invention and its application or use. Based on the examples in the present invention, all the other examples obtained by those of ordinary skill in the art without making creative work premises belong to the scope of protection of the present invention. The reagents or instruments used in the present invention are not indicated by the manufacturer, and are all conventional products that can be obtained by commercial purchase. For the processing parameters not particularly indicated, conventional techniques can be used for reference.

[0072] The following is a description of the preparation of the intermediates employed in Examples 1 to 20:

[0073] (1) Intermediates 1-6

[0074] The synthesis of intermediate 1 comprises the following steps:

[0075]

[0076] A-1 (20 g), A-2 (14.37 g), sodium tert-butoxide (10.32 g), Pd 2 (dba) 3 (0.6g), tri-tert-butylphosphine (0.28g) were suspended in 200ml toluene, stirred under hot reflux for 12 hours, extracted with dichloromethane and distilled water, the organic phase was retained, the organic phase was washed with brine 1-2 times, the organic phase was retained, and the spin-dried solid was added with ethanol, hot refluxed for 1h, passed through silica gel cake while hot, and spin-dried to obtain A-3 22.67g;

[0077] A-3 22.67g was dissolved in 200mL anhydrous THF, 3.68g of n-butyl lithium was injected at -78°C, reacted for 1 hour, 8.13g of anhydrous trimethyl borate was injected, reacted for 12 hours, water was added to quench the reaction, extracted with dichloromethane, dried, and recrystallized from n-hexane to obtain 16.24g of intermediate 1A-4. Test data: MS (MS+1): 400.3641.

[0078] The structural formula of intermediate 2-6 is as follows:

[0079]

[0080] Synthesis of intermediate 2: Replace A-1 in intermediate 1 with N-(4-(tert-butyl)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine, and keep A-2 and the catalyst, ligand, reaction conditions and post-treatment required for the reaction unchanged to synthesize intermediate 2;

[0081] MS(MS+1):455.1892;

[0082] Synthesis of intermediate 3: Replace A-1 in intermediate 1 with N-(4-(phenyl)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine, and keep A-2 and the catalyst, ligand, reaction conditions and post-treatment required for the reaction unchanged to synthesize intermediate 3;

[0083] MS(MS+1):476.6281;

[0084] Synthesis of intermediate 4: Replace A-1 in intermediate 1 with 7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole, and keep A-2 and the catalyst, ligand, reaction conditions and post-treatment required for the reaction unchanged to synthesize intermediate 4;

[0085] MS(MS+1):398.3967;

[0086] Synthesis of intermediate 5: A-1 in intermediate 1 is replaced with 2-(tert-butyl)-7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole, while A-2 and the catalyst, ligand, reaction conditions and post-treatment required for the reaction remain unchanged to synthesize intermediate 5;

[0087] MS(MS+1):454.4157;

[0088] Synthesis of intermediate 6: Replace A-1 in intermediate 1 with 2-(phenyl)-7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole, and keep A-2 and the catalyst, ligand, reaction conditions and post-treatment required for the reaction unchanged to synthesize intermediate 6;

[0089] MS(MS+1):474.6611;

[0090] (2) Intermediate 7-10

[0091] The synthesis of intermediate 7 comprises the following steps:

[0092] The synthesis of intermediate 7 comprises the following steps:

[0093]

[0094] Step 1: Add B-1 (20.00 g), B-2 (25.12 g), tetrakis(triphenylphosphine)palladium (0.8 g) and sodium carbonate (11.31 g) to 200 ml of a mixed solution of toluene (2V) / ethanol (1V) / water (1V). Under nitrogen protection, stir the reaction system at 100 degrees Celsius for 4 hours, and then cool to room temperature. Dilute the reaction system with water (50 ml), extract with ethyl acetate, retain the organic phase, dry the organic phase with anhydrous magnesium sulfate, concentrate the organic phase to a muddy state, add 50 ml of toluene, stir under hot reflux for 2 hours, filter while hot, retain the organic phase, and spin dry the organic phase to obtain 31.24 g of (B-3);

[0095] Step 2: Add B-3 (31.24 g) to 300 ml THF, stir to dissolve, add 1,3-dibromo-5,5-dimethylhydantoin (9.64 g), stir for 6-7 hours, and after the reaction is complete, add water to the reaction system for extraction, retain the organic phase, dry the organic phase with anhydrous magnesium sulfate, spin dry, pass through a silica gel column, and elute with petroleum ether: ethyl acetate = 10:1, and spin dry to obtain 32.48 g of intermediate 7 (B-4).

[0096] Test data: MS(MS+1):588.1582.

[0097] The structural formula of intermediate 8-10 is as follows:

[0098]

[0099] Synthesis of intermediate 8: Replace B-2 in intermediate 7 with N-phenyl-3-carbazoleboronic acid, and keep B-1 and the catalyst, ligand, reaction conditions and post-treatment required for the reaction unchanged to synthesize intermediate 8;

[0100] MS(MS+1):522.5924;

[0101] Synthesis of intermediate 9: Replace B-2 in intermediate 7 with dibenzothiophene-2-boric acid, and keep B-1 and the catalyst, ligand, reaction conditions and post-treatment required for the reaction unchanged to synthesize intermediate 9;

[0102] MS(MS+1):463.2861;

[0103] Synthesis of intermediate 10: Replace B-2 in intermediate 7 with 3-boronic acid-9,9-dimethylfluorene, and keep B-1 and the catalyst, ligand, reaction conditions and post-treatment required for the reaction unchanged to synthesize intermediate 10;

[0104] MS(MS+1):521.4795.

[0105] (3) Intermediate 11

[0106] The synthesis of intermediate 11 comprises the following steps:

[0107]

[0108] Step 1: Add C-1 (20.00 g), C-2 (12.40 g), tetrakis(triphenylphosphine)palladium (0.8 g) and sodium tert-butoxide (10.25 g) to 200 ml of a mixed solution of toluene (2V) / ethanol (1V) / water (1V). Under nitrogen protection, stir the reaction system at 100 degrees Celsius for 4 hours, and then cool to room temperature. Dilute the reaction system with water (50 ml), extract with ethyl acetate, retain the organic phase, dry the organic phase with anhydrous magnesium sulfate, concentrate the organic phase to a muddy state, add 50 ml of toluene, stir under hot reflux for 2 hours, filter while hot, retain the organic phase, and spin dry the organic phase to obtain 20.36 g of (C-3);

[0109] Step 2: Add C-3 (20.36 g) to 200 ml THF, stir to dissolve, then add 1,3-dibromo-5,5-dimethylhydantoin (8.55 g), stir for 6-7 hours, and after the reaction is complete, add water to the reaction system for extraction, retain the organic phase, dry it with anhydrous magnesium sulfate, spin dry, pass through a silica gel column, and elute with petroleum ether: ethyl acetate = 10:1, spin dry to obtain 18.51 g of intermediate 7 (C-4).

[0110] MS(MS+1):453.1852.

[0111] Embodiment 1:

[0112]

[0113] D-1 (20.00 g), D-2 (15.64 g), tetrakis(triphenylphosphine)palladium (0.6 g) and sodium tert-butoxide (8.07 g) were added to 200 ml of a mixed solution of toluene (2 V) / ethanol (1 V) / water (1 V). Under nitrogen protection, the reaction system was stirred at 100 degrees Celsius for 4 hours, and then cooled to room temperature. The reaction system was diluted with water (50 ml), extracted with ethyl acetate, the organic phase was retained, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was concentrated to a muddy state, 50 ml of toluene was added, and the mixture was stirred under hot reflux for 2 h, filtered while hot, the organic phase was retained, and the organic phase was spin-dried to obtain (D-3) 25.69 g ( Figure 1 );

[0114] MS(MS+1):556.1587.

[0115] Embodiment 2:

[0116] The D-1 in Example 1 was replaced by 1-bromo-6-(3,5-diphenylphenyl)pyrene, and D-2 and the catalyst, ligand, reaction conditions and post-treatment required for the reaction remained unchanged to synthesize

[0117] MS(MS+1):708.5714.

[0118] Embodiment 3:

[0119] The D-1 in Example 1 was replaced by 1-bromo-6-(3,5-diphenylphenyl)pyrene, and the D-2 was replaced by 7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0120] MS(MS+1):706.5310.

[0121] Embodiment 4:

[0122] The D-1 in Example 1 was replaced by 1-bromo-6-(4-(naphthalen-2-yl)phenyl)pyrene, and D-2 and the catalyst, ligand, reaction conditions and post-treatment required for the reaction remained unchanged to synthesize

[0123] MS(MS+1):682.6911.

[0124] Embodiment 5:

[0125] The D-1 in Example 1 was replaced by 2-(6-bromopyrifo-1-yl)-4,6-diphenyl-1,3,5-triazine, and D-2 was replaced by 7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0126] MS(MS+1):709.6320.

[0127] Embodiment 6:

[0128] The D-1 in Example 1 was replaced by 2-(6-bromopyrifo-1-yl)-4,6-diphenyl-1,3,5-triazine, and the catalyst, ligand, reaction conditions and post-treatment required for D-2 and other reactions remained unchanged to synthesize

[0129] MS(MS+1):711.2410.

[0130] Embodiment 7:

[0131] The D-1 in Example 1 was replaced by 2-(6-bromopyrifo-1-yl)pyridine, and the D-2 was replaced by 7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0132] MS(MS+1):555.9860.

[0133] Embodiment 8:

[0134] The D-1 in Example 1 was replaced by 6-bromo-N, N-bis(4-(tert-butyl)phenyl)pyrene-1-amine, and D-2 was replaced by 7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0135] MS(MS+1):757.9521.

[0136] Embodiment 9:

[0137] The D-1 in Example 1 was replaced by intermediate 8, and D-2 was replaced by 7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0138] MS(MS+1):719.1021.

[0139] Embodiment 10:

[0140] The D-1 in Example 1 was replaced by the intermediate 11, and the D-2 was replaced by 7,7-dimethyl-2-phenyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0141] MS(MS+1):726.7300.

[0142] Embodiment 11:

[0143]

[0144] E-1 (20.00 g), E-2 (22.36 g), tetrakis(triphenylphosphine)palladium (0.6 g) and sodium carbonate (8.90 g) were added to 200 ml of a mixed solution of toluene (2 V) / ethanol (1 V) / water (1 V). Under nitrogen protection, the reaction system was stirred at 85 degrees Celsius for 4 hours, and then cooled to room temperature. The reaction system was diluted with water, extracted with ethyl acetate, the organic phase was retained, the organic phase was dried over anhydrous magnesium sulfate, the organic phase was concentrated to a muddy state, 50 ml of toluene was added, and the mixture was stirred under hot reflux for 2 h, filtered while hot, the organic phase was retained, and the organic phase was spin-dried to obtain E-3, 30.61 g.

[0145] MS(MS+1):632.3001.

[0146] Embodiment 12:

[0147] The E-1 in Example 11 was replaced by the intermediate 7, and the catalyst, ligand, reaction conditions and post-treatment required for D-2 and other reactions remained unchanged to synthesize

[0148] MS(MS+1):863.2134.

[0149] Embodiment 13:

[0150] The E-1 in Example 11 was replaced by 6-bromo-N, N-diphenylpyridine-1-amine, and E-2 was replaced by intermediate 3. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0151] MS(MS+1):799.3741.

[0152] Embodiment 14:

[0153] The E-1 in Example 11 was replaced by 6-bromo-N, N-diphenylpyridine-1-amine, and E-2 was replaced by intermediate 4. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0154] MS(MS+1):721.8471.

[0155] Embodiment 15:

[0156] The E-1 in Example 11 was replaced by Intermediate 9, and E-2 was replaced by Intermediate 4. The catalysts, ligands, reaction conditions and post-treatments required for other reactions remained unchanged.

[0157] MS(MS+1):736.8710.

[0158] Embodiment 16:

[0159] The E-1 in Example 11 was replaced by the intermediate 10, and the E-2 was replaced by the intermediate 1. The catalysts, ligands, reaction conditions and post-treatments required for other reactions remained unchanged.

[0160] MS(MS+1):748.9810.

[0161] Embodiment 17:

[0162] The E-1 in Example 11 was replaced by 1-bromo-6-(phenyl-D5)pyrene, and the E-2 was replaced by (5-((4-tert-butyl)phenyl)(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino)naphthalen-1-yl)boric acid. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0163] MS(MS+1):743.8412.

[0164] Embodiment 18:

[0165]

[0166] F-1 (20.00 g), F-2 (22.16 g), tetrakis(triphenylphosphine)palladium (0.9 g) and sodium tert-butoxide (11.43 g) were added to 200 ml of a mixed solution of toluene (2 V) / ethanol (1 V) / water (1 V). Under nitrogen protection, the reaction system was stirred at 85 degrees Celsius for 4 hours, and then cooled to room temperature. The reaction system was diluted with water, extracted with ethyl acetate, the organic phase was retained, the organic phase was dried with anhydrous magnesium sulfate, the organic phase was concentrated to a muddy state, 50 ml of toluene was added, and the mixture was stirred under hot reflux for 2 hours. The mixture was filtered while hot, and the organic phase was retained. The organic phase was spin-dried and passed through a purification column, eluted with petroleum ether: ethyl acetate = 10:1, and spin-dried to obtain F-3, 20.67 g.

[0167] MS(MS+1):901.3410.

[0168] Embodiment 19:

[0169] The F-1 in Example 18 was replaced by 1,6-dibromo-5,10-di-tert-butylpyrene, and the F-2 was replaced by 7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0170] MS(MS+1):865.1820.

[0171] Embodiment 20:

[0172] The F-1 in Example 18 was replaced by 1,6-dibromo-5,10-phenylpyrene, and the F-2 was replaced by 7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[b]carbazole. The catalysts, ligands, reaction conditions and post-treatments required for the other reactions remained unchanged.

[0173] MS(MS+1):905.3841.

[0174] Example 21: Organic electroluminescent device

[0175] The organic electroluminescent device is prepared by using Example 1, comprising the following steps:

[0176] (1) A glass substrate with a 120 nm ITO transparent film was ultrasonically cleaned with acetone, isopropanol, and deionized water for 10 min each, vacuum dried at 105° C. for 2 h, and then UV ozone cleaned for 15 min. The ITO glass substrate was then transferred to a vacuum evaporator.

[0177] (2) vacuum evaporating molybdenum trioxide (MoO3) on the surface on which the ITO film is formed to form a 10 nm thick hole injection layer;

[0178] (3) Next, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC) was vacuum-deposited on the hole injection layer to form a 70 nm thick hole transport layer;

[0179] (4) Next, on the hole transport layer, 9,10-di(2-naphthyl)anthracene (ADN) (as a light-emitting host material, 95 wt%) and the compound prepared in Synthesis Example 1 (as a light-emitting guest material, 5 wt%) were co-vacuum-deposited to form a light-emitting layer with a thickness of 30 nm.

[0180] (5) Next, 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1"-terphenyl]-3,3"-diyl]bipyridine (TmPyPB) was vacuum-deposited on the light-emitting layer to form an electron transport layer with a thickness of 40 nm;

[0181] (6) Next, lithium fluoride (LiF) is vacuum-deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm;

[0182] (7) Finally, aluminum (Al) was vacuum-deposited on the electron injection layer to form a cathode with a thickness of 100 nm, thereby obtaining device 1.

[0183] Example 22: Organic electroluminescent device

[0184] An organic electroluminescent device was prepared in the same manner as in Example 21, except that the compounds synthesized in Synthesis Example 2 to Synthesis Example 20 were used to replace the compound prepared in Synthesis Example 1, respectively, to obtain devices 2-20.

[0185] Comparative Example:

[0186]

[0187] Device Comparison 1 to Device Comparison 2: Organic electroluminescent devices were prepared in the same manner as device 21, except that the following compounds (G-1) to (G-2) were used to replace the compounds prepared in Synthesis Example 21, respectively.

[0188] The driving voltage, current efficiency, LT95, and glass transition temperature of devices 1-20 and device comparisons 1 to 2 were tested. The testing method was based on the records of patents: CN115433180B and CN118561827B. The results are shown in Table 1:

[0189] Table 1

[0190]

[0191]

[0192] In summary, the HOMO and LUMO energy levels of the organic electroluminescent compound of the present invention have a high degree of matching with the adjacent energy levels, so that the carrier mobility of the organic electroluminescent compound is relatively balanced, thereby making the organic electroluminescent device containing the organic electroluminescent compound have a lower driving voltage, higher luminous efficiency and longer life. Using the organic electroluminescent compound of the present invention as a light-emitting main material can emit higher quality blue light, thereby improving the color expression and visual effect of displays or lighting products.

[0193] Although the embodiments of the present invention have been shown and described above, it is to be understood that the above embodiments are exemplary and are not to be construed as limitations of the present invention. A person skilled in the art may change, modify, replace and vary the above embodiments within the scope of the present invention.

Claims

1. An organic electroluminescent compound, characterized in that: The organic electroluminescent compound is a compound represented by Formula 1: In formula 1, R1-R 10 1-2 of them are connected to L1 and / or L2, and the remaining R1-R 10 The same or different groups are independently selected from any one of the following groups: hydrogen, deuterium, cyano, C1-C 10 Alkyl, C1-C 10 Alkylsilyl, C6-C 12 The aromatic group; In Formula 1, L1-L2 are the same or different and are independently selected from any one of the following: a single bond, a C6-C5 alkyl group that is unsubstituted or substituted with deuterium, a C1-C5 alkyl group, a cyano group, or a nitro group; 15 Arylene, unsubstituted or substituted with deuterium, C1-C5 alkyl, cyano, nitro 12 Heteroarylene; In formula 1, R 11 Any one selected from the following groups: hydrogen, N(R 18 )(R 19 )、C6-C 25 Aryl, C4-C 25 A heteroaryl group, a structure shown in Formula 2; In formula 1, R 12 Selected from the structure shown in Formula 2: In formula 2, R 13 -R 16 The same or different groups are independently selected from the following groups: C1-C 10 The alkyl group; In formula 2, R 17 Selected from the following groups: hydrogen, C1-C 10 alkyl, unsubstituted or substituted with deuterium, C1-C5 alkyl, cyano, nitro 15 The aromatic group; In formula 2 Represents: empty or single key; R 18 -R 19 The same or different groups are independently selected from any one of the following groups: C6-C 25 Aryl, C4-C 25 The heteroaryl group.

2. An organic electroluminescent compound according to claim 1, characterized in that: The structure shown in Formula 1 is selected from any one of the following structures:

3. An organic electroluminescent compound according to claim 1, characterized in that: When L1-L2 is C6-C 15 Arylene or C4-C 12 When the heteroarylene group is L1-L2, the structure is shown in Formula 3: In formula 3 represents the junction site; X1 is selected from at least one of the following groups: CH, CD, N; or two adjacent X1 and phenyl groups form a condensed ring structure through a shared chemical bond.

4. An organic electroluminescent compound according to claim 1, characterized in that: When R 11 Selected from C6-C 25 Aryl, C4-C 25 When the heteroaryl group is 11 The structure shown in Formula 4 or the structure shown in Formula 4 and The fused ring structure is formed by sharing chemical bonds: In formula 4, X 2a -X 2c is selected from the following groups: CH or N; R 20 -R 21 The same or different groups are independently selected from any one of the following groups: hydrogen, cyano, C1-C 10 Alkyl, C6-C 15 Aryl, C6-C 12 Aromatic hetero groups; X3 is selected from the following groups: O, S, C(CH3, CH3), N, NR 22 ; n and m are the same or different and are selected from: 1, 2, 3; * is the connection site; R 22 Selected from the following groups: C6-C 15 The aromatic group.

5. An organic electroluminescent compound according to claim 4, characterized in that: When R 11 Selected from C6-C 25 When the aryl group is 11 The structure is shown in formula 4-1: In formula 4-1, R 23 -R 27 The same or different groups are independently selected from any one of the following groups: hydrogen, deuterium, cyano, C1-C 10 Alkyl, deuterated C1-C 10 an alkyl group containing at least one N-containing six-membered heteroaryl group; or R 23 -R 27 The two adjacent substituents in the formula are connected to —CH=CH—CH=CH— through a common chemical bond to form a condensed ring structure; or R 23 -R 27 The two adjacent substituents in Connected to form a condensed ring structure; When R 11 Selected from C4-C 25 When the heteroaryl group is 11 It is the structure shown in Formula 4-2 or Formula 4-3: Where R 20 -R 22 The same or different groups are independently selected from the following groups: hydrogen, deuterium, C1-C 10 Alkyl, six-membered aryl, six-membered heteroaryl containing at least one N, benzo six-membered aryl, formula 4-3; When R 11 Selected from N(R 18 )(R 19 ), R 11 The structure shown in Formula 5: In formula 5, R 28 -R 33 The same or different groups are independently selected from any one of the following groups: hydrogen, deuterium, cyano, C1-C 10 An alkyl group, a six-membered aryl group; or R 28 -R 33 The two adjacent substituents in the formula are connected to —CH=CH—CH=CH— through a common chemical bond to form a condensed ring structure; or R 28 -R 33 The two adjacent substituents in Connected to form a condensed ring structure; X4 is selected from any of the following groups: O, S, NR 34 ; NR 34 Selected from: phenyl.

6. An organic electroluminescent compound according to any one of claims 1 to 5, characterized in that: R 12 The structure is selected from any one of the following groups: R in Formula 2-1 and Formula 2-2 17 Any one selected from the following groups: hydrogen, deuterium, C1-C5 alkyl, phenyl.

7. An organic electroluminescent compound according to any one of claims 1 to 5, characterized in that: C1-C 10 The alkyl group is selected from: a C1-C5 alkyl group, wherein the hydrogen on the alkyl group is not deuterated or is replaced by at least one deuterium; When R1-R 10 At least one of them is C1-C 10 Alkylsilyl, C1-C 10 The alkylsilyl group is selected from: C1-C5 alkylsilyl group; When R1-R 10 At least one of them is C6-C 12 Aryl, C6-C 12 The aryl group is selected from: phenyl; When R1-R 10 At most 2 substituents are C1-C 10 Alkyl, or / and C1-C 10 Alkylsilyl, or / and C6-C 12 The aromatic group.

8. An organic electroluminescent compound according to any one of claims 1 to 5, characterized in that: The structure of the organic electroluminescent compound is any one of the following:

9. An application of an organic electroluminescent compound, characterized in that: The organic electroluminescent compound according to any one of claims 1 to 8 is used to prepare a luminescent host material or a luminescent guest material.

10. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises an organic material layer, and the organic material layer comprises the organic electroluminescent compound according to any one of claims 1 to 8.

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