Organic electroluminescent material, organic electroluminescent device and application

Abstract

The invention discloses an organic electroluminescent material, an organic electroluminescent device and application. According to the organic electroluminescent material provided by the invention, the conjugation degree is improved by substituting a benzene ring # imgabs0 # at the position 6 of naphthobenzofuran on an LB ligand, the total energy of molecules is obviously reduced, and the stability of the molecules is improved; after the obtained organic electroluminescent material is applied to an organic electroluminescent device, the maximum external quantum efficiency of the device is improved, the service life is prolonged, and the driving voltage is reduced.

Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric materials, and more particularly to an organic electroluminescent material and an organic electroluminescent device and their application. Background Art

[0002] Organic electronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasmonic light-emitting devices.

[0003] In the prior art, small molecule OLEDs are usually produced by vacuum thermal evaporation, or by solution methods if the raw materials can be dissolved or dispersed in a solvent, while polymer OLEDs are prepared by solution methods such as spin coating, inkjet printing, and nozzle printing.

[0004] The luminous color of OLED can be changed by designing the structure of the luminescent material, generally through one or more luminescent layers to achieve the desired color. At present, luminescent materials have been successfully commercialized in green, yellow and red OLEDs. In commercial full-color OLED displays, blue fluorescence and yellow phosphorescence, or a mixture of red phosphorescence and green phosphorescence, are usually used. The device has the disadvantages of short life and high operating voltage. In addition, OLED also has the problem of rapid reduction of luminous efficiency under high brightness.

[0005] Therefore, how to provide a high-performance organic electroluminescent material and an organic electroluminescent device and their applications that enable the organic electroluminescent device to have comprehensive characteristics such as high efficiency, long life and low voltage is a technical problem that people in this field need to solve urgently. Summary of the invention

[0006] In view of this, the present invention provides an organic electroluminescent material and an organic electroluminescent device and application. The organic electroluminescent material provided by the present invention is used as a material in the light-emitting layer of an organic electroluminescent device, so that it can reduce the driving voltage of the device, improve the maximum external quantum efficiency of the device, and extend the phosphorescence life of the device.

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

[0008] An organic electroluminescent material, characterized in that it has a structure shown in Formula I:

[0009]

[0010] Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 Each is independently selected from hydrogen, deuterium, halogen, cyano, isocyano, silanyl, germyl, -CD3, -CD2CD3, -(CD3)3, -F, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, methoxy, ethoxy, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, and the following groups, and combinations thereof:

[0011]

[0012] The hydrogen atoms in the above groups are partially or completely deuterated.

[0013] In the present invention, the above-mentioned "substituted or unsubstituted" means substituted by one, two or more substituents selected from the following: deuterium; halogen group; cyano group; C1-C6 alkyl group; C3-C10 cycloalkyl group; alkoxy group; C6-C18 aryl group; C3-C24 heterocyclic group, or substituted by two or more substituents connected to each other among the substituents shown above, or having no substituent.

[0014] Preferably, the formula I is selected from any one of the following structural formulas Ia, Ib, Ic, Id, Ie, If, Ig, Ih, and Ii:

[0015]

[0016] Preferably, all of R5, R6, R7, and R8 are hydrogen or only one of them is not hydrogen. A Ligand Select from any of the following structures:

[0017]

[0018]

[0019]

[0020] Preferably, L B Ligand Select from any of the following structures:

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027] Preferably, the formula I is selected from any one of the following compounds:

[0028]

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[0155] Only some specific structural forms are listed above, but this series of organic electroluminescent materials is not limited to the above molecular structures. Other specific molecular structures can be obtained by simple changes of some simple groups and their substituted groups and substitution positions, which will not be described one by one here.

[0156] Another object of the present invention is to provide an organic electroluminescent device, the organic electroluminescent device comprising: an anode, a cathode and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the above-mentioned organic electroluminescent material;

[0157] The organic electroluminescent material is in a single form or mixed with other substances and exists in the organic layer.

[0158] Preferably, the organic layer comprises at least 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 light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a layer having both electron transport and electron injection functions;

[0159] The light-emitting layer includes the above-mentioned organic electroluminescent material.

[0160] Preferably, the light-emitting layer includes a main material and a doping material, the doping material is the above-mentioned organic electroluminescent material, and the mixing ratio of the main material to the doping material is 90:10 to 99.5:0.5.

[0161] Another object of the present invention is to provide the use of the above-mentioned organic electroluminescent device in an organic light-emitting device, an organic solar cell, an electronic paper, an organic photoreceptor or an organic thin film transistor.

[0162] It can be seen from the above technical solution that compared with the prior art, the present invention has the following beneficial effects:

[0163] By introducing a substituted benzene ring at the 6th position of naphthobenzofuran on the LB ligand The degree of conjugation is improved, the total energy of the molecule is significantly reduced and its stability is increased; after the obtained organic electroluminescent material is used in an organic electroluminescent device, the external quantum efficiency of the device is improved, the life span is delayed, and the driving voltage is reduced. BRIEF DESCRIPTION OF THE DRAWINGS

[0164] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on the provided drawings without paying creative work.

[0165] Figure 1 The figure is the hydrogen nuclear magnetic resonance spectrum of compound G-98 of the present invention. DETAILED DESCRIPTION

[0166] The technical solutions in the embodiments of the present invention are described clearly and completely below. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0167] Example 1: Preparation of G-34

[0168]

[0169] Step 1: Weigh 8-chloro-6-phenylnaphtho[2,1-b]benzofuran (1eq), bipyraclostrobin (2eq), potassium acetate (3eq), 1,4-dioxane (15eqml), replace nitrogen, add tris(dibenzyl ketone)dipalladium (2%eq) and X-Phos (10%eq) to the reaction system under nitrogen protection, react at 100°C for 12 hours, concentrate, and dry. Column chromatography, petroleum ether and dichloromethane as eluents, to obtain intermediate S1 with a yield of 78.12%.

[0170] HPLC: ≥99.3%;

[0171] Mass spectrometry test value 420.24.

[0172]

[0173] Step 2: First weigh the intermediate S1 (1.2 eq), 2-bromopyridine (1 eq), anhydrous potassium carbonate (3 eq), toluene (10 eq), ethanol (5 eq), water (10 eq), replace nitrogen twice, add (triphenylphosphine) palladium (2% eq) to the reaction system under nitrogen protection, react at 100°C for 12 hours, and the reaction is complete. Stand and separate, extract the aqueous phase with ethyl acetate, combine the organic phases, spin dry, column chromatography, petroleum ether and ethyl acetate as eluents, and obtain the intermediate S2 with a yield of 75.26%.

[0174] HPLC: ≥99.5%;

[0175] Mass spectrometry test value 371.40.

[0176]

[0177] Step 3: First weigh 2-chloro-4-isobutyl-5-(trimethylsilyl)pyridine (1 eq), 3,5-dimethylphenylboronic acid (1.1 eq), anhydrous potassium carbonate (3 eq), toluene (10 eq), ethanol (5 eq), and water (10 eq), replace the nitrogen, and add tetrakis(triphenylphosphine)palladium (1% eq) to the reaction system under nitrogen protection, react at 100°C for 12 hours, then cool to room temperature, stand and separate, combine the organic phases, spin dry, and column chromatography, using petroleum ether and dichloromethane as eluents to obtain intermediate S3 with a yield of 73.10%.

[0178] HPLC: ≥99.8%;

[0179] Mass spectrometry test value 283.25.

[0180]

[0181] Step 4: Under nitrogen protection, weigh the intermediate S3 (2.2 eq) and IrC13·3H2O (1 eq) into the reaction system, add a mixed solution of ethylene glycol ethyl ether (12 eq) and purified water (3 eq), reflux for 48 hours under nitrogen protection, then cool to room temperature, precipitate, filter the precipitate, rinse and dry with water, anhydrous ethanol, and petroleum ether in turn. The bridged ligand A-34 is obtained with a yield of 84.94%.

[0182] Step 5: Weigh the bridging ligand A-34 (1 eq), add silver trifluoromethanesulfonate (2.2 eq), then add dichloromethane (15 eq) to the system, add methanol (3 eq), react at room temperature for 48 hours under nitrogen protection, pass through a funnel, and spin dry to obtain the bridging ligand B-34 with a yield of 83.97%.

[0183] Step 6: Weigh the bridging ligand B-34 (1 eq), add the intermediate S3 (2.5 eq), and then add anhydrous ethanol (20 eq) to the system. Under nitrogen protection, reflux for 48 hours, filter, wash with alcohol, and dry. Use a mixture of petroleum ether and dichloromethane as a developing solvent, column chromatography, concentrate the filtrate, and solid precipitate to obtain the organic electroluminescent material G-34 with a yield of 35.92%.

[0184] HPLC:≥99.3%.

[0185] Mass spectrometry test value 1155.52.

[0186] Elemental Analysis:

[0187] Theoretical value: C, 67.56%; H, 5.93%; N, 3.64%; O, 1.38%; Si, 4.86%;

[0188] Test values: C, 67.61%; H, 5.96%; N, 3.63%; O, 1.36%; Si, 4.88%.

[0189] 1 H NMR (400 MHz, deuterated chloroform) δ8.71 (dd, 1H), 8.36 (s, 2H), 8.22 (dt, 1H), 8.08 (d, 1H), 7.91 (ddd, 2H), 7.84 (t, 3H), 7.75 (td, 1H), 7.67 (d, 1H), 7.66-7.60 (m, 2H), 7.55 (s, 2H), 7.52-7.39 (m, 4H), 7.35-7.29 (m, 1H), 7.29-7.22 (m, 5H), 2.75 (d, 4H), 2.42 (s, 6H), 1.91 (dtt, 2H), 0.85 (d, 12H), 0.46 (s, 18H).

[0190] Example 2: Preparation of G-71

[0191]

[0192] The first step: first weigh 8-chloro-6-phenylnaphtho[2,1-b]benzofuran (1eq), 3-isopropyl-2-pyridineboronic acid (1.2eq), anhydrous potassium carbonate (3eq), toluene (10eq), ethanol (5eq), and water (5eq), replace the nitrogen, add tetrakis(triphenylphosphine)palladium (2%eq) to the reaction system under nitrogen protection, react at 85°C for 12 hours, then cool to room temperature, stand and separate, combine the organic phases, spin dry, column chromatography, use petroleum ether and dichloromethane as eluents, and obtain intermediate S4 with a yield of 68.7%.

[0193] HPLC: ≥99.5%;

[0194] Mass spectrometry test value: 413.22.

[0195]

[0196] Step 2: Weigh 2-bromo-5-methylpyridine (1 eq), 4-methylphenylboronic acid (1.1 eq), anhydrous potassium carbonate (3 eq, toluene (10 eq), ethanol (5 eq), and water (10 eq), replace nitrogen, add (tetrakistriphenylphosphine) palladium (3% eq) to the reaction system under nitrogen protection, react at 100°C for 12 hours, then cool to room temperature, stand for separation, combine the organic phases, spin dry, column chromatography, and use petroleum ether and dichloromethane as developing agents to obtain intermediate S5 with a yield of 76.04%.

[0197] HPLC: ≥99.6%;

[0198] Mass spectrometry test value 183.10.

[0199]

[0200] Step 3: Under nitrogen protection, weigh the intermediate S5 (2.5 eq) and IrC13·3H2O (1 eq) into the reaction system, add a mixed solution of ethylene glycol ethyl ether (12 eq) and purified water (4 eq), reflux for 48 hours under nitrogen protection, then cool to room temperature, precipitate, filter the precipitate, rinse and dry with water, anhydrous ethanol, and petroleum ether in turn. The bridged ligand A-71 is obtained with a yield of 77.33%.

[0201] Step 4: Weigh the bridging ligand A-71 (1 eq), add silver trifluoromethanesulfonate (2.2 eq), then add dichloromethane (12 eq) to the system, add methanol (3 eq), react at room temperature for 48 hours under nitrogen protection, pass through a funnel, and spin dry to obtain the bridging ligand B-71 with a yield of 78.43%.

[0202] Step 5: Weigh the bridge ligand B-71 (1 eq), add the ligand S4 (2.5 eq), and then add anhydrous ethanol (20 eq) to the system. Under nitrogen protection, reflux for 48 hours, filter, wash with alcohol, and dry. Petroleum ether and dichloromethane are used as eluents, column chromatography, and the filtrate is concentrated to precipitate solids to obtain the organic electroluminescent material G-71 with a yield of 42.3%.

[0203] HPLC:≥99.3%.

[0204] Mass spectrometry test value: 969.38.

[0205] Elemental analysis: theoretical value C, 69.40%; H, 4.78%; N, 4.34%; O, 1.65%; tested value C, 69.47%; H, 4.79%; N, 4.31%; O, 1.63%.

[0206] 1 H NMR (400 MHz, deuterated chloroform) δ 8.69 (d, 1H), 8.47 (d, 2H), 8.22 (dt, 1H), 8.09 (d, 1H), 7.93-7.88 (m, 1H), 7.84 (d, 1H), 7.82-7.78 (m, 2H), 7.73-7.66 (m, 3H), 7.66-7.60 (m, 4H), 7.59-7.55 (m, 1H), 7.53-7.41 (m, 3H), 7.41-7.31 (m, 2H), 7.24 (d, 4H), 7.20 (dd, 1H), 3.10-3.02 (m, 1H), 2.42 (s, 6H), 2.25 (d, 6H), 1.28 (d, 6H).

[0207] Example 3: Preparation of G-98

[0208]

[0209] The first step: first weigh 8-chloro-6-phenylnaphtho[2,1-b]benzofuran (1eq), 3-methyl-2-pyridineboronic acid (1.2eq), anhydrous potassium carbonate (3eq), toluene (10eq), ethanol (5eq), and water (5eq), replace the nitrogen, add tetrakis(triphenylphosphine)palladium (2%eq) to the reaction system under nitrogen protection, react at 85°C for 12 hours, then cool to room temperature, stand and separate, combine the organic phases, spin dry, and column chromatography, using petroleum ether and dichloromethane as eluents to obtain intermediate S6 with a yield of 67.3%.

[0210] HPLC: ≥99.5%.

[0211]

[0212] Step 2: First weigh the intermediate S6 (1 eq) and sodium tert-butoxide (1.2 eq) and add them to a three-necked flask, replace nitrogen twice, add deuterated dimethyl sulfoxide (18 eq) under nitrogen protection, react at 85°C for 48 hours, and the reaction is complete. Add 20 ml of saturated sodium chloride solution, 30 ml of ethyl acetate, and 20 ml of water to the system, stir for 30 minutes, stand and separate, extract the aqueous phase with ethyl acetate 3 times, combine the organic phases and spin dry, column chromatography, use dichloromethane and ethyl acetate as eluents, and obtain the intermediate S7 with a yield of 50.74%.

[0213] HPLC: ≥99.6%.

[0214]

[0215] Step 3: first weigh 2-bromo-4,,5-dimethylpyridine (1eq), 3,4-dimethylphenylboronic acid 1.2eq), anhydrous potassium carbonate (3eq), toluene (10eq), ethanol (5eq), and water (10eq), replace nitrogen, add (tetrakistriphenylphosphine)palladium (3%eq) to the reaction system under nitrogen protection, react at 100°C for 12 hours, then cool to room temperature, stand and separate, combine the organic phases, spin dry, column chromatography, and use petroleum ether and dichloromethane as developing agents to obtain intermediate S8 with a yield of 73.62%.

[0216] HPLC: ≥99.8%;

[0217] Mass spectrometry test value 211.14.

[0218]

[0219] Step 4: Weigh the intermediate S8 (1 eq) and sodium tert-butoxide (2 eq) and add them to the reaction system. Add deuterated dimethyl sulfoxide (40 eq) under nitrogen protection, react at 85°C for 48 hours, and the reaction is complete. Add 30 ml of saturated sodium chloride solution, 30 ml of ethyl acetate, and 30 ml of water to the system, stir for 30 minutes, stand for separation, then cool to room temperature, stand for separation, combine the organic phases, spin dry, column chromatography, and use dichloromethane and ethyl acetate as eluents to obtain intermediate S9 with a yield of 52.79%.

[0220] HPLC: ≥99.8%.

[0221]

[0222] Step 5: Under nitrogen protection, weigh the intermediate S9 (2.2 eq) and IrC13·3H2O (1 eq) into the reaction system, add a mixed solution of ethylene glycol ethyl ether (12 eq) and purified water (4 eq), reflux for 24 hours under nitrogen protection, then cool to room temperature, precipitate is precipitated, filter the precipitate, rinse and dry with water, anhydrous ethanol, and petroleum ether in turn. The bridged ligand A-98 is obtained with a yield of 75.78%.

[0223] Step 6: Weigh the bridging ligand A-98 (1 eq), add silver trifluoromethanesulfonate (2.2 eq), then add dichloromethane (15 eq) and methanol (3 eq) to the system, react at room temperature for 48 hours under nitrogen protection, pass through a funnel, and spin dry to obtain the bridging ligand B-98 with a yield of 81.74%.

[0224] Step 7: Weigh the bridged ligand B-98 (1 eq), add the intermediate S7 (2.5 eq), and then add anhydrous ethanol (20 eq) to the system. Under nitrogen protection, reflux for 48 hours, filter, wash with alcohol, and dry. Use dichloromethane and petroleum ether as developing solvents, column chromatography, concentrate the filtrate, and solid precipitate to obtain the organic electroluminescent material G-98 with a yield of 32.06%.

[0225] HPLC:≥99.1%.

[0226] Mass spectrometry test value 1024.86.

[0227] H NMR spectrum see Figure 1 .

[0228] Elemental analysis: theoretical value C, 68.00%; H, 7.57%; N, 4.10%; O, 1.56%; tested value C, 68.06%; H, 7.58%; N, 4.08%; O, 1.53%.

[0229] Example 4: Preparation of G-316

[0230]

[0231] Step 1: Weigh the intermediate S4 (1 eq) and sodium hydroxide (1.2 eq), replace nitrogen twice, add deuterated dimethyl sulfoxide (18 eq) to the reaction system under nitrogen protection, reflux at 80°C for 48 hours, and the reaction is completed. Cool to room temperature, stand and separate, extract the aqueous phase with ethyl acetate, spin dry the organic phase, column chromatography, dichloromethane and ethyl acetate as eluents, and obtain the intermediate S10 with a yield of 53.29%.

[0232] HPLC: ≥99.8%.

[0233]

[0234] Step 2: First weigh 2-bromopyridine (1 eq), 4-isopropylphenylboronic acid (1.2 eq), anhydrous potassium carbonate (3 eq), toluene (10 eq), ethanol (5 eq), and water (10 eq), replace the nitrogen, add (tetrakistriphenylphosphine)palladium (3% eq) to the reaction system under nitrogen protection, react at 100°C for 12 hours, then cool to room temperature, stand and separate the liquids, extract the aqueous phase with ethyl acetate, combine the organic phases, spin dry, and perform column chromatography, using petroleum ether and dichloromethane as eluents to obtain intermediate S11 with a yield of 59.36%.

[0235] HPLC: ≥99.6%;

[0236] Mass spectrometry test value: 197.24.

[0237]

[0238] Step 3: Under nitrogen protection system, weigh the intermediate S11 (2.2 eq), IrC13·3H2O (1 eq), ethylene glycol ether (12 eq), and water (4 eq) and add them into a three-necked flask, replace nitrogen twice, reflux for 48 hours, and then cool to room temperature. A precipitate is precipitated, and the precipitate is filtered, washed and dried with water, anhydrous ethanol, and petroleum ether in turn. Intermediate A-316 is obtained with a yield of 72.55%.

[0239] Step 4: Weigh the intermediate A-316 (1 eq), add silver trifluoromethanesulfonate (2.2 eq), then add dichloromethane (15 eq) to the system, add methanol (3 eq), react at room temperature for 48 hours under nitrogen protection, pass through a funnel, and spin dry to obtain the intermediate B-316 with a yield of 82.69%.

[0240] Step 5: Weigh the intermediate B-316 (1 eq), add the intermediate S10 (2.5 eq), and then add anhydrous ethanol (20 eq) to the system. Under nitrogen protection, reflux for 48 hours, filter, wash with alcohol, and dry. Use dichloromethane as solvent, column chromatography, concentrate the filtrate, and solid precipitate to obtain the organic electroluminescent material G-316 with a yield of 41.97%.

[0241] HPLC:≥99.3%.

[0242] Mass spectrometry test value 998.45.

[0243] Elemental analysis: theoretical value C, 69.78%; H, 5.15%; N, 4.21%; O, 1.60%; tested value C, 69.82%; H, 5.17%; N, 4.20%; O, 1.58%.

[0244] 1 H NMR (400 MHz, deuterated chloroform) δ 8.80-8.53 (m, 3H), 8.22 (dt, 1H), 8.10 (d, 1H), 7.93-

[0245] 7.79(m,6H),7.76-7.60(m,6H),7.52-7.38(m,6H),7.35-7.29(m,1H),7.29-7.19(m,5H),3.17-2.95(m,2H),1.41-1.14(m,18H).

[0246] The synthesis methods of other organic electroluminescent materials G-1, G-12, G-18, G-27, G-42, G-48, G-80, G-100, G-128, G-136, G-164, G-145, G-177, G-589, G-596, G-630, G-658, G-1251, G-1252, G-1253, G-1254 and G-1255 are the same as those in the above embodiments, and are not described in detail here. The molecular formulas or mass spectra of other synthesized organic electroluminescent materials are shown in Table 1 below:

[0247] Table 1 Molecular formula or mass spectrum of organic electroluminescent materials

[0248] Compound Molecular formula Mass spectrometry test value G-1 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 32 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 871.31 G-12 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 53 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 10 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 937.28 G-18 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 53 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 10 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 937.31 G-27 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 53 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 12 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 939.29 G-42 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 67 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 1125.58 G-48 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 57 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 1007.45 G-80 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 56 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 987.42 G-100 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 68 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 1139.61 G-128 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 57 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 32 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 16 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 999.41 G-136 <![CDATA[C 66 H 69 DIrN3OSi2]]> 1170.51 G-164 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 54 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 36 <h2 style=";text-align:left;direction:ltr"> D6IrN3O]]><h2 style=";text-align:left;direction:ltr"> 947.45 G-145 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 69 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 38 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 1153.48 G-177 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 55 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 32 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 12 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 967.38 G-589 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 58 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 40 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 10 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 1007.42 G-596 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 58 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 32 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 1015.47 G-630 <![CDATA[C 55 H 25 D 18 FIrN3O]]> 991.35 G-658 <![CDATA[C 53 H 27 D 12 FIrN3O]]> 957.16 G-1251 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 64 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 35 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 19 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 1092.55 G-1252 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 56 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 34 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 12 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 981.52 G-1253 <![CDATA[C 53 A 34 F6IrN3O]]> 1035.22 G-1254 <h2 style=";text-align:left;direction:ltr"><![CDATA[C <h2 style=";text-align:left;direction:ltr"> 61 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 46 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 10 <h2 style=";text-align:left;direction:ltr"> IrN3O]]><h2 style=";text-align:left;direction:ltr"> 1049.51 G-1255 <![CDATA[C 59 H 48 D4IrN3O]]> 1015.79

[0249] Example 5: Fabrication of an organic electroluminescent device containing organic electroluminescent material G-34

[0250] The ITO glass substrate with a coating thickness of 150nm was cleaned twice in distilled water and ultrasonically washed for 30 minutes, and then repeatedly cleaned twice with distilled water and ultrasonically washed for 10 minutes. After the distilled water cleaning, ultrasonically washed with isopropyl alcohol, acetone, methanol and other solvents in sequence, and then dried and transferred to a plasma cleaning machine. The above substrate was washed for 5 minutes and sent to a vapor deposition machine.

[0251] First, 60 nm of 4,4',4"-tri[2-naphthylphenylamino]triphenylamine ("2-TNATA") was vacuum-deposited on the ITO (anode) as a hole injection layer; then 60 nm of N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB) was vacuum-deposited on the hole injection layer as a hole transport layer; and a light-emitting layer was vacuum-deposited on the hole transport layer. Among them, the main material of the light-emitting layer 4,4'-N,N'-biphenyl dicarbazole (CBP) and the doping material compound G-34 were in a weight ratio of 90:1 0 mixed and evaporated 30nm to form a light-emitting layer; then vacuum evaporated 10nm thick BAlq to form a hole blocking layer; then vacuum evaporated 40nm thick BCP on the hole blocking layer as an electron transport layer; then vacuum evaporated 0.2nm thick LiF on it as an electron injection layer; and then vacuum evaporated 150nm thick Al on the electron injection layer as a cathode. This method is used to prepare an electroluminescent device. Under the condition of a certain brightness, the performance and luminescence characteristics of the obtained electroluminescent device are tested to evaluate the driving voltage, maximum external quantum efficiency and phosphorescence lifetime.

[0252] The material structure used in the device of the present invention is as follows:

[0253]

[0254] Comparative Example:

[0255] An organic electroluminescent device was prepared in the same manner as in Example 5, except that the light-emitting layer doping material G-34 was replaced with compound 1-6, the structure of which is as follows:

[0256]

[0257] The prepared organic electroluminescent device was subjected to the same tests as those in device example 1. The results are shown in Table 2.

[0258] Table 2 Test results of organic electroluminescent devices

[0259]

[0260]

[0261] As can be seen from Table 2, by replacing the benzene ring at position 6 of naphthobenzofuran on the LB ligand The degree of conjugation is improved, the overall energy of the molecule is significantly reduced and its stability is increased;

[0262] 1) Compared with the electroluminescent devices prepared by using Compounds 1 and 2 as doping materials for the light-emitting layer, the organic electroluminescent devices prepared by using Compounds G-34, G-71, G-98, and G-316 provided by the present invention as doping materials for the light-emitting layer have significantly lower driving voltage, improved maximum external quantum efficiency, and significantly improved lifespan.

[0263] 2) The organic electroluminescent devices prepared using the compounds G-136, G-164, G-1251, G-1252, G-1253, G-1254, and G-1255 provided by the present invention as the light-emitting layer doping materials have a significantly lower driving voltage, an improved external quantum efficiency, and a significantly improved lifespan compared to the electroluminescent devices prepared using the compounds 3, 4, 5, and 6 as the light-emitting layer doping materials.

[0264] In this specification, each embodiment is described in a progressive manner, and each embodiment focuses on the differences from other embodiments. The same or similar parts between the embodiments can be referred to each other. For the device disclosed in the embodiment, since it corresponds to the method disclosed in the embodiment, the description is relatively simple, and the relevant parts can be referred to the method part.

[0265] The above description of the disclosed embodiments enables one skilled in the art to implement or use the present invention. Various modifications to these embodiments will be 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 will not be limited to the embodiments shown herein, but rather to the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. An organic electroluminescent material, characterized in that: It has the structure shown in Formula I: Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 Each is independently selected from hydrogen, deuterium, halogen, cyano, isocyano, silanyl, germyl, -CD3, -CD2CD3, -(CD3)3, -F, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, methoxy, ethoxy, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, and the following groups, and combinations thereof: The hydrogen atoms in the above groups are partially or completely deuterated.

2. An organic electroluminescent material according to claim 1, characterized in that: The formula I is selected from any one of the following structural formulas Ia, Ib, Ic, Id, Ie, If, Ig, Ih, and Ii:

3. An organic electroluminescent material according to claim 2, characterized in that: All of R5, R6, R7 and R8 are hydrogen or only one of them is not hydrogen.

4. The organic electroluminescent material according to claim 1, characterized in that: L A Ligand Select from any of the following structures:

5. The organic electroluminescent material according to claim 1, characterized in that: L B Ligand Select from any of the following structures:

6. The organic electroluminescent material according to claim 1, characterized in that: The formula I is selected from any one of the following compounds:

7. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises: an anode, a cathode and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the organic electroluminescent material according to any one of claims 1 to 6; The organic electroluminescent material is in a single form or mixed with other substances and exists in the organic layer.

8. The organic electroluminescent device according to claim 7, characterized in that: The organic layer at least 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 light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a layer having both electron transport and electron injection functions; The light-emitting layer comprises the organic electroluminescent material according to any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 8, characterized in that: The light-emitting layer comprises a main material and a doping material, wherein the doping material is the organic electroluminescent material according to any one of claims 1 to 6, and the mixing ratio of the main material to the doping material is 90:10 to 99.5:0.

5.

10. Use of the organic electroluminescent device according to claim 9 in an organic light-emitting device, an organic solar cell, an electronic paper, an organic photoreceptor or an organic thin film transistor.

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