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CN113528123B - Host material and organic electroluminescent device comprising same - Google Patents

Host material and organic electroluminescent device comprising same Download PDF

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Publication number
CN113528123B
CN113528123B CN202111083512.5A CN202111083512A CN113528123B CN 113528123 B CN113528123 B CN 113528123B CN 202111083512 A CN202111083512 A CN 202111083512A CN 113528123 B CN113528123 B CN 113528123B
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compound
layer
organic electroluminescent
electroluminescent device
host material
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CN113528123A (en
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高春吉
赵晓宇
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Zhejiang Huadisplay Optoelectronics Co Ltd
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  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present invention provides a host material and an organic electroluminescent device comprising the same, the host material comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by formula 1 below and the second host compound is represented by formula 2 below:
Figure DEST_PATH_IMAGE001

Description

Host material and organic electroluminescent device comprising same
Technical Field
The present invention relates to a host material, and more particularly, to a host material and an organic electroluminescent device including the same.
Background
With the development of multimedia technology and the increase of information-oriented requirements, the requirements for the performance of panel displays are increasing. Among them, organic electroluminescent devices (e.g., OLEDs) have a series of advantages such as self-luminescence, low-voltage dc driving, full curing, wide viewing angle, rich color, etc., and have a wide application prospect due to their potential applications in display and lighting technologies. The organic electroluminescent device is a spontaneous light emitting device, and the OLED light emitting mechanism is that under the action of an external electric field, electrons and holes are respectively injected from a positive electrode and a negative electrode and then migrate, recombine and attenuate in an organic material to generate light. A typical structure of an OLED comprises one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer and an organic light emitting layer.
Although the research on organic electroluminescence is rapidly progressing, there are still many problems to be solved, such as the improvement of External Quantum Efficiency (EQE), the design and synthesis of new materials with higher color purity, the design and synthesis of new materials with high efficiency electron transport/hole blocking, and the like. For the organic electroluminescent device, the luminous quantum efficiency of the device is the comprehensive reflection of various factors and is an important index for measuring the quality of the device.
Luminescence can be divided into fluorescence and phosphorescence. In fluorescence emission, an organic molecule in a singlet excited state transits to a ground state, thereby emitting light. On the other hand, in phosphorescence, organic molecules in a triplet excited state transition to a ground state, thereby emitting light.
At present, some organic electroluminescent materials have excellent performance and certain application value, but as a host material in an organic electroluminescent device, the host material has good hole transport performance except that the triplet state energy level is higher than that of a guest material, and energy reverse transfer for exciton transition release is prevented. Currently, materials having both a high triplet level and good hole mobility in the host material are still lacking. Therefore, how to design a new host material with better performance is a problem to be solved by those skilled in the art.
Disclosure of Invention
In order to overcome the disadvantages of the prior art, it is an object of the present invention to provide a host material and an organic electroluminescent device including the same, which has excellent luminous efficiency and lifetime.
In order to realize the purpose of the invention, the technical scheme of the invention is as follows:
the present invention provides a host material comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by formula 1 below and the second host compound is represented by formula 2 below:
Figure 355557DEST_PATH_IMAGE001
Figure 662910DEST_PATH_IMAGE002
。
in the above structural formula, Ar1、Ar2、Ar3、Ar4And Ar5Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
X1、X2、X3and X4Each independently selected from carbon or nitrogen;
Y1and Y2Each independently selected from NR1Or oxygen (O), wherein R1Is substituted or unsubstitutedC1-C20 alkyl, substituted or unsubstituted C6-30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
L1and L2Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group.
Preferably, the first host compound is represented by any one of the following formulae 1-1 to 1-4:
Figure 973806DEST_PATH_IMAGE003
Figure 572277DEST_PATH_IMAGE004
Figure 573600DEST_PATH_IMAGE005
Figure 537008DEST_PATH_IMAGE006
wherein Ar is1、Ar2And Ar3Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
X1is carbon or nitrogen;
R1is substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
L1is a single bond, a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C3-C30 heteroarylene group;
more preferably, the first host compound is any one of, but not limited to:
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Figure 986630DEST_PATH_IMAGE008
Figure 796454DEST_PATH_IMAGE009
Figure 242348DEST_PATH_IMAGE010
Figure 262256DEST_PATH_IMAGE011
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。
preferably, the second host compound is represented by any one of the following formulae 2-1 to 2-20:
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wherein Ar is1、Ar4And Ar5Each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
X1is carbon or nitrogen;
R1is substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-30 aryl or substituted or unsubstituted C3-C30 heteroaryl;
L2is a single bond, a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C3-C30 heteroarylene group;
more preferably, the second host compound is any one of, but not limited to:
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the invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic functional layer, wherein the organic functional layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, and the organic functional layer contains the host material.
Preferably, the organic functional layer is a light-emitting layer, and the light-emitting layer further contains a dopant.
More preferably, the mass ratio of the host material to the dopant is 10:1 to 100: 1.
More preferably, the mass ratio of the first host compound to the second host compound in the host material is 1:9 to 9: 1.
The invention also provides application of the main body material in an organic electroluminescent device.
Preferably, the organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode deposited in sequence, and the organic compound is used as a host material of the light emitting layer.
Preferably, the organic light emitting device comprises an anode, a cathode and a plurality of organic functional layers located between the anode and the cathode, wherein the organic functional layers contain the one or more compounds.
The invention provides a host material, which comprises at least one first host compound and at least one second host compound, wherein an electron-rich heterocyclic chain structure in the host compound structure has great influence on the photoelectric properties of the whole compound molecule, and is beneficial to reducing unnecessary vibration energy loss, so that high-efficiency light emission is realized. By adjusting substituent groups, the complex has better thermal stability and chemical properties. In addition, the preparation method of the various main compounds is simple, the raw materials are easy to obtain, and the industrial requirements can be met.
The host compound disclosed by the invention is prepared into a device, and particularly used as a host material, the device has the advantages of low driving voltage, high luminous efficiency and the like, and is obviously superior to the conventional common OLED device.
Detailed Description
The organic electroluminescent device of the present invention preferably comprises an anode, a cathode and a plurality of organic functional layers located between the anode and the cathode. The term "organic functional layer" refers to all layers disposed between an anode and a cathode in an organic electroluminescent device, and the organic functional layer may be a layer having a hole property and a layer having an electron property, for example, the organic functional layer includes one or more of a hole injection layer, a hole transport layer, a hole injection and transport functional layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron transport and injection functional layer.
The hole injection layer, the hole transport layer, and the functional layer having both hole injection and hole transport properties of the present invention may include an electron-generating substance in addition to a conventional hole injection substance, a conventional hole transport substance, and a substance having both hole injection and hole transport properties. For example, the organic functional layer is an emissive layer, and the emissive layer includes one or more of phosphorescent hosts, fluorescent hosts, phosphorescent dopants, and fluorescent dopants. The compound for the organic electroluminescent device can be used as a fluorescent main body, can also be used as fluorescent doping, and can be used as the fluorescent main body and the fluorescent doping at the same time.
The light-emitting layer of the present invention may be a red, yellow or blue light-emitting layer. And when the luminescent layer is a red luminescent layer, the compound for the organic electroluminescent device is used as a red main body, so that the organic electroluminescent device with high efficiency, high resolution, high brightness and long service life can be obtained.
The organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially deposited, wherein the red phosphorescent compound is used as a host material of the light-emitting layer.
The method for preparing the organic electroluminescent device of the present invention is not particularly limited, and other methods and materials for preparing the organic electroluminescent device known to those skilled in the art may be used in addition to the host compound represented by formula 1.
Examples
Example 1: synthesis of Compound 1-1
Figure 258772DEST_PATH_IMAGE441
(1) Synthesis of intermediate 1-1-2
After compound 1-1-1(85.0g, 310mmol) was dissolved in 1,4-dioxane (800mL), 2- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline (81.5g, 372mmol), Pd (PPh) were added thereto3)4(18g, 15.5mmol) and K2CO3(128g, 930mmol) of the saturated solution, and the resultant was stirred at 100 ℃ for 6 hours. After the reaction was terminated, the resultant was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was MgSO4Dried, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as developing agents to obtain the objective compound 1-1-2(53.3g, yield: 60%). LC-MS: M/Z286.11 (M)+)。
(2) Synthesis of intermediates 1-1-3
After dissolving compound 1-1-2(80.8, 282mmol) by adding tetrahydrofuran, triethylamine (118mL, 846mmol) and 4-bromobenzoyl chloride (4-bromobenzoyl chloride) (92g, 423mmol) were added thereto at 0 ℃ and the resultant was stirred at room temperature for 1 hour. After the reaction was terminated, the resultant was extracted with distilled water and ethyl acetate. The organic layer was MgSO4Dried, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as developing agents to obtain the objective compound 1-1-3(112.5g, yield: 85%). LC-MS: M/Z468.05 (M)+)。
(3) Synthesis of intermediates 1-1-4
After dissolving Compound 1-1-3(125.3g, 267mmol) in nitrobenzene (nitrobenzene)After neutralization, POCl was added thereto3(37.4mL, 400.5mmol), and the resulting mass was stirred at 150 ℃ for 6 hours. After the reaction was terminated, the resultant was neutralized at room temperature, and then extracted with distilled water and dichloromethane. The organic layer was MgSO4Dried, and then filtered and concentrated. The concentrated residue was stirred with ethyl acetate and then filtered to obtain the objective compound 1-1-4(62.7g, yield: 52%). LC-MS: M/Z450.04 (M +).
(4) Synthesis of Compound 1-1:
the intermediate 1-1-4 (45.1 g, 100mmol), N-phenyl- [1,1' -biphenyl, was added to the reaction vessel]-4-amine (24.5g, 100mmol), tris (dibenzylideneacetone) dipalladium (3.7g, 4mol%), tri-tert-butylphosphine (1.6g, 8mol%), potassium tert-butoxide (38g, 336mmol) and o-xylene (800 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then purified by column chromatography to give compound 1-1(46.2g, yield: 75%). LC-MS: M/Z615.74 (M)+)。
Example 2: synthesis of Compounds 2-54
Figure 709476DEST_PATH_IMAGE442
Figure 45779DEST_PATH_IMAGE443
Compounds 2 to 54 were synthesized by the method of reference example 1, and the other steps referred to the synthesis of compound 1-1 gave compounds 2 to 54 (42.3g, yield: 56%). LC-MS: M/Z755.26 (M)+)。
Example 3: synthesis of Compounds 2-69
Figure 286136DEST_PATH_IMAGE444
Figure 329179DEST_PATH_IMAGE445
Compound 2-69 was synthesized by the method of reference example 1, and the other steps referred to the synthesis of Compound 1-1 gave Compound 2-69(49.2g, yield: 63%). LC-MS: M/Z781.31 (M)+)。
Example 4: synthesis of Compounds 7-8
Figure 996789DEST_PATH_IMAGE446
Figure 695755DEST_PATH_IMAGE447
(1) Synthesis of intermediate 7-1-2:
7-1-1(28.4g, 81.3mmol), pinacol diboron (24.8g, 97.5mmol), triphenylphosphine (1.6g,6mol%), bis (triphenylphosphine) palladium (II) dichloride (2.1g,3mol%), potassium phenoxide (16.1g, 121.9mmol) and anhydrous toluene (300mL) were added to a three-necked flask under nitrogen protection. After the nitrogen substitution, the reaction was stirred at 50 ℃ for 5 hours, and then the system was cooled to room temperature and quenched by adding water. The reaction mixture was extracted with benzene solvent and saturated brine. The organic phase was dried over anhydrous magnesium sulfate. The dried mixture was filtered and concentrated under reduced pressure, and purification by column chromatography or distillation gave intermediate 7-1-2(22.6g, yield: 70%). LC-MS: M/Z396.20 (M +)
(2) Synthesis of intermediate 7-1-3
After compound 7-1-2(122.9g, 310mmol) was dissolved in 1,4-dioxane (1300mL), methyl 2-bromophenylcarbamate (85.6g, 372mmol), Pd (PPh) were added thereto3)4(18g, 15.5mmol) and K2CO3(128g, 930mmol) and the resultant stirred at 100 ℃ for 6 h. After the reaction was terminated, the resultant was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was MgSO4Dried, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as developing agents to obtain the objective compound 7-1-3(84.5g, yield 65%). LC-MS: M/Z419.16(M+)。
(3) Synthesis of intermediate 7-1-4
Compound 7-1-3 (21.0 g, 50 mmol) was added to a mixture of tetrahydrofuran and LTMP (tetramethyllithium piperidine) at 0 ℃ (this mixture was obtained by dissolving 27.2 mL of LTMP in 250 mL of tetrahydrofuran). After stirring for 8 hours, distilled water was added, and extraction was performed with ethyl acetate. Dried over magnesium sulfate and distilled under reduced pressure. Column chromatography gave intermediate 7-1-4 (11.04 g, yield: 57%). LC-MS: M/Z387.14 (M)+)。
(4) Synthesis of intermediate 7-1-5
Under the protection of nitrogen, 7-1-4 (19.4 g, 50 mmol), thionyl chloride (59.5 g, 500 mmol) and DMF (50 g) are put into a three-neck flask, the temperature is slowly raised to 70 ℃, then the reaction is carried out for 3 hours, after TLC tracing reaction confirmation, the reaction product is concentrated under reduced pressure, most of thionyl chloride is distilled off, and petroleum ether is added for pulping. The resulting product was poured into 10L of ice water and filtered with suction. The finally obtained solid was slurried with 5L of water and suction-filtered to give 7-1-5 (14.0 g, yield: 69%). LC-MS: M/Z405.10 (M +).
(5) Synthesis of Compounds 7-8
Adding the intermediate 7-1-5 (40.6 g, 100mmol) and N- ([1,1' -biphenyl into a reaction vessel]-3-yl) naphthalen-2-amine (29.5g, 100mmol), tris (dibenzylideneacetone) dipalladium (3.7g, 4mol%), tri-tert-butylphosphine (1.6g, 8mol%), potassium tert-butoxide (38g, 336mmol) and o-xylene (800 mL). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to obtain a crude product, which was then subjected to column chromatography to obtain compound 7-8 (51.9 g, yield: 78%). LC-MS: M/Z664.26 (M)+)。
Example 5: synthesis of Compounds 8-70
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Figure 230828DEST_PATH_IMAGE449
Compounds 8 to 70 were synthesized by the method of reference example 4, and the other steps referred to the synthesis of compounds 7 to 8 to give compounds 8 to 70 (4.14g, yield: 56%). LC-MS: M/Z780.33 (M)+)。
Example 6: synthesis of Compounds 9-28
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Figure 255601DEST_PATH_IMAGE451
(1) Synthesis of intermediate 9-1-2
1-1-1(22.3g, 81.3mmol), pinacol diboride (24.8g, 97.5mmol), triphenylphosphine (1.6g,6mol%), bis (triphenylphosphine) palladium (II) dichloride (2.1g,3mol%), potassium phenoxide (16.1g, 121.9mmol) and anhydrous toluene (300mL) were added to a three-necked flask under nitrogen protection. After the nitrogen substitution, the reaction was stirred at 50 ℃ for 5 hours, and then the system was cooled to room temperature and quenched by adding water. The reaction mixture was extracted with benzene solvent and saturated brine. The organic phase was dried over anhydrous magnesium sulfate. The dried mixture was filtered and concentrated under reduced pressure, and purification by column chromatography or distillation gave intermediate 9-1-2(20.4g, yield: 78%). LC-MS: M/Z321.15 (M +)
(2) Synthesis of intermediate 9-1-3
After the compound 9-1-2(99.6g, 310mmol) was dissolved in 1,4-dioxane (1,4-dioxane), methyl 2- (2-bromophenyl) acetate (73.3g, 320mmol), Pd (PPh) and the like were added thereto3)4(18g, 15.5mmol) and K2CO3(128g, 930mmol) and the resulting mass was stirred at 100 ℃ for 6 h. After the reaction was terminated, the resultant was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was MgSO4Dried, and then filtered and concentrated. The concentrated residue was purified by column chromatography using ethyl acetate and hexane as developing agents to obtain the objective compound 9-1-3(76.6g,72％)。LC-MS：M/Z 344.12(M+)。
(3) synthesis of intermediate 9-1-4
Compound 9-1-3 (17.2 g, 50 mmol) was added to a mixture of tetrahydrofuran and LTMP (tetramethyllithium piperidine) at 0 ℃ (mixture obtained by dissolving 27.2 mL of LTMP in 250 mL of tetrahydrofuran). After stirring for 8 hours, distilled water was added, and extraction was performed with ethyl acetate. Dried over magnesium sulfate and distilled under reduced pressure. The compound 9-1-4 (7.2 g, yield: 46%) was obtained by column chromatography. LC-MS: M/Z311.09 (M +).
(4) Synthesis of intermediate 9-1-5
Under the protection of nitrogen, 7-1-4 (15.6 g, 50 mmol), thionyl chloride (59.5 g, 500 mmol) and DMF (50 g) are put into a three-neck flask, the temperature is slowly raised to 70 ℃ for reaction for 3 hours, after TLC tracing reaction confirmation, the reaction product is concentrated under reduced pressure, most of thionyl chloride is distilled off, and petroleum ether is added for pulping. Finally, the product was poured into 10L of ice water and filtered with suction to give a solid. The solid was slurried with 5L of water and suction-filtered to give 9-1-5 (12.1 g, yield: 73%). LC-MS: M/Z926.06 (M)+)。
(5) Synthesis of Compounds 9-28
Intermediate 9-1-5(20.2g, 61.4mmol), (4- ((9, 9-dimethyl-9H-fluoren-2-yl) (4-phenylnaphthalen-1-yl) amino) phenyl) boronic acid (32.6g, 61.4mmol), tetrakis (triphenylphosphine) palladium (4.6g, 5mol%), K2CO3(17.0g, 122.8mmol), 1,4-dioxane (500mL) and water (50 mL). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to obtain a crude product, which was then subjected to column chromatography to obtain compound 9-28 (26.4 g, yield: 55%). LC-MS: M/Z754.26 (M)+)。
Example 7: synthesis of Compounds 9-62
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Figure 668445DEST_PATH_IMAGE453
Compounds 9 to 62 were synthesized by the method of reference example 6, and the other steps referred to the synthesis of compounds 9 to 28 to give compounds 9 to 62(4.14g, yield: 56%). LC-MS: M/Z703.30 (M)+)。
Example 8: synthesis of Compounds 10-10
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Figure 351416DEST_PATH_IMAGE455
(1) Synthesis of Compound 10-1-2
1-1-1(22.3g, 81.3mmol), pinacol diboride (24.8g, 97.5mmol), triphenylphosphine (1.6g,6mol%), bis (triphenylphosphine) palladium (II) dichloride (2.1g,3mol%), potassium phenoxide (16.1g, 121.9mmol) and anhydrous toluene (300mL) were added to a three-necked flask under nitrogen protection. After the nitrogen substitution, the reaction was stirred at 50 ℃ for 5 hours, and then the system was cooled to room temperature and quenched by adding water. The reaction mixture was extracted with benzene solvent and saturated brine. The organic phase was dried over anhydrous magnesium sulfate. The dried mixture was filtered and concentrated under reduced pressure, and purification by column chromatography or distillation gave intermediate 9-1-2(20.4g, yield: 78%). LC-MS: M/Z321.15 (M)+)
(2) Synthesis of Compound 10-1-3
After the compound 9-1-2(99.6g, 310mmol) was dissolved in 1,4-dioxane (1,4-dioxane), methyl 2- (2-bromophenyl) acetate (73.3g, 320mmol), Pd (PPh) and the like were added thereto3)4(18g, 15.5mmol) and K2CO3(128g, 930mmol) and the resulting mass was stirred at 100 ℃ for 6 h. After the reaction was terminated, the resultant was cooled to room temperature and extracted with distilled water and ethyl acetate. The organic layer was MgSO4Dried, and then filtered and concentrated. Purifying the concentrated residue by column chromatography using ethyl acetate and hexane as developing agents to obtainThe objective Compound 9-1-3(68.32g, 64%). LC-MS: M/Z344.12 (M +).
(3) Synthesis of Compound 10-1-4
Compound 10-1-3 (17.2 g, 50 mmol) was added to a mixture of tetrahydrofuran and LTMP (tetramethyllithium piperidine) at 0 ℃ (this mixture was obtained by dissolving 27.2 mL of LTMP in 250 mL of tetrahydrofuran). After stirring for 8 hours, distilled water was added, and extraction was performed with ethyl acetate. Dried over magnesium sulfate and distilled under reduced pressure. Column chromatography gave 10-1-4 (8.0 g, yield: 51%) of the compound. LC-MS: M/Z312.09 (M +).
(4) Synthesis of Compound 10-1-5
Under the protection of nitrogen, 10-1-4 (15.6 g, 50 mmol), thionyl chloride (59.5 g, 500 mmol) and DMF (50 g) are put into a three-necked flask, the temperature is slowly raised, then the reaction is carried out at 70 ℃ for 3 hours, after confirming the follow-up reaction by TLC, the reaction product is decompressed and concentrated, most of the thionyl chloride is evaporated, and petroleum ether is added for pulping. The product was poured into 10L of ice water and then filtered off with suction. The solid was slurried with 5L of water and suction-filtered to give 10-1-5 (9.8 g, yield: 59%). LC-MS: M/Z330.06 (M +).
(5) Synthesis of Compounds 10-10
Mixing compound 10-1-5 (7.9 g, 23.7mmol) and 2- ([1,1' -biphenyl)]-4-yl) -4-chloro-6- (4-phenylnaphthalen-1-yl) -1,3, 5-triazine (10.2g, 21.6mmol), tetrakis (triphenylphosphine) palladium (1.2g, 1.0mmol), potassium carbonate (7.5g, 59mmol), 90mL toluene, 30mL ethanol, and 30mL distilled water were added to a reaction vessel and the reaction was stirred at 120 ℃ for 4 hours. After completion of the reaction, methanol was added dropwise to the mixture, and the resulting solid was filtered. The obtained solid was purified by recrystallization through column chromatography to obtain compound 10-10(8.3g, yield: 48%). LC-MS: M/Z729.25 (M)+)。
Example 9: synthesis of Compounds 11-35
Figure 2846DEST_PATH_IMAGE456
Figure 609408DEST_PATH_IMAGE457
Compounds 11 to 35 were synthesized by the method of reference example 8, and the synthesis of compounds 10 to 10 was referred to in all other steps to obtain compounds 11 to 35 (4.14g, yield: 56%). LC-MS: M/Z779.27 (M)+)。
Example 10: synthesis of Compounds 12-73
Figure 868351DEST_PATH_IMAGE458
Figure 75210DEST_PATH_IMAGE459
Compounds 12 to 73 were synthesized by the method of reference example 8, and the other steps referred to the synthesis of compound 10 to 10, to give compound 12 to 73 (3.41g, yield: 52%). LC-MS: M/Z691.24 (M)+)。
Device embodiments
The layers of the organic electroluminescent element of the present invention can be formed by vacuum evaporation, sputtering, ion plating, or the like, or by wet film formation such as spin coating, printing, or the like, and the solvent used is not particularly limited.
1. First embodiment
Preparation of organic electroluminescent device:
the ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. The patterned ITO glass substrate was then washed, and then placed in a vacuum chamber with a standard pressure set at 1X 10-6And (4) supporting. Thereafter evaporating HIL-1 on an ITO substrate to form a first Hole Injection Layer (HIL) having a thickness of 1150 a, evaporating HIL-2 on the first hole injection layer to form a second hole injection layer having a thickness of 50 a, evaporating HTL-1 on the second hole injection layer to form a Hole Transport Layer (HTL) having a thickness of 800 a, continuing to evaporate EB-1 on the hole transport layer to form an Electron Blocking Layer (EBL) having a thickness of 150 a, and co-evaporating the host materials of the invention (i.e., inventive compound 1-1 and compound 10-10) with guest compound (RD-1) on the electron blocking layer to form a guest compound (RD-1)An emissive layer (EML) having a thickness of 400 a (where inventive compound 1-1 and compound 10-10 were evaporated at a rate of 2: 3 (mass ratio) and the mass ratio of host material to RD-1 was 98: 2), and finally a Hole Blocking Layer (HBL) having a thickness of 30 a and an Electron Transport Layer (ETL) having a thickness of 400 a were formed sequentially with HB-1 and ET-1, respectively, and then cathodes EI-1(5 a) and Al 1000 a were evaporated, thereby preparing an organic electroluminescent device.
Figure 15485DEST_PATH_IMAGE460
Figure 929083DEST_PATH_IMAGE461
Figure 296610DEST_PATH_IMAGE462
Figure 748624DEST_PATH_IMAGE463
Figure 554906DEST_PATH_IMAGE464
Figure 136060DEST_PATH_IMAGE465
Figure 923756DEST_PATH_IMAGE466
Figure 793623DEST_PATH_IMAGE467
Figure 403596DEST_PATH_IMAGE469
2. Second embodiment
An organic electroluminescent device of the second embodiment was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with the compound 2-54 from the compound 1-1 of the first embodiment.
3. Third embodiment
An organic electroluminescent device of the third embodiment was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with compound 7-8 from compound 1-1 of the first embodiment.
4. Fourth embodiment
An organic electroluminescent device of the fourth embodiment was fabricated in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with compounds 8 to 70/11 to 35 from compounds 1 to 1/10 to 10 of the first embodiment.
5. Fifth embodiment
The organic electroluminescent device of the fifth embodiment was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with the compounds 9 to 28/11 to 35 from the compounds 1 to 1/10 to 10 of the first embodiment.
6. Sixth embodiment
An organic electroluminescent device of the sixth embodiment was fabricated in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with compounds 9 to 62/11 to 35 from compounds 1 to 1/10 to 10 of the first embodiment.
7. Seventh embodiment
An organic electroluminescent device of the seventh embodiment was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with the compounds 9 to 62/12 to 73 from the compounds 1 to 1/10 to 10 of the first embodiment.
8. Comparative example 1
The organic electroluminescent device of comparative example 1 was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with the compound Ref-1/Ref-2 from the compounds 1 to 1/10 to 10 of the first embodiment.
9. Comparative example 2
The organic electroluminescent device of comparative example 1 was prepared in the same manner as in the first embodiment described above, except that the host material layer (i.e., the light-emitting layer) of the organic electroluminescent device was replaced with the compound 2-69/Ref-2 instead of the compound 1-1/10-10 of the first embodiment.
The organic electroluminescent device was fabricated using standard methods known in the art at 10mA/cm2Voltage, efficiency and life were tested under current conditions.
Table 1 shows the performance test results of the organic electroluminescent devices prepared in the examples and comparative examples of the present invention.
TABLE 1
Figure 88524DEST_PATH_IMAGE470
As shown in table 1, the organic electroluminescent device comprising the specific compound combination according to the present invention as a host material has higher luminous efficiency and longer life characteristics than the comparative organic electroluminescent device.
10. Eighth embodiment
Preparation of organic electroluminescent device:
the ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. The patterned ITO glass substrate was then washed, and then placed in a vacuum chamber with a standard pressure set at 1X 10-6And (4) supporting. Thereafter evaporating HIL-1 on an ITO substrate to form a first Hole Injection Layer (HIL) having a thickness of 1150 a, evaporating HIL-2 on the first hole injection layer to form a second hole injection layer having a thickness of 50 a, evaporating HTL-1 on the second hole injection layer to form a Hole Transport Layer (HTL) having a thickness of 800 a, continuing to evaporate EB-1 on the hole transport layer to form an Electron Blocking Layer (EBL) having a thickness of 150 a, co-evaporating the host materials of the invention, i.e. compound 1-1 and compound 10-10 of the invention, and guest compound (RD-1) on the electron blocking layer to form an emitting layer (EML) having a thickness of 400 a (wherein compound 1-1 and compound 10-10 of the invention are evaporated at a rate of 2: 3 (mass ratio) and the mass ratio of host material to RD-1 is 98: 2), finally, respectively using 10-10 and ET-1 in sequenceAn organic electroluminescent device was prepared by forming a Hole Blocking Layer (HBL) having a thickness of 30 a and an Electron Transport Layer (ETL) having a thickness of 400 a, and then evaporating a cathode EI-1(5 a) and an Al 1000 a.
11. Ninth embodiment
An organic electroluminescent device of the ninth embodiment was fabricated by the same method as that of the above-described eighth embodiment except that the hole-blocking layer was replaced with compounds 11 to 35 from compounds 10 to 10 of the eighth embodiment.
12. Comparative example 3
The organic electroluminescent device of comparative example 3 was prepared in the same manner as in the above-described eighth embodiment, except that the hole-blocking layer was replaced with the compound Ref-2 from the compounds 10 to 10 of the eighth embodiment.
Table 2 shows the performance test results of the organic electroluminescent devices prepared in the examples and comparative examples of the present invention.
TABLE 2
Figure 266696DEST_PATH_IMAGE471
As shown in table 2, the organic electroluminescent device comprising the specific compound combination according to the present disclosure as a hole blocking layer had higher luminous efficiency and longer life characteristics than the organic electroluminescent device of the comparative substance.
The foregoing has described the general principles, principal features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (5)

1. A host material comprising at least one first host compound and at least one second host compound, wherein the first host compound is any one of:
Figure FDA0003425685100000011
Figure FDA0003425685100000021
Figure FDA0003425685100000031
Figure FDA0003425685100000041
Figure FDA0003425685100000051
Figure FDA0003425685100000061
Figure FDA0003425685100000071
Figure FDA0003425685100000081
Figure FDA0003425685100000091
Figure FDA0003425685100000101
Figure FDA0003425685100000111
Figure FDA0003425685100000121
Figure FDA0003425685100000131
Figure FDA0003425685100000141
Figure FDA0003425685100000151
Figure FDA0003425685100000161
Figure FDA0003425685100000171
Figure FDA0003425685100000181
Figure FDA0003425685100000191
Figure FDA0003425685100000201
Figure FDA0003425685100000211
Figure FDA0003425685100000221
Figure FDA0003425685100000231
Figure FDA0003425685100000241
Figure FDA0003425685100000251
Figure FDA0003425685100000261
Figure FDA0003425685100000271
Figure FDA0003425685100000281
Figure FDA0003425685100000291
Figure FDA0003425685100000301
Figure FDA0003425685100000311
Figure FDA0003425685100000321
Figure FDA0003425685100000331
Figure FDA0003425685100000341
Figure FDA0003425685100000351
Figure FDA0003425685100000361
Figure FDA0003425685100000371
Figure FDA0003425685100000381
Figure FDA0003425685100000391
Figure FDA0003425685100000401
Figure FDA0003425685100000411
wherein the second host compound is any one of:
Figure FDA0003425685100000412
Figure FDA0003425685100000421
Figure FDA0003425685100000431
Figure FDA0003425685100000441
Figure FDA0003425685100000451
Figure FDA0003425685100000461
Figure FDA0003425685100000471
Figure FDA0003425685100000481
Figure FDA0003425685100000491
Figure FDA0003425685100000501
Figure FDA0003425685100000511
Figure FDA0003425685100000521
Figure FDA0003425685100000531
Figure FDA0003425685100000541
Figure FDA0003425685100000551
Figure FDA0003425685100000561
2. an organic electroluminescent device comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the organic functional layer comprises the host material of claim 1.
3. The organic electroluminescent device according to claim 2, wherein the organic functional layer is a light-emitting layer further comprising a dopant therein.
4. The organic electroluminescent device according to claim 3, wherein the mass ratio of the host material to the dopant is 10:1 to 100: 1.
5. The organic electroluminescent device according to claim 4, wherein the mass ratio of the first host compound to the second host compound in the host material is 1:9 to 9: 1.
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