Organic electroluminescent material and preparation method thereof and organic electroluminescent device

Abstract

The invention relates to an organic electroluminescent material and a preparation method thereof and an organic electroluminescent device. According to the organic electroluminescent material, a benzo[g] bending structure is adopted as the center, a first benzene ring is introduced into the site g of the benzo[g] bending structure, then a second benzene ring is used for replacing hydrogen groups on the first benzene ring, a nitrogen heterocyclic ring is used for replacing hydrogen groups on the second benzene ring, and the following structure shown in the description is achieved, wherein Ar is a nitrogen heterocyclic ring with the electron transport function. Compared with the prior art, the organic electroluminescent material has a very proper triplet state energy level, high glass-transition temperature, good heat stability and high carrier transport capacity, the preparation method is simple, operation is easy, the yield is high, and cost is low; the organic electroluminescent material serves as a main material to replace CBP to manufacture the organic electroluminescent device, lower turn-on voltage and higher maximum current efficiency are achieved, the turn-on voltage can be reduced by 0.5-1.1 V, and the maximum current efficiency can be improved by 18% to 24%.

Description

technical field

[0001] The invention relates to the technical field of organic photoelectric materials, in particular to an organic electroluminescence material, a preparation method thereof and an application of the material in an organic electroluminescence device. Background technique

[0002] In recent years, organic light-emitting diode (OLED) is a very popular emerging technology in the 21st century. Due to its own advantages, such as self-illumination, large viewing angle, low driving voltage, high luminous brightness, ultra-thin, flexible display, etc. , making it expected to become the next-generation mainstream display to replace liquid crystal. According to the different light-emitting mechanisms of the materials used, OLED devices can be divided into fluorescent devices and phosphorescent devices. It is generally considered that the light produced by singlet excitons is fluorescence, and the light produced by triplet excitons is phosphorescence. OLED devices ar...

Examples

Embodiment 1

[0094] An organic electroluminescent material compound C01, which centers on the benzo[g]chrysene structure, introduces the first benzene ring into the g position of the benzo[g]chrysene structure, and then replaces the first benzene ring with a second benzene ring The hydrogen group on the benzene ring, and then replace the hydrogen group on the second benzene ring with a nitrogen-containing heterocycle, which has the following structure:

[0095]

[0096] A preparation method of organic electroluminescence material C01 as above, it comprises the following steps:

[0097] A, preparation of intermediate a

[0098] Under the protection of nitrogen, in a 500mL three-necked flask, dissolve o-bromoiodobenzene (42.4g, 0.15mol) and trimethylsilylacetylene (17.7g, 0.18mol) in 250mL triethylamine, and finally put tetrakistriphenylphosphine Combine palladium (5.1g, 4.5mmol) and cuprous iodide (1.71g, 9mmol), control the temperature at 20-25°C, stir for 48 hours, carry out a substit...

Embodiment 2

[0124] An organic electroluminescent material compound C05, its structure is similar to the compound C01 in Example 1, the difference is that the nitrogen-containing heterocyclic ring is different, and its structural formula is:

[0125]

[0126] A preparation method of organic electroluminescent material compound C05 as described above, its preparation method is similar to the preparation method of compound C01 in Example 1, the difference is:

[0127] In step F, prepare the organic electroluminescent material compound C05:

[0128] Under the protection of nitrogen, the intermediate e2 (1.08g, 2.5mmol) and 3-ThPyDA (1.14g, 2.625mmol) were dissolved in 20mL of toluene, then an aqueous solution of potassium carbonate (50mL, 0.2M), and finally put into 18-C -6 (0.1g, 0.3mmol) and tetrakistriphenylphosphine palladium (0.116g, 0.1mmol), control the temperature of the system to 80-85°C, stir for 48 hours, and perform a substitution reaction under the catalysis of the catalyst, t...

Embodiment 3

[0134] An organic electroluminescent material compound C08, its structure is similar to the compound C01 in Example 1, the difference is that the nitrogen-containing heterocycle is different, and its structural formula is:

[0135]

[0136] A preparation method of organic electroluminescent material compound C08 as described above, its preparation method is similar to the preparation method of compound C01 in Example 1, the difference is:

[0137] In step F, prepare the organic electroluminescent material compound C08:

[0138] Under nitrogen protection, intermediate e2 (1.08g, 2.5mmol) and 4-ThPyDA (1.14g, 2.625mmol) were dissolved in 30mL of toluene, then an aqueous solution of potassium carbonate (50mL, 0.2M) was added, and finally 18- C-6 (0.1g, 0.3mmol) and tetrakistriphenylphosphine palladium (0.116g, 0.1mmol), the temperature of the control system is raised to 80-85°C, stirred for 48 hours, and the substitution reaction is carried out under the catalysis of the catal...

technical field

[0001] The invention relates to the technical field of organic photoelectric materials, in particular to an organic electroluminescence material, a preparation method thereof and an application of the material in an organic electroluminescence device. Background technique

[0002] In recent years, organic light-emitting diode (OLED) is a very popular emerging technology in the 21st century. Due to its own advantages, such as self-illumination, large viewing angle, low driving voltage, high luminous brightness, ultra-thin, flexible display, etc. , making it expected to become the next-generation mainstream display to replace liquid crystal. According to the different light-emitting mechanisms of the materials used, OLED devices can be divided into fluorescent devices and phosphorescent devices. It is generally considered that the light produced by singlet excitons is fluorescence, and the light produced by triplet excitons is phosphorescence. OLED devices ar...

Examples

Embodiment 1

[0094] An organic electroluminescent material compound C01, which centers on the benzo[g]chrysene structure, introduces the first benzene ring into the g position of the benzo[g]chrysene structure, and then replaces the first benzene ring with a second benzene ring The hydrogen group on the benzene ring, and then replace the hydrogen group on the second benzene ring with a nitrogen-containing heterocycle, which has the following structure:

[0095]

[0096] A preparation method of organic electroluminescence material C01 as above, it comprises the following steps:

[0097] A, preparation of intermediate a

[0098] Under the protection of nitrogen, in a 500mL three-necked flask, dissolve o-bromoiodobenzene (42.4g, 0.15mol) and trimethylsilylacetylene (17.7g, 0.18mol) in 250mL triethylamine, and finally put tetrakistriphenylphosphine Combine palladium (5.1g, 4.5mmol) and cuprous iodide (1.71g, 9mmol), control the temperature at 20-25°C, stir for 48 hours, carry out a substit...

Embodiment 2

[0124] An organic electroluminescent material compound C05, its structure is similar to the compound C01 in Example 1, the difference is that the nitrogen-containing heterocyclic ring is different, and its structural formula is:

[0125]

[0126] A preparation method of organic electroluminescent material compound C05 as described above, its preparation method is similar to the preparation method of compound C01 in Example 1, the difference is:

[0127] In step F, prepare the organic electroluminescent material compound C05:

[0128] Under the protection of nitrogen, the intermediate e2 (1.08g, 2.5mmol) and 3-ThPyDA (1.14g, 2.625mmol) were dissolved in 20mL of toluene, then an aqueous solution of potassium carbonate (50mL, 0.2M), and finally put into 18-C -6 (0.1g, 0.3mmol) and tetrakistriphenylphosphine palladium (0.116g, 0.1mmol), control the temperature of the system to 80-85°C, stir for 48 hours, and perform a substitution reaction under the catalysis of the catalyst, t...

Embodiment 3

[0134] An organic electroluminescent material compound C08, its structure is similar to the compound C01 in Example 1, the difference is that the nitrogen-containing heterocycle is different, and its structural formula is:

[0135]

[0136] A preparation method of organic electroluminescent material compound C08 as described above, its preparation method is similar to the preparation method of compound C01 in Example 1, the difference is:

[0137] In step F, prepare the organic electroluminescent material compound C08:

[0138] Under nitrogen protection, intermediate e2 (1.08g, 2.5mmol) and 4-ThPyDA (1.14g, 2.625mmol) were dissolved in 30mL of toluene, then an aqueous solution of potassium carbonate (50mL, 0.2M) was added, and finally 18- C-6 (0.1g, 0.3mmol) and tetrakistriphenylphosphine palladium (0.116g, 0.1mmol), the temperature of the control system is raised to 80-85°C, stirred for 48 hours, and the substitution reaction is carried out under the catalysis of the catal...

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