Green light-emitting main body material for OLED (Organic Light Emitting Diode) device

Abstract

The invention provides a green light-emitting main body material for an OLED device, and relates to the technical field of light-emitting materials. The invention relates to a green light-emitting main body material for an OLED device. The green light-emitting main body material comprises a structural compound as shown in formula 1. According to the present invention, by designing the bis-triazine-containing connection structure, the bis-triazine-containing connection structure can be used as the main body material of the organic electroluminescent device green phosphorescence light-emitting layer so as to provide the high current efficiency and the long service life of the organic electroluminescent device.

Description

Technical Field

[0001] The present invention relates to the technical field of luminescent materials, and in particular to a green luminescent host material for an OLED device. Background Art

[0002] The structure of an organic electroluminescent device is specifically: an anode, a cathode, and an organic layer between the two. In order to improve the efficiency and stability of an organic electroluminescent element, the organic material layer includes multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer, a light-emitting layer, an electron transport layer (ETL), and an electron injection layer (EIL). Currently, organic electroluminescence has become a mainstream display technology, and accordingly, various new OLED materials have also been developed.

[0003] In order to meet people's higher requirements for OLED devices, the field is in urgent need of developing more types of materials to improve the performance of OLED devices in terms of current efficiency, life span, etc. Summary of the invention

[0004] Based on the technical problems existing in the background technology, the present invention proposes a green light-emitting host material for OLED devices.

[0005] The present invention provides a green light-emitting host material for an OLED device, comprising a compound having a structure shown in Formula 1:

[0006]

[0007] In the above formula 1, R0 and R9 are each independently selected from any one of H, C6-C30 aryl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl.

[0008] R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from any one of H, D, and C6-C30 aromatic groups.

[0009] It should be noted that "D" represents an isotope D atom of hydrogen, and the same applies hereinafter.

[0010] B1, B2, B3, B4, B5, B6, and B7 are each independently selected from any one of H, D, a C6-C30 aryl group, and a carbazole group.

[0011] Preferably, R0 and R9 are C6-C30 aromatic groups.

[0012] Preferably, the C6-C30 aryl group is selected from one or more of phenyl, biphenyl, terphenyl, naphthyl and anthracenyl.

[0013] Preferably, any one of R1, R2, R3, R4, R5, R6, R7, and R8 is phenyl or biphenyl, and the others are H or D.

[0014] Preferably, any one of B1, B2, B3, B4, B5, B6, and B7 is phenyl or biphenyl, and the rest are H or D.

[0015] Preferably, the compound of formula 1 above includes any one of the following compounds:

[0016]

[0017]

[0018]

[0019] An OLED device comprises the green light-emitting main material.

[0020] Compared with the prior art, the present invention has the following beneficial effects:

[0021] In the present invention, the bitriazine-containing connected structure is designed to be suitable for being used as the main material of the green phosphorescent light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer life. DETAILED DESCRIPTION

[0022] For the convenience of understanding the present invention, the present invention lists the following embodiments. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0023] Example 1

[0024] Preparation of compound A1:

[0025]

[0026] Under nitrogen protection, 100 mL of toluene was added to a three-necked flask, and then 10 g of compound M1 (raw material 1), 5.7 g of compound M2 (raw material 2), 8.5 g of potassium carbonate, and 1 g of tetrakistriphenylphosphine palladium were added thereto, and the temperature was slowly raised to 110°C for reaction for 6 h, and then the temperature was lowered to room temperature, and water and n-heptane were added, stirred, and filtered. After the filter cake was washed with water, it was stirred twice with ethanol, vacuum dried, and crystallized with a mixed solvent of toluene and chloroform to obtain 11 g of intermediate M3;

[0027] Under nitrogen protection, 140 ml toluene, 70 ml ethanol, and 70 ml water were added to a three-necked flask in sequence, and then 11 g intermediate M3, 9.02 g compound M4 (raw material 3), 6.46 g potassium carbonate, and 0.11 g tetrakistriphenylphosphine palladium were added thereto, and the temperature was slowly raised to 90°C for reaction for 6 hours, and then the temperature was lowered to room temperature, and water and n-heptane were added, and the mixture was filtered. After washing the filter cake with water, the mixture was stirred twice with ethanol, dried in vacuo, and crystallized with a mixed solvent of toluene and chloroform to obtain 11.8 g product M5, i.e. A1. Compound A1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 795.27.

[0028] Example 2

[0029] Preparation of compound A2:

[0030]

[0031] Under nitrogen protection, 100 mL of toluene was added to a three-necked flask, and then 10 g of compound M1 (raw material 1), 7.45 g of compound M2-2 (raw material 2), 8.14 g of potassium carbonate, and 1 g of tetrakistriphenylphosphine palladium were added thereto, and the temperature was slowly raised to 110°C for reaction for 6 h, and then the temperature was lowered to room temperature, and water and n-heptane were added, stirred, and filtered. After the filter cake was washed with water, it was stirred twice with ethanol, vacuum dried, and crystallized with a mixed solvent of toluene and chloroform to obtain 11.37 g of intermediate M3-3;

[0032] Under nitrogen protection, 200 ml toluene, 100 ml ethanol, and 100 ml water were added to a three-necked flask in sequence, and then 11.37 g of intermediate M3-3, 9.2 g of compound M4-4 (raw material 3), 6.1 g of potassium carbonate, and 0.114 g of tetrakistriphenylphosphine palladium were added thereto, and the temperature was slowly raised to 90°C for reaction for 6 hours, and then the temperature was lowered to room temperature, and water and n-heptane were added for stirring and filtration. After the filter cake was washed with water, it was stirred with ethanol twice, vacuum dried, and crystallized with a mixed solvent of toluene and chloroform to obtain 10.8 g of product A2. Compound A2 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 871.31.

[0033] Embodiment 3-6

[0034] The difference between Example 3-6 and Example 1 is that the raw material 1, raw material 2, and raw material 3 are different, as shown in Table 1; and the obtained compounds are respectively subjected to mass spectrometry detection. The specific structural formulas of raw materials 1, raw materials 2 and raw materials 3, the compounds, and the mass-to-charge ratios (m / z) of the compounds are shown in Table 1.

[0035] Table 1

[0036]

[0037]

[0038] The specific structures of some compounds used in the following application examples and comparative application examples of the present invention are as follows:

[0039]

[0040] Application Example 1

[0041] This application example provides an application example of a green light organic electroluminescent device, using the compound A1 provided by the present invention as a main material of the light-emitting layer, and the structure of the green light organic electroluminescent device is:

[0042] ITO / HT-1: HI-2[5%](80nm) / HT-1(30nm) / EB-3(20nm) / host material: PGD-1[5%](35nm) / ETL-1(25nm) / LiF(0.5nm) / Al(150nm).

[0043] The preparation method of the green organic electroluminescent device is as follows:

[0044] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa was vacuum evaporated onto the cleaned ITO substrate in turn to prepare an OLED device.

[0045] PGD-1[5%] refers to the doping ratio of the dye, that is, the volume ratio of the main material to the dye PGD-1 is 95:5; HT-1:HI-2[5%] refers to the ratio of the P-type dopant, that is, the volume ratio of the hole material HT-1 and the P-type dopant HI-2 is 95:5. HT-1 is a hole transport material; HT-1:HI-2[5%] is used as a hole injection layer, and EB-3 is an electron blocking layer.

[0046] Application Example 2-6

[0047] The only difference between Application Example 2-6 and Application Example 1 is that the main material of the light-emitting layer is replaced with other compounds (see Table 2 for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0048] Comparative Application Examples 1-3

[0049] Comparative Application Examples 1-3 each provide a green light organic electroluminescent device, which differs from Application Example 1 only in that the main material of the light-emitting layer is replaced with other compounds (see Table 2 for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0050] Performance test: Test the brightness, driving voltage, current efficiency and LT95 life of the organic electroluminescent device provided above, where the current efficiency is the brightness of 1000cd / m 2The corresponding value, LT95 life refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density when the device remains unchanged. Among them, the driving voltage, current efficiency and LT95 life are relative values. The specific test results are shown in Table 2.

[0051] Table 2

[0052]

[0053]

[0054] From the above content, it can be seen that the structure of the bistriazine compound is designed in the present invention to make it suitable as the main material of the light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has a lower driving voltage, higher current efficiency and longer life.

[0055] The applicant declares that the present invention illustrates the detailed process flow of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed process flow, that is, it does not mean that the present invention must rely on the above-mentioned detailed process flow to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A green light-emitting host material for an OLED device, characterized in that: Including the structural compound shown in formula 1: In the above formula 1, R0 and R9 are each independently selected from any one of H, C6-C30 aryl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from any one of H, D, and C6-C30 aryl; B1, B2, B3, B4, B5, B6, and B7 are each independently selected from any one of H, D, a C6-C30 aryl group, and a carbazole group.

2. The green light-emitting host material according to claim 1, characterized in that: The R0 and R9 are C6-C30 aromatic groups.

3. The green light-emitting host material according to any one of claims 1 or 2, characterized in that: The C6-C30 aryl group is selected from one or more of phenyl, biphenyl, terphenyl, naphthyl and anthracenyl.

4. The green light-emitting host material according to claim 1, characterized in that: The R1, R2, R3, R4, R5, R6, R7 and R8 are each independently selected from one of H, D, phenyl and biphenyl.

5. The green light-emitting host material according to claim 1, characterized in that: The B1, B2, B3, B4, B5, B6 and B7 are each independently selected from one of H, D, phenyl and biphenyl.

6. The green light-emitting host material according to any one of claims 1 to 5, characterized in that: The compound of formula 1 includes any one of the following compounds:

7. An OLED device, characterized in that: The green light-emitting host material comprises the green light-emitting host material as described in any one of claims 1 to 6.

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