A green light-emitting host material for OLED devices

Abstract

The application provides a green light-emitting host material for an OLED device, and relates to the technical field of light-emitting materials.A green light-emitting host material for an OLED device comprises a structural compound shown in formula 1.In the application, a double-triazine-containing structure is designed to be suitable for being used as a host material of a green phosphorescent light-emitting layer of an organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer service life.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of light-emitting materials, and particularly relates to a green light-emitting host material for an OLED device. BACKGROUND

[0002] The structure of the 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 the 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 the higher requirements of people for OLED devices, more types of materials need to be developed in the field to improve the performance of OLED devices in terms of current efficiency, service life and the like. SUMMARY

[0004] Based on the technical problems existing in the background art, the present application provides a green light-emitting host material for an OLED device.

[0005] The green light-emitting host material for an OLED device provided by the present application comprises a structural compound 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 aryl.

[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, C6-C30 aryl and carbazolyl.

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

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

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

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

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

[0016]

[0017]

[0018]

[0019] An OLED device comprising the green light-emitting host material described above.

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

[0021] In the present application, the above-mentioned double-triazine-containing structure is designed to be suitable for use as a host material of a green phosphorescent light-emitting layer of an organic electroluminescent device, so that the organic electroluminescent device has a higher current efficiency and a longer service life. DETAILED DESCRIPTION

[0022] To facilitate understanding of the present application, the present application is illustrated as follows. It should be understood by those skilled in the art that the examples are only to help understand the present application, and should not be regarded as a specific limitation on the present application.

[0023] Example 1

[0024] Preparation of compound A1:

[0025]

[0026] Under nitrogen protection, 100 mL of toluene was added to a three-necked flask, 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 tetrakis triphenylphosphine palladium were added thereto, and the mixture was slowly warmed to 110℃ for 6 h, then cooled to room temperature, water and n-heptane were added and stirred to filter, the filter cake was washed with water, then stirred with ethanol for 2 times, vacuum dried, and crystallized with a mixture of toluene and chloroform to obtain 11 g of intermediate M3.

[0027] Under the condition of nitrogen protection, 140 ml of toluene, 70 ml of ethanol, and 70 ml of water were sequentially added into a three-neck flask, and then 11 g of intermediate M3, 9.02 g of compound M4 (raw material 3), 6.46 g of potassium carbonate, and 0.11 g of tetrakis triphenylphosphine palladium were added into the three-neck flask, the temperature was slowly increased to 90°C, reaction was carried out for 6 hours, the temperature was decreased to room temperature, water and n-heptane were added, filtration was carried out, the filter cake was washed with water, then stirred with ethanol twice, vacuum drying was carried out, and crystallization was carried out by using a mixed solvent of toluene and chloroform, to obtain 11.8 g of product M5, i.e., A1. Mass spectrometry was carried out on the compound A1, and the mass-to-charge ratio (m / z) was 795.27.

[0028] Example 2

[0029] Preparation of compound A2:

[0030]

[0031] Under the condition of nitrogen protection, 100 mL of toluene was added into a three-neck 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 tetrakis triphenylphosphine palladium were added into the three-neck flask, the temperature was slowly increased to 110°C, reaction was carried out for 6 hours, the temperature was decreased to room temperature, water and n-heptane were added, filtration was carried out, the filter cake was washed with water, then stirred with ethanol twice, vacuum drying was carried out, and crystallization was carried out by using a mixed solvent of toluene and chloroform, to obtain 11.37 g of intermediate M3-3.

[0032] Under the condition of nitrogen protection, 200 ml of toluene, 100 ml of ethanol, and 100 ml of water were sequentially added into a three-neck flask, 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 tetrakis triphenylphosphine palladium were added into the three-neck flask, the temperature was slowly increased to 90°C, reaction was carried out for 6 hours, the temperature was decreased to room temperature, water and n-heptane were added, filtration was carried out, the filter cake was washed with water, then stirred with ethanol twice, vacuum drying was carried out, and crystallization was carried out by using a mixed solvent of toluene and chloroform, to obtain 10.8 g of product A2. Mass spectrometry was carried out on the compound A2, and the mass-to-charge ratio (m / z) was 871.31.

[0033] Examples 3-6

[0034] Examples 3-6 are different from Example 1 only in that the raw material 1, the raw material 2, and the raw material 3 are different, and details are shown in Table 1; and mass spectrometry was carried out on the obtained compounds. The specific structural formula of the raw material 1, the raw material 2, and the raw material 3, and the mass-to-charge ratio (m / z) of the compound 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 application are as follows:

[0039]

[0040] Application Example 1

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

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

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

[0044] The materials are placed in a vacuum chamber, vacuumed to 1x10 -5 ~ 1x10 -6 Pa, and vacuum deposited on the cleaned ITO substrate in sequence to prepare an OLED device.

[0045] Among them, PGD-1[5%] refers to the doping ratio of the dye, that is, the volume ratio of the host material to the dye PGD-1 is 95:5; HT-1:HI-2[5%] refers to the ratio of P-type dopant, that is, the volume ratio of hole material HT-1 and 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] Application Examples 2-6 and Application Example 1 differ only in that the host material of the light-emitting layer is replaced by 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 Example 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 host material of the light-emitting layer is replaced by 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 lifetime of the organic electroluminescent device provided above, wherein the current efficiency is the brightness of 1000 cd / m 2The corresponding numerical value, LT95 lifetime refers to the time required for the device to reduce to 95% of the initial current density of 10 mA / cm 2 The driving voltage, current efficiency and LT95 lifetime are relative values. The specific test results are shown in Table 2.

[0051] Table 2

[0052]

[0053]

[0054] From the above, in the present application, by designing the structure of the double-triazine compound, it is suitable for the host material of the light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has lower driving voltage, higher current efficiency and longer lifetime.

[0055] The applicant declares that the present application is illustrated by the above-mentioned embodiments, but the present application is not limited to the above-mentioned detailed process. That is, it does not mean that the present application must rely on the above-mentioned detailed process to be implemented. Those skilled in the art should understand that any improvement of the present application, equivalent replacement of each raw material of the product of the present application, addition of auxiliary ingredients, selection of specific mode, etc. fall within the protection scope and disclosure scope of the present application.

Claims

1. A green light-emitting host material for an OLED device, characterized in that: The structural compound shown in formula 1: ； In the above formula 1, R0 and R9 are each independently selected from any one of C6-C30 aryl groups; 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, and C6-C30 aryl; The C6-C30 aryl group is selected from one or more of phenyl, biphenyl, terphenyl, naphthyl, and anthracenyl.

2. 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.

3. 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.

4. The green light-emitting host material according to claim 1, characterized in that The compound of formula 1 includes any one of the following compounds: ； ； ； ； ； ； ； ； ； 。 5. An OLED device, characterized in that: The green light-emitting host material comprises the green light-emitting host material according to any one of claims 1 to 4.

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