Triazine compound, intermediate, organic electroluminescent device and display device

Abstract

The present invention provides a triazine compound, an intermediate, an organic electroluminescent device and a display device. The triazine compound has a structure as shown in formula (I); the intermediate has a structure as shown in formula (I-1). The triazine compound provided by the present invention can be used as an electron transport material or a hole blocking material for an OLED light-emitting device, so that the OLED light-emitting device has a lower driving voltage, a higher current efficiency and a longer high-temperature life.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to a triazine compound, an intermediate, an organic electroluminescent device and a display device. Background Art

[0002] Compared with other flat panel displays (for example, liquid crystal displays (LCDs), plasma display panels (PDPs), field emission displays (FEDs), etc.), organic electroluminescent (EL) devices have a simpler structure, various processing advantages, higher brightness, excellent viewing angle characteristics, faster response speeds, and lower driving voltages. Therefore, they are also fully developed to be used as light sources for flat panel displays (for example, wall-mounted TVs, etc.), or as backlight units for displays, illuminators, billboards, etc.

[0003] Generally, when a DC voltage is applied to an organic EL device, holes injected from the anode and electrons injected from the cathode recombine to form electron-hole pairs, i.e., excitons. When the excitons return to a stable ground state, the energy corresponding thereto is transferred to the light-emitting material, thereby converting into light.

[0004] In order to improve the performance and stability of organic EL devices, since CW Tang et al. of Eastman Kodak Company made an organic EL device operating at a low voltage by forming a series organic thin film between two opposite electrodes (CW Tang, SAVanslyke, Applied Physics Letters, vol.51, pp.913, 1987), extensive and in-depth research has been conducted on organic materials for organic EL devices with multilayer thin film structures. The performance and life of such series organic EL devices are closely related to the molecular structure of the thin film material. For example, depending on the structure of the thin film material, especially the structure of the host material, the hole transport layer material or the electron transport layer material, the quantum efficiency can vary greatly.

[0005] 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 efficiency, life, voltage, etc. Summary of the invention

[0006] In view of the shortcomings of the prior art, the present invention aims to provide a triazine compound, an intermediate, an organic electroluminescent device and a display device. In the present invention, by designing the structure of the triazine compound, and further limiting the three substituents on the triazine ring: two specific aromatic substituents of the same structure, and the third substituent on the triazine ring is a meta-substituted benzene ring structure containing dibenzofuran or dibenzothiophene substitution, the prepared triazine compound can be used as an electron transport material or a hole blocking material for an OLED light-emitting device, so that the OLED light-emitting device has a lower driving voltage, a higher current efficiency and a longer high-temperature life.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] In a first aspect, the present invention provides a triazine compound having a structure as shown in formula (I):

[0009]

[0010] wherein X is selected from O or S;

[0011] Ar 21 Any one selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C12-C20 heteroaryl;

[0012] Ar 21 The substituted substituent is selected from C1 to C5 straight or branched chain alkyl;

[0013] m and n are each independently selected from 0 or 1, and m+n=1;

[0014] The hydrogen atoms in the compound of formula (I) may be replaced by deuterium atoms.

[0015] In the present invention, by designing the structure of the triazine compound, and further limiting the three substituents on the triazine ring: two of which are specific aromatic substituents of the same structure, and the third substituent on the triazine ring is a meta-substituted benzene ring structure containing dibenzofuran or dibenzothiophene substitution, the prepared triazine compound can be used as an electron transport material or hole blocking material for an OLED light-emitting device, so that the OLED light-emitting device has a lower driving voltage, a higher current efficiency and a longer high-temperature life.

[0016] Specifically, the molecular structure contains two identical aromatic substituents, and the third substituent on the triazine ring is a meta-substituted benzene ring structure containing dibenzofuran or dibenzothiophene. This makes the intermolecular arrangement of the compound of the present invention closer and the intermolecular charge transfer smoother when preparing OLED devices, so that the prepared OLED device has higher efficiency. At the same time, the compound of the present invention has good film-forming properties, especially excellent performance at high temperatures.

[0017] In the present invention, Ar 21 Any one selected from a substituted or unsubstituted C6-C20 (for example, C6, C8, C10, C12, C16 or C20, etc.) aryl group, and a substituted or unsubstituted C12-C20 (for example, C12, C14, C16, C18 or C20, etc.) heteroaryl group.

[0018] Ar 21 The substituted substituent is selected from C1-C5 (eg, C1, C2, C3, C4 or C5) straight or branched chain alkyl.

[0019] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0020] As a preferred technical solution of the present invention, the Ar 21 Any one selected from the group consisting of phenyl, naphthyl, fluoranthenyl, triphenylene, dibenzofuranyl, dibenzothienyl, and 9,9-dimethylfluorenyl.

[0021] As a preferred technical solution of the present invention, the triazine compound is selected from any one of the following compounds:

[0022]

[0023]

[0024]

[0025] In a second aspect, the present invention provides an intermediate having a structure as shown in formula (I-1):

[0026]

[0027] wherein X is selected from O or S;

[0028] X1 is selected from any one of Cl, Br, I, hydroxyl or sulfonate;

[0029] m and n are each independently selected from 0 or 1, and m+n=1;

[0030] The intermediate is used to prepare the triazine compound as described in the first aspect.

[0031] As a preferred technical solution of the present invention, the structural formula of the sulfonate group is

[0032] Wherein, R is selected from any one of fluorinated or unsubstituted C1-C5 (for example, C1, C2, C3, C4 or C5) alkyl, fluorinated or unsubstituted C6-C10 (for example, C6, C7, C8, C9 or C10) aryl.

[0033] As a preferred technical solution of the present invention, the R is selected from any one of fluorinated or unsubstituted methyl, fluorinated or unsubstituted ethyl, fluorinated or unsubstituted propyl, fluorinated or unsubstituted butyl, fluorinated or unsubstituted phenyl, and fluorinated or unsubstituted tolyl.

[0034] As a preferred technical solution of the present invention, the intermediate is selected from any one of the following compounds:

[0035] In the present invention, when X1 is selected from Cl, Br, I, and hydroxyl, the preparation method of the intermediate (I-1) is as follows:

[0036]

[0037] wherein X is selected from O or S;

[0038] When X1 is selected from Cl, X2 is selected from Cl, Br or I; when X1 is selected from Br, X2 is selected from Br or I; when X1 is selected from I, X2 is selected from I; when X1 is selected from hydroxyl, X2 is selected from Cl, Br or I;

[0039] m and n are each independently selected from 0 or 1, and m+n=1.

[0040] When X1 is a sulfonic acid group, the preparation method of the intermediate is as follows:

[0041]

[0042] wherein X is selected from O or S;

[0043] R is selected from any one of fluorinated or unsubstituted C1-C5 alkyl, fluorinated or unsubstituted C6-C10 aryl;

[0044] X2 is selected from Cl, Br or I;

[0045] m and n are each independently selected from 0 or 1, and m+n=1.

[0046] In the present invention, the preparation method of the triazine compound having the structure of formula (I) is as follows:

[0047]

[0048] wherein X is selected from O or S;

[0049] X1 is selected from any one of Cl, Br, I or sulfonate group;

[0050] Ar 21 Any one selected from substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C12-C20 heteroaryl;

[0051] m and n are each independently selected from 0 or 1, and m+n=1.

[0052] In a third aspect, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode;

[0053] The organic thin film layer material includes the triazine compound as described in the first aspect.

[0054] As a preferred technical solution of the present invention, the organic thin film layer includes an electron transport layer, and the electron transport layer material includes the triazine compound as described in the first aspect.

[0055] Preferably, the organic thin film layer includes a hole blocking layer, and the hole blocking layer material includes the triazine compound as described in the first aspect.

[0056] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0057] Compared with the prior art, the present invention has the following beneficial effects:

[0058] The present invention designs the structure of triazine compounds and further limits three substituents on the triazine ring: two of them are specific aromatic substituents with the same structure, and the third substituent on the triazine ring is a meta-substituted benzene ring structure containing dibenzofuran or dibenzothiophene. The prepared triazine compounds can be used as electron transport materials or hole blocking materials for OLED light-emitting devices, so that the OLED light-emitting devices have lower driving voltage, higher current efficiency and longer high-temperature life. DETAILED DESCRIPTION

[0059] 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.

[0060] Synthesis Example 1

[0061] This synthesis example provides a compound 1, and the preparation method of the compound 1 is as follows:

[0062] (1) Synthesis of intermediate M-1-1

[0063]

[0064] Under nitrogen protection, 100 mL of toluene, 20 mL of ethanol and 10 mL of water were added to a 250 mL three-necked flask in sequence, and then 2.83 g (0.01 mol) of 3-bromoiodobenzene, 2.88 g (0.01 mol) of 7-phenyldibenzo [b, d] furan-3-boric acid, 2.12 g (0.02 mol) of sodium carbonate and 0.115 g (0.0001 mol) of tetrakis triphenylphosphine palladium were added. The temperature was slowly raised to 50 ° C. for reaction for 2 h, and then raised to 70 ° C. for reaction for 6 h. The temperature was lowered to room temperature, and water was added to separate. The organic layer was washed with water and dried with magnesium sulfate. After filtering to remove magnesium sulfate, the solvent was removed under reduced pressure, and separated by silica gel column chromatography, and eluted with petroleum ether: ethyl acetate = 20: 1 (volume ratio) to obtain 2.5 g of intermediate M-1-1.

[0065] The intermediate M-1-1 was subjected to mass spectrometry: the two peaks with the largest mass-to-charge ratio (m / z) were 398.03 and 400.03, and the molecular formula of the product was determined to be C 24 H 15 BrO.

[0066] (2) Synthesis of Compound 1

[0067]

[0068] Under nitrogen protection, 100 mL of toluene and 20 mL of water were added to a 250 mL three-necked flask in sequence, and then 2.77 g (0.01 mol) of the boronic acid compound shown in M-1-2, 3.99 g (0.01 mol) of the intermediate M-1-1, 2.12 g (0.02 mol) of sodium carbonate and 0.23 g (0.0002 mol) of tetrakistriphenylphosphine palladium were added, and the temperature was slowly raised to 100 ° C. to react for 12 h, and the temperature was lowered to room temperature. The solid was filtered to obtain a solid, and the solid was washed with water and methanol. After drying, it was separated by silica gel column chromatography and eluted with petroleum ether: ethyl acetate: dichloromethane = 20:1:3 (volume ratio) to obtain 4.8 g of compound 1.

[0069] Mass spectrometry was performed on compound 1: the mass-to-charge ratio (m / z) was measured to be 551.20.

[0070] The obtained compound 1 was subjected to NMR detection, and the data are as follows: 1H-NMR (Bruker, Switzerland, AvanceⅡ400MHz nuclear magnetic resonance spectrometer, CDCl3), δ8.43~8.35(m,6H), δ8.00(d,1H), δ7.91(d,1H), δ7.81~7.66(m,5H), δ7.63~7.55(m,3H), δ7.53~7.37(m,9H).

[0071] Synthesis Example 2

[0072] This synthesis example provides a compound 2, and the preparation method of the compound 2 is as follows:

[0073]

[0074] The specific preparation method refers to the preparation method of compound 1 provided in Synthesis Example 1. The only difference from Synthesis Example 1 is that the boronic acid compound represented by M-1-2 is replaced by the boronic acid compound represented by M-2-2 in an equal amount of substance, and the other conditions are the same as those in Synthesis Example 1.

[0075] The mass spectrometry of compound 2 was performed: the mass-to-charge ratio (m / z) was measured to be 651.23.

[0076] Synthesis Example 3

[0077] This synthesis example provides a compound 3, and the preparation method of the compound 3 is as follows:

[0078]

[0079] The specific preparation method refers to the preparation method of compound 1 provided in Synthesis Example 1. The only difference from Synthesis Example 1 is that the boronic acid compound represented by M-1-2 is replaced by the boronic acid compound represented by M-3-2 in an equal amount, and the other conditions are the same as those in Synthesis Example 1.

[0080] The mass spectrometry of compound 3 was performed: the mass-to-charge ratio (m / z) was measured to be 783.32.

[0081] Synthesis Example 4

[0082] This synthesis example provides a compound 4, and the preparation method of the compound 4 is as follows:

[0083] (1) Synthesis of intermediate M-4-1

[0084]

[0085] The specific preparation method refers to the preparation method of the intermediate M-1-1 provided in Synthesis Example 1, and the only difference from Synthesis Example 1 is that 7-phenyldibenzo[b,d]furan-3-boric acid is replaced by an equal amount of The other conditions were the same as those in Synthesis Example 1.

[0086] The intermediate M-4-1 was subjected to mass spectrometry: the two peaks with the largest mass-to-charge ratio (m / z) were 398.03 and 400.03, and the molecular formula of the product was determined to be C 24 H 15 BrO.

[0087] (2) Synthesis of Compound 4

[0088]

[0089] The specific preparation method refers to the preparation method of compound 1 provided in Synthesis Example 1. The only difference from Synthesis Example 1 is that intermediate M-1-1 is replaced by intermediate M-4-1 of equal amount, and other conditions are the same as those in Synthesis Example 1.

[0090] The mass spectrometry of compound 4 was performed: the mass-to-charge ratio (m / z) was measured to be 551.20.

[0091] Synthesis Example 5

[0092] This synthesis example provides a compound 5, and the preparation method of the compound 5 is as follows:

[0093]

[0094] The specific preparation method refers to the preparation method of compound 1 provided in Synthesis Example 1. The only difference from Synthesis Example 1 is that the intermediate M-1-1 is replaced by an intermediate M-4-1 of equal amount, and the boronic acid compound represented by M-1-2 is replaced by a boronic acid compound represented by M-2-2 of equal amount. Other conditions are the same as those in Synthesis Example 1.

[0095] The obtained compound 5 was subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) was measured to be 651.23.

[0096] Synthesis Example 6

[0097] This synthesis example provides a compound 6, and the preparation method of the compound 6 is as follows:

[0098]

[0099] The specific preparation method refers to the preparation method of compound 1 provided in Synthesis Example 1. The only difference from Synthesis Example 1 is that the intermediate M-1-1 is replaced by an intermediate M-4-1 of equal amount, and the boronic acid compound represented by M-1-2 is replaced by a boronic acid compound represented by M-3-2 of equal amount. Other conditions are the same as those in Synthesis Example 1.

[0100] The mass spectrometry of compound 6 revealed a mass-to-charge ratio (m / z) of 783.32.

[0101] Synthesis Example 7

[0102] This synthesis example provides a compound 7, and the preparation method of the compound 7 is as follows:

[0103] (1) Synthesis of intermediate M-7-1

[0104]

[0105] The specific preparation method refers to the preparation method of the intermediate M-1-1 provided in Synthesis Example 1, and the only difference from Synthesis Example 1 is that 7-phenyldibenzo[b,d]furan-3-boric acid is replaced by an equal amount of The other conditions were the same as those in Synthesis Example 1.

[0106] The intermediate M-7-1 was subjected to mass spectrometry: the two peaks with the largest mass-to-charge ratio (m / z) were 416.01 and 414.01, and the molecular formula of the product was determined to be C 24 H 15 BrS.

[0107] (2) Synthesis of Compound 7

[0108]

[0109] The specific preparation method refers to the preparation method of compound 1 provided in Synthesis Example 1. The only difference from Synthesis Example 1 is that intermediate M-1-1 is replaced by intermediate M-7-1 of equal amount, and other conditions are the same as those in Synthesis Example 1.

[0110] The mass spectrometry of compound 7 revealed a mass-to-charge ratio (m / z) of 567.18.

[0111] At the same time, the present invention provides a method for preparing some of the above compounds using an intermediate containing a sulfonate group.

[0112] Synthesis Example 8

[0113] This synthesis example provides a compound 1-3 prepared from intermediate M-1-1-A and intermediate M-1-1-B. The preparation method is as follows:

[0114] (1) Synthesis of intermediate M-1-1-OH

[0115]

[0116] The specific preparation method refers to the preparation method of the intermediate M-1-1 provided in Synthesis Example 1, and the only difference from Synthesis Example 1 is that o-bromoiodobenzene is replaced by an equal amount of The other conditions were the same as those in Synthesis Example 1.

[0117] The intermediate M-1-1-OH was subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) was measured to be 336.12.

[0118] (2) Synthesis of intermediate M-1-1-A

[0119]

[0120] Under nitrogen protection, add 100 mL of dichloromethane, 3.36 g (0.01 mol) of intermediate M-1-1-OH, 2 g (0.02 mol) of triethylamine and 2 drops of DMF to a 250 mL three-necked flask, cool to 0 ° C, slowly add 1.85 g (0.011 mol) of trifluoromethanesulfonyl chloride, after the addition, keep at 0-5 ° C for 1 hour, then raise the temperature to 25 ° C and keep for 2 hours, add water to separate, concentrate the organic layer to dryness, and recrystallize from isopropanol to obtain intermediate M-1-1-A.

[0121] The intermediate M-1-1-A was subjected to elemental analysis. The theoretical values ​​were: C, 64.10%; H, 3.23%; S, 6.84%; the measured values ​​were: C, 64.11%; H, 3.20%; S, 6.81%.

[0122] (2) Synthesis of intermediate M-1-1-B

[0123]

[0124] Referring to the synthesis method of M-1-1-A, the only difference is that trifluoromethanesulfonyl chloride is replaced by a dichloromethane solution of p-toluenesulfonyl chloride (the amount of p-toluenesulfonyl chloride and trifluoromethanesulfonyl chloride is the same), and other conditions are the same as the synthesis method of M-1-1-A.

[0125] The intermediate shown in M-1-1-B was subjected to elemental analysis. The theoretical values ​​were: C, 75.90%; H, 4.52%; S, 6.54%; the measured values ​​were: C, 75.92%; H, 4.51%; S, 6.50%.

[0126] Compound 1-3 was prepared by referring to the preparation methods of Synthesis Examples 1-3, with the only difference being that intermediate M-1-1 was replaced with an equal amount of intermediate M-1-1-A, and the other conditions were the same as those of Synthesis Examples 1-3.

[0127] The compound 1-3 prepared by using the intermediate M-1-1-A was subjected to mass spectrometry detection and was found to be the same as the synthesis example 1-3, indicating that the compound 1-3 was successfully prepared by the intermediate M-1-1-A.

[0128] Compound 1-3 was prepared by referring to the preparation methods of Synthesis Examples 1-3, with the only difference being that intermediate M-1-1 was replaced with an equal amount of intermediate M-1-1-B, and other conditions were the same as those of Synthesis Examples 1-3.

[0129] The compound 1-3 prepared by using the intermediate M-1-1-B was subjected to mass spectrometry detection and was found to be the same as the synthesis example 1-3, indicating that the compound 1-3 was successfully prepared by the intermediate M-1-1-B.

[0130] Synthesis Example 9

[0131] This synthesis example provides a compound 1-3 prepared from intermediate M-4-1-A and intermediate M-4-1-B. The preparation method is as follows:

[0132] (1) Synthesis of intermediate M-4-1-OH

[0133]

[0134] The specific preparation method refers to the preparation method of the intermediate M-1-1 provided in Synthesis Example 1, and the only difference from Synthesis Example 1 is that o-bromoiodobenzene is replaced by an equal amount of Will Replace with The other conditions were the same as those in Synthesis Example 1.

[0135] The obtained intermediate M-4-1-OH was subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) was measured to be 336.12.

[0136] (2) Synthesis of intermediate M-4-1-A

[0137]

[0138] Referring to the synthesis method of intermediate M-1-1-A in Synthesis Example 8, the only difference from Synthesis Example 8 is that intermediate M-1-1-OH is replaced by intermediate M-4-1-OH, and other conditions are the same as those in Synthesis Example 8.

[0139] The intermediate M-4-1-A was subjected to elemental analysis. The theoretical values ​​were: C, 64.10%; H, 3.23%; S, 6.84%; the measured values ​​were: C, 64.12%; H, 3.20%; S, 6.88%.

[0140] (2) Synthesis of intermediate M-4-1-B

[0141]

[0142] Referring to the synthesis method of intermediate M-1-1-B in Synthesis Example 8, the only difference from Synthesis Example 8 is that intermediate M-1-1-OH is replaced by intermediate M-4-1-OH, and other conditions are the same as those in Synthesis Example 8.

[0143] The intermediate M-4-1-B was subjected to elemental analysis. The theoretical values ​​were: C, 75.90%; H, 4.52%; S, 6.54%; the measured values ​​were: C, 75.91%; H, 4.53%; S, 6.51%.

[0144] Compound 4-6 was prepared by referring to the preparation method of Synthesis Example 4-6, with the only difference being that intermediate M-4-1 was replaced with an equal amount of intermediate M-4-1-A, and the other conditions were the same as those of Synthesis Example 4-6.

[0145] The compound 4-6 prepared by using the intermediate M-4-1-A was subjected to mass spectrometry detection and was found to be the same as the synthesis example 4-6, indicating that the compound 4-6 was successfully prepared by the intermediate M-4-1-A.

[0146] Compound 4-6 was prepared by referring to the preparation method of Synthesis Example 4-6, with the only difference being that the intermediate M-4-1 was replaced by an equal amount of intermediate M-4-1-B, and the other conditions were the same as those of Synthesis Example 4-6.

[0147] The compound 4-6 prepared by using the intermediate M-4-1-B was subjected to mass spectrometry detection and was found to be the same as the synthesis example 4-6, indicating that the compound 4-6 was successfully prepared by the intermediate M-4-1-B.

[0148] Other compounds whose specific synthesis steps are not listed can be prepared by common knowledge in the art in combination with the above embodiments.

[0149] The specific structures of several materials used in the device embodiments of the present invention are as follows:

[0150]

[0151]

[0152] Device Example 1

[0153] The device embodiment provides an organic electroluminescent device, the structure of which is: ITO / HIL02 (100nm) / HT (40nm) / light-emitting layer (30nm): BH:D-4 3% / electron transport material (30nm) / LiF (0.5nm) / Al (150nm).

[0154] The preparation method of the organic electroluminescent device is as follows:

[0155] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa, and then vacuum-deposited onto the cleaned ITO substrate. Among them, the light-emitting layer (30nm): BH:D-4 3% / means that in the device, BH and D-4 are co-evaporated in a volume ratio of 97:3 to form a light-emitting layer, and the thickness of the light-emitting layer is 30nm.

[0156] The electron transport material is compound 1 provided in Synthesis Example 1 of the present invention.

[0157] Device Examples 2-9

[0158] This device embodiment provides an organic electroluminescent device, which is different from device embodiment 1 only in that the electron transport layer material is different (see Table 1 below for details), and other conditions are the same as those of device embodiment 1.

[0159] Device Comparison Examples 1-4

[0160] This device comparative example provides an organic electroluminescent device, which is different from the device example 1 only in that the electron transport layer material is different (see Table 1 below for details), and other conditions are the same as those of the device example 1.

[0161] Performance Testing

[0162] Test method: The OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang was used for testing. The test items included the brightness, driving voltage, current efficiency, and LT90 high temperature life of the organic electroluminescent device; among them, the driving voltage, current efficiency, and LT90 high temperature life data were all based on a brightness of 1000cd / m 2 The relative value of LT90 high temperature life refers to the current density at the initial brightness maintained at 90-95°C (here 1000cd / m 2 ), the time required for the brightness to decrease to 90% of the initial brightness.

[0163] Table 1

[0164]

[0165] It can be seen from the contents of Table 1 that, compared with device examples 1-7, if the third substituent connected to the triazine ring has only three benzene ring structures (device comparison example 1) or the heteroaryl group in the third substituent connected to the triazine ring has more heteroatoms (device comparison example 2) or the group connected to the triazine ring does not contain heteroatoms (device comparison example 3) or the heteroaryl group in the third substituent connected to the triazine ring is directly connected to the triazine ring (device comparison example 4), the current efficiency of the prepared organic electroluminescent device is lower and the LT90 high temperature life is shorter.

[0166] Device Examples 8-9

[0167] The device embodiment provides an organic electroluminescent device, the structure of which is: ITO / HIL02 (100nm) / HT (40nm) / light-emitting layer (30nm): BH:D-4 3% / hole blocking material (5nm) / ET (30nm) / LiF (0.5nm) / Al (150nm).

[0168] The preparation method of the organic electroluminescent device is as follows:

[0169] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa, and vacuum evaporated onto the cleaned ITO substrate in sequence. Among them, the light-emitting layer (30nm): BH:D-4 3% means that in the device, BH and D-4 are co-evaporated at a volume ratio of 97:3 to form a light-emitting layer, and the thickness of the light-emitting layer is 30nm. ET is an electron transport layer.

[0170] The hole blocking material is compound 1 provided in Synthesis Example 1 of the present invention.

[0171] Device Example 9

[0172] This device embodiment provides an organic electroluminescent device, which is different from device embodiment 8 only in that the hole blocking material is compound 4 provided in synthesis embodiment 4 of the present invention, and other conditions are the same as those of device embodiment 8.

[0173] Device Comparison Examples 5-7

[0174] This device comparative example provides an organic electroluminescent device, which is different from the device example 8 only in that the hole blocking material is different (see Table 2 below for details), and other conditions are the same as those of the device example 8.

[0175] Performance Testing

[0176] Test method: The OLED-1000 multi-channel accelerated aging life and light color performance analysis system produced by Hangzhou Yuanfang was used for testing. The test items included the brightness, driving voltage, current efficiency, and LT90 high temperature life of the organic electroluminescent device; among them, the driving voltage, current efficiency data, and LT90 high temperature life data are all relative values ​​when the brightness is 1000cd / m2; LT90 high temperature life refers to the current density at the initial brightness at 90-95℃ (here 1000cd / m 2 ), the time required for the brightness to decrease to 90% of the initial brightness.

[0177] Table 2

[0178]

[0179]

[0180] It can be seen from the contents of Table 2 that, compared with device embodiments 8-9, if the heteroaryl group connected to the triazine ring has only three benzene ring structures (device comparison example 5) or the heteroaryl group in the third substituent connected to the triazine ring has more heteroatoms (device comparison example 6), the current efficiency of the prepared organic electroluminescent device is lower and the LT90 high temperature life is shorter.

[0181] In summary, the present invention designs the structure of triazine compounds, and further designs the content of the benzene ring structure in the three substituents of the triazine ring in the triazine compounds, as well as the content and position of the heteroatoms, to prepare triazine compounds that can be used as electron transport materials or hole blocking materials for OLED light-emitting devices, so that the OLED light-emitting devices have lower driving voltage, higher current efficiency and longer high-temperature life.

[0182] The applicant declares that the present invention uses the above-mentioned embodiments to illustrate the triazine compounds, electroluminescent devices and display devices of the present invention, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments 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 triazine compound, characterized in that: The triazine compound has a structure as shown in formula (I): wherein X is selected from O or S; The Ar 21 Any one selected from phenyl, naphthyl, 9,9-dimethylfluorenyl; The two Ar in the compound of formula (I) 21 same; m and n are each independently selected from 0 or 1, and m+n=1; The hydrogen atoms in the compound of formula (I) may be replaced by deuterium atoms.

2. The triazine compound according to claim 1, characterized in that The triazine compound is selected from any one of the following compounds:

3. An intermediate, characterized in that: The intermediate has a structure as shown in formula (I-1): wherein X is selected from O or S; X1 is selected from any one of Cl, Br, I, hydroxyl or sulfonate; m and n are each independently selected from 0 or 1, and m+n=1; The intermediate is used for preparing the triazine compound as claimed in claim 1 or 2.

4. The intermediate according to claim 3, characterized in that The structural formula of the sulfonate group is Wherein, R is selected from any one of a fluorinated or unsubstituted C1-C5 alkyl group and a fluorinated or unsubstituted C6-C10 aryl group.

5. The intermediate according to claim 4, characterized in that The R is selected from any one of fluorinated or unsubstituted methyl, fluorinated or unsubstituted ethyl, fluorinated or unsubstituted propyl, fluorinated or unsubstituted butyl, fluorinated or unsubstituted phenyl, and fluorinated or unsubstituted tolyl.

6. The intermediate according to any one of claims 3 to 5, characterized in that The intermediate 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 thin film layer arranged between the anode and the cathode; The organic thin film layer material comprises the triazine compound as claimed in claim 1 or 2.

8. The organic electroluminescent device according to claim 7, characterized in that: The organic thin film layer comprises an electron transport layer, and the electron transport layer material comprises the triazine compound as claimed in claim 1 or 2.

9. The organic electroluminescent device according to claim 7, characterized in that: The organic thin film layer comprises a hole blocking layer, and the hole blocking layer material comprises the triazine compound as claimed in claim 1 or 2.

10. A display device, characterized in that: The display device comprises the organic electroluminescent device according to any one of claims 7 to 9.

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