Triazine compound, composition and organic electroluminescent device

Abstract

The invention provides a triazine compound, a composition and an organic electroluminescent device. The triazine compound has a structure as shown in a formula I. According to the invention, the structure of the triazine compound is designed, the triazine compound is used as the main body material of the light-emitting layer of the OLED device, and the prepared OLED device has relatively low driving voltage, relatively high current efficiency, relatively long service life and relatively long high-temperature service life.

Description

Technical Field

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

[0002] Displays, integrating electronics, communications, and information processing technologies, are considered a major development opportunity for the electronics industry after electronics and computers. Display technology and displays have played a crucial role in the development of information technology. Displays on televisions, computers, phones, and various instruments provide a wealth of information for our daily lives and work. In recent years, new display technologies have become a focus of research, with flat-panel displays, particularly due to their light weight, low power consumption, and portability.

[0003] Liquid crystal displays (LCDs) hold a prominent position among the many types of flat-panel displays currently available. However, LCDs have numerous drawbacks: they lack their own light and rely on a light source or ambient light, suffer from viewing angle issues, have slow response times, and exhibit low resolution. Consequently, the search for new flat-panel display technologies has been ongoing. Organic electroluminescence (OLED) was discovered as early as 1963, but initially received little attention. It wasn't until 1987, when the Tang Research Group at Eastman Kodak published a high-brightness, high-efficiency, thin-film organic electroluminescent device (OLED) driven by a low DC voltage using organic fluorescent materials and hole-forming materials, that the technology regained attention and ushered in a whole new research field.

[0004] OLEDs offer significant advantages, including low power consumption, fast response time, flexibility, wide viewing angles, large display areas, and a full range of luminous colors. They are also compatible with a variety of existing standards and technologies, enabling low-cost light-emitting devices. They hold broad application prospects in achieving color flat-panel displays. Over the past few decades, OLEDs, as a new display technology, have achieved significant development, finding widespread application in flat-panel displays, flexible displays, solid-state lighting, and automotive displays.

[0005] The choice of materials for the hole layer, light-emitting layer, and other organic functional layers in OLED display devices will have a significant impact on the current efficiency, driving voltage, and life of the device. At the same time, the application environment temperature of some OLED devices is currently relatively high, so a longer high-temperature life is also required for OLED devices. Summary of the Invention

[0006] To address the shortcomings of the prior art, the present invention provides a triazine compound, composition, and organic electroluminescent device. By designing the structure of the triazine compound, the present invention uses the triazine compound as the main material for the light-emitting layer of an OLED device. The resulting OLED device exhibits low driving voltage, high current efficiency, and a long lifespan, including a long high-temperature lifespan.

[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 shown in the following formula I:

[0009]

[0010] Wherein, R1 is selected from any one of phenyl, naphthyl, and biphenyl;

[0011] R2, R3, R4, and R5 are each independently selected from any one of a hydrogen atom (H), a phenyl group, a naphthyl group, and a biphenyl group;

[0012] At least five hydrogen atoms in the compound of formula I are not replaced by deuterium atoms, and the remaining hydrogen atoms can each independently be replaced by a deuterium atom.

[0013] In the present invention, the structure of the triazine compound is designed so that the triazine compound is used as the main material of the light-emitting layer of the OLED device. The prepared OLED device has a lower driving voltage, higher current efficiency and longer life.

[0014] It should be noted that, in the present invention, "D" represents a deuterium atom. Unless otherwise specified in the present invention, H and hydrogen therein represent a combination of protium, deuterium and tritium in natural abundance, and the same shall apply hereinafter.

[0015] 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.

[0016] As a preferred technical solution of the present invention, the compound of formula I has any one of the structures shown in formula I-1, formula I-2 or formula I-3:

[0017]

[0018] Wherein, R1 is selected from any one of phenyl, naphthyl, and biphenyl;

[0019] R2, R3, R4, and R5 are each independently selected from any one of a hydrogen atom (H), a phenyl group, a naphthyl group, and a biphenyl group;

[0020] At least five hydrogen atoms in the compound of formula I-1, the compound of formula I-2, and the compound of formula I-3 are not replaced by deuterium atoms, and the remaining hydrogen atoms can each independently be replaced by a deuterium atom.

[0021] As a preferred technical solution of the present invention, the R1 is selected from phenyl.

[0022] As a preferred technical solution of the present invention, the triazine compound is selected from any one of the following substituted or unsubstituted compounds:

[0023]

[0024]

[0025] The substitution means that at least five hydrogen atoms in the triazine compound are not replaced by deuterium atoms, and the remaining hydrogen atoms can be independently replaced by deuterium atoms.

[0026] Preferably, the triazine compound includes the following compounds:

[0027]

[0028] It should be noted that the preparation method of the triazine compound provided by the present invention is not subject to any special limitation, and any preparation method commonly used in the art is applicable.

[0029] In a second aspect, the present invention also provides another triazine compound, which includes compound D3 and compound D4:

[0030]

[0031] In a third aspect, the present invention provides a composition comprising at least a first component and a second component, wherein the first component comprises at least one triazine compound as described in the first aspect or the triazine compound as described in the second aspect, and the second component comprises at least one compound having a structure represented by the following formula II:

[0032]

[0033] wherein R6, R7, R8, and R9 are each independently selected from a C6-C20 aryl group or a C6-C20 heteroaryl group;

[0034] m, o, and p are each independently selected from an integer between 0 and 4;

[0035] n is selected from an integer between 0 and 3;

[0036] The hydrogen atoms in the compound of formula II can be replaced independently by deuterium atoms (-D), -F, -CN, C1-C12 alkyl, C1-C12 alkoxy, triphenylsilyl ( The dotted line indicates the connection site, the same below), triphenylmethyl The compound is substituted with at least one of a C6-C20 aryl group or a C6-C20 heteroaryl group.

[0037] In the compound of formula II, C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12.

[0038] C6-C20 can be C6, C10, C12, C15, C18 or C20, etc.

[0039] Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, butyl, pentyl, methylcyclopentyl, hexyl, methylcyclohexyl, heptyl, octyl, adamantyl, bicyclo[2.2.1]heptyl or bicyclo[2.2.2]octyl.

[0040] Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy.

[0041] Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl and 9,9-dimethylfluorenyl.

[0042] Preferably, the C6-C20 heteroaryl group is selected from any one of a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group.

[0043] As a preferred technical solution of the present invention, m+n+o+p=0.

[0044] As a preferred technical solution of the present invention, m+n=0, o+p=1.

[0045] As a preferred technical solution of the present invention, m+n=0, o=0, and p=1.

[0046] As a preferred technical solution of the present invention, m+n=0, o=1, and p=0.

[0047] As a preferred technical solution of the present invention, m+n=0, o=0, and p=2.

[0048] As a preferred technical solution of the present invention, m+n=0, o=2, and p=0.

[0049] As a preferred technical solution of the present invention, m+n=0, o=1, and p=1.

[0050] As a preferred technical solution of the present invention, m=1, n=1, o=0, and p=1.

[0051] As a preferred technical solution of the present invention, m=1, n=o=0, and p=1.

[0052] As a preferred technical solution of the present invention, R6, R7, R8, and R9 are each independently selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl.

[0053] Preferably, R6, R7, and R8 are each independently selected from any one of phenyl, naphthyl, or biphenyl, and more preferably phenyl.

[0054] Preferably, R9 is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl.

[0055] As a preferred technical solution of the present invention, the hydrogen atoms in the compound of formula II can each independently be replaced by at least one of a deuterium atom (-D), -F, -CN, a methyl group, an ethyl group, a propyl group, a tert-butyl group, a methoxy group, an ethoxy group, a propoxy group, a phenyl group, a naphthyl group, a biphenyl group, a carbazolyl group or a triphenylsilyl group.

[0056] As a preferred technical solution of the present invention, the compound of formula II is selected from any one of the following substituted or unsubstituted compounds:

[0057]

[0058]

[0059] The substitution means that the hydrogen atoms in the above carbazole compounds can be independently replaced by deuterium atoms. Preferably, the compound of formula II is selected from any one of the following compounds:

[0060]

[0061]

[0062] It should be noted that the present invention does not have any special limitations on the preparation method of the compound of formula II, and any commonly used preparation method in the art is applicable.

[0063] In a fourth aspect, the present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;

[0064] The material of the organic thin film layer includes at least one of the triazine compound described in the first aspect, the triazine compound described in the second aspect, or the composition described in the third aspect.

[0065] Preferably, the organic thin film layer includes a light-emitting layer;

[0066] The host material of the light-emitting layer includes at least one of the triazine compound described in the first aspect, the triazine compound described in the second aspect, or the composition described in the third aspect.

[0067] As a preferred technical solution of the present invention, the organic electroluminescent device is a green organic electroluminescent device.

[0068] The luminescent layer of the present invention includes a luminescent layer host material and a dopant material, wherein the dopant material is also called a dye or a phosphorescent luminescent material. The luminescent layer host material can be a single compound or a mixture of two or more compounds.

[0069] Preferably, the light-emitting layer includes a phosphorescent light-emitting layer, and the phosphorescent light-emitting layer includes a green phosphorescent light-emitting layer, a red phosphorescent light-emitting layer, and a blue phosphorescent light-emitting layer.

[0070] The volume percentage of the main material in the phosphorescent light-emitting layer is 60% to 99.9% (for example, it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98% or 99.9%, etc.), preferably 70% to 99.5%, and more preferably 85% to 95%.

[0071] In the present invention, the doping material for the light-emitting layer may be a phosphorescent material, which is also called a triplet light-emitting material and refers to a substance that emits light from a triplet excited state. The specific choice of phosphorescent material in the present invention is not particularly limited, and any doping material for the light-emitting layer commonly used in the art is applicable, including but not limited to compounds having a structure as shown in Formula PD:

[0072]

[0073] wherein M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu, or Au;

[0074] Y1-Y4 are each independently selected from carbon or nitrogen;

[0075] Y1 and Y2 can be connected by a single bond or a double bond, and Y3 and Y4 can be connected by a single bond or a double bond;

[0076] Cy1 and Cy2 are each independently selected from any one of phenyl, naphthyl, fluorenyl, spirofluorenyl, indenyl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiophenyl, benzimidazolyl, benzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, N-heterocarbazolyl, N-heterodibenzofuranyl, wherein Cy1 and Cy2 may be optionally linked to each other via a single bond or an organic linking group;

[0077] Any two ligands of M, or more than two ligands, may be connected by a single bond or a double bond, or may be bridged by O or S, or may be connected by any chemical group or chemical structure to form a structural form that conforms to chemical principles;

[0078] R 91 and R 92Each is independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid, carboxylate, sulfonic acid, sulfonate, phosphoric acid, phosphate, -SF5, substituted or unsubstituted C1-C60 (for example, C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkyl, substituted or unsubstituted C2-C6 C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkenyl, substituted or unsubstituted C2-C60 (for example, C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkynyl, substituted or unsubstituted C1-C60 (for example, C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) C2-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9 or C10) heterocycloalkyl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryl, substituted or unsubstituted C6-C60 ( For example, it can be any one of C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryloxy, substituted or unsubstituted C6-C60 (for example, it can be C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) arylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0079] a1 and a2 are each independently an integer selected from 1 to 5, for example, 1, 2, 3, 4 or 5;

[0080] b is an integer selected from 0-4, for example, 0, 1, 2, 3 or 4;

[0081] a is selected from 1, 2 or 3;

[0082] L1 is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

[0083] Preferably, the compound of formula PD is selected from any one of the following compounds:

[0084]

[0085]

[0086]

[0087]

[0088] In a fifth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the fourth aspect.

[0089] Compared with the prior art, the present invention has the following beneficial effects:

[0090] In the present invention, the structure of the triazine compound is designed, and the triazine compound is used as the main material of the light-emitting layer of the OLED device. The prepared OLED device has a lower driving voltage, higher current efficiency, longer life and longer high-temperature life. DETAILED DESCRIPTION

[0091] For the convenience of understanding the present invention, the present invention is given below with examples. It should be understood by those skilled in the art that the examples are only for the purpose of helping to understand the present invention and should not be regarded as specific limitations of the present invention.

[0092] Preparation Example 1

[0093] This preparation example provides intermediate M1 and its synthesis method, the synthesis method is as follows:

[0094]

[0095] Under nitrogen protection, 3-iodo-tert-butylbenzene (2.6 g), 4-bromocarbazole (2.5 g), anhydrous potassium carbonate (2.5 g), o-dichlorobenzene (30 mL), DMF (6 mL), cuprous oxide (0.1 g), o-phenanthroline (0.2 g) were added to a three-necked flask, first reacted at 80 ° C for 4 hours, then heated to 120 ° C for 6 hours, cooled, filtered to remove insoluble matter, washed with water, separated, the organic layer was washed with water until neutral, dried over anhydrous magnesium sulfate, filtered to remove the desiccant, concentrated to dryness, and crystallized with ethanol to obtain intermediate M1 (2.1 grams).

[0096] The mass spectrometry of the intermediate M1 showed that its mass-to-charge ratio (m / z) was 377.08.

[0097] Preparation Example 2-3

[0098] Preparation Examples 2-3 respectively provide an intermediate and a synthesis method thereof. The synthesis method of the corresponding intermediate refers to the preparation method of intermediate M1. Raw materials 1 and 2 are reacted to prepare the corresponding intermediate, and the mass spectrum of the prepared intermediate is measured to record its mass-to-charge ratio m / z. Details are shown in Table 1 below:

[0099] Table 1

[0100]

[0101]

[0102] Synthesis Example 1 Synthesis of Compound P1

[0103] This synthesis example provides compound P1 and its synthesis method, the synthesis method is as follows:

[0104]

[0105] Under a nitrogen atmosphere, dry toluene (50 mL), intermediate M1 (3.8 g), carbazole (1.7 g), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 g), 0.8 g of a 10% mass percentage tri-tert-butylphosphine toluene solution (the mass of tri-tert-butylphosphine is 0.08 g) and sodium tert-butoxide (1.2 g) were added to a three-necked flask, heated to reflux temperature, reacted for 8 h, cooled to room temperature, and separated by adding water. The organic layer was then washed with water until neutral, dried with magnesium sulfate, filtered to remove the magnesium sulfate, concentrated to dryness, and crystallized from a mixed solvent of toluene and ethanol to obtain compound P1 (3.8 g).

[0106] Compound P1 was subjected to mass spectrometry detection: its mass-to-charge ratio (m / z) was measured to be 464.23.

[0107] Synthesis Examples 2-5

[0108] Synthesis Examples 2-5 provide a compound and a synthesis method thereof, respectively. The synthesis method of the compound refers to the preparation method of compound P1, and the corresponding raw materials 3 and 4 are reacted to prepare the corresponding compounds. The mass spectra of the prepared compounds are measured and their mass-to-charge ratios m / z are recorded. Details are shown in Table 2 below:

[0109] Table 2

[0110]

[0111] Synthesis Example 6 Synthesis of Compound A1

[0112] This synthesis example provides compound A1 and its synthesis method, the synthesis method is as follows:

[0113]

[0114] Under nitrogen, 70 mL of toluene, 40 mL of ethanol, and 20 mL of water were added to a three-necked flask, followed by 4.5 g of intermediate A1-1, 3.0 g of intermediate A1-2, 2.12 g of sodium carbonate, and 0.23 g of tetrakistriphenylphosphine palladium. The temperature was slowly raised to 60°C for reaction for 6 h, then raised to reflux for reaction for 2 h, cooled to room temperature, and separated by adding water. The organic layer was washed with water, dried over magnesium sulfate, and after removing the desiccant, concentrated to dryness, and crystallized from a mixed solvent of toluene and chloroform to obtain compound A1 (3.9 g).

[0115] The obtained compound A1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 644.25.

[0116] Synthesis Examples 7-8

[0117] Synthesis Examples 7-8 provide a compound and a synthesis method thereof, respectively. The synthesis method of the compound refers to the preparation method of compound P1, and the corresponding raw materials 5 and 6 are reacted to prepare the corresponding compounds. The mass spectra of the prepared compounds are measured and their mass-to-charge ratios m / z are recorded. Details are shown in Table 3 below:

[0118] Table 3

[0119]

[0120]

[0121] The synthesis of other compounds not listed can be carried out by referring to the above examples in combination with common knowledge in the art.

[0122] The specific structures of the compounds used in the following device examples and device comparative examples are as follows:

[0123]

[0124]

[0125] The synthesis of compound D1 is as follows:

[0126]

[0127] Referring to the synthesis of compound A1, compound D1 was prepared by changing the corresponding raw materials.

[0128] The obtained compound D1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 648.28.

[0129] The synthesis of compound D3 is as follows:

[0130]

[0131] Referring to the synthesis of compound A1, compound D3 was prepared by changing the corresponding raw materials.

[0132] The obtained compound D3 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 644.25.

[0133] The synthesis of compound D4 is as follows:

[0134]

[0135] Referring to the synthesis of compound A1, compound D4 was prepared by changing the corresponding raw materials.

[0136] The obtained compound D4 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 644.25.

[0137] Device Example 1

[0138] This device embodiment provides an organic electroluminescent device, and the compound provided by the present invention is selected as the green light host material in the organic electroluminescent device.

[0139] The structure of the organic electroluminescent device is: ITO / HT-1 (40 nm) / green light host material (35 nm): PGD-1 [10%] / ETL-1 (25 nm) / LiF (0.5 nm) / Al (150 nm).

[0140] The preparation process of organic electroluminescent devices is as follows:

[0141] The preparation method of the green organic electroluminescent device is as follows:

[0142] 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 to prepare OLED devices.

[0143] PGD-1[10%] refers to the doping ratio of the dye, that is, the volume ratio of the host material to the dye PGD-1 is 90:10; HT-1 is a hole transport material, and ETL-1 is an electron transport material.

[0144] The green light host material of the green organic electroluminescent device provided in this application example is compound A1.

[0145] Device Examples 2-3, Device Comparative Examples 1-3

[0146] Device Examples 2-3 and Comparative Device Examples 1-3 respectively provide an organic electroluminescent device, which differs from Device Example 1 only in that the green light host material is different (see Table 4 below for details). Other preparation steps and conditions are the same as those of Device Example 1.

[0147] Performance testing:

[0148] The test measures the brightness, driving voltage, current efficiency, life test LT90 and LT90 high temperature of the prepared organic electroluminescent device. Among them, the life test LT90 refers to the current density at room temperature (25-27°C) at the initial brightness (here 1000cd / m 2 The time required for the brightness to decrease to 90% of the initial brightness is LT90 high temperature, which means the current density at the initial brightness is kept constant at 90-95℃ (here 1000cd / m 2 ), and the time it takes for the brightness to decrease to 90% of the initial brightness. The driving voltage, current efficiency, LT90, and LT90 high temperature values are all relative values. The test results are detailed in Table 4 below.

[0149] Table 4

[0150]

[0151] In compound A1, the electron-withdrawing group (triazine ring) and the electron-donating group (carbazolyl) are attached to the same benzene ring. Deuteration of this benzene ring hinders energy transfer between the triazine and carbazole rings in the excited state, allowing for better energy transfer to the dye, improving the device's voltage and efficiency. Furthermore, deuteration of the benzene ring alters the charge distribution within the material molecule, enhancing its stability. Performance is particularly strong at high temperatures, improving the device's LT90 high-temperature performance and expanding the material's application temperature range.

[0152] Comparison of device examples 1-3 and device comparative examples 2-3 shows that even if the benzene ring between the triazine ring and the carbazole ring in the green light host material molecule is deuterated, if the entire material molecule contains too few H atoms, it will have an adverse effect on the device performance.

[0153] As can be seen from the contents of Table 4, in the present invention, by designing the structure of the triazine compound, the triazine compound is used as the main material of the light-emitting layer of the OLED device, and the OLED device prepared has a lower driving voltage, higher current efficiency, longer life and longer high-temperature life.

[0154] Device Example 4, Device Comparative Examples 4-5

[0155] Device Example 4 and Device Comparative Examples 4-5 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the green light host material is different (see Table 5 below for details). Other preparation steps and conditions are the same as those of Device Example 1.

[0156] Performance testing:

[0157] The test measures the brightness, driving voltage, current efficiency, life test LT90 and LT90 high temperature of the prepared organic electroluminescent device. Among them, the life test LT90 refers to the current density at room temperature (25-27°C) at the initial brightness (here 1000cd / m 2 The time required for the brightness to decrease to 90% of the initial brightness is LT90 high temperature, which means the current density at the initial brightness is kept constant at 90-95℃ (here 1000cd / m 2 ), and the time it takes for the brightness to decrease to 90% of the initial brightness. The driving voltage, current efficiency, LT90, and LT90 high temperature values are all relative values. The test results are detailed in Table 5 below.

[0158] Table 5

[0159]

[0160] Device Examples 5-8

[0161] Device Examples 5-8 each provide an organic electroluminescent device, which differs from Device Example 1 only in that the green light host material is different (see Table 6 below for details). Other preparation steps and conditions are the same as those of Device Example 1.

[0162] Performance testing:

[0163] The test measures the brightness, driving voltage, current efficiency, life test LT90 and LT90 high temperature of the prepared organic electroluminescent device. Among them, the life test LT90 refers to the current density at room temperature (25-27°C) at the initial brightness. 2 The time required for the brightness to decrease to 90% of the initial brightness is LT90 high temperature, which means the current density at the initial brightness is kept constant at 90-95℃ (here 1000cd / m 2 ), and the time it takes for the brightness to decrease to 90% of the initial brightness. The driving voltage, current efficiency, LT90, and LT90 high temperature values are all relative values. The test results are detailed in Table 6 below.

[0164] Table 6

[0165]

[0166] As can be seen from the contents of Table 4, in the present invention, by designing the structure of the triazine compound, the triazine compound is used as the main material of the light-emitting layer of the OLED device, and the OLED device prepared has a lower driving voltage, higher current efficiency, longer life and longer high-temperature life.

[0167] Device Example 9 Device Comparative Examples 6-7

[0168] Device Example 9 and Device Comparative Examples 6-7 respectively provide an organic electroluminescent device, which differs from Device Example 1 only in that the green light host material is different. The green light host is two components, and the volume ratio of the two components is 1:1 (see Table 7 below for details). The other preparation steps and conditions are the same as those of Device Example 1.

[0169] Performance testing:

[0170] The test measures the brightness, driving voltage, current efficiency, life test LT90 and LT90 high temperature of the prepared organic electroluminescent device. Among them, the life test LT90 refers to the current density at room temperature (25-27°C) at the initial brightness (here 1000cd / m 2 The time required for the brightness to decrease to 90% of the initial brightness is LT90 high temperature, which means the current density at the initial brightness is kept constant at 90-95℃ (here 1000cd / m 2 ), and the time it takes for the brightness to decrease to 90% of the initial brightness. The driving voltage, current efficiency, LT90, and LT90 high temperature values are all relative values. The test results are detailed in Table 7 below.

[0171] Table 7

[0172]

[0173] As can be seen from the above content, the present invention designs the structure of triazine compounds, thereby using triazine compounds as the main material of the light-emitting layer of OLED devices, and the resulting OLED devices have lower driving voltage, higher current efficiency, longer life and longer high-temperature life.

[0174] The applicant declares that the present invention uses the above-described embodiments to illustrate the detailed process flow of the present invention, but the present invention is not limited to the above-described detailed process flow, that is, it does not mean that the present invention must rely on the above-described detailed process flow to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent replacements for various raw materials in the products of the present invention, addition of auxiliary ingredients, and selection of specific methods, etc., are all within the scope of protection and disclosure of the present invention.

Claims

1. A triazine compound, characterized in that: The triazine compound has a structure shown in the following formula I: Wherein, R1 is selected from any one of phenyl, naphthyl, and biphenyl; R2, R3, R4, and R5 are each independently selected from any one of a hydrogen atom, a phenyl group, a naphthyl group, and a biphenyl group; At least five hydrogen atoms in the compound of formula I are not replaced by deuterium atoms, and the remaining hydrogen atoms can each independently be replaced by a deuterium atom.

2. The triazine compound according to claim 1, characterized in that The compound of formula I has any one of the structures shown in formula I-1, formula I-2 or formula I-3: Wherein, R1 is selected from any one of phenyl, naphthyl, and biphenyl; R2, R3, R4, and R5 are each independently selected from any one of a hydrogen atom, a phenyl group, a naphthyl group, and a biphenyl group; At least five hydrogen atoms in the compound of formula I-1, the compound of formula I-2, and the compound of formula I-3 are not replaced by deuterium atoms, and the remaining hydrogen atoms can each independently be replaced by a deuterium atom.

3. The triazine compound according to claim 1 or 2, characterized in that The R1 is selected from phenyl.

4. The triazine compound according to any one of claims 1 to 3, characterized in that The triazine compound is selected from any one of the following substituted or unsubstituted compounds: The substitution means that at least five hydrogen atoms in the triazine compound are not replaced by deuterium atoms, and the remaining hydrogen atoms can be independently replaced by deuterium atoms.

5. A triazine compound, characterized in that: The triazine compounds include compound D3 and compound D4:

6. A composition, characterized in that The composition comprises at least a first component and a second component, wherein the first component comprises at least one triazine compound according to any one of claims 1 to 5, and the second component comprises at least one compound having a structure shown in the following formula II: wherein R6, R7, R8, and R9 are each independently selected from a C6-C20 aryl group or a C6-C20 heteroaryl group; m, o, and p are each independently selected from an integer between 0 and 4; n is selected from an integer between 0 and 3; The hydrogen atoms in the compound of formula II may each independently be substituted by at least one of a deuterium atom, -F, -CN, a C1-C12 alkyl group, a C1-C12 alkoxy group, a triphenylsilyl group, a triphenylmethyl group, a C6-C20 aryl group or a C6-C20 heteroaryl group.

7. The composition according to claim 6, characterized in that The C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, butyl, pentyl, methylcyclopentyl, hexyl, methylcyclohexyl, heptyl, octyl, adamantyl, bicyclo[2.2.1]heptyl or bicyclo[2.2.2]octyl; Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy; Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl or 9,9-dimethylfluorenyl; Preferably, the C6-C20 heteroaryl group is selected from any one of a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group.

8. The composition according to claim 6 or 7, characterized in that m+n+o+p=0; Preferably, m+n=0, o+p=1; Preferably, m+n=0, o=0, p=1; Preferably, m+n=0, o=1, p=0; Preferably, m+n=0, o=0, p=2; Preferably, m+n=0, o=2, p=0; Preferably, m+n=0, o=1, p=1; Preferably, m=1, n=1, o=0, p=1; Preferably, m=1, n=o=0, p=1; Preferably, R6, R7, R8, and R9 are each independently selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl; Preferably, R6, R7, and R8 are each independently selected from any one of phenyl, naphthyl, or biphenyl, more preferably phenyl; Preferably, R9 is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl; Preferably, the hydrogen atoms in the compound of formula II are each independently replaced by at least one of a deuterium atom, -F, -CN, a methyl group, an ethyl group, a propyl group, a tert-butyl group, a methoxy group, an ethoxy group, a propoxy group, a phenyl group, a naphthyl group, a biphenyl group, a carbazolyl group or a triphenylsilyl group.

9. The composition according to any one of claims 6 to 8, characterized in that The compound of formula II is selected from any one of the following substituted or unsubstituted compounds: The substitution means that the hydrogen atoms in the carbazole compounds can be independently replaced by deuterium atoms.

10. 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 material of the organic thin film layer comprises the triazine compound according to any one of claims 1 to 5 or the composition according to any one of claims 6 to 9; Preferably, the organic thin film layer includes a light-emitting layer; The host material of the light-emitting layer comprises the triazine compound according to any one of claims 1 to 5 or the composition according to any one of claims 6 to 9; Preferably, the organic electroluminescent device is a green organic electroluminescent device.

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