Triazine compound, intermediate compound, composition and organic electroluminescent device

Abstract

The invention provides a triazine compound, an intermediate 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 particularly relates to a triazine compound, an intermediate compound, a composition and an organic electroluminescent device. Background Art

[0002] A display integrates electronics, communication, and information processing technologies, and is regarded as another major development opportunity for the electronics industry after electronics and computers. Display technology and displays occupy a very important position in the development process of information technology. Displays on televisions, computers, telephones, and various instruments and meters provide people with a large amount of information in daily life and work. In recent years, new display technologies have become the focus of research. Among them, flat panel displays have the advantages of small weight, low power consumption, and easy portability, and have become a research hotspot.

[0003] Among various current flat panel displays, liquid crystal displays (LCDs) play an important role. However, LCDs have many deficiencies: they do not emit light by themselves, rely on light sources or ambient light, have viewing angle problems, slow response speeds, and low resolutions. Therefore, people have been constantly looking for new flat panel display technologies. The phenomenon of organic electroluminescence was discovered as early as 1963, but it did not attract people's attention at that time. It was not until 1987 that the research group of Tang from Eastman Kodak Company in the United States published a high-brightness, high-efficiency thin-film organic electroluminescent device (OLED) made of organic fluorescent materials and hole materials driven by a direct current low voltage that this technology was re-concerned and opened up a brand-new research field.

[0004] OLEDs have outstanding advantages, such as low power consumption, fast response speed, easy bending, wide viewing angle, large-area display, and full-color emission, and can be compatible with various existing standards and technologies to make low-cost light-emitting devices, showing broad application prospects in realizing color flat panel displays. In the past few decades, OLEDs, as a new display technology, have made great progress and have been widely used in the fields of flat panel display, flexible display, solid-state lighting, and vehicle-mounted display.

[0005] The selection of hole transport layers, light-emitting layers, and other organic functional layer materials in OLED display devices will have a great impact on the current efficiency, driving voltage, and lifetime of the devices. At the same time, the application environment temperature of some current OLED devices is relatively high. Therefore, for OLED devices, a relatively high high-temperature lifetime is also required. Summary of the Invention

[0006] In view of the deficiencies of the prior art, the purpose of the present invention is to provide a triazine compound, an intermediate compound, a composition and an organic electroluminescent device. In the present invention, the structure of the triazine compound is designed, and thus the triazine compound is used as the host material of the light-emitting layer of the OLED device, and the prepared OLED device has a lower driving voltage, a higher current efficiency, a longer lifetime and a longer high-temperature lifetime.

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

[0008] In a first aspect, the present invention provides a triazine compound, and the triazine compound has the structure shown in the following formula I:

[0009]

[0010] Wherein, R1 and R4 each independently selected from a hydrogen atom or a phenyl group;

[0011] R2 and R3 each independently selected from a deuterium atom (D) or a phenyl group;

[0012] And any two of R1, R2, R3, and R4 are selected from phenyl groups, and the other two are selected from hydrogen atoms or deuterium atoms.

[0013] At least one hydrogen atom in the compound of formula I is not replaced by a deuterium atom, and the remaining hydrogen atoms may each independently be replaced by a deuterium atom.

[0014] In the present invention, the structure of the triazine compound is designed, and thus the triazine compound is used as the host material of the light-emitting layer of the OLED device, and the prepared OLED device has a lower driving voltage, a higher current efficiency and a longer lifetime.

[0015] It should be noted that in the present invention, "D" represents a deuterium atom. In the present invention, if not separately marked, H and hydrogen therein both represent a combination of protium, deuterium and tritium with natural abundances, and the same applies hereinafter.

[0016] The following are the preferred technical solutions of the present invention, but do not limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the purpose and beneficial effects of the present invention can be better achieved and realized.

[0017] As a preferred technical solution of the present invention, the compound of formula I is selected from any one of the structures shown in the following formula I-1 to I-4:

[0018]

[0019]

[0020] Wherein, R1, R2, R3, and R4 have the same definitions as above;

[0021] At least one hydrogen atom in the compound of Formula I-1 to the compound of Formula I-4 is not replaced by a deuterium atom, and the remaining hydrogen atoms may each independently be replaced by a deuterium atom.

[0022] As a preferred technical solution of the present invention, the compound of Formula I is selected from any one of the structures represented by the following Formula II-1 or II-2:

[0023]

[0024] Among them, at least one hydrogen atom in the compound of Formula II-1 or the compound of Formula II-2 is not replaced by a deuterium atom, and the remaining hydrogen atoms may each independently be replaced by a deuterium atom.

[0025] As a preferred technical solution of the present invention, the triazine compound is selected from any one of the following substituted or unsubstituted compounds:

[0026]

[0027] . The substitution means that at least one hydrogen atom in the above triazine compound is not replaced by a deuterium atom, and the remaining hydrogen atoms may each independently be replaced by a deuterium atom.

[0028] Preferably, the triazine compound includes the following compounds:

[0029]

[0030] It should be noted that the present invention does not make any special limitation on the preparation method of the provided triazine compound, and the commonly used preparation methods in the art are applicable.

[0031] In a second aspect, the present invention provides an intermediate compound, and the intermediate includes the following compounds:

[0032]

[0033]

[0034] The intermediate compound is used for preparing the triazine compound as described in the first aspect.

[0035] In a third aspect, the present invention provides a composition, and the composition includes at least a first component and a second component. The first component includes at least one triazine compound as described in the first aspect, and the second component includes at least one compound having the structure represented by the following Formula II:

[0036]

[0037] Among them, R5, R6, R7, and R8 are each independently selected from C6-C20 aryl or C6-C20 heteroaryl;

[0038] m, o, and p are each independently selected from integers between 0 and 4;

[0039] n is selected from integers between 0 and 3;

[0040] The hydrogen atoms in the compound of Formula II can each independently be replaced by a deuterium atom (-D), -F, -CN, C1-C12 alkyl, C1-C12 alkoxy, triphenylsilyl ( The dashed line indicates the connection site, and the same applies hereinafter), triphenylmethyl substituted by at least one of C6-C20 aryl or C6-C20 heteroaryl.

[0041] In the compound of Formula II, C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, or C12.

[0042] C6-C20 can be C6, C10, C12, C15, C18, or C20, etc.

[0043] Preferably, the C1-C12 alkyl 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.

[0044] Preferably, the C1-C12 alkoxy is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy, or hexyloxy.

[0045] Preferably, the C6-C20 aryl is selected from any one of phenyl, naphthyl, biphenyl, or 9,9-dimethylfluorenyl.

[0046] Preferably, the C6-C20 heteroaryl is selected from any one of carbazolyl, dibenzofuranyl, or dibenzothiophenyl.

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

[0048] As a preferred technical solution of the present invention, m + n = 0, o + p = 1.

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

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

[0051] As a preferred technical solution of the present invention, m + n = 0, o = 0, and p = 2.

[0052] As a preferred technical solution of the present invention, m + n = 0, o = 2, and p = 0.

[0053] As a preferred technical solution of the present invention, m + n = 0, o = 1, and p = 1.

[0054] As a preferred technical solution of the present invention, m = 1, n = 1, o = 0, and p = 1.

[0055] As a preferred technical solution of the present invention, m = 1, n = o = 0, and p = 1.

[0056] As a preferred technical solution of the present invention, each of R5, R6, R7, and R8 is independently selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl.

[0057] Preferably, each of R5, R6, and R7 is independently selected from any one of phenyl, naphthyl, or biphenyl, and more preferably phenyl.

[0058] Preferably, R8 is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl.

[0059] As a preferred technical solution of the present invention, each hydrogen atom in the compound of formula II can independently be replaced by at least one of deuterium atom (-D), -F, -CN, methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, propoxy, phenyl, naphthyl, biphenyl, carbazolyl, or triphenylsilyl.

[0060] 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:

[0061]

[0062]

[0063] The substitution means that each hydrogen atom in the above compound can independently be replaced by a deuterium atom.

[0064] Preferably, the compound of formula II is selected from any one of the following compounds:

[0065]

[0066] It should be noted that the present invention has no special restrictions on the preparation method of the compound of formula II, and any common preparation method in the art is applicable.

[0067] In a fourth aspect, the present invention provides an organic electroluminescent device, which includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;

[0068] The material of the organic thin film layer includes the triazine compound as described in the first aspect or the composition as described in the third aspect.

[0069] Preferably, the organic thin film layer includes a light-emitting layer;

[0070] The host material of the light-emitting layer includes the triazine compound as described in the first aspect or the composition as described in the third aspect.

[0071] As a preferred technical solution of the present invention, the organic electroluminescent device is a green organic electroluminescent device.

[0072] In the present invention, the light-emitting layer includes a light-emitting layer host material and a doping material, where the doping material is also called a dye or a phosphorescent material. The light-emitting layer host material can be a single compound or a mixture formed by two or more compounds.

[0073] 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.

[0074] The volume percentage content of the host material in the phosphorescent light-emitting layer is 60% - 99.9% (for example, it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98% or 99.9%, etc.), preferably 70% - 99.5%, and further preferably 85% - 95%.

[0075] In the present invention, the doping material of the light-emitting layer can be a phosphorescent material. The phosphorescent material, also known as a triplet light-emitting material, refers to the light emitted by a substance from a triplet excited state. In the present invention, no special limitation is made on the specific selection of the phosphorescent material. Commonly used doping materials for the light-emitting layer in the art are applicable. Exemplarily, but not limited to, compounds having the structure shown in formula PD:

[0076]

[0077] Among them, M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu, or Au;

[0078] Y1 - Y4 are each independently selected from carbon or nitrogen;

[0079] A single bond or a double bond can connect between Y1 and Y2, and a single bond or a double bond can connect between Y3 and Y4;

[0080] 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, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuryl, benzothienyl, isobenzothienyl, benzimidazazolyl, benzoxazolyl, triazolyl, tetrazolyl, dioxazolyl, triazinyl, dibenzofuryl, dibenzothienyl, N-heterocarbazolyl, N-heterodibenzofuryl, provided that Cy1 and Cy2 may optionally be connected to each other via a single bond or an organic linking group;

[0081] Between any two ligands of M, or between more than two ligands, they can be connected by a single bond or a double bond, or can be bridged by O or S, or can be connected by any chemical group or chemical structure to form a structural form that conforms to chemical principles;

[0082] R 91 and R 92Each independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazone group, carboxylic acid group, carboxylate group, sulfonic acid group, sulfonate group, phosphoric acid group, phosphate group, -SF5, substituted or unsubstituted C1-C60 (such as C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkyl, substituted or unsubstituted C2-C60 (such as C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkenyl, substituted or unsubstituted C2-C60 (such as C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkynyl, substituted or unsubstituted C1-C60 (such as C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkoxy, substituted or unsubstituted C2-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9 or C10) heterocycloalkyl, substituted or unsubstituted C6-C60 (such as C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) aryl, substituted or unsubstituted C6-C60 (such as C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) aryloxy, substituted or unsubstituted C6-C60 (such as C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) arylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0083] a1 and a2 are each independently an integer selected from 1-5, such as 1, 2, 3, 4 or 5;

[0084] b is selected from integers from 0-4, such as 0, 1, 2, 3 or 4;

[0085] a is selected from 1, 2 or 3;

[0086] L1 is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

[0087] Preferably, the PD compound of the formula is selected from any one of the following compounds:

[0088]

[0089]

[0090]

[0091]

[0092]

[0093] In a fourth aspect, the present invention provides a display device, and the display device includes the organic electroluminescent device as described in the third aspect.

[0094] Compared with the prior art, the present invention has the following beneficial effects:

[0095] In the present invention, by designing the structure of the triazine compound, the triazine compound is used as the host material of the light-emitting layer of the OLED device, and the prepared OLED device has a lower driving voltage, a higher current efficiency, a longer lifetime, and a longer high-temperature lifetime. Specific Embodiments

[0096] To facilitate the understanding of the present invention, the following examples are listed for the present invention. Those skilled in the art should understand that the examples are only for helping to understand the present invention and should not be regarded as specific limitations on the present invention.

[0097] Preparation Example 1

[0098] This preparation example provides intermediate M1 and its synthesis method, and the synthesis method is as follows:

[0099]

[0100] 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), copper oxide (0.1 g), and o-phenanthroline (0.2 g) were added to a three-necked flask. First, the reaction was carried out at 80 °C for 4 h, then the temperature was raised to 120 °C for 6 h, and then cooled. The insoluble substances were filtered off, washed with water, separated by liquid, the organic layer was washed with water until neutral, dried over anhydrous magnesium sulfate, the desiccant was filtered off, and then concentrated to dryness, and crystallized with ethanol to obtain intermediate M1 (2.1 g).

[0101] The intermediate M1 was detected by mass spectrometry, and the measured mass-to-charge ratio m / z was 377.08.

[0102] Preparation Examples 2-3

[0103] 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:

[0104] Table 1

[0105]

[0106] Synthesis Example 1 Synthesis of Compound P1

[0107] This synthesis example provides compound P1 and its synthesis method, the synthesis method is as follows:

[0108]

[0109] 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).

[0110] Compound P1 was subjected to mass spectrometry detection: its mass-to-charge ratio (m / z) was measured to be 464.23.

[0111] Synthesis Examples 2-5

[0112] 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:

[0113] Table 2

[0114]

[0115] Synthesis Example 6 Synthesis of Compound A1

[0116] This synthesis example provides compound A1 and its synthesis method, the synthesis method is as follows:

[0117]

[0118] (1) Synthesis of Intermediate A1-3

[0119] Under nitrogen, 60 mL of toluene, 20 mL of ethanol, and 10 mL of water were added to a three-necked flask, followed by 3.2 g of intermediate A1-4, 1.2 g of phenylboric acid, 2.12 g of sodium carbonate, and 0.23 g of tetrakistriphenylphosphine palladium. The temperature was slowly raised to 40 ° C. for reaction for 6 h, then raised to reflux for reaction for 1 h, cooled to room temperature, and water was added to separate the organic layer. After washing with water, the organic layer was dried with magnesium sulfate, the desiccant was removed, and the silica gel column was separated and eluted with petroleum ether to obtain intermediate A1-3 (1.7 g).

[0120] The obtained intermediate A1-3 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 268.97.

[0121] (2) Synthesis of Intermediate A1-2

[0122] Under nitrogen protection, dry toluene (50 mL), intermediate A1-3 (2.7 g), carbazole (1.7 g), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.0575 g), 10% tri-tert-butylphosphine toluene solution (the mass of tri-tert-butylphosphine solution is 0.4 g, the amount of tri-tert-butylphosphine is 0.0002 mol) and sodium tert-butoxide (1.44 g) were added to a three-necked flask and heated to reflux. After the reaction was completed for 8 h, the mixture was cooled to room temperature and separated by adding water. The organic layer was then washed with water until neutral, dried over magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, and separated by silica gel column chromatography and eluted with a solvent of petroleum ether: ethyl acetate = 20:1 (volume ratio) to obtain intermediate A1-2 (2.1 g).

[0123] The intermediate A1-2 was subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) was measured to be 356.12.

[0124] (3) Synthesis of Compound A1

[0125] Under a nitrogen atmosphere, 100 mL of toluene was added to a three-necked flask, followed by 3.5 g of intermediate A1-2, 5.5 g of intermediate A1-1, 2.12 g of sodium carbonate, and 0.1 g of dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (II) (CAS No. 887919-35-9). The temperature was slowly raised to reflux for 12 hours, then cooled to room temperature, and water was added to separate the layers. The organic layer was washed with water, dried over magnesium sulfate, and after removing the desiccant, the mixture was concentrated to dryness and separated by silica gel column chromatography with petroleum ether: dichloromethane = 10:2 (volume ratio) to give compound A1 (2.9 g).

[0126] The obtained compound A1 was subjected to mass spectrometry detection, and the mass-to-charge ratio (m / z) was measured to be 719.28.

[0127] Among them, the synthesis of intermediate A1-1 is as follows:

[0128]

[0129] Under nitrogen protection, 5.3 g of compound A1-0, 4.0 g of bis(pinacolato)diboron, 60 mL of isopropanol, 2.2 g of triethylamine, 0.1 g of bis(1,5-cyclooctadiene)nickel(0), and 0.18 g of triphenylphosphine were added to a three-necked flask. The temperature was raised to 35 °C and the reaction was carried out for 6 h, then the temperature was raised to 50 °C and the reaction was carried out for 2 h. Water and ethyl acetate were added for liquid separation. The organic layer was washed with water until neutral, dried over anhydrous magnesium sulfate, the desiccant was filtered off, and then concentrated to dryness. Column chromatography on silica gel was carried out, and elution was carried out with petroleum ether:ethyl acetate = 10:1 (volume ratio) to obtain intermediate A1-1 (3.6 g).

[0130] The obtained intermediate A1-1 was subjected to mass spectrometry detection, and the m / z was 525.22.

[0131] Synthesis of Compound B1 in Synthesis Example 7

[0132] This synthesis example provides compound B1 and its synthesis method. The synthesis method is as follows:

[0133]

[0134] Referring to the synthesis method of compound A1, compound B1 was prepared.

[0135] The obtained compound B1 was subjected to mass spectrometry detection, and the measured mass-to-charge ratio (m / z) was 719.28.

[0136] Among them, the synthesis of intermediate B1-1 is as follows:

[0137]

[0138] Referring to the synthesis method of compound A1-1, compound B1-1 was prepared.

[0139] The obtained intermediate B1-1 was subjected to mass spectrometry detection, and the m / z was 525.22.

[0140] Synthesis of Compound C1 in Synthesis Example 8

[0141] This synthesis example provides compound C1 and its synthesis method. The synthesis method is as follows:

[0142]

[0143] (1) Synthesis of intermediate C1-2

[0144] Referring to the synthesis of intermediate A1-3, intermediate C1-2 was prepared.

[0145] The obtained intermediate C1-2 was subjected to mass spectrometry, and the m / z was 498.06.

[0146] (2) Synthesis of intermediate C1-1

[0147] Under nitrogen, 80 mL of toluene, 40 mL of ethanol, and 20 mL of water were added to a three-necked flask, and then 5.0 g of intermediate C1-2, 1.2 g of phenylboronic acid, 2.12 g of sodium carbonate, and 0.23 g of tetrakis(triphenylphosphine)palladium were added thereto. The temperature was slowly raised to reflux for 6 h, and then cooled to room temperature. Water was added for liquid separation. After the organic layer was washed with water, it was dried with magnesium sulfate. After removing the desiccant, it was separated by silica gel column chromatography and eluted with petroleum ether:dichloromethane = 10:2 (volume ratio) to obtain intermediate C1-1 (1.7 g).

[0148] The obtained intermediate C1-1 was subjected to mass spectrometry, and the measured mass-to-charge ratio (m / z) was: 496.18.

[0149] (3) Synthesis of compound C1

[0150] Under nitrogen protection, 100 mL of dimethyl sulfoxide, 5.0 g of intermediate C1-1, 2.5 g of 2-phenylcarbazole, and 6.3 g of cesium carbonate were added to a three-necked flask and reacted at 100 °C for 20 h. After cooling, water was added, and the solid was filtered. After drying, it was crystallized 3 times with a mixed solvent of toluene and chloroform to obtain compound C1 (1.3 g).

[0151] The obtained compound C1 was subjected to mass spectrometry, and the measured mass-to-charge ratio (m / z) was 719.28.

[0152] Synthesis of compound D1 in Synthesis Example 9

[0153] This synthesis example provides compound D1 and its synthesis method. The synthesis method is as follows:

[0154]

[0155] (1) Synthesis of intermediate D1-2

[0156] Referring to the synthesis of intermediate C1-2, intermediate D1-2 was prepared.

[0157] The obtained intermediate D1-2 was subjected to mass spectrometry, and the m / z was 498.06.

[0158] (2) Synthesis of intermediate D1-1

[0159] Referring to the synthesis of intermediate C1-1, intermediate D1-1 was prepared.

[0160] The obtained intermediate D1-1 was subjected to mass spectrometry, and the m / z was 496.18.

[0161] (3) Synthesis of Compound D1

[0162] Refer to the synthesis of Compound C1 to prepare Compound D1.

[0163] Perform mass spectrometry detection on the obtained Compound D1, and the m / z is 719.28.

[0164] Synthesis of Compound E1 in Synthesis Example 10

[0165] This synthesis example provides Compound E1 and its synthesis method. The synthesis method is as follows:

[0166]

[0167] (1) Synthesis of Intermediate E1-2

[0168] Refer to the synthesis of Intermediate C1-2 to prepare Intermediate E1-2.

[0169] Perform mass spectrometry detection on the obtained Intermediate E1-2, and the m / z is 574.09.

[0170] (2) Synthesis of Intermediate E1-1

[0171] Refer to the synthesis of Intermediate C1-1 to prepare Intermediate E1-1.

[0172] Perform mass spectrometry detection on the obtained Intermediate E1-1, and the m / z is 572.21.

[0173] (3) Synthesis of Compound E1

[0174] Refer to the synthesis of Compound C1 to prepare Compound E1.

[0175] Perform mass spectrometry detection on the obtained Compound E1, and the m / z is 719.28.

[0176] Synthesis of Compound F1 in Synthesis Example 11

[0177] This synthesis example provides Compound F1 and its synthesis method. The synthesis method is as follows:

[0178] (1) Synthesis of Intermediate F1-2

[0179] Refer to the synthesis of Intermediate A1-3 to prepare Intermediate F1-2.

[0180] Perform mass spectrometry detection on the obtained Intermediate F1-2, and the m / z is 268.97.

[0181] (2) Synthesis of Intermediate F1-1

[0182] With reference to the synthesis of intermediate A1-2, intermediate F1-1 was prepared.

[0183] The obtained intermediate F1-1 was subjected to mass spectrometry, and the m / z was 432.15.

[0184] (3) Synthesis of compound F1

[0185] With reference to the synthesis of compound A1, compound F1 was prepared.

[0186] The obtained compound F1 was subjected to mass spectrometry, and the m / z was 719.28.

[0187] For the synthesis of other unlisted compounds, the above examples can be referred to and combined with the common general knowledge in the art. The specific structures of some compounds used in the following device examples and device comparative examples are as follows:

[0188]

[0189]

[0190] Device Example 1

[0191] This device example 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.

[0192] 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).

[0193] The preparation process of the organic electroluminescent device is as follows:

[0194] The preparation method of the green light organic electroluminescent device is as follows:

[0195] The materials were placed in a vacuum chamber, and the vacuum was pumped to 1×10 -5 ~1×10 -6 Pa, and then vacuum-evaporated onto the cleaned ITO substrate in sequence to prepare the OLED device.

[0196] Where 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.

[0197] The green light host material of the green light organic electroluminescent device provided in this application example is compound A1.

[0198] Device Example 2, Device Comparative Examples 1-3

[0199] Device Example 2, Device Comparative Examples 1-3 respectively provide an organic electroluminescent device, which is only different from Device Example 1 in that the green light host material is different (see Table 3 below), and other preparation steps and conditions are the same as those in Device Example 1.

[0200] Performance Test:

[0201] The brightness, driving voltage, current efficiency, lifetime test LT90 and LT90 at high temperature of the prepared organic electroluminescent device were measured. Among them, the lifetime test LT90 refers to the time required for the brightness to decrease to 90% of the initial brightness while keeping the current density at the initial brightness unchanged (here it is the current density at 1000 cd / m 2 ), and LT90 at high temperature refers to the time required for the brightness to decrease to 90% of the initial brightness while keeping the current density at the initial brightness unchanged (here it is 1000 cd / m 2 ) at 90-95°C. The driving voltage, current efficiency, LT90, and LT90 at high temperature are all relative values. The test results are shown in Table 3 below.

[0202] Table 3

[0203]

[0204] For Compound A1 and Compound A2, the electron-withdrawing group (triazine ring) and the electron-donating group (carbazole group) in the molecular structure are connected to the same benzene ring. After this benzene ring is deuterated, the energy transfer between the triazine ring and the carbazole ring of the excited state molecule is hindered, so that its energy can be better transferred to the dye, improving the voltage and efficiency of the device. In addition, the deuteration of this benzene ring changes the charge distribution in the material molecule, making the material more stable, especially at high temperatures, with particularly outstanding performance, thus improving the LT90 at high temperature of the device and expanding the application temperature range of the material.

[0205] From the above content, it can be seen that in the present invention, by designing the structure of the triazine compound, the triazine compound is used as the host material of the light-emitting layer of the OLED device, and the prepared OLED device has a lower driving voltage, a higher current efficiency, a longer lifetime, and a longer high-temperature lifetime.

[0206] Device Example 3, Device Comparative Examples 4-6

[0207] Device Example 3, Device Comparative Examples 4-6 respectively provide an organic electroluminescent device, which is only different from Device Example 1 in that the green light host material is different (see Table 4 below), and other preparation steps and conditions are the same as those in Device Example 1.

[0208] Performance Test:

[0209] The test measured the brightness, driving voltage, current efficiency of the prepared organic light-emitting device, the LT90 of the lifetime test, and the LT90 at high temperature. Among them, the LT90 of the lifetime test refers to the time required for the brightness to decrease to 90% of the initial brightness while keeping the current density at the initial brightness unchanged (here it is the current density at 1000 cd / m 2 ), and the LT90 at high temperature refers to the time required for the brightness to decrease to 90% of the initial brightness while keeping the current density at the initial brightness unchanged (here it is 1000 cd / m 2 ). The driving voltage, current efficiency, LT90, and LT90 at high temperature are all relative values. The test results are shown in Table 4 below.

[0210] Table 4

[0211]

[0212] Device Example 4, Device Comparative Example 7

[0213] Device Example 4 and Device Comparative Example 7 respectively provide an organic light-emitting device, which is only different from Device Example 1 in that the green host material is different (see Table 5 below), and other preparation steps and conditions are the same as those of Device Example 1.

[0214] Performance Test:

[0215] The test measured the brightness, driving voltage, current efficiency of the prepared organic light-emitting device, the LT90 of the lifetime test, and the LT90 at high temperature. Among them, the LT90 of the lifetime test refers to the time required for the brightness to decrease to 90% of the initial brightness while keeping the current density at the initial brightness unchanged (here it is the current density at 1000 cd / m 2 ), and the LT90 at high temperature refers to the time required for the brightness to decrease to 90% of the initial brightness while keeping the current density at the initial brightness unchanged (here it is 1000 cd / m 2 ). The driving voltage, current efficiency, LT90, and LT90 at high temperature are all relative values. The test results are shown in Table 5 below.

[0216] Table 5

[0217]

[0218] As can be seen from the above, in the present invention, by designing the structure of the triazine compound, the triazine compound is used as the host material of the light-emitting layer of the OLED device, and the prepared OLED device has a lower driving voltage, a higher current efficiency, a longer lifetime, and a longer high-temperature lifetime.

[0219] Device Examples 5-7

[0220] Device Examples 5-7 respectively provide an organic electroluminescent device, which is different from Device Example 1 only in that the green light host material is different, and PGD-1 is replaced by PGD-2 (see Table 6 below for details), and other preparation steps and conditions are the same as those in Device Example 1.

[0221] Performance Test:

[0222] The brightness, driving voltage, current efficiency, lifetime test LT90, and LT90 high temperature of the prepared organic electroluminescent device were measured. Among them, the lifetime test LT90 refers to the time required for the brightness to decrease to 90% of the initial brightness while keeping the current density at the initial brightness unchanged (here it is the current density at 1000 cd / m 2 at room temperature (25-27 °C)), and LT90 high temperature refers to the time required for the brightness to decrease to 90% of the initial brightness while keeping the current density at the initial brightness unchanged (here it is 1000 cd / m 2 ). The driving voltage, current efficiency, LT90, and LT90 high temperature are all relative values. See Table 6 below for the test results.

[0223] Table 6

[0224]

[0225] As can be seen from the above, in the present invention, by designing the structure of the triazine compound, the triazine compound is used as the host material of the light-emitting layer of the OLED device, and the prepared OLED device has a lower driving voltage, a higher current efficiency, a longer lifetime, and a longer high-temperature lifetime.

[0226] Device Example 8, Device Comparative Examples 8-9

[0227] Device Example 8, Device Comparative Examples 8-9 respectively provide an organic electroluminescent device, which is different from Device Example 1 only in that the green light host material is different, the green light host is composed of two components, and the volume ratio of the two components is 1:1 (see Table 7 below for details), and other preparation steps and conditions are the same as those in Device Example 1.

[0228] Performance Test:

[0229] The tests measured the luminance, driving voltage, current efficiency of the fabricated organic light-emitting devices, the LT90 of the lifetime test, and the LT90 at high temperature. Among them, the LT90 of the lifetime test refers to the time required for the luminance to decrease to 90% of the initial luminance while keeping the current density at the initial luminance unchanged (here it is the current density at 1000 cd / m 2 ), and the LT90 at high temperature refers to the time required for the luminance to decrease to 90% of the initial luminance while keeping the current density at the initial luminance unchanged (here it is 1000 cd / m 2 ) at 90-95°C. The driving voltage, current efficiency, LT90, and LT90 at high temperature are all relative values. The test results are shown in Table 7 below.

[0230] Table 7

[0231]

[0232] As can be seen from the above, in the present invention, by designing the structure of the triazine compound, the triazine compound is used as the host material of the light-emitting layer of the OLED device, and the fabricated OLED device has a lower driving voltage, a higher current efficiency, a longer lifetime, and a longer lifetime at high temperature.

[0233] The applicant declares that the present invention uses the above embodiments to illustrate the detailed process flow of the present invention, but the present invention is not limited to the above detailed process flow, that is, it does not mean that the present invention must rely on the above detailed process flow to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent substitution of each raw material of the product of the present invention, the addition of auxiliary components, and the selection of specific methods, etc., all fall within the protection scope and the disclosure scope of the present invention.

Claims

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

2. The triazine compound according to claim 1, wherein The compound of formula I is selected from any one of the structures shown in the following formulae I-1 to I-4: Wherein, R1, R2, R3, and R4 have the same definitions as in claim 1; At least one hydrogen atom in the compounds of formula I-1 to I-4 is not replaced by a deuterium atom, 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 compound of formula I is selected from any one of the structures shown in the following formula II-1 or II-2: Wherein, at least one hydrogen atom in the compound of formula II-1 or II-2 is not replaced by a deuterium atom, and the remaining hydrogen atoms can each independently be replaced by a deuterium atom.

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

5. An intermediate compound, characterized in that, The intermediate compound includes the following compounds: The intermediate compound is used to prepare the triazine compound according to any one of claims 1-4.

6. A composition, characterized in that, The composition includes at least a first component and a second component. The first component includes at least one triazine compound according to any one of claims 1-4, and the second component includes at least one compound having the structure shown in the following formula II: Wherein, R5, R6, R7, and R8 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 integers between 0 and 4; n is selected from an integer between 0 and 3; The hydrogen atoms in the compound of formula II can 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, wherein 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 carbazolyl, dibenzofuranyl, or dibenzothiophenyl; 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, each of R5, R6, R7, and R8 is independently selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl; Preferably, each of R5, R6, and R7 is independently selected from any one of phenyl, naphthyl, or biphenyl, more preferably phenyl; Preferably, R8 is selected from any one of phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl; Preferably, each hydrogen atom in the compound of formula II can independently be replaced by at least one of deuterium atom, -F, -CN, methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, propoxy, phenyl, naphthyl, biphenyl, carbazolyl, or triphenylsilyl.

9. The composition according to any one of claims 6 - 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 each hydrogen atom in the above compound can independently be replaced by a deuterium atom.

10. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode; The material of the organic thin film layer includes the triazine compound according to any one of claims 1-4 or the composition according to any one of claims 6-9; Preferably, the organic thin film layer includes a light-emitting layer; The host material of the light-emitting layer includes the triazine compound according to any one of claims 1-4 or the composition according to any one of claims 6-9.

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