Triazine deuterated compound, intermediate and organic electroluminescent device

Abstract

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

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a triazine-based deuterated compound, an intermediate, and an organic electroluminescent device. Background Art

[0002] The 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 have occupied 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 current various flat panel displays, liquid crystal displays (LCDs) have an important position. 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 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 when 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 achieved great development and have been widely used in the fields of flat panel display, flexible display, solid-state lighting, and vehicle-mounted display.

[0005] Therefore, developing more types of OLED materials with more perfect performance to meet the usage requirements of high-performance OLED devices is the research focus in this field. Summary of the Invention

[0006] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide a triazine-based deuterated compound, an intermediate, and an organic electroluminescent device. In the present invention, by designing the structure of the triazine-based deuterated compound, the triazine-based deuterated 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 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 deuterated compound, and the triazine deuterated compound has a structure shown in the following formula I:

[0009]

[0010] Wherein, Ar 11 、Ar 12 、Ar 13 are each independently selected from any one of C6-C40 aryl or C6-C30 heteroaryl; Ar is selected from any one of a single bond, C6-C40 arylene or C6-C30 heteroarylene;

[0011] X 1 、X 2 、X 3 are each independently selected from N or CH, and at least one of X 1 、X 2 、X 3 is selected from N;

[0012] Ar, Ar 11 、Ar 12 、Ar 13 The hydrogen atoms in can each independently be replaced by deuterium atoms (D);

[0013] The hydrogen atoms in the compound of formula I can each independently be substituted by at least one of -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy;

[0014] The triazine deuterated compound does not include the following compounds:

[0015]

[0016]

[0017]

[0018] In the present invention, the triazine deuterated compound has a structure shown in the above formula I, and the compound of formula I is obtained by fusing any two adjacent carbon atoms on the ring Q in the structure of formula I-A with the group of formula I-B, and "*" represents the fusion site of the group of formula I-B;

[0019] In addition to the two carbon atoms on the ring Q that are fused with the group of formula I-B, the other two carbon atoms are connected with D atoms;

[0020]

[0021] Among them, Ar 11 、Ar 12 、Ar 13 、X 1 、X 2 、X 3 have the same definitions as above.

[0022] In the present invention, by designing the structure of the triazine-based deuterated compound, the triazine-based deuterated 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 lifespan.

[0023] In the present invention, C6-C40 can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.

[0024] C6-C30 can be C6, C8, C10, C12, C16, C20, C24, C28, or C30, etc.

[0025] C6-C20 can be C6, C8, C10, C12, C16, or C20, etc.

[0026] C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, or C12.

[0027] It should be noted that in the present invention, "D" represents a deuterium atom. If not separately marked in the present invention, H and hydrogen therein both represent "protium", and the same applies hereinafter.

[0028] 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 objectives and beneficial effects of the present invention can be better achieved and realized.

[0029] As a preferred technical solution of the present invention, the C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylene, fluoranthenyl, hydrobenzanthryl, indenoindenyl, benzindenoindenyl, dibenzindenoindenyl, naphthofluorenyl, triphenylmethyl, triphenylsilyl, or benzonaphthofluorenyl.

[0030] As a preferred technical solution of the present invention, the C6-C30 heteroaryl group is selected from any one or a combination of at least two of carbazolyl, dibenzothiophenyl, dibenzofuranyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, or dinaphthothiophenyl.

[0031] Preferably, the C6-C20 aryl is selected from any one of phenyl, naphthyl, biphenyl, anthryl, phenanthryl, fluorenyl, triphenylenyl or fluoranthenyl.

[0032] Preferably, the C1-C12 alkyl is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl, adamantyl.

[0033] Preferably, the C1-C12 alkoxy is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy.

[0034] As a preferred technical solution of the present invention, Ar is selected from any one of a single bond, phenylene, biphenylene, naphthylene, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl;

[0035] The hydrogen atoms in Ar can be independently replaced by deuterium atoms.

[0036] Preferably, Ar is selected from a single bond or phenylene.

[0037] Preferably, Ar is selected from a single bond.

[0038] Preferably, Ar is selected from phenylene.

[0039] Preferably, some of the hydrogen atoms in Ar are replaced by deuterium atoms.

[0040] Preferably, all of the hydrogen atoms in Ar are replaced by deuterium atoms.

[0041] As a preferred technical solution of the present invention, the Ar 11 , Ar 12 , Ar 13 are each independently selected from at least one of phenyl, biphenyl, terphenyl, naphthyl, triphenylenyl, fluoranthenyl, anthryl, phenanthryl, 9,9-dimethylfluorenyl, carbazolyl, dibenzothiophenyl or dibenzofuranyl;

[0042] The Ar 11 , Ar 12 , Ar 13 in the hydrogen atoms are each independently replaced by deuterium atoms.

[0043] Preferably, the Ar 11 is selected from any one of phenyl, biphenyl, terphenyl, naphthyl;

[0044] The Ar 11 in the hydrogen atoms are each independently replaced by deuterium atoms.

[0045] Preferably, the Ar12 and Ar 13 are each independently selected from any one of phenyl, biphenyl, terphenyl, naphthyl, triphenylene, fluoranthenyl, phenanthryl, anthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl or 9,9-dimethylfluorenyl, and more preferably any one of phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl;

[0046] Said Ar 12 and Ar 13 the hydrogen atoms in are each independently replaced by deuterium atoms.

[0047] Preferably, said Ar 11 is selected from phenyl, said Ar 12 and Ar 13 any one of them is selected from phenyl, and the other is selected from any one of biphenyl, terphenyl, naphthyl, triphenylene, fluoranthenyl, anthryl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl or 9,9-dimethylfluorenyl;

[0048] Said Ar 11 and Ar 12 and Ar 13 the hydrogen atoms in are each independently replaced by deuterium atoms.

[0049] Preferably, said Ar 11 is selected from biphenyl, said Ar 12 and Ar 13 are both selected from phenyl;

[0050] Said Ar 11 and Ar 12 and Ar 13 the hydrogen atoms in are each independently replaced by deuterium atoms.

[0051] Preferably, said Ar 11 is selected from biphenyl, said Ar 12 and Ar 13 any one of them is selected from phenyl, and the other is selected from biphenyl;

[0052] Said Ar 11 and Ar 12 and Ar 13 the hydrogen atoms in are each independently replaced by deuterium atoms.

[0053] Preferably, any one of said Ar 12 and Ar 13 is selected from terphenyl;

[0054] Said Ar 12 and Ar 13 the hydrogen atoms in are each independently replaced by deuterium atoms.

[0055] As a preferred technical solution of the present invention, the hydrogen atoms in the compound of formula I can each independently be substituted by at least one of -F, -CN, phenyl, naphthyl, methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, propoxy, triphenylmethyl, and triphenylsilyl.

[0056] As a preferred technical solution of the present invention, the triazine deuterated compound has any one of the structures shown in the following formulas I-1 to I-4:

[0057]

[0058] Wherein, Ar 11 、Ar 12 、Ar 13 、X 1 、X 2 、X 3 have the same definitions as above;

[0059] Ar, Ar 11 、Ar 12 、Ar 13 The hydrogen atoms in can each independently be replaced by deuterium atoms;

[0060] The hydrogen atoms in the compounds of formula I-1 to I-4 can each independently be substituted by at least one of -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl, or C1-C12 alkoxy.

[0061] As a preferred technical solution of the present invention, the triazine deuterated compound is selected from any one of the following substituted or unsubstituted compounds:

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] The substitution means that in the above triazine deuterated compound, the hydrogen atoms on the corresponding position groups of Ar, Ar 11 、Ar 12 、Ar 13 can each independently be replaced by deuterium atoms.

[0068] Such as Among them, Ar is a phenylene group. When all the hydrogen atoms on Ar are replaced by deuterium atoms, Ar 11 is a phenyl group. When all the hydrogen atoms on Ar 11 are replaced by deuterium atoms, Ar 12 and Ar 13 are both phenyl groups. When all the hydrogen atoms on Ar 12 and Ar 13 are replaced by deuterium atoms,

[0069] Preferably, the triazine-based deuterated compound includes the following compounds:

[0070]

[0071]

[0072] It should be noted that the present invention does not make any special limitations on the preparation method of the triazine-based deuterated compound, and any commonly used preparation method in the art is applicable.

[0073] Illustrate by way of example that the synthesis method of the triazine-based deuterated compound of the present invention includes the following steps:

[0074]

[0075] Among them, X and Y each independently selected from any one of -F, -Cl, -Br or -I;

[0076] X 1 and X 2 and X 3 and Ar, Ar 11 and Ar 12 and Ar 13 have the same definitions as above;

[0077] The hydrogen atoms on Ar, Ar 11 and Ar 12 and Ar 13 can each independently be replaced by deuterium atoms;

[0078] The hydrogen atoms in the compound of formula I can each independently be replaced by at least one of -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy.

[0079] In the second aspect, the present invention provides an intermediate, and the intermediate has the structure shown in formula MA below;

[0080]

[0081] Among them, Ar 11 has the same definition as above;

[0082] Each hydrogen atom in the intermediate can be independently substituted by at least one of -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl, or C1-C12 alkoxy;

[0083] The intermediate does not include the following compounds:

[0084]

[0085] The intermediate is used to prepare the triazine deuterated compound as described in the first aspect.

[0086] As a preferred technical solution of the present invention, the intermediate includes the following compounds:

[0087]

[0088] In a third 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;

[0089] The material of the organic thin film layer includes the triazine deuterated compound as described in the first aspect.

[0090] Preferably, the organic thin film layer includes a light-emitting layer;

[0091] The host material of the light-emitting layer includes the triazine deuterated compound as described in the first aspect.

[0092] As a preferred technical solution of the present invention, the organic electroluminescent device is a green organic electroluminescent device.

[0093] 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.

[0094] 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.

[0095] The volume percentage content of the host 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 further preferably 85% to 95%.

[0096] In the present invention, the doping material of the light-emitting layer may be selected from phosphorescent materials, also known as triplet light-emitting materials, which refer to the light emitted by a substance from the triplet excited state. In the present invention, the specific selection of the phosphorescent material is not particularly limited, and the doping materials of the light-emitting layer commonly used in the art are applicable. Exemplarily, but not limited to, compounds having the structure shown in formula PD:

[0097]

[0098] Among them, M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu or Au;

[0099] Y 1 -Y 4 Each independently is selected from carbon or nitrogen;

[0100] Y 1 and Y 2 can be connected by a single bond or a double bond, and Y 3 and Y 4 can be connected by a single bond or a double bond;

[0101] Cy 1 and Cy 2 Each independently is selected from 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, benzazolyl, triazolyl, tetrazolyl, dioxazolyl, triazinyl, dibenzofuryl, dibenzothienyl, N-heterocarbazolyl, N-heterodibenzofuryl, etc., and Cy 1 and Cy 2 can optionally be connected to each other via a single bond or an organic linking group;

[0102] Between any two ligands of M, between two or more ligands, they can be connected by a single bond, a double bond, or can be bridged by O, S, or can be connected by any chemical group or chemical structure to form a structural form that conforms to chemical principles;

[0103] R 91 and R 92 Each independently is 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, -SF 5, any one of 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.

[0104] a 1 and a 2 are each independently an integer selected from 1-5, such as 1, 2, 3, 4 or 5;

[0105] b is selected from integers from 0-4, such as 0, 1, 2, 3 or 4;

[0106] a is selected from 1, 2 or 3;

[0107] L 1 is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

[0108] Preferably, the PD compound of the formula is any one of the following compounds:

[0109]

[0110]

[0111]

[0112]

[0113] In a fourth aspect, the present invention provides a display device, comprising the organic electroluminescent device as described in the third aspect.

[0114] Compared with the prior art, the present invention has the following beneficial effects:

[0115] In the present invention, the structure of the triazine deuterated compound is designed so that the triazine deuterated compound is used as the main 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 lifespan. DETAILED DESCRIPTION

[0116] 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.

[0117] Preparation Example 1 Synthesis of Intermediate M1

[0118] This preparation example provides an intermediate M1 and a synthesis method thereof, and the synthesis method is as follows:

[0119]

[0120] Under nitrogen protection, dry toluene (60 mL), compound M0 (2.6 g), bromobenzene (1.5 g), Pd (dba) were added to a three-necked flask. 2 (bis(dibenzylideneacetonepalladium, 0.0575 g), 10% tri-tert-butylphosphine toluene solution (the mass of tri-tert-butylphosphine solution is 0.4 g, and the amount of tri-tert-butylphosphine is 0.0002 mol) and sodium tert-butoxide (1.44 g), heated to reflux, reacted for 8 hours, cooled to room temperature, added water to separate, and then the organic layer was washed with water until neutral, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, separated by silica gel column chromatography, eluted with a solvent of petroleum ether: ethyl acetate = 20: 1 (volume ratio), to obtain intermediate M1 (2.1 g).

[0121] The intermediate M1 was subjected to mass spectrometry detection: the mass-to-charge ratio (m / z) was measured to be 334.14.

[0122] Preparation Example 2-5

[0123] Preparation Examples 2-5 respectively provide an intermediate compound and its synthesis method. The corresponding intermediate compound refers to the synthesis method of Intermediate M1, and uses Chemical Raw Material 1 and Raw Material 2 (as shown in Table 1 below) to react to prepare the corresponding intermediate, as shown in Table 1 below. The mass spectrometry of the prepared intermediate was characterized, and its (m / z) value was recorded. See Table 1 below for details.

[0124] Table 1

[0125]

[0126] Among them, the synthesis method of Compound M5-2 is as follows:

[0127]

[0128] (1) Synthesis of Intermediate M5-1

[0129] Under nitrogen, add toluene (60 mL), ethanol (30 mL), and water (10 mL) to a three-necked flask, and then add deuterated o-dibromobenzene (1.2 g), o-nitrophenylboronic acid (1.8 g), sodium carbonate (2.12 g), and tetrakis(triphenylphosphine)palladium (0.46 g). Slowly heat to reflux for 10 h, cool to room temperature, add water and separate the layers. After washing the organic layer with water, dry it with magnesium sulfate. After removing the desiccant, concentrate to dryness, and crystallize with a mixed solvent of toluene and methanol to obtain Intermediate M5-1 (0.56 g).

[0130] The obtained Intermediate M5-1 was subjected to mass spectrometry detection, and the measured mass-to-charge ratio (m / z) was: 324.10.

[0131] (2) Synthesis of Intermediate M5-2

[0132] Under nitrogen, add Intermediate M5-1 (0.5 g), triethyl phosphite (4 g), and o-dichlorobenzene (20 mL) to a three-necked flask, heat to reflux for 24 h, cool down, add 20 mL of a 5% sodium carbonate solution by mass concentration, stir for 2 h, separate the layers, and concentrate the organic layer under reduced pressure to dryness. Separate by silica gel column chromatography and elute with petroleum ether to obtain Intermediate M5-2 (0.16 g).

[0133] The obtained Intermediate M5-2 was subjected to mass spectrometry detection, and the measured mass-to-charge ratio (m / z) was: 258.11.

[0134] Synthesis Example 1

[0135] This synthesis example provides Compound P1 and its synthesis method. The synthesis method is as follows:

[0136]

[0137] Under nitrogen protection, dry toluene (120 mL), intermediate M1 (3.3 g), intermediate P1-1 (3.5 g), Pd (dba) were added to a three-necked flask. 2 (bis(dibenzylideneacetonepalladium, 0.0575g), 10% tri-tert-butylphosphine toluene solution (the mass of tri-tert-butylphosphine solution is 0.4g, and the amount of tri-tert-butylphosphine is 0.0002mol) and sodium tert-butoxide (1.44g), heated to 40°C for reaction for 2h, then heated to 60°C for reaction for 2h, then refluxed for 5h, cooled to room temperature, separated by adding water, and then the organic layer was washed with water until neutral, dried with magnesium sulfate, filtered to remove magnesium sulfate, concentrated to dryness, separated by silica gel column chromatography, eluted with a solvent of petroleum ether:tetrahydrofuran = 10:1 (volume ratio), to obtain compound P1 (4.6g).

[0138] The mass spectrometry detection of compound P1: the mass-to-charge ratio (m / z) was measured to be 646.29.

[0139] Synthesis Example 2-8

[0140] The synthesis examples are respectively a compound and a synthesis method thereof. The corresponding compounds refer to the synthesis method of compound P1, and different raw materials are used to react to prepare the following compounds (see Table 2 below for details). The mass spectra of the prepared compounds are measured and the (m / z) values ​​are recorded. See Table 2 below for details.

[0141] Table 2

[0142]

[0143]

[0144] The synthesis of other unlisted compounds can be carried out by referring to the above examples in combination with common knowledge in the art. The specific structures of some compounds used in the following device examples and device comparative examples are as follows:

[0145]

[0146]

[0147]

[0148] Device Example 1

[0149] The device embodiment provides an organic electroluminescent device, and the compound provided by the present invention is selected as a green light host material in the organic electroluminescent device.

[0150] The structure of the organic electroluminescent device is: ITO / H1(40nm) / green light host material(35nm): PGD-1[10%] / ETL-1(25nm) / LiF(0.5nm) / Al(150nm).

[0151] The preparation process of the organic electroluminescent device is as follows:

[0152] The preparation method of the green light organic electroluminescent device is as follows:

[0153] Place the materials in a vacuum chamber, evacuate to 1×10 -5 ~1×10 -6 Pa, and vacuum deposit them onto the cleaned ITO substrate in sequence to prepare the OLED device.

[0154] 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; H1 is a hole transport material, and ETL-1 is an electron transport material.

[0155] The green light host material of the green light organic electroluminescent device provided in this application example is compound P1.

[0156] Device Examples 2-4, Device Comparative Examples 1-2

[0157] Device Examples 2-4 and Device Comparative Examples 1-2 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.

[0158] Performance test:

[0159] The brightness, driving voltage, current efficiency of the prepared organic electroluminescent device were measured, as well as the LT90 of the lifetime test. 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 ). The driving voltage, current efficiency, and LT90 lifetime are all relative values. The test results are shown in Table 3 below.

[0160] Table 3

[0161] Green light host material <![CDATA[Required luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT90 life Device Example 1 P1 1000 0.96 1.03 1.10 Device Example 2 P3 1000 1.06 1.02 1.39 Device Example 3 P13 1000 / 1.02 1.17 Device Example 4 P14 1000 / 1.01 1.19 Device Comparative Example 1 D1 1000 1.01 0.98 1.09 Device Comparative Example 2 D11 1000 1 1 1

[0162] Among them, " / " means no such data.

[0163] Generally, when a specific compound is used as a green light host material, replacing the H atoms in the specific compound with D atoms can improve the device lifetime. However, after the H atoms at different positions of the specific compound are replaced with D atoms, the resulting different compounds will have different performances.

[0164] In the indolocarbazole group of the triazine-based deuterated compound provided by the present invention, the middle benzene ring is affected by the conjugation of the two benzene rings on the left and right, and there are two N atoms connected to the middle benzene ring in the indolocarbazole group, making the electron cloud density of the middle benzene ring larger. If two H atoms are connected to the middle benzene ring, the bond is more likely to break, which affects the device lifetime.

[0165] By designing the structure of the triazine-based deuterated compound of the present invention, only replacing the two hydrogen atoms of the middle benzene ring in the indolocarbazole group with deuterium atoms has the same effect as replacing all the hydrogen atoms in the indolocarbazole group with deuterium atoms. Since increasing the deuteration rate will increase the cost of the material, the triazine-based deuterated compound provided by the present invention uses a lower deuteration rate and achieves the same improvement in lifetime.

[0166] At the same time, in the compound D1 used in the device comparative example, all the H atoms in the indolocarbazole group are replaced by deuterium atoms, which affects the electron cloud distribution on the indolocarbazole group and also has an adverse effect on the film-forming property of the material. As a result, compared with the OLED device prepared using the compound P1 provided by the present invention, the voltage and efficiency of the OLED device prepared using the compound D1 become worse.

[0167] Device Examples 5-14, Device Comparative Examples 3-5

[0168] Device Examples 5-14 and Device Comparative Examples 3-5 each provide an organic electroluminescent device, which is different from Device Example 1 only in that the green light host material is different (see Table 4 below), and the other preparation steps and conditions are the same as those in Device Example 1.

[0169] Performance Test:

[0170] The brightness, driving voltage, current efficiency of the prepared organic electroluminescent device were measured, as well as the lifetime test LT90. Among them, the lifetime test LT90 refers to the time required for the brightness to decrease to 90% of the initial brightness at room temperature (25-27°C) while keeping the current density at the initial brightness unchanged (here it is the current density at 1000 cd / m 2 . The driving voltage, current efficiency, and LT90 lifetime are all relative values. The test results are shown in Table 4 below.

[0171] Table 4

[0172] Green light host material <![CDATA[Required luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT90 life Device Example 5 P2 1000 1.01 1.09 1.09 Device Example 6 P4 1000 0.96 1.06 1.17 Device Example 7 P5 1000 1.00 1.11 1.03 Device Example 8 P6 1000 0.89 1.07 1.15 Device Example 9 P7 1000 0.97 1.28 1.09 Device Example 10 P8 1000 0.81 1.78 1.04 Device Example 11 P9 1000 0.95 1.47 1.12 Device Example 12 P10 1000 0.87 1.02 / Device Example 13 P11 1000 / 1.07 1.47 Device Example 14 P12 1000 / 1.09 1.11 Device Comparative Example 3 D21 1000 1 1 1 Device Comparative Example 4 D22 1000 1.08 1.06 1.03 Device Comparative Example 5 D5 1000 / 0.91 0.96

[0173] Among them, " / " indicates that there is no such data.

[0174] It can be seen from the comparison between Device Example 6 and Device Comparative Example 3 that in the present invention, by designing the structure of the triazine-based deuterated compound, the triazine-based deuterated 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 lifespan.

[0175] Device Examples 15-18, Device Comparative Examples 6-7

[0176] Device Examples 15-18 and Device Comparative Examples 6-7 respectively provide an organic electroluminescent device, which is only different from Device Example 1 in that the green host material is different (see Table 5 below for details), and other preparation steps and conditions are the same as those of Device Example 1.

[0177] Performance test:

[0178] The brightness, driving voltage, current efficiency of the prepared organic electroluminescent device were measured, as well as the LT90 lifespan test. Among them, the LT90 lifespan test refers to the time required for the brightness to decrease to 90% of the initial brightness at room temperature (25-27 °C) while keeping the current density at the initial brightness unchanged (here it is the current density at 1000 cd / m 2 . The driving voltage, current efficiency, and LT90 lifespan are all relative values. The test results are shown in Table 5 below.

[0179] Table 5

[0180] Green light host material <![CDATA[Required luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT90 life Device Example 15 P15 1000 0.98 1.02 1.08 Device Example 16 P16 1000 0.99 1.09 1.02 Device Example 17 P17 1000 0.97 1.06 1.19 Device Example 18 P18 1000 1.14 0.96 1.27 Device Example 19 P19 1000 0.74 0.99 / Device Comparative Example 6 D31 1000 1 1 1 Device Comparative Example 7 D41 1000 1.18 0.93 1.11

[0181] Among them, " / " indicates that there is no such data.

[0182] By comparing Device Examples 15-17 and Device Comparative Example 6, using the triazine-based deuterated compound provided by the present invention as the host material of the light-emitting layer of the OLED device, the prepared OLED device has excellent comprehensive performance.

[0183] By comparing Device Example 18 and Device Comparative Example 7, using the triazine-based deuterated compound provided by the present invention as the host material of the light-emitting layer of the OLED device, the prepared OLED device has excellent comprehensive performance.

[0184] It can be seen from the above that in the present invention, by designing the structure of the triazine-based deuterated compound, the triazine-based deuterated 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 lifespan.

[0185] The applicant declares that the detailed process flow of the present invention is illustrated by the above embodiments, 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, the selection of specific methods, etc. all fall within the protection scope and the disclosure scope of the present invention.

Claims

1. A triazine deuterated compound, characterized in that: The triazine deuterated compound has a structure as shown in the following formula I: Among them, Ar 11 ,Ar 12 ,Ar 13 Each is independently selected from any one of C6-C40 aryl or C6-C30 heteroaryl; Ar is selected from any one of a single bond, C6-C40 arylene or C6-C30 heteroarylene; X1, X2, X3 are each independently selected from N or CH, and at least one of X1, X2, X3 is selected from N; Ar, Ar 11 ,Ar 12 ,Ar 13 The hydrogen atoms in can each be replaced by deuterium atoms independently; The hydrogen atoms in the compound of formula I may each independently be substituted by at least one of -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy; The triazine deuterated compounds do not include the following compounds:

2. The triazine deuterated compound according to claim 1, characterized in that: The C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, benzofluorenyl, dibenzofluorenyl, naphthfluoroenyl, pyrenyl, peryl, spirofluorenyl, triphenylene, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzoindenofluorenyl, dibenzoindenofluorenyl, naphthfluoroenyl, triphenylmethane, triphenylsilyl or benzonaphthofluorenyl; Preferably, the C6-C30 heteroaryl group is selected from any one or a combination of at least two of carbazolyl, dibenzothiophenyl, dibenzofuranyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl and dinaphthothiophenyl; Preferably, the C6-C20 aryl group is selected from any one of phenyl, naphthyl, biphenyl, anthracenyl, phenanthryl, fluorenyl, triphenylene or fluoranthenyl; Preferably, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, octyl and adamantyl; Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy and octyloxy.

3. The triazine deuterated compound according to claim 1 or 2, characterized in that: Ar is selected from any one of a single bond, a phenylene group, a biphenylene group, a naphthylene group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group or a carbazolyl group; The hydrogen atoms in Ar can each independently be replaced by a deuterium atom; Preferably, Ar is selected from a single bond or a phenylene group; Preferably, part of the hydrogen atoms in Ar are replaced by deuterium atoms; Preferably, all hydrogen atoms in Ar are replaced by deuterium atoms.

4. The deuterated triazine compound according to any one of claims 1 to 3, characterized in that: The Ar 11 ,Ar 12 ,Ar 13 Each is independently selected from at least one of phenyl, biphenyl, terphenyl, naphthyl, triphenylene, fluoranthene, anthracene, phenanthryl, 9,9-dimethylfluorenyl, carbazolyl, dibenzothiophenyl or dibenzofuranyl; The Ar 11 ,Ar 12 ,Ar 13 The hydrogen atoms in are each independently replaced by deuterium atoms; Preferably, the Ar 11 Any one selected from phenyl, biphenyl, terphenyl or naphthyl; The Ar 11 The hydrogen atoms in are each independently replaced by deuterium atoms; Preferably, the Ar 12 ,Ar 13 Each is independently selected from any one of phenyl, biphenyl, terphenyl, naphthyl, triphenylene, fluoranthenyl, phenanthryl, anthracenyl, dibenzofuranyl, dibenzothienyl, carbazolyl or 9,9-dimethylfluorenyl, and is more preferably any one of phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl; The Ar 12 ,Ar 13 The hydrogen atoms in are each independently replaced by deuterium atoms; Preferably, the Ar 11 is selected from phenyl, said Ar 12 ,Ar 13 Any one of them is selected from phenyl, and the other is selected from any one of biphenyl, terphenyl, naphthyl, triphenylene, fluoranthene, anthracene, phenanthryl, dibenzofuranyl, dibenzothienyl, carbazolyl or 9,9-dimethylfluorenyl; The Ar 11 ,Ar 12 ,Ar 13 The hydrogen atoms in are each independently replaced by deuterium atoms; Preferably, the Ar 11 is selected from biphenyl, the Ar 12 ,Ar 13 are all selected from phenyl; The Ar 11 ,Ar 12 ,Ar 13 The hydrogen atoms in are each independently replaced by deuterium atoms; Preferably, the Ar 11 is selected from biphenyl, the Ar 12 ,Ar 13 Any one of them is selected from phenyl, and the other one is selected from biphenyl; The Ar 11 ,Ar 12 ,Ar 13 The hydrogen atoms in are each independently replaced by deuterium atoms; Preferably, the Ar 12 ,Ar 13 Any one of which is selected from terphenyl; The Ar 12 ,Ar 13 The hydrogen atoms in the ions are each independently replaced by deuterium atoms.

5. The deuterated triazine compound according to any one of claims 1 to 4, characterized in that: The hydrogen atoms in the compound of formula I can be independently substituted by at least one of -F, -CN, phenyl, naphthyl, methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, propoxy, triphenylmethyl, and triphenylsilyl.

6. The deuterated triazine compound according to any one of claims 1 to 5, characterized in that: The triazine deuterated compound has any one of the structures shown in the following formulas I-1 to I-4: Among them, Ar 11 ,Ar 12 ,Ar 13 , X1, X2, X3 have the same definitions as in claim 1; Ar, Ar 11 ,Ar 12 ,Ar 13 The hydrogen atoms in can each be replaced by deuterium atoms independently; The hydrogen atoms in the compounds of formulas I-1 to I-4 may each independently be substituted by at least one of -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy.

7. The deuterated triazine compound according to any one of claims 1 to 6, characterized in that: The triazine deuterated compound is selected from any one of the following substituted or unsubstituted compounds: The substitution refers to the above triazine deuterated compounds, Ar, Ar 11 ,Ar 12 ,Ar 13 The hydrogen atoms at the corresponding positions of the groups can each independently be replaced by a deuterium atom.

8. An intermediate, characterized in that The intermediate has a structure shown in the following formula MA: Among them, Ar 11 has the same definition as in claim 1; The hydrogen atoms in the intermediate can each independently be substituted by at least one of -F, -CN, C6-C20 aryl, triphenylmethyl, triphenylsilyl, C1-C12 alkyl or C1-C12 alkoxy; The intermediates do not include the following compounds: The intermediate is used to prepare the triazine deuterated compound as described in any one of claims 1 to 7.

9. 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 includes the triazine deuterated compound as described in any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 9, characterized in that: The organic thin film layer includes a light-emitting layer; The main material of the light-emitting layer comprises the triazine deuterated compound according to any one of claims 1 to 7; Preferably, the organic electroluminescent device is a green organic electroluminescent device; Preferably, the light-emitting layer comprises a phosphorescent light-emitting layer, and the phosphorescent light-emitting layer comprises a green phosphorescent light-emitting layer, a red phosphorescent light-emitting layer, and a blue phosphorescent light-emitting layer.

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