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, so that the triazine deuterated compound is suitable for being used as a main body material of a phosphorescent light-emitting layer of the organic electroluminescent device, and the organic electroluminescent device has relatively high current efficiency, relatively long service life and relatively low driving voltage.

Description

Technical Field

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

[0002] The structure of an organic electroluminescent device is specifically: an anode, a cathode, and an organic layer therebetween. To improve the efficiency and stability of the organic electroluminescent element, the organic material layer includes multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer, a light - emitting layer, an electron transport layer (ETL), and an electron injection layer (EIL). Currently, organic electroluminescence has become a mainstream display technology. Correspondingly, various new OLED materials have been developed. Electron transport materials and hole injection materials, hole transport materials, or hole blocking layers are major obstacles to the full practical application of OLED technology, which directly limit the luminous efficiency, service life, and operating voltage of the device.

[0003] To meet the higher requirements of people for OLED devices, it is urgent to develop more types of materials in this field to improve the performance of OLED devices in terms of current efficiency, lifespan, etc. Summary of the Invention

[0004] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide a triazine - type deuterated compound, an intermediate, and an organic electroluminescent device. In the present invention, by designing the structure of the triazine - type deuterated compound, it is suitable as the host material of the phosphorescent light - emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has a higher current efficiency, a longer lifespan, and a lower driving voltage.

[0005] To achieve this purpose, the present invention adopts the following technical solutions:

[0006] In the first aspect, the present invention provides a triazine - type deuterated compound, and the triazine - type deuterated compound has a structure shown in the following formula I:

[0007]

[0008] Wherein, n is selected from 0 or 1;

[0009] At least one hydrogen atom in the compound of formula I is replaced by a deuterium atom.

[0010] In the present invention, by designing the structure of the triazine - type deuterated compound, it is suitable as the host material of the phosphorescent light - emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has a higher current efficiency, a longer lifespan, and a lower driving voltage.

[0011] It should be noted that in the present invention, unless otherwise specified, D refers to a deuterium atom, and H and hydrogen both refer to protium. The same applies hereinafter.

[0012] 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.

[0013] As a preferred technical solution of the present invention, the compound of formula I has the structure shown in formula I-1 as follows:

[0014]

[0015] Among them, in the compound of formula I-1, m is selected from integers between 0 and 7, for example, it can be 0, 1, 2, 3, 4, 5, 6 or 7; n is selected from 0 or 1.

[0016] As a preferred technical solution of the present invention, in the compound of formula I-1, m is selected from 0.

[0017] As a preferred technical solution of the present invention, in the compound of formula I-1, m is selected from 7.

[0018] As a preferred technical solution of the present invention, the compound of formula I has the structure shown in formula I-2 as follows:

[0019]

[0020] Among them, in the compound of formula I-2, m is selected from integers between 1 and 7, for example, it can be 1, 2, 3, 4, 5, 6 or 7; n is selected from 0 or 1.

[0021] As a preferred technical solution of the present invention, in the compound of formula I-2, m is selected from 0.

[0022] As a preferred technical solution of the present invention, in the compound of formula I-2, m is selected from 7.

[0023] As a preferred technical solution of the present invention, in the compound of formula I, n is selected from 0.

[0024] As a preferred technical solution of the present invention, the triazine deuterated compound is selected from any one of the following compounds:

[0025]

[0026]

[0027] Preferably, the triazine deuterated compound is selected from any one of the following compounds:

[0028]

[0029]

[0030] It should be noted that the present invention has no special restrictions on the synthesis method of the above-mentioned triazine deuterated compounds, and the commonly used synthesis methods in the art are applicable.

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

[0032]

[0033] The intermediate is used for preparing the triazine deuterated compound as described in the first aspect.

[0034] In a second aspect, the present invention provides an organic electroluminescent device, and the organic electroluminescent device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;

[0035] The material of the organic thin film layer includes the triazine deuterated compound as described in the first aspect.

[0036] As a preferred technical solution of the present invention, the organic thin film layer includes a light-emitting layer, and the host material of the light-emitting layer includes the triazine deuterated compound as described in the first aspect.

[0037] Preferably, the light-emitting layer is a phosphorescent light-emitting layer.

[0038] As a preferred technical solution of the present invention, the organic electroluminescent device is a red organic electroluminescent device.

[0039] In the present invention, the light-emitting layer includes a light-emitting layer host material and a doping material, and the doping material is also called a dye or a phosphorescent light-emitting material. The light-emitting layer host material can be a single compound or a mixture formed by two or more compounds.

[0040] 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 yellow phosphorescent light-emitting layer.

[0041] 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%.

[0042] In the present invention, the doping material of the light-emitting layer can be selected from phosphorescent materials, which are also known as triplet light-emitting materials and refer to the light emitted by substances 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 all applicable. Exemplarily, but not limited to, compounds having the structure shown by the following formula PD:

[0043]

[0044] Among them, M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu or Au;

[0045] Y 1 -Y 4 Each independently is selected from carbon or nitrogen;

[0046] 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;

[0047] Cy 1 and Cy 2 Each independently is 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, benzimidazolazolyl, benzazolyl, triazolyl, tetrazolyl, dioxazolyl, triazinyl, dibenzothienyl, N-heterocarbazolyl, and Cy 1 and Cy 2 can optionally be connected to each other via a single bond or an organic linking group;

[0048] Between any two ligands of M, between two or more 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 conforming to chemical principles;

[0049] 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, a substituted or unsubstituted C1-C60 (such as C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkyl, a substituted or unsubstituted C2-C60 (such as C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkenyl, a substituted or unsubstituted C2-C60 (such as C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkynyl, a substituted or unsubstituted C1-C60 (such as C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkoxy, a substituted or unsubstituted C2-C10 (such as C2, C3, C4, C5, C6, C7, C8, C9 or C10) heterocycloalkyl, a substituted or unsubstituted C6-C60 (such as C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) aryl, a substituted or unsubstituted C6-C60 (such as C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) aryloxy, a substituted or unsubstituted C6-C60 (such as C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.) arylthio, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0050] a 1 and a 2 Each independently is an integer selected from 1 to 5, such as 1, 2, 3, 4 or 5;

[0051] b is selected from integers from 0 to 4, such as 0, 1, 2, 3 or 4;

[0052] a is selected from 1, 2 or 3;

[0053] L 1 is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

[0054] Preferably, the PD compound of the formula is any one of the following compounds:

[0055]

[0056]

[0057]

[0058]

[0059] In the present invention, the organic thin film layer includes a hole layer, and the hole layer includes a hole injection layer, a hole transport layer, and an electron blocking layer.

[0060] The hole injection layer material includes a P-type dopant. The P-type dopant refers to a substance that coexists with the hole injection layer material in the OLED device and can oxidize the hole injection layer material, thereby acting as an electron acceptor and promoting the movement of holes in the hole injection layer toward the anode. In the present invention, the difference between the absolute value of the LUMO of the P-type dopant and the absolute value of the HOMO of the hole layer material is greater than -0.2 V, preferably greater than -0.1 eV, more preferably greater than 0 eV, more preferably greater than 0.1 eV, and further preferably greater than 0.2 eV.

[0061] The P-type dopant exists in the hole injection layer in a volume percentage of 1% to 10% (for example, it can be 1%, 2%, 4%, 6%, 8%, or 10%, etc.). In the present invention, no special limitation is imposed on the type of the P-type dopant. Exemplarily, the compounds shown as D-1 to D-13 disclosed in CN113728453A or the compounds shown as HI-1 to HI-9 described below can be selected:

[0062]

[0063] In the present invention, the hole layer material (including the hole injection layer, the hole transport layer, and the electron blocking layer) has the structure shown by the following formula HT-GH4:

[0064]

[0065] Among them, L 41 is selected from a single bond, an aryl group of C6-C40 (for example, it can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.), and a heteroaryl group of C6-C20 (for example, it can be C6, C8, C10, C12, C16, or C20, etc.);

[0066] Ar 41 and Ar 42 are each independently selected from an aryl group of C6-C40 (for example, it can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) and a heteroaryl group of C6-C20 (for example, it can be C6, C8, C10, C12, C16, or C20, etc.);

[0067] X is selected from CR 41 R 42or NR 43 , wherein R 41 、R 42 、R 43 are each independently selected from a substituted or unsubstituted phenyl group (the substituents of the substituted phenyl group are selected from C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) alkyl, C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) alkoxy), naphthyl, triphenylene, fluoranthenyl, 9,9-dimethylfluorenyl, biphenyl, a substituted or unsubstituted group (the substituent of the substituted group is phenyl), a substituted or unsubstituted dibenzothiophenyl group (the substituent of the substituted group is phenyl), a substituted thiophenyl group, and any one of C1-C6 (e.g., C1, C2, C3, C4, C5 or C6) alkyl, and R 41 、R 42 can be connected into a ring through a single bond.

[0068] The compound of formula HT-GH4 is selected from any one of the following compounds:

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] In the present invention, the hole layer material (including the hole injection layer, the hole transport layer and the electron blocking layer) further includes a compound having a structure shown in formula IA below or a compound having a structure shown in formula IB:

[0076]

[0077] wherein, L is selected from any one of C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) arylene, dibenzofuranyl or dibenzothiophenyl;

[0078] m is an integer between 0 and 4 (e.g., 0, 1, 2, 3 or 4), and n is selected from 0 or 1;

[0079] Ar is selected from any one of triphenylene, fluoranthene, dibenzofuranyl or dibenzothiophenyl;

[0080] Ar 1 and Ar 2 are each independently selected from any one of aryl groups containing C6-C40 (such as C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.), dibenzofuran or dibenzothiophene groups;

[0081] Ar 1 between Ar and Ar, 2 between Ar and Ar, and 1 Ar, 2 between them can each independently be connected or bridged by a single bond, O, S, CR 1 R 2 or NR.

[0082] R, R 1 R 2 are each independently selected from any one of C1-C20 (such as C1, C2, C4, C6, C8, C10, C12, C14, C16, C18 or C20, etc.) alkyl groups, C6-C40 (such as C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl groups, dibenzofuran groups or dibenzothiophene groups;

[0083] The H in the compound of formula IB and the compound of formula IA can each independently be replaced by at least one of -F, -CN, -D (deuterium atom), C1-C6 alkyl group, C1-C6 alkoxy group, phenyl group, biphenyl group, naphthyl group, phenanthryl group, anthryl group, fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, triphenylene group, fluoranthenyl group, pyrenyl group, perylenyl group, spirofluorene group, indenofluorenyl group or hydrogenated benzanthracenyl group.

[0084] Preferably, the Ar is a fluoranthenylene group, and m + n > 1.

[0085] Preferably, the H in the compound of formula IB and the compound of formula IA can be replaced by at least one of -F, -CN, -D, C1-C3 alkyl group (such as methyl, ethyl or propyl), C1-C3 alkoxy group (such as methoxy, ethoxy or propoxy), phenyl group, biphenyl group, triphenylene group, fluoranthenyl group.

[0086] Preferably, the L, Ar 1 Ar 2 are each independently selected from at least one of phenyl group, biphenyl group, naphthyl group, phenanthryl group, anthryl group, fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, triphenylene group, fluoranthenyl group, pyrenyl group, perylenyl group, spirofluorene group, indenofluorenyl group or hydrogenated benzanthracenyl group.

[0087] Preferably, the compound of formula IB is selected from the following structures:

[0088]

[0089] Among them, L is a phenylene group;

[0090] Ar 1 and Ar 2 and m have the same scope of protection as described above.

[0091] Preferably, the compound of Formula IB is selected from any one of the following compounds:

[0092]

[0093]

[0094]

[0095] In the OLED device provided by the present invention, in addition to the compounds of Formula HT-GH4, the compounds of Formula IB, and the compounds of Formula IA, the hole transport layer material may also include conventional hole materials in the art without particular limitation. Exemplarily, but not limited to, triarylamine compounds or carbazole compounds. Preferably, triarylamine compounds or carbazole compounds containing more than 3 N atoms are used because the HOMO of triarylamine compounds or carbazole compounds containing more than 3 N atoms is higher (with a smaller absolute value), and they are more suitable as hole injection layer materials. Triarylamine compounds or carbazole compounds containing 2 or 1 N atom can be used as hole transport layer materials. Some compounds containing 1 N atom or carbazole compounds, if they have a relatively high LUMO, can also be used as electron blocking layer materials.

[0096] As the hole transport layer material, the triarylamine compound or carbazole compound has the following structure:

[0097]

[0098] Among them, Ar 601 to Ar 609 each independently selected from substituted or unsubstituted C6-C40 (such as C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted naphthobenzofuranyl groups, substituted or unsubstituted naphthobenzothiophenyl groups, substituted or unsubstituted dinaphthofuranyl groups, substituted or unsubstituted dinaphthothiophenyl groups;

[0099] And Ar 601 to Ar 609Ar adjacent to or linked to the same N atom 601 ~Ar 609 can be linked by a single bond or bridged by O, S, CR 701 R 702 、NR 703 ;

[0100] R 701 、R 702 、R 703 are selected from C6-C40 (such as C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40 etc.) aryl groups, C6-C20 (such as C6, C8, C10, C12, C16 or C20 etc.) heteroaryl groups, C1-C6 (such as C1, C2, C3, C4, C5 or C6) alkyl groups, and R 701 、R 702 can be linked by a single bond.

[0101] The hole blocking layer (HBL) can confine holes and / or excitons within the light-emitting layer to improve the current efficiency and lifetime of the device. Compared with the light-emitting layer material closest to the HBL interface, the HBL material has a lower HOMO (larger absolute value) and / or a higher triplet energy.

[0102] The electron transport layer (ETL) can include materials capable of transporting electrons. The electron transport layer can be intrinsic (undoped) or doped, and doping can be used to enhance conductivity. In the present invention, there is no special limitation on the ETL material, and any metal complex or organic compound can be used as long as it can transport electrons. Generally, the electron transport layer material contains at least one of the following structural fragments: pyridine structure, pyrimidine structure, triazine structure, benzimidazole structure, benzoxazole structure, benzothiazole structure, naphthyridine structure, phenanthridine structure, carbazole structure, dibenzothiophene structure.

[0103] In the present invention, there is no any special limitation on the electron transport layer material, and exemplary ones include but are not limited to:

[0104]

[0105]

[0106]

[0107] In the present invention, the material of the cathode is a metal with a low work function (such as alkaline earth metals, alkali metals, main group metals or lanthanide elements (such as Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.)), a metal alloy composed of multiple metals (an alloy composed of an alkali metal or an alkaline earth metal and silver, such as an alloy composed of magnesium and silver), or a multilayer structure. If the cathode material is a multilayer structure, in addition to the metals mentioned above, other metals with a relatively high work function, such as Ag or Al, can also be used. In this case, a combination of the metals is usually used, such as Ca / Ag, Mg / Ag or Ba / Ag.

[0108] It is also possible to select a thin intermediate layer of a material with a high dielectric constant to be introduced between the metal cathode and the organic semiconductor to form a multilayer structure; the material with a high dielectric constant can also be called an electron injection material, and fluorides of alkali metals or alkaline earth metals, as well as corresponding oxides or carbonates (such as LiF, Li 2 O, BaF 2 , MgO, NaF, CsF, Cs 2 CO 3 etc.) or lithium quinolate (LiQ) can be selected.

[0109] Compared with the prior art, the present invention has the following beneficial effects:

[0110] In the present invention, by designing the structure of the triazine-based deuterated compound, it is applicable as the host material of the phosphorescent emission layer of the organic electroluminescent device, so that the organic electroluminescent device has a high current efficiency, a long lifespan and a low driving voltage. Specific Embodiments

[0111] To facilitate the understanding of the present invention, the following examples are listed. 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.

[0112] Preparation Example 1 Synthesis of Intermediate PD2-1

[0113] This preparation example provides intermediate PD2-1 and its synthesis method, and the synthesis method is as follows:

[0114]

[0115] Under nitrogen protection, 4.1 g of compound MD2-1 and 110 mL of tetrahydrofuran were added to a three-necked flask, and then the temperature was lowered to -78 °C. A 1.6 M n-hexane solution of 0.01 mol of butyllithium (6.3 mL) was slowly added, and then it was maintained at -78 °C to -60 °C for 30 min. A tetrahydrofuran solution of 2.2 g of compound MD2-2 and 0.0001 mol of Pd(dba) 2, 0.0001 mol of anhydrous nickel chloride was slowly heated to room temperature and reacted for 4 hours, then heated to reflux and reacted for 2 h. After cooling, water and dichloromethane were added and separated by liquid separation. The organic layer was washed with water until neutral, dried over anhydrous magnesium sulfate, the desiccant was filtered off, concentrated to dryness, and separated by silica gel column chromatography. Elution with petroleum ether:dichloromethane = 10:3 (volume ratio) gave intermediate PD2-1 (2.9 g).

[0116] The obtained intermediate PD2-1 was subjected to mass spectrometry detection, and the m / z was 521.13.

[0117] Synthesis of intermediate PD3-1 in Preparation Example 2

[0118] This preparation example provides intermediate PD3-1 and its synthesis method, and the synthesis method is as follows:

[0119]

[0120] Referring to the synthesis method of intermediate PD2-1, intermediate PD3-1 was prepared.

[0121] The obtained intermediate PD3-1 was subjected to mass spectrometry detection, and the m / z was 647.18.

[0122] Synthesis of compound P1 in Synthesis Example 1

[0123] This synthesis example provides compound P1 and its synthesis method, and the synthesis method is as follows:

[0124]

[0125] Under nitrogen protection, 2.9 g of intermediate P1-1 and 60 mL of tetrahydrofuran were added to a three-necked flask, then cooled to -78 °C, and 0.01 mol of a n-hexane solution of butyllithium (concentration 1.6 M, 6.3 mL) was slowly added. Then, it was maintained at -78 °C to -60 °C for 30 min, and a tetrahydrofuran solution of 5.2 g of compound MA and 0.0001 mol of Pd(dba) 2 , 0.0001 mol of anhydrous nickel chloride were added. It was slowly heated to room temperature and reacted for 2 hours, then heated to reflux and reacted for 4 h. After cooling, water and dichloromethane were added and separated by liquid separation. The organic layer was washed with water until neutral, dried over anhydrous magnesium sulfate, the desiccant was filtered off, concentrated to dryness, and separated by silica gel column chromatography. Elution with petroleum ether:dichloromethane:tetrahydrofuran = 10:2:1.5 (volume ratio) gave compound P1 (5.6 g).

[0126] The obtained compound P1 was subjected to mass spectrometry detection, and the m / z was 693.27.

[0127] Synthesis Examples 2 - 9

[0128] Synthesis Example 2-9 respectively provide a compound. Referring to the synthesis method of compound P1, using Raw Material 1 and Raw Material 2 to react, the corresponding compound was synthesized and its mass spectrometry was detected. The mass-to-charge ratio (m / z) is shown in Table 1 below.

[0129] Table 1

[0130]

[0131]

[0132]

[0133] Among them, the synthesis method of compound P4-1 is as follows:

[0134]

[0135] Under nitrogen protection, add 30 mL of toluene, 15 mL of ethanol, and 10 mL of water to a three-necked flask, then add 2.3 g of deuterated m-dibromobenzene, 1.7 g of 2-naphthaleneboronic acid, 2.12 g of sodium carbonate, and 0.23 g of tetrakis(triphenylphosphine)palladium. Slowly heat up to 60 °C and react for 2 h, then heat up to reflux and react for 5 h. Cool down to room temperature, add water for liquid separation. After washing the organic layer with water, dry it with magnesium sulfate. After removing the desiccant, concentrate to dryness and separate by silica gel column chromatography, eluting with petroleum ether to obtain compound P4-1 (2.2 g).

[0136] Perform mass spectrometry detection on the obtained intermediate P4-1, and the measured mass-to-charge ratio (m / z) is: 286.03.

[0137] For other compounds whose specific synthesis methods are not listed, the synthesis can be carried out by referring to the above examples and combining the common general knowledge in the art.

[0138] The specific structures of some compounds used in the following application examples and comparative application examples of the present invention are as follows:

[0139]

[0140]

[0141]

[0142] Among them, the synthesis method of compound D2 is as follows:

[0143]

[0144] (1) Synthesis of intermediate D2-1

[0145] With reference to the synthesis of intermediate PD2-1, intermediate D2-1 was prepared. The obtained intermediate D2-1 was subjected to mass spectrometry detection, and the m / z was 521.13.

[0146] (2) Synthesis of compound D2

[0147] With reference to the synthesis of compound P1, compound D2 was prepared.

[0148] The obtained compound D2 was subjected to mass spectrometry detection, and the m / z was 693.27. Synthesis method of compound D3:

[0149]

[0150] With reference to the synthesis of compound P1, compound D3 was prepared.

[0151] The obtained compound D3 was subjected to mass spectrometry detection, and the m / z was 765.28.

[0152] Synthesis method of compound D4:

[0153]

[0154] With reference to the synthesis of compound P1, compound D4 was prepared.

[0155] The obtained compound D4 was subjected to mass spectrometry detection, and the m / z was 765.28.

[0156] Application Example 1

[0157] This application example provides a red phosphorescent organic light-emitting device, using the compound provided by the present invention as the host material of the light-emitting layer. The structure of the red phosphorescent organic light-emitting device is:

[0158] ITO / HT-1: HI-2 [5%] (80 nm) / HT-1 (30 nm) / EB-1 (20 nm) / Host material: PRD-1 [8%] (35 nm) / ETL-1 (25 nm) / LiF (0.5 nm) / Al (150 nm).

[0159] The preparation method of the red phosphorescent organic light-emitting device is as follows:

[0160] 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.

[0161] Among them, PRD-1 [8%] refers to the doping ratio of the dye, that is, the volume ratio of the host material to the dye PRD-1 is 92:8; HT-1:HI-2 [5%] refers to the ratio of the P-type dopant, that is, the volume ratio of the hole material HT-1 and the P-type dopant HI-2 is 95:5. HT-1 is a hole transport material; HT-1:HI-2 [5%] is used as a hole injection layer, and EB-1 is an electron blocking layer.

[0162] The host material of the light-emitting layer of the red phosphorescent organic light-emitting device provided in this application example is compound P1.

[0163] Application Example 2-4

[0164] Application Examples 2-4 respectively provide a red phosphorescent organic light-emitting device, which is only different from Application Example 1 in that the host material of the light-emitting layer is replaced by other compounds (see Table 2 for details), and other preparation steps and conditions are the same as those in Application Example 1.

[0165] Comparative Application Examples 1-2

[0166] Comparative Application Examples 1-2 respectively provide a red phosphorescent organic light-emitting device, which is only different from Application Example 1 in that the host material of the light-emitting layer is different (see Table 2 for details), and other preparation steps and conditions are the same as those in Application Example 1.

[0167] Performance Test

[0168] Test the brightness, driving voltage, current efficiency and LT95 of the organic light-emitting devices provided above. Among them, the voltage and current efficiency are the corresponding values when the brightness is 1000 cd / m 2 The corresponding value, LT95 refers to the time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density while keeping the initial current density of the device at 10 mA / cm 2 unchanged. Among them, the driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 2:

[0169] Table 2

[0170] Host material <![CDATA[Luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT95 Application Example 1 P1 1000 0.98 1.02 1.19 Application Example 2 P2 1000 0.98 1.03 1.21 Application Example 3 PD1 1000 1 0.99 1.03 Application Example 4 PD2 1000 0.99 1.06 1.13 Comparative Application Example 1 D1 1000 1 1 1 Comparative Application Example 2 D2 1000 1.02 0.92 0.76

[0171] In compound D1, the triazine ring is replaced by three different substituents, one phenyl group, one naphthylphenyl group, and one spirofluoreneoxanthene group. Among these three groups, the naphthylphenyl group has the strongest electron-donating ability. The inventors found that when all or part of the naphthylphenyl group is deuterated, the film-forming property of the material is slightly improved, making the charge transfer ability of the material stronger, the device voltage lower. At the same time, after the film-forming property of the material is improved, the energy of the material can be better transferred to the dye, and the device efficiency increases. And after this part is deuterated, the device life increases significantly, which can be seen from Application Example 1 and Application Example 2.

[0172] In addition, for the compound P1 in Application Example 1, in the naphthylphenyl group, the phenylene group close to the triazine ring is deuterated, and its lifetime is increased by 19% compared with Comparative Application Example 1. For the compound P2 in Application Example 2, the entire naphthylphenyl group is deuterated, and its lifetime is increased by 21% compared with Comparative Application Example 1, indicating that the deuteration of the added naphthalene ring does not significantly increase the device lifetime.

[0173] In addition, for the compound PD2 in Application Example 4, in the naphthylphenyl group, the naphthyl group is deuterated, and while the device lifetime increases, its efficiency increases significantly.

[0174] In addition, for the compound PD1 in Application Example 3, the phenyl substituent on the triazine is deuterated, and its voltage, efficiency, and lifetime are slightly improved, but not as good as the device performance prepared with a partially deuterated or fully deuterated structure of the naphthylphenyl group.

[0175] Application Examples 5 - 6, Comparative Application Example 3

[0176] Application Examples 5 - 6 and Comparative Application Example 3 respectively provide a red phosphorescent organic light-emitting device, which is only different from Application Example 1 in that the host material of the light-emitting layer is different (see Table 3 in detail), and other preparation steps and conditions are the same as those in Application Example 1.

[0177] Performance Test

[0178] Test the brightness, driving voltage, current efficiency, and LT95 of the above-provided organic light-emitting devices. Among them, the voltage and current efficiency are the corresponding values when the brightness is 1000 cd / m 2 , and LT95 refers to the time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density while keeping the initial current density of the device at 10 mA / cm 2 unchanged. Among them, the driving voltage, current efficiency, and LT95 are relative values. The specific test results are shown in Table 3:

[0179] Table 3

[0180] Host material <![CDATA[Luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT95 Application Example 5 P3 1000 0.97 1.03 1.19 Application Example 6 P4 1000 1.03 1.02 1.20 Comparative Application Example 3 D5 1000 1 1 1

[0181] As can be seen from the above content, in the present invention, by designing the structure of the triazine-based deuterated compound, it is suitable to be used as the host material of the phosphorescent light-emitting layer of the organic light-emitting device, so that the organic light-emitting device has a high current efficiency, a long lifetime, and a low driving voltage.

[0182] Application Examples 7 - 8, Comparative Application Example 4

[0183] Application Examples 7 - 8 and Comparative Application Example 4 respectively provide a red phosphorescent organic light-emitting device, which is only different from Application Example 1 in that the host material of the light-emitting layer is different (see Table 4 in detail), and other preparation steps and conditions are the same as those in Application Example 1.

[0184] Performance test

[0185] Test the brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above. Among them, the voltage and current efficiency are the corresponding values when the brightness is 1000 cd / m 2 LT95 refers to the time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density while keeping the initial current density of the device at 10 mA / cm 2 unchanged. The driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 4 as follows:

[0186] Table 4

[0187] Host material <![CDATA[Luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT95 Application Example 7 P5 1000 0.98 1.01 1.29 Application Example 8 PD3 1000 1.01 1.01 1.06 Comparative Application Example 4 D3 1000 1 1 1

[0188] From the comparison between Application Example 7 and Application Example 8, it can be seen that the deuteration rate of P5 in Application Example 7 is lower than that of PD3 in Application Example 8, but its performance is better.

[0189] As can be seen from the above, in the present invention, by designing the structure of the triazine-based deuterated compound, it is applicable as the host material of the phosphorescent light-emitting layer of the organic electroluminescent device, so that the organic electroluminescent device has high current efficiency, long lifetime and low driving voltage.

[0190] Application Example 9, Comparative Application Example 5

[0191] Application Example 9 and Comparative Application Example 5 respectively provide a red phosphorescent organic electroluminescent device, which is different from Application Example 1 only in that the host material of the light-emitting layer is different (see Table 5 for details), and other preparation steps and conditions are the same as those in Application Example 1.

[0192] Performance test

[0193] Test the brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above. Among them, the voltage and current efficiency are the corresponding values when the brightness is 1000 cd / m 2 LT95 refers to the time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density while keeping the initial current density of the device at 10 mA / cm 2 unchanged. The driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 5 as follows:

[0194] Table 5

[0195] Host material <![CDATA[Luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT95 Application Example 9 P6 1000 0.99 1.03 1.09 Comparative Application Example 5 D4 1000 1 1 1

[0196] In summary, in the present invention, by designing the structure of the triazine-based deuterated compound, it is applicable as the host material of the phosphorescent emitting layer of the organic electroluminescent device, enabling the organic electroluminescent device to have high current efficiency, long lifespan, and low driving voltage.

[0197] 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 replacement 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: Wherein, n is selected from 0 or 1; In the compounds of formula I at least one hydrogen atom is replaced by a deuterium atom.

2. The triazine deuterated compound according to claim 1, characterized in that: The compound of formula I has the structure shown in the following formula I-1: Wherein, in the compound of formula I-1, m is selected from an integer between 0 and 7; n is selected from 0 or 1.

3. The triazine deuterated compound according to claim 2, characterized in that: In the compound of formula I-1, m is selected from 0; Preferably, in the compound of formula I-1, m is selected from 7.

4. The triazine deuterated compound according to claim 1, characterized in that: The compound of formula I has the structure shown in the following formula I-2: Wherein, in the compound of formula I-2, m is selected from an integer between 1 and 7; n is selected from 0 or 1.

5. The triazine deuterated compound according to claim 4, characterized in that: In the compound of formula I-2, m is selected from 0; Preferably, in the compound of formula I-2, m is selected from 7.

6. The deuterated triazine compound according to any one of claims 1 to 5, characterized in that: In the compound of formula I, n is selected from 0.

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 compounds:

8. An intermediate, characterized in that The intermediates 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 organic thin film layer material comprises the triazine deuterated compound as described in any one of claims 1 to 7; Preferably, the organic thin film layer comprises a light-emitting layer, and a main material of the light-emitting layer comprises the triazine deuterated compound according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 9, characterized in that: The light-emitting layer is a phosphorescent light-emitting layer; preferably, the organic electroluminescent device is a red light organic electroluminescent device.

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