A triazine compound, a composition containing the same, and an organic electroluminescent device

Abstract

The application provides a triazine compound, a composition containing the same and an organic electroluminescent device. The compound has a structure shown in formula I or formula II; the composition comprises a first component and a second component; the first component comprises a compound having a structure shown in formula I or formula II; and the second component comprises a compound having a structure shown in formula III. In the application, the structure of the compound is designed to be suitable for use as a host material of a phosphorescent light-emitting layer of an organic electroluminescent device, so that the organic electroluminescent device has higher current efficiency and longer service life.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials technology, specifically relating to a triazine compound, a composition containing the triazine compound, and an organic electroluminescent device. Background Technology

[0002] The structure of an organic light-emitting diode (OLED) device specifically consists of an anode, a cathode, and an organic layer between them. To improve the efficiency and stability of OLED devices, the organic material layer comprises multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a hole blocking layer, an emissive layer, an electron transport layer (ETL), and an electron injection layer (EIL). Currently, organic light emission has become a mainstream display technology, and correspondingly, various novel OLED materials have been developed.

[0003] To meet the higher demands of people for OLED devices, there is an urgent need in the field to develop more types of materials to improve the performance of OLED devices in terms of current efficiency, lifetime, and other aspects. Summary of the Invention

[0004] To address the shortcomings of existing technologies, the present invention aims to provide a triazine compound, a composition comprising the triazine compound, and an organic electroluminescent device. In this invention, the structure of the triazine compound is designed to be suitable as the main material for the phosphorescent layer of an organic electroluminescent device, thereby enabling the organic electroluminescent device to exhibit high current efficiency and long lifespan.

[0005] To achieve this objective, the present invention adopts the following technical solution:

[0006] In a first aspect, the present invention provides a triazine compound having the structure shown in Formula I or Formula II:

[0007]

[0008] Ar1 is selected from C6-C40 arylene or C6-C30 heteroarylene;

[0009] Ar2 is selected from C6-C40 aryl or C6-C30 heteroaryl;

[0010] X is selected from O or S; Y is selected from C or Si;

[0011] R1 and R2 are each independently selected from C6-C20 aryl or C1-C12 alkyl, and R1 and R2 can be linked together to form a ring by a single bond;

[0012] When n is 0 or 1, and when n is 0, Ar2 is not a phenyl group;

[0013] In the compounds shown in Formula I and Formula II, the hydrogen atoms can be independently replaced by -D (deuterium), -F, -CN, C6-C20 aryl or C1-C12 alkyl groups.

[0014] In this invention, the structure of triazine compounds is designed to be suitable as the main material for the phosphorescent light-emitting layer of organic electroluminescent devices, thereby enabling the organic electroluminescent devices to have high current efficiency and long lifespan.

[0015] In this invention, C6-C40 can be C6, C10, C12, C15, C18, C24, C30, C36 or C40, etc.

[0016] C6-C30 can be C6, C10, C12, C15, C18, C24, or C30, etc.

[0017] C6-C20 can be C6, C10, C12, C15, C18, or C20, etc.

[0018] C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, or C12, etc.

[0019] It should be noted that in this invention, "D" represents a deuterium atom, and the same applies below.

[0020] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. The purpose and beneficial effects of the present invention can be better achieved and realized through the following preferred technical solutions.

[0021] As a preferred embodiment of the present invention, the C6-C40 arylene is selected from any one of phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, naphthylene, pyrene, perylene, spirofluorene, phenylenetriene, fluorenylene, hydrogenated benzo[a]anthrayl, ind[a]fluorene, benzo[a]ind[a]fluorene, dibenzo[a]ind[a]fluorene, naphthylene, or benzo[a]naphthylene.

[0022] Preferably, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzofuranyl, dibenzothiophene, naphthobenzofuranyl, naphthobenzothiophene, dinaphthofuranyl, or dinaphthothiophene.

[0023] Preferably, Ar1 is selected from any one of phenylene, naphthylene, biphenylene, carbazolyl, dibenzofuranylene, dibenzothiopheneylene, or fluoreneylene.

[0024] As a preferred embodiment of the present invention, the C6-C40 aryl group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, naphthyl, pyrene, perylene, spirofluorenyl, triphenylene, fluoranyl, hydrogenated benzo[a]anthrayl, ind[a]fluorenyl, benzo[a]ind[a]fluorenyl, dibenzo[a]ind[a]fluorenyl, naphthyl, or benzo[a]naphthyl.

[0025] Preferably, the C6-C30 heteroaryl group is selected from any one of carbazolyl, dibenzofuranyl, dibenzothiophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, dinaphthofuranyl, or dinaphthothiophenyl.

[0026] Preferably, the Ar2 is selected from any one of phenyl, naphthyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiophene, or fluorenyl.

[0027] In a preferred embodiment of the present invention, n is 0.

[0028] Preferably, the hydrogen atoms in the compounds of Formula I and Formula II can each be independently substituted by at least one of -D, -F, -CN, phenyl, naphthyl, biphenyl, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, or butoxy.

[0029] As a preferred embodiment of the present invention, the triazine compound is selected from any one of the following substituted or unsubstituted triazine compounds:

[0030]

[0031]

[0032]

[0033] The substitution refers to the fact that each hydrogen atom in the above triazine compounds can be independently replaced by a deuterium atom.

[0034] It should be noted that the present invention does not impose any special restrictions on the preparation method of the above-mentioned triazine compounds, and conventional preparation methods in the art can be used to prepare them.

[0035] Preferably, the triazine compound is selected from any one of the following compounds:

[0036]

[0037] In a second aspect, the present invention provides an intermediate comprising the following compounds:

[0038]

[0039] The intermediate is used to prepare triazine compounds as described in the first aspect.

[0040] Thirdly, the present invention provides a composition comprising a first component and a second component;

[0041] The first component includes the compounds as described in the first aspect;

[0042] The second component comprises a compound having the structure shown in Formula III:

[0043]

[0044] Among them, Ar 31 Ar 32 Each is independently selected from any one of single bond, C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) arylene or C6-C30 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, or C30, etc.) heteroarylene;

[0045] Ar 33 It is selected from any one of H, C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl or C6-C30 (e.g., C6, C8, C10, C12, C16, C20, C24, C28 or C30, etc.) heteroaryl;

[0046] p1 and p2 are each independently selected from 0, 1, 2, 3 or 4;

[0047] The hydrogen atom in the compound of formula III may be substituted by at least one of -D, -F, -CN, C6-C20 (e.g., C6, C8, C10, C12, C16 or C20), C1-C12 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12) alkyl, C1-C12 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12) alkoxy, trimethylsilyl, triphenylsilyl, tetraphenylmethyl.

[0048] As a preferred embodiment of the present invention, the compound of formula III is selected from any one of the following substituted or unsubstituted compounds:

[0049]

[0050]

[0051]

[0052] The substitution refers to the fact that each hydrogen atom in the above compound can be independently replaced by a deuterium atom.

[0053] It should be noted that there are no special restrictions on the preparation methods of the above compounds in this invention, and commonly used preparation methods in the art are applicable.

[0054] Preferably, the compound of formula III is selected from any one of the following compounds:

[0055] Fourthly, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode;

[0056] The organic thin film layer material includes the compounds described in the first aspect and / or the compositions of the third aspect.

[0057] As a preferred embodiment of the present invention, the organic thin film layer includes a light-emitting layer, and the main material of the light-emitting layer includes the compound described in the first aspect.

[0058] Preferably, the light-emitting layer is a phosphorescent light-emitting layer.

[0059] As a preferred embodiment of the present invention, the organic electroluminescent device is a blue phosphorescent organic electroluminescent device.

[0060] In this invention, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material is also called a dye or a phosphorescent material. The host material of the light-emitting layer can be a single compound or a mixture of two or more compounds.

[0061] The light-emitting layer includes a phosphorescent light-emitting layer, which includes a green phosphorescent light-emitting layer, a red phosphorescent light-emitting layer, and a yellow phosphorescent light-emitting layer.

[0062] The volume percentage of the main material in the phosphorescent luminescent layer is 60% to 99.9% (e.g., it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98%, or 99.9%), preferably 70% to 99.5%, and more preferably 85% to 95%.

[0063] In this invention, the doping material of the light-emitting layer can be a phosphorescent material, also known as a triplet luminescent material, which refers to the light emitted by a substance from a triplet excited state. The specific selection of phosphorescent materials in this invention is not particularly limited; commonly used doping materials for the light-emitting layer in this field are applicable, including but not limited to compounds having the structure shown in the formula PD.

[0064]

[0065] Wherein, M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu or Au;

[0066] Y1-Y4 are each independently selected from carbon or nitrogen;

[0067] Y1 and Y2 can be connected by a single key or a double key, and Y3 and Y4 can be connected by a single key or a double key.

[0068] Cy1 and Cy2 are each independently selected from any one of phenyl, naphthyl, fluorenyl, spirofluorenyl, indyl, pyrroleyl, thiopheneyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, isobenzothiopheneyl, benzimidazolyl, benzozolyl, triazolyl, tetrazolyl, diazolyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, N-hexacarbazolyl, N-hexadibenzofuranyl, wherein Cy1 and Cy2 may optionally be linked to each other via a single bond or an organic linking group;

[0069] Any two or more ligands of M can be connected by single or double bonds, or by O or S bridging, or by any chemical group or chemical structure to form a structure that conforms to chemical principles.

[0070] R 91 and R 92Each group is independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group, carboxylate group, sulfonic acid group, sulfonate group, phosphate group, phosphate group, -SF5, substituted or unsubstituted C1-C60 (e.g., can be C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55, or C60, etc.) alkyl, substituted or unsubstituted C2-C6. 0 (e.g., can be C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55, or C60, etc.) alkenyl, substituted or unsubstituted C2-C60 (e.g., can be C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55, or C60, etc.) alkynyl, substituted or unsubstituted C1-C60 (e.g., can be C1, C5, C10, C15, C20, C40, C50, C55, C60, etc.) alkyne, substituted or unsubstituted C1-C60 (e.g., can be C1, C5, C10, C15, C20, C50, C10, C15, C20, C1 ... 25. alkoxy, substituted or unsubstituted C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, or C10), heterocyclic alkyl, substituted or unsubstituted C6-C60 (e.g., C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54, or C60), aryl, substituted or unsubstituted C6-C60 (… For example, it can be any one of the following: aryloxy group (C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.), substituted or unsubstituted C6-C60 (e.g., it can be C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60, etc.), substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heterocyclic group.

[0071] a1 and a2 are each independent integers selected from 1 to 5, for example, they can be 1, 2, 3, 4 or 5;

[0072] b is an integer selected from 0 to 4, for example, it can be 0, 1, 2, 3 or 4;

[0073] a is selected from 1, 2, or 3;

[0074] L1 can be a monovalent organic ligand, a divalent organic ligand, or a trivalent organic ligand.

[0075] Preferably, the PD compound is selected from any one of the following compounds:

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082] In this invention, the organic thin film layer includes a hole layer, which comprises a hole injection layer, a hole transport layer, and an electron blocking layer.

[0083] The hole injection layer material includes a P-type dopant. A P-type dopant is a material that coexists with the hole injection layer material in the OLED device, oxidizing the hole injection layer material and thus acting as an electron acceptor to promote the movement of holes from the hole injection layer to the anode. In this 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 -0.2V, preferably greater than -0.1eV, more preferably greater than 0eV, more preferably greater than 0.1eV, and more preferably greater than 0.2eV.

[0084] The P-type dopant exists in the hole injection layer at a volume percentage of 1% to 10% (e.g., 1%, 2%, 4%, 6%, 8%, or 10%). In this invention, no particular limitation is made on the type of P-type dopant; exemplarily, compounds D-1 to D-13 disclosed in CN113728453A or compounds HI-1 to HI-9 as described below can be used.

[0085]

[0086]

[0087] In this invention, the hole layer material (including a hole injection layer, a hole transport layer, and an electron blocking layer) has the structure shown in the following formula HT-GH4:

[0088]

[0089] Among them, L 41 Selected from single-bonded, C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, and C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl;

[0090] Ar 41 Ar42 Each is independently selected from C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl groups and C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl groups;

[0091] X is selected from CR 41 R 42 Or NR 43 , where R 41 R 42 R 43 Each is independently selected from any one of substituted or unsubstituted phenyl groups (the substituents 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, dibenzofuranyl, naphthyl, triphenylene, fluoranyl, 9,9-dimethylfluorenyl, biphenyl, substituted or unsubstituted dibenzofuranyl (the substituent is phenyl), substituted or unsubstituted dibenzothiophene (the substituent is phenyl), dibenzofuran-substituted thiophene, C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkyl groups, R 41 R 42 A ring can be formed by connecting the links with a single key.

[0092] In this invention, the hole layer material (including a hole injection layer, a hole transport layer, and an electron blocking layer) further includes a compound having a structure as shown in Formula IA or a compound having a structure as shown in Formula IB:

[0093]

[0094] Wherein, L is selected from any one of C6 to C40 (e.g., it can be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) arylene, dibenzofuranyl or dibenzothiophene group;

[0095] m is selected from an integer between 0 and 4 (for example, it can be 0, 1, 2, 3 or 4), and n is selected from 0 or 1;

[0096] Ar is selected from any one of triphenylene, fluorene anthracene, dibenzofuranyl or dibenzothiophene;

[0097] Ar1 and Ar2 are each independently selected from any one of aryl, dibenzofuranyl, or dibenzothiophene groups containing C6 to C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.);

[0098] Ar1 and Ar, Ar2 and Ar, and Ar1 and Ar2 can be independently connected or bridged by single bonds, O, S, CR1R2, NR.

[0099] R, R1, and R2 are each independently selected from any one of the following: C1 to C20 (e.g., C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, or C20), alkyl, C6 to C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40), aryl, dibenzofuranyl, or dibenzothiopheneyl.

[0100] In compounds of formula IB and formula IA, the H atom can be independently replaced by at least one of -F, -CN, -D (deuterium atom), C1-C6 alkyl, C1-C6 alkoxy, phenyl, biphenyl, naphthyl, phenanthryl, anthraceneyl, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, spirofluorenyl, indo[a]fluorenyl, or hydrogenated benzo[a]anthryl.

[0101] Preferably, the Ar is fluoreneanthracene, where m+n>1.

[0102] Preferably, the H in the compounds of formula IB and formula IA can be replaced by at least one of -F, -CN, -D, C1-C3 alkyl (e.g., methyl, ethyl, or propyl), C1-C3 alkoxy (e.g., methoxy, ethoxy, or propoxy), phenyl, biphenyl, triphenylene, or fluoranthyl.

[0103] Preferably, L, Ar1, and Ar2 are each independently selected from at least one of phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, perylene, spirofluorenyl, indo[a]fluorenyl, or hydrogenated benzo[a]anthryl.

[0104] Preferably, the compound with the structure shown in Formula IA or the compound with the structure shown in Formula IB is selected from any one of the following compounds 1-112:

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] Preferably, the material of the electron blocking layer is a compound of Formula IA or a compound of Formula IB.

[0111] In the OLED device provided by this invention, the hole layer material, in addition to the compounds described in formula HT-GH4, formula I or IIB, and formula I or IIA, may also include conventional hole materials in the art, without particular limitation. Exemplarily, it includes, but is not limited to, triarylamine compounds or carbazole compounds. Preferably, triarylamine compounds or carbazole compounds containing three or more nitrogen atoms are used because they have a higher HOMO (lower absolute value) and are more suitable as hole injection layer materials. Triarylamine compounds or carbazole compounds containing two or one nitrogen atom can be used as hole transport layer materials. Some compounds or carbazole compounds containing one nitrogen atom, if they have a high LUMO, can also be used as electron blocking layer materials.

[0112] The triaryl amine compound or carbazole compound is used as the hole layer material, and the hole layer material includes the following structure:

[0113]

[0114] Among them, Ar 601 ~Ar 609 Each is independently selected from any one of the following: substituted or unsubstituted C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted naphthobenzothiophene, substituted or unsubstituted dinaphthofuranyl, substituted or unsubstituted dinaphthothiophene.

[0115] And Ar 601 ~Ar 609 Ar atoms that are adjacent to or connected to the same N atom 601 ~Ar 609 It can be connected via a single key or via O, S, CR 701 R 702 NR 703 bridging;

[0116] R 701 R702 R 703 Selected from C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl, C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkyl, and R 701 R 702 It can be connected with a single button.

[0117] Hole blocking layers (HBLs) can confine holes and / or excitons within the emissive layer to improve device current efficiency and lifetime. Compared to emissive layer materials closest to the HBL interface, HBL materials exhibit lower HOMO (larger absolute values) and / or higher triplet energies.

[0118] An electron transport layer (ETL) may comprise a material capable of transporting electrons. The ETL may be intrinsic (undoped) or doped, and doping can be used to enhance conductivity. In this invention, there are no particular limitations on the ETL material; any metal complex or organic compound can be used, as long as it can transport electrons. Generally, electron transport layer materials contain at least one of the following structural segments: pyridine, pyrimidine, triazine, benzimidazole, benzoxazole, benzothiazole, N-naphthalene, N-phenanthion, N-carbazole, N-dibenzofuran, and N-dibenzothiophene.

[0119] In this invention, no special restrictions are placed on the electron transport layer material, which includes, but is not limited to, the following:

[0120]

[0121]

[0122] In this invention, the cathode material is a metal with low work function (e.g., alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.)), a metal alloy composed of multiple metals (an alloy composed of alkali metals or alkaline earth metals 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 relatively high work function can also be used, such as Ag or Al. In this case, combinations of the metals are typically used, such as Ca / Ag, Mg / Ag, or Ba / Ag.

[0123] Alternatively, a thin interlayer of material with a high dielectric constant can 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 can be an alkali metal or alkaline earth metal fluoride, as well as the corresponding oxide or carbonate (e.g., LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.) or lithium quinoline (LiQ).

[0124] Compared with the prior art, the present invention has the following beneficial effects:

[0125] In this invention, the structure of the compound is designed to be suitable as the main material for the phosphorescent light-emitting layer of organic electroluminescent devices, thereby enabling the organic electroluminescent devices to have high current efficiency and long lifespan. Detailed Implementation

[0126] To facilitate understanding of the present invention, the following embodiments are provided. Those skilled in the art should understand that these embodiments are merely illustrative and should not be construed as limiting the scope of the invention.

[0127] Synthesis of intermediate P6-1 in Preparation Example 1

[0128] This preparation example provides intermediate P6-1 and its synthesis method, which is as follows:

[0129] (1) Synthesis of intermediate M0-1

[0130]

[0131] In a 250 mL three-necked flask, add 4.1 g of the compound shown in M0 and 60 mL of tetrahydrofuran. Under nitrogen protection, cool to -78 °C and slowly add 1.6 M of butyllithium in n-hexane (0.01 mol of butyllithium). After the addition is complete, maintain the temperature at -78 to -70 °C for 30 minutes. Then, add 0.015 mol of trimethyl borate in one go and slowly raise the temperature to room temperature. Add an aqueous solution of ethyl acetate and ammonium chloride, separate the layers, wash the organic layer with water, concentrate to dryness under reduced pressure, and proceed directly to the next reaction without separation.

[0132] (2) Synthesis of intermediate M-1Si

[0133]

[0134] Under nitrogen protection, 100 mL of dioxane, intermediate M0-1 prepared in step (1), 1.8 g of trichloromethazine, 2.12 g (0.02 mol) of sodium carbonate and 0.23 g (0.0002 mol) of tetraphenylphosphine palladium were added sequentially to a 250 mL three-necked flask. The mixture was slowly heated to 40 °C and reacted for 2 h, then heated to 60 °C and reacted for 4 h, then heated to reflux and reacted for 2 h. The mixture was cooled to room temperature, and water and dichloromethane were added to separate the layers. The organic layer was washed with water and dried with magnesium sulfate. After removing the desiccant, the mixture was concentrated to dryness and separated by silica gel column chromatography. The mixture was eluted with petroleum ether: dichloromethane: THF = 10:2:1 (volume ratio) to obtain 2.6 g of intermediate M-1Si.

[0135] The obtained intermediate M-1Si was subjected to mass spectrometry, and the mass-to-charge ratio (m / z) was measured to be 481.06.

[0136] (3) Synthesis of intermediate P6-1

[0137]

[0138] Under nitrogen protection, 0.01 mol of intermediate M-1Si, 0.011 mol of carbazole, 200 mL of acetonitrile, and 0.014 mol of potassium carbonate were added to a 500 mL three-necked flask. The mixture was heated to reflux and reacted for 6 h. The temperature was then lowered to 25 °C, water was added, and the resulting solid was filtered. The solid was washed with water, dried under reduced pressure, and then crystallized twice with a mixed solvent of ethyl acetate, chloroform, and toluene to obtain 3.1 g of intermediate P6-1.

[0139] The obtained intermediate P6-1 was subjected to mass spectrometry analysis, and the mass-to-charge ratio (m / z) was measured to be 612.15.

[0140] Preparation Example 2: Synthesis of Intermediate P6-1D

[0141] This preparation example provides intermediate P6-1D and its synthesis method, which is as follows:

[0142]

[0143] The specific synthesis method is the same as that of P6-1, except that the carbazole in step (3) is replaced with an equal amount of deuterated carbazole to obtain intermediate P6-1D.

[0144] The obtained intermediate P6-1D was analyzed by mass spectrometry, and the mass-to-charge ratio (m / z) was measured to be 620.20.

[0145] Synthesis Example 1: Synthesis of Compound P1

[0146] This synthetic example provides compound P1 and its synthetic method, which is as follows:

[0147]

[0148] Under nitrogen protection, 200 mL of dioxane was added to a 500 mL three-necked flask, followed by 0.01 mol of intermediate P1-1, 0.011 mol of intermediate P1-2, 2.12 g of sodium carbonate, and 0.23 g of tetraphenylphosphine palladium. The mixture was slowly heated to 40 °C and reacted for 2 h, then heated to 60 °C and reacted for 4 h, and then heated to reflux and reacted for 2 h. The mixture was then cooled to room temperature, and water and dichloromethane were added for separation. The organic layer was washed with water, dried with magnesium sulfate, and after removing the desiccant, concentrated to dryness. The mixture was then separated by silica gel column chromatography, eluted with petroleum ether:dichloromethane:THF = 10:2:1 (volume ratio), yielding 5.8 g of compound P1.

[0149] The obtained compound P1 was analyzed by mass spectrometry, and the mass-to-charge ratio (m / z) was found to be 804.27.

[0150] Synthesis Examples 2-13

[0151] Synthesis Examples 2-13 provide the following compounds and their synthesis methods in sequence. The synthesis methods are the same as those in Synthesis Example 1, except that intermediate P1-2 is replaced with other boric acid compounds in equal amounts, and intermediate P1-1 is replaced with other chlorinated compounds (see Table 1 for details). In addition, the proportions of reactants can be adjusted according to the specific reaction raw materials and common knowledge in the art. Mass spectrometry was performed on the following compounds, and the mass-to-charge ratios (m / z) are shown in Table 1.

[0152] Table 1

[0153]

[0154]

[0155]

[0156] For other compounds whose specific synthesis methods are not listed, they can be synthesized by referring to the above examples and combining them with common knowledge in the field.

[0157] The specific structures of some of the compounds used in the following application examples and comparative application examples of this invention are as follows:

[0158]

[0159]

[0160] Application Example 1

[0161] This application example provides a blue organic electroluminescent device, using the composition provided by the present invention as the host material for the light-emitting layer. The structure of the blue organic electroluminescent device is as follows:

[0162] ITO / HT-1: HI-2[5%](80nm) / HT-1(30nm) / EB-1(20nm) / Main material: PBD-1[5%](35nm) / ETL-1(25nm) / LiF(0.5nm) / Al(150nm).

[0163] The fabrication method of the blue organic electroluminescent device is as follows:

[0164] The material was placed inside a vacuum chamber, and the vacuum was evacuated to 1×10⁻⁶. -5 ~1×10 -6 Pa is sequentially vacuum-deposited onto a cleaned ITO substrate to fabricate OLED devices.

[0165] Wherein PBD-1[5%] refers to the doping ratio of the dye, that is, the volume ratio of the host material to the dye PBD-1 is 95:5; 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 to the p-type dopant HI-2 is 95:5. HT-1 is the hole transport material; HT-1:HI-2[5%] is used as the hole injection layer, and EB-1 is the electron blocking layer.

[0166] The main material of the light-emitting layer of the blue organic electroluminescent device provided in this application example is compound P1 and H-1, and the volume ratio of P1 to H-1 is 1:1.

[0167] Application Example 2-16

[0168] Application Examples 2-16 provide a blue organic electroluminescent device, which differs from Application Example 1 only in that the main material of the light-emitting layer is replaced with other compounds. If the main material of the light-emitting layer has two components, the volume ratio of the two components is 1:1 (see Table 2 for details). Other preparation steps and conditions are the same as in Application Example 1.

[0169] Compare and contrast examples 1-5

[0170] Comparative Application Examples 1-5 provide an organic electroluminescent device, which differs from Application Example 1 only in that the main material 1 of the light-emitting layer is different (see Table 2 for details). The other preparation steps and conditions are the same as those in Application Example 1.

[0171] Performance testing

[0172] The brightness, driving voltage, current efficiency, and LT95 of the organic electroluminescent devices provided above were tested using the OLED-1000 multi-channel accelerated aging lifetime and photoluminescence performance analysis system manufactured by Hangzhou Yuanfang. Current efficiency is the value corresponding to a brightness of 1000 cd / m², 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 maintaining an initial current density of 10 mA / cm². Both current efficiency and LT95 are relative values. Specific test results are shown in Table 2.

[0173] Table 2

[0174] Application Example 1 P1 H-1 1000 1 1 Application Example 2 P1 H-2 1000 0.96 1.06 Application Example 3 P2 H-1 1000 1.11 1.21 Application Example 4 P2 H-3 1000 1.20 1.02 Application Example 5 P3 H-1 1000 1.09 1.11 Application Example 6 P4 H-1 1000 1.05 1.06 Application Example 7 P5 H-1 1000 1.07 1.08 Application Example 8 P6 H-1 1000 1.09 1.88 Application Example 9 P6-D H-1 1000 1.07 2.67 Application Example 10 P7 H-1 1000 1.01 3.02 Application Example 11 P8 H-1 1000 1.65 3.11 Application Example 12 P9 H-1 1000 1.32 1.11 Application Example 13 P10 H-1 1000 1.01 4.26 Application Example 14 P11 H-1 1000 1.11 1.09 Application Example 15 P2 / 1000 0.69 0.77 Application Example 16 P3 / 1000 0.78 0.88 Comparative Application Example 1 D1 H-1 1000 0.89 0.77 Comparative Application Example 2 D2 H-1 1000 0.92 0.93 Comparative Application Example 3 D3 H-1 1000 0.58 0.67 Comparative Application Example 4 D1 / 1000 0.54 0.31 Comparative Application Example 5 D2 / 1000 0.61 0.28

[0175] In the table above, " / " indicates that this component is not present. The corresponding application example is that the main material of the light-emitting layer is a single component.

[0176] As can be seen from Table 2, in this invention, by designing the main material of the light-emitting layer, and further by combining the compound with the structure shown in Formula I or Formula II with the compound with the structure shown in Formula III, the prepared electroluminescent device has high current efficiency and long service life.

[0177] Application Example 17

[0178] Application Example 17 provides a blue organic electroluminescent device, which differs from Application Example 1 only in that the electron blocking layer material is replaced by EB-2 instead of EB-1, as shown in Table 3. Other preparation steps and conditions are the same as in Application Example 1.

[0179] Table 3

[0180] Application Example 17 P1 H-1 1000 1.22 1.08

[0181] Application Example 18

[0182] Application Example 18 provides a blue organic electroluminescent device, which differs from Application Example 3 only in that the electron blocking layer material is replaced by EB-2 instead of EB-1, as detailed in Table 4. Other preparation steps and conditions are the same as in Application Example 3.

[0183] Table 4

[0184] Application Example 18 P2 H-1 1000 1.29 1.36

[0185] As can be seen from Tables 3 and 4, the use of EB-2 as the electron blocking layer material in this invention can further improve the current efficiency and lifespan of organic electroluminescent devices.

[0186] As can be seen from the above, by designing the structure of the compound, this invention makes it suitable as the main material for the phosphorescent light-emitting layer of organic electroluminescent devices, thereby enabling the organic electroluminescent devices to have high current efficiency and long lifespan.

[0187] The applicant declares that the detailed process flow of this invention is illustrated by the above embodiments, but this invention is not limited to the above detailed process flow, that is, it does not mean that this invention must rely on the above detailed process flow to be implemented. Those skilled in the art should understand that any improvements to this invention, equivalent substitutions of raw materials for the product of this invention, addition of auxiliary components, and selection of specific methods, etc., all fall within the protection scope and disclosure scope of this invention.

Claims

1. A triazine compound, characterized in that, The triazine compounds have the structure shown in Formula I or Formula II: ； Where n is 1; Ar1 is selected from any one of phenylene, naphthylene, biphenylene, carbazolyl, dibenzofuranylene, dibenzothiopheneylene, or fluoreneylene; Ar2 is selected from any one of phenyl, naphthyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothiopheneyl or fluorenyl; X is selected from O or S; , In this context, Y represents Si. Y is selected from C or Si; R1 and R2 are each independently selected from C6-C20 aryl or C1-C12 alkyl, and R1 and R2 can be linked together to form a ring by a single bond; In the compounds shown in Formula I and Formula II, the hydrogen atoms can be independently replaced by -D, -F, -CN, C6-C20 aryl or C1-C12 alkyl groups.

2. A triazine compound, characterized in that, The triazine compounds have the structure shown in Formula I or Formula II: ； Where n is 0; Ar2 is selected from carbazolyl; X is selected from O or S; , In this context, Y represents Si. Y is selected from C or Si; R1 and R2 are each independently selected from C6-C20 aryl or C1-C12 alkyl, and R1 and R2 can be linked together to form a ring by a single bond; In the compounds shown in Formula I and Formula II, the hydrogen atoms can be independently replaced by -D, -F, -CN, C6-C20 aryl or C1-C12 alkyl groups.

3. The triazine compound according to claim 1 or 2, characterized in that, In the compounds of Formula I and Formula II, the hydrogen atoms can be independently substituted by at least one of -D, -F, -CN, phenyl, naphthyl, biphenyl, methyl, ethyl, propyl, or butyl.

4. A triazine compound, characterized in that, The triazine compound is selected from any one of the following substituted or unsubstituted triazine compounds: The substitution refers to the fact that each hydrogen atom in the above triazine compounds can be independently replaced by a deuterium atom.

5. An intermediate, characterized in that, The intermediate includes the following compounds: 、 ； The intermediate is used to prepare the triazine compound as described in any one of claims 2-4.

6. A composition, characterized in that, The composition comprises a first component and a second component; The first component includes a triazine compound as described in any one of claims 1-4; The second component comprises a compound having the structure shown in Formula III: ； Among them, Ar 31 Ar 32 Each is independently selected from any one of single bonds, C6-C40 arylene, or C6-C30 heteroarylene; Ar 33 Selected from any one of H, C6-C40 aryl, or C6-C30 heteroaryl; p1 and p2 are each independently selected from 0, 1, 2, 3 or 4; In compounds of formula III, each hydrogen atom can be independently substituted by at least one of -D, -F, -CN, C6-C20 aryl, C1-C12 alkyl, C1-C12 alkoxy, trimethylsilyl, triphenylsilyl, and tetraphenylmethyl.

7. The composition according to claim 6, wherein the compound of formula III is selected from any one of the following substituted or unsubstituted compounds: ； The substitution refers to the fact that each hydrogen atom in the above compound can be independently replaced by a deuterium atom.

8. 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 organic thin film layer material includes the compounds as described in any one of claims 1-4 and / or the compositions as described in claims 6 or 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic thin film layer includes a light-emitting layer, and the main material of the light-emitting layer includes the compound as described in any one of claims 1-4.

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

11. The organic electroluminescent device according to claim 8, characterized in that, The organic thin film layer further includes a hole layer, the material of which comprises a compound having a structure as shown in Formula IA or a compound having a structure as shown in Formula IB: 、 ； Wherein, L is selected from any one of C6~C40 arylene, dibenzofuranyl or dibenzothiophene; m is selected from an integer between 0 and 4, and n is selected from 0 or 1; Ar is selected from any one of triphenylene, fluorene anthracene, dibenzofuranyl or dibenzothiophene; Ar1 and Ar2 are each independently selected from any one of C6-C40 aryl, dibenzofuranyl, or dibenzothiopheneyl groups; Ar1 and Ar, Ar2 and Ar, and Ar1 and Ar2 can be independently connected or bridged by single bonds, O, S, CR1R2, NR; R, R1, and R2 are each independently selected from any one of C1-C20 alkyl, C6-C40 aryl, dibenzofuranyl, or dibenzothiopheneyl. In compounds of formula IB and formula IA, the H can be independently replaced by at least one of -F, -CN, -D, C1-C6 alkyl, C1-C6 alkoxy, phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, triphenylene, fluoranyl, pyrene, peryl, spirofluorenyl, indo[a]fluorenyl, or hydrogenated benzo[a]anthryl.

12. The organic electroluminescent device according to claim 11, characterized in that, The hole layer includes a hole injection layer, a hole transport layer, and an electron blocking layer.

13. The organic electroluminescent device according to claim 12, characterized in that, The electron blocking layer is made of a compound of formula IA or a compound of formula IB.

14. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device is a blue phosphorescent organic electroluminescent device.

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