Triazine compound containing carbazole substituent and organic electroluminescent device

Abstract

The invention provides a triazine compound containing a carbazole substituent group and an organic electroluminescent device. The triazine compound containing the carbazole substituent has a structure shown in a formula I. By designing the structure of the triazine compound containing the carbazole substituent group, the triazine compound containing the carbazole substituent group with excellent performance is prepared, so that the triazine compound containing the carbazole substituent group is used as a material of a light-emitting layer; and the prepared organic light-emitting device has relatively high current efficiency, relatively long service life and relatively low driving voltage.

Description

Technical Field

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

[0002] Compared with other flat panel displays (for example, liquid crystal displays (LCDs), plasma display panels (PDPs), field emission displays (FEDs), etc.), organic electroluminescent devices (OLEDs) have a simpler structure, various processing advantages, higher brightness, excellent viewing angle characteristics, faster response speeds, and lower driving voltages. Therefore, they are also fully developed to be used as light sources for flat panel displays (for example, wall-mounted TVs, etc.), or as backlight units for displays, illuminators, billboards, etc.

[0003] The structure of an organic electroluminescent device specifically includes an anode, a cathode, and an organic layer therebetween. In order to improve the efficiency and stability of an organic electroluminescent element, the organic material layer includes multiple layers with different materials. In order to meet people's higher requirements for OLED devices, the field urgently needs to develop more types of materials to improve the performance of OLED devices in terms of current efficiency, life span, etc. Summary of the invention

[0004] In view of the shortcomings of the prior art, the object of the present invention is to provide a triazine compound containing a carbazole substituent and an organic electroluminescent device. The present invention designs the structure of the triazine compound containing a carbazole substituent to prepare a triazine compound containing a carbazole substituent with excellent performance. The triazine compound containing a carbazole substituent is used as a material for a light-emitting layer, and the prepared organic electroluminescent device has high current efficiency, long life and low driving voltage.

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

[0006] In a first aspect, the present invention provides a triazine compound containing a carbazole substituent, wherein the triazine compound containing a carbazole substituent has a structure as shown in the following formula I:

[0007]

[0008] Wherein, Ar is selected from any one or a combination of at least two of phenylene, naphthylene, biphenylene, triphenylene, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl or dibenzothiophenylene;

[0009] Dashed lines indicate single bonds or their absence;

[0010] n is selected from 0 or 1;

[0011] R1-R8 are each independently selected from one of H, phenyl, naphthyl, biphenyl, triphenylene, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl, and at least two of R1-R8 are not selected from H;

[0012] When R3 and R6 are both selected from phenyl, R1, R2, R4, R5, R7, and R8 are selected from H, n is selected from 0;

[0013] When R2 and R7 are both selected from phenyl, R1, R3, R4, R5, R6, and R8 are selected from H, n is selected from 0;

[0014] When one of R1-R8 is selected from carbazolyl, n is selected from 1;

[0015] The hydrogen atoms in the compound of formula I can be replaced by deuterium atoms (D), -F, -CN, C1-C12 alkyl, C1-C12 alkoxy, triphenylsilyl ( The dotted line indicates the connection site, the same below), triphenylmethyl Substituted with at least one of C6-C20 heteroaryl and fluorenyl;

[0016] The triazine compounds containing carbazole substituents do not include the following compounds:

[0017]

[0018]

[0019] The present invention designs the structure of triazine compounds containing carbazole substituents to prepare triazine compounds containing carbazole substituents with excellent performance. The triazine compounds containing carbazole substituents are used as materials for light-emitting layers, and the prepared organic electroluminescent device has high current efficiency, long life and low driving voltage.

[0020] In the present invention, C1-C12 can be C1, C2, C3, C4, C5, C6, C7, C8, C9 or C12.

[0021] C6-C20 can be C6, C10, C12, C15, C18 or C20, etc.

[0022] In the present invention, "D" represents a deuterium atom. Unless otherwise indicated in the present invention, H and hydrogen therein all represent "protium", and the same shall apply hereinafter.

[0023] It should also be noted that, if n represents 0, Ar represents any one selected from phenyl, naphthyl, biphenyl, triphenylene, fluorenyl, carbazolyl, dibenzofuranyl or dibenzothiophenylene, or a combination of at least two thereof; if n represents 0, Ar represents any one selected from phenylene, naphthyl, biphenylene, triphenylene, fluorenyl, carbazolyl, dibenzofuranyl or dibenzothiophenylene, or a combination of at least two thereof.

[0024] The following are preferred technical solutions of the present invention, but are not intended to limit the technical solutions provided by the present invention. Through the following preferred technical solutions, the objectives and beneficial effects of the present invention can be better achieved and realized.

[0025] As a preferred technical solution of the present invention, the C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, butyl, pentyl, methylcyclopentyl, hexyl, methylcyclohexyl, heptyl, octyl or adamantyl, bicyclo[2.2.1]heptyl or bicyclo[2.2.2]octyl.

[0026] Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy.

[0027] Preferably, the C6-C20 heteroaryl group is selected from any one of a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group.

[0028] As a preferred technical solution of the present invention, the n is selected from 0, and the Ar is selected from any one of phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl or 9,9-dimethylfluorenyl.

[0029] As a preferred technical solution of the present invention, the n is selected from 1, and the Ar is selected from any one of phenylene, naphthylene or biphenylene, preferably phenylene.

[0030] As a preferred technical solution of the present invention, the hydrogen atoms in the compound of formula I can be independently replaced by at least one of a deuterium atom (D), -F, -CN, a methoxy group, an ethoxy group, a propoxy group, a methyl group, an ethyl group, a propyl group, a tert-butyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, and a triphenylsilyl group.

[0031] Preferably, the hydrogen atoms in the compound of formula I can be replaced independently by any one of a deuterium atom (D), -F, -CN, a methyl group, an ethyl group, a tert-butyl group or a methoxy group.

[0032] As a preferred technical solution of the present invention, the triazine compound containing a carbazole substituent is selected from any one of the following substituted or unsubstituted compounds:

[0033]

[0034]

[0035]

[0036] The substitution means that the hydrogen atoms in the triazine compound containing the carbazole substituent can be independently replaced by deuterium atoms.

[0037] Preferably, the triazine compound containing a carbazole substituent is selected from any one of the following compounds:

[0038]

[0039] In the present invention, there is no special limitation on the preparation method of the triazine compound containing carbazole substituents, and any commonly used preparation method in the art is applicable.

[0040] In a second aspect, 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;

[0041] The material of the organic thin film layer includes the triazine compound containing carbazole substituents as described in the first aspect.

[0042] Preferably, the organic thin film layer comprises a light-emitting layer, and a main material of the light-emitting layer comprises the triazine compound containing a carbazole substituent as described in the first aspect.

[0043] Preferably, the light-emitting layer is a phosphorescent light-emitting layer.

[0044] As a preferred technical solution of the present invention, the organic electroluminescent device is a blue light organic electroluminescent device.

[0045] The luminescent layer in the present invention includes a luminescent layer main material and a doping material, wherein the doping material is also called a dye or a phosphorescent luminescent material. The luminescent layer main material can be a single compound or a mixture of two or more compounds.

[0046] 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, a yellow phosphorescent light-emitting layer, and a blue phosphorescent light-emitting layer.

[0047] The volume percentage of the main material in the phosphorescent layer is 60% to 99.9% (for example, it can be 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 98% or 99.9%, etc.), preferably 70% to 99.5%, and more preferably 85% to 95%.

[0048] In the present invention, the doping material of the light-emitting layer may be a phosphorescent material, which is also called a triplet light-emitting material, and refers to the light emitted from a triplet excited state. The specific selection of the phosphorescent material in the present invention is not particularly limited, and the doping materials of the light-emitting layer commonly used in the art are applicable, including but not limited to: a compound having a structure shown in Formula PD:

[0049]

[0050] Wherein, M is selected from any one of Ir, Pt, Pd, Os, Ti, Zr, Hf, Eu, Tb, Tm, Cu or Au;

[0051] Y1-Y4 are each independently selected from carbon or nitrogen;

[0052] Y1 and Y2 can be connected by a single bond or a double bond, and Y3 and Y4 can be connected by a single bond or a double bond;

[0053] Cy1 and Cy2 are each independently selected from phenyl, naphthyl, fluorenyl, spirofluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothienyl, benzimidazolyl, benzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, N-heterocarbazolyl, N-heterodibenzofuranyl, wherein Cy1 and Cy2 may be optionally linked to each other via a single bond or an organic linking group;

[0054] Any two ligands of M, or more than two ligands, may be connected by a single bond or a double bond, or may be bridged by O or S, or may be connected by any chemical group or chemical structure to form a structural form that conforms to chemical principles;

[0055] R 91 and R 92each independently selected from -H, -D, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid, carboxylate, sulfonic acid, sulfonate, phosphoric acid, phosphate, -SF5, substituted or unsubstituted C1-C60 (e.g., C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkyl, substituted or unsubstituted C2-C6 C2-C60 (for example, C2, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) alkynyl, substituted or unsubstituted C1-C60 (for example, C1, C5, C10, C15, C20, C25, C30, C35, C40, C45, C50, C55 or C60, etc.) C2-C10 (for example, C2, C3, C4, C5, C6, C7, C8, C9 or C10) heterocycloalkyl, substituted or unsubstituted C6-C60 (for example, C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryl, substituted or unsubstituted C6-C60 (for example, C2, C3, C4, C5, C6, C7, C8, C9 or C10) For example, it can be any one of C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) aryloxy, substituted or unsubstituted C6-C60 (for example, it can be C6, C12, C15, C18, C24, C30, C32, C36, C40, C42, C54 or C60) arylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0056] a1 and a2 are each independently an integer selected from 1-5, for example, 1, 2, 3, 4 or 5;

[0057] b is an integer selected from 0-4, for example, 0, 1, 2, 3 or 4;

[0058] a is selected from 1, 2 or 3;

[0059] L1 is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

[0060] Preferably, the compound of formula PD is selected from any one of the following compounds:

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067] 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.

[0068] The hole injection layer material includes a P-type dopant. The P-type dopant refers to a dopant 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 to 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 -0.2V, preferably greater than -0.1eV, more preferably greater than 0eV, more preferably greater than 0.1eV, and more preferably greater than 0.2eV.

[0069] The P-type dopant is present in the hole injection layer in a volume percentage of 1% to 10% (e.g., 1%, 2%, 4%, 6%, 8% or 10%). In the present invention, there is no particular limitation on the type of the P-type dopant, and illustratively, the compounds D-1 to D-13 disclosed in CN113728453A or the compounds HI-1 to HI-9 described below can be selected:

[0070]

[0071] In the present invention, the hole layer material (including the hole injection layer, the hole transport layer and the electron blocking layer) has a structure shown in the following formula HT-GH4:

[0072]

[0073] Among them, L 41 is selected from a single bond, a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl, or a C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl;

[0074] Ar 41 ,Ar 42Each is independently selected from C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl, C6-C20 (for example, C6, C8, C10, C12, C16 or C20, etc.) heteroaryl;

[0075] X is selected from CR 41 R 42 or NR 43 , where R 41 , R 42 , R 43 Each is independently selected from substituted or unsubstituted phenyl (the substituted substituent is selected from C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkyl, C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkoxy, dibenzofuranyl), naphthyl, triphenylene, fluoranthene, 9,9-dimethylfluorenyl, biphenyl, substituted or unsubstituted dibenzofuranyl (the substituted substituent is phenyl), substituted or unsubstituted dibenzothienyl (the substituted substituent is phenyl), dibenzofuran-substituted thienyl, C1-C6 (for example, C1, C2, C3, C4, C5 or C6) alkyl, any one of R 41 , R 42 They can be linked to form rings via single bonds.

[0076] In the present invention, the hole layer material (including the hole injection layer, the hole transport layer and the electron blocking layer) also includes a compound having a structure shown in the following formula IA or a compound having a structure shown in the following formula IB:

[0077]

[0078] Wherein, L is selected from any one of C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) arylene, dibenzofuranyl or dibenzothiophenyl;

[0079] 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;

[0080] Ar is selected from any one of triphenylene, fluoranthenylene, dibenzofuranylene or dibenzothiophenylene;

[0081] Ar1 and Ar2 are each independently selected from any one of a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl group, a dibenzofuranyl group or a dibenzothiophenyl group;

[0082] Ar1 and Ar, Ar2 and Ar, and Ar1 and Ar2 can each independently be connected or bridged by a single bond, O, S, CR1R2, or NR.

[0083] R, R1, and R2 are each independently selected from any one of a C1-C20 (e.g., C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, or C20, etc.) alkyl group, a C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aryl group, a dibenzofuranyl group, or a dibenzothiophenyl group;

[0084] The hydrogen atoms in the compound of formula IB and the compound of formula IA may each independently be replaced by at least one of -F, -CN, -D (deuterium atom), C1-C6 alkyl, C1-C6 alkoxy, phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, triphenylene, fluoranthenyl, pyrenyl, perylenyl, spirofluorenyl, indenofluorenyl or hydrogenated benzanthryl.

[0085] Preferably, Ar is a fluoranthenyl group, and m+n>1.

[0086] Preferably, 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 (for example, methyl, ethyl or propyl), C1-C3 alkoxy (for example, methoxy, ethoxy or propoxy), phenyl, biphenyl, triphenylene, and fluoranthene.

[0087] Preferably, L, Ar1, Ar2 are each independently selected from at least one of phenyl, biphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, triphenylene, fluoranthenyl, pyrene, perylenyl, spirofluorenyl, indenofluorenyl or hydrogenated benzanthryl.

[0088] Preferably, the compound of formula IB is selected from any one of the following compounds:

[0089]

[0090]

[0091]

[0092] In the OLED device provided by the present invention, the hole layer material may include conventional hole materials in the art in addition to the compound described in formula HT-GH4, the compound of formula IB, and the compound of formula IA, without special restrictions. Exemplary includes but is not limited to: triarylamine compounds or carbazole compounds. Triarylamine compounds or carbazole compounds containing more than 3 N atoms are preferred, because the HOMO of triarylamine compounds or carbazole compounds containing more than 3 N atoms is higher (smaller absolute value), and is more suitable for use as hole injection layer materials. Triarylamine compounds or carbazole compounds containing 2 or 1 N atoms can be used as hole transport layer materials. Some compounds or carbazole compounds containing 1 N atom, if they have a higher LUMO, can also be used as electron blocking layer materials.

[0093] The triarylamine compound or the carbazole compound is used as the hole layer material, and the hole layer material includes the following structure:

[0094]

[0095] Among them, Ar 601 ~Ar 609 Each independently selected from a substituted or unsubstituted C6-C40 (for example, C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36 or C40, etc.) aryl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted naphthobenzofuranyl, a substituted or unsubstituted naphthobenzothiophenyl, a substituted or unsubstituted dinaphthofuranyl, a substituted or unsubstituted dinaphthothiophenyl;

[0096] And Ar 601 ~Ar 609 Ar atoms adjacent to or connected to the same N atom 601 ~Ar 609 , can be connected by single key or through O, S, CR 701 R 702 NR 703 bridging;

[0097] R 701 , R 702 , R 703 is selected from C6-C40 (e.g., C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, or C40, etc.) aromatic groups, C6-C20 (e.g., C6, C8, C10, C12, C16, or C20, etc.) heteroaryl groups, C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkyl groups, and R 701 , R702 Can connect via one-touch.

[0098] The hole blocking layer (HBL) can confine holes and / or excitons within the EL to improve the current efficiency and lifetime of the device. Compared with the EL material closest to the HBL interface, the HBL material has a lower HOMO (larger absolute value) and / or higher triplet energy.

[0099] The electron transport layer (ETL) may include a material capable of transporting electrons. The electron transport layer may be intrinsic (undoped) or doped, and doping may be used to enhance conductivity. In the present invention, there is no particular restriction on the ETL material, and any metal complex or organic compound may be used as long as it can transport electrons. The general electron transport layer material contains the following structural fragments: at least one of a pyridine structure, a pyrimidine structure, a triazine structure, a benzimidazole structure, a benzoxazole structure, a benzothiazole structure, an N-naphthalene structure, an N-coffee structure, an N-carbazole structure, an N-dibenzofuran structure, and an N-dibenzothiophene structure.

[0100] In the present invention, there is no special restriction on the electron transport layer material, which exemplarily includes but is not limited to:

[0101]

[0102]

[0103]

[0104] In the present invention, the material of the cathode is a metal with a low work function (e.g., alkaline earth metal, alkali metal, main group metal or lanthanide element (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.)), a metal alloy composed of multiple metals (alloy composed of alkali metal or 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 relatively high work functions, 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.

[0105] It is also possible to introduce a thin intermediate layer of a material with a high dielectric constant 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, and corresponding oxides or carbonates (such as LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.) or lithium quinoline (LiQ) can be selected.

[0106] Compared with the prior art, the present invention has the following beneficial effects:

[0107] The present invention designs the structure of triazine compounds containing carbazole substituents to prepare triazine compounds containing carbazole substituents with excellent performance. The triazine compounds containing carbazole substituents are used as materials for light-emitting layers, and the prepared organic electroluminescent device has high current efficiency, long life and low driving voltage. DETAILED DESCRIPTION

[0108] 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.

[0109] Synthesis Example 1 Synthesis of Compound P1

[0110] This synthesis example provides compound P1 and its synthesis method, the synthesis method is as follows:

[0111]

[0112] Under a nitrogen atmosphere, dry toluene (100 mL), intermediate P1-1 (3.6 g), intermediate P1-2 (3.2 g), Pd(dba)2 (bis(dibenzylideneacetonepalladium, 0.1 g), 0.8 g of 10% tri-tert-butylphosphine toluene solution (the mass of tri-tert-butylphosphine is 0.08 g) and sodium tert-butoxide (1.2 g) were added to a three-necked flask, heated to 30°C for reaction for 4 hours, then heated to 60°C for reaction for 8 hours, cooled to room temperature, separated by 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, and eluted with petroleum ether: dichloromethane: tetrahydrofuran = 10:1:1 (volume ratio) to obtain compound P1 (5.6 g).

[0113] The mass spectrometry detection of compound P1: the mass-to-charge ratio (m / z) was measured to be 639.24.

[0114] Synthesis Example 2-11

[0115] Synthesis Examples 2-11 provide a compound and a synthesis method thereof, respectively. The synthesis method of the corresponding compound refers to the preparation method of compound P1, and the corresponding raw material 1 and raw material 2 are reacted (as shown in Table 1 below) to prepare the corresponding compound, and the mass spectrum of the prepared compound is measured to record m / z, as shown in Table 1 below:

[0116] Table 1

[0117]

[0118]

[0119]

[0120] The specific structures of some compounds used in the following application examples and comparative application examples are as follows:

[0121]

[0122]

[0123]

[0124] Application Example 1

[0125] This application example provides a blue light organic electroluminescent device, using the compound P1 provided by the present invention as a main material of the light-emitting layer, and the structure of the blue light organic electroluminescent device is:

[0126] ITO / HT-1: HI-2 [5%] (80nm) / HT-1 (30nm) / EB-1 (20nm) / host material: PBD-1 [5%] (35nm) / ETL-1 (25nm) / LiF (0.5nm) / Al (150nm).

[0127] The preparation method of the blue light organic electroluminescent device is as follows:

[0128] The material was placed in a vacuum chamber and evacuated to 1×10 -5 ~1×10 -6 Pa, vacuum evaporating the above materials onto the cleaned ITO substrate in sequence to prepare an OLED device.

[0129] Among them, PBD-1[5%] refers to the doping ratio of the dye, that is, the volume ratio of the main 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 and the P-type dopant HI-2 is 95:5, and HT-1 is a hole transport material; HT-1:HI-2[5%] is used as a hole injection layer material, and EB-1 is an electron blocking layer material.

[0130] Application Example 2-5

[0131] Application Examples 2-5 each provide a blue light organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced with other compounds (see Table 2 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0132] Comparative Application Example 1-2

[0133] Comparative Application Example 1-2 provides an organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced by other compounds (see Table 2 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0134] Performance Testing

[0135] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the current efficiency is the brightness of 1000cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density, where the driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 2 below:

[0136] Table 2

[0137] Main material dye <![CDATA[Luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT95 Application Example 1 Compound P1 PBD-1 1000 0.96 1.09 1.23 Application Example 2 Compound P2 PBD-1 1000 0.98 1.03 1.11 Application Example 3 Compound P3 PBD-1 1000 0.87 1.38 1.03 Application Example 4 Compound P6 PBD-1 1000 0.99 1.08 1.67 Comparative application example 1 Compound D1 PBD-1 1000 1 1 1 Comparative Application Example 2 Compound D2 PBD-1 1000 1.09 1.06 0.78

[0138] Compared with the compounds D1 and D2 used in comparative application examples 1-2, the compounds P1-P4 used in application examples 1-4 have two carbazole groups connected to the triazine ring by their N atoms, and only one of the two carbazole groups is substituted by two substituent groups (phenyl groups), so that the electron cloud density of the two carbazole groups connected to the triazine ring by the N atoms of compounds P1-P3 is different, which changes the polarity of the molecule accordingly, makes the film-forming property of the material better, and improves the performance of the material. Compound P4, in which the two substituents of the carbazole are connected to the same benzene ring constituting the carbazole ring, has a better life span of the prepared organic electroluminescent device.

[0139] Application Examples 5-6

[0140] Application Examples 5-6 each provide a blue light organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced with other compounds (see Table 3 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0141] Comparative Application Example 3-4

[0142] Comparative Application Example 3-4 provides an organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced by other compounds (see Table 3 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0143] Performance Testing

[0144] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the current efficiency is the brightness of 1000cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density, where the driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 3 below:

[0145] Table 3

[0146] Main material dye <![CDATA[Luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT95 Application Example 5 Compound P4 PBD-1 1000 0.96 1.09 1.31 Application Example 6 Compound P5 PBD-1 1000 1.01 1.07 1.88 Comparative Application Example 3 Compound D3 PBD-1 1000 1 1 1 Comparative Application Example 4 Compound D4 PBD-1 1000 1.11 1.02 1.12

[0147] Compared with the compounds D3 and D4 used in comparative application examples 3-4, the compounds P4-P5 used in application examples 5-6 have two carbazole groups connected to the triazine ring by their N atoms, and only one of the two carbazole groups is substituted by two (three) substituent groups (phenyl groups), so that the electron cloud density of the two carbazole groups connected to the triazine ring by the N atoms of the compounds P4-P5 is different, which changes the polarity of the molecule accordingly, makes the film-forming property of the material better, and improves the performance of the material. The organic electroluminescent device prepared by compound P5 has a greatly increased lifespan.

[0148] Application Examples 7-8

[0149] Application Examples 7-8 each provide a blue light organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced with other compounds (see Table 4 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0150] Comparative Application Examples 5-6

[0151] Comparative Application Example 5-6 provides an organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced by other compounds (see Table 4 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0152] Performance Testing

[0153] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the current efficiency is the brightness of 1000cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density, where the driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 4 below:

[0154] Table 4

[0155] Main material dye <![CDATA[Luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT95 Application Example 7 Compound P7 PBD-1 1000 0.98 1.05 1.11 Application Example 8 Compound P9 PBD-1 1000 1.02 1.08 1.26 Comparative Application Example 5 Compound D3 PBD-1 1000 1 1 1 Comparative Application Example 6 Compound D6 PBD-1 1000 1.02 1.03 0.98

[0156] Compared with compounds D3 and D6 used in comparative application examples 5-6, compounds P7 and P9 used in application examples 7-8 have two carbazole groups whose N atoms are involved in connecting to the triazine ring, and only one of the two carbazole groups is substituted by two substituents (phenyl groups), and the two substituents of the carbazole are connected to the same benzene ring constituting the carbazole ring, and the overall performance of the prepared organic electroluminescent device is better.

[0157] Application Example 9

[0158] Application Example 9 provides a blue light organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced by other compounds (see Table 5 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0159] Comparative Application Examples 5-6

[0160] Comparative Application Example 5-6 provides an organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced by other compounds (see Table 5 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0161] Performance Testing

[0162] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the current efficiency is the brightness of 1000cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density, where the driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 5 below:

[0163] Table 5

[0164] Main material dye <![CDATA[Luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT95 Application Example 9 Compound P8 PBD-1 1000 0.92 1.09 1.74 Comparative Application Example 7 Compound D7 PBD-1 1000 1 1 1 Comparative Application Example 8 Compound D8 PBD-1 1000 0.98 1.02 1.03

[0165] Compared with compounds D7 and D8 used in comparative application examples 7-8, compound P8 used in application examples 7-8 has two carbazole groups whose N atoms are involved in connecting to the triazine ring, and only one of the two carbazole groups is substituted by two substituents (phenyl groups), and the two substituents of the carbazole are connected to the same benzene ring constituting the carbazole ring, so the overall performance of the prepared organic electroluminescent device is better.

[0166] Application Examples 10-11

[0167] Application Examples 10-11 respectively provide a blue light organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced with other compounds (see Table 6 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0168] Comparative Application Example 9

[0169] Comparative Application Example 9 provides an organic electroluminescent device, which differs from Application Example 1 only in that the main material compound P1 of the light-emitting layer is replaced by other compounds (see Table 6 below for details), and the other preparation steps and conditions are the same as those of Application Example 1.

[0170] Performance Testing

[0171] The brightness, driving voltage, current efficiency and LT95 of the organic electroluminescent device provided above were tested, wherein the current efficiency is the brightness of 1000cd / m 2 The corresponding value, LT95, refers to maintaining the initial current density of the device at 10mA / cm 2 The time required for the device efficiency to drop to 95% of the efficiency corresponding to the initial current density, where the driving voltage, current efficiency and LT95 are relative values. The specific test results are shown in Table 6 below:

[0172] Table 6

[0173] Main material dye <![CDATA[Luminance / (cd / m 2 )]]> Driving voltage Current efficiency LT95 Application Example 10 Compound P10 PBD-1 1000 0.98 1.06 1.17 Application Example 11 Compound P11 PBD-1 1000 0.80 1.02 1.08 Comparative Application Example 9 Compound D9 PBD-1 1000 1 1 1

[0174] Compared with the compound D9 used in comparative application example 9, the compound P10 used in application example 10 has a tetraphenylsilane group connected to the triazine ring, and the overall performance of the prepared organic electroluminescent device is better.

[0175] The present invention designs the structure of triazine compounds containing carbazole substituents to prepare triazine compounds containing carbazole substituents with excellent performance. The triazine compounds containing carbazole substituents are used as materials for light-emitting layers, and the prepared organic electroluminescent device has high current efficiency, long life and low driving voltage.

[0176] The applicant declares that the present invention illustrates the detailed process flow of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed process flow, that is, it does not mean that the present invention must rely on the above-mentioned detailed process flow to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A triazine compound containing a carbazole substituent, characterized in that: The triazine compound containing a carbazole substituent has a structure shown in the following formula I: Wherein, Ar is selected from any one or a combination of at least two of phenylene, naphthylene, biphenylene, triphenylene, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl or dibenzothiophenylene; Dashed lines indicate single bonds or their absence; n is selected from 0 or 1; R1-R8 are each independently selected from one of H, phenyl, naphthyl, biphenyl, triphenylene, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl, and at least two of R1-R8 are not selected from H; When R3 and R6 are both selected from phenyl, R1, R2, R4, R5, R7, and R8 are selected from H, n is selected from 0; When R2 and R7 are both selected from phenyl, R1, R3, R4, R5, R6, and R8 are selected from H, n is selected from 0; When one of R1-R8 is selected from carbazolyl, n is selected from 1; The hydrogen atoms in the compound of formula I may be independently substituted by at least one of a deuterium atom, -F, -CN, a C1-C12 alkyl group, a C1-C12 alkoxy group, a triphenylsilyl group, a triphenylmethyl group, a C6-C20 heteroaryl group, and a fluorenyl group; The triazine compounds containing carbazole substituents do not include the following compounds:

2. The triazine compound containing a carbazole substituent according to claim 1, characterized in that: The C1-C12 alkyl group is selected from any one of methyl, ethyl, propyl, butyl, pentyl, methylcyclopentyl, hexyl, methylcyclohexyl, heptyl, octyl or adamantyl, bicyclo[2.2.1]heptyl or bicyclo[2.2.2]octyl; Preferably, the C1-C12 alkoxy group is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentyloxy or hexyloxy; Preferably, the C6-C20 heteroaryl group is selected from any one of a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group.

3. The triazine compound containing a carbazole substituent according to claim 1 or 2, characterized in that: The n is selected from 0, and the Ar is selected from any one of phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl or 9,9-dimethylfluorenyl.

4. The triazine compound containing a carbazole substituent according to any one of claims 1 to 3, characterized in that: The n is selected from 1, and the Ar is selected from any one of phenylene, naphthylene or biphenylene, preferably phenylene.

5. The triazine compound containing a carbazole substituent according to any one of claims 1 to 4, characterized in that: The hydrogen atoms in the compound of formula I can be independently replaced by at least one of a deuterium atom (D), -F, -CN, a methoxy group, an ethoxy group, a propoxy group, a methyl group, an ethyl group, a propyl group, a tert-butyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, and a triphenylsilyl group; Preferably, the hydrogen atoms in the compound of formula I can be replaced independently by any one of a deuterium atom (D), -F, -CN, a methyl group, an ethyl group, a tert-butyl group or a methoxy group.

6. The triazine compound containing a carbazole substituent according to any one of claims 1 to 5, characterized in that: The triazine compound containing a carbazole substituent is selected from any one of the following substituted or unsubstituted compounds: The substitution means that the hydrogen atoms in the triazine compound containing the carbazole substituent can be independently replaced by deuterium atoms.

7. The triazine compound containing a carbazole substituent according to any one of claims 1 to 6, characterized in that: The triazine compound containing a carbazole substituent is selected from any one of the following compounds:

8. 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 compound containing a carbazole substituent as claimed in any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic thin film layer comprises a light-emitting layer, and the main material of the light-emitting layer comprises the triazine compound containing a carbazole substituent according to any one of claims 1 to 7; Preferably, the light-emitting layer is a phosphorescent light-emitting layer.

10. The organic electroluminescent device according to claim 8 or 9, characterized in that: The organic electroluminescent device is a blue light organic electroluminescent device.

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