A compound with triazine derivative as core and application thereof

Abstract

The application discloses a compound taking triazine derivatives as a core and an application thereof, and belongs to the technical field of semiconductors. The structure of the compound provided by the application is shown in general formula (1). The compound provided by the application contains a triazine parent nucleus structure, has suitable HOMO and LUMO energy levels, and has a high triplet energy level (T1). When the compound is applied to an OLED device, the driving voltage of the device can be effectively reduced, and the current efficiency and service life of the device are improved.

Description

Technical Field

[0001] This invention relates to the field of semiconductor technology, and in particular to a compound based on a triazine derivative and its applications. Background Technology

[0002] Organic light-emitting diodes (OLEDs) include an anode, a cathode, and an organic functional layer disposed between the anode and cathode. The organic functional layer is the collective term for all layers between the cathode and anode. The organic functional layer includes a light-emitting layer. Hole transport regions may exist between the anode and the light-emitting layer, and electron transport regions may exist between the light-emitting layer and the cathode. Holes from the anode can migrate to the light-emitting layer through the hole transport regions, and electrons from the cathode can migrate to the light-emitting layer through the electron transport regions. Charge carriers (holes and electrons) recombine in the light-emitting layer to generate excitons. When the excitons transition from the excited state to the ground state, light is emitted.

[0003] Factors affecting the efficiency and lifetime of organic electroluminescent devices include: i) whether the electrons and holes in the light-emitting layer are balanced; ii) whether the emission regions in the light-emitting layer are widely and uniformly distributed in the light-emitting layer, rather than focusing on the hole transport layer or the electron transport layer.

[0004] The light-emitting layer typically comprises a host material and doped materials. The host material primarily serves as the energy transfer component. When only one type of material is used as the host in the light-emitting layer, not all of the two factors listed above can be satisfied. However, all of the conditions listed above can be satisfied if the following conditions are met: a) at least two different types of materials are used as the host, and b) the substituents of the at least two different types of materials have different characteristics.

[0005] Therefore, when the light-emitting layer includes (a) a biased electron host and a biased hole host, and (b) when the biased electron host includes an electron transport group and the biased hole host includes a hole transport group, the organic electroluminescent device can have improved efficiency and increased lifetime.

[0006] According to existing technologies, carbazole derivatives are typically used as hole-type host materials for phosphorescent doping, while triazine derivatives are typically used as electron-type host materials for phosphorescent doping. The performance of the electron-type host material has a significant impact on the aforementioned key performance characteristics of organic electroluminescent devices. There is a need to improve existing electron-type host materials in terms of device voltage, efficiency, and especially device lifetime. For phosphorescent OLEDs, using a single host material in the emitting layer often leads to an imbalance between holes and electrons, resulting in severe efficiency roll-off and shortened lifetime at high current densities. Summary of the Invention

[0007] To address the problems existing in the prior art, this invention provides a compound with a triazine derivative as its core. The compound of this invention uses a triazine substituted with a dibenzofuran or carbazole substituent as an acceptor and a carbazole derivative as a donor. Furthermore, the acceptor and aryl group are simultaneously attached to one side of the carbazole group. When applied to OLED devices, this can effectively improve the high-temperature lifetime of OLED devices and reduce efficiency roll-off.

[0008] The technical solution of this invention is as follows:

[0009] A compound with a triazine derivative as its core, the structure of which is shown in general formula (1):

[0010]

[0011] In general formula (1), R1 and R2 are independently represented as phenyl or biphenyl, respectively;

[0012] X1 to X4 are each independently represented as N atoms or C-(R4);

[0013] Each occurrence of Z1 is independently represented as either C-(H) or C-(D);

[0014] The Ar1 is represented by the structure shown in general formula (2):

[0015]

[0016] In general formula (2), X represents O or N; Z2 is represented independently as C-(R5) each time it appears;

[0017] When X is represented as N, general formula (2) is connected to general formula (1) through X;

[0018] When X is represented as O, general formula (2) is connected to general formula (1) through Z2;

[0019] R3 to R5 are independently represented as hydrogen atom, deuterium atom, cyano group, halogen, substituted or unsubstituted C1-C atom, respectively. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0020] The substituents of the aforementioned "substituted or unsubstituted" groups may be selected from: deuterium, cyano, halogen, C1-C. 20 Alkyl, C2-C 20 alkenyl, C6-C 30 Aryl, C2-C 30 One or more of the heteroaryl groups;

[0021] The heteroatom in the heteroaryl group is selected from one or more of oxygen, sulfur, and nitrogen atoms.

[0022] In a preferred embodiment, the structure of the compound is shown in general formula (1-1) or general formula (1-2):

[0023]

[0024] In general formulas (1-1) and (1-2), the definitions of R1, R2, R3, Z1, Z2, and X1-X4 are the same as those in the above description.

[0025] In a preferred embodiment, the structure of the compound is shown in any one of general formulas (3-1) to (3-6):

[0026]

[0027]

[0028] In general formulas (3-1) to (3-6), the definitions of R1, R2, R3, X1 to X4, Z1, and Z2 are the same as those in the above description.

[0029] In a preferred embodiment, the structure of the compound is shown in general formula (4-1) or general formula (4-2):

[0030]

[0031] In general formulas (4-1) and (4-2), the definitions of X1 to X4, Z1, Z2, and R3 are the same as those in claim 1.

[0032] Further preferably, R3 to R5 are independently represented as hydrogen atom, deuterium atom, cyano group, halogen, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted diphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, etc. One of the following: substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted furanyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl;

[0033] The substituents of the "substituted or unsubstituted" group are selected from one or more of the following: deuterium, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, furanyl, benzofuranyl, and dibenzofuranyl.

[0034] Further preferably, the specific structure of the triazine derivative-based compound is any one of the following compounds:

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041] An organic electroluminescent device includes an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode, and the organic functional layer includes a light-emitting layer, wherein the light-emitting layer includes a host material and a guest material, and the host material contains the compound with the triazine derivative as its core.

[0042] Preferably, the host material comprises the triazine derivative-based compound as a biased electronic host and a heterocyclic compound represented by general formula (5) or general formula (6) as a biased hole-type host:

[0043]

[0044] In general formula (5), L3 and L4 are independently represented as: single bond, substituted or unsubstituted C1-C 10 Alkylene, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0045] a1 and a2 can be independently represented as 1, 2, 3 or 4 respectively;

[0046] b1, b2, b3, b4, b5, and b6 can be independently represented as 1, 2, 3, or 4;

[0047] R7, R 12 C1-C, represented independently as substituted or unsubstituted, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0048] R8~R 11 Each can be independently represented as hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C6-C 30 aryloxy, substituted or unsubstituted C6-C 30 Arylthio, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0049] In general formula (6), L5 and L6 are independently represented as single-bonded, substituted, or unsubstituted C6-C bonds, respectively. 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0050] R 16 R 17 C6-C can be represented independently as substituted or unsubstituted. 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0051] R 12 ~R 15 Each of the following can be independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0052] The substituents of the above groups, whether substituted or unsubstituted, may be selected from: deuterium, halogen, hydroxyl, cyano, nitro, amino, C1-C. 10 Alkyl, C1-C 10 Alkoxy, C3-C 10 cycloalkyl, C6-C 30 Aryl, C6-C 30 Aryloxy group, C6-C 30 Aryl thiols, C2-C 30 Heteroaryl, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5) or -B(Q6)(Q7); wherein Q1 to Q7 are independently represented as hydrogen, C1-C, etc. 10Alkyl, C1-C 10 Alkoxy, C6-C 30 Aryl, C2-C 30 One of the heteroaryl groups.

[0053] Further preferably, in the general formulas (5) and (6), R7~R 17 The following groups, individually represented as substituted or unsubstituted, are: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, phenyl, biphenyl, triphenyl, dicyclopentadienyl, indyl, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl, isoindoleyl, indoleyl, indoleyl, purine, quinolinyl, isoquinolinyl, carbazoleyl, benzo[a]quinolinyl, phthalazinyl, naphthidyl, quin Any one of the following: oxolinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzothiazolyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, pyridinobenzofuranyl, pyrimidinobenzofuranyl, pyridinobenzothiopheneyl, pyrimidinobenzothiopheneyl, thianyl, phenoxthiazolyl, and dibenzodioxaneyl;

[0054] L3 to L6 are independently represented as single bond, phenylene, naphthylene, fluorene, phenanthrene, anthracene, benzo[9,10]phenanthrene, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, naphthylene, quinoxalinyl, quinoxalinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, and so on. One of the following: benzimidazolyl, benzofuranyl, benzothiophene, triazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, imidazopyridyl, imidazopyrimidinyl, pyridinobenzofuranyl, pyrimidobenzofuranyl, pyridinobenzothiophene, pyrimidobenzothiophene, pyrimidobenzothiophene, pyrimidobenzothiophene, pyrimidoxathiyl, and dibenzodioxaneyl;

[0055] The substituents of the above groups, whether substituted or unsubstituted, are selected from: deuterium, F, Cl, Br, I, hydroxyl, cyano, nitro, amino, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, phenyl, biphenyl, cyclopentadienyl, indole, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, iso[a]pyridyl, pyrazinyl, pyrid ... Indole, indole, indazole, purine, quinolinyl, isoquinolinyl, carbazole, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, carbazole, phenanthridine, acridineyl, phenanthridine, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzothiazolyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole.

[0056] More preferably, the compound serving as the partial cavitation host is selected from one or more of the following structures:

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064] Preferably, the weight ratio between the compound that is the electron-biased host and the compound that is the hole-biased host is 1:10 to 10:1; more preferably, it is 1:9 to 9:1; more preferably, it is 2:8 to 8:2; and even more preferably, it is 3:7 to 7:3.

[0065] An illumination or display element comprising the aforementioned organic electroluminescent device.

[0066] By selecting a reasonable dual-substrate combination, this invention can achieve a suitable balance between electron transport and hole transport in the light-emitting layer, thereby effectively improving the efficiency and lifespan of OLED devices.

[0067] The organic electroluminescent device of the present invention can be applied to lighting or display elements, which greatly improves the current efficiency, power efficiency and external quantum efficiency of the device; at the same time, it significantly improves the device lifetime and has good application effect in OLED light-emitting devices, and has good industrialization prospects.

[0068] The beneficial effects of this invention are:

[0069] The compounds of this invention exhibit strong molecular asymmetry, resulting in high Tg. In the compounds provided by this invention, the combination of triazine groups and phenyl-substituted carbazole groups helps to further improve the aggregation morphology of the material, effectively enhancing the high-temperature stability of the device.

[0070] The compounds of this invention have large steric hindrance within their molecules, large molecular volume, and weak intermolecular interactions. Therefore, the compounds of this invention have the characteristics of being difficult to crystallize, having a low vapor deposition temperature, and good film-forming properties, which can effectively improve industrial processing performance.

[0071] The triazine group and phenyl-substituted carbazole group in the compound provided by this invention ensure that the material has strong electron injection and transport capabilities. When applied to the main material of the light-emitting layer, it helps to significantly reduce the driving voltage of the device and improve the device efficiency.

[0072] The compounds provided by this invention can be used in combination with hole-type compounds to help further improve efficiency roll-off and device lifespan. Attached Figure Description

[0073] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0074] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a capping layer (CPL layer). Detailed Implementation

[0075] The principles and features of the present invention are described below with reference to the accompanying drawings. The examples given are only for explaining the present invention and are not intended to limit the scope of the present invention.

[0076] Unless otherwise stated, all materials used in the following examples and comparative examples are commercially available or can be obtained by methods known to those skilled in the art.

[0077] Synthesis of intermediates

[0078] Synthesis of intermediate M-1:

[0079]

[0080] (1) In a three-necked flask, under nitrogen protection, add 0.012 mol of raw material A1, 0.01 mol of raw material B1, and 150 ml of toluene and stir to mix. Then add 5 × 10⁻⁶ ml of toluene. -5 mol Pd2(dba)3, 5×10 -5 0.03 mol P(t-Bu)3 and 0.03 mol sodium tert-butoxide were heated to 105 °C and refluxed for 24 hours. A sample was spotted onto a TLC plate to confirm complete reaction. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was rotary evaporated until no fraction remained. The filtrate was then passed through a neutral silica gel column to obtain intermediate a1. LC-MS: Measured value: 398.18 ([M+H)) + Precision quality: 397.05.

[0081] (2) In a three-necked flask, under nitrogen protection, 0.003 mol of intermediate a1, 0.006 mol of pinacol diboronate, 0.009 mol of potassium acetate, and 6 × 10⁻⁶ mol of sodium hydroxide were added. -4 mol of S-phos, 1.2 × 10⁻⁶ -4 mol of Pd₂(dba)₃ was added to 150 mL of dioxane, and the mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, and purified by silica gel column chromatography using n-heptane / ethyl acetate (9:1) as the eluent to give intermediate M-1. LC-MS: Measured value: 446.35 ([M+H)₂) + ), Precision quality: 445.22.

[0082] Synthesis of intermediate M-2:

[0083]

[0084] (1) In a three-necked flask, under nitrogen protection, add 0.012 mol of raw material A1, 0.01 mol of raw material B2, and 150 ml of toluene and stir to mix. Then add 5 × 10⁻⁶ ml of toluene. -5 mol Pd2(dba)3, 5×10 -5 0.03 mol P(t-Bu)3 and 0.03 mol sodium tert-butoxide were heated to 105 °C and refluxed for 24 hours. A sample was spotted onto a TLC plate to confirm complete reaction. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was rotary evaporated until no fraction remained. The filtrate was then passed through a neutral silica gel column to obtain intermediate a2. LC-MS: Measured value: 356.13 ([M+H)) + Precision quality: 354.98.

[0085] (2) In a three-necked flask, under nitrogen protection, add 0.01 mol of intermediate a2 and 0.012 mol of raw material C2, dissolve them in a mixed solvent (90 ml toluene, 45 ml ethanol), and then add 1×10 -4 10 mL of 0.03 mol / L Pd(PPh3)4 and 0.03 mol / L K2CO3 aqueous solution were added and heated under reflux for 15 hours. A sample was spotted onto a TLC plate to confirm complete reaction. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was rotary evaporated until no fraction remained. The filtrate was then passed through a neutral silica gel column to obtain intermediate b2. LC-MS: Measured value: 430.41 ([M+H) + Precision mass: 429.13.

[0086] (3) In a three-necked flask, under nitrogen protection, 0.003 mol of intermediate b2, 0.006 mol of pinacol diboronate, 0.009 mol of potassium acetate, and 6 × 10⁻⁶ mol of sodium hydroxide were added. -4 mol of S-phos, 1.2 × 10⁻⁶ -4 mol of Pd₂(dba)₃ was added to 150 mL of dioxane, and the mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, and purified by silica gel column chromatography using n-heptane / ethyl acetate (9:1) as the eluent to give intermediate M-2. LC-MS: Measured value: 522.36 ([M+H)₂) + Precision quality: 521.25.

[0087] The following intermediates were synthesized following the same preparation process as intermediate M-1, except that the reaction conditions were the same, except that the raw materials A, B and intermediate a listed in Table 1 were used.

[0088] Table 1

[0089]

[0090]

[0091] Compound Synthesis

[0092] Example 1: Preparation of compound 4:

[0093]

[0094] In a three-necked flask, under nitrogen protection, add 0.012 mol of raw material D1 and 0.01 mol of intermediate M-1, dissolve them in a mixed solvent (90 ml toluene, 45 ml ethanol), and then add 1 × 10⁻⁶ mol of the solvent. -410 mL of 0.03 mol / L K2CO3 aqueous solution was added to mol Pd(PPh3)4 and heated under reflux for 15 hours. A sample was taken and spotted onto a TLC plate to confirm the completeness of the reaction. The mixture was allowed to cool naturally to room temperature, filtered, and the filtrate was rotary evaporated until no fraction remained. The filtrate was then passed through a neutral silica gel column to obtain compound 4.

[0095] The following target compounds were synthesized according to the preparation process in Example 1; the reaction conditions were the same, except that the starting material D and intermediate M listed in Table 2 below were used.

[0096] Table 2

[0097]

[0098]

[0099]

[0100] Characterization data of the compounds in the above embodiments of the present invention are shown in Table 3:

[0101] Table 3

[0102]

[0103] The compounds of this invention, when used in light-emitting devices, exhibit high glass transition temperature (Tg) and triplet energy level (T1), suitable HOMO and LUMO energy levels, high electron mobility, short delayed fluorescence lifetime, and high fluorescence quantum yield, making them suitable as host materials for the emitting layer. The compounds prepared in the above embodiments of this invention were tested for thermal properties, T1 energy level, HOMO / LUMO energy level, and single-charge device characteristics. The results are shown in Table 4.

[0104] Table 4

[0105]

[0106] Note: The triplet energy level T1 was measured using a Hitachi F4600 fluorescence spectrometer, and the material was tested under 2*10⁻⁶ conditions. - 5 The solution was a mol / L toluene solution; the glass transition temperature Tg was determined by differential scanning calorimetry (DSC, Netzsch DSC204F1 differential scanning calorimeter, Germany) at a heating rate of 10 °C / min; the highest occupied molecular orbital (HOMO) energy level was measured by an ionization energy testing system (IPS-3) under atmospheric conditions; the lowest unoccupied molecular orbital (LUMO) energy level was obtained by subtracting Eg from the HOMO energy level, and Eg was calculated from the tangent at the maximum absorption wavelength of the ultraviolet absorption curve of the single film; the electron mobility was determined by fabricating the material into a single-charge device and measuring it using the SCLC method.

[0107] As can be seen from the data in the table above, the organic compounds of the present invention have high glass transition temperatures, which can improve the film phase stability and high-temperature stability of the material; the organic compounds of the present invention have suitable HOMO and LUMO energy levels and a high T1 energy level, which can be used as host materials; unexpectedly, compared with the comparative compounds, the compounds of the present invention not only have higher electron mobility, but also have shorter delayed fluorescence lifetime and higher fluorescence quantum yield.

[0108] The following detailed description of the application effects of the OLED material synthesized in the present invention in devices is provided through device embodiments and device comparison examples.

[0109] The device embodiments 2-12 and device comparative examples 1-4 of the present invention have the same manufacturing process as device embodiment 1, and use the same substrate material and electrode material. The film thickness of the electrode material is also consistent. The only difference is that the light-emitting layer material in the device is replaced.

[0110] Device Example 1

[0111] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film. The anode layer 2 (ITO (15nm) / Ag (150nm) / ITO (15nm)) is washed sequentially with a cleaning agent (SemiClean M-L20), pure water, and dried, followed by ultraviolet-ozone washing to remove organic residues from the anode layer surface. After the above washing, a 10nm thick layer of HT23 and NDP is deposited on the anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT23 to NDP of 97:3. Next, a 130nm thick layer of HT23 is deposited as a hole transport layer 4. Subsequently, a 40nm thick layer of EB6 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated. Its structure includes compound 4 as the host material and EMD-13 as a dopant material, with a mass ratio of compound 4 to EMD-13 of 94:6, and a light-emitting layer thickness of 40nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. After the hole-blocking layer 7, ET1 and Liq are deposited in a 1:1 mass ratio. The vacuum-deposited film of this material has a thickness of 35 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a 1 nm thick Yb layer is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, a 15 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus; the Mg:Ag mass ratio is 1:9; this layer serves as the cathode layer 10. On the cathode layer 10, CP-1 is vacuum-deposited as the CPL layer 11, with a thickness of 70 nm. This yields the organic electroluminescent device 1.

[0112] The device embodiments 14-30 and device comparative examples 5-8 of the present invention have the same manufacturing process as device embodiment 13, and use the same substrate material and electrode material. The film thickness of the electrode material is also kept consistent. The only difference is that the light-emitting layer material or its proportion in the device is changed.

[0113] Device Example 13

[0114] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film. The anode layer 2 (ITO (15nm) / Ag (150nm) / ITO (15nm)) is washed sequentially with a cleaning agent (SemiClean M-L20), pure water, and dried, followed by ultraviolet-ozone washing to remove organic residues from the anode layer surface. After the above washing, a 10nm thick layer of HT23 and NDP is deposited on the anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT23 to NDP of 97:3. Next, a 130nm thick layer of HT23 is deposited as a hole transport layer 4. Finally, a 40nm thick layer of EB6 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the emitting layer 6 of the OLED light-emitting device is fabricated. Its structure includes compound 4 and compound 12A as the main materials, and EMD-13 as the dopant material. The mass ratio of compound 4, compound 12A, and EMD-13 is 50:50:6, and the thickness of the emitting layer is 40 nm. Following the emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole blocking layer 7. After the hole blocking layer 7, ET1 and Liq are deposited, with a mass ratio of ET1 to Liq of 1:1. The vacuum-deposited film thickness of this material is 35 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a 1 nm thick Yb layer is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, a 15 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus; the mass ratio of Mg to Ag is 1:9; this layer serves as the cathode layer 10. On the cathode layer 9, CP-1 is vacuum-deposited as the CPL layer 11 with a thickness of 70 nm. Organic electroluminescent device 21 is obtained.

[0115] The preparation methods of devices in Examples 14-24 are similar to those in Example 13. The difference lies in that the main material of the light-emitting layer is replaced with other compounds used in this invention.

[0116] The fabrication methods for devices in Examples 25-30 are similar to those in Example 13. The difference lies in the use of different proportions of the light-emitting layer material shown in Table 5 below.

[0117] The fabrication methods of Comparative Examples 5-8 are similar to those of Device Example 13. The difference lies in the main material of the light-emitting layer.

[0118] The structural formulas of the materials involved in the fabrication of the above devices are as follows:

[0119]

[0120]

[0121] Materials and reagents used in the examples:

[0122] ITO / Ag anode layer + transparent PI film: Kunshan Visionox Technology Co., Ltd.

[0123] Cleaning agent: SemiClean M-L20

[0124] Vacuum evaporation equipment: Choshu Sangyo Co., Ltd., Japan

[0125] The aforementioned cavitation host compounds 9A to 206A (numbered out of sequence) can be synthesized according to methods known to those skilled in the art, such as those described in patent applications with application numbers JP3139321B2, KR1020150141047A, US20150236262A1, US20160133853A1, US20170186969A1, and CN107528004A, which are incorporated herein by reference, for the preparation of cavitation host materials: 12A, 22A, 142A, and 206A.

[0126] The aforementioned partial cavitation host compounds 1B to 248B (numbered out of sequence) can be synthesized according to methods known to those skilled in the art, such as those described in patent applications with application numbers TW201930299A, CN111247226A or CN105916847A, which are incorporated herein by reference, to prepare partial cavitation host material: 227B.

[0127] The aforementioned ref-1, ref-2, ref-3, and ref-4 can be synthesized according to methods known to those skilled in the art, such as those described in patent applications with application numbers KR1020200025939A, KR1020180068882A, CN111620853A, and KR1020200125080A, which are incorporated herein by reference. The prior art materials are: ref-1, ref-2, ref-3, and ref-4.

[0128] Examples and comparisons of devices prepared using the same method are shown in Table 5; the test results of voltage, current efficiency, color and lifetime of the obtained devices are shown in Table 6.

[0129] Table 5

[0130]

[0131]

[0132]

[0133] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit. The voltage, current efficiency, emission spectrum, and lifetime of the device are measured. The obtained device's voltage, current efficiency, color, and 20mA / cm² performance are also measured. 2 The test results for the LT95 lifetime are shown in Table 6. For the above-mentioned light-emitting devices, voltage, current efficiency, and color coordinates were measured at a current density of 10 mA / cm². 2 The test was conducted under the following conditions using an IVL (current-voltage-brightness) testing system (Suzhou Fosstar Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Co., Ltd., Japan; LT95 refers to the condition at 20mA / cm². 2 Under these conditions, the time it takes for the device's brightness to decay to 95% is considered high-temperature lifetime. High-temperature lifetime refers to the time it takes for the device to maintain a brightness of 20 mA / cm² at 85°C. 2 Under certain conditions, the time it takes for the device brightness to decay to 95% of its original brightness.

[0134] Table 6

[0135]

[0136]

[0137] The results shown in Table 6 indicate that, compared to the comparative devices, the driving voltage of the devices is significantly reduced and the current efficiency is improved when the compounds of the present invention are used in the light-emitting layer, whether as a single host or a dual host material; in particular, the device lifetime and high-temperature lifetime are significantly improved. Furthermore, compared to the single-host devices of Examples 1-12, the organic electroluminescent devices 13-30 obtained by using a combination of two host compounds in the light-emitting layer according to the present invention show a significant improvement in current efficiency and lifetime.

[0138] To compare the efficiency degradation of different devices under high current density, an efficiency degradation coefficient for each device was defined. Where μ m Expressed as the maximum current efficiency of the device, μ 50 This indicates a drive current of 50mA / cm.2 The current efficiency of the device. A higher value indicates a more severe efficiency roll-off in the device; conversely, a lower value indicates that the rapid degradation of the device under high current density has been controlled. This invention measured the efficiency degradation coefficients of devices obtained in Device Examples 1-30 and Comparative Examples 1-8. The results are shown in Table 7:

[0139] Table 7

[0140]

[0141]

[0142] The results shown in Table 7 demonstrate that, by comparing the efficiency decay coefficients of the examples and comparative examples, we can see that the organic light-emitting device of the present invention can effectively reduce the efficiency roll-off at high current densities.

[0143] Based on the above, this invention achieves unexpected technical results in terms of driving voltage, current efficiency, and lifetime by selecting two host compounds with specific properties as host materials to prepare the light-emitting layer.

[0144] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not intended to limit it. Modifications or equivalent substitutions made by those skilled in the art to the technical solutions of the present invention without departing from the spirit and scope of the present invention should be covered within the scope of the claims of the present invention.

Claims

1. A compound with a triazine derivative as its core, characterized in that, The structure of the compound is shown in any one of general formulas (3-1) to (3-4): In general formulas (3-1) to (3-4), R1 represents phenyl; R2 represents phenyl; X1~X4 are each independently represented as C-(R4); Each occurrence of Z1 is independently represented as either C-(H) or C-(D); Each occurrence of Z2 is independently represented as C-(R5); R3 represents one of hydrogen atom, deuterium atom, or phenyl; R4 represents either a hydrogen atom or a deuterium atom; R5 represents either a hydrogen atom or a deuterium atom.

2. The compound based on a triazine derivative according to claim 1, characterized in that, The specific structure of the compound is any one of the following compounds: (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (29) (30) (31) (32) (33) (34) (35) (36) (38) (40) (41) (45) (53) (61) (62) (63) (64) (65) (66) (67) (68) (69) (70) (71) (72) (73) (81) (82) (83) (84) (85) (86) (87) (88) (89) (90) (91) (92) (93)。 3. A compound with a triazine derivative as its core, characterized in that, The specific structure of the compound is as follows: (28)。 4. An organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode, and the organic functional layer includes a light-emitting layer, characterized in that, The light-emitting layer comprises a host material and a guest material, wherein the host material contains a compound based on a triazine derivative as described in any one of claims 1 to 3.

5. The organic electroluminescent device according to claim 4, characterized in that, The host material comprises a triazine derivative-based compound as a biased electronic host and a heterocyclic compound represented by general formula (5) or general formula (6) as a biased hole host: In general formula (5), L3 and L4 are independently represented as: single bond, substituted or unsubstituted C1-C 10 Alkylene, substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; a1 and a2 can be independently represented as 1, 2, 3 or 4 respectively; b1, b2, b3, b4, b5, and b6 can be independently represented as 1, 2, 3, or 4; R7, R 12 C1-C, represented independently as substituted or unsubstituted, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R8~R 11 Each can be independently represented as hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amino, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C6-C 30 aryloxy, substituted or unsubstituted C6-C 30 Arylthio, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; In general formula (6), L5 and L6 are independently represented as single bond, substituted or unsubstituted C6-C bonds, respectively. 30 aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R 16 R 17 C6-C can be represented independently as substituted or unsubstituted. 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R 12 ~R 15 Each of the following can be independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents of the above groups, whether substituted or unsubstituted, may be selected from: deuterium, halogen, hydroxyl, cyano, nitro, amino, C1-C. 10 Alkyl, C1-C 10 Alkoxy, C3-C 10 cycloalkyl, C6-C 30 Aryl, C6-C 30 Aryloxy group, C6-C 30 Aryl thiols, C2-C 30 Heteroaryl, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5) or -B(Q6)(Q7); wherein Q1~Q7 are independently represented as hydrogen, C1-C, etc. 10 Alkyl, C1-C 10 Alkoxy, C6-C 30 Aryl, C2-C 30 One of the heteroaryl groups.

6. The organic electroluminescent device according to claim 5, characterized in that, In the general formulas (5) and (6), R7~R 17 The following groups, individually or independently, are represented as substituted or unsubstituted: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, phenyl, biphenyl, triphenyl, dicyclopentadienyl, indyl, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridinyl, isoindoleyl, indoleyl, indoleyl, purine, quinolinyl, isoquinolinyl, carbazoleyl, benzo[a]quinolinyl, phthalazinyl, naphthidyl, quin Any one of the following: oxolinyl, quinazolinyl, cinolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzothiazolyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, dibenzothiopheneyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, pyridinobenzofuranyl, pyrimidinobenzofuranyl, pyridinobenzothiopheneyl, pyrimidinobenzothiopheneyl, thianyl, phenoxthiazolyl, and dibenzodioxaneyl; L3~L6 are independently represented as single bond, phenylene, naphthylene, fluorene, phenanthrene, anthracene, benzo[9,10]phenanthrene, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, carbazolyl, benzoquinolinyl, naphthylene, quinoxalinyl, quinoxalinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, and so on. One of the following: benzimidazolyl, benzofuranyl, benzothiophene, triazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, imidazopyridyl, imidazopyrimidinyl, pyridinobenzofuranyl, pyrimidobenzofuranyl, pyridinobenzothiophene, pyrimidobenzothiophene, pyrimidobenzothiophene, pyrimidobenzothiophene, pyrimidoxathiyl, and dibenzodioxaneyl; The substituents of the above groups, whether substituted or unsubstituted, are selected from: deuterium, F, Cl, Br, I, hydroxyl, cyano, nitro, amino, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, phenyl, biphenyl, cyclopentadienyl, indole, naphthyl, fluorenyl, spirofluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, iso[a]pyridyl, pyrazinyl, pyrid ... Indole, indole, indazole, purine, quinolinyl, isoquinolinyl, carbazole, benzoquinolinyl, phthalazinyl, naphridinyl, quinoxolinyl, quinazolinyl, cinolinyl, carbazole, phenanthridine, acridineyl, phenanthridine, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophene, benzothiazolyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole.

7. The organic electroluminescent device according to claim 5, characterized in that, The compound serving as the partial cavitation host is selected from one or more of the following structures: (9A) (10A) (11A) (12A) (13A) (14A) (15A) (16A) (17A) (18A) (19A) (20A) (21A) (22A) (23A) (24A) (25A) (26A) (27A) (28A) (29A) (142A) (143A) (144A) (145A) (146A) (147A) (148A) (149A) (150A) (151A) (152A) (206A) 1B 2B 3B 5B 6B 8B 9B 10B 12B 13B 14B 15B 16B 19B 20B 21B 23B 26B 28B 29B 30B 31B 32B 33B 34B 36B 38B 40B 41B 42B 43B 47B 49B 50B 51B 53B 55B 56B 57B 59B 60B 61B 62B 64B 65B 66B 67B 68B 77B 79B 80B 81B 84B 85B 88B 90B 92B 93B 94B 97B 98B 99B 100B 103B 104B 108B 111B 112B 113B 114B 115B 116B 117B 118B 119B 120B 121B 122B 123B 124B 125B 127B 128B 131B 132B 133B 134B 135B 136B 137B 138B 140B 141B 142B 143B 145B 146B 147B 148B 149B 150B 151B 152B 154B 155B 157B 158B 159B 162B 163B 165B 166B 167B 168B 171B 172B 174B 175B 177B 178B 179B 180B 181B 182B 183B 184B 185B 187B 188B 189B 190B 191B 192B 193B 196B 197B 199B 200B 201B 202B 203B 204B 205B 206B 207B 208B 209B 212B 213B 215B 216B 217B 218B 219B 220B 221B 222B 223B 224B 225B 226B 227B 228B 230B 231B 233B 234B 235B 236B 237B 238B 239B 240B 241B 242B 243B 245B 246B 247B 248B; The weight ratio between the compound that is the electron-biased host and the compound that is the hole-biased host is 1:10 to 10:

1.

8. The organic electroluminescent device according to claim 7, characterized in that, The weight ratio between the compound that is the electron-biased host and the compound that is the hole-biased host is 1:9 to 9:

1.

9. The organic electroluminescent device according to claim 7, characterized in that, The weight ratio between the compound that is the electron-biased host and the compound that is the hole-biased host is 2:8 to 8:

2.

10. The organic electroluminescent device according to claim 7, characterized in that, The weight ratio between the compound that is the electron-biased host and the compound that is the hole-biased host is 3:7 to 7:3.

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