Triazine compound, and OLED and organic light-emitting device comprising same
By using triazine compounds in OLED devices, the problem of carrier migration mismatch was solved, resulting in OLED devices with low driving voltage and long lifetime, and improved luminous efficiency and thermal stability.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- YURUI SHANGHAI CHEM
- Filing Date
- 2025-08-14
- Publication Date
- 2026-05-21
AI Technical Summary
The mismatch in carrier migration speed in existing OLED materials leads to a decline in photoelectric performance, high driving voltage, and short display lifespan, which affects the further practical application of the devices.
Using triazine compounds as the core structure, and forming side chains by combining aryl and alkyl groups with fluorenyl groups, it is used as a hole blocking layer or electron transport layer in organic electroluminescent devices to improve carrier migration balance and thermal stability.
This achieves lower driving voltage, improved luminous efficiency and device lifespan, reduced power consumption, and enhanced overall performance of OLED devices.
Smart Images
Figure PCTCN2025114665-FTAPPB-I100001 
Figure PCTCN2025114665-FTAPPB-I100002 
Figure PCTCN2025114665-FTAPPB-I100003
Abstract
Description
A triazine compound, an OLED having the compound, and an organic light-emitting device. Technical Field
[0001] This invention relates to the field of organic optoelectronic material preparation technology, specifically to a triazine compound, an OLED having the compound, and an organic light-emitting device. Background Technology
[0002] Organic light-emitting diodes (OLEDs), also known as organic light-emitting devices, are a technology that converts electrical energy into light energy through organic light-emitting materials. This technology involves applying voltage to an organic light-emitting element to inject holes from the anode and electrons from the cathode into the light-emitting layer. The injected holes and electrons then recombine to form excitons, causing light to be emitted.
[0003] In organic light-emitting diodes (OLEDs), the mismatch between the migration rates of hole and electron carriers in most materials means that the two types of carriers may not recombine in the light-emitting layer. This leads to a decrease in the device's photoelectric performance, increased leakage current, heat generation, and reduced lifespan. Existing materials still have limitations in improving device performance. Even with different combinations of materials, display technology still suffers from high driving voltage and short display lifespan, severely hindering its further practical application.
[0004] Therefore, continuous efforts are needed to develop organic light-emitting devices with low voltage drive, high brightness and long lifespan, and to find suitable OLED optoelectronic functional materials for OLED devices to solve the above problems. Summary of the Invention
[0005] To address the aforementioned technical problems, this invention provides a triazine compound, an OLED comprising the compound, and a display or lighting device. The provided triarylamine compound has a triazine structure as its core, with aryl and alkyl groups combined with fluorenyl groups forming side chains. Therefore, when used in organic electroluminescent devices, this triazine compound enables the device to simultaneously possess high efficiency and a long operating life.
[0006] The triazine compound provided by this invention is achieved through the following technical solution:
[0007] A triazine compound having the structure shown in Formula I:
[0008] In Formula I, R1, R2, R3, and R4 are each independently monosubstituted, disubstituted, or have the maximum number of substitutions; R1 and R2 are each independently selected from hydrogen, deuterium, cyano, cyano-substituted or unsubstituted C6-C30 aryl, C5-C36 heteroaryl; L is independently selected from single bond, deuterated or undeuterated C6-C30 arylene; R3 and R4 are each selected from substituted or unsubstituted C1-C24 alkyl, C3-C20 cycloalkyl; when R3 and R4 contain substitutions, the substituents are selected from one or more of deuterium and C6-C30 aryl, and the structure shown in Formula I can be partially or completely deuterated.
[0009] Preferably, in Formula I, R1 and R2 are each independently selected from hydrogen, deuterium, cyano, cyano-substituted or unsubstituted phenyl, cyano-substituted or unsubstituted naphthyl, cyano-substituted or unsubstituted phenanthyl, cyano-substituted or unsubstituted naphthylphenyl, cyano-substituted or unsubstituted biphenyl, and dibenzofuranyl.
[0010] Preferably, in Formula I, L is independently selected from single bonds, deuterated or undeuterated phenylene, deuterated or undeuterated biphenylene; R3 and R4 are each independently selected from methyl, ethyl, propyl, tert-butyl, pentyl, phenylpropyl, diphenylethyl, phenyl-substituted tert-butyl, and cyclopentyl.
[0011] According to one or more embodiments, the present invention provides a triazine compound selected from any of the following chemical structures, where D represents deuterium:
[0012] The present invention also provides an application of the triazine compound described above in organic electroluminescent devices.
[0013] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising:
[0014] Substrate layer;
[0015] A first electrode is located on the substrate;
[0016] An organic light-emitting functional layer is disposed on the first electrode;
[0017] The second electrode is located on the organic light-emitting functional layer;
[0018] The organic light-emitting functional layer includes triazine compounds as described above.
[0019] Preferably, at least one of the organic light-emitting functional layers is an electron transport layer or a hole blocking layer, and the electron transport layer or hole blocking layer includes triazine compounds as described above.
[0020] The present invention also provides a composition comprising a triazine compound as described in Formula I.
[0021] The present invention also provides a formulation comprising a triazine compound with the structure shown in Formula I above, or a composition as described above, and at least one solvent. The solvent is not particularly limited and may be any solvent well known to those skilled in the art, such as unsaturated hydrocarbon solvents like toluene, xylene, mesitylene, tetrahydronaphthalene, decahydronaphthalene, dicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc.; halogenated unsaturated hydrocarbon solvents like chlorobenzene, dichlorobenzene, trichlorobenzene, etc.; ether solvents like tetrahydrofuran, tetrahydropyran, etc.; and ester solvents like alkyl benzoates.
[0022] The organic electroluminescent device of the present invention can be used in OLED lighting or display devices.
[0023] The present invention also provides a display or lighting device comprising one or more of the organic electroluminescent devices described above.
[0024] In summary, compared with the prior art, the present invention has the following beneficial effects:
[0025] The triazine compounds of the present invention form side chains by combining aryl and alkyl groups with fluorenyl groups, which gives the compounds good thermal stability, excellent luminous efficiency, and good lifespan. At the same time, the triazine compounds provided by the present invention, when used in devices, can effectively enable organic light-emitting devices to have lower driving voltages while maintaining voltage stability, improve luminous efficiency, and achieve better device lifespan. Detailed Implementation
[0026] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of the present invention.
[0027] The aryl group referred to in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic aryl or a fused-ring aryl. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples may include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthracene, phenanthryl, or pyrene, but are not limited thereto. Aryl or aromatic group – as used herein, considers both non-fused and fused systems. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fen, fluorene, pyrene, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylyl, 3,4-dimethylyl, 2,5-dimethylyl, mestriylyl, and m-tetraphenyl.
[0028] The heteroaryl group referred to in this invention is a general term for groups obtained by replacing one or more aromatic nucleus carbons in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, silicon, or nitrogen atoms. The heteroaryl group can be a monocyclic heteroaryl or a fused-ring heteroaryl, and can have 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms. Examples include pyridyl, pyrroleyl, pyridinyl, thiophenyl, furanyl, indolyl, quinolinyl, isoquinolinyl, benzothiophenyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, etc., but are not limited thereto.
[0029] The alkyl groups described in this invention include straight-chain and branched alkyl groups. They can be alkyl groups having 1 to 24 carbon atoms, with preferred alkyl groups containing 1 to 4 carbon atoms, including methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, etc. Furthermore, the alkyl groups may optionally be substituted.
[0030] The cycloalkyl group described in this invention refers to and includes monocyclic, polycyclic, and spiroalkyl groups. Preferred cycloalkyl groups are those containing 3 to 20 ring carbon atoms, more preferably those containing 3 to 12 ring carbon atoms, and particularly preferably those containing 3 to 6 ring carbon atoms, including cyclopropyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, etc. Furthermore, the cycloalkyl group may optionally be substituted.
[0031] Throughout this specification, unless explicitly stated otherwise, the term "including" any component will be understood to imply the inclusion of other components, not to exclude any other components. Furthermore, it should be understood that throughout this specification, when an element such as a layer, film, region, or substrate is referred to as being "on" or "above" another element, it may be "directly on" the other element, or there may be intermediate elements present. Additionally, "on" or "above" means located above the target portion, and not necessarily above it in the direction of gravity.
[0032] One object of the present invention is to provide an electroluminescent device, the organic electroluminescent device comprising: a substrate layer; a first electrode on the substrate; an organic light-emitting functional layer on the first electrode; and a second electrode on the organic light-emitting functional layer; wherein the organic light-emitting functional layer comprises a hole blocking layer and an electron transport layer. In one embodiment of the present invention, the hole blocking layer or the electron transport layer in the organic electroluminescent (OLED) device comprises one or more compounds as shown in the above general formula I.
[0033] In a preferred embodiment of the present invention, an OLED is provided, comprising a substrate, an anode, a cathode, and an organic light-emitting functional layer. The organic light-emitting functional layer may include a light-emitting layer, a light-emitting auxiliary layer, a hole transport layer, a hole injection layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., or may only include a light-emitting layer and one or more other layers. The hole blocking layer or electron transport layer may contain one or more components of the compounds represented by the above-described general formula I. Optionally, a capping layer, a protective layer, and / or an encapsulation layer are further provided above the organic light-emitting functional layer.
[0034] The substrate described in this invention can be any substrate typically used in organic light-emitting devices. It can be a glass or transparent plastic substrate, an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance, and their applications vary depending on their properties.
[0035] As for the materials used in the hole injection layer, hole transport layer, electron injection layer, and light-emitting layer, any material can be selected from known materials used in OLED devices.
[0036] The present invention will now be described in detail with reference to specific embodiments. Unless otherwise specified, all raw materials and solvents used in the synthesis embodiments are commercially available, and the solvents were used directly without further processing.
[0037] Example
[0038] Example 1: Synthesis of Compound 7
[0039] Synthesis route:
[0040] Synthesis method:
[0041] 1) Add 10 mmol of 7-1, 10 mmol of 7-2, and 10 mL of dioxane:water (mass ratio 4:1) to a reaction flask, mix, and transfer to a 50 mL flask. Reflux for 24 hours. Cool to room temperature, then slowly add saturated MgSO4 aqueous solution and ethyl acetate to the solution for extraction three times. Remove the solvent from the organic layer using a rotary evaporator, and then obtain compound 7 by column chromatography.
[0042] The structure of the target product compound 7 was tested: the theoretical value was 861.41 and the measured value was 862.07 by liquid chromatography-mass spectrometry (LC-MS).
[0043] Example 2: Synthesis of Compound 19
[0044] Following the synthesis steps and reaction conditions of Example 1, compound 19 was synthesized. The LC-MS (m / z) values obtained by liquid chromatography-mass spectrometry were 937.44 and 938.16, respectively.
[0045] Example 3: Synthesis of Compound 42
[0046] Following the synthesis steps and reaction conditions of Example 1, compound 42 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 838.40 and a measured value of 839.06 (m / z).
[0047] Example 4: Synthesis of Compound 58
[0048] Following the synthesis steps and reaction conditions of Example 1, compound 58 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 861.41 and a measured value of 862.11 (m / z).
[0049] Example 5: Synthesis of Compound 92
[0050] Following the synthesis steps and reaction conditions of Example 1, compound 92 was synthesized. The LC-MS (m / z) values obtained by liquid chromatography-mass spectrometry were 813.41 and 814.03, respectively.
[0051] Example 6: Synthesis of Compound 100
[0052] Following the synthesis steps and reaction conditions of Example 1, compound 100 was synthesized. The LC-MS (m / z) values obtained by liquid chromatography-mass spectrometry were 711.36 and 711.92, respectively.
[0053] Example 7: Synthesis of Compound 109
[0054] Following the synthesis steps and reaction conditions of Example 1, compound 109 was synthesized. The LC-MS (m / z) values obtained by liquid chromatography-mass spectrometry were 813.41 and 814.05, respectively.
[0055] Example 8: Synthesis of Compound 122
[0056] Following the synthesis steps and reaction conditions of Example 1, compound 122 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 961.44 and a measured value of 962.20 (m / z).
[0057] Example 9: Synthesis of Compound 124
[0058] Following the synthesis steps and reaction conditions of Example 1, compound 124 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 827.39 and a measured value of 828.01 (m / z).
[0059] Example 10: Synthesis of Compound 133
[0060] Following the synthesis steps and reaction conditions of Example 1, compound 133 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 805.35 and a measured value of 805.97 (m / z).
[0061] Example 11: Synthesis of Compound 144
[0062] Following the synthesis steps and reaction conditions of Example 1, compound 144 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 779.33 and a measured value of 779.95 (m / z).
[0063] Example 12: Synthesis of Compound 145
[0064] Following the synthesis steps and reaction conditions of Example 1, compound 145 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 909.41 and a measured value of 910.03 (m / z).
[0065] Example 13: Synthesis of Compound 158
[0066] Following the synthesis steps and reaction conditions of Example 1, compound 158 was synthesized. The LC-MS (m / z) values obtained by liquid chromatography-mass spectrometry were 837.41 and 838.05, respectively.
[0067] Example 14: Synthesis of Compound 165
[0068] Following the synthesis steps and reaction conditions of Example 1, compound 165 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 875.50 and a measured value of 876.18 (m / z).
[0069] Example 15: Synthesis of Compound 168
[0070] Following the synthesis steps and reaction conditions of Example 1, compound 168 was synthesized. LC-MS analysis using liquid chromatography-mass spectrometry yielded a theoretical value of 821.46 and a measured value of 822.10 (m / z).
[0071] The following are several examples of applications of the triazine compounds described in this invention in OLED devices to further illustrate the beneficial effects of the compounds. The materials used in the examples were either commercially available or synthesized in-house.
[0072] Manufacturing of OLED devices:
[0073] As a reference fabrication method for one embodiment of the device, the present invention involves depositing a 50-500 nm ITO / Ag / ITO layer as the anode on an alkali-free glass substrate. Then, a hole injection layer (5 nm-20 nm), a hole transport layer (50-150 nm), a light-emitting auxiliary layer (5-120 nm), a light-emitting layer (20-50 nm), a hole blocking layer (5-20 nm), an electron transport layer (20-80 nm), and an electron injection layer (1-10 nm) are deposited on the anode. Next, Mg and Ag (weight ratio 1:9, 100-150 nm) are co-deposited to form a semi-transparent cathode, followed by the deposition of a capping compound. Finally, the light-emitting device is encapsulated using epoxy resin adhesive under a nitrogen atmosphere.
[0074] In a preferred embodiment, the OLED device provided by the present invention has the following structure: First, an alkali-free glass substrate is washed with isopropanol for 15 minutes using an ultrasonic cleaner, followed by a 30-minute UV ozone cleaning treatment in air. The treated substrate is then vacuum-deposited with ITO / Ag / ITO 100nm as the anode. Next, a hole injection layer (HT:PD, 10nm, 2%), a hole transport layer (HT, 130nm), a light-emitting auxiliary layer (BP, 5nm), a blue light-emitting layer (body material: dopant material = BH:BD (weight ratio 98:2, 30nm)), a hole blocking layer (compound 7, 5nm), an electron transport layer (ET:Liq = 1:1, 30nm), and an electron injection layer (Yb, 1nm) are sequentially deposited. Then, Mg and Ag (weight ratio 1:9, 130nm) are co-deposited to form a semi-transparent cathode. Finally, compound CPL (65nm) is deposited as a capping layer. Finally, the light-emitting device was encapsulated using epoxy resin adhesive under a nitrogen atmosphere, referred to as Application Example 1. The molecular structural formulas of the relevant materials are shown below (particularly preferably selected from the following structures, but this does not mean that the invention is limited to the following structures):
[0075] Application Examples 2-15 and Comparative Example 1 were prepared using the method described in Application Example 1 above, with the only difference being that compounds listed in Table 1 were used as hole-blocking materials instead of compound 7 in Application Example 1. The structure of Ref-1 used in the Comparative Example is as follows:
[0076] Performance evaluation of OLED devices:
[0077] The current of the OLED device at different voltages was measured using a Keithley 2365A digital nanovoltmeter, and then the current density of the OLED device at different voltages was obtained by dividing the current by the emitting area. The brightness and radiant energy flux density of the OLED device at different voltages were measured using a Konicaminolta CS-2000 spectroradiometer. Based on the current density and brightness of the OLED device at different voltages, the current density (10 mA / cm²) at the same voltage was obtained. 2 The operating voltage (Volt) and current efficiency (cd / A) are given by BI = E / CIEy, which refers to the Blue Index in blue light and is also a parameter measuring the luminous efficiency of blue light. E refers to the current efficiency, and CIEy refers to the ordinate color point obtained by substituting the wavelength of the device's emission half-width into the CIE1930 software. The test data are shown in Table 1.
[0078] Table 1. Examples of Hole Blocking Materials, Devices, and Electroluminescence Properties
[0079] As shown in Table 1, compared with Comparative Example 1, Application Examples 1 to 15 exhibit lower operating voltages, higher BI luminous efficiency, and longer lifespan. The performance improvements in each application example are based on the fact that the triazine compounds of this invention are dendritic molecules with a triazine structure at their core. The nitrogen-containing heterocycles have strong electron-withdrawing capabilities and large conjugated planes, giving the compounds good thermal stability, a higher glass transition temperature, and improved device lifespan. Simultaneously, the combination of fluorene groups with alkyl and aromatic groups significantly influences the luminescent properties of the compounds, thereby improving the device's luminous efficiency, achieving better balance in electron and hole transport and exciton conversion, and reducing device power consumption.
[0080] This specific embodiment is merely an explanation of the present invention and is not intended to limit the invention. After reading this specification, those skilled in the art can make modifications to this embodiment without contributing any inventive step, but such modifications are protected by patent law as long as they are within the scope of the claims of the present invention.
Claims
1. A triazine compound, characterized by, The triazine compound has the following formula I: In Formula I, R1, R2, R3, and R4 are each independently monosubstituted, disubstituted, or have the maximum number of substitutions; R1 and R2 are each independently selected from hydrogen, deuterium, cyano, cyano-substituted or unsubstituted C6-C30 aryl, C5-C36 heteroaryl; L is independently selected from single bond, deuterated or undeuterated C6-C30 arylene; R3 and R4 are each selected from substituted or unsubstituted C1-C24 alkyl, C3-C20 cycloalkyl; when R3 and R4 contain substitutions, the substitutions are selected from one or more of deuterium and C6-C30 aryl, and the structure shown in Formula I can be partially or completely deuterated.
2. The triazine compound according to claim 1, characterized in that, In Formula I, R1 and R2 are each independently selected from hydrogen, deuterium, cyano, cyano-substituted or unsubstituted phenyl, cyano-substituted or unsubstituted naphthyl, cyano-substituted or unsubstituted phenanthyl, cyano-substituted or unsubstituted naphthylphenyl, cyano-substituted or unsubstituted biphenyl, and dibenzofuranyl.
3. The triazine compound according to claim 1, characterized by In Formula I, L is independently selected from single bonds, deuterated or undeuterated phenylene, and deuterated or undeuterated biphenylene; R3 and R4 are each independently selected from methyl, ethyl, propyl, tert-butyl, pentyl, phenylpropyl, diphenylethyl, phenyl-substituted tert-butyl, and cyclopentyl.
4. The triazine compound according to claim 1, characterized by The triazine compound is selected from any one of the following chemical structures, where D represents deuterium:
5. The use of the triazine compounds according to any one of claims 1-4 in the preparation of organic electroluminescent devices.
6. A formulation characterized in that, The formulation comprises a triazine compound as described in any one of claims 1-4 and at least one solvent.
7. An organic electroluminescent device, characterized by The organic electroluminescent device includes: Substrate layer; A first electrode is located on the substrate; An organic light-emitting functional layer is disposed on the first electrode; The second electrode is located on the organic light-emitting functional layer; The organic light-emitting functional layer includes a triazine compound as described in any one of claims 1-4.
8. The organic electroluminescent device according to claim 7, characterized in that At least one of the organic light-emitting functional layers is an electron transport layer or a hole blocking layer, and the electron transport layer or hole blocking layer includes a triazine compound as described in any one of claims 1-4.
9. The application of the organic electroluminescent device according to claim 7 in a display or lighting device.
10. A display or illumination device, characterized in that The device includes the organic electroluminescent device as described in claim 7.