Organic light-emitting device and display or lighting device with organic light-emitting device

Abstract

The invention relates to the technical field of organic photoelectric material preparation, in particular to an organic light-emitting device and a display or lighting device with the organic light-emitting device. According to the organic light-emitting device, energy level parameters and difference values of the light-emitting layer, the hole transport layer and the light-emitting auxiliary layer are limited, the material of the light-emitting auxiliary layer is particularly limited, and a naphthyl group and a benzoheterocycle which are specifically matched are combined in an arylamine mother nucleus, so that the compound has excellent light-emitting efficiency and relatively good thermal stability; meanwhile, when the organic light-emitting material is used as a light-emitting auxiliary layer material for a device, the organic light-emitting device can effectively have lower driving voltage and maintain the stability of the voltage, the light-emitting efficiency is improved, the service life is obviously prolonged, and the organic light-emitting material has a very good application prospect.

Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric material preparation, and in particular to an organic light-emitting device and a display or lighting device having the organic light-emitting device. Background Art

[0002] Organic light-emitting diodes (OLEDs), also known as organic electroluminescent devices, are a technology that converts electrical energy into light energy through organic light-emitting materials by applying voltage to organic electroluminescent elements, injecting holes from the anode and electrons from the cathode into the light-emitting layer respectively. The injected holes and electrons recombine to form excitons, resulting in light emission.

[0003] Existing blue light auxiliary materials are still insufficient in improving device performance. Even if multiple materials are used in combination, display technology still has problems such as high driving voltage and short display life, which seriously affects the further practical application of this technology.

[0004] Therefore, continuous efforts are needed to develop organic light-emitting devices with low voltage drive, high brightness and long life, and to find suitable OLED optoelectronic functional materials for OLED devices to solve the above problems. Summary of the Invention

[0005] To address the above technical issues, the present invention provides an organic light-emitting device and a display or lighting device having the same. The provided organic light-emitting device, comprising a specific triarylamine compound, can simultaneously achieve low startup voltage, high efficiency, and long operating life.

[0006] The organic light-emitting device provided by the present invention is realized by the following technical solutions: An organic light-emitting device, comprising: substrate layer; a first electrode, the first electrode being on the substrate; an organic light-emitting functional layer, the organic light-emitting functional layer being on the first electrode; a second electrode, the second electrode being on the organic light-emitting functional layer; The organic light-emitting functional layer includes a hole transport layer, a light-emitting auxiliary layer and a light-emitting layer; The hole transport layer comprises a hole transport material, and the HOMO energy level of the hole transport material is between -5.10 eV and -5.25 eV; The light-emitting layer includes a host material, and the HOMO energy level of the host material is between -5.55 eV and -5.70 eV; The luminescence-assisting layer includes a luminescence-assisting material having a structure shown in Formula I below, wherein the HOMO energy level of the luminescence-assisting material is between -5.30 eV and -5.50 eV, and the absolute value of the HOMO energy level difference between the luminescence-assisting material and the host material is less than 0.3 eV; the absolute value of the HOMO energy level difference between the hole transport material and the luminescence-assisting material is less than 0.3 eV; ; wherein X is selected from O or S, ring A is selected from phenyl or naphthyl; L1, L2, and Ar1 are each independently selected from a deuterated or non-deuterated C6-C30 aryl group, and at least one of L1, L2, and Ar1 is selected from naphthyl.

[0007] Preferably, the hydrogen atoms of the compound of formula I may be partially or fully deuterated.

[0008] Preferably, the formula I is selected from any one of the following structures: ; The substitution ranges of X, L1, L2, Ar1 and ring A are the same as defined above.

[0009] More preferably, the formula A to formula D is selected from any one of the following structures: ; The substitution ranges of X, L1, L2, Ar1 and ring A are the same as defined above.

[0010] More preferably, the formula A to formula D can be selected from any one of the following structures: ; The substitution ranges of X, L1, L2 and Ar1 are the same as defined above.

[0011] Preferably, L1, L2, and Ar1 are each independently selected from deuterated or undeuterated phenyl, deuterated or undeuterated naphthyl, and deuterated or undeuterated phenanthrenyl.

[0012] Preferably, L1 is independently selected from deuterated or undeuterated phenyl, deuterated or undeuterated naphthyl.

[0013] According to one or more embodiments, the present invention provides an organic light-emitting device, comprising: substrate layer; a first electrode, the first electrode being on the substrate; an organic light-emitting functional layer, the organic light-emitting functional layer being on the first electrode; a second electrode, the second electrode being on the organic light-emitting functional layer; The organic light-emitting functional layer includes a hole transport layer, a light-emitting auxiliary layer and a light-emitting layer in sequence; The hole transport layer comprises a hole transport material, and the HOMO energy level of the hole transport material is between -5.10 eV and -5.25 eV; The light-emitting layer includes a host material, and the HOMO energy level of the host material is between -5.55 eV and -5.70 eV; The HOMO energy level of the luminescence auxiliary material is between -5.30 eV and -5.50 eV, and the absolute value of the HOMO energy level difference between the luminescence auxiliary material and the host material is less than 0.3 eV; the absolute value of the HOMO energy level difference between the hole transport material and the luminescence auxiliary material is less than 0.3 eV; the luminescence auxiliary layer has any one of the following chemical structures, wherein "D" represents deuterium: .

[0014] The organic electroluminescent device of the present invention can be used in OLED lighting or display devices. Preferably, the organic electroluminescent device prepared by the present invention is used in smartphones, tablet computers, smart wearable devices, televisions, VR, micro-displays, and automobile central control screens or automobile taillights.

[0015] The present invention also provides a display or lighting device, which comprises one or more of the organic electroluminescent devices described above.

[0016] The present invention also provides a composition comprising a compound having a structure as described in Formula I.

[0017] The present invention also provides a preparation comprising the composition described above and at least one solvent. The solvent is not particularly limited and can include those well known to those skilled in the art, such as unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetralin, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, hexyl chloride, bromohexane, chlorocyclohexane, bromocyclohexane, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, ether solvents such as tetrahydrofuran and tetrahydropyran, and ester solvents such as alkyl benzoates.

[0018] In summary, compared with the prior art, the present invention has the following beneficial effects: The organic electroluminescent device of the present invention defines the parameters of the compound used in the luminescent auxiliary layer and the organic functional layers matched therewith, fixes the triarylamine compound used in the luminescent auxiliary layer with an aromatic fused heterocyclic group and a naphthyl group, adjusts the position of the naphthyl group in the compound structure and the connection site of the aromatic fused heterocyclic group, and defines the key parameters of the luminescent layer and the hole transport layer matched therewith. This can effectively enable the organic light-emitting device to have a lower driving voltage while maintaining voltage stability, improve luminous efficiency, and achieve a better service life of the device. DETAILED DESCRIPTION

[0019] The following is a clear and complete description of the technical solutions of the embodiments of the present invention. Obviously, the embodiments described are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making any creative efforts shall fall within the scope of protection of the present invention.

[0020] The term "aryl" refers to and includes monocyclic aromatic hydrocarbon groups and polycyclic aromatic ring systems. Polycyclic rings can have two or more rings in which two carbon atoms are shared by two adjacent rings (the rings are "fused"), wherein at least one of the rings is an aromatic hydrocarbon group, for example, the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocycle and / or heteroaryl. Preferred aryl groups are aryl groups containing 6-30 carbon atoms. Particularly preferred are aryl groups with six carbon atoms, ten carbon atoms, twelve carbon atoms or fourteen carbon atoms. For example, phenyl, biphenyl, naphthyl, phenanthrenyl, etc. In addition, aryl groups can be optionally substituted.

[0021] Throughout this specification, unless explicitly stated to the contrary, references to "comprising" any component will be understood to implicitly include, but not exclude, any other elements. 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 "over" another element, it can be "directly on" the other element, or intervening elements may be present. Furthermore, "on" or "above" refers to being above the target portion, not necessarily above in terms of gravity.

[0022] One object of the present invention is to provide an organic electroluminescent device, which includes: a substrate layer; a first electrode, which is on the substrate; an organic light-emitting functional layer, which is on the first electrode; a second electrode, which is on the organic light-emitting functional layer; the organic light-emitting functional layer includes a hole transport layer, a light-emitting auxiliary layer and a light-emitting layer, the hole transport layer includes a hole transport material, and the HOMO energy level of the hole transport material is between -5.10eV and -5.25eV; the light-emitting layer includes a main material, and the HOMO energy level of the main material is between -5.55eV and -5.70eV; the HOMO energy level of the light-emitting auxiliary material is between -5.30eV and -5.50eV, and the absolute value of the HOMO energy level difference between the light-emitting auxiliary material and the main material is less than 0.3eV; the absolute value of the HOMO energy level difference between the hole transport material and the light-emitting auxiliary material is less than 0.3eV; and the light-emitting auxiliary layer includes a triarylamine compound having a naphthyl group and an aromatic fused heterocyclic group.

[0023] In one embodiment of the present invention, the luminescence-assisting layer in the organic electroluminescent (OLED) device comprises one or more compounds represented by the above formula I as luminescence-assisting materials.

[0024] 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, wherein 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, an electron transport layer, an electron injection layer, etc.; wherein the light-emitting auxiliary layer comprises one or more compounds represented by the above formula I. Optionally, the device further comprises a cover layer, a protective layer, and / or an encapsulation layer.

[0025] The substrate of the present invention can be any substrate used in typical organic light-emitting devices. It can be glass or transparent plastic, or an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have varying mechanical strength, thermal stability, transparency, surface smoothness, and water resistance, and their applications vary depending on the properties of the substrate.

[0026] In a preferred embodiment of the present invention, the HOMO energy level of the hole transport material is between -5.10 eV and -5.25 eV; the hole transport layer can be selected from known or unknown materials, and is particularly preferably selected from the following structures, but the present invention is not limited to the following structures: .

[0027] The OLED device further comprises a light-emitting layer, wherein the light-emitting layer comprises a host material and a dopant material. The HOMO energy level of the host material is between -5.55 eV and -5.70 eV. The host material is preferably selected from the following structures, but the present invention is not limited to the following structures: ; The doping material can be selected from known or unknown materials. At the same time, the main material and the doping material also need to have appropriate energy levels so that they can effectively cooperate and stimulate luminescence.

[0028] As materials for the hole injection layer, the electron injection layer, and the electron transport layer, any material can be selected from known materials used in OLED devices.

[0029] The present invention is described in detail below with reference to specific examples. Synthesis Examples All raw materials and solvents were purchased commercially unless otherwise specified, and the solvents were used directly without further treatment; Examples of deuterated raw materials or intermediates include: (CAS: 3060209-21-1), (CAS: 1940112-79-7) and others are commercially available.

[0030] Example

[0031] Example 1: Synthesis of Compound 1 Synthesis route: ; Synthesis method: 1) Add 1-1 (10 mmol), 1-2 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of toluene to the reaction flask. After nitrogen replacement, add pd2dba3 (5×10 -2 mmoL), Sphos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 10×10 -2100 mL of n-heptane was added to the mixture, and the mixture was slurried to obtain intermediate product 1-3. 2) Add 1-3 (10 mmol), 1-4 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of xylene to the reaction flask. After nitrogen replacement, add pd2dba3 (5×10 -2 mmoL)、Sphos(10×10 -2 100 mL of methyl paraformaldehyde (MPa) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to stop the reaction. The mixture was cooled to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the xylene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried to obtain the target product 1. The structure of the test target product 1 was analyzed by liquid chromatography-mass spectrometry (LC-MS) (m / z): the theoretical value was 739.29 and the test value was 739.83.

[0032] Example 2: Synthesis of Compound 28 The difference from Example 1 is that reactant 1-2 is changed to , referring to the synthesis steps and reaction conditions of Example 1, compound 28 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 789.30, and the test value was 789.88.

[0033] Example 3: Synthesis of Compound 50 The difference from Example 1 is that reactant 1-2 is changed to , referring to the synthesis steps and reaction conditions of Example 1, compound 50 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 739.29, and the test value was 739.81.

[0034] Example 4: Synthesis of Compound 51 The difference from Example 1 is that reactant 1-2 is changed to , referring to the synthesis steps and reaction conditions of Example 1, compound 51 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 739.29, and the test value was 739.83.

[0035] Example 5: Synthesis of Compound 59 The difference from Example 1 is that reactant 1-2 is changed to , change reactants 1-4 to , referring to the synthesis steps and reaction conditions of Example 1, compound 59 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 755.26, and the test value was 755.88.

[0036] Example 6: Synthesis of Compound 60 The difference from Example 1 is that reactant 1-2 is changed to , change reactants 1-4 to , referring to the synthesis steps and reaction conditions of Example 1, compound 60 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 805.28, and the test value was 805.94.

[0037] Example 7: Synthesis of Compound 108 The difference from Example 1 is that reactant 1-2 is changed to , change reactants 1-4 to , referring to the synthesis steps and reaction conditions of Example 1, compound 108 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 839.32, and the test value was 839.96.

[0038] Example 8: Synthesis of Compound 110 The difference from Example 1 is that reactant 1-2 is changed to , change reactants 1-4 to , referring to the synthesis steps and reaction conditions of Example 1, compound 110 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 789.30, and the test value was 789.86.

[0039] Example 9: Synthesis of Compound 140 ; Synthesis method: 1) Add SM1-140 (10 mmol), SM2-140 (10 mmol), Na2CO3 (12 mmol), 100 mL of toluene, 50 mL of ethanol, and 100 mL of water to a reaction flask. Add Pd(dppf)Cl2 (0.1 mmol) and replace the nitrogen atmosphere three times. Heat and reflux for 6 h. Add 200 mL of water to the reaction mixture, stir, and allow to stand for separation. Wash the toluene phase twice with water and once with saturated brine, dry over anhydrous sodium sulfate, and filter. Vacuum fractional distillation at 118-125°C is performed using an oil pump to obtain the intermediate product S1-140. 2) Add S1-140 (10 mmol), SM3-140 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of xylene to the reaction flask. After nitrogen replacement, add pd2dba3 (5×10 -2 mmoL)、Sphos(10×10 -2 100 mL of methyl paraformaldehyde (MPA) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to stop the reaction. The temperature was lowered to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the xylene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried to obtain the intermediate product S2-140. 3) Add S2-140 (10 mmol), SM4-140 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of xylene to the reaction flask. After nitrogen replacement, add pd2dba3 (5×10 -2 mmoL)、Sphos(10×10 -2 100 mL of methyl paraformaldehyde (MPA) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to stop the reaction. The temperature was then lowered to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the xylene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried. This afforded the final product, Compound 140. Liquid chromatography-mass spectrometry analysis yielded the LC-MS (m / z): the theoretical value was 761.43 and the measured value was 961.97.

[0040] Example 10: Synthesis of Compound 142 The difference from Example 9 is that the reactant SM1-140 is changed to , change the reactant SM3-140 to , referring to the synthesis steps and reaction conditions of Example 9, compound 142 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 750.36, and the test value was 750.84.

[0041] Example 11: Synthesis of Compound 148 The difference from Example 9 is that the reactant SM4-140 is changed to , referring to the synthesis steps and reaction conditions of Example 9, compound 148 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 811.44, and the test value was 811.96.

[0042] Example 12: Synthesis of Compound 150 ; Synthesis method: 1) Add SM1-150 (10 mmol), SM2-150 (10 mmol), Na2CO3 (12 mmol), 100 mL of toluene, 50 mL of ethanol, and 100 mL of water to a reaction flask. Add Pd(dppf)Cl2 (0.1 mmol) and replace the nitrogen atmosphere three times. Heat and reflux for 6 h. Add 200 mL of water to the reaction mixture, stir, and allow to stand for separation. Wash the toluene phase twice with water and once with saturated brine, dry over anhydrous sodium sulfate, and filter. Vacuum fractional distillation at 118-125°C is performed using an oil pump to obtain the intermediate product S1-150. 2) Add S1-150 (10 mmol), SM3-150 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of xylene to the reaction flask. After nitrogen replacement, add pd2dba3 (5×10 -2 mmoL)、Sphos(10×10 -2 100 mL of methyl paraformaldehyde (MPA) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to stop the reaction. The temperature was lowered to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the xylene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried to obtain the intermediate product S2-150. 3) Add SM3-150 (10 mmol), SM4-150 (10 mmol), Na2CO3 (12 mmol), 100 mL of toluene, 50 mL of ethanol, and 100 mL of water to a reaction flask. Add Pd(dppf)Cl2 (0.1 mmol) and replace the nitrogen atmosphere three times. Heat and reflux for 6 h. Add 200 mL of water to the reaction mixture, stir, and allow to stand for separation. Wash the toluene phase twice with water and once with saturated brine, dry over anhydrous sodium sulfate, and filter. Vacuum fractional distillation at 118-125°C is performed using an oil pump to obtain the intermediate product S3-150. 4) Add S2-150 (10 mmol), S3-150 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of xylene to the reaction flask. After nitrogen replacement, add pd2dba3 (5×10 -2 mmoL)、Sphos(10×10 -2 100 mL of methyl paraformaldehyde (MPA) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to terminate the reaction. The mixture was cooled to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the xylene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried. This afforded the final product, Compound 150. Liquid chromatography-mass spectrometry analysis yielded the LC-MS (m / z): theoretical value was 754.38, and the measured value was 754.92.

[0043] Example 13: Synthesis of Compound 152 The difference from Example 1 is that reactant 1-2 is changed to , change reactants 1-4 to , referring to the synthesis steps and reaction conditions of Example 1, compound 152 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 802.38, and the test value was 802.98.

[0044] Example 14: Synthesis of Compound 153 ; Synthesis method: 1) Add SM1-153 (10 mmol), SM2-153 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of toluene to the reaction flask. After nitrogen replacement, add pd2dba3 (5×10 -2 mmoL), Sphos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 10×10 -2 100 mL of methyl paraformaldehyde (MPA) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to stop the reaction. The temperature was then lowered to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the toluene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried to obtain the intermediate product S1-153. 2) Add SM3-153 (10 mmol), SM4-153 (10 mmol), Na2CO3 (12 mmol), 100 mL of toluene, 50 mL of ethanol, and 100 mL of water to a reaction flask. Add Pd(dppf)Cl2 (0.1 mmol) and replace the nitrogen atmosphere three times. Heat and reflux for 6 h. Add 200 mL of water to the reaction mixture, stir, and allow to stand for separation. Wash the toluene phase twice with water and once with saturated brine, dry over anhydrous sodium sulfate, and filter. Vacuum fractional distillation at 118-125°C is performed using an oil pump to obtain the intermediate product S2-153. 3) Add S1-153 (10 mmol), S2-153 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of xylene to the reaction flask. After nitrogen replacement, add pd2dba3 (5×10 -2 mmoL)、Sphos(10×10 -2 100 mL of methyl paraformaldehyde (MPa) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to terminate the reaction. The mixture was cooled to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the xylene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried. This afforded the final product, compound 153. Liquid chromatography-mass spectrometry analysis yielded the LC-MS (m / z): the theoretical value was 743.31 and the measured value was 743.89.

[0045] Example 15: Synthesis of Compound 154 ; Synthesis method: 1) Add SM1-154 (10 mmol), SM2-154 (10 mmol), Na2CO3 (12 mmol), 100 mL of toluene, 50 mL of ethanol, and 100 mL of water to a reaction flask. Add Pd(dppf)Cl2 (0.1 mmol) and replace the nitrogen atmosphere three times. Heat and reflux for 6 h. Add 200 mL of water to the reaction mixture, stir, and allow to stand for separation. Wash the toluene phase twice with water and once with saturated brine, dry over anhydrous sodium sulfate, and filter. Vacuum fractional distillation at 118-125°C is performed using an oil pump to obtain the intermediate product S1-154. 2) Add S1-154 (10 mmol), SM3-154 (10 mmol), Na2CO3 (12 mmol), 100 mL of toluene, 50 mL of ethanol, and 100 mL of water to a reaction flask. Add Pd(dppf)Cl2 (0.1 mmol) and replace the nitrogen atmosphere three times. Heat and reflux for 6 h. Add 200 mL of water to the reaction mixture, stir, and allow to stand for separation. Wash the toluene phase twice with water and once with saturated brine, dry over anhydrous sodium sulfate, and filter. Vacuum fractional distillation at 118-125°C is performed using an oil pump to obtain the intermediate product S2. 3) Add S2-154 (10 mmol), SM4-154 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of toluene to the reaction flask. After nitrogen replacement, add pd2dba3 (5×10 -2 mmoL), Sphos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 10×10 -2 100 mL of methyl paraformaldehyde (MPA) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to stop the reaction. The temperature was lowered to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the toluene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried to obtain the intermediate product S3-154. 4) S3-154 (10 mmol), SM5-154 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of xylene were added to the reaction flask. After nitrogen replacement, PD2DBA3 (5×10 -2 mmoL)、Sphos(10×10 -2100 mL of methyl paraformaldehyde (MPA) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to terminate the reaction. The mixture was cooled to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the xylene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried. This afforded the final product, compound 154. Liquid chromatography-mass spectrometry analysis yielded the LC-MS (m / z): theoretical value was 799.37, and the measured value was 799.95.

[0046] Example 16: Synthesis of Compound 155 ; Synthesis method: 1) Add SM1-155 (10 mmol), SM2-155 (10 mmol), Na2CO3 (12 mmol), 100 mL of toluene, 50 mL of ethanol, and 100 mL of water to a reaction flask. Add Pd(dppf)Cl2 (0.1 mmol) and replace the nitrogen atmosphere three times. Heat and reflux for 6 h. Add 200 mL of water to the reaction mixture, stir, and allow to stand for separation. Wash the toluene phase twice with water and once with saturated brine, dry over anhydrous sodium sulfate, and filter. Vacuum fractional distillation at 118-125°C is performed using an oil pump to obtain the intermediate product S1-155. 2) Add SM3-155 (10 mmol), SM4-155 (10 mmol), Na2CO3 (12 mmol), 100 mL of toluene, 50 mL of ethanol, and 100 mL of water to a reaction flask. Add Pd(dppf)Cl2 (0.1 mmol) and replace the nitrogen atmosphere three times. Heat and reflux for 6 h. Add 200 mL of water to the reaction mixture, stir, and allow to stand for separation. Wash the toluene phase twice with water and once with saturated brine, dry over anhydrous sodium sulfate, and filter. Vacuum fractional distillation at 118-125°C is performed using an oil pump to obtain the intermediate product S2-155. 3) Add S1-155 (10 mmol), S2-155 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of toluene to the reaction flask. After nitrogen replacement, add pd2dba3 (5×10 -2 mmoL), Sphos (2-dicyclohexylphosphine-2',6'-dimethoxy-1,1'-biphenyl, 10×10 -2 100 mL of methyl paraformaldehyde (MPA) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to stop the reaction. The temperature was lowered to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the toluene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried to obtain the intermediate product S3-155. 4) Add S3-155 (10 mmol), SM4-155 (12 mmol), sodium tert-butoxide (12 mmol), and 200 mL of xylene to the reaction flask. After nitrogen replacement, add PD2DBA3 (5×10 -2 mmoL)、Sphos(10×10 -2 100 mL of methyl paraformaldehyde (MPa) was added to the mixture, heated to 100-120°C, and refluxed for 6 hours to terminate the reaction. The mixture was cooled to 30-40°C, 200 mL of water was added, and the layers were separated. After washing twice with water, the xylene was concentrated, and 100 mL of n-heptane was added and the mixture was slurried. This afforded the final product, compound 155. Liquid chromatography-mass spectrometry analysis yielded the LC-MS (m / z): theoretical value was 799.37, and the measured value was 799.97.

[0047] Example 17: Synthesis of Compound 156 The difference from Example 9 is that reactant SM4 is changed to , referring to the synthesis steps and reaction conditions of Example 9, compound 156 was synthesized, and the LC-MS (m / z) was obtained by liquid chromatography-mass spectrometry analysis: the theoretical value was 811.44, and the test value was 811.98.

[0048] Several examples of the application of the organic compounds of the present invention in OLED devices are listed below to further illustrate the beneficial effects of the compounds of the present invention. The materials used in the examples were purchased commercially or synthesized by ourselves.

[0049] Fabrication of OLED devices:

[0050] As a reference preparation method for a device embodiment, the present invention utilizes a 50-500nm thick ITO / Ag / ITO (ITO:Ag:ITO weight ratio = 1:(10-20):1) anode deposited on an alkali-free glass substrate. A hole injection layer (5nm-20nm), a hole transport layer (50-150nm), a luminescent auxiliary layer (5-120nm), a light-emitting layer (host material: dopant material, dopant weight ratio = 0.5%-10%, 20-50nm), a hole blocking layer (5-20nm), an electron transport layer (20-80nm), and an electron injection layer (1-10nm) are then deposited on the anode. A semi-transparent cathode is then formed by co-evaporating Mg and Ag (weight ratio = 1:9, 10-50nm). A capping compound (50-90nm) is then evaporated. Finally, the light-emitting device is encapsulated with an epoxy resin adhesive under a nitrogen atmosphere.

[0051] In a preferred embodiment, the structure of the OLED device provided by the present invention is as follows: first, an alkali-free glass substrate is cleaned with isopropyl alcohol using an ultrasonic cleaner for 15 minutes, and then subjected to UV ozone cleaning treatment in air for 30 minutes. The treated substrate was vacuum-deposited with an ITO / Ag / ITO anode (ITO:Ag:ITO weight ratio = 1:10:1, 120nm). A hole injection layer (HT:PD weight ratio = 98:2, 10nm), a hole transport layer (HT, 130nm), a luminescent auxiliary layer (compound 1, 5nm), an emitting layer (host material BH: dopant material BD weight ratio = 98:2, 30nm), a hole blocking layer (HBL, 5nm), an electron transport layer (ET:Liq = 1:1, 30nm), and an electron injection layer (Yb, 1nm) were sequentially deposited. A semi-transparent cathode was formed by co-depositing Mg and Ag (weight ratio = 1:9, 14nm). Compound CPL (65nm) was then deposited as a capping layer. The light-emitting device was then encapsulated with epoxy resin adhesive under a nitrogen atmosphere. This is designated Application Example 1. The molecular structural formula of the relevant materials is as follows (particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures): ; The HOMO energy level of the HT structure used in the hole transport layer is -5.122 eV; the HOMO energy level of the BH structure of the main material in the light-emitting layer is -5.684 eV.

[0052] Application Examples 2 to 17 and Comparative Example 1 were prepared by referring to the method provided in Application Example 1, with the only difference being that the compounds listed in Table 1 were used as luminescent auxiliary materials to replace Compound 1 in Application Example 1.

[0053] The structures of Ref-1 and Ref-2 used in Comparative Example 1-2 are as follows: .

[0054] Comparative Example 3: The difference between this comparative example and Example 1 is that the main material Ref-BH used in the light-emitting layer is , the HOMO energy level is -5.75eV.

[0055] Comparative Example 4: The difference between this comparative example and Example 1 is that the hole transport layer material Ref-HT used is , the HOMO energy level is -5.32eV.

[0056] Performance evaluation of OLED devices:

[0057] The current of the OLED device at different voltages was measured using a Keithley 2365A digital nanovoltmeter, and the current density of the OLED device at different voltages was obtained by dividing the current by the luminous 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 luminance at the same current density (10 mA / cm 2 ) operating voltage Volt and current efficiency (cd / A). BI = E / CIEy, which refers to the Blue Index of blue light and is a parameter that measures the luminous efficiency of blue light. E refers to the current efficiency, and CIEy refers to the vertical coordinate color point obtained by substituting the device's half-width at half-peak wavelength into the CIE1930 software. The test data is shown in Table 1.

[0058] Table 1 Application examples of luminescent auxiliary materials and their electronic luminescent properties

[0059] It can be seen from Table 1 that, compared with Comparative Example 1, Application Examples 1 to 17 have lower operating voltage, higher BI luminous efficiency and longer service life.

[0060] By comparing Application Examples 1-7, 9, 10, 12, and 14 with Comparative Example 1, it can be seen that by extending the chain with a phenyl, naphthyl, or phenanthryl group on one side of the naphthyl group of the triarylamine, the compound of the present invention has better compatibility in the device than the compound of Comparative Example 1, thereby improving the application performance of the device.

[0061] Furthermore, Comparative Example 2 is compared with Application Examples 8, 11, 13, and 15-17. In the compound structure, a phenyl group is fused on one side of dibenzofuran, and groups are defined on the other two sides of the aromatic amine. The organic compound material of the present invention has better thermal stability and auxiliary transmission capability. In summary, the luminescent auxiliary material of the present invention has a large conjugated plane, which gives the compound good thermal stability and improves the service life of the device; at the same time, it improves the luminous efficiency of the device, can better achieve the balance of electron and hole transmission and the exciton conversion rate, and reduce the power consumption of the device.

[0062] To demonstrate the impact of the energy level coordination between the luminescence-assisting material, the hole transport material, and the main luminescent layer material in the present invention, Comparative Examples 3-4 are compared with Application Example 1. It can be seen that when the hole transport layer material and the main luminescent layer material selected in the device structure are not within the energy level range specified in this application, the luminescence-assisting material cannot form an appropriate energy level with the adjacent two layers, resulting in a decrease in device performance. The beneficial effects of the present invention are achieved based on the defined energy level coordination of the three layers and the specific luminescence-assisting material.

[0063] This specific embodiment is merely an explanation of the present invention and is not intended to limit the present invention. After reading this specification, those skilled in the art may make non-creative modifications to this embodiment as needed. However, as long as such modifications are within the scope of the claims of the present invention, they are protected by patent law.

Claims

1. An organic light-emitting device, comprising: substrate layer; a first electrode, the first electrode being on the substrate; an organic light-emitting functional layer, the organic light-emitting functional layer being on the first electrode; a second electrode, the second electrode being on the organic light-emitting functional layer; Characterized in that the organic light-emitting functional layer includes a hole transport layer, a light-emitting auxiliary layer and a light-emitting layer; The hole transport layer comprises a hole transport material, and the HOMO energy level of the hole transport material is between -5.10 eV and -5.25 eV; The light-emitting layer includes a host material, and the HOMO energy level of the host material is between -5.55 eV and -5.70 eV; The luminescence-assisting layer includes a luminescence-assisting material having a structure shown in Formula I below, wherein the HOMO energy level of the luminescence-assisting material is between -5.30 eV and -5.50 eV, and the absolute value of the HOMO energy level difference between the luminescence-assisting material and the host material is less than 0.3 eV; the absolute value of the HOMO energy level difference between the hole transport material and the luminescence-assisting material is less than 0.3 eV; ； In Formula I, X is selected from O or S, Ring A is selected from phenyl or naphthyl; L1, L2, and Ar1 are each independently selected from a deuterated or non-deuterated C6-C30 aryl group, and at least one of L1, L2, and Ar1 is selected from naphthyl.

2. The organic light-emitting device according to claim 1, wherein The formula I is selected from any one of the following structures: ； Wherein, the substitution range of X, L1, L2, Ar1 and ring A is the same as defined in claim 1.

3. The organic light-emitting device according to claim 2, wherein: The formula A to formula D are selected from any of the following structures: ； Wherein, the substitution range of X, L1, L2, Ar1 and ring A is the same as defined in claim 2.

4. The organic light-emitting device according to claim 2, wherein: The formula A to formula D are selected from any of the following structures: ； Wherein, the substitution range of X, L1, L2, and Ar1 is the same as defined in claim 2.

5. The organic light-emitting device according to claim 1, wherein The L1, L2, and Ar1 are each independently selected from a deuterated or undeuterated phenyl group, a deuterated or undeuterated naphthyl group, and a deuterated or undeuterated phenanthrenyl group.

6. The organic light-emitting device according to claim 1, wherein The L1 is independently selected from deuterated or undeuterated phenyl, deuterated or undeuterated naphthyl.

7. The organic light-emitting device according to claim 1, wherein The hydrogen atoms in the structure of Formula I may be fully or partially replaced by deuterium.

8. The organic light-emitting device according to claim 1, wherein The structure of formula I is selected from any one of the chemical structures shown below, wherein "D" represents deuterium: 。 9. A display or lighting device, characterized in that: The device comprises the organic light-emitting device according to any one of claims 1 to 8.

10. A composition, characterized in that The composition comprises a structure shown in the following formula I: ； wherein X is selected from O or S, ring A is selected from phenyl or naphthyl; L1, L2, and Ar1 are each independently selected from a deuterated or non-deuterated C6-C30 aryl group, and at least one of L1, L2, and Ar1 is selected from naphthyl.

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