CN114634511B

CN114634511B - Organic compound and application thereof

Info

Publication number: CN114634511B
Application number: CN202210288783.2A
Authority: CN
Inventors: 代文朋; 高威; 翟露
Original assignee: Wuhan Tianma Microelectronics Co Ltd
Current assignee: Wuhan Tianma Microelectronics Co Ltd
Priority date: 2022-03-22
Filing date: 2022-03-22
Publication date: 2023-10-31
Anticipated expiration: 2042-03-22
Also published as: CN114634511A

Abstract

The invention provides an organic compound and application thereof, wherein the organic compound has proper HOMO energy level and LUMO energy level, has higher carrier transmission rate and balanced carrier transmission performance, is beneficial to balance of hole and electron transmission in a device, obtains a wider carrier composite region, improves luminous efficiency, and has good thermal stability and film forming property.

Description

Organic compound and application thereof

Technical Field

The invention belongs to the technical field of organic electroluminescent materials, and relates to an organic compound and application thereof.

Background

The organic electroluminescent materials can be classified into two kinds of electroluminescent materials according to a luminescence mechanism, wherein the electroluminescent materials are radiation attenuation transitions of singlet excitons, and the electroluminescent materials are light emitted by radiation attenuation of triplet excitons to a ground state. According to the spin quantum statistical theory, the formation probability ratio of singlet excitons and triplet excitons is 1:3. The internal quantum efficiency of the fluorescent material is not more than 25%, and the external quantum efficiency is generally lower than 5%; the internal quantum efficiency of the electrophosphorescent material reaches 100% theoretically, and the external quantum efficiency can reach 20%.

Phosphorescent heavy metal materials have a long lifetime (mus) and can cause triplet-triplet annihilation and concentration quenching at high current densities, resulting in device performance degradation, so that heavy metal phosphorescent materials are typically doped into suitable host materials to form a host-guest doped system, so that energy transfer is optimized, luminous efficiency and lifetime are maximized. In the current state of research, heavy metal doping materials are already commercialized, and it is difficult to develop alternative doping materials. Therefore, it is a common idea for researchers to put the focus on developing phosphorescent host materials.

However, the existing phosphorescence host material has obvious difference in carrier transportation due to the fact that the HOMO energy level is not matched with the LUMO energy level and the energy level of the adjacent layer material, so that carriers are unbalanced in the light-emitting layer, and efficiency roll-off is serious; accordingly, it is desirable in the art to develop phosphorescent host materials with more excellent properties to overcome the problems.

Disclosure of Invention

In view of the shortcomings of the prior art, the invention aims to provide an organic compound and application thereof.

In order to achieve the aim of the invention, the invention adopts the following technical scheme:

it is an object of the present invention to provide an organic compound having a structure represented by the following formula I:

wherein X is ₁ -X ₁₅ Each independently selected from N OR CRa, ra is hydrogen, substituted OR unsubstituted C1-C10 alkyl, substituted OR unsubstituted C1-C10 cycloalkyl, substituted OR unsubstituted C6-C30 aryl, substituted OR unsubstituted C3-C30 heteroaryl, OR ₁ Or SR (S.J) ₁ 。

R ₁ Is a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 cycloalkyl group.

In the invention, the organic compound with the structure shown in the formula I has proper HOMO energy level and LUMO energy level, has higher carrier transmission rate and balanced carrier transmission performance, is beneficial to balance of hole and electron transmission in a device, and simultaneously obtains a wider carrier composite region, improves luminous efficiency, and has good thermal stability and film forming property.

In the present invention, the C1-C10 may each independently be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10,

The C6-C30 may each independently be C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C29, etc.

The C3-C30 may each independently be C3, C5, C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C29, and the like.

It is a second object of the present invention to provide an organic electroluminescent material comprising an organic compound according to one of the objects.

It is a further object of the present invention to provide an OLED device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, the material of the organic thin film layer comprising an organic compound according to one of the objects.

It is a fourth object of the present invention to provide a display panel comprising an OLED device as described in the third object.

A fifth object of the present invention is to provide an organic light emitting display device including the display panel as defined in the fourth object.

A sixth object of the present invention is to provide an electronic apparatus including the display panel as set forth in the fourth object.

Compared with the prior art, the invention has the following beneficial effects:

the organic compound has proper HOMO energy level and LUMO energy level, has higher carrier transmission rate and balanced carrier transmission performance, is beneficial to balance of hole and electron transmission in a device, and can obtain a wider carrier composite region, so that the luminous efficiency is improved, and in addition, the organic compound has good thermal stability and film forming property. The OLED device using the organic compound containing the lactam according to the present invention has a long lifetime, high efficiency, low operating voltage and high color purity.

Drawings

Fig. 1 is a schematic structural diagram of an OLED device according to the present invention, in which 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer (including a first hole transport layer 41 and a second hole transport layer 42), 5 is a light emitting layer, 6 is an electron transport layer, 7 is an electron injection layer, 8 is a cathode, 9 is a cap layer, and arrows indicate light directions.

Detailed Description

The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.

In one embodiment, the substituent of the substituted C1-C10 alkyl, substituted C1-C10 cycloalkyl, substituted C6-C30 aryl or substituted C3-C30 heteroaryl is deuterium, fluoro, trifluoromethyl, cyano, methyl, ethyl, t-butyl, isopropyl or methoxy.

In one embodiment, X ₁ -X ₁₅ At least one of them is N.

In one embodiment, ra is hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted phenylene-pyridinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted pyridinyl or substituted or unsubstituted triazinyl, substituted or unsubstituted arylamino, or substituted or unsubstituted carbazolyl;

in the case of the substituted group, the substituent is selected from C1-C10 alkyl or C6-C30 aryl.

In one embodiment, the organic compound is any one of the following compounds:

in the present invention, the preparation method of the organic compound is as follows:

In one embodiment, the organic thin film layer includes a light emitting layer including the organic compound according to one of the objects as a host material.

In the OLED device provided by the invention, the anode material can be metal, metal oxide or conductive polymer; wherein the metal comprises copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum and the like and alloys thereof, the metal oxide comprises Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide, indium Gallium Zinc Oxide (IGZO) and the like, and the conductive polymer comprises polyaniline, polypyrrole, poly (3-methylthiophene) and the like. In addition to the above materials and combinations thereof that facilitate hole injection, materials known to be suitable as anodes are included.

In the OLED device, the cathode material may be a metal or a multi-layer metal material; wherein the metal comprises aluminum, magnesium, silver, indium, tin, titanium, etc. and their alloys, and the multilayer metal material comprises LiF/Al, liO ₂ /Al、BaF ₂ Al, etc. Materials suitable for use as cathodes are also known in addition to the above materials that facilitate electron injection and combinations thereof.

In the OLED device, the organic thin film layer includes at least one light emitting layer (EML) and any one or a combination of at least two of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), or an Electron Injection Layer (EIL) disposed at both sides of the light emitting layer. In addition to the organic compound according to one of the objects of the present invention, the hole/electron injection and transport layer may be a carbazole compound, an arylamine compound, a benzimidazole compound, a metal compound, or the like. A cap layer (CPL) may also optionally be provided on the cathode (the side remote from the anode) of the OLED device.

The OLED device can be prepared by the following method: an anode is formed on a transparent or opaque smooth substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer. Among them, known film forming methods such as vapor deposition, sputtering, spin coating, dipping, ion plating, and the like can be used for forming the organic thin layer.

The following are illustrative examples of the preparation of the organic compounds according to the invention:

example 1

Synthesis of compound P3:

(1) P3-1 (0.5 mmol), P3-2 (0.5 mmol), K ₂ CO ₃ (0.5mmol)、PdCl ₂ (5×10 ^-4 mmol)、TPPDA(5×10 ^-4 mmol) was added to 3mL of o-xylene solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature and then dissolvedThe saturated MgSO was slowly added to the solution ₄ The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the product P3-3.

(2) P3-3 (0.5 mmol), iodobenzene (0.5 mmol), bis-trifluoroacetyl iodobenzene (PIFA, 0.2 mmol), boron trifluoride etherate (BF) ₃ .OEt ₂ 0.2 mmol) was added to a 3mL solution of methylene chloride, mixed, placed in a 50mL flask, and reacted at-30℃for 3 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution ₄ The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the product P3-4.

(3) P3-4 (10 mmol), P3-5 (12 mmol), palladium acetate Pd (OAc) ₂ (0.3 mmol) and cesium carbonate Cs ₂ CO ₃ (12 mmol) was added to a mixture of N, N dimethylformamide (10 mL) and reacted under reflux under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a celite pad, the filtrate was extracted with ethyl acetate, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by silica gel column chromatography to give the product P3-6.

(4) Intermediate P3-6 (2 mmol), triethylamine Et in a 50mL round bottom flask ₃ N (3 mmol) and phosgene (6 mmol in toluene 10 mL) were added to dry 20mL toluene and stirred under nitrogen at 0deg.C for 1h, and the resulting mixture was then reacted at room temperature for 5h. Added to water, then filtered through a pad of celite, the filtrate extracted with dichloromethane, then washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product purified by silica gel column chromatography to give the product P3-7.

(5) Intermediate P3-7 (3 mmol), palladium acetate Pd (OAc) in a 50mL round bottom flask ₂ (1 mmol), triphenylphosphine PPh ₃ (1.2 mmol), norbornene NBE (3 mmol), CS ₂ CO ₃ (12 mmol) and dried dichloroethane (20 mL) were stirred under nitrogen at 95℃for 48 h. The resulting intermediate was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate extracted with dichloromethane, then washed with water and taken upThe crude product was purified by silica gel column chromatography after drying over anhydrous magnesium sulfate, filtration and evaporation to give compound P3.

The structure of the target product P3 was tested: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) ₃₇ H ₂₂ N ₂ O, calculated as 510.2 and tested as 510.0.

Elemental analysis (JSL organic elemental analyzer JM1000, model: JM1000 CN/HCN/TOC/CN): theoretical value C,87.04; h,4.34; n,5.49; test value C,87.04; h,4.35; n,5.49.

Example 2

Synthesis of compound P4:

(1) P4-1 (0.5 mmol), P4-2 (0.5 mmol), K ₂ CO ₃ (0.5mmol)、PdCl ₂ (5×10 ^-4 mmol)、TPPDA(5×10 ^-4 mmol) was added to 3mL of o-xylene solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature and then saturated MgSO was slowly added to the solution ₄ The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the product P4-3.

(2) P4-3 (0.5 mmol), iodobenzene (0.5 mmol), bis-trifluoroacetyl iodobenzene (PIFA, 0.2 mmol), boron trifluoride etherate (BF) ₃ .OEt ₂ 0.2 mmol) was added to a 3mL solution of methylene chloride, mixed, placed in a 50mL flask, and reacted at-30℃for 3 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution ₄ The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the product P4-4.

(3) P4-4 (10 mmol), P4-5 (12 mmol), palladium acetate Pd (OAc) ₂ (0.3 mmol) and cesium carbonate Cs ₂ CO ₃ (12 mmol) was added to a mixture of N, N dimethylformamide (10 mL) and reacted under reflux under nitrogen atmosphere for 12h. Cooling the resulting mixtureTo room temperature, water was added, followed by filtration through celite pad, and the filtrate was extracted with ethyl acetate, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give product P4-6.

(4) Intermediate P4-6 (2 mmol), triethylamine Et in a 50mL round bottom flask ₃ N (3 mmol) and phosgene (6 mmol in toluene 10 mL) were added to dry 20mL toluene and stirred under nitrogen at 0deg.C for 1h, and the resulting mixture was then reacted at room temperature for 5h. Added to water, then filtered through a pad of celite, the filtrate extracted with dichloromethane, then washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product purified by silica gel column chromatography to give the product P4-7.

(5) Intermediate P4-7 (3 mmol), palladium acetate Pd (OAc) in a 50mL round bottom flask ₂ (1 mmol), triphenylphosphine PPh ₃ (1.2 mmol), norbornene NBE (3 mmol), CS ₂ CO ₃ (12 mmol) and dried dichloroethane (20 mL) were stirred under nitrogen at 95℃for 48 h. The intermediate obtained was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give compound P4.

The structure of the target product P4 was tested: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) ₃₇ H ₂₁ NO ₂ Calculated 511.2 and tested 511.1.

Elemental analysis (JSL organic elemental analyzer JM1000, model: JM1000 CN/HCN/TOC/CN): theoretical value C,86.87; h,4.14; n,2.74; test value C,86.87; h,4.15; n,2.74.

Example 3

Synthesis of Compound P7:

(1) P7-1 (0.5 mmol), iodobenzene (0.5 mmol), bis-trifluoroacetyl iodobenzene (PIFA)0.2 mmol), boron trifluoride etherate (BF) ₃ .OEt ₂ 0.2 mmol) was added to a 3mL solution of methylene chloride, mixed, placed in a 50mL flask, and reacted at-30℃for 3 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution ₄ The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the product P7-2.

(2) P7-2 (10 mmol), P7-3 (12 mmol), palladium acetate Pd (OAc) ₂ (0.3 mmol) and cesium carbonate Cs ₂ CO ₃ (12 mmol) was added to a mixture of N, N dimethylformamide (10 mL) and reacted under reflux under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a celite pad, the filtrate was extracted with ethyl acetate, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by silica gel column chromatography to give the product P7-4.

(3) Intermediate P7-4 (2 mmol), triethylamine Et in a 50mL round bottom flask ₃ N (3 mmol) and phosgene (6 mmol in toluene 10 mL) were added to dry 20mL toluene and stirred under nitrogen at 0deg.C for 1h, and the resulting mixture was then reacted at room temperature for 5h. Added to water, then filtered through a pad of celite, the filtrate extracted with dichloromethane, then washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product purified by silica gel column chromatography to give the product P7-5.

(4) Intermediate P7-5 (3 mmol), palladium acetate Pd (OAc) in a 50mL round bottom flask ₂ (1 mmol), triphenylphosphine PPh ₃ (1.2 mmol), norbornene NBE (3 mmol), CS ₂ CO ₃ (12 mmol) and dried dichloroethane (20 mL) were stirred under nitrogen at 95℃for 48 h. The intermediate obtained was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give compound P7.

Structure of test target product P7: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) ₃₀ H ₁₈ N ₂ O calculated 422.1 and tested 422.1.

Elemental analysis (JSL organic elemental analyzer JM1000, model: JM1000 CN/HCN/TOC/CN): theoretical value C,85.29; h,4.29; n,6.63; test value C,85.29; h,4.28; n,6.63.

Example 4

Synthesis of Compound P15:

(1) P15-1 (0.5 mmol), P15-2 (0.5 mmol), K ₂ CO ₃ (0.5mmol)、PdCl ₂ (5×10 ^-4 mmol)、TPPDA(5×10 ^-4 mmol) was added to 3mL of o-xylene solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature and then saturated MgSO was slowly added to the solution ₄ The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the product P15-3.

(2) P15-3 (0.5 mmol), 4-iodopyridine (0.5 mmol), bis-trifluoroacetyl iodobenzene (PIFA, 0.2 mmol), boron trifluoride diethyl etherate (BF) ₃ .OEt ₂ 0.2 mmol) was added to a 3mL solution of methylene chloride, mixed, placed in a 50mL flask, and reacted at-30℃for 3 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution ₄ The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the product P15-4.

(3) P15-4 (10 mmol), P15-5 (12 mmol), palladium acetate Pd (OAc) ₂ (0.3 mmol) and cesium carbonate Cs ₂ CO ₃ (12 mmol) was added to a mixture of N, N dimethylformamide (10 mL) and reacted under reflux under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a celite pad, the filtrate was extracted with ethyl acetate, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by silica gel column chromatography to give the product P15-6.

(4) Intermediate P15-6 (2 mmol), triethylamine Et in a 50mL round bottom flask ₃ N (3 mmol) and phosgene (6 mmol in toluene 10 mL) were added to dry 20mL toluene and stirred under nitrogen at 0deg.C for 1h, and the resulting mixture was then reacted at room temperature for 5h. Added to water, then filtered through a pad of celite, the filtrate extracted with dichloromethane, then washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product purified by silica gel column chromatography to give the product P15-7.

(5) Intermediate P15-7 (3 mmol), palladium acetate Pd (OAc) were placed in a 50mL round bottom flask ₂ (1 mmol), triphenylphosphine PPh ₃ (1.2 mmol), norbornene NBE (3 mmol), CS ₂ CO ₃ (12 mmol) and dried dichloroethane (20 mL) were stirred under nitrogen at 95℃for 48 h. The intermediate obtained was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give compound P15.

Structure of test target product P15: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: C35H20N4O calculated as 512.2 and tested as 512.1.

Elemental analysis (JSL organic elemental analyzer JM1000, model: JM1000 CN/HCN/TOC/CN): theoretical value C,82.01; h,3.93; n,10.93; test value C,82.00; h,3.92; n,10.93.

Example 5

Synthesis of Compound P40:

(1) P40-1 (0.5 mmol), iodobenzene (0.5 mmol), bis-trifluoroacetyl iodobenzene (PIFA, 0.2 mmol), boron trifluoride etherate (BF) ₃ .OEt ₂ 0.2 mmol) was added to a 3mL solution of methylene chloride, mixed, placed in a 50mL flask, and reacted at-30℃for 3 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution ₄ Aqueous solution and ethyl acetate extractionThe solvent was then removed from the organic layer by rotary evaporator and column chromatography was performed to give the product P40-2.

(2) P40-2 (10 mmol), P40-3 (12 mmol), palladium acetate Pd (OAc) ₂ (0.3 mmol) and cesium carbonate Cs ₂ CO ₃ (12 mmol) was added to a mixture of N, N dimethylformamide (10 mL) and reacted under reflux under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, then filtered through a celite pad, the filtrate was extracted with ethyl acetate, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by silica gel column chromatography to give product P40-4.

(3) Intermediate P40-4 (2 mmol), triethylamine Et in a 50mL round bottom flask ₃ N (3 mmol) and phosgene (6 mmol in toluene 10 mL) were added to dry 20mL toluene and stirred under nitrogen at 0deg.C for 1h, and the resulting mixture was then reacted at room temperature for 5h. Added to water, then filtered through a pad of celite, the filtrate extracted with dichloromethane, then washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product purified by silica gel column chromatography to give the product P40-5.

(4) Intermediate P40-5 (3 mmol), palladium acetate Pd (OAc) in a 50mL round bottom flask ₂ (1 mmol), triphenylphosphine PPh ₃ (1.2 mmol), norbornene NBE (3 mmol), CS ₂ CO ₃ (12 mmol) and dried dichloroethane (20 mL) were stirred under nitrogen at 95℃for 48 h. The intermediate obtained was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by column chromatography on silica gel to give compound P40.

Structure of test target product P40: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c (C) ₂₆ H ₁₄ N ₂ O calculated as 370.1 and tested as 370.1.

Elemental analysis (JSL organic elemental analyzer JM1000, model: JM1000 CN/HCN/TOC/CN): theoretical value C,84.31; h,3.81; n,7.56; test value C,84.31; h,3.80; n,7.56.

The preparation methods of the compounds of the present invention used in the specific embodiments are similar to the above methods, and are not described in detail, and only the characterization results thereof are provided, and the mass spectrometry and elemental analysis results are shown in table 1.

Comparative example 1: compound CI; comparative example 2: compound CII

TABLE 1

Analog calculation of compound energy levels

The compounds of each example and comparative example were subjected to simulated calculations of energy levels using Density Functional Theory (DFT). The distribution of molecular front orbitals HOMO and LUMO was optimized and calculated at the calculated B3LYP/6-31G (d) level by Gaussian 09 package (Gaussian inc.) while the lowest singlet energy level E of the compound was calculated based on time-dependent density functional theory (TDDFT) modeling _S1 And the lowest triplet energy level E _T1 . The results are shown in Table 2.

TABLE 2 simulation calculation results of chemical energy levels

As can be seen from Table 2, the compounds provided by the present invention have a more suitable HUMO energy level and LUMO energy level, and a higher minimum triplet energy level E _T1 (e.g., > 2.62 eV), the compound is suitable for green light host material and has deeper LUMO energy level<1.63 eV) can promote electron injection and improve luminous efficiency.

Application example 1

The present application example provides an OLED device (organic light emitting device) including, as shown in fig. 1, a substrate 1, an anode (ITO) 2, a hole injection layer 3, a first hole transport layer 41, a second hole transport layer 42, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, a cathode 8 (magnesium silver electrode, magnesium silver mass ratio 91:19), and a capping layer 9 (CPL) stacked in this order. The arrows in the figure indicate the light direction.

The specific preparation steps of the OLED device are as follows:

1) Cutting a glass substrate with an Indium Tin Oxide (ITO) anode (thickness of 15 nm) into a size of 50mm×50mm×0.7mm, respectively performing ultrasonic treatment in isopropanol and deionized water for 30 minutes, then exposing to ozone for about 10 minutes for cleaning, and mounting the cleaned glass substrate on a vacuum deposition device;

2) Co-evaporating a hole injection layer material (a compound b) and a p-doped material (a compound a) on the ITO anode layer by a vacuum evaporation mode, wherein the doping proportion is 3 percent (mass ratio); a thickness of 5nm as a hole injection layer;

3) Vacuum evaporating a hole transport material (compound c) with a thickness of 100nm on the hole injection layer as a first hole transport layer;

4) Vacuum evaporating a hole transport material (compound d) with a thickness of 5nm on the first hole transport layer as a second hole transport layer;

5) The light-emitting host material compound P3 and the compound e were vacuum co-deposited on the second hole transport layer (deposition ratio 1: 1) And a doping material compound f having a doping ratio of 3% (mass ratio) and a thickness of 30nm as a light-emitting layer;

6) Vacuum evaporating a compound g with a thickness of 30nm on the light-emitting layer to serve as an electron transport layer;

7) Vacuum co-evaporating a compound h and an n-doped material (compound i) on the electron transport layer, wherein the doping mass ratio is 1:1; a thickness of 5nm as an electron injection layer;

8) Vacuum evaporating a magnesium-silver electrode on the electron injection layer, wherein the mass ratio of Mg to Ag is 1:9, and the thickness is 10nm, and the magnesium-silver electrode is used as a cathode;

9) The compound j was vacuum-evaporated on the cathode to a thickness of 100nm as a cap layer.

Testing the currents of the OLED device under different voltages by using a Keithley 2365A digital nano-volt meter, and dividing the currents by the light emitting areas to obtain the current densities of the OLED device under different voltages; testing the brightness and radiant energy density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; according to the current density and brightness of the OLED device under different voltages, the OLED device with the same current density (10 mA/cm ² ) Operating Voltage and Current efficiency CE (10 mA/cm ² )(cd/A)，V _on For a luminance of 1cd/m ² A lower turn-on voltage; lifetime LT97 (at 50 mA/cm) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance ² Under test conditions; the test data are shown in table 3.

Table 3OLED device performance test results

As can be seen from Table 3, the display panel provided by the invention has lower driving voltage, higher luminous efficiency and longer service life due to the adoption of the compound of the invention as a green light main body material. For example, the turn-on voltage may be 4.41V or less; current efficiency CE (10 mA/cm) ² ) 140.6cd/A or more; the lifetime LT97 may be 275h or more. Compared with application comparative examples 1-2, the OLED devices provided by application examples 1-12 have the advantages that the organic compound provided by the invention has proper HOMO energy level, LUMO energy level and higher triplet energy level, and can improve the electron injection capability, so that the organic light-emitting device adopting the organic compound as green light main material has lower driving voltage and higher luminous efficiency; meanwhile, the organic compound provided by the invention also has good thermal stability and film forming property, is favorable for the stability of devices and prolongs the service life of the devices.

The applicant states that the process of the invention is illustrated by the above examples, but the invention is not limited to, i.e. does not mean that the invention must be carried out in dependence on the above process steps. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of selected raw materials, addition of auxiliary components, selection of specific modes, etc. fall within the scope of the present invention and the scope of disclosure.

Claims

1. An organic compound, characterized in that the organic compound comprises any one of the following compounds:

wherein D is deuterium.

2. An organic electroluminescent material, characterized in that it comprises the organic compound according to claim 1.

3. An OLED device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, wherein the material of the organic thin film layer comprises the organic compound of claim 1.

4. The OLED device according to claim 3, wherein the organic thin film layer includes a light-emitting layer including the organic compound according to claim 1 as a host material.

5. A display panel comprising the OLED device of claim 3 or 4.

6. An organic light-emitting display device comprising the display panel according to claim 5.

7. An electronic device comprising the display panel of claim 6.