CN114560809B - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN114560809B
CN114560809B CN202210215474.2A CN202210215474A CN114560809B CN 114560809 B CN114560809 B CN 114560809B CN 202210215474 A CN202210215474 A CN 202210215474A CN 114560809 B CN114560809 B CN 114560809B
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organic compound
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CN114560809A (en
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代文朋
高威
翟露
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Wuhan Tianma Microelectronics Co Ltd
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Wuhan Tianma Microelectronics Co Ltd
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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.
To achieve the purpose, 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 each X 1-X12 is independently selected from N OR CR a,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 1;
R 1 is a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 cycloalkyl group;
l is selected from a bond, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl; n is an integer of 0 to 3;
ar is selected from the group consisting of substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
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.
In the present invention, n is an integer of 0 to 3, for example 0, 1,2 or 3.
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 ITO 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 9, and the arrow direction indicates the light direction.
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.
It is an object of the present invention to provide an organic compound having a structure represented by the following formula I:
wherein each X 1-X12 is independently selected from N OR CR a,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 1;
R 1 is a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 cycloalkyl group;
l is selected from a bond, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C3-C30 heteroaryl; n is an integer of 0 to 3;
ar is selected from the group consisting of substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.
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.
In the present invention, n is an integer of 0 to 3, for example 0, 1,2 or 3.
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-X12 is each CR a,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.
In one embodiment, at least one of X 1-X12 is N.
In one embodiment, L is selected from a single bond, phenylene, biphenylene, or naphthylene.
In one embodiment, ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridinyl, or substituted or unsubstituted triazinyl;
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:
Wherein D represents deuterium.
In the present invention, the preparation method of the organic compound is as follows:
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.
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 and the like and alloys thereof, and the multilayer metal material comprises LiF/Al, liO 2/Al、BaF2/Al and the like. 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.
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.
The following are illustrative examples of the preparation of the organic compounds according to the invention:
example 1
Synthesis of Compound P1:
(1) Intermediate P1-1 (15 mmol), potassium acetate (40 mmol) were mixed with dried 1, 4-dioxane (60 mL), bis (triphenylphosphine) palladium dichloride Pd (PPh 3)2Cl2 (0.4 mmol) and pinacolato-diboronate (25 mmol) in a 250mL round bottom flask and stirred under nitrogen for 48 hours at 90℃the resulting intermediate was cooled to room temperature, added to water and filtered through a pad of celite, the filtrate extracted with dichloromethane and washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated and the crude product purified by silica gel column chromatography to give intermediate P1-2.
(2) Intermediate P1-2 (10 mmol), compound 1, 8-diiodonaphthalene (12 mmol) and tetrakis (triphenylphosphine) palladium Pd (PPh 3)4 (0.3 mmol) were added to a mixture of toluene (30 mL)/potassium carbonate (12 mmol) in water (10 mL) in a 250mL round bottom flask and reacted under reflux under nitrogen for 12h.
(3) Intermediate P1-3 (10 mmol), triethylamine Et 3 N (12 mmol) and phosgene (30 mmol in toluene 30 mL) were added to dry 50mL toluene in a 250mL round bottom flask 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 desired product P1-4.
(4) Intermediate P1-4 (15 mmol), palladium acetate Pd (OAc) 2 (2 mmol), triphenylphosphine PPh 3 (4 mmol), norbornene NBE (15 mmol), CS 2CO3 (60 mmol) and dried dichloroethane (60 mL) were stirred in a 250mL round bottom flask at 95℃under nitrogen for 48 hours. 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 P1.
The structure of the target product P1 was tested: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c 29H17 NO calculated as 395.1 and tested as 395.0.
Elemental analysis (JSL organic elemental analyzer JM1000, model: JM1000 CN/HCN/TOC/CN): theoretical value C,88.08; h,4.33; n,3.54; test value C,88.08; h,4.32; n,3.54.
Example 2
Synthesis of Compound P8:
(1) Intermediate P8-1 (15 mmol), potassium acetate (40 mmol) were mixed with dried 1, 4-dioxane (60 mL), bis (triphenylphosphine) palladium dichloride Pd (PPh 3)2Cl2 (0.4 mmol) and pinacolato-diboronate (25 mmol) in a 250mL round bottom flask and stirred under nitrogen for 48 hours at 90℃the intermediate obtained was cooled to room temperature, added to water and filtered through a pad of celite, the filtrate extracted with dichloromethane and washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated and the crude product purified by silica gel column chromatography to give intermediate P8-2.
(2) Intermediate P8-2 (10 mmol), 1, 8-diiodonaphthalene (12 mmol) and Pd tetrakis (triphenylphosphine) palladium (PPh 3)4 (0.3 mmol)) were added to a mixture of toluene (30 mL)/aqueous potassium carbonate (12 mmol) in a 250mL round-bottomed flask and reacted under reflux under nitrogen for 12h the resulting mixture was cooled to room temperature, added to water and filtered through a pad of celite, the filtrate extracted with dichloromethane and 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 the desired product P8-3.
(3) Intermediate P8-3 (10 mmol), et 3 N (12 mmol) and phosgene (30 mmol in toluene 30 mL) were added to dry 50mL toluene in a 250mL round bottom flask 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 desired product P8-4.
(4) Intermediate P8-4 (15 mmol), pd (OAc) 2(2mmol)、PPh3(4mmol)、NBE(15mmol)、CS2CO3 (60 mmol) and dried dichloroethane (60 mL) were stirred in a 250mL round bottom flask at 95℃under nitrogen for 48 hours. 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 intermediate P8.
Structure of test target product P8: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c 34H20N2 O calculated 472.2 and tested 472.1.
Elemental analysis: theoretical value C,86.42; h,4.27; n,5.93; test value C,86.41; h,4.27; n,5.93.
Example 3
Synthesis of Compound P13:
(1) Intermediate P13-1 (15 mmol), potassium acetate (40 mmol) were mixed with dried 1, 4-dioxane (60 mL), bis (triphenylphosphine) palladium dichloride Pd (PPh 3)2Cl2 (0.4 mmol) and pinacolato-diboronate (25 mmol) in a 250mL round bottom flask and stirred under nitrogen for 48 hours at 90℃the intermediate obtained was cooled to room temperature, added to water and filtered through a pad of celite, the filtrate extracted with dichloromethane and washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated and the crude product purified by silica gel column chromatography to give intermediate P13-2.
(2) Intermediate P13-2 (10 mmol), 1, 8-diiodonaphthalene (12 mmol) and Pd tetrakis (triphenylphosphine) palladium (PPh 3)4 (0.3 mmol)) were added to a mixture of toluene (30 mL)/aqueous potassium carbonate (12 mmol) in a 250mL round-bottomed flask and reacted under reflux under nitrogen for 12h the resulting mixture was cooled to room temperature, added to water and filtered through a pad of celite, the filtrate extracted with dichloromethane and 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 the desired product P13-3.
(3) Intermediate P13-3 (10 mmol), et 3 N (12 mmol) and phosgene (30 mmol in toluene 30 mL) were added to dry 50mL toluene in a 250mL round bottom flask 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 was extracted with dichloromethane, then washed with water and dried over anhydrous magnesium sulfate, after filtration and evaporation, the crude product was purified by silica gel column chromatography to give the desired product P13-4.
(4) Intermediate P13-4(15mmol)、Pd(OAc)2(2mmol)、PPh3(4mmol)、NBE(15mmol)、CS2CO3(60mmol) was stirred with dry dichloroethane (60 mL) in a 250mL round bottom flask under nitrogen at 95 ℃ for 48 hours. 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 intermediate P13.
The structure of the target product P1 was tested: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c 28H16N2 O calculated 396.1 and tested 396.2.
Elemental analysis: theoretical value C,84.83; h,4.07; n,7.07; test value C,84.83; h,4.08; n,7.07.
Example 4
Synthesis of compound P24:
(1) P24-1(0.5mmol)、P24-2(0.5mmol)、K2CO3(0.6mmol)、PdCl2(5×10-4mmol)、TPPDA(5×10-4mmol) was added to 3mL of an o-xylene solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature, then saturated aqueous MgSO 4 and ethyl acetate were slowly added to the solution and extracted three times, then the organic layer was freed from the solvent by rotary evaporator and the crude product P24-3 was obtained by column chromatography.
(2) Intermediate P24-3 (15 mmol), potassium acetate (40 mmol) were mixed with dried 1, 4-dioxane (60 mL), bis (triphenylphosphine) palladium dichloride Pd (PPh 3)2Cl2 (0.4 mmol) and pinacolato-diboronate (25 mmol) in a 250mL round bottom flask and stirred under nitrogen for 48 hours at 90℃the resulting intermediate was cooled to room temperature, added to water and filtered through a pad of celite, the filtrate extracted with dichloromethane and washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated and the crude product purified by silica gel column chromatography to give intermediate P24-4.
(3) Intermediate P24-4 (10 mmol), 1, 8-diiodonaphthalene (12 mmol) and Pd tetrakis (triphenylphosphine) palladium (PPh 3)4 (0.3 mmol) were added to a mixture of toluene (30 mL)/aqueous potassium carbonate (12 mmol) in a 250mL round-bottomed flask and reacted under reflux under nitrogen for 12h the resulting mixture was cooled to room temperature, added to water and filtered through a pad of celite, the filtrate extracted with dichloromethane and 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 the desired product P24-5.
(4) Intermediate P24-5 (10 mmol), et 3 N (12 mmol) and phosgene (30 mmol in toluene 30 mL) were added to dry 50mL toluene in a 250mL round bottom flask 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 desired product P24-6.
(5) Intermediate P24-6(15mmol)、Pd(OAc)2(2mmol)、PPh3(4mmol)、NBE(15mmol)、CS2CO3(60mmol) was stirred with dry dichloroethane (60 mL) in a 250mL round bottom flask under nitrogen at 95 ℃ for 48 hours. 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 intermediate P26.
Structure of test target product P26: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c 33H19N3 O calculated 473.2 and tested 473.1.
Elemental analysis: theoretical value C,83.70; h,4.04; n,8.87; test value C,83.70; h,4.05; n,8.87.
Example 5
Synthesis of Compound P29:
(1) Intermediate P29-1 (15 mmol), potassium acetate (40 mmol) were mixed with dried 1, 4-dioxane (60 mL), bis (triphenylphosphine) palladium dichloride Pd (PPh 3)2Cl2 (0.4 mmol) and pinacolato-diboronate (25 mmol) in a 250mL round bottom flask and stirred under nitrogen for 48 hours at 90℃the intermediate obtained was cooled to room temperature, added to water and filtered through a pad of celite, the filtrate extracted with dichloromethane and washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated and the crude product purified by silica gel column chromatography to give intermediate P29-2.
(2) Intermediate P29-2 (10 mmol), P29-3 (12 mmol) and tetrakis (triphenylphosphine) palladium Pd (PPh 3)4 (0.3 mmol)) were added to a mixture of toluene (30 mL)/potassium carbonate (12 mmol) in water (10 mL) in a 250mL round bottom flask and reacted under reflux under nitrogen for 12h.
(3) Intermediate P29-4 (10 mmol), et 3 N (12 mmol) and phosgene (30 mmol in toluene 30 mL) were added to dry 50mL toluene in a 250mL round bottom flask 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 was extracted with dichloromethane, then washed with water and dried over anhydrous magnesium sulfate, after filtration and evaporation, the crude product was purified by silica gel column chromatography to give the desired product P29-5.
(4) Intermediate P29-5(15mmol)、Pd(OAc)2(2mmol)、PPh3(4mmol)、NBE(15mmol)、CS2CO3(60mmol) was stirred with dry dichloroethane (60 mL) in a 250mL round bottom flask under nitrogen at 95 ℃ for 48 hours. 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 intermediate P29.
Structure of test target product P29: MALDI-TOF MS (m/z) was obtained by matrix assisted laser desorption ionization time-of-flight mass spectrometry: c 35H29 NO calculated 479.2 and tested 479.1.
Elemental analysis: theoretical value C,87.65; h,6.09; n,2.92; test value C,87.65; h,6.10; n,2.92.
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). Distribution of molecular front orbitals HOMO and LUMO was optimized and calculated at the calculated level of B3LYP/6-31G (d) by Gaussian 09 package (Gaussian inc.) while the lowest singlet energy level E S1 and the lowest triplet energy level E T1 of the compound were calculated based on time-dependent density functional theory (TDDFT) simulations. The results are shown in Table 2.
TABLE 2 simulation calculation results of chemical energy levels
As can be seen from Table 2, the compound provided by the invention has more proper HUMO energy levels and LUMO energy levels, and higher lowest triplet energy level E T1 (for example > 2.26 eV), is suitable for being used as a red light main body material, has deeper LUMO energy levels (< 1.67 eV) and 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 P1 and the compound e (vapor 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 Konicaminolta CS-2000 spectroradiometer; the operating voltage and current efficiency CE (10 mA/cm 2)(cd/A),Von is the on-voltage at luminance 1cd/m 2; lifetime LT95 (under 50mA/cm 2 test conditions) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance) at the same current density (10 mA/cm 2) was obtained from the current densities and luminance of the OLED device at different voltages, and the test data are shown in Table 3.
TABLE 3 OLED 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 red light main body material. For example, the turn-on voltage may be 3.82V or less; the current efficiency CE (10 mA/cm 2) may be 38.0cd/A or more; the lifetime LT95 may be 100h or more. Compared with application comparative examples 1-2, the OLED devices provided by application examples 1-16 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 a red 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 organic compounds of the present invention and their use are illustrated by the above examples, but the present invention is not limited to, i.e. it is not meant that the present invention must be practiced in dependence upon the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.

Claims (10)

1. An organic compound, characterized in that the organic compound has a structure represented by the following formula I:
Wherein each X 1-X12 is independently selected from N OR CR a,Ra is hydrogen, C1-C10 alkyl, C1-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, OR 1, OR SR 1;
R 1 is C1-C10 alkyl;
l is selected from a single bond, phenylene, biphenylene, or naphthylene;
n is 1;
Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl or substituted or unsubstituted triazinyl;
The substituent in the substituted phenyl, substituted naphthyl, substituted phenanthryl, substituted fluorenyl, substituted pyridyl or substituted triazinyl is C1-C10 alkyl or C6-C30 aryl.
2. The organic compound according to claim 1, wherein X 1-X12 is each CR a,Ra hydrogen, C1-C10 alkyl, C1-C10 cycloalkyl, =c 6-C30 aryl, C3-C30 heteroaryl.
3. The organic compound according to claim 1, wherein at least one of X 1-X12 is N.
4. An organic compound, characterized in that the organic compound is any one of the following compounds:
Wherein D represents deuterium.
5. An organic electroluminescent material, characterized in that it comprises an organic compound according to any one of claims 1 to 4.
6. 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 any of claims 1-4.
7. The OLED device according to claim 6, wherein the organic thin film layer includes a light-emitting layer including the organic compound according to any one of claims 1 to 4 as a host material.
8. A display panel comprising an OLED device as claimed in any one of claims 6 or 7.
9. An organic light-emitting display device comprising the display panel according to claim 8.
10. An electronic device comprising the display panel of claim 8.
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Citations (8)

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