CN114105996B - Organic compound and electroluminescent application thereof - Google Patents

Organic compound and electroluminescent application thereof Download PDF

Info

Publication number
CN114105996B
CN114105996B CN202111458598.5A CN202111458598A CN114105996B CN 114105996 B CN114105996 B CN 114105996B CN 202111458598 A CN202111458598 A CN 202111458598A CN 114105996 B CN114105996 B CN 114105996B
Authority
CN
China
Prior art keywords
organic compound
organic
independently selected
layer
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202111458598.5A
Other languages
Chinese (zh)
Other versions
CN114105996A (en
Inventor
邓东阳
过宇阳
刘营
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wuhan Tianma Microelectronics Co Ltd
Original Assignee
Wuhan Tianma Microelectronics Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wuhan Tianma Microelectronics Co Ltd filed Critical Wuhan Tianma Microelectronics Co Ltd
Priority to CN202111458598.5A priority Critical patent/CN114105996B/en
Publication of CN114105996A publication Critical patent/CN114105996A/en
Application granted granted Critical
Publication of CN114105996B publication Critical patent/CN114105996B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Abstract

The invention provides an organic compound, which has a structure shown in a formula I. The invention provides a novel organic compound taking an N-doped large ring structure as a central framework, the series of OLED materials have good thermal stability and film forming property, and proper glass transition temperature Tg, are favorable for forming a stable and uniform film in the thermal vacuum evaporation process, reduce phase separation, maintain the stability of a device, have higher carrier transmission rate and balanced carrier transmission performance, are favorable for balancing hole and electron transmission in the device, obtain a wider carrier composite area, can obviously improve the luminous efficiency and service life of the device, reduce driving voltage, and can be well applied in the technical field of electroluminescence.

Description

Organic compound and electroluminescent application thereof
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to an organic compound and electroluminescent application thereof.
Background
As a new generation display technology, the organic electroluminescent material (OLED) has the advantages of ultra-thin, self-luminescence, wide viewing angle, quick response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption and the like, and is widely applied to industries of flat panel display, flexible display, solid-state lighting, vehicle-mounted display and the like.
The luminescence mechanism can be divided into two types, namely electrofluorescence, which is the radiative decay transition of singlet excitons, and electrophosphorescence, which is the light emitted by the radiative decay of triplet excitons to the 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%. In 1998, the university of Jilin's horses in China and the university of Prlington's Forrest in U.S. reported the use of osmium complexes and platinum complexes as dyes doped into the light-emitting layer, respectively, were successful for the first time and explained the phosphorescent electroluminescence phenomenon, and the prepared phosphorescent materials were applied to electroluminescent devices at the beginning.
Since phosphorescent heavy metal materials have a long lifetime (μs) and can cause triplet-triplet annihilation and concentration quenching at high current densities, resulting in reduced device performance, heavy metal phosphorescent materials are typically doped into suitable host materials to form a host-guest doped system that optimizes energy transfer, maximizes luminous efficiency and lifetime. 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.
The current phosphorescent host materials often have the problems of insufficient service life, insufficient efficiency and higher driving voltage.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide an organic compound and an electroluminescent application thereof, wherein the organic compound can be used as a light-emitting main body material, which is helpful for improving efficiency and service life of an OLED device and reducing driving voltage.
The invention provides an organic compound, which has a structure shown in a formula I:
wherein R is 1 、R 2 Independently selected from substituted or non-substitutedSubstituted aryl or heteroaryl;
L 1 、L 2 independently selected from single bond, substituted or unsubstituted arylene or heteroarylene;
x, Y is independently selected from H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted aryl or heteroaryl, substituted or unsubstituted NR 3 R 4 ；
R 3 、R 4 Independently selected from substituted or unsubstituted arylene or heteroarylene;
n1 and n2 are independently integers selected from 1 to 3.
The invention provides a display panel, which comprises an organic light-emitting device, wherein the organic light-emitting device comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, the organic thin film layer comprises a light-emitting layer, and the light-emitting layer contains at least one organic compound.
The invention provides a display device which comprises the display panel.
Compared with the prior art, the invention provides an organic compound which has a structure shown in a formula I. The invention provides a novel organic compound taking an N-doped large ring structure as a central framework, the series of OLED materials have good thermal stability and film forming property, and proper glass transition temperature Tg, are favorable for forming a stable and uniform film in the thermal vacuum evaporation process, reduce phase separation, maintain the stability of a device, have higher carrier transmission rate and balanced carrier transmission performance, are favorable for balancing hole and electron transmission in the device, obtain a wider carrier composite area, can obviously improve the luminous efficiency and service life of the device, reduce driving voltage, and can be well applied in the technical field of electroluminescence.
Drawings
Fig. 1 is a schematic structural view of an organic light emitting device according to the present invention.
Detailed Description
The invention provides an organic compound, which has a structure shown in a formula I:
wherein R is 1 、R 2 Independently selected from substituted or unsubstituted aryl or heteroaryl;
L 1 、L 2 independently selected from single bond, substituted or unsubstituted arylene or heteroarylene;
x, Y is independently selected from H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted aryl or heteroaryl, substituted or unsubstituted NR 3 R 4 ；
R 3 、R 4 Independently selected from substituted or unsubstituted arylene or heteroarylene;
n1 and n2 are independently integers selected from 1 to 3.
Alternatively, the aryl, heteroaryl, arylene, heteroarylene, C1-C10 alkyl, NR 3 R 4 Is independently selected from deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted aryl or heteroaryl, substituted or unsubstituted NR 4 R 5 One or more of the following;
R 4 、R 5 independently selected from substituted or unsubstituted aryl or heteroaryl groups.
Alternatively, the aryl, heteroaryl, arylene, heteroarylene, C1-C10 alkyl, NR 3 R 4 Independently selected from one or more of deuterium, phenyl, naphthyl, anthryl, phenanthryl, pyridyl, carbazolyl, methyl, ethyl, N-propyl, isopropyl, N-butyl, isobutyl, tert-butyl, N-diphenylamino.
Optionally, the R 1 、R 2 Independently selected from one or more of substituted or unsubstituted phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl and quinoxalinyl.
Optionally, the R 1 、R 2 Independently selected from any one of the following structures:
# denotes a connection position.
Optionally, the L 1 、L 2 Independently selected from one or more of single bond, phenylene, naphthylene and anthrylene.
Optionally, the L 1 、L 2 Independently selected from a single bond or any of the following structures:
# denotes a connection position.
Optionally, the X, Y is independently selected from one or more of H, substituted or unsubstituted phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, carbazolyl, acridinyl, phenanthrolinyl, N-diphenylamino, indolocarbazolyl.
Optionally, the X, Y is independently selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, or any of the following structures:
# denotes a connection position.
Optionally, the organic compound has any one of the following structures:
/>
/>
/>
/>
/>
/>
/>
the organic compound provided by the invention can be used as a main body material of an organic photoelectric device, and partial compound is also expected to be used as an electron transport layer material.
The invention provides a display panel, which comprises an organic light-emitting device, wherein the organic light-emitting device comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, the organic thin film layer comprises a light-emitting layer, and the light-emitting layer contains at least one organic compound.
The invention provides a display panel, which comprises an organic light-emitting device, wherein the organic light-emitting device comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, the organic thin film layer comprises an electron transport layer, and the electron transport layer contains at least one organic compound.
The invention also provides a display panel comprising an organic light-emitting device, wherein the organic light-emitting device comprises an anode, a cathode and a light-emitting layer positioned between the anode and the cathode, and the light-emitting material of the light-emitting layer comprises one or more than one of the compounds.
According to one embodiment of the display panel of the present invention, the light-emitting material of the light-emitting layer includes a host material and a guest material, and the host material is one or more of the compounds of the present invention.
According to an embodiment of the display panel of the invention, the light emitting layer comprises a red light emitting layer, and the host material is a red host material.
According to an embodiment of the display panel of the invention, the light emitting layer comprises a green light emitting layer, and the host material is a green host material.
The organic light-emitting device provided by the invention can be an organic light-emitting device well known to a person skilled in the art, and optionally comprises a substrate, an ITO anode, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light-emitting layer, a first electron transport layer, a second electron transport layer, a cathode (magnesium-silver electrode, magnesium-silver mass ratio of 1:9) and a capping layer (CPL).
Alternatively, the anode material of the organic light-emitting device may be selected from metal-copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc., and alloys thereof; such as metal oxide-indium oxide, zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and the like; such as the conductive polymers polyaniline, polypyrrole, poly (3-methylthiophene), and the like, include materials known to be suitable as anodes in addition to facilitating hole injection materials and combinations thereof.
The cathode material of the organic light-emitting device can be selected from metal-aluminum, magnesium, silver, indium, tin, titanium and the like and alloys thereof; such as multi-layer metal material 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.
The organic optoelectronic device, such as an organic light emitting device, has at least one light emitting layer (EML), and may further include other functional layers including 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), and an Electron Injection Layer (EIL).
According to the invention, the organic light-emitting device is prepared according to 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.
Alternatively, the organic thin layer may be formed by known film forming methods such as evaporation, sputtering, spin coating, dipping, ion plating, and the like.
The invention provides a display device which comprises the display panel.
In the present invention, an organic light emitting device (OLED device) may be used in a display apparatus, wherein the organic light emitting display apparatus may be a mobile phone display screen, a computer display screen, a television display screen, a smart watch display screen, a smart car display panel, a VR or AR helmet display screen, display screens of various smart devices, or the like.
The following description of embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is shown, however, only some, but not all embodiments of the invention are shown. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The organic compound with the structure shown in the formula I provided by the invention is prepared by the following synthetic route in an exemplary way:
/>
in the above synthetic route, R 1 、R 2 Each independently having the same defined ranges as in formula I;
EXAMPLE 1 Compound P7
The preparation method of the organic compound P7 comprises the following steps:
in a 250mL round bottom flask, reaction P7-1 (10 mmol), reaction A7 (21 mmol) and Na 2 CO 3 (80 mmol) added to toluene/EtOH (absolute ethanol)/H respectively 2 O (75/25/50, mL) in a solvent to form a mixed solution, and then Pd (PPh) 3 ) 4 (0.48 mmol) was added to the above mixed solution, and the intermediate obtained by conducting the reflux reaction under nitrogen atmosphere for 20 hours was cooled to room temperature, added to water, then filtered through a celite pad, extracted with methylene chloride, then washed with water, and dried with anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by silica gel column chromatography to give compound P7.
MALDI-TOF: m/z: calculated values: c (C) 65 H 44 N 6 908.36, measured values: 908.42.
compound elemental analysis results: calculated values: c (C) 65 H 44 N 6 (%) C,85.88; h,4.88; n,9.24; test value: c,85.88; h,4.87; n,9.24.
EXAMPLE 2 Compound P8
The preparation method of the organic compound P8 comprises the following steps:
the synthesis of compound P8 is similar to that of P7, except that reactant A7 is replaced with an equimolar amount of A8.
MALDI-TOF: m/z: calculated values: c (C) 49 H 30 N 4 674.25, measured values: 674.28.
compound elemental analysis results: calculated values: c (C) 49 H 30 N 4 C,87.22; h,4.48; n,8.30; test value: c,87.22; h,4.47; n,8.30.
EXAMPLE 3 Compound P9
The preparation method of the organic compound P9 comprises the following steps:
/>
the synthesis of compound P9 is similar to that of P7, except that reactant A7 is replaced with an equimolar amount of A9.
MALDI-TOF: m/z: calculated values: c (C) 57 H 34 N 4 774.28, measured values: 774.34.
compound elemental analysis results: calculated values: c (C) 57 H 34 N 4 (%) C,88.35; h,4.42; n,7.23; test value: c,88.35; h,4.43; n,7.23.
EXAMPLE 4 Compound P10
The preparation method of the organic compound P10 comprises the following steps:
tri-tert-butylphosphine (3 mL of 1.0M toluene solution, 7.32 mmol), palladium acetate (0.4 g,1.83 mmol) and sodium tert-butoxide (52.7 g,549 mmol) were added to a solution of P7-1 (183 mmol) and a10 (370 mmol) in degassed toluene (600 mL) and the mixture was heated at reflux for 2.5 hours. The reaction mixture was cooled to room temperature, diluted with toluene and filtered through celite. The filtrate was diluted with water and extracted with toluene, and the organic phases were combined and evaporated under vacuum. The residue was filtered through silica gel and recrystallized to give the objective compound P10.
MALDI-TOF: m/z: calculated values: c (C) 53 H 36 N 6 756.30, measured values: 756.36.
compound elemental analysis results: calculated values: c (C) 53 H 36 N 6 (%) C,84.10; h,4.79; n,11.10; test value: c,84.10; h,4.80; n,11.10.
EXAMPLE 5 Compound P11
The preparation method of the organic compound P11 comprises the following steps:
the synthesis of compound P11 is similar to that of P7, except that reactant A7 is replaced with an equimolar amount of a11.
MALDI-TOF: m/z: calculated values: c (C) 41 H 26 N 4 574.22, measured values: 574.26.
compound elemental analysis results: calculated values: c (C) 41 H 26 N 4 (%) C,85.69; h,4.56; n,9.75; test value: c,85.69; h,4.55; n,9.75.
Examples 6 to 15
The compounds shown in table 1 below were synthesized according to the similar method described above:
TABLE 1 preparation of Compounds of examples 6-15 and Structure
/>
/>
By applying Density Functional Theory (DFT), the organic compound provided by the invention optimizes and calculates the distribution condition of the molecular front-line orbitals HOMO and LUMO under the calculated level of B3LYP/6-31G (d) through a Guassian 09 program package (Guassian Inc.), and simultaneously calculates the singlet energy level E of the compound molecule based on the time-dependent density functional theory (TD-DFT) simulation S And triplet energy level E T The calculation results are shown in table 2.
TABLE 2 Gaussian simulation calculation results of organic Compounds
As can be seen from Table 2, the compounds provided by the invention have more proper HOMO energy levels and LUMO energy levels, are favorable for energy level matching of adjacent layer compounds, and realize efficient exciton recombination. Singlet energy level E S And triplet energy level E T The device is relatively high, can be well matched with the energy level of the adjacent layer material used in the existing mass production, effectively transmits electrons and holes, limits the holes and excitons to a light-emitting area, is beneficial to widening the light-emitting area, and improves the light-emitting efficiency and service life of the device. Is suitable for being used as OLED materials.
Device example 1
The embodiment provides an OLED device, as shown in fig. 1, fig. 1 is a schematic structural diagram of an organic light emitting device provided by the present invention, which includes a substrate 1, an anode 2, a first hole transport layer 3, a second hole transport layer 4, a light emitting layer 5, a first electron transport layer 6, a second electron transport layer 7, a cathode 8, and a cap layer 9 that are sequentially stacked. Wherein, the anode of Indium Tin Oxide (ITO) is 15nm, the first hole transport layer is 10nm, the second hole transport layer is 95nm, the luminescent layer is 30nm, the first electron transport layer is 35nm, the second electron transport layer is 5nm, the cathode is 15nm (magnesium silver electrode, the mass ratio of magnesium silver is 1:9), and the capping layer (CPL) is 100nm.
The OLED device was prepared as follows:
(1) Cutting the glass substrate 1 into a size of 50mm×50mm×0.7mm, respectively performing ultrasonic treatment in isopropanol and deionized water for 30min, and then exposing to ozone for cleaning for 10min; mounting the glass substrate with the ITO anode 2 obtained by magnetron sputtering on a vacuum deposition apparatus;
(2) Vacuum evaporating compound HAT-CN with thickness of 10nm on ITO anode layer 2 under vacuum degree of 2×10-6Pa to obtain first hole transport layer 3;
(3) Vacuum evaporating a compound TAPC on the first hole transport layer 3 as a second hole transport layer 4, wherein the thickness is 95nm;
(4) Vacuum vapor deposition of a light-emitting layer 5 on the second hole-transporting layer 4, using the organic compound P7 provided by the present invention as a host material, ir (piq) 2 (acac) as doping materials, P7 and Ir (piq) 2 (acac) 97:3 by mass and 30nm thick;
(5) Vacuum evaporating compound BCP as the first electron transport layer 6 on the light emitting layer, wherein the thickness is 35nm;
(6) Vacuum evaporation of a compound Alq on the first electron transport layer 6 3 As the second electron transport layer 7, the thickness was 5nm;
(7) Vacuum evaporating a magnesium-silver electrode on the second electron transport layer 7 to serve as a cathode 8, wherein the mass ratio of Mg to Ag is 1:9, and the thickness is 15nm;
(8) The high refractive index compound CBP was vacuum deposited on the cathode 8 to a thickness of 100nm, and used as a cathode coating layer (cap layer) 9.
The structure of the compound used in the OLED device is as follows:
device examples 2 to 15
The organic compound P7 in the step (4) in the device example 1 was replaced with an equivalent amount of the compound P8, P9, P10, P11, P1, P6, P33, P46, P75, P86, P92, P99, P100 or P135, respectively, and the other preparation steps were the same as those of the application example 1.
Device comparative example
An OLED device differing from device example 1 only in that the organic compound P7 in step (4) was replaced with an equivalent amount of the comparative compound P0Replacement; other raw materials and preparation steps are the same.
Performance evaluation of OLED device:
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 on-voltage and current efficiency (Cd/A), von is luminance 1Cd/m 2 A lower turn-on voltage; obtaining a lifetime LT95 by measuring a time when the luminance of the OLED device reaches 95% of the initial luminance; the specific data are shown in Table 3.
Table 3 results of performance evaluation of OLED devices
As can be seen from table 3, the organic light emitting device provided by the present invention has lower driving voltage, higher luminous efficiency, and longer lifetime. The properties are significantly improved over the comparative examples, which are mainly due to the special condensed ring structure of the material of the invention, which results in less overlap of the HOMO and LUMO energy levels of the molecules. Different substituent groups are connected at the L1 and L2 positions, so that the spatial configuration of the whole molecule is more three-dimensional, the acting force of the molecule can be reduced, the stacking among molecules is reduced, concentration quenching is reduced, the dissolution performance of the material can be improved to a certain extent, mass production is facilitated, and meanwhile, the matching with other functional layers with different structures can be realized through adjusting the substituent groups.
The above description of the embodiments is only for aiding in the understanding of the method of the present invention and its core ideas. It should be noted that it will be apparent to those skilled in the art that various modifications and adaptations of the invention can be made without departing from the principles of the invention and these modifications and adaptations are intended to be within the scope of the invention as defined in the following claims.

Claims (8)

1. An organic compound having the structure of formula i:
wherein R is 1 Selected from phenyl, biphenyl or quinolinyl;
R 2 selected from phenyl or biphenyl;
L 1 、L 2 independently selected from a single bond or phenylene;
x, Y is independently selected from substituted or unsubstituted phenyl, naphthyl, phenanthryl, carbazolyl, N-diphenylamino or indolocarbazolyl;
the substituent in X, Y is independently selected from phenyl, methyl, tertiary butyl or carbazolyl;
n1 and n2 are independently selected from 1 or 2.
2. The organic compound according to claim 1, wherein R 1 Selected from any one of the following structures:
the R is 2 Selected from any one of the following structures:
# denotes a connection position.
3. The organic compound according to claim 1, wherein L 1 、L 2 Independently selected from a single bond or any of the following structures:
# denotes a connection position.
4. The organic compound according to claim 1, wherein the X, Y is independently selected from any one of the following structures:
# denotes a connection position.
5. The organic compound according to claim 1, having any one of the following structures:
6. a display panel comprising an organic light-emitting device comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode, the organic thin film layer comprising a light-emitting layer containing at least one organic compound according to any one of claims 1 to 5.
7. A display panel comprising an organic light-emitting device comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode, the organic thin film layer comprising an electron transport layer comprising at least one organic compound of any one of claims 1-5.
8. A display device comprising the display panel of any one of claims 6 to 7.
CN202111458598.5A 2021-12-01 2021-12-01 Organic compound and electroluminescent application thereof Active CN114105996B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111458598.5A CN114105996B (en) 2021-12-01 2021-12-01 Organic compound and electroluminescent application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111458598.5A CN114105996B (en) 2021-12-01 2021-12-01 Organic compound and electroluminescent application thereof

Publications (2)

Publication Number Publication Date
CN114105996A CN114105996A (en) 2022-03-01
CN114105996B true CN114105996B (en) 2023-08-18

Family

ID=80366259

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111458598.5A Active CN114105996B (en) 2021-12-01 2021-12-01 Organic compound and electroluminescent application thereof

Country Status (1)

Country Link
CN (1) CN114105996B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114773355B (en) * 2022-05-20 2024-01-05 武汉天马微电子有限公司 N-containing organic compound and electroluminescent application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107074896A (en) * 2014-08-08 2017-08-18 Udc 爱尔兰有限责任公司 Electroluminescent imidazoquinoxalines carbene metal complex compound
WO2021151922A1 (en) * 2020-01-29 2021-08-05 Merck Patent Gmbh Benzimidazole derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107074896A (en) * 2014-08-08 2017-08-18 Udc 爱尔兰有限责任公司 Electroluminescent imidazoquinoxalines carbene metal complex compound
WO2021151922A1 (en) * 2020-01-29 2021-08-05 Merck Patent Gmbh Benzimidazole derivatives

Also Published As

Publication number Publication date
CN114105996A (en) 2022-03-01

Similar Documents

Publication Publication Date Title
CN113443998B (en) Triarylamine organic compound and organic light-emitting device thereof
CN112321646B (en) Organic compound, electroluminescent material and application thereof
CN113816979B (en) Organic compound and electroluminescent application thereof
CN111892607B (en) N-heterobiphenyl organic compound and application thereof
CN110041357B (en) Compound, display panel and display device
CN113735891B (en) Organic compound and application thereof
CN110256428B (en) Compound, OLED display panel and display device
CN110128403B (en) Compound, display panel and display device
CN111559978B (en) Organic compound, electroluminescent material and application thereof
CN110615809B (en) Compound, display panel and display device
CN114105996B (en) Organic compound and electroluminescent application thereof
CN111808127B (en) Compound, display panel and display device
US11349082B2 (en) Compound, organic electroluminescent device and display device
CN114478574B (en) Organic compound and application thereof
CN114437087B (en) N-containing organic compound and application thereof in organic light-emitting device and panel
CN113801117B (en) Organic compound and electroluminescent application thereof
CN113173932B (en) Organic compound and electroluminescent application thereof
CN111285877A (en) Organic electroluminescent material and device
CN114436754A (en) Organic compound and application thereof
CN113563381A (en) Organic electroluminescent compound and application thereof
CN113292584A (en) Organic compound containing boron and nitrogen and electroluminescent application thereof
CN114805390B (en) Organic compound and electroluminescent application thereof
CN111606866A (en) Organic compound and electroluminescent application thereof
CN114773355B (en) N-containing organic compound and electroluminescent application thereof
CN111377904A (en) Organic electroluminescent material and device

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant