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CN114621142B - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN114621142B
CN114621142B CN202210326906.7A CN202210326906A CN114621142B CN 114621142 B CN114621142 B CN 114621142B CN 202210326906 A CN202210326906 A CN 202210326906A CN 114621142 B CN114621142 B CN 114621142B
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layer
organic
compound
transport layer
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CN114621142A (en
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刘营
姜东�
邓东阳
高威
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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, which has a structure shown in a formula I; in the formula I, n1, n2 and n3 are independently selected from 0 to 2, and n1, n2 and n3 are not 0 at the same time; a1, A2 and A3 are independently selected from aryl or substituted aryl, heteroaryl or substituted heteroaryl; x1 and X2 are independently selected from hydrogen or deuterium. The invention provides a series of novel organic compounds taking an azacyclic structure as a central skeleton, which have higher glass transition temperature and thermal stability, are easy to form a good amorphous film, can reduce driving voltage, improve the luminous efficiency and service life of the device, and can be well applied to the technical field of electroluminescence. The invention also provides application of the organic compound.

Description

Organic compound and application thereof
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, in particular to an organic compound and application thereof, and particularly relates to a novel luminescent main material (Host) and application of the material in an organic photoelectric device.
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.
Organic electroluminescence is classified into two kinds of electroluminescence, namely, electroluminescence, which is a radiative decay transition of singlet excitons, and electroluminescence, which is light emitted from triplet excitons by radiative decay to the ground state, according to a luminescence mechanism. 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%. The performance of the OLED device is improved continuously, the structure and the manufacturing process of the OLED device are required to be innovated, and the photoelectric functional material in the OLED device is required to be researched and innovated continuously so as to prepare the functional material with higher performance. Based on this, the OLED materials community has been striving to develop new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
Disclosure of Invention
In view of the above, the present invention is directed to an organic compound and application thereof, and the organic compound provided by the present invention has higher efficiency and lifetime as a light emitting material for an electroluminescent device, and can reduce driving voltage.
The invention provides an organic compound, which has a structure shown in a formula I:
in the formula I, n1, n2 and n3 are independently selected from 0 to 2, and n1, n2 and n3 are not 0 at the same time;
a1, A2 and A3 are independently selected from aryl or substituted aryl, heteroaryl or substituted heteroaryl;
x1 and X2 are independently selected from hydrogen or deuterium.
In the present invention, the A1, A2 and A3 are preferably independently selected from the structures of formula II:
in the formula II, m is 0 to 3;
l is selected from phenyl or substituted phenyl, biphenyl or substituted biphenyl, naphthyl or substituted naphthyl, anthracenyl or substituted anthracenyl;
q is selected from aryl or substituted aryl, heteroaryl or substituted heteroaryl.
In the present invention, the m is preferably 0, 1,2 or 3, more preferably 1.
In the present invention, the L is preferably a phenyl group or a substituted phenyl group, more preferably a phenyl group.
In the present invention, Q is preferably selected from one of formulas III to VI:
in formula III, R is selected from hydrogen, aryl or substituted aryl, heteroaryl or substituted heteroaryl;
in formula IV, E is selected from alkyl or substituted alkyl, heteroatom, aryl or substituted aryl, heteroaryl or substituted heteroaryl;
in formula V, G is selected from hydrogen, aryl or substituted aryl, heteroaryl or substituted heteroaryl;
in formula VI, J is selected from aryl or substituted aryl, heteroaryl or substituted heteroaryl.
In the present invention, the R is preferably hydrogen, phenyl or substituted phenyl, more preferably hydrogen.
In the present invention, E is preferably selected from an alkyl group having 1 to 5 carbon atoms, O, S, phenyl or substituted phenyl, biphenyl or substituted biphenyl, more preferably an alkyl group having 3 carbon atoms, O, S or phenyl.
In the present invention, the G is preferably selected from hydrogen, a condensed ring group, a phenyl group or a substituted phenyl group, a biphenyl group or a substituted biphenyl group, more preferably selected from hydrogen, a condensed ring group, a substituted biphenyl group.
In the present invention, the J is preferably selected from phenyl or substituted phenyl, more preferably phenyl.
In the present invention, Q is preferably selected from one of formulas a to J:
in the present invention, the structure of formula I is preferably one of the following structures:
the method for preparing the organic compound is not particularly limited, and a person skilled in the art may prepare a compound having a desired structure according to chemical synthesis methods and synthesis reactions well known in the art according to the structure of the compound, and may specifically refer to the methods in examples.
The invention provides an organic electroluminescent material, comprising:
the organic compound according to the above technical scheme.
The present invention provides an organic photoelectric device, comprising:
the organic electroluminescent material disclosed by the technical scheme.
The structure of the organic photoelectric device is not particularly limited, and those skilled in the art can adopt the structure of the organic photoelectric device known in the art according to actual needs. In the present invention, the organic photoelectric device preferably includes:
an anode;
a cathode;
an organic thin film disposed between the anode and the cathode;
the organic film comprises the organic electroluminescent material according to the technical scheme.
In the present invention, the anode is preferably selected from a group consisting of a material that facilitates hole injection, a combination thereof, or other materials suitable as anodes, such as metals, alloys, metal oxides, conductive polymers, and the like; the metal is preferably selected from copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc.; the alloy is preferably selected from an alloy formed of two or more of copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and the like; the metal oxide is preferably selected from indium oxide, zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and the like; the conductive polymer is preferably selected from polyaniline, polypyrrole, poly (3-methylthiophene), and the like.
In the present invention, the cathode is preferably selected from a material facilitating electron injection, a combination thereof, or other materials suitable as a cathode, preferably selected from one or more of a simple metal, a metal alloy, or a multi-layered metal; the metal simple substance is preferably selected from aluminum, magnesium, silver, indium, tin or titanium; the alloy is preferably an alloy formed of two or more selected from aluminum, magnesium, silver, indium, tin and titanium; the multilayer metal preferably comprises:
an aluminum layer;
the metal layer is arranged on the surface of the aluminum layer;
the metal layer is preferably selected from LiF and LiO 2 、BaF 2 。
In the present invention, the multilayer metal is preferably selected from LiF/Al, liO 2 /Al、BaF 2 Al, etc.
In the present invention, the organic thin film preferably includes: a light emitting layer (EML); the light-emitting layer preferably includes:
the organic compound according to the above technical scheme.
In the present invention, the organic thin film preferably further comprises: functional layer.
In the present invention, the functional layer is preferably one or more selected from 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).
The composition of each layer in the organic thin film is not particularly limited, and a person skilled in the art can select a suitable composition to design the organic thin film according to actual needs.
In the present invention, the organic photoelectric device preferably includes:
a substrate;
an anode disposed on the surface of the substrate;
a first hole transport layer disposed on a surface of the anode;
a second hole transport layer disposed on a surface of the first hole transport layer;
an electron blocking layer disposed on the surface of the second hole transport layer;
the light-emitting layer is arranged on the surface of the electron blocking layer;
a first electron transport layer disposed on the surface of the light emitting layer;
the second electron transmission layer is arranged on the surface of the first electron transmission layer;
a cathode disposed on a surface of the second electron transport layer;
and the capping layer is arranged on the surface of the cathode.
In the present invention, the substrate is preferably a glass substrate, more preferably a glass substrate with an ITO anode; preferably washing and cleaning the substrate; the washing is preferably carried out by ultrasonic treatment in a reagent; the time of the ultrasonic treatment is preferably 20 to 40 minutes, more preferably 25 to 35 minutes, and most preferably 30 minutes; the reagent preferably comprises: isopropyl alcohol and water; the water is preferably deionized water; the cleaning is preferably carried out under ozone, and the exposure time is preferably 8 to 12 minutes, more preferably 10 minutes.
In the present invention, the anode is preferably ITO; the thickness of the anode is preferably 10 to 20nm, more preferably 13 to 17nm, and most preferably 15nm.
In the present invention, the material of the first hole transport layer is preferably HT-1 and HAT-CN, and the mass ratio of HT1 to HAT-CN is preferably (95-100): 2, more preferably (96 to 99): 2, most preferably 98:2. In the present invention, the thickness of the first hole transport layer is preferably 5 to 15nm, more preferably 8 to 12nm, and most preferably 10nm.
In the present invention, the material of the second hole transport layer is preferably HT-1; the thickness of the second hole transport layer is preferably 90 to 100nm, more preferably 93 to 97nm, and most preferably 95nm.
In the invention, the material of the electron blocking layer is preferably Prime-1; the thickness of the electron blocking layer is preferably 25 to 35nm, more preferably 28 to 32nm, and most preferably 30nm.
In the present invention, the material of the light emitting layer preferably includes: the organic compound and the doping material according to the technical scheme; the doping material is preferably Ir (piq) 2 (acac); the mass ratio of the organic compound to the doping material is preferably (15-25): 1, more preferably (18 to 22): 1, most preferably 19:1. in the present invention, the thickness of the light emitting layer is preferably 25 to 35nm, more preferably 28 to 32nm, and most preferably 30nm.
In the present invention, the material of the first electron transport layer is preferably ET-1; the thickness of the first electron transport layer is preferably 25 to 35nm, more preferably 28 to 32nm, and most preferably 30nm.
In the present invention, the material of the second electron transport layer is preferably LiF; the thickness of the second electron transport layer is preferably 3 to 7nm, more preferably 4 to 6nm, and most preferably 5nm.
In the invention, the cathode is preferably a silver-magnesium electrode, and the mass ratio of magnesium to silver in the silver-magnesium electrode is preferably (8-12): 1, more preferably (9 to 11): 1, most preferably 9:1, a step of; the thickness of the cathode is preferably 10 to 20nm, more preferably 13 to 17nm, and most preferably 15nm.
In the present invention, the component of the cap layer is preferably CPL-1; the thickness of the cap layer is preferably 80 to 120nm, more preferably 90 to 110nm, and most preferably 100nm.
In the present invention, the HAT-CN, HT-1, prime-1, ir (piq) 2 (acac), ET-1, CPL-1 have the following formula:
the method for preparing the organic photoelectric device is not particularly limited, and a person skilled in the art can prepare the organic photoelectric device according to a method well known in the field of organic photoelectric devices, such as forming an anode on a substrate, forming an organic thin film on the anode, and forming a cathode on the organic thin film; the substrate can be a transparent substrate or an opaque substrate; the methods for forming the anode, the organic thin film and the cathode may be film forming methods well known in the art such as evaporation, sputtering, spin coating, dipping, ion plating and the like.
In the present invention, the method for manufacturing an organic photoelectric device preferably includes:
cleaning and cleaning the glass substrate with the ITO anode;
vacuum evaporating a first hole transport layer material on the surface of the ITO anode to obtain a first hole transport layer;
vacuum evaporating a second hole transport layer material on the surface of the first hole transport layer to obtain a second hole transport layer;
vacuum evaporating an electron blocking layer material on the surface of the second hole transport layer to obtain an electron blocking layer;
codeposition luminescent layer material on the surface of the electron blocking layer to obtain a luminescent layer;
vacuum evaporating a first electron transport layer material on the surface of the light-emitting layer to obtain a first electron transport layer;
vacuum evaporating a second electron transport layer material on the surface of the first electron transport layer to obtain a second electron transport layer;
vacuum evaporating cathode material on the surface of the second electron transport layer to obtain a cathode;
vacuum evaporating high refractive index cavity type material (CPL-1) on the surface of the cathode to obtain cathode cover layer (cap layer or CPL).
The Host materials provided by the invention have good thermal stability and film forming property, and suitable glass transition temperature Tg, so that stable and uniform films can be formed in the thermal vacuum evaporation process, phase separation is reduced, and the stability of the device is maintained; the Organic Light Emitting Diode (OLED) device has higher carrier transmission rate and balanced carrier transmission performance, so that balance of hole and electron transmission in the device is facilitated, a wider carrier composite region is obtained, luminous efficiency is improved, efficiency and service life of the OLED device are improved, and driving voltage is reduced.
The organic compound provided by the invention takes the azacyclic structure as a central skeleton, has higher glass transition temperature and thermal stability, is easy to form a good amorphous film, can reduce driving voltage, improves the luminous efficiency and service life of the device, and can be well applied to the technical field of electroluminescence.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. 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.
Examples 1 to 7
The organic compound is prepared according to the following process route, comprising the following steps:
1) B-1 structural compound (9.3 mmol) and triethylamine (36 mmol) are dissolved in 65mL of anhydrous tetrahydrofuran, cooled to-35 ℃ under the protection of argon gas, stirred for 30 minutes, titanium tetrachloride (8.8 mmol) is slowly dripped into the tetrahydrofuran solution, a-1 structural compound (8.9 mmol) is added into the tetrahydrofuran solution once again, the molar ratio of the a-1 structural compound to the b-1 structural compound to the triethylamine to the titanium tetrachloride is 1:1.05:4:1, the obtained new solution is continuously stirred for 1 hour at the temperature of-35 ℃, then the temperature is slowly increased to room temperature, and stirring is continued for 12 hours; stopping the reaction, pouring the reaction mixture into deionized water, extracting with ethyl acetate, drying the organic phase, distilling to remove the solvent, separating the crude product by a silica gel chromatographic column, and vacuum drying to obtain an intermediate c-1 structural compound;
detection MALDI-TOF (m/z): calculated value C 23 H 12 BrCl 2 N:450.95, test value: 450.92.
2) The reaction solvent benzene, compound c-1 (2 mmol), and then dimethylethylenediamine (40 mol%) were added to a reaction flask under a nitrogen atmosphereKOT-Bu (4 mmol), heating to 120 ℃, and reacting for 18h; after the reaction was completed, cooled to room temperature, and dichloromethane/H was added 2 O was extracted, and the collected organic phase was extracted with anhydrous Na 2 SO 4 Drying, suction filtering, collecting filtrate, spin-removing solvent, and purifying by column chromatography to obtain intermediate d-1 structural compound;
detection MALDI-TOF (m/z): calculated value C 23 H 11 Cl 2 N:371.03, test value: 371.00.
3) Under the nitrogen atmosphere, adding a reaction solvent of 1, 2-dichlorobenzene, sequentially adding a reaction intermediate d-1 structural compound (2 mmol), a reaction intermediate f-1 structural compound (4.2 mmol), potassium carbonate (10 mmol), a catalyst CuI (1.0 mmol) and a ligand of 18-crown-6 (1.0 mmol), heating to 100 ℃, and reacting for 24 hours; after the reaction was completed, the mixture was cooled to room temperature, and the organic phase was collected by suction filtration, followed by addition of dichloromethane/H 2 O was extracted, and the collected organic phase was extracted with anhydrous Na 2 SO 4 Drying, suction filtering, collecting filtrate, spin-removing solvent, and purifying by column chromatography to obtain compound with structure of formula 1.
Detection MALDI-TOF (m/z): calculated value C 47 H 31 N 3 :637.25 test value: 637.22.
compound elemental analysis results: calculated values: c,88.51; h,4.90; n,6.59; test value: c,88.51; h,4.90; n,6.59.
According to the similar steps of the method, the structural compounds of formula 5, the structural compounds of formula 33 and the structural compounds of formula 45 are prepared by adopting different raw materials in the step 2) and the step 3), and the specific steps are shown in the following table:
according to steps similar to the above method, the structural compounds of formula 61, formula 62 and formula 63 are prepared from different raw materials in step 1), step 2) and step 3), and the specific examples are shown in the following table:
example 8
An organic light emitting device comprising: the substrate, the ITO anode, the first hole transmission layer, the second hole transmission layer, the electron blocking layer, the luminescent layer, the first electron transmission layer, the second electron transmission layer, the cathode (magnesium silver electrode, magnesium silver mass ratio is 9:1) and the cap layer (CPL) are sequentially arranged, wherein the thickness of the ITO anode is 15nm, the thickness of the first hole transmission layer is 10nm, the thickness of the second hole transmission layer is 95nm, the thickness of the electron blocking layer is 30nm, the thickness of the luminescent layer is 30nm, the thickness of the first electron transmission layer is 30nm, the thickness of the second electron transmission layer is 5nm, the thickness of the magnesium silver electrode is 15nm, and the thickness of the cap layer (CPL) is 100nm.
The OLED device was prepared as follows:
1) Cutting a glass substrate with an ITO anode into a size of 50mm×50mm×0.7mm, respectively performing ultrasonic treatment in isopropanol and deionized water for 30 minutes, and then performing cleaning by exposing to ozone for about 10 minutes; mounting a glass substrate with an ITO anode on a vacuum deposition device;
2) Evaporating a hole buffer layer material HT-1:HAT-CN on an ITO anode in a vacuum evaporation mode, wherein the mass ratio of the compound HT1 to the HAT-CN is 98:2 to obtain a layer with the thickness of 10nm, and the layer is used as a first hole transport layer;
3) Vacuum evaporating a material HT-1 of a second hole transport layer on the first hole transport layer to obtain a layer with the thickness of 95nm, wherein the layer is used as the second hole transport layer;
4) Evaporating a material Prime-1 on the second hole transport layer to obtain a layer with the thickness of 30nm, wherein the layer is used as an electron blocking layer;
5) Co-depositing a light-emitting layer on the electron blocking layer, using the compound of formula 1 prepared in example 1 as a host material, ir (piq) 2 (acac) as doping material, a compound of formula 1 and Ir (piq) 2 (acac) a mass ratio of 19:1, a thickness of 30nm;
6) Vacuum evaporating a material compound ET-1 of the first electron transport layer on the light-emitting layer to obtain a first electron transport layer with the thickness of 30nm;
7) Vacuum evaporating material LiF of the second electron transport layer on the first electron transport layer to obtain a second electron transport layer with the thickness of 5 nm;
8) Vacuum evaporating magnesium and silver on the second electron transport layer to obtain a cathode with the thickness of 15nm, wherein the mass ratio of Mg to Ag is 9:1;
9) The high refractive index hole type material CPL-1 was vacuum deposited on the cathode with a thickness of 100nm, and used as a cathode coating layer (cap layer or CPL).
HAT-CN, HT-1, prime-1, ir (piq) used in the above steps 2 The structures of (acac), ET-1 and CPL-1 are consistent with the technical scheme.
Example 9
An organic light emitting device was prepared according to the method of example 8, except that the compound of formula 1 was replaced with the compound of formula 5.
Example 10
An organic light emitting device was prepared according to the method of example 8, except that the compound of formula 1 was replaced with the compound of formula 33.
Example 11
An organic light emitting device was prepared according to the method of example 8, except that the compound of formula 1 was replaced with the compound of formula 45.
Example 12
An organic light emitting device was prepared according to the method of example 8, except that the compound of formula 1 was replaced with the compound of formula 61.
Example 13
An organic light emitting device was prepared according to the method of example 8, except that the compound of formula 1 was replaced with the compound of formula 62.
Example 14
An organic light emitting device was prepared according to the method of example 8, except that the compound of formula 1 was replaced with the compound of formula 63.
Comparative example 1
An organic light emitting device was prepared according to the method of example 8, except that the structural compound of formula 1 was replaced with a structural compound of formula M1:
performance detection
The OLED devices prepared in examples 8 to 14 and comparative example 1 were tested for current at different voltages using a Keithley 2365A digital nanovoltmeter, and then the current was divided by the light emitting area to obtain the current densities of the OLED devices at 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 ) Is the luminance 1Cd/m 2 A lower turn-on voltage; lifetime LT95 (at 50 mA/cm) obtained by measuring the time when the luminance of the OLED device reaches 95% of the initial luminance 2 Under test conditions; specific detection data are as follows:
OLED device Light-emitting layer host material V on (V) CE(Cd/A) LT95(h)
Example 8 Compounds of formula 1 95.6％ 105.0％ 105.8％
Example 9 Compounds of formula 5 95.3％ 106.2％ 105.2％
Example 10 Compounds of formula 33 94.6％ 104.7％ 105.9％
Example 11 Compounds of formula 45 94.5％ 105.1％ 106.3％
Example 12 Compounds of formula 61 95.2％ 104.9％ 108.1％
Example 13 Compounds of formula 62 96.1％ 105.8％ 107.5％
Example 14 Compounds of formula 63 96.2％ 106.3％ 107.7％
Comparative example 1 Compounds of the formula M1 100％ 100％ 100％
As can be seen from the above-mentioned detection data, the electroluminescent device using the organic compound prepared in the example of the present invention has a lower on-luminance voltage than the device in comparative example 1, and the on-luminance voltage is reduced by about 3.8% to 4.5% (the on-luminance voltage in the above table is the relative on-luminance voltage obtained by taking the on-luminance voltage of comparative example 1 as 100%), so that the power consumption of the device can be effectively reduced; the device using the organic compound prepared in the example of the present invention has higher current efficiency, which is improved by about 4.7% to 6.3% as compared with comparative example 1 (the current efficiency in the above table is obtained by taking the current efficiency of comparative example 1 as 100%); devices using the organic compounds prepared in the examples of the present invention have longer lifetimes, which are extended by about 5.2% to 8.1% compared to those of comparative example 1 (LT 95 in the above table is relative LT95 obtained by taking LT95 of comparative example 1 as 100%).
The organic compound provided by the invention takes the azacyclic structure as a central skeleton, has higher glass transition temperature and thermal stability, is easy to form a good amorphous film, can reduce driving voltage, improves the luminous efficiency and service life of the device, and can be well applied to the technical field of electroluminescence.
While the invention has been described and illustrated with reference to specific embodiments thereof, the description and illustration is not intended to limit the invention. It will be apparent to those skilled in the art that various changes may be made in this particular situation, material, composition of matter, substance, method or process without departing from the true spirit and scope of the invention as defined by the following claims, so as to adapt the objective, spirit and scope of the present application. All such modifications are intended to be within the scope of this appended claims. Although the methods disclosed herein have been described with reference to particular operations being performed in a particular order, it should be understood that these operations may be combined, sub-divided, or reordered to form an equivalent method without departing from the teachings of the present disclosure. Thus, unless specifically indicated herein, the order and grouping of operations is not a limitation of the present application.

Claims (6)

1. An organic compound having the structure of formula I:
in the formula I, n1, n2 and n3 are independently selected from 0 to 2, and n1, n2 and n3 are not 0 at the same time;
x1 and X2 are hydrogen;
the A1, A2 and A3 are independently selected from the structures of formula II:
in the formula II, m is 0 to 3;
l is phenyl;
the Q is selected from one of a formula III, a formula V or a formula VI:
in the formula III, R is hydrogen;
in the formula V, G is hydrogen;
in formula VI, J is phenyl.
2. The organic compound according to claim 1, wherein Q is selected from one of formula a, formula H or formula J:
3. the organic compound according to claim 1, wherein the formula I is selected from one of the following structures:
4. the organic compound according to claim 1, wherein the formula I is selected from one of the following structures:
5. an organic electroluminescent material comprising: an organic compound according to any one of claims 1 to 4.
6. An organic optoelectronic device, comprising: the organic electroluminescent material as claimed in claim 5.
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