CN113582938A - Organic compound and application thereof - Google Patents

Organic compound and application thereof Download PDF

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CN113582938A
CN113582938A CN202110875408.3A CN202110875408A CN113582938A CN 113582938 A CN113582938 A CN 113582938A CN 202110875408 A CN202110875408 A CN 202110875408A CN 113582938 A CN113582938 A CN 113582938A
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organic compound
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代文朋
高威
张磊
翟露
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Wuhan Tianma Microelectronics Co Ltd
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Shanghai Tianma AM OLED Co Ltd
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Abstract

The invention provides an organic compound and application thereof, wherein the organic compound has a structure shown in a formula I, and the organic compound provided by the invention enables a mother nucleus structure in a molecular structure to be a structure formed by at least one benzene ring formed by the refolding of benzoxazole through the design of the molecular structure, and simultaneously contains arylamine groups of at least two amino groups, so that the organic compound has a smaller extinction coefficient in a blue light region, almost does not absorb blue light, and is beneficial to improving the luminous efficiency.

Description

Organic compound and application thereof
Technical Field
The invention belongs to the field of organic electroluminescent materials, and relates to an organic compound and application thereof.
Background
OLED devices have made significant progress over decades of development. Although the internal quantum efficiency is close to 100%, the external quantum efficiency is only about 20%, and most of light is confined inside the light emitting device due to substrate mode loss, surface plasmon loss, waveguide effect and the like, resulting in a large amount of energy loss.
In the top emission device, an organic Coating (CPL) is evaporated on a semitransparent metal electrode Al, so that the optical interference distance is adjusted, the external light reflection is inhibited, and the extinction caused by the movement of surface plasma is inhibited, thereby improving the light extraction efficiency and the luminous efficiency.
The performance requirement on CPL materials in the current OLED device is very high, and the CPL materials are required to have no absorption in a visible light wavelength region (400 nm-700 nm); high refractive index (generally, n is more than 2.1eV), and low extinction coefficient (k is less than or equal to 0.1) in the wavelength range of 400nm to 600 nm; high glass transition temperature and molecular thermal stability (high glass transition temperature, vapor deposition capability and no thermal decomposition). The prior CPL material technology mostly adopts aromatic amine derivatives, phosphorus oxy derivatives, quinolinone derivatives and the like, has the functions of hole transmission and electron transmission, and improves the light extraction efficiency to a certain extent.
However, most of the current CPL materials have a refractive index of less than 1.9, and cannot meet the requirement of high refractive index; under the condition that the refractive index meets the requirement, the visible light region has stronger absorption or larger extinction coefficient; amine derivatives having a specific structure with a high refractive index and using a material satisfying specific parameters improve light extraction efficiency, but do not solve the problems of both luminous efficiency and chromaticity, particularly in a blue light emitting element. In order to increase the molecular density and achieve high thermal stability, the existing material has a large and loose molecular structure design, and tight accumulation among molecules cannot be achieved, so that too many molecular gel holes are formed during evaporation and the covering tightness is poor; the single design of the electronic type covering layer material can achieve the effects of electronic transmission and light extraction, save the preparation cost of the device to a certain extent to achieve multiple effects, but is not beneficial to the extraction of light, only weakly improves the luminous efficiency, and does not solve the problem of chromaticity.
Therefore, in the field, it is desired to develop a CPL material having a higher refractive index and a smaller extinction coefficient, which can effectively improve the external quantum efficiency of the device.
Disclosure of Invention
In view of the shortcomings of the prior art, the present invention aims to provide an organic compound and its application.
In order to achieve the purpose, the invention adopts the following technical scheme:
one of the objects of the present invention is to provide an organic compound having a structure represented by formula I or formula II:
Figure BDA0003190351270000021
wherein M is selected from Ar or
Figure BDA0003190351270000022
Ar is selected from one of substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30, and Ar1、Ar2、Ar3、Ar4And Ar5One or both of them are
Figure BDA0003190351270000023
The group, X is O, S or N, L is selected from one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30; r is an aromatic ring condensed with the benzene ring, and the bond of the R group crossing the benzene ring represents that the R group passes through the benzene ringThe bond which can be condensed in (a) is linked to a benzene ring, the asterisk indicates the linking position of the group, and n is an integer of 1 to 3 (e.g., 1, 2, 3);
removing device
Figure BDA0003190351270000024
Outer, Ar1、Ar2、Ar3、Ar4And Ar5The rest groups are independently selected from one of substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30.
In the present invention, each of C6 to C30 may be C6, C8, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, or C28, independently.
Each of C3 to C30 may be independently C4, C6, C8, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, or the like.
The organic compound provided by the invention has the advantages that through the design of a molecular structure, a mother nucleus structure in the molecular structure is a structure formed by at least one benzene ring condensed by benzoxazole, and the organic compound also contains an arylamine group containing at least two amino groups, so that the organic compound has a smaller extinction coefficient in a blue light region (400-450nm), almost does not absorb blue light, and is favorable for improving the luminous efficiency.
It is a second object of the present invention to provide an electroluminescent material comprising an organic compound as described in the first object of the invention.
It is a second object of the present invention to provide an electron transport material comprising the organic compound according to the first object of the present invention.
It is a further object of the present invention to provide a hole transport layer material comprising the organic compound according to one of the objects.
It is a fourth object of the present invention to provide a capping layer material comprising an organic compound according to one of the objects.
The fifth purpose of the invention is to provide an OLED device, which comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, wherein the material of the organic thin film layer comprises the organic compound of one of the purposes.
The sixth purpose of the present invention is to provide a display panel, which comprises the OLED device of the fourth purpose.
Compared with the prior art, the invention has the following beneficial effects:
the compound provided by the invention takes at least one benzene ring fused by benzoxazole as a mother nucleus structure, and the mother nucleus structure is connected with an arylamine group containing at least two amino groups, so that the compound has a smaller extinction coefficient in a blue light region (400-450nm), almost does not absorb blue light, and is beneficial to improving the luminous efficiency.
Drawings
Fig. 1 is a schematic structural diagram of an OLED device of the present invention, where 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a first hole transport layer, 5 is a second hole transport layer, 6 is a light emitting layer, 7 is a first electron transport layer, 8 is a second electron transport layer, 9 is a cathode, 10 is a cap layer, and an arrow represents a light emitting direction of the device.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
One of the objects of the present invention is to provide an organic compound having a structure represented by formula I or formula II:
Figure BDA0003190351270000031
wherein M is selected from Ar or
Figure BDA0003190351270000032
Ar is selected from one of substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30, and Ar1、Ar2、Ar3、Ar4And Ar5One or both of them are
Figure BDA0003190351270000033
The group, X is O, S or N, L is selected from one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30; r is an aromatic ring condensed with the benzene ring, the bond of the R group crossing the benzene ring represents that the R group is connected with the benzene ring through a condensable bond on the benzene ring, an asterisk represents the connecting position of the group, and n is an integer of 1-3 (such as 1, 2 and 3);
removing device
Figure BDA0003190351270000041
Outer, Ar1、Ar2、Ar3、Ar4And Ar5The rest groups are independently selected from one of substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30.
In the present invention, each of C6 to C30 may be C6, C8, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, or C28, independently.
Each of C3 to C30 may be independently C4, C6, C8, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, or the like.
In the present invention, the term "aryl" includes monocyclic or polycyclic (e.g., 2, 3, 4, or 5, etc. fused rings) aryl groups, illustratively including, but not limited to: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, anthracenyl, indenyl, phenanthryl, pyrenyl, acenaphthenyl, triphenylenyl, phenanthrenyl, fluorenyl, phenanthrenyl, acenaphthenyl, phenanthrenyl, and phenanthrenyl,
Figure BDA0003190351270000042
An acenaphthenyl group, a perylenyl group, or the like. The following relates to the same description and all has the same meaning.
The heteroatom in the term "heteroaryl" includes O, S, N, P, B or Si, etc.; heteroaryl includes monocyclic or polycyclic (e.g., 2, 3, 4, or 5 fused rings) heteroaryl, illustratively including but not limited to: pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzopyrazinyl, pyridopyridyl, pyridopyrazinyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, benzimidazolyl, or phenanthrolinyl, and the like. The following relates to the same description and all has the same meaning.
The organic compound provided by the invention has the advantages that through the design of a molecular structure, a mother nucleus structure in the molecular structure is a structure formed by at least one benzene ring condensed by benzoxazole, and the organic compound also contains an arylamine group containing at least two amino groups, so that the organic compound has a smaller extinction coefficient in a blue light region (400-450nm), almost does not absorb blue light, and is favorable for improving the luminous efficiency.
In one embodiment, Ar1、Ar2、Ar3、Ar4And Ar5Wherein the remaining groups are independently selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted tetrabiphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted indolocarbafuranyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted benzofuranyl pyrimidinyl group, A substituted or unsubstituted benzothiophene pyrimidinyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted pyrenyl group.
In one embodiment, when the group is substituted as described above, the substituent is selected from deuterium, cyano, methyl, methoxy, tert-butyl or fluoro.
In one embodiment, the water-soluble polymer is a polymer of the formula
Figure BDA0003190351270000051
Outer, Ar1、Ar2、Ar3、Ar4And Ar5Wherein the remaining groups are independently selected from phenyl, biphenyl, terphenyl, quaterphenyl or naphthyl.
In one embodiment, Ar is selected from phenylene, biphenylene, or naphthylene.
In one embodiment, Ar is selected from
Figure BDA0003190351270000052
Figure BDA0003190351270000053
In one embodiment, R is selected from
Figure BDA0003190351270000054
Wherein any of the annealable bonds forms an annealable structure with any of the annealable bonds on the phenyl ring on which R is located.
In one embodiment of the method of the present invention,
Figure BDA0003190351270000055
any one selected from the following groups:
Figure BDA0003190351270000056
in one embodiment, L is selected from phenyl, biphenyl, naphthyl, pyridinyl or pyrimidinyl.
In one embodiment, L is selected from
Figure BDA0003190351270000057
Figure BDA0003190351270000058
In one embodiment, the organic compound is a compound having any one of the following structures:
Figure BDA0003190351270000061
wherein Ar is1、Ar2、Ar3、Ar4、Ar5X, R, L and n are as defined in formula I.
In one embodiment, the organic compound is any one of the following compounds 1 to 27:
Figure BDA0003190351270000062
Figure BDA0003190351270000071
Figure BDA0003190351270000081
Figure BDA0003190351270000091
Figure BDA0003190351270000101
Figure BDA0003190351270000111
Figure BDA0003190351270000121
Figure BDA0003190351270000131
Figure BDA0003190351270000141
the organic compound with the structure shown in the formula I is prepared by the following synthetic route:
Figure BDA0003190351270000142
wherein Ligand is
Figure BDA0003190351270000143
[Pd(cinnamyl)Cl]2Palladium chloride (1-phenylallyl), KO (t-Bu) potassium tert-butoxide, Toluene Toluene.
It is a second object of the present invention to provide an electroluminescent material comprising an organic compound as described in the first object of the invention.
It is a second object of the present invention to provide an electron transport material comprising the organic compound according to the first object of the present invention.
It is a further object of the present invention to provide a hole transport layer material comprising the organic compound according to one of the objects.
The fourth object of the present invention is to provide a coating material comprising the organic compound according to one of the objects.
The fifth purpose of the invention is to provide an OLED device, which comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, wherein the material of the organic thin film layer comprises the organic compound of one of the purposes.
In one embodiment, the organic thin film layer includes an electron transport layer, a light emitting layer, a hole transport layer, a capping layer, and a material of at least one of the organic thin film layers includes an organic compound according to one of the objects.
In one embodiment, the capping layer comprises an organic compound according to one of the objects.
In the OLED device provided by the invention, the anode material can be metal, metal alloy, metal oxide or conductive polymer; wherein the metal includes copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc., the metal alloy includes an alloy of at least two of copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, the metal oxide includes indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), etc., and the conductive polymer includes polyaniline, polypyrrole, poly (3-methylthiophene), etc. In addition to the materials described above and combinations thereof that facilitate hole injection, materials known to be suitable for use as anodes are also included.
In the OLED device, the cathode material can be metal, metal alloy or multilayer metal material; wherein the metal comprises aluminum, magnesium, silver, indium, tin, titanium and the like, the alloy is formed by at least two of aluminum, magnesium, silver, indium, tin and titanium, and the multilayer metal material comprises LiF/Al and LiO2/Al、BaF2Al, etc. In addition to the above-mentioned materials and combinations thereof which facilitate electron injection, known materials suitable for use as cathodes are also included.
In the OLED device, the organic thin film layer includes at least one light emitting layer (EML), and may further include other functional layers, for example, 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 Injection Layer (EIL), and an Electron Injection Layer (EIL).
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 evaporation, sputtering, spin coating, dipping, ion plating, and the like can be used to form the organic thin layer.
The sixth purpose of the present invention is to provide a display panel, which comprises the OLED device of the fourth purpose.
The following examples exemplarily provide a series of methods for synthesizing specific compounds, and compounds that are not mentioned in the specific methods can be synthesized by similar methods, or can be synthesized by other existing methods, which is not specifically limited in the present invention.
Example 1
Synthesis of organic compound 1, its structure is as follows:
Figure BDA0003190351270000161
the preparation method specifically comprises the following steps:
Figure BDA0003190351270000162
1) 1-1(0.5mmol), 1-2(1.5mmol), KO (t-Bu) (1.2mmol) and [ Pd (cinnamyl) Cl]2(0.05mol) and Ligand (0.1mol) were added to a toluene solution (3 mL) and mixed, and the mixture was placed in a 50mL flask and reacted at 90 ℃ for 12 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution4The aqueous solution and ethyl acetate are extracted for three times, then the organic layer is subjected to column chromatography by a rotary evaporator to remove the solvent, and the target product 1 is obtained.
The structure of target product 1 was tested: MALDI-TOFMS (m/z) is obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry: c52H34N4O2Calculated 746.3 and test 746.1.
Elemental analysis: theoretical value C, 83.63; h, 4.59; n, 7.50; test value C, 83.63; h, 4.58; n, 7.51.
Example 2
Synthesis of organic Compound 4, the structure of which is as follows:
Figure BDA0003190351270000163
the preparation method specifically comprises the following steps:
Figure BDA0003190351270000171
1) 4-1(0.5mmol), 4-2(1.0mmol), KO (t-Bu) (1.2mmol) and [ Pd (cinnamyl) Cl]2(0.05mol) and Ligand (0.1mol) were added to a toluene solution (3 mL) and mixed, and the mixture was placed in a 50mL flask and reacted at 90 ℃ for 12 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution4The aqueous solution and ethyl acetate are extracted for three times, then the organic layer is subjected to column chromatography by a rotary evaporator to remove the solvent, and a target product 4 is obtained.
The structure of target product 4 was tested: MALDI-TOFMS (m/z) is obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry: c57H40N4O, calculated 796.3, test value 796.1.
Elemental analysis: theoretical value C, 85.90; h, 5.06; n, 7.03; test value C, 85.91; h, 5.05; and N, 7.03.
Example 3
Synthesis of organic compound 8, its structure is as follows:
Figure BDA0003190351270000172
the preparation method specifically comprises the following steps:
Figure BDA0003190351270000173
1) adding 8-1(0.5mmol), 1-2(1.5mmol), KO (t-Bu) (1.5mmol) and [ Pd (cinnamyl) Cl]2(0.05mol) and Ligand (0.1mol) were added to a toluene solution (3 mL) and mixed, and the mixture was placed in a 50mL flask and reacted at 90 ℃ for 12 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution4The aqueous solution and ethyl acetate are extracted for three times, then the organic layer is subjected to column chromatography by a rotary evaporator to remove the solvent, and the target product 8 is obtained.
Test the structure of target product 8: ionization time-of-flight mass spectrometry by matrix-assisted laser desorptionObtaining MALDI-TOFMS (m/z): c56H36N4O2Calculated value is 796.3 and test value is 796.2.
Elemental analysis: theoretical value C, 84.40; h, 4.55; n, 7.03; test value C, 84.41; h, 4.55; and N, 7.02.
Example 4
Synthesis of organic compound 22, its structure is as follows:
Figure BDA0003190351270000181
the preparation method specifically comprises the following steps:
Figure BDA0003190351270000182
1) 4-1(0.5mmol), 22-1(1.0mmol), KO (t-Bu) (1.2mmol) and [ Pd (cinnamyl) Cl]2(0.05mol) and Ligand (0.1mol) were added to a toluene solution (3 mL) and mixed, and the mixture was placed in a 50mL flask and reacted at 90 ℃ for 12 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution4The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to column chromatography by removing the solvent through a rotary evaporator to obtain the objective product 22.
The structure of target product 22 was tested: MALDI-TOFMS (m/z) is obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry: c57H40N4O, calculated 796.3, test value 796.1.
Elemental analysis: theoretical value C, 85.90; h, 5.06; n, 7.03; test value C, 85.90; h, 5.06; and N, 7.04.
Example 5
Synthesis of organic Compound 39, the structure of which is as follows:
Figure BDA0003190351270000183
the preparation method specifically comprises the following steps:
Figure BDA0003190351270000191
1) 39(0.5mmol), 1-2(1.5mmol), KO (t-Bu) (1.2mmol) and [ Pd (cinnamyl) Cl]2(0.05mol) and Ligand (0.1mol) were added to a toluene solution (3 mL) and mixed, and the mixture was placed in a 50mL flask and reacted at 90 ℃ for 10 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution4The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to column chromatography by removing the solvent through a rotary evaporator to obtain the objective product 39.
The structure of target product 39 was tested: MALDI-TOFMS (m/z) is obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry: c62H36N6O2Calculated value is 896.3 and test value is 896.0.
Elemental analysis: theoretical value C, 83.02; h, 4.05; n, 9.37; test value C, 83.02; h, 4.06; n, 9.37.
Example 6
Synthesis of organic compound 75, its structure is as follows:
Figure BDA0003190351270000192
the preparation method specifically comprises the following steps:
Figure BDA0003190351270000193
1) 75(0.5mmol), 1-2(1.5mmol), KO (t-Bu) (1.2mmol) and [ Pd (cinnamyl) Cl]2(0.05mol) and Ligand (0.1mol) were added to a toluene solution (3 mL) and mixed, and the mixture was placed in a 50mL flask and reacted at 90 ℃ for 12 hours. Cooled to room temperature, and then saturated MgSO was slowly added to the solution4The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to column chromatography by removing the solvent through a rotary evaporator to obtain the target product 75.
Testing of target products75 structure: MALDI-TOFMS (m/z) is obtained by matrix-assisted laser desorption ionization time-of-flight mass spectrometry: c56H36N6O2Calculated 824.3 and test 824.2.
Elemental analysis: theoretical value C, 81.53; h, 4.40; n, 10.19; test value C, 81.53; h, 4.41; n, 10.17.
The preparation methods of the compounds of the present invention used in the specific embodiments are all similar to the above methods, and are not repeated herein, but only the characterization results are provided, and the mass spectrometry and elemental analysis results are shown in table 1.
TABLE 1
Figure BDA0003190351270000201
Performance test-characterization of refractive index of Material
The refractive indices of the compounds at wavelengths of 460nm, 530nm and 620nm and the absorption coefficient (K value) at the wavelength of 460nm were tested by an ellipsometer.
The test results are shown in table 2.
TABLE 2
Figure BDA0003190351270000202
Figure BDA0003190351270000211
Wherein the structures of comparative compounds C1 and C2 are as follows:
Figure BDA0003190351270000212
as can be seen from the structure of Table 2, the fused aryl group on the benzoxazole benzene can increase the refractive index of the molecule.
Device application example
The application example provides an organic electroluminescent device, the structure of which is shown in fig. 1, and the specific preparation steps are as follows:
1) cutting a glass substrate 1 with an Indium Tin Oxide (ITO) anode layer 2 (thickness 15nm) into sizes of 50mm x 0.7mm, sonicating in isopropanol and deionized water for 30 minutes, respectively, and then exposing to ozone for about 10 minutes for cleaning, mounting the cleaned substrate 1 on a vacuum deposition apparatus;
2) evaporating a hole injection layer material compound b and a p-doped material compound a on the ITO anode layer 2 in a vacuum evaporation mode, wherein the doping proportion is 3 percent (mass ratio); a thickness of 5nm as a hole injection layer 3;
3) vacuum evaporating a hole transport layer material compound b on the hole injection layer 3, wherein the thickness of the hole transport layer material compound b is 100nm and is used as a first hole transport layer 4;
4) vacuum evaporating a hole transport type material compound c on the first hole transport layer 4, wherein the thickness of the hole transport type material compound c is 5nm and the hole transport type material compound c serves as a second hole transport layer 5;
5) a luminescent layer 6 is vacuum-evaporated on the second hole transport layer 5, wherein the compound d is used as a main material, the compound e is used as a doping material, the doping proportion is 3% (mass ratio), and the thickness is 30 nm;
6) an electron transport type material compound f is vacuum-evaporated on the light emitting layer 6 to a thickness of 30nm to form a first electron transport layer 7;
7) an electron transport material compound g and an n-doped material compound h are vacuum-evaporated on the first electron transport layer 7, and the doping mass ratio is 1: 1; a thickness of 5nm as a second electron transport layer 8;
8) a magnesium silver electrode is evaporated on the second electron transport layer 8 in vacuum, wherein the ratio of Mg to Ag is 9:1, the thickness is 10nm, and the magnesium silver electrode is used as a cathode 9;
9) compound 1 of the present invention is vacuum-deposited on cathode 9 to a thickness of 100nm, and used as cap layer 10.
The compound used in the above step has the following structure:
Figure BDA0003190351270000221
application example 2
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 4; the other preparation steps are the same.
Application example 3
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 7; the other preparation steps are the same.
Application example 4
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 8; the other preparation steps are the same.
Application example 5
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 19; the other preparation steps are the same.
Application example 6
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 22; the other preparation steps are the same.
Application example 7
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 28; the other preparation steps are the same.
Application example 8
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 33; the other preparation steps are the same.
Application example 9
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 37; the other preparation steps are the same.
Application example 10
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 39; the other preparation steps are the same.
Application example 11
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 41; the other preparation steps are the same.
Application example 12
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 66; the other preparation steps are the same.
Application example 13
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 75; the other preparation steps are the same.
Application example 14
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of organic compound 87; the other preparation steps are the same.
Comparative example 1
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of comparative compound 1 (C1); the other preparation steps are the same.
Comparative example 2
An OLED device which differs from application example 1 only in that organic compound 1 is replaced with an equal amount of comparative compound 1 (C2); the other preparation steps are the same.
Performance evaluation of OLED devices:
testing the current of the OLED device under different voltages by using a Keithley 2365A digital nano-volt meter, and then dividing the current by the light-emitting area to obtain the current density of the OLED device under different voltages; testing the brightness and radiant energy flux density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; according to the current density and the brightness of the OLED device under different voltages, the current density (10 mA/cm) is obtained under the same current density2) Working voltage V, current efficiency (cd/a) and external quantum efficiency EQE (%); vONFor a luminance of 1cd/m2A lower turn-on voltage; the lifetime T95 (at 50 mA/cm) was obtained by measuring the time for the luminance of the OLED device to reach 95% of the initial luminance2Under test conditions); performance data as shown in the table3, respectively.
TABLE 3
Figure BDA0003190351270000241
Figure BDA0003190351270000251
From the data in table 3, the organic compound provided by the present invention as a capping layer material can make the OLED device have a lower operating voltage (below 3.44V), a higher current efficiency (above 8.08 cd/a), a higher external quantum efficiency (above 17.1%) and a longer lifetime (above 69 h).
The applicant states that the present invention is illustrated by the above examples of the organic compounds of the present invention and their applications, but the present invention is not limited to the above examples, i.e. it is not meant that the present invention must rely on the above examples to be practiced. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (20)

1. An organic compound having a structure according to formula I:
Figure FDA0003190351260000011
wherein M is selected from Ar or
Figure FDA0003190351260000012
Ar is selected from one of substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30, and Ar1、Ar2、Ar3、Ar4And Ar5One or both of them are
Figure FDA0003190351260000013
The group, X is O, S or N, L is selected from one of single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30; r is an aromatic ring condensed with the benzene ring, the bond of the R group crossing the benzene ring represents that the R group is connected with the benzene ring through a condensable bond on the benzene ring, an asterisk represents the connecting position of the group, and n is an integer of 1-3;
removing device
Figure FDA0003190351260000014
Outer, Ar1、Ar2、Ar3、Ar4And Ar5The rest groups are independently selected from one of substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30.
2. An organic compound according to claim 1, characterized in that
Figure FDA0003190351260000015
Outer, Ar1、Ar2、Ar3、Ar4And Ar5Wherein the remaining groups are independently selected from the group consisting of substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted quaterphenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted triphenylene groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted carbazolyl groups, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted indolocarbathiophenyl group, a substituted or unsubstituted benzofuranyl pyrimidinyl group.A substituted or unsubstituted benzothiophene pyrimidinyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted pyrenyl group.
3. An organic compound according to claim 1 or 2, wherein when the group is substituted, the substituent is selected from deuterium, cyano, methyl, methoxy, tert-butyl or fluoro.
4. An organic compound according to claim 2, characterized in that
Figure FDA0003190351260000021
Outer, Ar1、Ar2、Ar3、Ar4And Ar5Wherein the remaining groups are independently selected from phenyl, biphenyl, terphenyl, quaterphenyl or naphthyl.
5. An organic compound according to claim 1, wherein Ar is selected from phenylene, biphenylene or naphthylene.
6. The organic compound of claim 5, wherein Ar is selected from the group consisting of
Figure FDA0003190351260000022
Figure FDA0003190351260000023
7. An organic compound according to claim 1, wherein R is selected from
Figure FDA0003190351260000024
Wherein any of the annealable bonds forms an annealable structure with any of the annealable bonds on the phenyl ring on which R is located.
8. According to claim1, characterized in that,
Figure FDA0003190351260000025
any one selected from the following groups:
Figure FDA0003190351260000031
9. the organic compound of claim 1 or 8, wherein L is selected from the group consisting of phenylene, biphenylene, naphthylene, pyridinylene, and pyrimidinylene.
10. The organic compound of claim 9, wherein L is selected from the group consisting of
Figure FDA0003190351260000032
Figure FDA0003190351260000033
11. The organic compound according to claim 1, wherein the organic compound is a compound having any one of the following structures:
Figure FDA0003190351260000034
，
wherein Ar, Ar1、Ar2、Ar3、Ar4、Ar5X, R, L and n are as defined in formula I.
12. The organic compound according to claim 1, wherein the organic compound is any one of the following compounds 1 to 27:
Figure FDA0003190351260000041
Figure FDA0003190351260000051
Figure FDA0003190351260000061
Figure FDA0003190351260000071
Figure FDA0003190351260000081
Figure FDA0003190351260000091
Figure FDA0003190351260000101
Figure FDA0003190351260000111
Figure FDA0003190351260000121
13. an electroluminescent material comprising the organic compound according to any one of claims 1 to 12.
14. An electron transport material comprising the organic compound according to any one of claims 1 to 12.
15. A hole transport layer material, characterized in that it comprises an organic compound according to any one of claims 1 to 12.
16. A cover material, characterized in that it comprises an organic compound according to any one of claims 1 to 12.
17. An OLED device comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode, wherein the material of the organic thin film layer comprises the organic compound according to any one of claims 1 to 12.
18. The OLED device according to claim 17, wherein the organic thin film layer comprises an electron transport layer, a light emitting layer, a hole transport layer, and a cover layer, and a material of at least one of the organic thin film layers comprises the organic compound according to any one of claims 1 to 12.
19. The OLED device of claim 18, wherein the capping layer comprises the organic compound of any one of claims 1-12.
20. A display panel comprising an OLED device as claimed in any one of claims 17 to 19.
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