CN109503576B - Organic compound, display panel, and display device - Google Patents

Organic compound, display panel, and display device Download PDF

Info

Publication number
CN109503576B
CN109503576B CN201811580723.8A CN201811580723A CN109503576B CN 109503576 B CN109503576 B CN 109503576B CN 201811580723 A CN201811580723 A CN 201811580723A CN 109503576 B CN109503576 B CN 109503576B
Authority
CN
China
Prior art keywords
substituted
unsubstituted
group
layer
organic 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
CN201811580723.8A
Other languages
Chinese (zh)
Other versions
CN109503576A (en
Inventor
张磊
高威
牛晶华
安平
卞华锋
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 CN201811580723.8A priority Critical patent/CN109503576B/en
Publication of CN109503576A publication Critical patent/CN109503576A/en
Application granted granted Critical
Publication of CN109503576B publication Critical patent/CN109503576B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—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
    • 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
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • 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
    • H10K85/649—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

Abstract

The present invention relates to an organic compound, and a display panel and a display device including the organic compound. The organic compound has a structure shown in chemical formula 1; l is1To L4Each independently selected from substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C5 to C30 heteroarylene, substituted or unsubstituted C1 to C8 alkylene, or substituted or unsubstituted C1 to C8 alkyleneoxy; a. b, c and d independently represent numbers 0 and 1, and a + b + c + d is more than or equal to 1; ar (Ar)1、Ar2、Ar3And Ar4Each independently has a structure represented by chemical formula 3; wherein R is21To R27Each independently selected from a hydrogen atom, a substituted or unsubstituted C6 to C18 aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted C1 to C16 alkyl group, a substituted or unsubstituted C1 to C16 alkoxy group, a hydroxyl group, or a carboxyl group.
Figure DDA0001917752750000011

Description

Organic compound, display panel, and display device
Technical Field
The present disclosure relates to the field of organic electroluminescent materials, and more particularly, to a novel organic compound, and a display panel and a display device including the same.
Background
With the commercialization and practicability of electroluminescent devices, electronic transmission materials with higher transmission efficiency and better usability are desired, and researchers have made some exploratory work in this field. The electron transport material used in conventional electroluminescent devices is Alq3 (aluminum 8-hydroxyquinoline), however the electron mobility ratio of Alq3 is lower(approximately at l0-6cm2Vs) such that electron transport and hole transport of the device are not balanced.
Currently, commonly used electron transport materials (e.g., bathophenanthroline (BPhen), Bathocuproine (BCP) and TmPyPB (1,3, 5-tris [ (3-pyridyl) -3-phenyl ] benzene)) can substantially meet the market demand of organic electroluminescent panels, but their glass transition temperature is low (generally less than 85 ℃), and when the device is operated, the generated joule heat causes degradation of molecules and change of molecular structure, resulting in low panel efficiency and poor thermal stability. Meanwhile, the molecular structure is symmetrical and regular, and the crystal is easy to crystallize after a long time. Once the electron transport material is crystallized, the intermolecular charge jump mechanism is different from the normal amorphous thin film mechanism, resulting in the decrease of electron transport performance, the imbalance of electron and hole mobility of the whole device, the exciton formation efficiency is greatly reduced, and excitons are intensively formed at the interface of the electron transport layer and the light emitting layer, resulting in the substantial decrease of device efficiency and lifetime.
Disclosure of Invention
The invention aims to provide a novel organic compound, a display panel and a display device comprising the organic compound, wherein the organic compound can be used as a stable and efficient electron transport material and/or an electron injection material, can simultaneously have high electron mobility and high glass transition temperature, can be effectively doped, is stable and efficient, reduces threshold voltage, improves device efficiency, prolongs device service life, and has important practical application value.
According to a first aspect of the present invention, there is provided an organic compound having a structure represented by chemical formula 1 or chemical formula 2:
Figure BDA0001917752730000021
wherein L is1To L4Each independently selected from substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C5 to C30 heteroarylene, and substituted or unsubstituted C1 to C30 heteroaryleneC8 alkylene or substituted or unsubstituted C1 to C8 alkyleneoxy;
a. b, c, d, e and f represent numbers 0 and 1 respectively and independently, a + b + c + d is more than or equal to 1, and e + f is more than or equal to 1;
Ar1、Ar2、Ar3and Ar4Each independently has a structure represented by chemical formula 3:
Figure BDA0001917752730000022
wherein R is21To R27Each independently selected from a hydrogen atom, a substituted or unsubstituted C6 to C18 aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted C1 to C16 alkyl group, a substituted or unsubstituted C1 to C16 alkoxy group, a hydroxyl group, or a carboxyl group;
# denotes the attachment position in chemical formula 1 or chemical formula 2.
According to a second aspect of the present invention, there is provided a display panel comprising an organic light emitting device comprising a substrate, an anode and a cathode disposed opposite to each other, a cap layer on a side of the cathode facing away from the anode, and an organic functional layer between the anode and the cathode, the organic functional layer comprising an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer and a cap layer, at least one of the electron injection layer, the electron transport layer and the light emitting layer containing an organic compound as described above.
According to a third aspect of the present invention, there is provided a display device comprising the display panel according to the second aspect of the present invention.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings needed to be used in the embodiments or the prior art descriptions will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without inventive exercise.
FIG. 1 is a chemical formula of an organic compound provided according to one embodiment of the present invention;
FIG. 2 is a chemical formula of an organic compound provided according to an embodiment of the present invention;
fig. 3 is a schematic structural diagram of an organic light emitting device according to an embodiment of the present invention;
fig. 4 is a schematic diagram of a display device according to an embodiment of the present invention.
Detailed Description
The present invention is further illustrated by the following examples and comparative examples, which are intended to be illustrative only and are not to be construed as limiting the invention. All modifications and substitutions of the technical solution of the present invention without departing from the scope of the technical solution of the present invention shall be covered in the protection scope of the present invention.
The invention provides an organic compound, a display panel and a display device.
According to an aspect of the present invention, there is provided an organic compound having a structure represented by chemical formula 1 or chemical formula 2 shown in fig. 1 or 2, respectively:
Figure BDA0001917752730000041
wherein L is1To L4Each independently selected from substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C5 to C30 heteroarylene, substituted or unsubstituted C1 to C8 alkylene, or substituted or unsubstituted C1 to C8 alkyleneoxy;
a. b, c, d, e and f represent numbers 0 and 1 respectively and independently, a + b + c + d is more than or equal to 1, and e + f is more than or equal to 1;
Ar1、Ar2、Ar3and Ar4Each independently has a structure represented by chemical formula 3:
Figure BDA0001917752730000042
wherein R is21To R27Each independently selected from a hydrogen atom, a substituted or unsubstituted C6 to C18 aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted C1 to C16 alkyl group, a substituted or unsubstituted C1 to C16 alkoxy group, a hydroxyl group, or a carboxyl group;
# denotes the attachment position in chemical formula 1 or chemical formula 2.
According to the organic compound of the chemical formula 1, a spirofluorene group and a phenanthroline group are adopted, wherein the spirofluorene group is an important blue fluorescence parent nucleus, molecules of the spirofluorene group are in a twisted non-coplanar structure, and the conjugation degree in the molecules is reduced, so that the light-emitting wavelength is blue-shifted, and the color purity of a device is effectively improved; meanwhile, the twisted structure of the fluorescent material can avoid intramolecular aggregation and improve the luminous efficiency; the rigid structure of the spirofluorene greatly improves the thermal stability of the molecule; wherein the phenanthroline group is an excellent electron-deficient group, and is widely used as a group of an electron transport layer, and the organic compound has the advantages of the two groups, and can be used as a blue luminescent material, an electron transport material and an electron transport and luminescent material.
Moreover, the organic compound of the formula 2 according to the present invention employs a diphenyl fluorene group and a phenanthroline group, wherein the diphenyl fluorene group is similar to spirofluorene in structure and is also an important blue fluorescence parent nucleus, and the molecule thereof is in a twisted non-coplanar structure, so that the degree of conjugation in the molecule is reduced, the emission wavelength is blue-shifted, and the color purity of the device is effectively improved; meanwhile, the twisted structure of the fluorescent material can avoid intramolecular aggregation and improve the luminous efficiency; the rigid structure of the dibenzofluorene greatly improves the thermal stability of molecules; wherein the phenanthroline group is an excellent electron-deficient group, and is widely used as a group of an electron transport layer, and the organic compound has the advantages of the two groups, and can be used as a blue luminescent material, an electron transport material and an electron transport and luminescent material.
According to an embodiment of the present invention, in the chemical formula 1 or 2, L1And L2Independently represents one of the following structures:
Figure BDA0001917752730000061
Z1and Z2Each independently selected from a hydrogen atom, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 fused aryl group, a substituted or unsubstituted C6 to C30 fused heteroaryl group, a substituted or unsubstituted C1 to C16 alkylene group, a substituted or unsubstituted C1 to C16 alkyleneoxy group; and is
In chemical formulas 2-1 to 2-3, p represents any integer of numbers 0 to 4; in chemical formulas 2-4 to 2-8, p represents any integer of numbers 0 to 6; in chemical formulas 2-9 to 2-10, p represents any integer of numbers 0 to 5, and q represents any integer of numbers 0 to 3; in chemical formulas 2-11, 2-12, 2-18, 2-19 and 2-20, p represents any integer of numbers 0 to 2; in chemical formulas 2-15 to 2-17, p represents any integer of numbers 0 to 3;
wherein, # denotes the attachment position in chemical formula 1 or chemical formula 2.
According to an embodiment of the present invention, in the chemical formula 1 or 2, L1And L2Independently represents one of the following structures:
Figure BDA0001917752730000071
wherein, # denotes the attachment position in chemical formula 1 or chemical formula 2.
According to an embodiment of the present invention, in chemical formula 1, a-1, b-c-d-0.
According to an embodiment of the present invention, in chemical formula 1, a is 1, b is 1, and c is 0.
According to an embodiment of the present invention, in chemical formula 1, a is 1, c is 1, and b is 0.
According to an embodiment of the present invention, in chemical formula 1, a ═ b ═ c ═ d ═ 1.
According to an embodiment of the present invention, in chemical formula 1, a ═ b ═ c ═ 1, and d ═ 0.
According to an embodiment of the present invention, in chemical formula 2, e ═ 1, f ═ 0; or e is 0 and f is 1.
According to an embodiment of the present invention, in chemical formula 2, e ═ f ═ 1.
According to one embodiment of the present invention, Ar5-Ar9Each independently selected from phenyl, biphenyl, terphenyl, pyridyl, pyrimidyl, naphthyl, anthryl, phenanthryl and benzophenanthryl.
According to one embodiment of the invention, the organic compound is selected from one of the following compounds:
Figure BDA0001917752730000091
Figure BDA0001917752730000101
Figure BDA0001917752730000111
according to one embodiment of the present invention, the organic compound of chemical formula 1 or 2 has a glass transition temperature of greater than or equal to 120 ℃.
Another aspect of the embodiments of the present invention provides a display panel including an organic electroluminescent device, the organic electroluminescent device includes a substrate, an anode and a cathode oppositely disposed, a cap layer located on a side of the cathode away from the anode, and an organic functional layer located between the anode and the cathode, the organic functional layer includes an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, and a cap layer, at least one of the electron injection layer, the electron transport layer, and the light emitting layer includes the organic compound as described above.
According to one embodiment of the display panel of the present invention, an energy level difference of a LUMO energy level value of a material of the electron transport layer and a LUMO energy level value of a material of the light emitting layer or the electron injection layer is less than 0.2 eV; and the HOMO energy level value of the material of the electron transport layer is at least 0.3eV greater than the HOMO energy level value of the material of the electron injection layer.
According to one embodiment of the display panel of the present invention, the electron injection layer includes the above organic compound and a doping metal.
According to one embodiment of the display panel of the present invention, the doping metal is one or more selected from the group consisting of sodium, potassium, calcium, cesium, and ytterbium.
According to one embodiment of the display panel of the present invention, a content of the doping metal in the electron injection layer is 1 wt% to 5 wt%.
According to one embodiment of the display panel of the present invention, a content of the doping metal in the electron injection layer is 3 wt%.
In the organic light emitting device provided by the present invention, the anode material may be selected from metals such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc., and alloys thereof. The anode material may also be selected from metal oxides such as indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; the anode material may also be selected from conductive polymers such as polyaniline, polypyrrole, poly (3-methylthiophene), and the like. In addition, the anode material may also be selected from materials that facilitate hole injection in addition to the anode materials listed above, and combinations thereof, including known materials suitable for use as anodes.
In the organic light emitting device provided by the present invention, the cathode material may be selected from metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof. The cathode material may also be selected from multi-layered metallic materials such as LiF/Al, LiO2/Al、BaF2Al, etc. In addition to the cathode materials listed above, the cathode materials can also be materials that facilitate electron injection and combinations thereof, including materials known to be suitable as cathodes.
In the embodiment of the present invention, the manufacturing process of the organic light emitting device is as follows: 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. The organic thin layer can be formed by a known film formation method such as evaporation, sputtering, spin coating, dipping, ion plating, or the like. Finally, an organic optical cover layer CPL (cap layer) is prepared on the cathode. The materials of the electron injection layer, the electron transport layer and the light emitting layer can be the organic compounds described in the invention. The optical coating CPL can be produced by evaporation or solution processing. Solution processing methods include ink jet printing, spin coating, doctor blade coating, screen printing, roll-to-roll printing, and the like.
The novel organic compound designed above can be used as materials for electron injection layers, electron transport layers and light emitting layers.
Another aspect of the embodiments of the present invention provides a display device, which includes the display panel as described above.
The synthesis of organic compounds ET01, ET04, ET21, ET31 and ET36 is described below by way of example.
Example 1
Synthesis of Compound ET01
Figure BDA0001917752730000131
2-phenyl-1, 10-phenanthroline-4-chlorine (10mmol), 2-borate phenyl spirofluorene (10mmol) and Na2CO3(80mmol) were added to Toluene (Toluene)/absolute ethanol (EtOH)/H, respectively2O (75/25/50, mL) solvent to form a mixed solution, and then adding tetrakis (triphenylphosphine) palladium (Pd (PPh)3)40.48mmol) was added to the above mixed solution, and the reaction was refluxed for 20 hours under a nitrogen atmosphere. The resulting mixture was then cooled to room temperature and extracted with ethyl acetate. The aqueous layer was further extracted with dichloromethane and the organic layer was washed with brine, over MgSO4Drying was carried out, followed by filtration and concentration. The residue was recrystallized from dichloromethane and methanol to yield the compound ET01 as a white solid.
Compound ET01 (formula C)49H30N2) Results of elemental analysis of (1): theoretical value: c, 90.99; h, 4.68; n, 4.33. Test values are: c, 90.99; h, 4.67; n, 4.34. ESI-MS (M/z) (M +) by liquid mass spectrometry combined analysis: the theoretical value is 646.24 and the test value is 646.47.
Example 2
Synthesis of Compound ET04
Figure BDA0001917752730000141
2-phenyl-1, 10-phenanthroline-4-chloro (10mmol), 4-boronate phenylspirofluorene (10mmol) and Na2CO3(80mmol) were added to toluene/EtOH/H, respectively2O (75/25/50, mL) solvent to form a mixed solution, and then adding Pd (PPh)3)4(0.48mmol) was added to the above mixed solution, and the reaction was refluxed for 20 hours under a nitrogen atmosphere. The resulting mixture was then cooled to room temperature and extracted with ethyl acetate. The aqueous layer was further extracted with dichloromethane and the organic layer was washed with brine, over MgSO4Drying was carried out, followed by filtration and concentration. The residue was recrystallized from dichloromethane and methanol to yield the compound ET04 as a white solid.
Compound ET04 (formula C)49H30N2) Results of elemental analysis of (1): theoretical value: c, 90.99; h, 4.68; n, 4.33. Test values are: c, 90.99; h, 4.67; n, 4.34. ESI-MS (M/z) (M +) by liquid mass spectrometry combined analysis: the theoretical value is 646.24 and the test value is 646.30.
Example 3
Synthesis of Compound ET21
Figure BDA0001917752730000151
2-pyridyl-1, 10-phenanthroline-4-chlorine (20mmol), 2, 7-diboronate phenyl spirofluorene (10mmol) and Na2CO3(80mmol) were added to toluene/EtOH/H, respectively2O (75/25/50, mL) solvent to form a mixed solution, and then adding Pd (PPh)3)4(0.48mmol) was added to the above mixed solution, and the reaction was refluxed for 20 hours under a nitrogen atmosphere. The resulting mixture was then cooled to room temperature and extracted with ethyl acetate. The aqueous layer was further extracted with dichloromethane and the organic layer was washed with brine, over MgSO4Drying was carried out, followed by filtration and concentration. The residue was recrystallized from dichloromethane and methanol to yield the compound ET21 as a white solid.
Compound ET21 (formula C)71H42N6) Results of elemental analysis of (1): theoretical value: c, 87.09; h, 4.32; and N, 8.58. Test values are: c, 87.10; h, 4.33; n, 8.56. ESI-MS (M/z) (M +) by liquid mass spectrometry combined analysis: the theoretical value is 978.35 and the test value is 978.42.
Example 4
Synthesis of Compound ET33
Figure BDA0001917752730000152
2, 7-phenyl-1, 10-phenanthroline-4-chlorine (10mmol), 4-borate phenanthryl spirofluorene (10mmol) and Na2CO3(80mmol) were added to toluene/EtOH/H, respectively2O (75/25/50, mL) solvent to form a mixed solution, and then adding Pd (PPh)3)4(0.48mmol) was added to the above mixed solution, and the reaction was refluxed for 20 hours under a nitrogen atmosphere. The resulting mixture was then cooled to room temperature and extracted with ethyl acetate. The aqueous layer was further extracted with dichloromethane and the organic layer was washed with brine, over MgSO4Drying was carried out, followed by filtration and concentration. The residue was recrystallized from dichloromethane and methanol to yield the compound ET33 as a white solid.
Elemental analysis (formula C) of Compound ET3357H34N2): theoretical value: c, 89.28; h, 5.04; and N, 5.68. Test values are: c, 89.28; h, 5.02; and N, 5.70. ESI-MS (M/z) (M +) by liquid mass spectrometry combined analysis: the theoretical value is 739.30 and the test value is 739.41.
Example 5
Synthesis of Compound ET38
Figure BDA0001917752730000161
2-pyridyl-1, 10-phenanthroline-4-chloro (20mmol), 4-boronate phenylspirofluorene (10mmol) and Na2CO3(80mmol) were added to toluene/EtOH/H, respectively2O (75/25/50, mL) solvent to form a mixed solution, and then adding Pd (PPh)3)4(0.48mmol) was added to the above mixed solution, and the reaction was refluxed for 20 hours under a nitrogen atmosphere. The resulting mixture was then cooled to room temperature and extracted with ethyl acetate. The aqueous layer was further extracted with dichloromethane and the organic layer was washed with brine, over MgSO4Drying was carried out, followed by filtration and concentration. The residue was recrystallized from dichloromethane and methanol to yield the compound ET38 as a white solid.
Elemental analysis result of Compound ET38 (formula C)48H31N3): theoretical value: c, 88.72; h, 4.81; and N, 6.47. Test values are: c, 88.72; h, 4.82; and N, 6.46. ESI-MS (M/z) (M +) by liquid mass spectrometry combined analysis: the theoretical value is 649.25 and the test value is 649.40.
Device example 1
The present embodiment provides an organic light emitting device. As shown in fig. 3, the organic light emitting device includes: the structure of the LED comprises a glass substrate 1, an ITO 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 (a magnesium-silver electrode, the mass ratio of magnesium to silver is 9:1) and a cap layer (CPL)9, wherein the thickness of the ITO anode 2 is 15nm, the thickness of the first hole transport layer 3 is 10nm, the thickness of the second hole transport layer 4 is 95nm, the thickness of the light emitting layer 5 is 30nm, the thickness of the first electron transport layer 6 is 35nm, the thickness of the second electron transport layer 7 is 5nm, the thickness of the magnesium-silver electrode 8 is 15nm and the thickness of the cap layer (CPL)9 is 100 nm.
The organic light-emitting device of the present invention is prepared by the following steps:
1) the glass substrate 1 was cut into a size of 50mm × 50mm × 0.7mm, ultrasonically treated in isopropanol and deionized water, respectively, for 30 minutes, and then exposed to ozone for about 10 minutes to perform cleaning; mounting the resulting glass substrate with the ITO anode 2 on a vacuum deposition apparatus;
2) evaporating a hole injection layer material HAT-CN on the ITO anode 2 in a vacuum evaporation mode to obtain a layer with the thickness of 10nm, wherein the layer is used as a first hole transport layer 3;
3) depositing TAPC, a material for the second hole transport layer 4, on the first hole transport layer 3 by vacuum evaporation to obtain a layer having a thickness of 110nm as the second hole transport layer 4;
4) co-depositing a light-emitting layer 5 on the hole transport layer 4, wherein the DPVBi is used as a host material, the BCzVBi is used as a doping material, the mass ratio of the DPVBi to the BCzVBi is 1:19, and the thickness of the light-emitting layer 5 is 30 nm;
5) vacuum evaporating a first electron transport layer 6 material ET01 on the light emitting layer 5 to obtain a first electron transport layer 6 with the thickness of 30 nm;
6) vacuum evaporating a material Alq3 of the second electron transport layer 7 on the first electron transport layer 6 to obtain the second electron transport layer 7 with the thickness of 5 nm;
7) performing vacuum evaporation on the second electron transport layer 7 to obtain a cathode 8 with the thickness of 15nm, wherein the mass ratio of Mg to Ag is 9: 1;
8) a hole-type material CBP having a high refractive index was vacuum-deposited on the cathode 8 to a thickness of 100nm and used as a cathode capping layer (cap layer or CPL).
In this embodiment, the thickness and the mass ratio of the materials of each film layer are an embodiment of the present invention, and do not represent a limitation to the present invention.
Figure BDA0001917752730000181
Device example 2
In comparison with device example 1, device example 2 was fabricated using the same materials for each layer except that the first electron transport layer 6 was ET 04.
Figure BDA0001917752730000191
Device example 3
Device example 3 was made using the same materials as device example 1, except that the first electron transport layer 6 was ET 21.
Figure BDA0001917752730000192
Device example 4
Device example 4 was made using the same materials as device example 1, except that the first electron transport layer 6 was ET 33.
Figure BDA0001917752730000193
Device example 5
Device example 5 was made using the same materials as device example 1, except that the first electron transport layer 6 was ET 36.
Figure BDA0001917752730000201
Comparative device example 1
In comparison with device example 1, the fabrication process of device example 1 was the same for each layer except that the first electron transport layer 6 was BPhen.
Figure BDA0001917752730000202
Table 1: test result table of device examples and device comparative examples
Numbering ET material Drive voltage (V) Efficiency EQE/% E/CIEy
Device example 1 ET01 3.85 5.21％ 74.1
Device example 2 ET04 3.89 5.03％ 72.6
Device example 3 ET21 3.82 5.01％ 76.5
Device example 4 ET33 3.86 5.52％ 79.6
Device example 5 ET36 3.79 5.08％ 75.0
Comparative device example 1 BPhen 4.08 4.13％ 62.4
As can be seen from table 1 above, the optical device using the organic compound of the present invention has lower driving voltage, higher current efficiency, higher luminance, and longer lifetime, compared to comparative device 1.
It is a further aspect of embodiments of the present invention to provide an organic light emitting display device including the organic light emitting display panel as described above.
In the present invention, the organic light emitting device may be an OLED, which may be used in an organic light emitting display device, wherein the organic light emitting display device may be a display screen of a mobile phone, a computer display screen, a display screen of a liquid crystal television, a display screen of a smart watch, a display panel of a smart car, a display screen of a VR or AR helmet, a display screen of various smart devices, and the like. Fig. 4 is a schematic diagram of a display device according to an embodiment of the present invention, and in fig. 4, 10 denotes a display screen of a mobile phone.
Although the present application has been described with reference to preferred embodiments, it is not intended to limit the scope of the claims, and many possible variations and modifications may be made by one skilled in the art without departing from the spirit of the application.

Claims (12)

1. An organic compound having a structure represented by chemical formula 1 or chemical formula 2:
Figure FDA0002687450870000011
wherein L is1To L4Each independently selected from substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C5 to C30 heteroarylene, substituted or unsubstituted C1 to C8 alkylene, or substituted or unsubstituted C1 to C8 alkyleneoxy;
a. b, c, d, e and f represent numbers 0 and 1 respectively and independently, a + b + c + d is more than or equal to 1, and e + f is more than or equal to 1;
and a is 1, b is 1, c is 0;
or a is 1, c is 1, b is 0;
or a, b, c, d, 1;
or a, b, c, 1, d, 0;
or e ═ f ═ 1;
Ar1、Ar2、Ar3and Ar4Each independently has a structure represented by chemical formula 3:
Figure FDA0002687450870000012
wherein R is21Selected from substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl;
R22to R26Each independently selected from a hydrogen atom, a substituted or unsubstituted C6 to C18 aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted C1 to C16 alkyl group, a substituted or unsubstituted C1 to C16 alkoxy group, a hydroxyl group, or a carboxyl group;
R27selected from hydrogen atoms;
# denotes the attachment position in chemical formula 1 or chemical formula 2.
2. The organic compound of claim 1, wherein L is1And L2Independently represents one of the following structures:
Figure FDA0002687450870000021
Figure FDA0002687450870000031
Z1and Z2Each independently selected from a hydrogen atom, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 fused aryl group, a substituted or unsubstituted C6 to C30 fused heteroaryl group, a substituted or unsubstituted C1 to C16 alkylene group, a substituted or unsubstituted C1 to C16 alkyleneoxy group; and is
In chemical formulas 2-1 to 2-3, p represents any integer of numbers 0 to 4; in chemical formulas 2-4 to 2-8, p represents any integer of numbers 0 to 6; in chemical formulas 2-9 to 2-10, p represents any integer of numbers 0 to 5, and q represents any integer of numbers 0 to 3; in chemical formulas 2-11, 2-12, 2-18, 2-19 and 2-20, p represents any integer of numbers 0 to 2; in chemical formulas 2-15 to 2-17, p represents any integer of numbers 0 to 3;
wherein, # denotes the attachment position in chemical formula 1 or chemical formula 2.
3. The organic compound of claim 2, wherein L is1And L2Each independently represents one of the following structures:
Figure FDA0002687450870000041
wherein, # denotes the attachment position in chemical formula 1 or chemical formula 2.
4. The organic compound according to claim 1, wherein the organic compound is selected from one of the following compounds:
Figure FDA0002687450870000051
Figure FDA0002687450870000061
5. the organic compound according to any one of claims 1 to 4, wherein the organic compound has a glass transition temperature of 120 ℃ or higher.
6. A display panel comprising an organic electroluminescent device comprising a substrate, an anode and a cathode disposed opposite to each other, a cap layer on a side of the cathode facing away from the anode, and an organic functional layer between the anode and the cathode, the organic functional layer comprising an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, and a cap layer, at least one of the electron injection layer, the electron transport layer, and the light-emitting layer containing the organic compound according to any one of claims 1 to 5.
7. The display panel according to claim 6, wherein an energy level difference between a LUMO energy level value of a material of the electron transport layer and a LUMO energy level value of a material of the light emitting layer or the electron injection layer is less than 0.2 eV; and the HOMO energy level value of the material of the electron transport layer is at least 0.3eV greater than the HOMO energy level value of the material of the electron injection layer.
8. The display panel according to claim 6, wherein the electron injection layer comprises the organic compound according to any one of claims 1 to 5 and a doping metal.
9. The display panel according to claim 8, wherein the doping metal is one or more metals selected from sodium, potassium, calcium, cesium, and ytterbium.
10. The display panel according to claim 8, wherein the content of the dopant metal in the electron injection layer is 1 to 5 wt%.
11. The display panel according to claim 8, wherein the content of the doped metal in the electron injection layer is 3 wt%.
12. A display device characterized by comprising the display panel according to any one of claims 6 to 11.
CN201811580723.8A 2018-12-24 2018-12-24 Organic compound, display panel, and display device Active CN109503576B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201811580723.8A CN109503576B (en) 2018-12-24 2018-12-24 Organic compound, display panel, and display device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201811580723.8A CN109503576B (en) 2018-12-24 2018-12-24 Organic compound, display panel, and display device

Publications (2)

Publication Number Publication Date
CN109503576A CN109503576A (en) 2019-03-22
CN109503576B true CN109503576B (en) 2020-11-24

Family

ID=65755306

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201811580723.8A Active CN109503576B (en) 2018-12-24 2018-12-24 Organic compound, display panel, and display device

Country Status (1)

Country Link
CN (1) CN109503576B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111423436B (en) * 2020-03-31 2021-05-25 上海天马有机发光显示技术有限公司 Organic compound and application thereof
CN111848642B (en) * 2020-07-31 2023-01-24 武汉天马微电子有限公司 Compound, display panel and display device
CN113651836B (en) * 2021-08-18 2023-05-12 清华大学 Organic compound and organic electroluminescent device containing same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104603137A (en) * 2012-09-12 2015-05-06 出光兴产株式会社 Novel compound, material for organic electroluminescent element, and electronic device
CN104953037A (en) * 2014-03-31 2015-09-30 乐金显示有限公司 Organic light-emitting diode
CN105321984A (en) * 2014-08-01 2016-02-10 乐金显示有限公司 Organic light emitting display device
WO2018097648A1 (en) * 2016-11-25 2018-05-31 희성소재(주) Heterocyclic compound and organic light emitting element using same
CN108218858A (en) * 2016-12-12 2018-06-29 乐金显示有限公司 Organic compound and light emitting diode and organic LED display device including the organic compound

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104603137A (en) * 2012-09-12 2015-05-06 出光兴产株式会社 Novel compound, material for organic electroluminescent element, and electronic device
CN104953037A (en) * 2014-03-31 2015-09-30 乐金显示有限公司 Organic light-emitting diode
CN105321984A (en) * 2014-08-01 2016-02-10 乐金显示有限公司 Organic light emitting display device
WO2018097648A1 (en) * 2016-11-25 2018-05-31 희성소재(주) Heterocyclic compound and organic light emitting element using same
CN108218858A (en) * 2016-12-12 2018-06-29 乐金显示有限公司 Organic compound and light emitting diode and organic LED display device including the organic compound

Also Published As

Publication number Publication date
CN109503576A (en) 2019-03-22

Similar Documents

Publication Publication Date Title
CN109608452B (en) Organic compound, display panel, and display device
CN109748898B (en) Organic electroluminescent compound, preparation method thereof and organic electroluminescent device
CN110128424B (en) Compound, display panel and display device
CN107056750B (en) Compound with quaterphenyl as core and application thereof
CN109503576B (en) Organic compound, display panel, and display device
CN113264911A (en) Compound, organic light-emitting material and organic electroluminescent device
WO2023193775A1 (en) Organic electronic material comprising phenanthrene and phenanthroline, and application thereof
CN109503466A (en) Organic compound, display panel and display device
CN113937233B (en) Organic electroluminescent device and application thereof
CN111978292B (en) Compound and application thereof, and organic electroluminescent device comprising compound
CN114276310B (en) Organic compound and application thereof
CN115636755A (en) Naphthyl substituted diarylamine compound and application thereof
CN113321649B (en) Compound, electron transport material and organic electroluminescent device
CN114907281A (en) Organic photoelectric functional material containing special-shaped fluorene structure and application thereof
CN112028879B (en) Electron transport material, organic electroluminescent device and display device
CN111039971B (en) Boron-containing compound, display panel and display device
CN109585691B (en) Organic electroluminescent device containing fluorene derivative
CN111606866A (en) Organic compound and electroluminescent application thereof
CN115611891B (en) Quinoline-substituted phenanthroline compound and application thereof
CN115594599B (en) Bis-naphthalene compound and application thereof
CN115521253B (en) Bibiquinoline derivative compound and application thereof
CN114315882B (en) Organic compound and application thereof
CN115521292B (en) Quinoline substituted pyridine compound and application thereof
CN114349741B (en) Organic compound and application thereof
CN112159406B (en) Compound, display panel and display 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