CN116143735A - Organic electroluminescent compound, preparation method thereof and light-emitting display panel - Google Patents
Organic electroluminescent compound, preparation method thereof and light-emitting display panel Download PDFInfo
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- CN116143735A CN116143735A CN202111388708.5A CN202111388708A CN116143735A CN 116143735 A CN116143735 A CN 116143735A CN 202111388708 A CN202111388708 A CN 202111388708A CN 116143735 A CN116143735 A CN 116143735A
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- organic
- organic electroluminescent
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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Abstract
The invention discloses an organic electroluminescent compound, a preparation method thereof and a luminescent display panel comprising the compound, wherein the compound is introduced into naphthobenzofuran or naphthobenzofuran compounds, and under the condition of keeping higher Tg (glass ring transition temperature), the compound is promoted to form a conjugated large plane with other groups, so that a high refractive index is realized, and when the compound is used as a cap layer of an organic luminescent display device, microcavity effect can be regulated, so that the light extraction efficiency of a top-emission organic photoelectric device is improved. The arylamine compounds have higher extinction coefficients before 430nm, are favorable for ultraviolet light absorption, effectively block water and oxygen in the external environment, protect an OLED display panel from being corroded by the water and the oxygen, almost have no absorption after 430nm, and ensure light extraction efficiency, so that the organic EL element with high efficiency and long service life is realized.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to an organic electroluminescent compound, a preparation method thereof and a luminescent display panel.
Background
Organic electroluminescent devices (Organic Light Emitting Display, abbreviated as OLED) have made a long progress over decades as a new flat panel display. In both important fields of illumination and display, OLEDs have an important share, especially in the field of flat panel displays, where the word "large-screen small-screen people" has become a reality.
Until now, in order to realize the practical use of organic EL devices, various functions have been further subdivided, and an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are provided in this order in terms of function on a substrate. In the organic electroluminescent device, high efficiency and durability have been achieved by the light emitting element of the bottom light emitting structure emitting light from the bottom.
In such a light-emitting element, when light emitted from the light-emitting layer enters another film, the light enters the light-emitting layer at a certain angle or more, and is totally reflected at an interface between the light-emitting layer and the other film. Therefore, only a part of the emitted light can be utilized. In recent years, in order to improve the light extraction efficiency, it has been proposed to provide a high refractive index cap layer on the outer side of a semitransparent electrode having a low refractive index, to adjust the optical interference distance, suppress reflection of external light, and suppress extinction due to surface plasmon energy movement, thereby improving the light extraction efficiency and the light emission efficiency.
As the capping layer for adjusting the refractive index, use of aluminum (8-hydroxyquinoline) (hereinafter abbreviated as Alq 3) is known. Alq3 is often used as a green light emitting material or an electron transporting material, but has weak absorption around 450nm used for a blue light emitting element. Therefore, in the case of a blue light emitting element, there is a problem that color purity is lowered and light extraction efficiency is lowered.
The existing CPL material improves the light extraction efficiency to a certain extent. However, the refractive index of the existing CPL material is generally below 1.9, and the existing CPL material cannot meet the requirement of high refractive index, and has low luminous efficiency. In order to improve the characteristics of the organic EL element, in particular, to greatly improve the light extraction efficiency, it is necessary to develop a material having a high refractive index to improve the light extraction efficiency and solve the problem of the light emission efficiency. As the cap layer material, a material having a high refractive index and excellent film stability or durability is demanded.
Disclosure of Invention
In view of the above, the present invention is directed to an arylamine organic electroluminescent compound, a method for preparing the same, and a light-emitting display panel. The cap layer made of a material having no absorption in the wavelength region of blue, green and red has a high refractive index, excellent film stability and durability, and can greatly improve the light extraction efficiency and the light emission efficiency of an organic EL element.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
an organic electroluminescent compound has a structural general formula shown in chemical formula 1:
wherein X and Z are each independently selected from O or S;
Y 1 、Y 2 、Y 3 、Y 4 identical or different, and Y 1 -Y 4 Each independently selected from O, S, CR 1 R 2 、 SiR 3 R 4 Or NR (NR) 5 ；
L 1 、L 2 、L 3 Identical or different and L 1 -L 3 Each independently selected from substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted 3 to 30 membered heteroaryl; containing at least one heteroatom O, S, N or Si thereon;
ar is selected from substituted or unsubstituted C6-C30 aryl, and Ar can be combined with 1,2 position, 2,3 position or 3,4 position on benzene ring;
Ar 1 selected from substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 3-to 30-membered heterocycloalkyl containing at least one heteroatom O, S, N or Si; a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted 3-to 30-membered heteroaryl group having at least one heteroatom O, S, N or Si, and the heteroatom is preferably an N atom;
R 1 ～R 5 each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 3-to 30-membered heterocycloalkyl containing at least one heteroatom of O, S, N or Si; a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted 3-to 20-membered heteroaryl group having at least one heteroatom, preferably N, O, S, N or Si; substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C1-C20 alkylamino;
or alternatively, the first and second heat exchangers may be,
and one or more adjacent substituents to form a monocyclic or 3-to 30-membered alicyclic or aromatic ring, one or more carbon atoms of which may be replaced by at least one heteroatom selected from nitrogen, oxygen or sulfur.
Preferably, Y 1 、Y 2 、Y 3 And Y 4 Each independently selected from CR 3 R 4 。
Preferably, the L 1 -L 3 Each independently selected from the following structures:
preferably, said R 1 ～R 7 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 3-to 30-membered heterocycloalkyl containing at least one heteroatom, preferably N, O, S, N or Si; a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted 3-to 20-membered heteroaryl group having at least one heteroatom, preferably N, O, S, N or Si; substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylamine;
or alternatively, the first and second heat exchangers may be,
and one or more adjacent substituents to form a monocyclic or 3-to 30-membered alicyclic or aromatic ring, one or more carbon atoms of which may be replaced by at least one heteroatom selected from nitrogen, oxygen or sulfur.
Preferably, the Ar 1 Selected from the following structures:
preferably, the chemical formula 1 includes the following general formula:
in the present invention, the term "substituted" in the case of substitution or non-substitution means: the hydrogen atom bonded to the carbon atom of the compound becomes an additional substituent, and the position of substitution is not limited as long as the position is a position where the hydrogen atom is substituted (i.e., a position where a substituent may be substituted), and when two or more substituents are substituted, two or more substituents may be the same as or different from each other.
That is, "substituted" in the above "substituted or unsubstituted", a substituent which may be preferred is one or more of deuterium, cyano, halogen, nitro, hydroxy, phosphate, borane, silicon, C1-C10 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C20 aryl, 3-to 10-membered heteroaryl, C1-C10 alkoxy, C6-C20 arylamino.
Specifically, the chemical formula 1 is preferably selected from any one of the following structures:
another object of the present invention is to provide a method for preparing the above organic electroluminescent compounds, wherein the synthetic route is as follows:
in the above formula, ar 1 、X、Y 1 ～Y 4 、Z、L 1 、L 2 、L 3 Identical to the above formula 1, wherein Hal 1 ～Hal 2 Each independently selected from chlorine, bromine or iodine;
the preparation method comprises the following steps:
step one,
Under the protection of nitrogen, dissolving a raw material A and a raw material B in a mixed solution of toluene, ethanol and water, adding tetraphenylphosphine palladium and potassium carbonate, uniformly stirring, heating and refluxing to obtain an intermediate 1;
step two,
Under the protection of nitrogen, the intermediate 1 and the raw material C are dissolved in toluene solution, and tris (dibenzylideneacetone) dipalladium, tri-tert-butylphosphine and sodium tert-butoxide are added, stirred uniformly, heated and refluxed to obtain the chemical formula 1.
Preferably, the first step specifically includes:
under the protection of nitrogen, dissolving a raw material A (1.0 eq) and a raw material B (1.0 eq) in a mixed solution of toluene, ethanol and water (Vtol: V: V=3:1:1), adding tetraphenylphosphine palladium (0.01 eq) and potassium carbonate (2.0 eq), uniformly stirring, heating to 90 ℃, refluxing for 5 hours, keeping an organic phase after the solution is cooled to room temperature, and extracting an aqueous phase with ethyl acetate; after the organic phases were combined, drying was performed using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. Recrystallizing in toluene, filtering, eluting the filter cake with petroleum ether, and drying in a 65 deg.C oven for 12 hr to obtain intermediate 1;
the second step specifically comprises the following steps:
under the protection of nitrogen, dissolving an intermediate 1 (1.0 eq) and a raw material C (1.0 eq) in toluene solution, adding tris (dibenzylideneacetone) dipalladium (0.01 eq), tri-tert-butylphosphine (0.05 eq) and sodium tert-butoxide (2.0 eq), uniformly stirring, heating to 90 ℃, and carrying out reflux reaction for 5h; after the reaction, slightly reducing the temperature, filtering by using diatomite, removing salt and catalyst, cooling the filtrate to room temperature, washing with water for three times, retaining an organic phase, and extracting an aqueous phase with ethyl acetate; after the organic phases were combined, drying was performed using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. And (3) completely dissolving solid organic matters by using a small amount of dichloromethane, slowly dropwise adding the solution into petroleum ether solution, uniformly stirring, precipitating, filtering to obtain solid, eluting with absolute ethyl alcohol and petroleum ether in sequence, and drying to obtain the chemical formula 1.
Another object of the present invention is to provide an organic light emitting display panel including an organic light emitting device including a capping layer, an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. The material of at least one of the cap layer, the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer is the organic light emitting compound.
In the present invention, the cap layer thickness of the organic EL element is preferably in the range of 50nm to 70nm, more preferably in the range of 55nm to 65 nm.
In the present invention, the wavelength of the organic EL element cap layer before transmission is between 460nm and 620nm, and the refractive index of the cap layer is preferably 2.0 or more, more preferably 2.1 or more.
In the organic EL element of the present invention, the cap layer can be produced by laminating 2 or more different constituent materials.
In the organic light emitting display panel of 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; metal oxides such as indium oxide, zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and the like; the conductive polymer is, for example, polyaniline, polypyrrole, poly (3-methylthiophene), or the like. In addition to the above materials that facilitate hole injection and combinations thereof, the anode material may also include other known materials suitable for use as anodes.
In the organic light emitting display panel of the present invention, the cathode material may be selected from metals such as aluminum, magnesium, silver, indium, tin, titanium, etc. and alloys thereof, which improve quantum efficiency and stability of the device, and can form a stable and firm metal thin film on the organic film; the multilayer metal material such as LiF/Al, liO2/Al, baF2/Al, etc., can obtain higher luminous efficiency. In addition to the above materials and combinations thereof that facilitate electron injection, the cathode material may also include other known materials suitable for use as a cathode.
The organic light emitting display panel is manufactured by the following method: an anode is formed on a transparent or opaque smooth substrate, an organic layer is formed on the anode, and a cathode is formed on the organic layer. The organic thin layer may be formed by a known film forming method such as vapor deposition, sputtering, spin coating, dipping, ion plating, and the like. Finally, an organic optical capping layer CPL (capping layer) is prepared on the cathode. The material of the optical capping layer CPL is the arylamine compound. The optical capping layer CPL may be prepared by vapor deposition or solution processing. The solution processing method includes an inkjet printing method, spin coating, doctor blade coating, screen printing, roll-to-roll printing, and the like.
Compared with the prior art, the invention has the following beneficial effects:
since the organic EL element of the present invention uses an organic EL element material having a high refractive index, good film stability, and excellent durability as a material for the cap layer, the light extraction efficiency is greatly improved as compared with the known organic EL element, and thus a high-efficiency and long-life organic EL element can be achieved.
As the naphthobenzofuran or naphthobenzofuran compounds are introduced into the invention, under the condition of keeping higher Tg (glass ring transition temperature), the compound is promoted to form a conjugated large plane with other groups, so that a high refractive index is realized, and when the compound is used as a cap layer of an organic light-emitting display device, the microcavity effect can be regulated, thereby improving the light extraction efficiency of the top-emitting organic photoelectric device. The arylamine compounds have higher extinction coefficients before 430nm, are favorable for ultraviolet light absorption, effectively block water and oxygen in the external environment, protect an OLED display panel from being corroded by the water and the oxygen, almost have no absorption after 430nm, and ensure light extraction efficiency, so that the organic EL element with high efficiency and long service life is realized.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are required to be used in the embodiments or the description of the prior art will be briefly described below, and it is obvious that the drawings in the following description are only embodiments of the present invention, and that other drawings can be obtained according to the provided drawings without inventive effort for a person skilled in the art.
FIG. 1 is a graph of nk plots of compound 33, comparative compound 1, comparative compound 2 in the examples of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described 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.
Example 1
Under the protection of nitrogen, dissolving a raw material A-1 (30.00 mmol) and a raw material B-1 (30.00 mmol) in 130.00ml of mixed solution of toluene, ethanol and water (Vtol: V: V=3:1:1), adding tetraphenylphosphine palladium (0.30 mmol) and potassium carbonate (60.00 mmol), stirring uniformly, heating to 90 ℃ and refluxing for 5 hours, keeping an organic phase after the solution is cooled to room temperature, and extracting an aqueous phase with ethyl acetate; after the organic phases were combined, drying was performed using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. Recrystallizing in toluene, filtering, eluting the filter cake with petroleum ether, and drying in a 65 ℃ oven for 12h to obtain intermediate 1 (9.13 g, yield: 81.51%).
Under the protection of nitrogen, dissolving the intermediate 1 (24.11 mmol) and the raw material C-1 (24.11 mmol) in 180.00ml of toluene solution, adding tris (dibenzylideneacetone) dipalladium (0.24 mmol), tri-tert-butylphosphine (1.21 mmol) and sodium tert-butoxide (48.22 mmol), stirring uniformly, heating to 90 ℃, and refluxing for reaction for 5h; after the reaction, slightly reducing the temperature, filtering by using diatomite, removing salt and catalyst, cooling the filtrate to room temperature, washing with water for three times, retaining an organic phase, and extracting an aqueous phase with ethyl acetate; after the organic phases were combined, drying was performed using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. The solid organic matter was completely dissolved with a small amount of methylene chloride, and then slowly added dropwise into a petroleum ether solution, stirred uniformly, precipitated, suction-filtered to obtain a solid, which was rinsed with absolute ethyl alcohol and petroleum ether in sequence, and dried to prepare compound 1 (13.12 g, yield: 78.44%, mw: 693.80).
The obtained compound-1 was subjected to detection analysis, and the results were as follows:
HPLC purity: > 99%.
Mass spectrometry test: theoretical value 693.81; the test value was 693.47.
Elemental analysis:
the calculated values are: c,86.56; h,4.50; n,2.02; o,6.92.
The test values are: c,86.19; h,4.83; n,2.27; o,7.26.
Example 2
Under the protection of nitrogen, raw material A-33 (30.00 mmol) and raw material B-33 (30.00 mmol) are dissolved in 130.00ml of mixed solution of toluene, ethanol and water (Vtol: V: V=3:1:1), tetrakis triphenylphosphine palladium (0.30 mmol) and potassium carbonate (60.00 mmol) are added, stirred uniformly, heated to 90 ℃ and refluxed for 5 hours, after the solution is cooled to room temperature, the organic phase is retained, and then the aqueous phase is extracted with ethyl acetate; after the organic phases were combined, drying was performed using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. Recrystallizing in toluene, filtering, eluting the filter cake with petroleum ether, and drying in a 65 ℃ oven for 12h to obtain intermediate 1 (9.13 g, yield: 81.52%).
Under the protection of nitrogen, dissolving the intermediate 3 (24.11 mmol) and the raw material C-33 (24.11 mmol) in 180.00ml of toluene solution, adding tris (dibenzylideneacetone) dipalladium (0.24 mmol), tri-tert-butylphosphine (1.21 mmol) and sodium tert-butoxide (48.22 mmol), stirring uniformly, heating to 90 ℃ and refluxing for reaction for 5h; after the reaction, slightly reducing the temperature, filtering by using diatomite, removing salt and catalyst, cooling the filtrate to room temperature, washing with water for three times, retaining an organic phase, and extracting an aqueous phase with ethyl acetate; after the organic phases were combined, drying was performed using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. The solid organic matter was completely dissolved with a small amount of methylene chloride, and then slowly added dropwise to a petroleum ether solution, stirred uniformly, precipitated, suction-filtered to obtain a solid, which was rinsed with absolute ethyl alcohol and petroleum ether in this order, and dried to prepare compound 33 (13.10 g, yield: 78.31%, mw: 693.80).
The resulting compound-33 was subjected to detection analysis, and the results were as follows:
HPLC purity: > 99%.
Mass spectrometry test: theoretical value 693.80; the test value was 693.35.
Elemental analysis:
the calculated values are: c,86.56; h,4.50; n,2.02; o,6.92.
The test values are: c,86.22; h,4.71; n,2.41; o,7.25.
Example 3
Under the protection of nitrogen, dissolving raw material A-52 (30.00 mmol) and raw material B-52 (30.00 mmol) in 180.00ml of mixed solution of toluene, ethanol and water (Vtol: V: V=3:1:1), adding tetraphenylphosphine palladium (0.30 mmol) and potassium carbonate (60.00 mmol), stirring uniformly, heating to 90 ℃ and refluxing for 5 hours, after the solution is cooled to room temperature, retaining an organic phase, and extracting an aqueous phase with ethyl acetate; after the organic phases were combined, drying was performed using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. Recrystallizing in toluene, filtering, eluting the filter cake with petroleum ether, and drying in an oven at 65deg.C for 12h to obtain intermediate 1 (10.79 g, yield: 80.06%).
Intermediate 3 (22.25 mmol) and raw material C-52 (22.25 mmol) were dissolved in 220.00ml toluene solution under nitrogen protection, tris (dibenzylideneacetone) dipalladium (0.22 mmol), tri-tert-butylphosphine (1.12 mmol) and sodium tert-butoxide (44.50 mmol) were added, stirred well, warmed to 90 ℃ and reacted under reflux for 5h; after the reaction, slightly reducing the temperature, filtering by using diatomite, removing salt and catalyst, cooling the filtrate to room temperature, washing with water for three times, retaining an organic phase, and extracting an aqueous phase with ethyl acetate; after the organic phases were combined, drying was performed using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. The solid organic matter was completely dissolved with a small amount of methylene chloride, and then slowly added dropwise into a petroleum ether solution, stirred uniformly, precipitated, suction-filtered to obtain a solid, which was rinsed with absolute ethyl alcohol and petroleum ether in this order, and dried to prepare compound 52 (15.77 g, yield: 76.83%, mw: 922.10).
The resulting compound-52 was subjected to detection analysis, and the results were as follows:
HPLC purity: > 99%.
Mass spectrometry test: theoretical value 920.10; the test value was 919.87.
Elemental analysis:
the calculated values are: c,88.58; h,4.70; n,1.52; o,5.21.
The test values are: c,88.18; h,4.96; n,1.77; o,5.56.
The synthesis methods of other compounds are the same as those of the above examples, and are not described in detail herein, and mass spectra and molecular formulas of other synthesis examples are shown in table 1 below:
table 1:
with the compound of the present invention and comparative compound 1 and comparative compound 2 (structural formulas of comparative compound 1 and comparative compound 2 are shown below), a vapor deposited film having a film thickness of 50nm was formed on a substrate, refractive indexes at 450nm, 530nm and 635nm were measured using a spectroscopic measuring device, and the measurement results are summarized in table 2, and a nk coefficient graph is shown in fig. 1.
Table 2: thermal performance and refractive index test results
As can be seen from Table 2, the refractive index of the compound prepared by the invention is above 2.0 under the wavelengths of 450nm, 530nm and 635nm, which accords with the refractive index requirement of the light emitting device on CPL, the extinction coefficient k value is almost 0 after the blue light wavelength is 430nm, and the light emission of the light emitting layer material in the blue light region is not influenced. Thus, higher luminous efficiency can be brought about. In addition, it can be found in Table 2 that the glass transition temperatures of the compounds are all higher than 130 ℃, which means that the thin film state is stable in the compounds of the present invention. As can be seen more intuitively in fig. 1, the n values of the inventive compound 33 are higher than those of the comparative compound, thereby indicating that the luminous efficiency of the inventive compound is higher than those of the comparative compound 1 and the comparative compound 2.
Device example 1 (Red light device)
The following examples provide the application of the aromatic amine compound of the present invention to an organic light emitting device, illustrating the technical effects achieved by the aromatic amine compound of the present invention in practical applications.
The structure of the prepared OLED device is as follows: ITO anode/HIL/HTL/EML/ETL/EIL/cathode/light extraction layer
a. ITO anode: the thickness of the coating is equal to
The ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate is washed for 2 times in distilled water, ultrasonic wave is used for washing for 30min, then distilled water is used for repeatedly washing for 2 times, ultrasonic wave is used for washing for 10min, methanol, acetone and isopropanol are used for ultrasonic wave washing (5 min for washing each time) in sequence after washing is finished, drying is carried out, then the glass substrate is transferred into a plasma washer for washing for 5min, and then the glass substrate is sent into an evaporation machine, the substrate is used as an anode, and other functional layers are sequentially evaporated on the substrate.
b. HIL (hole injection layer): to be used for
The vacuum evaporation hole injection layer materials HT-1 and P-dock are shown in the chemical formula below. The evaporation rate ratio of HT-1 to P-dock is 97:3, the thickness is 10nm;
c. HTL (hole transport layer): to be used for
Vacuum evaporating 130nm HT-1 as a hole transport layer on the hole injection layer;
d. light-emitting auxiliary layer: to be used for
Vacuum evaporating 95nm EB-1 as a light-emitting auxiliary layer on the hole injection layer;
e. EML (light emitting layer): then on the light-emitting auxiliary layer to
Is used for vacuum evaporation of a Host material (Host) and a dopant material (D) having a thickness of 40nmopant) as the light emitting layer, the chemical formulas of Host and Dopant thereof are shown below. Wherein the evaporation rate ratio of Host to Dopant is 97: 3.
f. HB (hole blocking layer): to be used for
HB having a thickness of 5.0nm was vacuum deposited as a hole blocking layer.
g. ETL (electron transport layer): to be used for
ET-1 and Liq having a thickness of 35nm were vacuum-deposited as electron transport layers, and the chemical formula of ET-1 is shown below. Wherein the ratio of the evaporation rates of ET-1 and Liq is 50:50.
h. EIL (electron injection layer): to be used for
The vapor deposition rate of Yb film layer was 1.0nm to form an electron injection layer.
i. And (3) cathode: to be used for
The vapor deposition rate ratio of magnesium and silver is 18nm, and the vapor deposition rate ratio is 1:9, so that the OLED device is obtained.
j. Light extraction layer: to be used for
The compound 1 provided in the above example having a thickness of 70nm was vacuum-deposited on the cathode as a light extraction layer.
k. And packaging the evaporated substrate. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The chemical structural formula of the corresponding compound applied to the device is shown as follows:
device examples 2 to 8
Organic electroluminescent devices were fabricated by replacing the cathode capping layer materials with the compounds 20, 31, 33, 41, 52, 64, and 84, respectively, in the same manner as in device example 1, and were designated as device examples 2 to 8, respectively.
Device comparative example 1
An organic electroluminescent device comparative example 1 was prepared in the same manner as in device example 1. Except that the CPL layer material compound was replaced with comparative compound 1, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 1 is shown as follows:
device comparative example 2
An organic electroluminescent device comparative example 1 was prepared in the same manner as in device example 1. Except that the CPL layer material compound was replaced with comparative compound 2, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 2 is shown as follows:
device comparative example 3
An organic electroluminescent device comparative example 3 was prepared in the same manner as in device example 1. Except that the CPL layer material compound was replaced with comparative compound 3, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 3 is shown as follows:
device comparative example 4
An organic electroluminescent device comparative example 4 was prepared in the same manner as in device example 1. Except that the CPL layer material compound was replaced with the comparative compound 4, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 4 is shown as follows:
the organic electroluminescent devices obtained in the above device examples 1 to 8 and device comparative examples 1 to 4 were characterized in terms of driving voltage, luminous efficiency and lifetime at 6000 (nits) luminance, and the test results are shown in table 3 below:
table 3:
device example 9 (Green light device)
The following examples provide the application of the aromatic amine compound of the present invention to an organic light emitting device, illustrating the technical effects achieved by the aromatic amine compound of the present invention in practical applications.
The structure of the prepared OLED device is as follows: ITO anode/HIL/HTL/EML/ETL/EIL/cathode/light extraction layer
a. ITO anode: the thickness of the coating is equal to
The ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate is washed for 2 times in distilled water, ultrasonic wave is used for washing for 30min, then distilled water is used for repeatedly washing for 2 times, ultrasonic wave is used for washing for 10min, methanol, acetone and isopropanol are used for ultrasonic wave washing (5 min for washing each time) in sequence after washing is finished, drying is carried out, then the glass substrate is transferred into a plasma washer for washing for 5min, and then the glass substrate is sent into an evaporation machine, the substrate is used as an anode, and other functional layers are sequentially evaporated on the substrate.
b. HIL (hole injection layer): to be used for
The vacuum evaporation hole injection layer materials HT-1 and P-dock are shown in the chemical formula below. The evaporation rate ratio of HT-1 to P-dock is 97:3, the thickness is 10nm;
c. HTL (hole transport layer): to be used for
Vacuum evaporating 130nm HT-1 as a hole transport layer on the hole injection layer;
d. light-emitting auxiliary layer: to be used for
Vacuum evaporating 45nm EB-2 on the hole transmission layer as a light-emitting auxiliary layer;
e. EML (light emitting layer): then on the light-emitting auxiliary layer to
Host materials (Host-1 and Host-2) and Dopant materials (Dopant) having a thickness of 40nm were vacuum-evaporated as light-emitting layers, and the chemical formulas of Host-1, host-2 and Dopant were as follows. The evaporation rate ratio of the Host materials (Host-1 and Host-2) to the Dopant material (Dopant) was 94:6, wherein the evaporation rate ratio of Host-1 to Host-2 is 4:6./>
f. HB (hole blocking layer): to be used for
HB having a thickness of 5.0nm was vacuum deposited as a hole blocking layer.
g. ETL (electron transport layer): to be used for
ET-1 and Liq having a thickness of 35nm were vacuum-deposited as electron transport layers, and the chemical formula of ET-1 is shown below. Wherein the ratio of the evaporation rates of ET-1 and Liq is 50:50.
h. EIL (electron injection layer): to be used for
The vapor deposition rate of Yb film layer was 1.0nm to form an electron injection layer.
i. And (3) cathode: to be used for
Vapor deposition rate ratio of (2)Magnesium and silver with 18nm vapor deposition rate ratio of 1:9 to obtain OLED device.
j. Light extraction layer: to be used for
The compound 1 provided in the above example having a thickness of 70nm was vacuum-deposited on the cathode as a light extraction layer.
k. And packaging the evaporated substrate. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The chemical structural formula of the corresponding compound applied to the device is shown as follows:
device examples 10 to 16
Organic electroluminescent devices, designated as device examples 10 to 16, were fabricated by replacing the cathode capping layer materials with the compounds 20, 31, 33, 41, 52, 64, and 84, respectively, in the same manner as in device example 1.
Device comparative example 5
An organic electroluminescent device comparative example 5 was prepared in the same manner as in device example 9. Except that the CPL layer material compound was replaced with comparative compound 1, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 1 is shown as follows:
device comparative example 6
An organic electroluminescent device comparative example 6 was prepared in the same manner as in device example 9. Except that the CPL layer material compound was replaced with comparative compound 2, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 2 is shown as follows:
device comparative example 7
An organic electroluminescent device comparative example 7 was prepared in the same manner as in device example 9. Except that the CPL layer material compound was replaced with comparative compound 3, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 3 is shown as follows:
device comparative example 8
An organic electroluminescent device comparative example 8 was prepared in the same manner as in device example 9. Except that the CPL layer material compound was replaced with the comparative compound 4, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 4 is shown as follows:
the organic electroluminescent devices obtained in the above device examples 9 to 16 and device comparative examples 5 to 8 were characterized in terms of driving voltage, luminous efficiency and lifetime at 15000 (nits) luminance, and the test results are shown in table 3 below:
table 4:
device example 17 (blue light device)
The following examples provide the application of the aromatic amine compound of the present invention to an organic light emitting device, illustrating the technical effects achieved by the aromatic amine compound of the present invention in practical applications.
The structure of the prepared OLED device is as follows: ITO anode/HIL/HTL/EML/ETL/EIL/cathode/light extraction layer
a. ITO anode: the thickness of the coating is equal to
The ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate was washed 2 times in distilled water, and ultrasonic wave was appliedWashing for 30min, repeatedly washing with distilled water for 2 times, ultrasonic washing for 10min, sequentially ultrasonic washing with methanol, acetone and isopropanol (5 min each time), drying, transferring into a plasma cleaning machine, washing for 5min, transferring into a vapor deposition machine, taking the substrate as anode, and sequentially evaporating other functional layers thereon.
b. HIL (hole injection layer): to be used for
The vacuum evaporation hole injection layer materials HT-1 and P-dock are shown in the chemical formula below. The evaporation rate ratio of HT-1 to P-dock is 97:3, the thickness is 10nm;
c. HTL (hole transport layer): to be used for
Vacuum evaporating 130nm HT-1 as a hole transport layer on the hole injection layer;
d. light-emitting auxiliary layer: to be used for
Vacuum evaporating EB-3 of 5nm on the hole transmission layer as a light-emitting auxiliary layer;
e. EML (light emitting layer): then on the light-emitting auxiliary layer to
The Host material (Host) and the Dopant material (Dopant) having a thickness of 20nm were vacuum-deposited as light-emitting layers, and the chemical formulas of Host and Dopant are shown below. Wherein the evaporation rate ratio of Host to Dopant is 98: 2.
f. HB (hole blocking layer): to be used for
HB having a thickness of 5.0nm was vacuum deposited as a hole blocking layer. />
g. ETL (electron transport layer): to be used for
ET-1 and Liq having a thickness of 35nm were vacuum-deposited as electron transport layers, and the chemical formula of ET-1 is shown below. Wherein the ratio of the evaporation rates of ET-1 and Liq is 50:50.
h. EIL (electron injection layer): to be used for
The vapor deposition rate of Yb film layer was 1.0nm to form an electron injection layer.
i. And (3) cathode: to be used for
The vapor deposition rate ratio of magnesium and silver is 18nm, and the vapor deposition rate ratio is 1:9, so that the OLED device is obtained.
j. Light extraction layer: to be used for
The compound 1 provided in the above example having a thickness of 70nm was vacuum-deposited on the cathode as a light extraction layer.
k. And packaging the evaporated substrate. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
The chemical structural formula of the corresponding compound applied to the device is shown as follows:
device examples 18 to 24
Organic electroluminescent devices, designated as device examples 18 to 24, were fabricated by replacing the cathode capping layer materials with the compounds 20, 31, 33, 41, 52, 64, and 84, respectively, in the same manner as in device example 1.
Device comparative example 9
An organic electroluminescent device comparative example 9 was prepared in the same manner as in device example 17. Except that the CPL layer material compound was replaced with comparative compound 1, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 1 is shown as follows:
device comparative example 10
Organic electroluminescent device comparative example 10 was prepared according to the method of device example 17. Except that the CPL layer material compound was replaced with comparative compound 2, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 2 is shown as follows:
device comparative example 11
Organic electroluminescent device comparative example 11 was prepared according to the method of device example 17. Except that the CPL layer material compound was replaced with comparative compound 3, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 3 is shown as follows:
device comparative example 12
Organic electroluminescent device comparative example 12 was prepared according to the method of device example 17. Except that the CPL layer material compound was replaced with the comparative compound 4, and the other materials, such as the luminescent layer material, were all the same. Wherein, the structural formula of the comparative compound 4 is shown as follows:
the organic electroluminescent devices obtained in the above device examples 17 to 24 and device comparative examples 9 to 12 were characterized in terms of driving voltage, luminous efficiency and lifetime at a luminance of 1000 (nits), and the test results were shown in table 3 below:
table 5:
as can be seen from the above tables 3 to 5, the use of the compound of the present invention for the preparation of red light device, green light device, and blue light device, respectively, significantly improved the luminous efficiency of the devices using the compound of the present invention as CPL material, as compared with the device comparative examples 1 to 6. This means: by including a compound having a high refractive index in the cap layer, light extraction efficiency can be greatly improved. The compound of the present invention has a high light absorption coefficient and a high refractive index, and can significantly improve light extraction efficiency and has a stable thin film state, and therefore is a very excellent compound for organic EL elements. The organic EL element prepared by the compound can improve the luminous efficiency of the device and is an ideal CPL material.
In the present specification, each embodiment is described in a progressive manner, and each embodiment is mainly described in a different point from other embodiments, and identical and similar parts between the embodiments are all enough to refer to each other. For the device disclosed in the embodiment, since it corresponds to the method disclosed in the embodiment, the description is relatively simple, and the relevant points refer to the description of the method section.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. An organic electroluminescent compound is characterized in that the structural general formula is shown in chemical formula 1:
wherein X and Z are each independently selected from O or S;
Y 1 -Y 4 each independently selected from O, S, CR 1 R 2 、SiR 3 R 4 Or NR (NR) 5 ；
L 1 -L 3 Each independently selected from substituted or unsubstituted C6 to C60 aryl or substituted or unsubstituted 3 to 30 membered heteroaryl;
ar is selected from substituted or unsubstituted C6-C30 aryl, and Ar can be combined with 1,2 position, 2,3 position or 3,4 position on benzene ring;
Ar 1 selected from substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 3-to 30-membered heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted 3-to 30-membered heteroaryl;
R 1 ～R 5 each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 3-to 30-membered heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted 3-to 20-membered heteroaryl, substituted or unsubstituted C6-to 60-aryloxy, substituted or unsubstituted C1-to 20-alkoxy, substituted or unsubstituted C6-to 60-arylamino, substituted or unsubstituted C1-to 20-alkylamino;
or alternatively, the first and second heat exchangers may be,
and one or more adjacent substituents to form a monocyclic or 3-to 30-membered alicyclic or aromatic ring, one or more carbon atoms of which may be replaced by at least one heteroatom selected from nitrogen, oxygen or sulfur.
2. An organic electroluminescent compound according to claim 1, wherein the L 1 -L 3 Each independently selected from the following structures:
3. an organic electroluminescent compound according to claim 1, wherein R is 1 ～R 7 Each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 3-to 30-membered heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted 3-to 20-membered heteroaryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylamino;
or alternatively, the first and second heat exchangers may be,
and one or more adjacent substituents to form a monocyclic or 3-to 30-membered alicyclic or aromatic ring, one or more carbon atoms of which may be replaced by at least one heteroatom selected from nitrogen, oxygen or sulfur.
4. An organic electroluminescent compound according to claim 1, wherein Ar 1 Selected from the following structures:
5. an organic electroluminescent compound according to claim 3, wherein the chemical formula 1 comprises the following general formula:
6. the method for producing an organic electroluminescent compound as claimed in any one of claims 1 to 5, wherein the synthetic route is as follows:
in the above formula, ar 1 、X、Y 1 ～Y 4 、Z、L 1 、L 2 、L 3 Identical to the partial representations of formula 1 as defined in any one of claims 1 to 6, wherein Hal 1 ～Hal 2 Each independently selected from chlorine, bromine or iodine;
the preparation method comprises the following steps:
step one,
Under the protection of nitrogen, dissolving a raw material A and a raw material B in a mixed solution of toluene, ethanol and water, adding tetraphenylphosphine palladium and potassium carbonate, uniformly stirring, heating and refluxing to obtain an intermediate 1;
step two,
Under the protection of nitrogen, the intermediate 1 and the raw material C are dissolved in toluene solution, and tris (dibenzylideneacetone) dipalladium, tri-tert-butylphosphine and sodium tert-butoxide are added, stirred uniformly, heated and refluxed to obtain the chemical formula 1.
7. The method for preparing an organic electroluminescent compound according to claim 6, wherein the molar ratio of the raw material a, the raw material B, the tetraphenylphosphine palladium and the potassium carbonate in the first step is 1:1:0.01:2; the volume ratio of toluene, ethanol and water is 3:1:1; the temperature rise temperature is 90 ℃, and the reflux time is 5 hours.
8. The method for preparing an organic electroluminescent compound according to claim 6, wherein in the second step, the molar ratio of the intermediate 1 to the raw material C to the tri (dibenzylideneacetone) dipalladium to the tri-tert-butylphosphine to the sodium tert-butoxide is 1:1:0.01:0.05:2; the temperature rise temperature is 90 ℃, and the reflux time is 5 hours.
9. An organic light emitting display panel comprising an organic light emitting device, wherein the organic light emitting device comprises a cap layer, an anode, a cathode, and an organic layer between the anode and the cathode, wherein at least one of the organic layer and the cap layer comprises the organic electroluminescent compound of any one of claims 1-5.
10. The light-emitting display panel according to claim 9, wherein the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and at least one of the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, and the electron injection layer contains the organic electroluminescent compound according to any one of claims 1 to 5.
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