CN111039969A - Organic compound, display panel and display device - Google Patents
Organic compound, display panel and display device Download PDFInfo
- Publication number
- CN111039969A CN111039969A CN201911399670.4A CN201911399670A CN111039969A CN 111039969 A CN111039969 A CN 111039969A CN 201911399670 A CN201911399670 A CN 201911399670A CN 111039969 A CN111039969 A CN 111039969A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- organic compound
- organic
- light emitting
- 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.)
- Granted
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
-
- 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
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen 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
- H10K85/654—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
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur 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
-
- 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
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- 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
- C09K2211/1011—Condensed systems
-
- 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
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
-
- 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
-
- 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
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
Abstract
The application discloses an organic compound, which has the following structural general formula:
R1、R2、R3、R4each independently selected from hydrogen, substituted or unsubstituted C4-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, substituted or unsubstituted C4-C40 fused aryl, and substituted or unsubstituted C4-C40 fused heteroaryl. The organic compound is a material with the thermal activation delayed fluorescence property, is used as a host or guest material of a light-emitting layer of an organic electroluminescent device, but is not limited to the light-emitting layer, and can greatly improve the performance of the device because the material can utilize triplet state energy.
Description
Technical Field
The present disclosure relates to organic electroluminescent materials, and particularly to an organic compound, a display panel and a display device.
Background
According to the light emitting mechanism, there are mainly 4 kinds of materials available for the light emitting layer of the OLED:
1. fluorescent material
The singlet excited state S1 of the material transitions back to the ground state S0 by radiation.
2. Phosphorescent material
The triplet excited state T1 radiatively decays directly to the ground state S0(Nature,1998,395,151).
3. Triplet-triplet annihilation (TTA) material
Two triplet excitons interact to generate a singlet exciton which transitions back to the ground state S0 by radiation (adv. funct. mater.,2013,23, 739).
4. Thermally Activated Delayed Fluorescence (TADF) material
When the energy gap between the S1 state and the T1 state is small and the lifetime of the T1 state exciton is long, under a certain temperature condition, the T1 state exciton can realize the process of T1 → S1 through reverse system cross-over (RISC), and then the S1 state exciton radiates to be attenuated to the ground state S0(Nature,2012,492, 234-.
The theoretical maximum internal quantum yield, structural design diversity and material cost of the above materials are shown in table 1:
TABLE 1
Fluorescent material: according to spin statistics, the ratio of singlet to triplet excitons in an exciton is 1:3, so that the maximum internal quantum yield of the fluorescent material does not exceed 25%. According to the lambertian light emitting mode, the light extraction efficiency is about 20%, so the EQE of the OLED device based on the fluorescent material is not more than 5%.
Phosphorescent material: the phosphorescence material can enhance the inter-system cross-over in molecules through the spin coupling effect due to the heavy atom effect, and can directly utilize 75% of triplet excitons, thereby realizing the emission participated in by S1 and T1 together at room temperature, and the theoretical maximum internal quantum yield can reach 100%. According to the lambertian light emitting mode, the light extraction efficiency is about 20%, so the EQE of the OLED device based on the phosphorescent material can reach 20%. However, the phosphorescent material is basically a heavy metal complex such as Ir, Pt, Os, Re, Ru and the like, and the production cost is high, so that the large-scale production is not facilitated. Under high current density, the phosphorescent material has serious efficiency roll-off phenomenon, and the stability of the phosphorescent device is not good.
Triplet-triplet annihilation (TTA) material: two adjacent triplet excitons recombine to produce a higher energy singlet excited state molecule and a ground state molecule, but two triplet excitons produce a singlet exciton, so the theoretical maximum internal quantum yield can only reach 62.5%. In order to prevent the generation of the large efficiency roll-off phenomenon, the concentration of triplet excitons needs to be regulated during this process.
Thermally Activated Delayed Fluorescence (TADF) material: when the energy level difference between the singlet excited state and the triplet excited state is small, reverse intersystem crossing RISC occurs inside the molecule, T1 state excitons are up-converted to S1 state by absorbing environmental heat, 75% of triplet state excitons and 25% of singlet state excitons can be simultaneously utilized, and the theoretical maximum internal quantum yield can reach 100%. Mainly organic compounds, does not need rare metal elements and has low production cost. Chemical modification can be performed by a variety of methods. However, the TADF materials found so far are relatively few, and new TADF materials that can be used in OLED devices are in need of development.
Disclosure of Invention
In view of the above, the present invention provides an organic compound having the following structural formula:
R1、R2、R3、R4each independently selected from hydrogen, substituted or unsubstituted C4-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, substituted or unsubstituted C4-C40 fused aryl, and substituted or unsubstituted C4-C40 fused heteroaryl;
m is R1The value of the number of (1) to (3);
n is R2The value of the number of (1) to (2);
o is R4The value of the number of (1) to (2);
p is R3The value of (a) is 1-3.
The organic compound of the invention is a material with Thermal Activation Delayed Fluorescence (TADF) property, which is used as a host or guest material of a light-emitting layer of an organic electroluminescent device but not limited to the light-emitting layer, and can greatly improve the performance of the device because the material can utilize triplet energy.
The organic compound avoids the aggregation of the compound and the direct accumulation of a conjugated plane to form pi aggregation or excimer by accessing the group with large steric hindrance, thereby improving the luminous efficiency.
The organic compound has TADF (TADF) characteristics, and can emit light by utilizing triplet excitons obtained by traditional fluorescent molecular transition forbidden blocking, so that the efficiency of the device is improved. The fundamental reason is that the designed molecules have large rigid distortion, the overlapping between HOMO and LUMO is reduced, the energy level difference between a triplet state and a singlet state can be reduced to be below 0.25eV, and the reverse crossing of triplet state energy to the singlet state is met, so that the luminous efficiency is improved.
The organic compound has the Bipolar characteristic, and is used as a light emitting layer to greatly improve the transmission capability of two carriers, improve the carrier balance, improve the fluorescence quantum efficiency and reduce the voltage of a device.
The OLED prepared by the organic compound does not contain any heavy metal (Ir, Pt or Au), is low in cost and is more environment-friendly; different from the traditional fluorescent material without heavy metal, the organic compound has TADF (TADF) characteristics, can utilize triplet exciton energy, and has higher efficiency.
Drawings
Fig. 1 is a schematic diagram of a HOMO energy level of a simulated compound M1 by using a gaussian software calculation method according to an embodiment of the present invention.
Fig. 2 is a schematic diagram of the LUMO energy level of a simulated compound M1 using gaussian software calculation.
Fig. 3 is a schematic diagram of simulating the HOMO energy level of compound M2 by using gaussian software calculation.
Fig. 4 is a schematic diagram of the LUMO energy level of a simulated compound M2 using gaussian software calculation.
Fig. 5 is a schematic diagram of simulating the HOMO energy level of compound M3 by using gaussian software calculation means according to an embodiment of the present invention.
Fig. 6 is a schematic diagram of the LUMO energy level of a simulated compound M3 using gaussian software calculation.
Fig. 7 is a schematic diagram of simulating the HOMO energy level of compound M4 by using gaussian software calculation means according to an embodiment of the present invention.
Fig. 8 is a schematic diagram of the LUMO energy level of a simulated compound M4 using gaussian software calculation.
Fig. 9 is a schematic structural diagram of an organic light emitting device provided in an embodiment of the present invention.
Detailed Description
In order to better understand the technical solution of the present application, the following detailed description is made on the embodiments of the present application.
It should be understood that the embodiments described are only a few embodiments of the present application, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
The terminology used in the embodiments of the present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. As used in the examples of this application and the appended claims, the singular forms "a", "an", and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
It should be understood that the term "and/or" as used herein is merely one type of association that describes an associated object, meaning that three relationships may exist, e.g., a and/or B may mean: a exists alone, A and B exist simultaneously, and B exists alone. In addition, the character "/" herein generally indicates that the former and latter related objects are in an "or" relationship.
In the description herein, it is to be understood that the terms "substantially", "approximately", "about", "approximately", "substantially", and the like in the claims and the examples herein are intended to be generally accepted as not being an exact value within a reasonable process operating range or tolerance.
One aspect of the present invention provides an organic compound having the following general structural formula:
R1、R2、R3、R4each independently selected from hydrogen, substituted or unsubstituted C4-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, substituted or unsubstituted C4-C40 fused aryl, and substituted or unsubstituted C4-C40 fused heteroaryl;
m is R1The value of the number of (1) to (3);
n is R2The value of the number of (1) to (2);
o is R4The value of the number of (1) to (2);
p is R3The value of (a) is 1-3.
According to one embodiment of the compounds of the invention, R1、R2、R3、R4The same is true.
According to one embodiment of the compounds of the invention, R1、R3The same is true.
According to one embodiment of the compounds of the invention, R2、R4The same is true.
According to one embodiment of the compounds of the invention, R1、R2、R3Same, or R1、R2、R4Same, or R2、R3、R4The same is true.
According to one embodiment of the compounds of the invention, R1、R2、R3、R4Each independently selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted azophenylcarbazolyl, substituted or unsubstituted trianilino, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylCarbazolyl, substituted or unsubstituted trianilino, substituted or unsubstituted azaanthracenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted quaterphenylyl, substituted or unsubstituted thiophenebiphenylamino, substituted or unsubstituted furanbenzidine, substituted or unsubstituted phenoxyoxazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted phenazinyl
At least one of the group consisting of a group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzanthryl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted picene group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted thianthrenyl group, an acridinyl group and derivatives thereof,
R1、R2、R3、R4not hydrogen at the same time.
According to one embodiment of the compounds of the invention, R1、R2、R3、R4Each independently selected from hydrogen or at least one of the following groups,
wherein, # denotes the attachment position;
R5one selected from hydrogen, halogen, hydroxyl, nitryl, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted amino, C4-C8 naphthenic base, C4-C40 aryl and C4-C40 heteroaryl.
One of the compounds according to the inventionEmbodiment mode, R1、R2、R3、R4Each independently selected from hydrogen or at least one of the following groups,
where, # denotes the ligation position.
According to one embodiment of the compound of the present invention, the organic compound is selected from one of the following compounds:
the invention also provides a display panel, which comprises an organic light-emitting device, wherein the organic light-emitting device comprises an anode and a cathode which are oppositely arranged, and a light-emitting layer positioned between the anode and the cathode, the light-emitting layer comprises a host material and a guest material, and the host material or the guest material of the light-emitting layer is at least one of the organic compounds.
The invention also provides a display panel, which comprises an organic light-emitting device, wherein the organic light-emitting device comprises an anode and a cathode which are oppositely arranged, a substrate layer positioned on one side of the anode, which is far away from the cathode, and an organic film layer positioned between the anode and the cathode, the organic film layer comprises an electron transport layer, a hole transport layer and a light-emitting layer, and at least one of the electron transport layer, the hole transport layer and the light-emitting layer is made of at least one of the organic compounds.
According to an embodiment of the display panel of the present invention, the present invention also provides a display device including any one of the display panels described above.
In the display panel according to the present invention, the anode material of the organic light emitting device 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; examples of the conductive polymer include polyaniline, polypyrrole, and poly (3-methylthiophene). In addition to the above materials and combinations thereof that facilitate hole injection, the anode material may include other known materials suitable for use as an anode.
In the display panel according to the present invention, the cathode material of the organic light emitting device may be selected from metals such as aluminum, magnesium, silver, indium, tin, titanium, etc., and alloys thereof; multilayer metallic materials, e.g. LiF/Al, LiO2/Al、BaF2Al, etc. In addition to the above materials and combinations thereof that facilitate electron injection, the cathode material can include other known materials suitable for use as a cathode.
In an embodiment of the present invention, the organic light emitting device in the display panel may be fabricated by: 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.
The novel compound designed above can be used as a material for at least one of an electron transport layer, a hole transport layer, and a light emitting layer in an organic thin layer, and can be used as a host material or a doping material.
Several exemplary synthetic examples of compounds are provided below.
Example 1
Compound A (11.68g, 20mmol), THF 100ml and magnesium strip 1.2g were added in this order to a 250ml three-necked flask, and the mixture was stirred for 30min under heating with nitrogen substitution. Dissolving a compound dimethyl tin chloride (4.38g, 20mmol) by using 60ml of toluene, slowly dropwise adding the solution into a reaction system, naturally raising the temperature to room temperature after dropwise adding is finished, reacting for 6 hours, adding 60ml of ice water after the reaction is finished, quenching, respectively extracting reaction liquid by using DCM (100ml of x 3) and saturated saline (100ml of x 2), rotatably evaporating an organic phase to obtain an oily substance, and recrystallizing by using TOL/EtOH to obtain a solid B.
The structure confirmation data is as follows: MALDI-TOF: 573.01, respectively;
1H NMR(400MHz,Chloroform)δ7.55(s,2H),7.37(s,2H),7.33(s,2H),7.23(d,J＝10.0Hz,4H),7.15(s,2H),7.08(s,2H),7.00(s,2H),6.51(s,2H),1.64(s,6H).
13C NMR(100MHz,Chloroform)δ146.93(d,J＝1.3Hz),143.49(s),142.10(s),140.04(s),137.14(s),133.55(s),131.15(s),129.53–129.16(m),125.09(s),124.67(s),123.20(s),122.99(s),116.79(s),53.36(s),26.76(s).
a250 ml three-necked flask was charged with the compound B (11.46g, 20mmol), boron tribromide (6.26g, 25mmol) and 100ml of toluene in this order, stirred, purged with nitrogen and heatedThe reaction was refluxed for 24h to 100 ℃ and the end of the reaction was monitored by HPLC. Introduction of Cl2The reaction was continued for 5 h. Cooling to room temperature, drying, passing through a column, and carrying out vacuum distillation on the organic phase to obtain a compound C.
The structure confirmation data is as follows: MALDI-TOF: 514.99.
1H NMR(400MHz,Chloroform)δ7.54(s,2H),7.36(s,2H),7.32(s,2H),7.22(d,J＝10.0Hz,6H),7.07(s,4H),6.99(s,2H).
13C NMR(100MHz,Chloroform)δ184.94(s),150.04(s),146.93(s),146.23(s),143.49(s),142.28(s),133.55(s),132.18(s),129.33(d,J＝15.6Hz),128.77(s),127.82(s),124.67(s),123.20(s),122.99(s).
compound D (6.82g, 20mmol), THF 100ml and magnesium strip 1.2g were added in this order to a 250ml three-necked flask, and the mixture was stirred for 30min under heating with nitrogen substitution. Dissolving a compound dimethyl tin chloride (4.38g, 20mmol) by using 60ml of toluene, slowly dropwise adding the solution into a reaction system, naturally raising the temperature to room temperature after dropwise adding is finished, reacting for 6 hours, adding 60ml of ice water after the reaction is finished, quenching, respectively extracting reaction liquid by using DCM (100ml of x 3) and saturated saline (100ml of x 2), rotatably evaporating an organic phase to obtain an oily substance, and recrystallizing by using TOL/EtOH to obtain a solid E.
The structure confirmation data is as follows: MALDI-TOF: 329.91.
1H NMR(400MHz,Chloroform)δ7.43(s,1H),7.27(s,1H),7.20(s,1H),7.05(s,1H),6.47(s,1H),1.64(s,6H).
13C NMR(100MHz,Chloroform)δ149.00(s),143.09(s),137.23(s),131.14(s),128.95(d,J＝10.4Hz),126.45(s),114.92(s),53.36(s),26.76(s).
a250 ml three-neck flask was charged with the compound E (6.60g, 20mmol), boron tribromide (6.26g, 25mmol) and 100ml of toluene in this order, stirred, purged with nitrogen, and heated to 100 ℃ to refluxThe reaction was run for 24h and the end of the reaction was monitored by HPLC. Introduction of Cl2The reaction was continued for 5 h. Cooling to room temperature, drying, passing through a column, and carrying out vacuum distillation on the organic phase to obtain a compound F.
The structure confirmation data is as follows: MALDI-TOF: 271.88.
1H NMR(400MHz,Chloroform)δ7.53(s,1H),7.27(s,2H),7.20(s,2H).
13C NMR(100MHz,Chloroform)δ184.94(s),148.15(s),144.60(s),130.16(s),128.80(s),127.74(s),127.19(s).
compound C (10.30g, 20mmol) was charged into a reaction flask, dissolved by adding diethyl ether (50mL) and replaced with nitrogen three times. Cooling to-78 deg.C, controlling temperature below-65 deg.C, slowly adding n-BuLi 16.08mL (2.5M, 40mmol), stirring for 30 min. Compound F (5.43g, 20mmol) was dissolved in 60mL of toluene, slowly added dropwise to the reaction mixture, and allowed to spontaneously warm to room temperature after completion of the dropwise addition for 6 hours. After the reaction was complete, the reaction was quenched by the addition of ice water (100 mL). DCM (80mL × 2) was added and extracted, and finally once with brine. The organic phase was collected and rotary evaporated to give a pale yellow oil. The product was purified by column chromatography (mobile phase n-hexane: dichloromethane ═ 3:1) to give compound M1.
The structure confirmation data is as follows: MALDI-TOF: 467.20.
1H NMR(400MHz,Chloroform)δ7.63(s,1H),7.55(s,4H),7.37(s,4H),7.27(d,J＝5.0Hz,6H),7.25(d,J＝10.0Hz,4H),7.08(s,4H),7.00(s,2H).
13C NMR(100MHz,Chloroform)δ174.20(s),162.64(s),159.21(s),146.93(s),144.30(s),143.67(s),143.49(s),139.06(s),138.67(d,J＝19.5Hz),133.55(s),129.75(s),129.33(d,J＝15.6Hz),126.79(s),126.15(s),124.67(s),123.66(s),123.20(s),122.99(s),121.17(s).
fig. 1 is a schematic diagram of a HOMO energy level of a simulated compound M1 by using a gaussian software calculation method according to an embodiment of the present invention. FIG. 2 is a schematic diagram of a system for utilizing gaussi according to an embodiment of the present inventionan software calculation means simulates the LUMO energy level schematic diagram of compound M1, it is evident from FIGS. 1 and 2 that the respective arrangement of HOMO and LUMO in different units results in a relatively complete separation, which helps to reduce the gap energy difference △ ESTThereby improving the anti-backlash crossing capability.
Example 2
Compound 2-1(11.68g, 20mmol), THF 100ml and magnesium strip 1.2g were added in this order to a 250ml three-necked flask, and the mixture was stirred for 30min under heating with nitrogen substitution. Dissolving a compound dimethyl tin chloride (4.38g, 20mmol) by using 60ml of toluene, slowly dropwise adding the solution into a reaction system, naturally raising the temperature to room temperature after dropwise adding is finished, reacting for 6 hours, adding 60ml of ice water after the reaction is finished, quenching, respectively extracting reaction liquid by using DCM (100ml of x 3) and saturated saline (100ml of x 2), rotatably evaporating an organic phase to obtain an oily substance, and recrystallizing by using TOL/EtOH to obtain a solid 3-1.
The structure confirmation data is as follows: MALDI-TOF: 573.01, respectively;
1H NMR(400MHz,Chloroform)δ7.55(s,2H),7.37(s,2H),7.33(s,2H),7.23(d,J＝10.0Hz,4H),7.15(s,2H),7.08(s,2H),7.00(s,2H),6.51(s,2H),1.64(s,6H).
13C NMR(100MHz,Chloroform)δ146.93(d,J＝1.3Hz),143.49(s),142.10(s),140.04(s),137.14(s),133.55(s),131.15(s),129.53–129.16(m),125.09(s),124.67(s),123.20(s),122.99(s),116.79(s),53.36(s),26.76(s).
in a 250ml three-neck flask, compound 3-1(11.46g, 20mmol), boron tribromide (6.26g, 25mmol) and 100ml of toluene are sequentially added, stirring is started, nitrogen gas replacement is carried out, the mixture is heated to 100 ℃ for reflux reaction for 24h, and the reaction end point is monitored by HPLC. Introduction of Cl2The reaction was continued for 5 h. Cooling to room temperature, drying, passing through a column, and carrying out vacuum distillation on the organic phase to obtain a compound 4-1.
The structure confirmation data is as follows: MALDI-TOF: 514.99.
1H NMR(400MHz,Chloroform)δ7.54(s,2H),7.36(s,2H),7.32(s,2H),7.22(d,J＝10.0Hz,6H),7.07(s,4H),6.99(s,2H).
13C NMR(100MHz,Chloroform)δ184.94(s),150.04(s),146.93(s),146.23(s),143.49(s),142.28(s),133.55(s),132.18(s),129.33(d,J＝15.6Hz),128.77(s),127.82(s),124.67(s),123.20(s),122.99(s).
compound 4-1(10.30g, 20mmol) was charged into a reaction flask, dissolved by adding diethyl ether (50mL), and replaced with nitrogen three times. Cooling to-78 deg.C, controlling temperature below-65 deg.C, slowly adding n-BuLi 16.08mL (2.5M, 40mmol), stirring for 30 min. Then 60mL of toluene was added to dissolve the compound 4-1(10.30g, 20mmol), the mixture was slowly added dropwise to the reaction solution, and after the addition was completed, the temperature was naturally raised to room temperature to react for 6 hours. After the reaction was complete, the reaction was quenched by the addition of ice water (100 mL). DCM (80mL × 2) was added and extracted, and finally once with brine. The organic phase was collected and rotary evaporated to give a pale yellow oil. The product was purified by column chromatography (mobile phase n-hexane: dichloromethane ═ 3:1) to give compound M2.
The structure confirmation data is as follows: MALDI-TOF: 710.31.
1H NMR(400MHz,Chloroform)δ7.55(s,4H),7.37(s,4H),7.26(d,J＝16.0Hz,10H),7.08(s,10H),7.00(s,8H)
13C NMR(100MHz,Chloroform)δ174.20(s),162.64(s),146.93(s),144.30(s),143.49(s),138.67(d,J＝15.6Hz),133.55(s),129.33(d,J＝12.5Hz),126.15(s),124.67(s),123.20(s),122.99(s),121.17(s).
fig. 3 is a schematic diagram of simulating the HOMO energy level of compound M2 by using gaussian software calculation. Fig. 4 is a schematic diagram of the LUMO energy level of a simulated compound M2 using gaussian software calculation. As is evident from FIGS. 3 and 4, the HOMO and LUMO of the molecule are arranged differentlyIn the Unit (2), relatively complete separation is realized, which helps to reduce the gap energy difference △ ESTThereby improving the anti-backlash crossing capability.
Example 3
Compound M3-1(11.68g, 20mmol), THF 100ml and magnesium strip 1.2g were sequentially added to a 250ml three-necked flask, and the mixture was stirred for 30min under nitrogen substitution. Dissolving a compound dimethyl tin chloride (4.38g, 20mmol) by using 60ml of toluene, slowly dropwise adding the solution into a reaction system, naturally raising the temperature to room temperature after dropwise adding is finished, reacting for 6 hours, adding 60ml of ice water after the reaction is finished, quenching the reaction, respectively extracting the reaction solution by using DCM (100ml of x 3) and saturated saline (100ml of x 2), rotatably evaporating an organic phase to obtain an oily substance, and recrystallizing by using TOL/EtOH to obtain a solid M3-2.
The structure confirmation data is as follows: MALDI-TOF: 573.01, respectively;
1H NMR(400MHz,Chloroform)δ7.55(s,2H),7.37(s,2H),7.33(s,2H),7.23(d,J＝10.0Hz,4H),7.15(s,2H),7.08(s,2H),7.00(s,2H),6.51(s,2H),1.64(s,6H).
13C NMR(100MHz,Chloroform)δ146.93(d,J＝1.3Hz),143.49(s),142.10(s),140.04(s),137.14(s),133.55(s),131.15(s),129.53–129.16(m),125.09(s),124.67(s),123.20(s),122.99(s),116.79(s),53.36(s),26.76(s).
in a 250ml three-necked flask, compound M3-2(11.46g, 20mmol), boron tribromide (6.26g, 25mmol) and 100ml of toluene were sequentially added, stirring was started, nitrogen substitution was performed, the mixture was heated to 100 ℃ and refluxed for 24 hours, and the end point of the reaction was monitored by HPLC. Introduction of Cl2The reaction was continued for 5 h. Cooling to room temperature, drying, passing through a column, and carrying out vacuum distillation on the organic phase to obtain a compound M3-3.
The structure confirmation data is as follows: MALDI-TOF: 514.99.
1H NMR(400MHz,Chloroform)δ7.54(s,2H),7.36(s,2H),7.32(s,2H),7.22(d,J＝10.0Hz,6H),7.07(s,4H),6.99(s,2H).
13C NMR(100MHz,Chloroform)δ184.94(s),150.04(s),146.93(s),146.23(s),143.49(s),142.28(s),133.55(s),132.18(s),129.33(d,J＝15.6Hz),128.77(s),127.82(s),124.67(s),123.20(s),122.99(s).
compound M3-3(10.30g, 20mmol) was charged into a reaction flask, dissolved in diethyl ether (50mL) and replaced with nitrogen three times. Cooling to-78 deg.C, controlling temperature below-65 deg.C, slowly adding n-BuLi 16.08mL (2.5M, 40mmol), stirring for 30 min. Then, compound M3-4(10.26g, 20mmol) was dissolved in 60mL of toluene, and slowly added dropwise to the reaction mixture, after completion of the dropwise addition, the mixture was naturally warmed to room temperature to react for 6 hours. After the reaction was complete, the reaction was quenched by the addition of ice water (100 mL). DCM (80mL × 2) was added and extracted, and finally once with brine. The organic phase was collected and rotary evaporated to give a pale yellow oil. The product was purified by column chromatography (mobile phase n-hexane: dichloromethane ═ 3:1) to give compound M3.
The structure confirmation data is as follows: MALDI-TOF: 708.29.
1H NMR(400MHz,Chloroform)δ8.55(s,1H),8.19(s,1H),7.82(s,2H),7.73(d,J＝4.0Hz,4H),7.63–7.38(m,6H),7.38–7.31(m,6H),7.31–7.06(m,10H),7.00(s,4H).
13C NMR(100MHz,Chloroform)δ170.42(s),158.10(s),151.17(s),149.92(s),146.93(s),144.41(s),142.90(s),139.31(s),137.94(s),137.69(s),135.38(s),133.42(s),132.46(s),130.97(s),130.74(s),130.20(s),129.67(s),129.27(s),127.76(d,J＝7.2Hz),126.89(s),126.15(s),125.67(s),124.67(s),123.39(s),122.99(s),121.31–121.03(m),117.07(s),114.89(d,J＝13.7Hz).
fig. 5 is a schematic diagram of simulating the HOMO energy level of compound M3 by using gaussian software calculation means according to an embodiment of the present invention. FIG. 6 is a schematic diagram of the LUMO energy level of a simulated compound M3 using Gaussian software calculationAs is evident from FIGS. 5 and 6, the arrangement of the HOMO and LUMO molecules on different units, respectively, achieves a more complete separation, which helps to reduce the gap energy difference △ ESTThereby improving the anti-backlash crossing capability.
Example 4
Compound M4-1(16.31g, 20mmol), THF 100ml and magnesium strip 1.2g were sequentially added to a 250ml three-necked flask, and the mixture was stirred for 30min under nitrogen substitution. Dissolving a compound dimethyl tin chloride (4.38g, 20mmol) by using 60ml of toluene, slowly dropwise adding the solution into a reaction system, naturally raising the temperature to room temperature after dropwise adding is finished, reacting for 6 hours, adding 60ml of ice water after the reaction is finished, quenching the reaction, respectively extracting the reaction solution by using DCM (100ml of x 3) and saturated saline (100ml of x 2), rotatably evaporating an organic phase to obtain an oily substance, and recrystallizing by using TOL/EtOH to obtain a solid M4-2.
The structure confirmation data is as follows: MALDI-TOF: 806.01, respectively;
1H NMR(400MHz,Chloroform)δ7.37(d,J＝1.6Hz,2H),7.34(s,4H),7.50–7.24(m,8H),7.24–7.03(m,18H),7.00(s,3H).
13C NMR(100MHz,Chloroform)δ153.78(s),149.00(s),147.04–146.73(m),142.49(s),140.34(s),139.59(s),136.88(s),135.33(s),134.49(t,J＝12.7Hz),131.20(s),130.20(s),129.32(d,J＝11.3Hz),125.07(s),124.67(s),118.47(s),109.41(s),97.62(s),-6.21(s).
in a 250ml three-neck flask, compound M4-2(16.13g, 20mmol), boron tribromide (6.26g, 25mmol) and 100ml of toluene are sequentially added, stirring is started, nitrogen gas replacement is carried out, the mixture is heated to 100 ℃ and refluxed for 24 hours, and the end point of the reaction is monitored by HPLC. Introduction of Cl2The reaction was continued for 5 h. Cooling to room temperature, drying, passing through a column, and carrying out vacuum distillation on the organic phase to obtain a compound M4-3.
The structure confirmation data is as follows: MALDI-TOF: 748.07.
1H NMR(400MHz,Chloroform)δ7.37(d,J＝1.6Hz,2H),7.34(s,4H),7.50–7.24(m,8H),7.24–7.03(m,12H),7.00(s,3H).
13C NMR(100MHz,Chloroform)δ159.07(s),153.78(s),151.90(s),147.04–146.73(m),142.63(s),140.34(s),138.91(s),135.48(s),133.84(s),132.45(s),131.65(s),130.83(s),130.20(s),129.32(d,J＝11.3Hz),126.98(s),125.07(s),124.67(s),119.46(s),109.41(s),97.62(s).
compound M4-3(14.92g, 20mmol) was added to a reaction flask, dissolved in diethyl ether (50mL) and replaced with nitrogen three times. Cooling to-78 deg.C, controlling temperature below-65 deg.C, slowly adding n-BuLi 16.08mL (2.5M, 40mmol), stirring for 30 min. Then, compound M4-4(12.66g, 20mmol) was dissolved in 60mL of toluene, and slowly added dropwise to the reaction mixture, after completion of the dropwise addition, the mixture was naturally warmed to room temperature to react for 6 hours. After the reaction was complete, the reaction was quenched by the addition of ice water (100 mL). DCM (80mL × 2) was added and extracted, and finally once with brine. The organic phase was collected and rotary evaporated to give a pale yellow oil. The product was purified by column chromatography (mobile phase n-hexane: dichloromethane ═ 3:1) to give compound M4.
The structure confirmation data is as follows: MALDI-TOF: 1059.42.
1H NMR(400MHz,Chloroform)δ8.55(s,1H),8.19(s,1H),7.82(s,2H),7.73(d,J＝4.0Hz,5H),7.54(d,J＝12.0Hz,5H),7.39(d,J＝12.0Hz,4H),7.31–6.80(m,27H),2.31(s,6H).
13C NMR(100MHz,Chloroform)δ223.99(s),165.99(s),158.10(s),153.78(s),147.14–146.69(m),143.57(s),140.95(s),140.34(s),139.31(s),139.06(s),137.69(s),137.40(d,J＝10.5Hz),135.48(d,J＝19.9Hz),135.02(s),134.27(s),132.99(s),132.27(s),131.05(s),130.50(s),130.20(d,J＝0.8Hz),129.38(s),129.08(s),127.72(s),127.16(s),125.93–125.54(m),123.59(d,J＝16.4Hz),122.41(s),121.15(d,J＝2.7Hz),120.90(s),120.58(s),119.00(s),116.41(s),114.89(d,J＝13.7Hz),109.41(s),108.52(s),97.62(s),21.83(s).
FIG. 7 is a schematic diagram of the HOMO level of a simulated compound M4 using Gaussian software computing means according to the present invention, FIG. 8 is a schematic diagram of the LUMO level of a simulated compound M4 using Gaussian software computing means according to the present invention, it is evident from FIGS. 7 and 8 that the HOMO and LUMO of the molecule are respectively arranged on different units to achieve relatively complete separation, which helps to reduce the gap energy difference △ ESTThereby improving the anti-backlash crossing capability.
As is obvious from FIGS. 1-8, the HOMO and LUMO of the molecule are respectively arranged on different units, so that relatively complete segregation is realized, which is helpful for reducing the gap energy difference △ ESTThereby improving the anti-backlash crossing capability.
Table 1 energy level diagram of the compounds
As can be seen from table 1 above, the organic compound provided by the present invention has TADF characteristics, and can emit light by using triplet excitons that are forbidden by conventional fluorescent molecular transition, thereby improving device efficiency, and the compound provided by the present invention has large rigid twist, reduces overlap between HOMO and LUMO, and can reduce the energy level difference between triplet and singlet states to less than 0.25eV, thereby satisfying reverse transition of triplet energy to singlet energy and improving light emission efficiency.
The organic compound is applied to an organic light-emitting device:
the present embodiment provides an organic light emitting device having a structure as shown in fig. 9, the organic light emitting device including: the light-emitting diode comprises a substrate 1, an anode 2(ITO), a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light-emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, an electron injection layer 9 and a cathode 10 (aluminum electrode), wherein an upward arrow in FIG. 9 represents a light-emitting direction, wherein the thickness of the ITO anode 2 is 10nm, the thickness of the hole injection layer 3 is 5nm, the thickness of the first hole transport layer 4 is 50nm, the thickness of the second hole transport layer 5 is 10nm, the thickness of the light-emitting layer 6 is 30nm, the thickness of the first electron transport layer 7 is 5nm, the thickness of the second electron transport layer 8 is 20nm, the thickness of the electron injection layer 9 is 1nm, and the thickness of the aluminum electrode 10 is 15 nm.
Several application examples of the organic compound of the present invention to an organic light emitting device are provided below.
Application example 1
The organic light emitting device 01 was prepared as follows: :
1) the glass substrate 1 was cut into a size of 50mm × 50mm × 0.7mm, sonicated in isopropanol and deionized water for 30 minutes, respectively, and then exposed to ozone for about 10 minutes to clean; mounting the resulting glass substrate with the ITO anode 2 on a vacuum deposition apparatus;
2) under vacuum degree of 2X 10-6Evaporating a hole injection layer material HAT-CN on the ITO anode layer 2 in a vacuum evaporation mode under Pa, wherein the thickness of the hole injection layer material HAT-CN is 5nm, and the layer is used as a hole injection layer 3;
3) vacuum-evaporating a material of the first hole transport layer 4, which is N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (α -NPD) having a thickness of 50nm, on the hole injection layer 3 as a first hole transport layer 4;
4) vacuum evaporating a material of the second hole transport layer 5, namely 1, 3-dicarbazole-9-yl benzene (mCP), with the thickness of 10nm, on the first hole transport layer 4 to form the second hole transport layer 5;
5) a light-emitting layer 6 is co-deposited on the second hole transport layer 5, wherein the compound M1 is used as a host material of the light-emitting layer, Ir (ppy)3 is used as a doping material, the doping proportion is 8% (mass ratio), and the thickness is 30 nm;
6) a first electron transport layer 7 is vacuum-evaporated on the luminescent layer 6, the material of the first electron transport layer 7 is diphenyl [4- (triphenylsilyl) phenyl ] phosphine oxide (TSPO1), and the thickness is 5 nm;
7) a second electron transport layer 8 is vacuum-evaporated on the first electron transport layer 7, the material of the second electron transport layer 8 is TPBi, and the thickness is 20 nm;
8) an electron injection layer 9 is vacuum evaporated on the second electron transport layer 8, the material of the electron injection layer 9 is LiF, and the thickness is 1 nm;
9) an aluminum electrode was vacuum-deposited on the electron injection layer 9 to a thickness of 15nm to form a cathode 10.
Application example 2
The organic light-emitting device 02 was produced in the same manner as in application example 1, except that the compound M1 was replaced with the compound M2, as in application example 1.
Application example 3
The organic light-emitting device 03 was produced in the same manner as in application example 1, except that the compound M1 was replaced with the compound M3, as in application example 1.
Application example 4
The organic light-emitting device 04 was produced in the same manner as in application example 1, except that the compound M1 was replaced with the compound M4, as in application example 1.
Application comparative example 1
The organic light emitting device 05 was fabricated in the same manner as in application example 1, except that compound M1 was replaced with DCJTB, as compared with application example 1.
TABLE 2
As can be seen from table 2 above, the organic light emitting device prepared from the organic compound of the present application has high external quantum efficiency, and the OLED device prepared from the organic compound has high current efficiency and light emitting efficiency.
Still another aspect of the present invention also provides a 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.
The above description is only exemplary of the present application and should not be taken as limiting the present application, as any modification, equivalent replacement, or improvement made within the spirit and principle of the present application should be included in the scope of protection of the present application.
Claims (12)
1. An organic compound having the general structural formula:
R1、R2、R3、R4each independently selected from hydrogen, substituted or unsubstituted C4-C40 aryl, substituted or unsubstituted C4-C40 heteroaryl, substituted or unsubstituted C4-C40 fused aryl, and substituted or unsubstituted C4-C40 fused heteroaryl;
m is R1The value of the number of (1) to (3);
n is R2The value of the number of (1) to (2);
o is R4The value of the number of (1) to (2);
p is R3The value of (a) is 1-3.
2. An organic compound according to claim 1, wherein R is1、R2、R3、R4The same is true.
3. An organic compound according to claim 1, wherein R is1、R3The same is true.
4. An organic compound according to claim 1, wherein R is2、R4The same is true.
5. An organic compound according to claim 1, wherein R is1、R2、R3Same, or R1、R2、R4Same, or R2、R3、R4The same is true.
6. An organic compound according to claim 1, wherein R is1、R2、R3、R4Each independently selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted azacarbazolyl, substituted or unsubstituted trianilino, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylcarbazolyl, substituted or unsubstituted trianilino, substituted or unsubstituted azaanthracenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted tetrabiphenyl, substituted or unsubstituted thiophenebiphenylamino, substituted or unsubstituted furanbenzidine, substituted or unsubstituted phenoxyoxazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, and substituted or unsubstituted phenothiazinyl, Substituted or unsubstituted phenanthryl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted
Substituted or unsubstituted benzophenanthryl, substituted or unsubstituted benzanthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted picene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted thianthryl, acridinyl and derivatives thereofAt least one of the substance groups is selected from,
R1、R2、R3、R4not hydrogen at the same time.
7. An organic compound according to claim 1, wherein R is1、R2、R3、R4Each independently selected from hydrogen or at least one of the following groups,
wherein, # denotes the attachment position;
R5one selected from hydrogen, halogen, hydroxyl, nitryl, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted amino, C4-C8 naphthenic base, C4-C40 aryl and C4-C40 heteroaryl.
8. An organic compound according to claim 1, wherein R is1、R2、R3、R4Each independently selected from hydrogen or at least one of the following groups,
where, # denotes the ligation position.
9. The organic compound according to claim 1, wherein the organic compound is selected from one of the following compounds:
10. a display panel comprising an organic light emitting device comprising an anode, a cathode, and a light emitting layer between the anode and the cathode, the light emitting layer comprising a host material and a guest material, wherein the host material or the guest material of the light emitting layer is at least one of the organic compounds according to any one of claims 1 to 9.
11. A display panel comprising an organic light emitting device, wherein the organic light emitting device comprises an anode, a cathode, a substrate layer on a side of the anode facing away from the cathode, and an organic film layer between the anode and the cathode, the organic film layer comprises an electron transport layer, a hole transport layer, and a light emitting layer, and at least one of the electron transport layer, the hole transport layer, and the light emitting layer is made of the organic compound according to any one of claims 1 to 9.
12. A display device comprising the display panel of claim 10 or 11.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911399670.4A CN111039969B (en) | 2019-12-30 | 2019-12-30 | Organic compound, display panel and display device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911399670.4A CN111039969B (en) | 2019-12-30 | 2019-12-30 | Organic compound, display panel and display device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111039969A true CN111039969A (en) | 2020-04-21 |
| CN111039969B CN111039969B (en) | 2022-04-19 |
Family
ID=70241191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911399670.4A Active CN111039969B (en) | 2019-12-30 | 2019-12-30 | Organic compound, display panel and display device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111039969B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111518123A (en) * | 2020-05-29 | 2020-08-11 | 武汉天马微电子有限公司 | Compound, thermally activated delayed fluorescence material and application thereof |
| WO2022079068A1 (en) * | 2020-10-16 | 2022-04-21 | Merck Patent Gmbh | Heterocyclic compounds for organic electroluminescent devices |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107417715A (en) * | 2017-07-14 | 2017-12-01 | 瑞声科技（南京）有限公司 | A kind of electroluminescent organic material and its luminescent device |
| CN110003258A (en) * | 2019-04-30 | 2019-07-12 | 上海天马有机发光显示技术有限公司 | Compound, display panel and display device |
| US20190341557A1 (en) * | 2018-05-06 | 2019-11-07 | Universal Display Corporation | Host materials for electroluminescent devices |
| WO2019218971A1 (en) * | 2018-05-14 | 2019-11-21 | 江苏三月光电科技有限公司 | Organic electroluminescent component with exciplex serving as main body material |
-
2019
- 2019-12-30 CN CN201911399670.4A patent/CN111039969B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107417715A (en) * | 2017-07-14 | 2017-12-01 | 瑞声科技（南京）有限公司 | A kind of electroluminescent organic material and its luminescent device |
| US20190341557A1 (en) * | 2018-05-06 | 2019-11-07 | Universal Display Corporation | Host materials for electroluminescent devices |
| WO2019218971A1 (en) * | 2018-05-14 | 2019-11-21 | 江苏三月光电科技有限公司 | Organic electroluminescent component with exciplex serving as main body material |
| CN110003258A (en) * | 2019-04-30 | 2019-07-12 | 上海天马有机发光显示技术有限公司 | Compound, display panel and display device |
Non-Patent Citations (1)
| Title |
|---|
| TANJA KAEHLER ET AL.: "Introducing Perylene as a New Member to Azaborine Family", 《ANGEW CHEMIE INTERNATIONAL EDITION》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111518123A (en) * | 2020-05-29 | 2020-08-11 | 武汉天马微电子有限公司 | Compound, thermally activated delayed fluorescence material and application thereof |
| CN111518123B (en) * | 2020-05-29 | 2022-10-25 | 武汉天马微电子有限公司 | Compound, thermally activated delayed fluorescence material and application thereof |
| WO2022079068A1 (en) * | 2020-10-16 | 2022-04-21 | Merck Patent Gmbh | Heterocyclic compounds for organic electroluminescent devices |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111039969B (en) | 2022-04-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102584939B1 (en) | Metal complex with fluorine substitution | |
| EP2215183B1 (en) | New compound and organic light emitting device using the same | |
| KR101787850B1 (en) | Benzo-fused thiophene or benzo-fused furan compounds comprising a triphenylene group | |
| CN110003260B (en) | Boron heterocyclic compound, display panel, and display device | |
| CN111635415B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN109134519B (en) | Boron heterocyclic compound and organic light-emitting display device | |
| CN112125873B (en) | Compound, hole transport material, organic electroluminescent device and display device | |
| CN111662312B (en) | Compound, thermal activation delay fluorescent material and application thereof | |
| CN111039969B (en) | Organic compound, display panel and display device | |
| CN110256473B (en) | Compound, organic photoelectric device and electronic equipment | |
| CN109503576B (en) | Organic compound, display panel, and display device | |
| CN112125813B (en) | Compound, hole transport material and organic electroluminescent device | |
| CN112125892B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN110204565B (en) | Boron-containing compound, display panel and display device | |
| CN110759936B (en) | Compound, display panel and display device | |
| CN113061146A (en) | Organic compound and electroluminescent application thereof | |
| CN111018898B (en) | Compound, display panel and display device | |
| CN111303187A (en) | Organic light-emitting material and organic electroluminescent device | |
| CN111039971B (en) | Boron-containing compound, display panel and display device | |
| CN113321649B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN111423436B (en) | Organic compound and application thereof | |
| CN117143030A (en) | Naphthyl substituted electricity-absorbing fragment compound, electron transport material and application | |
| CN115991699A (en) | Naphthalene bridging double-suction fragment compound | |
| CN113045553A (en) | Aza-aromatic compound used as electron transport material and application thereof | |
| CN111763223A (en) | Organic compound, thermal activation delayed fluorescent material and application thereof |
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 |