CN111116488A - Organic compound, display panel and display device - Google Patents

Organic compound, display panel and display device Download PDF

Info

Publication number
CN111116488A
CN111116488A CN201911377317.6A CN201911377317A CN111116488A CN 111116488 A CN111116488 A CN 111116488A CN 201911377317 A CN201911377317 A CN 201911377317A CN 111116488 A CN111116488 A CN 111116488A
Authority
CN
China
Prior art keywords
group
substituted
unsubstituted
independently selected
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201911377317.6A
Other languages
Chinese (zh)
Other versions
CN111116488B (en
Inventor
代文朋
高威
牛晶华
张磊
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wuhan Tianma Microelectronics Co Ltd
Original Assignee
Wuhan Tianma Microelectronics Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wuhan Tianma Microelectronics Co Ltd filed Critical Wuhan Tianma Microelectronics Co Ltd
Priority to CN201911377317.6A priority Critical patent/CN111116488B/en
Publication of CN111116488A publication Critical patent/CN111116488A/en
Application granted granted Critical
Publication of CN111116488B publication Critical patent/CN111116488B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • H10K50/00—Organic light-emitting devices
    • 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
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • C09K2211/1018—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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The application discloses an organic compound, the structure is as follows:
Figure DDA0002341327980000011
the definition of each substituent is shown in the specification.

Description

Organic compound, display panel and display device
Technical Field
The present disclosure relates to organic electroluminescent materials, and particularly to an organic compound, a display panel and a display device.
Background
OLEDs have advanced significantly over decades. Although the internal quantum efficiency is close to 100%, the external quantum efficiency is only about 20%. Most of the light is confined inside the light emitting device due to factors such as substrate mode loss, surface plasmon loss, and waveguide effect, resulting in a large amount of energy loss.
In the existing OLED display panel, an organic Coating (CPL) is vapor-deposited on a semitransparent metal electrode Al to adjust an optical interference distance, suppress external light reflection, and suppress extinction caused by movement of surface plasma, thereby improving light extraction efficiency and light emission efficiency.
The performance requirements of the OLED on CPL materials are high: no absorption in the visible wavelength region (400 nm-700 nm) as far as possible; high refractive index, low extinction coefficient in the wavelength range of 400nm to 600 nm; high glass transition temperature and molecular thermal stability (high glass transition temperature, vapor deposition capability and no thermal decomposition).
The prior art of CPL materials has the following problems: 1. the refractive index is generally below 1.9, and cannot meet the requirement of high refractive index; 2. under the condition that the refractive index meets the requirement, the visible light region has stronger absorption or larger extinction coefficient; 3. the existing material can not solve the problems of luminous efficiency and chromaticity at the same time, in particular to a blue light emitting element. 4. Tight packing between molecules cannot be achieved, and the coating tightness is poor due to too many pores of the molecular gel during evaporation. 5. The electronic type covering layer material is simply adopted, the effects of electronic transmission and light extraction are achieved, the preparation cost of the device is saved to a certain extent, the light extraction is not facilitated, the luminous efficiency is only weakly improved, and the chromaticity is not solved.
Disclosure of Invention
In view of the above, the present invention provides an organic compound, which has the following structural formula:
Figure BDA0002341327960000021
X1、X2each independently selected from N atom or C-Ra, wherein, X1、X2At least one is an N atom;
ra is hydrogen, deuterium, halogen, nitro, nitrile, thioalkyl, a substituted or unsubstituted Cl to C20 alkyl group, a substituted or unsubstituted Cl to C20 alkoxy or thioalkyl group, a substituted or unsubstituted C3 to C20 cyclic alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C2 to C30 alkenyl or alkynyl group, -N (R is R1)2、-COR1、
Figure BDA0002341327960000022
Ra are independently present or are adjacent groups linked to each other to provide a substituted or unsubstituted aliphatic monocyclic or polycyclic ring, a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted heteroaromatic monocyclic or polycyclic ring;
r1 is a straight chain alkyl, alkoxy or thioalkyl group having 1 to 20C atoms or a cyclic alkyl, alkenyl or alkynyl group having 3 to 20C atoms;
Ar1、Ar2each independently selected from a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof;
l is independently selected from any one of a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group;
and m is the number of L and is an integer of 1-3.
The organic compound can improve the light extraction efficiency and the luminous efficiency (especially for blue pixels with low luminous efficiency) of the top-emitting organic photoelectric device, relieve the luminous angle dependence of an OLED device (most effective for red/green pixels), simultaneously effectively block water and oxygen in the external environment and protect an OLED display panel from being corroded by the water and the oxygen.
The organic compound can be used as a CPL capping layer and has higher refractive index; the EQE of the organic photoelectric device can be effectively improved; the preparation method of the organic compound is simple, and is more beneficial to saving the preparation cost and reducing the cost of the display panel.
In the organic compound, the conjugated condensed ring fluoranthene and the nitrogen-containing heterocycle are matched with each other, the rigid structure of fluoranthene molecules reduces free rotation vibration in the molecules, so that the molecules have regular molecular orientation and are beneficial to light emitting, but the number of fluoranthene molecules cannot be too large, too many bodies are too large, the refractive index can be reduced, and the light emitting efficiency of a device is influenced, so that the number of fluoranthene molecules is the most excellent choice when one molecule is used; compared with common aromatic rings, the nitrogen-containing heterocyclic ring can improve the polarizability of molecules, increase the refractive index of the whole molecules and improve the light extraction efficiency.
Drawings
Fig. 1 is a schematic structural diagram of an organic optoelectronic device according to 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:
Figure BDA0002341327960000031
X1、X2each independently selected from N atom or C-Ra, wherein, X1、X2At least one is an N atom;
ra is hydrogen, deuterium, halogen, nitro, nitrile, thioalkyl, a substituted or unsubstituted Cl to C20 alkyl group, a substituted or unsubstituted Cl to C20 alkoxy or thioalkyl group, a substituted or unsubstituted C3 to C20 cyclic alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C2 to C30 alkenyl or alkynyl group, -N (R is R1)2、-COR1、
Figure BDA0002341327960000041
Ra are independently present or are adjacent groups linked to each other to provide a substituted or unsubstituted aliphatic monocyclic or polycyclic ring, a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted heteroaromatic monocyclic or polycyclic ring;
r1 is a straight chain alkyl, alkoxy or thioalkyl group having 1 to 20C atoms or a cyclic alkyl, alkenyl or alkynyl group having 3 to 20C atoms;
Ar1、Ar2each independently selected from substituted or unsubstituted C6 to C30 arylA group, a substituted or unsubstituted C2 to C30 heterocyclic group, or combinations thereof;
l is independently selected from any one of a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group;
and m is the number of L and is an integer of 1-3.
According to one embodiment of the compound of the present invention, in the organic compound:
X1、X2each independently selected from N or C-Ra, wherein, X1、X2At least one is an N atom; ra is any one of hydrogen, deuterium, halogen, nitro, nitrile group, Cl-C20 alkyl group, C6-C30 aryl group and C2-C30 heterocyclic group;
Ar1、Ar2each independently selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted indolocarbafuranyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted indolocarbaphthenyl group, a substituted or unsubstituted benzofuranyl pyrimidinyl group, Any one of substituted or unsubstituted benzothiophene pyrimidinyl group, substituted or unsubstituted anthracenyl group, and substituted or unsubstituted pyrenyl group;
l is independently selected from any one of a single bond, a C6-C30 arylene group, a C2-C30 heteroarylene group;
and m is the number of L and is an integer of 1-3.
According to the Lorentz-Lorenz equation, the refractive index is proportional to the polarizability and inversely proportional to the molecular volume. The greater the polarizability, the greater the refractive index of the material; the smaller the molecular volume, the larger the refractive index of the material.
When the compound comprises a substituted or unsubstituted heteroaromatic ring group, the heteroaromatic ring is favorable for improving the polarizability of the compound, and pyridine, pyrimidine, quinoline, phenanthroline and the like, so that the refractive index of the material can be improved; meanwhile, the horizontal dipole orientation of the compound structure is beneficial to the stacking arrangement of molecules, the refractive index of the compound can be improved, and the compound is suitable for improving the light extraction effect of a display panel.
According to one embodiment of the compound of the present invention, in the organic compound:
X1、X2each independently selected from N atom or CRa, X1、X2At least one is an N atom; ra is H, D, F, C1, Br, I, CN, NO2Any one of the above;
Ar1、Ar2each independently selected from:
Figure BDA0002341327960000051
Figure BDA0002341327960000061
l is selected from a single bond,
Figure BDA0002341327960000062
Any one of the above;
# denotes the ligation site;
and m is the number of L and is an integer of 1-3.
According to one embodiment of the compound of the present invention, in the organic compound:
X1、X2each independently selected from N or CRa, X1、X2At least one is N; ra is H;
Ar1、Ar2each independently selected from:
Figure BDA0002341327960000063
Figure BDA0002341327960000071
l is independently selected from a single bond,
Figure BDA0002341327960000072
Any one of the above;
# denotes the ligation site;
and m is the number of L and is an integer of 1-3.
According to one embodiment of the compound of the present invention, in the organic compound:
X1、X2each independently selected from N or C-Ra, X1、X2At least one is N; ra is H;
Ar1、Ar2each independently selected from:
Figure BDA0002341327960000081
l is selected from a single bond,
Figure BDA0002341327960000082
One of (1);
# denotes the ligation site;
m is the number of L and takes the value of 1.
According to one embodiment of the compound of the present invention, the organic compound is one of the following structures:
Figure BDA0002341327960000091
Figure BDA0002341327960000101
Figure BDA0002341327960000111
Figure BDA0002341327960000121
Figure BDA0002341327960000131
the present invention also provides a display panel comprising an organic light emitting device comprising an anode, a cathode, at least one organic thin film layer disposed between the anode and the cathode, wherein the organic compound of the organic thin film layer comprises at least one of the compounds.
According to the display panel of the present invention, the organic thin film layer further includes an electron transport layer or a hole transport layer, and at least one of the compounds is contained in the electron transport layer or the hole transport layer.
According to the display panel, the organic thin film layer further comprises a cap layer CPL, and the cap layer CPL comprises at least one of the compounds. The compound has higher optical refractive index, is applied to the cap layer of the display panel, and can improve the light-emitting efficiency of the display panel; meanwhile, the molecular structure of the compound provided by the application is good in stability during evaporation, and the formed film is tightly covered, so that the compound is more suitable for being applied to a display panel.
According to an embodiment of the display panel, the invention further provides a display device comprising the display panel.
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 the display panel of the present invention, the organic thin film layer has at least one light emitting layer (EML), and may further include other functional layers, including a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL).
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. Finally, an organic optical cover layer CPL (cap layer) is prepared on the cathode. The material of the optical coating CPL is a compound according to the present invention. The optical coating CPL can be produced by evaporation or solution processing. Solution processing methods include ink jet printing, spin coating, doctor blade coating, screen printing, roll-to-roll printing, and the like.
Several exemplary synthetic examples of compounds are provided below.
Example 1
Figure BDA0002341327960000141
Figure BDA0002341327960000151
(1) In a 250ml round bottom flask, compound 1-1(15mmol), diethyl malonate (35mmol) and sodium ethoxide (15mmol) were added to dry ethanol (100ml), reacted at 78 ℃ for 12 hours under nitrogen atmosphere, the resulting intermediate mixed solution was added to water, and then filtered through a celite pad, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give intermediate compound 1-2.
(2) In a 250mL round-bottom flask, compound 1-2(15mmol), diethylphenylamine (15mol) were added to dry POCl3(100ml), reacted at 120 ℃ for 6.0 hours under nitrogen atmosphere, and the resulting intermediate mixed solution was added to water, followed by filtration through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, filtered, and evaporated, and the crude product was purified by silica gel column chromatography to give intermediate compounds 1 to 3.
(3) In a 250ml round-bottom flask, compound 1-3(10mmol), compound 1-4(20mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (30 ml)/ethanol (20ml) and aqueous potassium carbonate (12mmol) (10ml) and the reaction was refluxed for 12h under nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain the final product, compound P1.
1H NMR(400MHz,CDCl3)δ8.99-7.95(m,18H)，7.93(s,2H)，7.28(s,1H),7.87-7.55(m,2H),7.23-7.00(m,3H).
And (3) characterization results: elemental analysis result of Compound P1 (formula C)42H26N2): theoretical value: c,90.29H, 4.69; and N, 5.01. Test values are: c, 90.32; h, 4.66; and N, 5.02. ESI-MS (M/z) (M) by LC-MS combined analysis+): the theoretical value is 558.21 and the test value is 558.20.
Example 2
Figure BDA0002341327960000161
(1) In a 250ml round bottom flask, compound 13-1(15mmol), diethyl malonate (35mmol) and sodium ethoxide (15mmol) were added to dry ethanol (100ml), reacted at 78 ℃ for 12 hours under nitrogen atmosphere, the resulting intermediate mixed solution was added to water, and then filtered through a celite pad, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give intermediate compound 13-2.
(2) In a 250mL round-bottom flask, compound 13-2(15mmol), diethylphenylamine (15mol) were added to dry POCl3(100ml), reacted at 120 ℃ for 6.0 hours under nitrogen atmosphere, and the resulting intermediate mixed solution was added to water, followed by filtration through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, filtered, and evaporated, and the crude product was purified by silica gel column chromatography to give intermediate compound 13-3.
(3) Compound 13-3(15mmol) and potassium acetate (40mmol), 2-azuleneboronic acid pinacol ester (15mmol) with dry 1, 4-dioxane (60ml), Pd (dppf) Cl in a 250ml round bottom flask2(0.4mmol) were mixed and stirred at 90 ℃ for 48 hours under nitrogen, the resulting intermediate was cooled to room temperature, added to water, then filtered through a celite pad, the filtrate was extracted with dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by silica gel column chromatography to give intermediate compound 13-4.
(4) In a 250ml round-bottom flask, compound 13-4(20mmol), compound 13-5(10mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (30 ml)/ethanol (20ml) and aqueous potassium carbonate (12mmol) (10ml) and the reaction was refluxed for 12h under nitrogen atmosphere. Cooling the resulting mixture to room temperature, adding water, filtering through a pad of celite, extracting the filtrate with dichloromethane, washing with water, drying over anhydrous magnesium sulfate, filtering and evaporating, and purifying the crude product by silica gel column chromatographyThis gave the final product, compound P13.
1H NMR(400MHz,CDCl3)δ8.93-7.96(m,18H)，7.93(s,2H)，7.54(d,J＝8.4Hz,4H)，7.28(s,1H),7.77-7.55(m,2H),7.23-7.00(m,3H).
And (3) characterization results: elemental analysis result of Compound P13 (formula C)48H30N2): theoretical value: c, 90.85; h, 4.73; n, 4.42. Test values are: c, 90.85; h, 4.73; n, 4.42. ESI-MS (M/z) (M) by LC-MS combined analysis+): the theoretical value is 634.24 and the test value is 634.25.
Example 3
Figure BDA0002341327960000171
(1) In a 250ml round-bottom flask, compound 14-5(20mmol), compound 14-4(10mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (30 ml)/ethanol (20ml) and aqueous potassium carbonate (12mmol) (10ml) and the reaction was refluxed for 12h under nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain the final product, compound P14.
1H NMR(400MHz,CDCl3)δ8.50-8.31(m,2H)，8.20(s,2H)，7.91-7.39(m,18H),7.54(d,J＝8.4Hz,4H)，7.28(s,1H),7.23-7.00(m,3H)；
And (3) characterization results: elemental analysis result of Compound P14 (formula C)48H30N2): theoretical value: c, 90.85; h, 4.73; n, 4.42. Test values are: c, 90.85; h, 4.73; n, 4.42. ESI-MS (M/z) (M) by LC-MS combined analysis+): the theoretical value is 634.24 and the test value is 634.25.
Example 4
Figure BDA0002341327960000181
(1) In a 250ml round bottom flask, compound 47-1(15mmol), diethyl malonate (35mmol) and sodium ethoxide (15mmol) were added to dry ethanol (100ml), reacted at 78 ℃ for 12 hours under a nitrogen atmosphere, the resulting intermediate mixed solution was added to water, and then filtered through a celite pad, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give intermediate compound 47-2.
(2) In a 250mL round-bottom flask, compound 47-2(15mmol), diethylphenylamine (15mol) were added to dry POCl3(100ml), reacted at 120 ℃ for 6.0 hours under nitrogen atmosphere, and the resulting intermediate mixed solution was added to water, followed by filtration through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, filtered, and evaporated, and the crude product was purified by silica gel column chromatography to give intermediate compound 47-3.
(3) In a 250ml round-bottom flask, compound 47-4(20mmol), compound 47-3(10mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (30 ml)/ethanol (20ml) and aqueous potassium carbonate (12mmol) (10ml) and the reaction was refluxed for 12h under nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain the final product, compound P47.
1H NMR(400MHz,CDCl3)δ8.50-8.35(m,3H)，8.31(s,4H)，7.91-7.39(m,14H),7.64(s,1H),7.23-7.00(m,4H)；
And (3) characterization results: elemental analysis result of Compound P47 (formula C)42H26N2): theoretical value: c, 90.32; h, 4.66; and N, 5.02. Test values are: c, 90.32; h, 4.66; and N, 5.02. ESI-MS (M/z) (M) by LC-MS combined analysis+): the theoretical value is 558.21 and the test value is 558.20.
Example 5
Figure BDA0002341327960000191
(1) In a 250ml round bottom flask, compound 75-1(15mmol), diethyl malonate (35mmol) and sodium ethoxide (15mmol) were added to dry ethanol (100ml), reacted at 78 ℃ for 12 hours under nitrogen atmosphere, the resulting intermediate mixed solution was added to water, and then filtered through a celite pad, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give intermediate compound 75-2.
(2) In a 250mL round-bottom flask, compound 75-2(15mmol), diethylphenylamine (15mol) were added to dry POCl3(100ml), reacted at 120 ℃ for 6.0 hours under nitrogen atmosphere, and the resulting intermediate mixed solution was added to water, followed by filtration through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, filtered, and evaporated, and the crude product was purified by silica gel column chromatography to give intermediate compound 75-3.
(3) Compound 75-3(15mmol) and potassium acetate (40mmol), 6-azulene boronic acid pinacol ester (15mmol) with dried 1, 4-dioxane (60ml), Pd (dppf) Cl in a 250ml round bottom flask2(0.4mmol) were mixed and stirred at 90 ℃ under nitrogen for 48 hours, the resulting intermediate was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated, and the crude product was purified by silica gel column chromatography to give the intermediate compound 75-4.
(4) In a 250ml round-bottom flask, compound 75-4(10mmol), compound 75-5(20mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (30 ml)/ethanol (20ml) and aqueous potassium carbonate (12mmol) (10ml) and the reaction was refluxed for 12h under nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, then filtered through a pad of celite, the filtrate was extracted with dichloromethane, then washed with water, and anhydrous sulfuric acid was usedAfter drying, filtration and evaporation of the magnesium, the crude product was purified by silica gel column chromatography to give the final product, compound P75.
1H NMR(400MHz,CDCl3)δ8.82-7.96(m,17H)，7.93(s,2H)，7.54(d,J＝8.4Hz,4H)，7.28(s,1H),7.77-7.55(m,2H),7.23-7.00(m,4H).
And (3) characterization results: elemental analysis result of Compound P75 (formula C)48H30N2): theoretical value: c, 90.85; h, 4.73; n, 4.42. Test values are: c, 90.85; h, 4.73; n, 4.42. ESI-MS (M/z) (M) by LC-MS combined analysis+): the theoretical value is 634.24 and the test value is 634.25.
Example 6
Figure BDA0002341327960000201
(1) In a 250ml round bottom flask, compound 90-1(15mmol), diethyl malonate (35mmol) and sodium ethoxide (15mmol) were added to dry ethanol (100ml), reacted at 78 ℃ for 12 hours under nitrogen atmosphere, the resulting intermediate mixed solution was added to water, and then filtered through a celite pad, the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to give intermediate compound 90-2.
(2) In a 250mL round-bottom flask, compound 90-2(15mmol), diethylphenylamine (15mol) were added to dry POCl3(100ml), reacted at 120 ℃ for 6.0 hours under nitrogen atmosphere, and the resulting intermediate mixed solution was added to water, followed by filtration through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, dried over anhydrous magnesium sulfate, filtered, and evaporated, and the crude product was purified by silica gel column chromatography to give intermediate compound 90-3.
(3) In a 250ml round-bottom flask, compound 90-3(15mmol) and potassium acetate (40mmol), compound 90-4 (2-pyreneboronic acid pinacol ester) (15mmol) were mixed with dried 1, 4-dioxane (60ml), Pd (dppf) Cl2(0.4mmol) and mixing at 90 deg.C under nitrogenStirring under air atmosphere for 48 hours, cooling the resulting intermediate to room temperature, adding water, filtering through a pad of celite, extracting the filtrate with dichloromethane, washing with water, drying over anhydrous magnesium sulfate, filtering and evaporating, and purifying the crude product by silica gel column chromatography to give the intermediate compound 90-5.
(4) In a 250ml round-bottom flask, compound 90-5(10mmol), pinacol 2-naphthoate (10mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (30 ml)/ethanol (20ml) and aqueous potassium carbonate (12mmol) (10ml) and the reaction was refluxed for 12h under nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, and after filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain the final product, compound P90.
1H NMR(400MHz,CDCl3)δ8.59-8.21(m,2H)，7.89(s,1H)，7.78(s,1H),7.77-7.45(m,10H),7.44(s,1H),7.23-7.13(m,3H),7.12-6.23(m,8H)；
And (3) characterization results: elemental analysis result of Compound P90 (formula C)40H26N2): theoretical value: c, 89.89; h, 4.87; and N, 5.24. Test values are: c, 89.89; h, 4.87; and N, 5.24. ESI-MS (M/z) (M) by LC-MS combined analysis+): the theoretical value is 534.21 and the test value is 534.20.
TABLE 1
Figure BDA0002341327960000211
Figure BDA0002341327960000221
As can be seen from the above table 1, for visible light with the wavelength of 450-620nm, the refractive indexes of the nitrogen heterocyclic compounds containing azulene are all larger than 2.0, and the requirements of the light-emitting device on the refractive index of CPL are met, so that higher luminous efficiency is realized. In addition, the glass transition temperature of the nitrogen heterocyclic compounds is higher than 150 ℃, so that the nitrogen heterocyclic compounds have higher stability when applied to a light-emitting device.
Application example 1
The present embodiment provides an organic photoelectric device having a structure as shown in fig. 1, the organic photoelectric 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, a cathode 10 (an aluminum electrode) and a cap layer 11, wherein an upward arrow in FIG. 1 represents a light-emitting direction, wherein the thickness of the ITO anode 2 is 10nm, the thickness of the hole injection layer 3 is 10nm, the thickness of the first hole transport layer 4 is 95nm, 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, the thickness of the aluminum electrode 10 is 15nm, and the thickness of the cap layer (the cap layer 11) is 100 nm.
The preparation process of the organic photoelectric device is 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 10nm, 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 95nm, 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 codeposited on the second hole transport layer 5, wherein a compound BH is used as a main material of the light-emitting layer, BD is used as a doping material, the doping proportion is 3% (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.
10) Compound P1 was vacuum-deposited on cathode 10 as a cathode capping layer (cap layer 11) to a thickness of 100 nm.
Figure BDA0002341327960000231
Figure BDA0002341327960000241
Application example 2
The difference from application example 1 is that compound P1 was replaced by compound P13.
Figure BDA0002341327960000242
Application example 3
The difference from application example 1 is that compound P1 was replaced by compound P14.
Figure BDA0002341327960000251
Application example 4
The difference from application example 1 is that compound P1 was replaced by compound P47.
Figure BDA0002341327960000252
Application example 5
The difference from application example 1 is that compound P1 was replaced by compound P75.
Figure BDA0002341327960000253
Application example 6
The difference from application example 1 is that compound P1 was replaced by compound P90.
Figure BDA0002341327960000261
Application comparative example 1
The difference from application example 1 is that compound P1 was replaced by compound one.
Figure BDA0002341327960000262
Comparative application example 2
The difference from application example 1 is that compound P1 was replaced by compound two.
Figure BDA0002341327960000263
Table 2 test results of luminescence properties of devices
Figure BDA0002341327960000264
Figure BDA0002341327960000271
As can be seen from table 2, the CE of the device of the present application is generally high, and LT95 is generally long.
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 (10)

1. An organic compound having the following general structural formula:
Figure FDA0002341327950000011
X1、X2each independently selected from N atom or C-Ra, wherein, X1、X2At least one is an N atom;
ra is hydrogen, deuterium, halogen, nitro, nitrile, thioalkyl, a substituted or unsubstituted Cl to C20 alkyl group, a substituted or unsubstituted Cl to C20 alkoxy or thioalkyl group, a substituted or unsubstituted C3 to C20 cyclic alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C2 to C30 alkenyl or alkynyl group, -N (R is R1)2、-COR1、
Figure FDA0002341327950000012
Ra are independently present or are adjacent groups linked to each other to provide a substituted or unsubstituted aliphatic monocyclic or polycyclic ring, a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted heteroaromatic monocyclic or polycyclic ring;
r1 is a straight chain alkyl, alkoxy or thioalkyl group having 1 to 20C atoms or a cyclic alkyl, alkenyl or alkynyl group having 3 to 20C atoms;
Ar1、Ar2each independently selected from a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof;
l is independently selected from any one of a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group;
and m is the number of L and is an integer of 1-3.
2. An organic compound according to claim 1, wherein:
X1、X2each independently selected from N or C-Ra, wherein, X1、X2At least one is an N atom; ra is any one of hydrogen, deuterium, halogen, nitro, nitrile group, Cl-C20 alkyl group, C6-C30 aryl group and C2-C30 heterocyclic group;
Ar1、Ar2each independently selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted indolocarbafuranyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted indolocarbaphthenyl group, a substituted or unsubstituted benzofuranyl pyrimidinyl group, Any one of substituted or unsubstituted benzothiophene pyrimidinyl group, substituted or unsubstituted anthracenyl group, and substituted or unsubstituted pyrenyl group;
l is independently selected from any one of a single bond, a C6-C30 arylene group, a C2-C30 heteroarylene group;
and m is the number of L and is an integer of 1-3.
3. An organic compound according to claim 2, wherein:
X1、X2each independently selected from N atom or CRa, X1、X2At least one is an N atom; ra is H, D, F, C1, Br, I, CN, NO2Any one of the above;
Ar1、Ar2each independently selected from:
Figure FDA0002341327950000021
Figure FDA0002341327950000031
l is selected from a single bond,
Figure FDA0002341327950000032
Any one of the above;
# denotes the ligation site;
and m is the number of L and is an integer of 1-3.
4. The organic compound of claim 3, wherein:
X1、X2each independently selected from N or CRa, X1、X2At least one is N; ra is H;
Ar1、Ar2each independently selected from:
Figure FDA0002341327950000033
Figure FDA0002341327950000041
Figure FDA0002341327950000051
l is independently selected from a single bond,
Figure FDA0002341327950000052
Any one of the above;
# denotes the ligation site;
and m is the number of L and is an integer of 1-3.
5. The organic compound of claim 4, wherein:
X1、X2each independently selected from N or C-Ra, X1、X2At least one is N; ra is H;
Ar1、Ar2each independently selected from:
Figure FDA0002341327950000053
l is selected from a single bond,
Figure FDA0002341327950000054
One of (1);
# denotes the ligation site;
m is the number of L and takes the value of 1.
6. The organic compound of claim 1, wherein the organic compound is one of the following structures:
Figure FDA0002341327950000061
Figure FDA0002341327950000071
Figure FDA0002341327950000081
Figure FDA0002341327950000091
Figure FDA0002341327950000101
7. a display panel comprising an organic light emitting device comprising an anode, a cathode, at least one organic thin film layer between the anode and the cathode, wherein the organic thin film layer comprises at least one of the compounds of any one of claims 1 to 6.
8. The display panel according to claim 7, wherein the organic thin film layer further comprises an electron transport layer or a hole transport layer containing at least one of the compounds according to any one of claims 1 to 6.
9. The display panel according to claim 7 or 8, wherein the organic thin film layer further comprises a cap layer containing at least one of the compounds according to any one of claims 1 to 6.
10. A display device comprising the display panel according to any one of claims 7 to 9.
CN201911377317.6A 2019-12-27 2019-12-27 Organic compound, display panel and display device Active CN111116488B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201911377317.6A CN111116488B (en) 2019-12-27 2019-12-27 Organic compound, display panel and display device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911377317.6A CN111116488B (en) 2019-12-27 2019-12-27 Organic compound, display panel and display device

Publications (2)

Publication Number Publication Date
CN111116488A true CN111116488A (en) 2020-05-08
CN111116488B CN111116488B (en) 2023-05-23

Family

ID=70504015

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911377317.6A Active CN111116488B (en) 2019-12-27 2019-12-27 Organic compound, display panel and display device

Country Status (1)

Country Link
CN (1) CN111116488B (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109503466A (en) * 2018-12-24 2019-03-22 武汉天马微电子有限公司 Organic compound, display panel, and display device
CN109705148A (en) * 2018-12-28 2019-05-03 武汉天马微电子有限公司 Aromatic ring compound, display panel, and display device
CN109721598A (en) * 2018-12-29 2019-05-07 武汉天马微电子有限公司 Compound, display panel and display device
JP2019153659A (en) * 2018-03-02 2019-09-12 株式会社ジャパンディスプレイ Light emitting element and display device including the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019153659A (en) * 2018-03-02 2019-09-12 株式会社ジャパンディスプレイ Light emitting element and display device including the same
CN109503466A (en) * 2018-12-24 2019-03-22 武汉天马微电子有限公司 Organic compound, display panel, and display device
CN109705148A (en) * 2018-12-28 2019-05-03 武汉天马微电子有限公司 Aromatic ring compound, display panel, and display device
CN109721598A (en) * 2018-12-29 2019-05-07 武汉天马微电子有限公司 Compound, display panel and display device

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ALEXANDRU C. RAZUS 等: ""2-(Azulen-1-yl)-4,6-diphenyl substituted six-membered heteroaromatics"" *

Also Published As

Publication number Publication date
CN111116488B (en) 2023-05-23

Similar Documents

Publication Publication Date Title
CN109180567B (en) Nitrogen heterocyclic compound, display panel and display device
EP2719742B1 (en) Novel compounds and organic electronic device using same
CN109651173B (en) Compound, display panel and display device
CN109705148B (en) Aromatic ring compound, display panel, and display device
CN111253319B (en) Azacyclic compound, display panel and display device
CN111116505B (en) Amine compound and organic light-emitting device thereof
KR20140027141A (en) Organic electroluminescence element
CN110746391A (en) Compound, organic electroluminescent device and display device
CN110818675A (en) Organic compound and application thereof
CN112552275B (en) Spiro compound and application thereof
CN109336782B (en) Fluorene derivative and organic electroluminescent device thereof
CN111116489A (en) Compound, display panel and display device
CN113173858A (en) Nitrogen-containing compound, electronic component, and electronic device
CN111100126B (en) Compound, display panel and display device
CN112521401A (en) High-refractive-index benzo-heterocycle compound, organic light-emitting device and display device
CN111205293B (en) Heterocyclic compound, display panel and display device
CN111087387B (en) Organic compound, display panel and display device
CN111018898B (en) Compound, display panel and display device
CN116854677A (en) Capping layer material, preparation method thereof, organic electroluminescent device and display device
CN111635366A (en) Compound, display panel and display device
CN116425724A (en) Organic electroluminescent compound and organic electroluminescent device
CN112750957B (en) Organic electroluminescent device
CN109265445B (en) Azabiphenyl organic compound, display panel and display device
CN111116488B (en) Organic compound, display panel and display device
CN114530571A (en) Organic electroluminescent element

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