CN113121406A - Organic electroluminescent main body material and application thereof in organic electroluminescent device - Google Patents

Organic electroluminescent main body material and application thereof in organic electroluminescent device Download PDF

Info

Publication number
CN113121406A
CN113121406A CN201911425441.5A CN201911425441A CN113121406A CN 113121406 A CN113121406 A CN 113121406A CN 201911425441 A CN201911425441 A CN 201911425441A CN 113121406 A CN113121406 A CN 113121406A
Authority
CN
China
Prior art keywords
organic electroluminescent
host material
compound
emitting layer
carbon atoms
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.)
Pending
Application number
CN201911425441.5A
Other languages
Chinese (zh)
Inventor
孙杰
孙霞
杨楚罗
尹校君
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.)
Changzhou Tronly Eray Optoelectronics Material Co ltd
Shenzhen University
Original Assignee
Changzhou Tronly Eray Optoelectronics Material Co ltd
Shenzhen University
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 Changzhou Tronly Eray Optoelectronics Material Co ltd, Shenzhen University filed Critical Changzhou Tronly Eray Optoelectronics Material Co ltd
Priority to CN201911425441.5A priority Critical patent/CN113121406A/en
Publication of CN113121406A publication Critical patent/CN113121406A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring 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
    • 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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/1029—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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
    • 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

Abstract

The invention relates to an organic electroluminescent host material. In an organic electroluminescent device, in order to reduce problems of exciton quenching, efficiency roll-off, device lifetime reduction, and the like caused by too high concentration of excitons in a light emitting layer, a light emitting layer structure generally adopts a host-guest doping mode. The basic performance requirements for host materials vary with different luminescent material systems/mechanisms. The invention designs a class of organic electroluminescent host materials terminated based on 3,3 '-bi-carbazole units and 9, 9' -diphenylfluorene steric groups. The bi-combined carbazole unit endows the material with good carrier transport performance, and the end-group steric-hindrance end capping can effectively inhibit local aggregation of a light-emitting object. According to different luminescent material systems, the polarity and the size of molecules are adjusted by changing the difference of carbazole N-substituent (R), so that the comprehensive optimization of the device performance is realized.

Description

Organic electroluminescent main body material and application thereof in organic electroluminescent device
Technical Field
The invention relates to the technical field of luminescent materials, in particular to an organic electroluminescent main body material and an organic electroluminescent device.
Background
Organic light-emitting diodes (OLEDs) have been gradually developed into a new generation of electronic display and lighting technology due to their advantages of self-luminescence, flexibility, foldability, lightness, thinness, and more vivid color. Although the OLED technology is developed by panel manufacturers or application manufacturers such as apple, samsung, LG, beijing east, and huaxing photovoltaic panels at present to gradually realize commercial product output, some urgent problems still exist for the demand of commercial products, which mainly include that the device efficiency needs to be improved, the stability is poor, the efficiency roll-off is fast, and the material matching compatibility is not good. Among these, the most critical issues are also in the light emitting layer, involving exciton utilization and efficiency roll-off and stability degradation due to high concentration exciton quenching, and possible spectral red-shift due to dipole induction. Designing a host material with higher stability and good/balanced carrier transport capability and adjustable polarity to match a corresponding guest is essential to improve the relevant performance of the device.
Disclosure of Invention
In order to design a host material required by meeting different luminescent material systems and high-performance organic electroluminescent devices, the invention designs a host material based on bigeminal carbazole and end-group large-steric-hindrance end capping. The introduced bigeminal carbazole units are utilized to improve the charge transmission capability of the material, the large steric hindrance group of the end group not only can effectively disperse guest luminescent molecules, but also can regulate and control the energy transfer and the energy transfer of Dexter to a certain extent according to different sizes of exciton diffusion radiuses
Figure BDA0002353448370000012
The channel of energy transfer further realizes the comprehensive optimization of the device performance. In order to meet the requirements of different light-emitting object systems, an electron-withdrawing acceptor unit can be introduced by adjusting a substituent of an N substituent site at the other end of carbazole to improve the electron transmission performance, and proper molecular polarity is adjusted to optimize the comprehensive performances such as light-emitting property, service life and the like.
The class of host materials to which the present application relates may be represented by the following general formulae (i) and (II):
Figure BDA0002353448370000011
wherein R represents a substituent of any one single substitution site selected from a substituted or unsubstituted straight-chain alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted branched or cyclic alkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl or heteroaryl group having 5 to 60 carbon atoms, or a substituted or unsubstituted aryloxy or heteroaryloxy group having 5 to 60 carbon atoms;
l represents a substituent having a plurality of substitution sites selected from aryl or heteroaryl having 3 to 60 carbon atoms; n is an integer of 2 to 6.
Furthermore, the single substitution site group R in the general formula (I) mainly relates to some common unconjugated saturated aliphatic substituents, including naphthenic substituents such as cyclohexyl and cyclopentyl, and linear and branched alkanes, preferably chair cyclohexyl units.
Further, the monosubstitution site groups R in the general formula (I) mainly relate to some neutral conjugated aryl groups, including phenyl, polybiphenyl, polycyclic condensed rings, and preferably biphenyl.
Further, the monosubstituted site group R in the general formula (I) mainly relates to some electronegative conjugated heterocyclic electron acceptors, and can be five-membered heterocycles such as thiazole, oxazole and imidazole, six-membered heterocycles such as pyridine, pyrimidine, triazine and pyrazine, and multi-condensed rings such as quinoline, benzimidazole and phenanthroline. Among these receptors, pyridine and quinoline units are preferred.
Furthermore, the single substitution site group R in the general formula (I) can be spirofluorenyl, ortho-connected polysubstituted phenyl, tertiary butyl-containing aryl and the like, and the spirofluorenyl is preferred for regulating the molecular size and steric hindrance.
Further, the group L having multiple substitution sites in the general formula (ii) may be a benzene ring having 2 or more substitution sites, pyridine, pyrimidine, spirofluorene, anthracene ring, hexaphenylbenzene, etc., and pyridine, pyrimidine and spirofluorene when n ═ 2 are preferred.
Further, the organic electroluminescent layer prepared based on the host can be matched with a light-emitting object, such as a common fluorescent material, a light-emitting material with thermally activated delayed fluorescence, a phosphorescent light-emitting material, a free radical dual-state light-emitting material and the like.
Further, the organic electroluminescent material is selected from any one of the following compounds:
Figure BDA0002353448370000021
Figure BDA0002353448370000031
Figure BDA0002353448370000041
Figure BDA0002353448370000051
drawings
The accompanying drawings, which are incorporated in and constitute a part of this application, illustrate embodiments of the invention and, together with the description, serve to explain the invention and not to limit the invention. In the drawings:
fig. 1 shows a schematic structural diagram of an OLED device provided according to an embodiment of the present invention.
Fig. 2 shows a current-voltage-luminance curve of an embodiment of the organic electroluminescent device.
Fig. 3 shows the External Quantum Efficiency (EQE), Current Efficiency (CE) and Power Efficiency (PE) versus current density for an embodiment of the organic electroluminescent device.
Fig. 4 shows an electroluminescence spectrum of an embodiment of the organic electroluminescence device.
Wherein the figures include the following reference numerals:
100. an anode layer; 101. a hole injection layer; 102. a hole transport layer; 103. a light emitting layer; 104. an electron transport layer; 105. an electron injection layer; 106. a cathode layer.
Detailed Description
It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict. The present invention will be described in detail below with reference to the embodiments with reference to the attached drawings.
As analyzed by the background art of the present application, the luminescent host material in the prior art still has the problems of low exciton utilization rate, fast efficiency roll-off and poor compatibility with an object, and the present application provides an organic electroluminescent host material and an application thereof in an organic electroluminescent device.
In an exemplary embodiment of the present application, there is provided an organic electroluminescent material having a structure represented by general formulae (I) and (ii),
Figure BDA0002353448370000061
wherein R represents a substituent at any one single substitution site selected from a substituted or unsubstituted straight-chain alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted branched or cyclic alkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl or heteroaryl group having 5 to 60 carbon atoms;
l represents a substituent having a plurality of substitution sites selected from aryl or heteroaryl having 3 to 60 carbon atoms;
n is an integer of 2 to 6.
The structural general formula contains the duplex carbazole unit, so that the hole transport property of the material is ensured, the thermal stability of the material is improved, meanwhile, 9-diphenylfluorene is introduced into the end part to increase the steric hindrance of the structure, the guest is favorably dispersed in the host material, and the local agglomeration of the guest is effectively inhibited.
In one embodiment of the present application, in order to increase the hole transport and steric hindrance of the above organic electroluminescent material, R may be further selected from the following neutral substituent groups:
Figure BDA0002353448370000071
in one embodiment of the present application, in order to further increase the steric hindrance of the organic electroluminescent host material and inhibit the crystallization tendency of the material, R may be further selected from the following twisting groups with large steric hindrance:
Figure BDA0002353448370000072
in one embodiment of the present application, in order to balance the hole/electron transport properties of the organic electroluminescent host material or adjust the polarity of the molecule, R may be further selected from the following electronegative conjugated heterocycles with certain electron affinities:
Figure BDA0002353448370000073
Figure BDA0002353448370000081
in one embodiment of the present application, in order to increase the solubility of the above organic electroluminescent host material in a solution, the dendrimer structure is realized by multiple substitution sites L selected from the following groups having multiple substitution sites:
Figure BDA0002353448370000091
further, in an embodiment, the organic electroluminescent material can be used as a light emitting layer in combination with the following objects: common fluorescent materials, luminescent materials with thermal activation delayed fluorescence, phosphorescent luminescent materials, free radical dual-state luminescent materials and the like.
In still another exemplary embodiment of the present application, there is provided an organic electroluminescent device including a light emitting layer including an organic electroluminescent host material, the organic electroluminescent host material being any one of the organic electroluminescent host materials described above. The organic electroluminescent material is arranged in the luminescent layer, so that high luminescent efficiency can be provided for an organic electroluminescent device, and the phenomenon of fast efficiency roll-off is reduced.
The organic electroluminescent device may be an organic electroluminescent device commonly used in the art, for example, having at least one cathode, one anode and one functional layer therebetween, wherein the light-emitting layer is used as one of the functional layers. Preferably, the organic electroluminescent device further comprises a first transparent electrode layer, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a second transparent electrode layer, which are sequentially stacked.
In one embodiment of the present application, the electroluminescent wavelength of the organic electroluminescent device is between 400nm and 900 nm.
The present invention will be described with reference to preferred embodiments but is not limited to the following embodiments, it being understood that the scope of the invention is covered by the appended claims. Those skilled in the art, guided by the teachings of the present invention, will recognize that certain changes may be made to the embodiments of the invention, which are encompassed within the spirit and scope of the invention, which is set forth in the following claims.
The preparation method of the organic electroluminescent main body material comprises the following steps:
example 1-1: synthesis of Compound 2
(a) Synthesis of intermediate BrDPFCZ
Figure BDA0002353448370000101
Starting materials BrPhCZ (3.22g, 10mmol), 9, 9-diphenylfluorene-2-boronic acid pinacol ester (4.45g, 10mmol) and palladium tetratriphenylphosphine (346.7mg, 0.3mmol) were added in sequence to a 250mL flask, which was evacuated three times and then 60mL of toluene, 30mL of ethanol and 20mL of 2M K were added by syringe2CO3The solution was stirred at 90 ℃ overnight. After cooling to room temperature, extraction with dichloromethane was carried out, the combined organic phases were concentrated under reduced pressure and then purified by column chromatography (petroleum ether/dichloromethane as mobile phase) to give intermediate DPFCZ (4.48g, 80% yield). Dissolving DPFCZ in 50mL of chloroform, stirring the solution in the dark, dropwise adding a DMF (20mL) solution of NBS (1.4g, 8mmol) in an equimolar amount, stirring the solution at room temperature for 3 to 5 hours, removing the organic solvent under reduced pressure, and carrying out column chromatography separation and purification to obtain an intermediate BrDPFCZ (4.6g, yield 90%).
(b) Synthesis of intermediate DPhCZB
Figure BDA0002353448370000102
The starting material BrPhCZ (3.22g, 10mmol), phenylboronic acid (1.34g, 11mmol), and palladium tetratriphenylphosphine (346mg, 0.3mmol) were added sequentially to a 250mL round-bottomed flask, which was evacuated three times and then charged with degassed 60mL toluene, 30mL ethanol, and 20mL 2M K using a syringe2CO3The solution was stirred at 90 ℃ overnight. After cooling to room temperature, extraction was carried out with dichloromethane, the combined organic phases were concentrated under reduced pressure and purified by column chromatography (petroleum ether/dichloromethane as mobile phase) to give DPhCZ (2.71g, 85%). Then directly put into the next step, NBS (1.51g) is added for bromination at room temperature, column chromatography purification is carried out to obtain an intermediate, the intermediate is completely dried and placed into a 250mL flask, and potassium acetate (4.16g, 42.5mmol) and Pd (dppf) Cl are added in sequence2(187mg, 0.26mmol), pinacol ester diboron (Bpin)2(2.38g, 9.35mmol), 90mL of 1, 4-dioxane, and the mixture was stirred at 85 ℃ overnight, cooled, and the organic solvent was removed under reduced pressure. Column chromatography isolation and purification yielded another intermediate, DPhCZB (2.84g, 70% yield).
(c) Synthesis of Compound 2
Figure BDA0002353448370000111
Equimolar amounts of intermediate DPhCZB (1.78g, 4mmol) and BrDPFCZ (2.56g, 4mmol), palladium tetratriphenylphosphine (138mg, 0.12mmol) were added to a 250mL flask in that order, and after three puffs 50mL of toluene, 10mL of ethanol and 10mL of 2M K were added via syringe2CO3And stirring the solution at 95-100 ℃ overnight. After cooling to room temperature, extraction with dichloromethane was carried out, the combined organic phases were concentrated under reduced pressure, and then subjected to separation and purification by column chromatography (mobile phase petroleum ether/dichloromethane) to obtain the objective product 2(2.63g, yield 75%). And recrystallizing and sublimating the primary product in sequence to obtain the high-purity compound 2 with the purity of 99.98%.
The characterization results for compound 2 are as follows:
1H NMR(400MHz,CDCl3)δ[ppm]:8.48(s,2H),8.25(t,J＝4.4Hz,2H),7.87-7.79(m,6H),7.71-7.67(m,8H),7.61-7.29(m,30H)。
HRMS(ESI,m/z):caclcd for C67H44N2[M]+876.3505,found:876.3506。
examples 1 to 2: synthesis of Compound 19
(a) Synthesis of intermediate CHCZB
Figure BDA0002353448370000112
Firstly, 11mmol (440mg, 60%) NaH and 60mL ultra-dry DMF are added into a 150mL two-neck flask, then 3-bromocarbazole (2.46g, 10mmol) is slowly added under the condition of introducing argon, stirring is carried out for 2h at room temperature, then 1-bromocyclohexane (1.79g, 11mmol) is added, stirring is carried out overnight at room temperature, water is poured into the flask, filtering is carried out, the flask is washed clean by an ethanol/water mixed solvent, and the solid matter is dried in a vacuum drying oven and directly used for the next reaction. To this was added potassium acetate (3.92g, 40mmol), Pd (dppf) Cl2(220mg, 0.3mmol), pinacol diboron (2.79g, 11mmol), and 90mL of 1, 4-dioxane were stirred at 80 ℃ for 12 hours, cooled, and the organic solvent was removed under reduced pressure. Column chromatography isolation and purification yielded CHCZB as an intermediate (2.44g, 65% yield).
(a) Synthesis of Compound 19
Figure BDA0002353448370000121
Intermediate CHCZB (1.5g, 4mmol) was added to a 250mL flask with intermediate BrDPFCZ (2.56g, 4mmol) and palladium tetratriphenylphosphine (138mg, 0.12mmol) in that order, and after three puffs 60mL of toluene, 10mL of ethanol and 20mL of 2M K were added with a syringe2CO3And stirring the solution for 24 hours at the temperature of 95-100 ℃. After cooling to room temperature, extraction with dichloromethane was carried out, the combined organic phases were concentrated under reduced pressure, and then subjected to column chromatography (petroleum ether/dichloromethane as mobile phase) to obtain the objective product 19(2.74g, 85%). The initial product is then recrystallized (chloroform/isopropanol) and sublimed to obtain the high-purity compound 19 with the purity of 99.96%.
The characterization of compound 19 is as follows:
1H NMR(400MHz,CDCl3)δ[ppm]:8.36-8.21(m,2H),8.13(d,J＝6.6Hz,2H),7.86-7.12(m,31H),3.62(m,1H),1.84-1.62(m,4H),1.22-0.84(m,6H)。
HRMS(ESI,m/z):caclcd for C61H46N2[M]+806.3661,found:806.3655。
examples 1 to 3: synthesis of Compound 31
(a) Synthesis of intermediate PMCZB
Figure BDA0002353448370000122
3-Bromocarbazole (2.46g, 10mmol), 5-iodopyrimidine (2.47g, 12mmol), Pd2(dba)3(183mg, 0.2mmol), sodium tert-butoxide (1.06g, 11mmol), tri-tert-butylphosphine (121mg, 0.6mmol) in a 250mL flask, 100mL of redistilled toluene was added, refluxed for 24h, cooled and extracted with dichloromethane/water, the organic phases were combined, distilled under reduced pressure to give a crude product, and purified by column chromatography to give intermediate PMCZ (2.11g, 65%). The intermediate was then reacted with potassium acetate (3.82g, 39mmol), Pd (dppf) Cl2(146mg, 0.2mmol), pinacol diboron (1.82g, 7.2mmol), and 90mL of 1, 4-dioxane were stirred at 85 ℃ for 15 hours, cooled, and the organic solvent was removed under reduced pressure. Column chromatography isolation and purification yielded the intermediate PMCZB (1.57g, 65% yield).
(b) Synthesis of Compound 31
Figure BDA0002353448370000131
Finally, the intermediate PMCZB (742mg, 2mmol) was added to a 250mL flask with BrDPFCZ (1.28g, 2mmol) and palladium tetratriphenylphosphine (69mg, 0.06mmol) in that order, and after three puffs 30mL of toluene, 5mL of ethanol and 10mL of 2M K were added with a syringe2CO3And stirring the solution for 24 hours at the temperature of 95-100 ℃. Cooling to room temperature, extracting with dichloromethane, mixing organic phases, concentrating under reduced pressure, and performing column chromatography (mobile phase isPetroleum ether/dichloromethane) to obtain the target product 31(1.2g, 75%). The initial product is recrystallized (dichloromethane/methanol) and sublimated to obtain a high-purity compound with the purity of 99.95 percent.
The characterization of compound 31 is as follows:
1H NMR(400MHz,CDCl3)δ[ppm]:9.25(s,1H),8.87(s,2H),8.36(d,J＝4.8Hz,2H),7.86-7.12(m,33H)。
HRMS(ESI,m/z):caclcd for C59H38N4[M]+802.3096,found:802.3094。
examples 1 to 3: synthesis of Compound 34
(a) Synthesis of intermediate TrzCZB
Figure BDA0002353448370000132
Firstly, 11mmol (440mg, 60%) NaH and 60mL of ultra-dry DMF are added into a 150mL two-neck flask, then 3-bromocarbazole (2.46g, 10mmol) is slowly added under the condition of introducing argon, stirring is carried out at room temperature for 2-5 h, then 3, 5-diphenyl-1-chloro-tricyanogen (2.95g, 11mmol) is slowly added under the protection of argon, stirring is carried out at room temperature overnight, the mixture is poured into water for quenching, dichloromethane is used for extraction, and ethanol is used for recrystallization to obtain TrzCZ (3.11g, yield 65%). Then, TrzCZ (3.11, 6.5 mmol), potassium acetate (3.92g, 40mmol), Pd (dppf) Cl2(220mg, 0.3mmol), pinacol diboron (1.95g, 7.7mmol), and 90mL of 1, 4-dioxane were stirred at 80 ℃ for 12 hours, cooled, and the organic solvent was removed under reduced pressure. Column chromatography isolation and purification yielded the intermediate TrzCZB (2.21g, 65% yield).
(b) Synthesis of Compound 34
Figure BDA0002353448370000141
The resulting intermediate TrzCZB (1.05g, 2mmol) was added to a 250mL flask with the intermediates BrDPFCZ (1.28g, 2mmol) and palladium tetratriphenylphosphine (69mg, 0.06mmol) in that order, and after three puffs 30mL of toluene, 5mL of ethanol and 10mL of 2MK2CO3And stirring the solution for 24 hours at the temperature of 95-100 ℃. After cooling to room temperature, extraction with dichloromethane was carried out, the combined organic phases were concentrated under reduced pressure and then subjected to column chromatography (petroleum ether/dichloromethane as mobile phase) to obtain the desired product 34(1.45g, 75%). The initial product is then recrystallized (toluene/isopropanol) and sublimed to obtain the high-purity compound 34 with the purity of 99.96%.
The characterization of compound 34 is as follows:
HRMS(ESI,m/z):caclcd for C70H45N5[M]+955.3675,found:955.3672。
examples 1 to 4: synthesis of Compound 54
Figure BDA0002353448370000142
Starting materials BrDPFCZ (1.92g, 3mmol), palladium tetratriphenylphosphine (115mg, 0.1mmol), pinacol diboron diboride (812mg, 3.2mmol), degassed 1, 4-dioxane 60mL and 1.66g of K2CO3Into a 150mL round bottom flask. Reacting at 90-95 ℃ for 24h, cooling, extracting with dichloromethane/water, combining the obtained organic phases, distilling under reduced pressure to obtain a crude product, separating and purifying by column chromatography (eluent, dichloromethane/petroleum ether/ethyl acetate) to obtain pure 54(1.51g, 45%), and recrystallizing the crude product (chloroform/isopropanol) for multiple times to obtain the compound 54 with higher purity, wherein the purity is 99.92%.
Characterization of compound 54 resulted in the following:
HRMS(ESI,m/z):caclcd for C86H56N2[M]+1116.4443,found:1116.4447。
examples 1 to 4: synthesis of Compound 55
(a) Synthesis of intermediate DBCZPh
Figure BDA0002353448370000151
Starting materials 3-bromocarbazole (2.46g, 10mmol), 1, 4-diiodobenzene (1.02g, 5mmol)l)，Pd2(dba)3(275mg, 0.3mmol), sodium tert-butoxide (1.06g, 11mmol), tri-tert-butylphosphine (121mg, 0.6mmol) to give DBrCZPh (3.74g, 66% yield) by C-N coupling. Then 3mmol of DBrCZPh (1.70g) were mixed with potassium acetate (1.76g, 18mmol), Pd (dppf) Cl2(66mg, 0.09mmol), pinacol diboron (1.78g, 7.0mmol), and 80mL of 1, 4-dioxane were stirred at 85 ℃ for 24 hours, stirred and cooled, and then stirred, and the organic solvent was removed under reduced pressure. Column chromatography isolation and purification yielded the intermediate DBCZPh (1.22g, 62% yield).
(b) Synthesis of Compound 55
Figure BDA0002353448370000152
The intermediate DBCZPh (670mg, 1mmol) was added to a 250mL flask with BrDPFCZ (1.28g, 2mmol) and palladium tetratriphenylphosphine (69mg, 0.06mmol) in that order, and after three puffs 40mL toluene, 8mL ethanol and 12mL 2M K were added with a syringe2CO3And stirring the solution for 24 hours at the temperature of 95-100 ℃. After cooling to room temperature, extraction with dichloromethane was carried out, the combined organic phases were concentrated under reduced pressure, and then subjected to column chromatography (petroleum ether/dichloromethane as mobile phase) to separate and purify the target product 55(1.14g, 75%). The initial product is recrystallized for multiple times (chloroform/methanol) to obtain the high-purity compound 55 with the purity of 99.96 percent.
The characterization of compound 55 resulted in the following:
HRMS(ESI,m/z):caclcd for C116H74N4[M]+1522.5913,found:1522.5916。
preparation of organic electroluminescent device:
the organic compound of the present invention is particularly suitable for the light emitting layer in the OLED device, and the application effect of the organic electroluminescent host material of the present invention as the light emitting layer in the OLED device is described in detail by the following specific examples 1 to 4 in conjunction with the device structure of fig. 1.
The structural formula of the organic material used is as follows:
Figure BDA0002353448370000161
an organic electroluminescent device in which the organic electroluminescent host material of the present invention is used as a light emitting layer may include a glass and transparent conductive layer (ITO) substrate layer 100, a hole injection layer 101(4, 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ], TAPC), a hole transport layer 102(4,4',4' -tris (carbazol-9-yl) triphenylamine, TCTA), a light emitting layer 103 (the organic electroluminescent host material of the present invention or a mixture in which the host material is doped with it as a light emitting material), an electron transport layer 104(3,3' - [5' - [3- (3-pyridyl) phenyl ] [1,1':3',1 ″ -terphenyl ] -3,3 ″ -diyl ] bipyridine, TmPyPB), an electron injection layer 105 (8-hydroxyquinoline lithium, LiQ) and cathode layer 106 (aluminum, Al).
Example 1
Referring to the structure shown in fig. 1, the OLED device is manufactured by the following specific steps: ultrasonically washing a glass substrate coated with ITO (indium tin oxide) with the thickness of 90nm for 5 minutes by using isopropanol and pure water respectively, cleaning by using ultraviolet ozone, and then conveying the glass substrate into a vacuum deposition chamber; the hole injecting material TAPC was evacuated at a thickness of 30nm (about 10 nm)-7Torr) is thermally deposited on the transparent ITO electrode to form a hole injection layer; vacuum-depositing TCTA with the thickness of 5nm on the hole injection layer to be used as a hole transport layer; vacuum deposition of 6% Ir (ppy) dopant concentration on hole transport layer3The compound 2 of (1), as a light-emitting layer; depositing TmPyPB with the thickness of 55nm on the light-emitting layer to form an electron transport layer, and finally depositing LiQ (electron injection layer) with the thickness of 1.5nm and aluminum with the thickness of 100nm in sequence to form a cathode; the device was transferred from the deposition chamber into a glove box and then encapsulated with a UV curable epoxy and a glass cover plate containing a moisture absorber.
In the above manufacturing steps, the deposition rates of the organic material, LiQ and aluminum were maintained at 0.1nm/s, 0.05nm/s and 0.2nm/s, respectively.
The device structure is represented as: ITO (90nm)/TAPC (30nm)/TCTA (5 nm)/Compound 2: ir (ppy)3(6wt.％,20nm)/TmPyPB(65nm)/LiQ(1.5nm)/Al(100nm)。
Example 2
An experiment was performed in the same manner as in example 1 except that: as the light-emitting layer, compound 31 was used instead of compound 2 in example 1.
The device structure is represented as: ITO (90nm)/TAPC (30nm)/TCTA (5 nm)/Compound 31: ir (ppy)3(6wt.％,20nm)/TmPyPB(65nm)/LiQ(1.5nm)/Al(100nm)。
Example 3
An experiment was performed in the same manner as in example 1 except that: as the light-emitting layer, fluorescent guest PXZ-PM was used in place of phosphorescent guest Ir (ppy) in example 13。
The device structure is represented as: ITO (90nm)/TAPC (30nm)/TCTA (5 nm)/Compound 2: PXZ-PM (6 wt.%, 20nm)/TmPyPB (65nm)/LiQ (1.5nm)/Al (100 nm).
Example 4
An experiment was performed in the same manner as in example 3 except that: as the light-emitting layer, compound 31 was used instead of compound 2 in example 3.
The device structure is represented as: ITO (90nm)/TAPC (30nm)/TCTA (5 nm)/Compound 31: PXZ-PM (6 wt.%, 20nm)/TmPyPB (65nm)/LiQ (1.5nm)/Al (100 nm).
The devices prepared above were subjected to performance tests, and the luminance, luminous efficiency, EQE (external quantum efficiency) of the devices were measured by a Keithley source measurement system (Keithley 2400source meter, Keithley 2000Currentmeter) with calibrated silicon photodiodes, and the electroluminescence spectra were measured by a SPEX CCD3000 spectrometer of JY company, france, all in room temperature atmosphere, and the results of the measurements are shown in table 1.
TABLE 1
Numbering Main body Object EQE(％) CE(cd/A) PE(Lm/W) EL(nm)
Example 1 Compound 2 Ir(ppy)3 17.9 67.6 35.4 529
Example 2 Compound 31 Ir(ppy)3 19.3 72.5 41.4 529
Example 3 Compound 2 PXZ-PM 13.6 45.4 22.0 536
Example 4 Compound 31 PXZ-PM 19.3 65.2 37.2 540
From the above description, it can be seen that the above-described embodiments of the present invention achieve the following technical effects:
the compound 2 and the compound 31 are respectively matched with two different green light objects to show higher device efficiency, and because the pyrimidine group is introduced into the compound 2 to increase the electron transfer characteristic of the host luminescent material, the device efficiency is higher than that of a device using the compound 2 as the luminescent host material. It can also be seen from fig. 3 that the efficiency roll-off is smaller for device examples 1 to 3. The large roll-off in efficiency of device example 4 is probably due to poor matching between compound 31 and fluorescent guest PXZ-PM, PXZ-PM is an electron type guest and therefore is better matched with host light emitting material compound 2 of a hole bias type.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (8)

1. An organic electroluminescent host material, characterized in that the material can be represented by general formulae (I) and (II):
Figure FDA0002353448360000011
wherein R represents a substituent at any one single substitution site selected from a substituted or unsubstituted straight-chain alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted branched or cyclic alkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted aryl or heteroaryl group having 5 to 60 carbon atoms;
l represents a substituent having a plurality of substitution sites selected from aryl or heteroaryl having 3 to 60 carbon atoms;
n is an integer of 2 to 6.
2. The organic electroluminescent host material of claim 1, wherein R is selected from the following neutral groups, but not limited to:
Figure FDA0002353448360000012
wherein m is preferably an integer of 1 to 8.
3. The organic electroluminescent host material according to claim 1, wherein R is selected from the following twisted groups with large steric hindrance, but not limited thereto:
Figure FDA0002353448360000021
4. the organic electroluminescent host material of claim 1, wherein R is selected from the following electronegative groups, but not limited to:
Figure FDA0002353448360000022
Figure FDA0002353448360000031
5. the organic electroluminescent host material according to claim 1, wherein L is selected from the following groups having two or more substitution sites, but not limited thereto:
Figure FDA0002353448360000032
6. the organic electroluminescent host material of claim 1, wherein n is preferably 2.
7. The organic electroluminescent host material of claim 1, wherein the material can be applied to a light-emitting layer in an organic electroluminescent device, and the organic electroluminescent device can be prepared by vacuum evaporation or solution spin coating.
8. The organic electroluminescent host material according to claim 7, wherein the material is used in combination with the following objects when applied to a light-emitting layer: common fluorescent materials, luminescent materials with thermal activation delayed fluorescence, phosphorescent luminescent materials, free radical dual-state luminescent materials and the like.
CN201911425441.5A 2019-12-31 2019-12-31 Organic electroluminescent main body material and application thereof in organic electroluminescent device Pending CN113121406A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201911425441.5A CN113121406A (en) 2019-12-31 2019-12-31 Organic electroluminescent main body material and application thereof in organic electroluminescent device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911425441.5A CN113121406A (en) 2019-12-31 2019-12-31 Organic electroluminescent main body material and application thereof in organic electroluminescent device

Publications (1)

Publication Number Publication Date
CN113121406A true CN113121406A (en) 2021-07-16

Family

ID=76771012

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911425441.5A Pending CN113121406A (en) 2019-12-31 2019-12-31 Organic electroluminescent main body material and application thereof in organic electroluminescent device

Country Status (1)

Country Link
CN (1) CN113121406A (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016036171A1 (en) * 2014-09-04 2016-03-10 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent devices comprising the same
CN106604911A (en) * 2014-08-20 2017-04-26 罗门哈斯电子材料韩国有限公司 A plurality of host materials and an organic electroluminescence device comprising the same
JP2017141167A (en) * 2016-02-08 2017-08-17 出光興産株式会社 Compound, material for organic electroluminescent element using the same, organic electroluminescent element using the same, luminaire and display device
US20190103560A1 (en) * 2016-12-27 2019-04-04 Soulbrain Co., Ltd. Compound and organic light emitting device comprising the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106604911A (en) * 2014-08-20 2017-04-26 罗门哈斯电子材料韩国有限公司 A plurality of host materials and an organic electroluminescence device comprising the same
WO2016036171A1 (en) * 2014-09-04 2016-03-10 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent devices comprising the same
JP2017141167A (en) * 2016-02-08 2017-08-17 出光興産株式会社 Compound, material for organic electroluminescent element using the same, organic electroluminescent element using the same, luminaire and display device
US20190103560A1 (en) * 2016-12-27 2019-04-04 Soulbrain Co., Ltd. Compound and organic light emitting device comprising the same

Similar Documents

Publication Publication Date Title
KR101703016B1 (en) Fluorenes and electronic devices containing them
TWI646171B (en) Compounds and organic electronic devices
KR101772371B1 (en) Compounds and organic electronic devices
KR101739629B1 (en) Materials for electronic devices
CN111675698B (en) Organic electroluminescent material and device thereof
CN114591328B (en) Carbazole derivative and application thereof
CN114163424A (en) Organic electroluminescent material and device thereof
CN113943279A (en) Carbazole derivative, organic electroluminescent element, display device, and lighting device
CN112592341A (en) Organic photoelectric functional material and organic electroluminescent device prepared from same
CN114516861B (en) Carbazole derivative, organic electroluminescent element, display device, and lighting device
CN110963904A (en) Compound with ketone and fluorene as cores, preparation method and application thereof
CN114249738A (en) Electroluminescent material and device
CN110655486A (en) Compound with dibenzosuberene as core and application thereof
CN116162083A (en) Heterocyclic compound with cyano substituent
CN113121406A (en) Organic electroluminescent main body material and application thereof in organic electroluminescent device
CN113292488B (en) Cyano-containing aza-benzene compound, application thereof and organic electroluminescent device containing compound
CN112707908B (en) Organic electronic material and application thereof
CN117327056A (en) Organic electroluminescent material and device thereof
CN117209517A (en) Condensed heterocyclic compound, application thereof and organic electroluminescent device containing same
KR20230041950A (en) Organic electroluminescent device
CN116375633A (en) Novel triarylamine compound and organic electroluminescent device containing same
KR20220083965A (en) Organic electroluminescent material and device thereof
CN116425724A (en) Organic electroluminescent compound and organic electroluminescent device
CN115734630A (en) Organic electroluminescent device

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20210716

WD01 Invention patent application deemed withdrawn after publication