CN112939890A - Heterocyclic organic photoelectric material, preparation method thereof and organic electroluminescent device - Google Patents

Heterocyclic organic photoelectric material, preparation method thereof and organic electroluminescent device Download PDF

Info

Publication number
CN112939890A
CN112939890A CN202110156296.6A CN202110156296A CN112939890A CN 112939890 A CN112939890 A CN 112939890A CN 202110156296 A CN202110156296 A CN 202110156296A CN 112939890 A CN112939890 A CN 112939890A
Authority
CN
China
Prior art keywords
organic photoelectric
formula
photoelectric material
heterocyclic organic
heterocyclic
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.)
Withdrawn
Application number
CN202110156296.6A
Other languages
Chinese (zh)
Inventor
王辉
李小龙
李猛
张国旭
常胜
杜磊
马晓宇
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.)
Jilin Optical and Electronic Materials Co Ltd
Original Assignee
Jilin Optical and Electronic Materials 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 Jilin Optical and Electronic Materials Co Ltd filed Critical Jilin Optical and Electronic Materials Co Ltd
Priority to CN202110156296.6A priority Critical patent/CN112939890A/en
Publication of CN112939890A publication Critical patent/CN112939890A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
    • 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
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/653—Five-membered rings
    • C07F9/65324—Five-membered rings condensed with carbocyclic rings or carbocyclic ring 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
    • C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
    • C07F9/6539—Five-membered rings
    • C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring 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
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • 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
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—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
    • H10K85/626—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
    • 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
    • C09K2211/1007—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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three 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

Abstract

The invention discloses a heterocyclic organic photoelectric material, a preparation method thereof and an organic electroluminescent device, belonging to the technical field of chemistry and luminescent materials, wherein the heterocyclic organic photoelectric material has a general structural formula as follows:
Figure DDA0002933632750000011
in the formula, R1、R2And R3Each independently selected from at least one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 6-to 30-membered aromatic heterocyclic group, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C5-C30 spiro ring; and R is1、R2And R3At any position of the ring in which they are located; x is O or S, Y is N or P; m, n and p are all natural numbers. The heterocyclic organic photoelectric material is applied to the field of organic electroluminescence, is used as a main material of a light-emitting layer, can reduce the driving voltage of a device, improves the light-emitting efficiency of the device and prolongs the service life of the device.

Description

Heterocyclic organic photoelectric material, preparation method thereof and organic electroluminescent device
Technical Field
The invention relates to the technical field of chemical and luminescent materials, in particular to a heterocyclic organic photoelectric material, a preparation method thereof and an organic electroluminescent device.
Background
Organic Light Emitting Diodes (OLEDs) take advantage of the light emitting properties of materials when excited by an electrical current. OLEDs are of particular interest as alternatives to cathode ray tubes and liquid crystal displays for producing flat visual display units. Devices comprising OLEDs are particularly suitable for mobile applications, such as for mobile phones, notebook computers, lighting, etc., due to their very compact construction and inherently low power consumption, and organic electroluminescent devices have attracted attention in the field of new generation large area flat panel displays and semiconductor solid state lighting sources due to their advantages of self-emission, fast response, high brightness, flexibility, rollability, etc.
Since the first report of high efficiency organic light emitting diodes, the industry has been working on how to improve the efficiency and stability of the device. The phosphorescent material has strong spin-orbit coupling effect, and can simultaneously utilize singlet excitons and triplet excitons, so that the quantum efficiency in the phosphorescent electroluminescent device theoretically reaches 100 percent. However, the phosphorescent material has a long excited-state lifetime, and triplet-triplet annihilation and triplet-polaron annihilation are easily formed when the triplet exciton concentration is high, resulting in a serious decrease in efficiency. Therefore, phosphorescent materials are often incorporated as guests into host materials to reduce the self-concentration quenching process. It is important to select a suitable host material in phosphorescent organic electroluminescent devices (Ph OLEDs). For example, a host material with a wide band gap may cause an increase in the turn-on voltage of the phosphorescent organic electroluminescent device, and accordingly, high efficiency may be obtained. The appropriate host material is selected, and then the host-guest doping mode is adopted to adjust the light color, the brightness and the efficiency, so that the purpose of improving the performance of the organic electroluminescent display device can be achieved. In general, the requisite properties of the host material include: (1) the high triplet state energy level is possessed; (2) the carrier mobility is better and can be matched with the energy level of the adjacent layer; (3) has high thermal stability and film forming stability.
At present, OLED display and illumination are widely commercialized and applied, the photoelectric requirement of a client terminal on an OLED screen body is continuously improved, and in order to meet the requirements, in addition to the lean refinement in the OLED panel manufacturing process, the development of OLED materials capable of meeting higher device indexes is very important. Therefore, the development of stable and efficient host materials can reduce the driving voltage, improve the luminous efficiency and the service life of the device, and have important practical application value.
Disclosure of Invention
An object of embodiments of the present invention is to provide a heterocyclic organic photoelectric material to solve the above problems in the background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
a heterocyclic organic photoelectric material has a structural general formula as formula I:
Figure BDA0002933632740000021
in the formula, R1、R2And R3Each independently selected from at least one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 6-to 30-membered aromatic heterocyclic group, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C5-C30 spiro ring; and R is1、R2And R3At any position of the ring in which they are located;
x is O or S, Y is N or P; m, n and p are all natural numbers.
Preferably, in the formula, X is O.
Preferably, in the formula, Y is N.
Preferably, m is a natural number not greater than 4.
Preferably, n is a natural number not greater than 4.
Preferably, p is a natural number not greater than 5.
Preferably, the chemical structural formula of the heterocyclic organic photoelectric material is any one of formula I-1 to formula I-118:
Figure BDA0002933632740000031
Figure BDA0002933632740000041
Figure BDA0002933632740000051
Figure BDA0002933632740000061
Figure BDA0002933632740000071
Figure BDA0002933632740000081
Figure BDA0002933632740000091
Figure BDA0002933632740000101
Figure BDA0002933632740000111
Figure BDA0002933632740000121
Figure BDA0002933632740000131
Figure BDA0002933632740000141
Figure BDA0002933632740000151
Figure BDA0002933632740000161
Figure BDA0002933632740000171
another objective of the embodiments of the present invention is to provide a method for preparing the heterocyclic organic photoelectric material, which includes the following steps:
Figure BDA0002933632740000181
under the protective atmosphere, mixing a compound shown as a formula II, a compound shown as a formula III, anhydrous potassium carbonate, toluene, anhydrous ethanol and water, and then adding tetrakis (triphenylphosphine) palladium to perform reflux reaction to obtain the heterocyclic organic photoelectric material; wherein Z represents a halogen.
In the above step, the molar ratio of the compound represented by the formula ii, the compound represented by the formula iii, the anhydrous potassium carbonate, and the tetrakis (triphenylphosphine) palladium is 1: (1.1-1.3): (2.5-3.5): (0.5% -2.5%), wherein the volume ratio of the toluene to the absolute ethyl alcohol to the purified water is 2:1:1, the mass volume ratio of the compound shown in the formula II to the toluene is 1g (8-12mL), and the reaction time is 10-20 hours.
In the above synthetic route: in the structural formulas II and III, Z is specifically one of F, Cl, Br and I, and the rest limitations are consistent with the requirements of the structural formula I and are not repeated herein.
Another object of the embodiments of the present invention is to provide an application of the heterocyclic organic photoelectric material in the preparation of organic electroluminescent devices.
It is another object of an embodiment of the present invention to provide an organic electroluminescent device, which includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes the heterocyclic organic photoelectric material.
Preferably, the organic layer includes a light emitting layer; the light-emitting layer comprises a host material and a doping material; the host material partially or completely comprises the heterocyclic organic photoelectric material.
In addition, the organic layer may further include other functional layers, and the other functional layers may be specifically selected from one or more of the following functional layers: a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a hole injection-hole transport functional layer (i.e., having both hole injection and hole transport functions), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and an electron transport-electron injection functional layer (i.e., having both electron transport and electron injection functions).
The kind of each functional layer is not particularly limited, and may be a conventional functional layer known to those skilled in the art.
The first electrode serves as an anode, which preferably comprises a material having a high work function. Such as Ag, Pt or Au. The preferred anode material is here a conductive mixed metal oxide. Particularly preferred is Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO). Preference is furthermore given to electrically conductive, doped organic materials, in particular electrically conductive, doped polymers. Since the lifetime of the device of the invention is shortened in the presence of water and/or air, the device is suitably (depending on the application) structured, provided with contacts and finally sealed.
The hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer, and has high hole mobility. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated portions and non-conjugated portions, and the like, but are not limited thereto.
The material of the light emitting layer is a material capable of emitting visible light by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the received holes and electrons.
Preferably, the mass ratio of the host material to the doping material is (90-99.5): (0.5-10).
The doping material may include fluorescent doping and phosphorescent doping.
The phosphorescent dopant material is a phosphorescent material including a metal complex of iridium, platinum, or the like. For example, Ir (ppy)3Equal green phosphorescent materials, FIrpic, FIr6, and Btp2Red color of Ir (acac)A chromatic phosphorescent material.
The electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, a material known in the art, for example, an arylamine-based organic material, may be used.
As the hole-blocking layer material, a compound having a hole-blocking effect known in the art, for example, a phenanthroline derivative such as Bathocuproine (BCP), an oxazole derivative, a triazole derivative, a triazine derivative, or the like can be used, but the invention is not limited thereto.
The electron transport layer may function to facilitate electron transport. The electron transport material is a material that favorably receives electrons from the cathode and transports the electrons to the light emitting layer, and a material having high electron mobility is suitable. As the electron transport layer material of the organic electroluminescent device of the present invention, compounds having an electron transport effect well known in the art, for example, Al complexes of 8-hydroxyquinoline; a complex comprising Alq 3; an organic radical compound; hydroxyflavone-metal complexes, and the like, but are not limited thereto.
The electron injection layer may function to promote electron injection. Has the ability of transporting electrons and prevents excitons generated in the light emitting layer from migrating to the hole injection layer. The electron injecting material used in the present invention includes fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like, but is not limited thereto.
The second electrode serves as a cathode, and a material having a small work function is generally preferred so that electrons are smoothly injected into the organic material layer. The method comprises the following steps: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO2Al, the layer thickness of this layer preferably being between 0.5 and 5 nm.
In the embodiment of the present invention, the various functional layers described above may be formed by a solution coating method and a vacuum deposition method. The solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, etc., but is not limited thereto.
The organic electroluminescent device may be an organic electroluminescent device, an organic solar cell, electronic paper, an organic photoreceptor, an organic thin film transistor, or the like, but is not limited thereto.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
according to the heterocyclic organic photoelectric material provided by the embodiment of the invention, a compound with a multi-element heterocyclic structure is used as a matrix, a specific group is introduced into the matrix structure, and the position of a substituent is regulated, so that the heterocyclic organic photoelectric material which has a high triplet state energy level, a good carrier mobility, high thermal stability and high film forming stability and can be matched with an adjacent energy level is obtained. The heterocyclic organic photoelectric material is applied to the field of organic electroluminescence, is used as a main material of a light-emitting layer, can reduce the driving voltage of a device, improves the light-emitting efficiency of the device and prolongs the service life of the device. In addition, the preparation method of the heterocyclic organic photoelectric material provided by the invention is simple in process, and the prepared product is high in purity.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
Example 1
The embodiment provides a heterocyclic organic photoelectric material, and the preparation method comprises the following steps:
Figure BDA0002933632740000211
weighing formula II-1 (20mmol, 6.60g), formula III-1 (24 mmol 1, 2.93g) and potassium carbonate (60mmol, 6.5g) into a reaction system under the protection of nitrogen, adding a mixed solution of 66mL of toluene, 33mL of anhydrous ethanol and 33mL of purified water, and adding catalyst Pd (PPh) under the protection of nitrogen3)4(0.4mmol, 0.46g) was refluxed for 15 hours, then cooled to room temperature, and precipitate was precipitatedAnd (4) discharging, filtering the precipitate, and washing and drying the precipitate by using water, absolute ethyl alcohol and petroleum ether in sequence. And (3) performing column chromatography (short column) on the dried product, and concentrating the filtrate until solid is separated out to obtain the heterocyclic organic photoelectric material shown as the formula I-1 (5.79g, the yield is 78%) with the HPLC purity of more than 99%.
Mass spectrum calculated 371.44 test 371.72.
Elemental analysis (%). calcd for C: 87.31; h is 4.61; n is 3.77; o is 4.31, and the test value is C is 87.30; h is 4.60; n is 3.79; o is 4.31.
Example 2
The embodiment provides a heterocyclic organic photoelectric material, and the preparation method comprises the following steps:
Figure BDA0002933632740000221
weighing formula II-22 (20mmol, 15.49g), formula III-22 (24 mmol 1, 2.93g) and potassium carbonate (60mmol, 6.5g) into a reaction system under the protection of nitrogen, adding a mixed solution of 150mL of toluene, 75mL of anhydrous ethanol and 75mL of purified water, and adding catalyst Pd (PPh) under the protection of nitrogen3)4(0.4mmol, 0.46g) is refluxed for 14 hours, then cooled to room temperature, precipitates are separated out, the precipitates are filtered by suction, and washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried. The dried product was subjected to column chromatography (short column), and the filtrate was concentrated to precipitate a solid, to obtain a heterocyclic organic photoelectric material represented by the formula I-22 (10.61g, yield 65%) having an HPLC purity of more than 99.5%.
Mass spectrum calculated 816.03 test 816.42.
Elemental analysis (%). calcd for C: 89.78; h is 4.57; n is 1.72; s:3.93, test value C: 89.79; h is 4.58; n is 1.72; and S: 3.91.
Example 3
The embodiment provides a heterocyclic organic photoelectric material, and the preparation method comprises the following steps:
Figure BDA0002933632740000222
weighing formula II-80 (20mmol, 13.64g), formula III-80 (26 mmol 1, 3.17g) and potassium carbonate (60mmol, 6.5g) into a reaction system under the protection of nitrogen, adding a mixed solution of 140mL of toluene, 70mL of anhydrous ethanol and 70mL of purified water, and adding catalyst Pd (PPh) under the protection of nitrogen3)4(0.4mmol, 0.46g) is refluxed for 13 hours, then cooled to room temperature, precipitates are separated out, the precipitates are filtered by suction, and washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried. The dried product was subjected to column chromatography (short column), and the filtrate was concentrated to precipitate a solid, to obtain a heterocyclic organic photoelectric material represented by the formula I-80 (8.54g, yield 59%) having an HPLC purity of more than 99.5%.
Mass spectrum calculated 723.88; the test value was 723.49.
Elemental analysis (%). calcd for C: 91.26; h is 4.60; n is 1.94; o is 2.21, and the test value is 91.25; h is 4.60; n is 1.96; o is 2.20.
Example 4
The embodiment provides a heterocyclic organic photoelectric material, and the preparation method comprises the following steps:
Figure BDA0002933632740000231
weighing formula II-85 (20mmol, 10.12g), formula III-85 (22 mmol 1, 5.46g) and potassium carbonate (60mmol, 6.5g) into a reaction system under the protection of nitrogen, adding a mixed solution of 100mL of toluene, 50mL of anhydrous ethanol and 50mL of purified water, and adding catalyst Pd (PPh) under the protection of nitrogen3)4(0.4mmol, 0.46g) is refluxed for 18 hours, then cooled to room temperature, precipitates are separated out, the precipitates are filtered by suction, and washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried. And (3) performing column chromatography (short column) on the dried product, and concentrating the filtrate until solid is separated out to obtain the heterocyclic organic photoelectric material shown as the formula I-85 (10.65g, the yield is 79%) with the HPLC purity of more than 99.5%.
Mass spectrum calculated 673.82; the test value was 673.46.
Elemental analysis (%). calcd C: 90.91; h is 4.64; 2.08 of N; o is 2.37, and the test value is C is 90.90; h is 4.65; 2.09 of N; o is 2.38.
Example 5
The embodiment provides a heterocyclic organic photoelectric material, and the preparation method comprises the following steps:
Figure BDA0002933632740000241
weighing formula II-113 (20mmol, 14.21g), formula III-54 (28 mmol 1, 14.07g) and potassium carbonate (60mmol, 6.5g) into a reaction system under the protection of nitrogen, adding a mixed solution of 140mL of toluene, 70mL of anhydrous ethanol and 70mL of purified water, and adding catalyst Pd (PPh) under the protection of nitrogen3)4(0.4mmol, 0.46g) is refluxed for 18 hours, then cooled to room temperature, precipitates are separated out, the precipitates are filtered by suction, and washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried. The dried product was subjected to column chromatography (short column) and the filtrate was concentrated to precipitate a solid, to obtain a heterocyclic organic photoelectric material represented by the formula I-113 (12.23g, yield 54%) having an HPLC purity of more than 99%.
Mass spectrum calculated 1132.42; the test value was 1132.68.
Elemental analysis (%). calcd for C: 92.28; h is 5.07; n is 1.24; o is 1.41, and the test value is C is 92.27; h is 5.06; n is 1.27; o is 1.40.
Examples 6 to 15
The preparation of heterocyclic organic photoelectric materials represented by the formulae I-5, I-32, I-40, I-48, I-54, I-63, I-72, I-92, I-104 and I-118, mass spectra and molecular formulae of which are shown in Table 1, was accomplished by the preparation methods described in reference to examples 1 to 5.
TABLE 1
Examples Compound (I) Molecular formula Calculated mass spectrum Mass spectrometric test values Yield (%)
Example 6 Formula I-5 C41H25NO 547.66 547.48 58
Example 7 Formula I-32 C33H19NS2 493.64 493.51 67
Example 8 Formula I-40 C47H27NO2 637.74 637.94 49
Example 9 Formula I-48 C55H33NO 723.88 723.49 52
Example 10 Formula I-54 C45H29N2O2P 660.71 660.54 61
Example 11 Formula I-63 C43H28N2O 588.71 588.46 64
Example 12 Formula I-72 C57H40N4O 796.97 796.82 48
Example 13 Formula I-92 C36H22N4O 526.60 526.34 47
Example 14 Formula I-104 C45H31N3S 645.82 645.96 56
Example 15 Formula I-118 C21D13NO 308.42 308.68 51
Example 6 Formula I-5 C41H25NO 547.66 547.48 58
The embodiment of the invention also provides an organic electroluminescent device prepared by adopting the heterocyclic organic photoelectric material provided by the embodiment, wherein the organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer arranged between the first electrode and the second electrode.
Wherein, the organic layer can comprise a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer, an electron injection layer, etc.; the organic light-emitting compounds provided in the above embodiments can be used as host materials in the light-emitting layer, and the dopant material of the light-emitting layer can be selected from compounds containing iridium, such as bis- (1-phenylisoquinolinyl) iridium (III) acetylacetonate, i.e., Ir (piq)2(acac)。
To further illustrate the present invention, more specific device embodiments are listed below.
Device example 1
The embodiment of the device provides an organic electroluminescent device, and the preparation method comprises the following steps:
s1, putting the ITO glass substrate with the coating thickness of 150nm into distilled water for cleaning for 2 times, ultrasonically cleaning for 30 minutes, repeatedly cleaning for 2 times by using the distilled water, ultrasonically cleaning for 10 minutes, after the cleaning by using the distilled water is finished, ultrasonically cleaning solvents such as isopropanol, acetone, methanol and the like in sequence, drying, transferring the substrates into a plasma cleaning machine, cleaning the substrates for 5 minutes, and sending the substrates into an evaporation machine.
S2, firstly, evaporating compound 2-TNATA on the ITO (anode) in vacuum to form a hole injection layer with the thickness of 55 nm; evaporating a compound NPB on the hole injection layer in vacuum to form a hole transport layer with the thickness of 35nm, wherein the evaporation rate is 0.1 nm/s; forming an electroluminescent layer on the hole transport layer, and specifically operating as follows: the heterocyclic organic photoelectric material represented by the formula I-1 provided in the embodiment of the present invention as a light emitting layer was placed in a cell of a vacuum vapor deposition apparatus, and Ir (piq) as a dopant was added2(acac) [ bis- (1-phenylisoquinolinyl) acetylacetonatoiridium (III)]Placing in another chamber of a vacuum vapor deposition apparatus, evaporating two materials at different rates simultaneously, Ir (piq)2The acac concentration is 6%, and the total film thickness of evaporation plating is 40 nm; depositing Bphen on the luminescent layer by vacuum evaporation to form an electron transport layer with the thickness of 20nm, wherein the evaporation rate is 0.1 nm/s; and (3) performing vacuum evaporation on the Electron Transport Layer (ETL) to form LiF with the thickness of 0.5nm as an electron injection layer, and performing vacuum evaporation on the Al layer with the thickness of 150nm as a cathode of the device on the electron injection layer to obtain the organic electroluminescent device.
Among them, the compound 2-TNATA, NPB, Ir (piq) used in the embodiments of the present invention2The structural formulae of acac and Bphen are as follows:
Figure BDA0002933632740000271
device example 2-device example 15
With reference to the preparation method provided in device example 1, the heterocyclic organic photoelectric material represented by formula I-1 used in device example 1 was replaced with the heterocyclic organic photoelectric material represented by formula I-5, formula I-22, formula I-32, formula I-40, formula I-48, formula I-54, formula I-63, formula I-72, formula I-80, formula I-85, formula I-92, formula I-104, formula I-113, formula I-118 provided in the above example, respectively, as a host material and a dopant material Ir (piq)2and performing mixed evaporation on the acac, and preparing the corresponding organic electroluminescent device.
Comparative device example 1
Comparative example of the device an organic electroluminescent device containing CBP was manufactured. Specifically, according to the preparation method of the device example 1, the heterocyclic organic photoelectric material shown in the formula I-1 and used in the device example 1 is replaced by CBP as a host material and a doping material Ir (piq)2and performing mixed evaporation on the acac, and preparing the corresponding organic electroluminescent device. Wherein, the structural formula of CBP is:
Figure BDA0002933632740000272
the organic electroluminescent devices obtained in the device examples 1 to 15 and the device comparative example 1 were characterized at a luminance of 2000(nits) for driving voltage, luminous efficiency and lifetime, and the results are shown in the following table 2:
TABLE 2
Figure BDA0002933632740000281
As can be seen from table 2, when the heterocyclic organic photoelectric material provided in the embodiment of the present invention is used as a host material of a light emitting layer of an organic electroluminescent device, compared with the conventional CBP used as a host material, the heterocyclic organic photoelectric material can significantly reduce the driving voltage of the organic electroluminescent device, and improve the light emitting efficiency, power efficiency and service life of the organic electroluminescent device.
The effect data of the heterocyclic organic photoelectric materials represented by the formulas 1-1, 1-5, 1-22, 1-32, 1-40, 1-48, 1-54, 1-63, 1-72, 1-80, 1-85, 1-92, 1-104, 1-113, and 1-118 listed in the above examples are representative sampling tests, and the overall data is not greatly different from the experimental data, and thus can represent the effects of other structures not listed.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.

Claims (10)

1. A heterocyclic organic photoelectric material is characterized in that the structural general formula of the heterocyclic organic photoelectric material is shown as formula I:
Figure FDA0002933632730000011
in the formula, R1、R2And R3Each independently selected from at least one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 6-to 30-membered aromatic heterocyclic group, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C5-C30 spiro ring; and R is1、R2And R3At any position of the ring in which they are located;
x is O or S, Y is N or P; m, n and p are all natural numbers.
2. The heterocyclic organic photoelectric material of claim 1, wherein X is O.
3. The heterocyclic organic photoelectric material of claim 1, wherein Y is N.
4. The heterocyclic organic photoelectric material according to claim 1, wherein m is a natural number of not more than 4.
5. The heterocyclic organic photoelectric material of claim 1, wherein n is a natural number not greater than 4.
6. The heterocyclic organic photoelectric material of claim 1, wherein p is a natural number not greater than 5.
7. The heterocyclic organic photoelectric material of claim 1, wherein the chemical structural formula of the heterocyclic organic photoelectric material is any one of formula I-1 to formula I-118:
Figure FDA0002933632730000021
Figure FDA0002933632730000031
Figure FDA0002933632730000041
Figure FDA0002933632730000051
Figure FDA0002933632730000061
Figure FDA0002933632730000071
Figure FDA0002933632730000081
Figure FDA0002933632730000091
Figure FDA0002933632730000101
Figure FDA0002933632730000111
Figure FDA0002933632730000121
Figure FDA0002933632730000131
Figure FDA0002933632730000141
Figure FDA0002933632730000151
Figure FDA0002933632730000161
8. a method for preparing the heterocyclic organic photoelectric material according to any one of claims 1 to 7, comprising the steps of:
Figure FDA0002933632730000171
under the protective atmosphere, mixing a compound shown as a formula II, a compound shown as a formula III, anhydrous potassium carbonate, toluene, anhydrous ethanol and water, and then adding tetrakis (triphenylphosphine) palladium to perform reflux reaction to obtain the heterocyclic organic photoelectric material; wherein Z represents a halogen.
9. An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer disposed between said first electrode and said second electrode, wherein said organic layer comprises a heterocyclic organic photoelectric material according to any one of claims 1 to 7.
10. An organic electroluminescent device according to claim 9, wherein the organic layer comprises a light-emitting layer; the light-emitting layer comprises a host material and a doping material; the host material partially or completely comprises the heterocyclic organic photoelectric material.
CN202110156296.6A 2021-02-04 2021-02-04 Heterocyclic organic photoelectric material, preparation method thereof and organic electroluminescent device Withdrawn CN112939890A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202110156296.6A CN112939890A (en) 2021-02-04 2021-02-04 Heterocyclic organic photoelectric material, preparation method thereof and organic electroluminescent device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202110156296.6A CN112939890A (en) 2021-02-04 2021-02-04 Heterocyclic organic photoelectric material, preparation method thereof and organic electroluminescent device

Publications (1)

Publication Number Publication Date
CN112939890A true CN112939890A (en) 2021-06-11

Family

ID=76243999

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202110156296.6A Withdrawn CN112939890A (en) 2021-02-04 2021-02-04 Heterocyclic organic photoelectric material, preparation method thereof and organic electroluminescent device

Country Status (1)

Country Link
CN (1) CN112939890A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021230681A1 (en) * 2020-05-13 2021-11-18 주식회사 엘지화학 Novel compound and organic light-emitting device using same
KR20210139184A (en) * 2020-05-13 2021-11-22 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
CN114621253A (en) * 2022-03-04 2022-06-14 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, and electronic element and electronic device using same
CN114716414A (en) * 2022-04-25 2022-07-08 吉林奥来德光电材料股份有限公司 Organic electroluminescent material, preparation method thereof and organic electroluminescent device comprising organic electroluminescent material
WO2022160928A1 (en) * 2021-01-28 2022-08-04 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, and electronic component and electronic device containing same

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001023777A (en) * 1999-07-08 2001-01-26 Toray Ind Inc Luminescent element
KR20090058564A (en) * 2006-09-14 2009-06-09 시바 홀딩 인크 Heterocyclic bridged biphenyls and their use in oleds
CN101687814A (en) * 2007-03-29 2010-03-31 巴斯夫欧洲公司 heterocyclic bridged biphenyls
WO2011102586A1 (en) * 2010-02-22 2011-08-25 제일모직 주식회사 Compound for an organic photoelectric device and photoelectric device including same
WO2012091225A1 (en) * 2010-12-31 2012-07-05 제일모직 주식회사 Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including organic light emitting diode
WO2013162148A1 (en) * 2012-04-24 2013-10-31 제일모직 주식회사 Compound for organic optoelectric device, organic light emitting device containing same, and display device containing said organic light emitting device
US20180208837A1 (en) * 2015-08-19 2018-07-26 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compounds and organic electroluminescent device comprising the same
CN110291075A (en) * 2017-02-27 2019-09-27 罗门哈斯电子材料韩国有限公司 A variety of material of main parts and Organnic electroluminescent device comprising it

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001023777A (en) * 1999-07-08 2001-01-26 Toray Ind Inc Luminescent element
KR20090058564A (en) * 2006-09-14 2009-06-09 시바 홀딩 인크 Heterocyclic bridged biphenyls and their use in oleds
CN101687814A (en) * 2007-03-29 2010-03-31 巴斯夫欧洲公司 heterocyclic bridged biphenyls
WO2011102586A1 (en) * 2010-02-22 2011-08-25 제일모직 주식회사 Compound for an organic photoelectric device and photoelectric device including same
WO2012091225A1 (en) * 2010-12-31 2012-07-05 제일모직 주식회사 Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including organic light emitting diode
WO2013162148A1 (en) * 2012-04-24 2013-10-31 제일모직 주식회사 Compound for organic optoelectric device, organic light emitting device containing same, and display device containing said organic light emitting device
US20180208837A1 (en) * 2015-08-19 2018-07-26 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compounds and organic electroluminescent device comprising the same
CN110291075A (en) * 2017-02-27 2019-09-27 罗门哈斯电子材料韩国有限公司 A variety of material of main parts and Organnic electroluminescent device comprising it

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KANG SEOKWOO，等: "New bipolar host materials using Phenanthro[9,10-d]oxazole moiety for highly efficient red phosphorescence", 《DYES AND PIGMENTS》 *
彭骞，等: "有机电致发光（OLED）材料的研究进展", 《材料导报》 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021230681A1 (en) * 2020-05-13 2021-11-18 주식회사 엘지화학 Novel compound and organic light-emitting device using same
KR20210139184A (en) * 2020-05-13 2021-11-22 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
KR102546619B1 (en) 2020-05-13 2023-06-22 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same
WO2022160928A1 (en) * 2021-01-28 2022-08-04 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, and electronic component and electronic device containing same
CN114621253A (en) * 2022-03-04 2022-06-14 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, and electronic element and electronic device using same
CN114621253B (en) * 2022-03-04 2023-06-13 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, and electronic component and electronic device using same
CN114716414A (en) * 2022-04-25 2022-07-08 吉林奥来德光电材料股份有限公司 Organic electroluminescent material, preparation method thereof and organic electroluminescent device comprising organic electroluminescent material

Similar Documents

Publication Publication Date Title
US8703303B2 (en) Organic electroluminescent device having a light-emitting layer comprising a host material of two or more compounds
EP2541635B1 (en) Organic electroluminescent element
EP2715825B1 (en) Oled having multi-component emissive layer
CN112939890A (en) Heterocyclic organic photoelectric material, preparation method thereof and organic electroluminescent device
CN113024529B (en) Organic electroluminescent material and organic electroluminescent device
US20190322623A1 (en) Compound, display panel, and display apparatus
CN109553569B (en) Compound, display panel and display device
CN108250214B (en) Oxaspirofluorene triphenylamine derivative, preparation method and application thereof
CN112375071B (en) Organic light-emitting compound and preparation method and application thereof
CN112979536A (en) Phosphorescent main body material, preparation method thereof and organic electroluminescent device
CN111785841B (en) Organic electroluminescent device and application thereof
KR20160047297A (en) Organic electro luminescence device
CN113135945A (en) Organic boron semiconductor material and OLED device application
CN112939990B (en) Luminescent compound with organic condensed rings, preparation method thereof and organic electroluminescent device
CN112480077B (en) Compound for organic luminescence and application thereof
EP3915982B1 (en) Compound and organic light-emitting device including same
CN113045577A (en) Electron transport material, preparation method thereof, organic electroluminescent device and display device
CN108586539B (en) Dibenzothiophene ring-containing metal iridium complex and application thereof as luminescent layer doping material of organic electroluminescent device
CN112940008B (en) Organic electroluminescent material, preparation method thereof and organic electroluminescent device
KR20190117376A (en) Hole transporting material and Organic electroluminescent display device using the same
CN112661701B (en) Pterenes electron transport material, preparation method thereof and organic electroluminescent device
EP4169085B1 (en) Organic compound of formula (i) for use in organic electronic devices, an organic electronic device comprising a compound of formula (i) and a display device comprising the organic electronic device
CN112661752B (en) Phenanthroimidazole condensed ring compound, preparation method thereof and organic electroluminescent device
EP3930024B1 (en) Organic electronic device and display device comprising the organic electronic device as well as a composition for use in organic electronic devices
CN112079875B (en) Organic electroluminescent material, preparation method thereof and 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
WW01 Invention patent application withdrawn after publication
WW01 Invention patent application withdrawn after publication

Application publication date: 20210611