CN110041268B - Pyrimidine bipolar compound and application thereof in OLED (organic light emitting diode) device - Google Patents

Pyrimidine bipolar compound and application thereof in OLED (organic light emitting diode) device Download PDF

Info

Publication number
CN110041268B
CN110041268B CN201910414853.2A CN201910414853A CN110041268B CN 110041268 B CN110041268 B CN 110041268B CN 201910414853 A CN201910414853 A CN 201910414853A CN 110041268 B CN110041268 B CN 110041268B
Authority
CN
China
Prior art keywords
compound
pyrimidine
oled
substituted
formula
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.)
Active
Application number
CN201910414853.2A
Other languages
Chinese (zh)
Other versions
CN110041268A (en
Inventor
刘凯鹏
孙军
张宏科
田密
杨丹丹
何海晓
李江楠
王小伟
刘骞峰
高仁孝
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.)
Xi'an Manareco New Materials Co ltd
Original Assignee
Xi'an Manareco New 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 Xi'an Manareco New Materials Co ltd filed Critical Xi'an Manareco New Materials Co ltd
Priority to CN201910414853.2A priority Critical patent/CN110041268B/en
Publication of CN110041268A publication Critical patent/CN110041268A/en
Application granted granted Critical
Publication of CN110041268B publication Critical patent/CN110041268B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D403/02—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 two hetero rings
    • C07D403/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D403/02—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 two hetero rings
    • C07D403/10—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 two hetero rings linked by a carbon chain containing aromatic 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • 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
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Landscapes

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

Abstract

The invention discloses a pyrimidine bipolar compound and application thereof in an OLED device, belonging to the technical field of organic electroluminescent materials, and the structural general formula is shown as the following formula (I): wherein L is phenylene or substituted phenylene, and m and n are any integer between 0 and 2; d 1 、D 2 Each independently is an electron donating group; the pyrimidine bipolar compound provided by the invention has a donor-acceptor-donor structure, has balanced charge transfer performance and a higher triplet state energy level, is not easy to crystallize, and has good thermal stability and film-forming property; the compound provided by the invention is used as a main body material and a doping material to be applied to an OLED device, so that the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.
Figure DDA0002064007090000011

Description

Pyrimidine bipolar compound and application thereof in OLED (organic light emitting diode) device
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a pyrimidine bipolar compound and application thereof in an OLED (organic light emitting diode) device.
Background
The basic structure of an Organic Light Emission Diode (OLED) is a sandwich structure formed by a thin and transparent Indium Tin Oxide (ITO) with semiconductor properties connected to an anode and another metal cathode. The entire structure layer includes a Hole Transport Layer (HTL), an Emission Layer (EL), and an Electron Transport Layer (ETL). When power is supplied to a suitable voltage, positive holes and cathode charges combine in the light-emitting layer, producing light.
The OLED display technology has the advantages of self-luminescence, wide viewing angle, low energy consumption, high reaction speed and the like, and the technology enables a portable highly-foldable display screen to be possible, so that the OLED display technology is widely applied to the fields of mobile phones, digital video cameras, notebook computers, televisions, automobiles and the like. However, compared with the requirements of products in practical application, there is a certain gap in performance, especially, the luminous efficiency and the lifetime are still required to be further improved. The improvement is mainly carried out from two aspects: the optimization and innovation of the device structure, and the research and development of high-performance functional materials.
In order to fabricate high-performance OLED light-emitting devices, researchers have continuously proposed new light-emitting mechanisms and functional materials in recent years. The qieyong project group at Qinghua university in 2014 proposed a thermal activation sensitized light emitting mechanism, which uses a Thermal Activity Delayed Fluorescence (TADF) material as a host material of an OLED device, and the TADF material sensitizes a traditional fluorescence/phosphorescence material to improve the performance of the device. Almost at the same time, the Adachi topic group at kyushu university, japan also proposes a similar light emission mechanism. With the continuous research on this type of material, researchers are continuously designing new OLED functional materials, but no TADF host material with excellent performance and capable of meeting the requirements of mass production is available at present. The focus of such TADF material design development is to balance the charge transport properties of the material and maintain high charge mobility and triplet energy levels.
According to the industrial application requirements of the current OLED device, in order to meet the photoelectric characteristic requirements of the device, an OLED functional material or a material combination with high performance needs to be selected, and the comprehensive characteristics of high efficiency, long service life and low voltage of the device can be realized. The development of the OLED materials at present is still significantly behind the requirements of panel manufacturing enterprises and the requirements of practical applications, and the development of organic functional materials with higher performance is more important and urgent in the presence of the current market demands.
Disclosure of Invention
The invention provides a pyrimidine bipolar compound which is applied to an organic electroluminescent device as a luminescent layer material and can obviously improve the device performance of the organic electroluminescent device.
The first purpose of the invention is to provide a pyrimidine bipolar compound, the structural general formula of which is shown as the following formula (I):
Figure BDA0002064007070000021
wherein L is a phenylene group or a substituted phenylene group, and when L is a substituted phenylene group, these substituents are a hydrogen atom, a halogen, an alkyl group of C1 to C6, a cyano group, a phenyl group, a biphenyl group, a 4-pyridyl group and a trifluoromethyl group; m and n are any integer between 0 and 2;
D 1 、D 2 are each an electron donating group, D 1 、D 2 Are independently selected from the group consisting of formula (II), formula (III), formula (IV), formula (V) and formula (VI):
Figure BDA0002064007070000031
in the formula (II), Ar 1 、Ar 2 Each independently selected from any one of substituted or unsubstituted aryl or condensed ring aryl of C6-C30, substituted or unsubstituted condensed heterocyclic group of C6-C30, five-membered heterocyclic ring, six-membered heterocyclic ring or substituted heterocyclic ring, and substituted or unsubstituted amino;
in the formula (III), R 1 、R 2 Respectively and independently selected from any one of hydrogen atoms, alkyl groups of C1-C6, alkoxy groups of C1-C6, substituted or unsubstituted aryl or condensed ring aryl of C6-C30, substituted or unsubstituted condensed heterocyclic groups of C6-C30 and substituted or unsubstituted amino groups;
x in the formula (IV) 1 And X 2 X in the formula (V) 3 And X in the formula (VI) 4 Are all oxygen atom, sulfur atom, C-m 1 m 2 Or N-m 3 ；
Wherein m is 1 、m 2 Are respectively and independently selected from hydrogen atoms, alkyl groups of C1-C6, phenyl or biphenyl;
m 3 is any one of substituted or unsubstituted aryl or condensed ring aryl of C6-C30 and substituted or unsubstituted condensed heterocyclic group of C6-C30.
Preferably, the formula (II) is selected from one of the following structural formulae:
Figure BDA0002064007070000041
preferably, the formula (iii) is selected from one of the following structural formulae:
Figure BDA0002064007070000042
preferably, the (iv) is selected from one of the following structural formulae:
Figure BDA0002064007070000043
Figure BDA0002064007070000051
preferably, said (v) is selected from one of the following structural formulae:
Figure BDA0002064007070000052
preferably, the formula (vi) is selected from one of the following structural formulae:
Figure BDA0002064007070000053
preferably, the pyrimidine bipolar compound is specifically one of the following compounds:
Figure BDA0002064007070000054
Figure BDA0002064007070000061
Figure BDA0002064007070000071
Figure BDA0002064007070000081
the second purpose of the invention is to provide the application of the pyrimidine bipolar compound in an organic electroluminescent device.
The third object of the present invention is to provide an organic electroluminescent device comprising a light-emitting layer, wherein the material of the light-emitting layer comprises the above pyrimidine bipolar compound.
A fourth object of the present invention is to provide an application of the above organic electroluminescent device in an organic electroluminescent display device.
Compared with the prior art, the pyrimidine bipolar compound has the following beneficial effects that the pyrimidine bipolar compound has a donor-acceptor-donor structure, has balanced charge transmission performance and higher triplet state energy level, is not easy to crystallize, and has good thermal stability and film forming property; the compound provided by the invention is used as a main material and a doping material to be applied to an OLED device, and can effectively improve the luminous efficiency and prolong the service life of the device.
Drawings
Fig. 1 is a schematic structural diagram of an organic electroluminescent device provided in an embodiment of the present invention.
Description of reference numerals:
1. the cathode layer comprises a substrate, 2, an anode layer, 3, a hole transport layer, 4, a light emitting layer, 5, an electron transport layer, 6, an electron injection layer, 7 and a cathode layer.
Detailed Description
In order to make the technical solutions of the present invention better understood and enable one skilled in the art to practice the present invention, the present invention is further described below with reference to specific examples and drawings, but the examples are not intended to limit the present invention.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
The general structural formula of the pyrimidine bipolar compound provided by the invention is shown as the following formula (I):
Figure BDA0002064007070000091
wherein L is a phenylene group or a substituted phenylene group, and when L is a substituted phenylene group, these substituents are a hydrogen atom, a halogen, an alkyl group of C1 to C6, a cyano group, a phenyl group, a biphenyl group, a 4-pyridyl group and a trifluoromethyl group; m and n are any integer between 0 and 2;
D 1 、D 2 are each an electron donating group, D 1 、D 2 Are independently selected from the group consisting of formula (II), formula (III), formula (IV), formula (V) and formula (VI):
Figure BDA0002064007070000092
in the formula (II), Ar 1 、Ar 2 Each independently selected from any one of substituted or unsubstituted aryl or condensed ring aryl of C6-C30, substituted or unsubstituted condensed heterocyclic group of C6-C30, five-membered heterocyclic ring, six-membered heterocyclic ring or substituted heterocyclic ring, and substituted or unsubstituted amino;
in the formula (III), R 1 、R 2 Independently selected from any one of hydrogen atoms, alkyl groups of C1-C6, alkoxy groups of C1-C6, substituted or unsubstituted aryl or fused ring aryl of C6-C30, substituted or unsubstituted fused heterocyclic groups of C6-C30 and substituted or unsubstituted amino groups;
x in the formula (IV) 1 And X 2 X in the formula (V) 3 And X in the formula (VI) 4 Are all oxygen atom, sulfur atom, C-m 1 m 2 Or N-m 3 ；
Wherein m is 1 、m 2 Are respectively and independently selected from hydrogen atoms, alkyl groups of C1-C6, phenyl or biphenyl;
m 3 is substituted or unsubstituted aryl or condensed ring aryl of C6-C30, substituted or unsubstituted of C6-C30Any one of substituted fused heterocyclic groups.
According to the pyrimidine bipolar compound provided by the invention, a pyrimidine group is used as an acceptor (A) and is connected with two electron donors (D) with different structures to obtain the D-A-D bipolar compound, and the D-A-D bipolar compound can be used as a doping material or a main material of an organic electroluminescent diode to realize high brightness, low voltage, high efficiency and long service life of an organic Electroluminescent (EL) element. The material has smaller singlet state energy and triplet state energy difference (delta Est), can realize the reversal from triplet state energy to singlet state energy, and has thermal activity time delay fluorescence property (TADF). The pyrimidine bipolar compound shows excellent properties when being used as a main material, on one hand, the bipolar characteristic effectively enriches holes and electrons in a light-emitting layer, increases an exciton recombination zone, effectively improves the efficiency and the service life of a device, and reduces the attenuation of the efficiency; on the other hand, the TADF material can effectively sensitize the luminescent material as a main body material with TADF property, effectively improve the efficiency and the service life of the device, optimize the spectrum of the TADF material and improve the color purity of the TADF device.
In the following, we specifically take part in the example of pyrimidine bipolar compounds, and provide the synthesis method of the compounds of the present invention; the following intermediates 1-1, 1-2, 1-4, 2-1, 2-3, 6-1 and 6-3 were all synthesized according to the existing methods.
Example 1
(1) Synthesis of intermediates 1 to 3:
Figure BDA0002064007070000111
30g of intermediate 1-1, 19.6g of intermediate 1-2, 13.9g of potassium carbonate, 1.1g of tetrabutylammonium bromide, 300ml of toluene, 200ml of ethanol and 100ml of water are added into a 1L three-necked bottle, nitrogen is introduced to remove air in the system, 0.39g of tetrakis (triphenylphosphine) palladium is added, the temperature is increased to 80 ℃, the reaction is stirred and reacted for 6 hours, the temperature is reduced to room temperature for liquid separation, an organic phase is washed to be neutral by water, the organic phase passes through a column after being dried by anhydrous sodium sulfate, toluene is recrystallized to obtain 28.0g of intermediate 1-3 totally, and the yield is 87.2%.
Nuclear magnetic spectrum data of intermediates 1 to 3: 1 H NMR(400MHz,CDCl 3 )δ8.80(s,2H),7.71(s,1H),7.54(d,J＝7.6,4H),7.48-7.50(m,2H),7.41-7.43(m,6H),7.19(t,J＝7.6,1H),7.13(t,J＝7.6,1H)。
(2) synthesis of Compound 1:
Figure BDA0002064007070000112
adding 25g of intermediate 1-3, 15.4g of intermediate 1-4, 10.9g of potassium carbonate, 0.85g of tetrabutylammonium bromide, 300ml of toluene, 200ml of ethanol and 100ml of water into a 1L three-necked bottle, introducing nitrogen to remove air in the system, adding 0.30g of tetrakis (triphenylphosphine) palladium, heating to 80 ℃, stirring for reaction for 10 hours, cooling to room temperature for liquid separation, washing an organic phase to be neutral, drying with anhydrous sodium sulfate, passing through a column, and recrystallizing with toluene to obtain 24.1g of the compound 1 totally, wherein the yield is 81.6%.
Nuclear magnetic spectrum data of compound 1: 1 H NMR(400MHz,CDCl 3 )δ8.80(s,2H),7.71(s,1H),7.54(d,J＝7.6,4H),7.48-7.50(m,2H),7.41-7.43(m,2H),7.19(t,J＝7.6,1H),7.13(t,J＝7.6,1H)。
example 2
(1) Synthesis of intermediate 2-2:
Figure BDA0002064007070000121
30g of intermediate 2-1, 23.5g of intermediate 1-2, 16.8g of potassium carbonate, 1.3g of tetrabutylammonium bromide, 300ml of toluene, 200ml of ethanol and 100ml of water are added into a 1L three-necked bottle, nitrogen is introduced to remove air in the system, 0.47g of tetrakis (triphenylphosphine) palladium is added, the temperature is increased to 80 ℃, the mixture is stirred and reacted for 6 hours, the mixture is cooled to room temperature for liquid separation, an organic phase is washed to be neutral by water, the organic phase passes through a column after being dried by anhydrous sodium sulfate, toluene is recrystallized to obtain 27.2g of intermediate 2-2 altogether, and the yield is 83.7%.
Nuclear magnetic spectrum data of intermediate 2-2: 1 H NMR(400MHz,CDCl 3 )δ8.80(s,2H),7.71(s,1H),7.54(d,J＝7.6,4H),7.48-7.50(m,2H),7.41-7.43(m,6H),7.19(t,J＝7.6,1H),7.13(t,J＝7.6,1H)。
(2) synthesis of Compound 2:
Figure BDA0002064007070000122
adding 25g of intermediate 2-2, 23.0g of intermediate 2-3, 12.9g of potassium carbonate, 1.0g of tetrabutylammonium bromide, 300ml of toluene, 200ml of ethanol and 100ml of water into a 1L three-necked bottle, introducing nitrogen to remove air in the system, adding 0.36g of tetrakis (triphenylphosphine) palladium, heating to 80 ℃, stirring for reaction for 8 hours, cooling to room temperature for liquid separation, washing an organic phase to be neutral, drying with anhydrous sodium sulfate, passing through a column, and recrystallizing with toluene to obtain 27.0g of compound 2 in total, wherein the yield is 76.8%.
Nuclear magnetic spectroscopy data for compound 2: 1 H NMR(400MHz,CDCl 3 )δ8.84(s,2H),7.77(s,1H),7.71(s,1H),7.54(s,5H),7.46-7.49(m,3H),7.40-7.42(m,3H),7.30-7.35(m,6H),7.19(t,J＝7.6,1H),7.13(t,J＝7.6,1H),7.08(t,J＝7.6,1H),7.00(t,J＝7.6,1H)。
example 3
(1) Synthesis of intermediate 6-2:
Figure BDA0002064007070000131
30g of intermediate 6-1, 16.7g of intermediate 1-2, 11.9g of potassium carbonate, 0.93g of tetrabutylammonium bromide, 300ml of toluene, 200ml of ethanol and 100ml of water are added into a 1L three-necked bottle, nitrogen is introduced to remove air in the system, 0.33g of tetrakis (triphenylphosphine) palladium is added, the temperature is increased to 80 ℃, the reaction is stirred for 6 hours, the temperature is reduced to room temperature for liquid separation, an organic phase is washed to be neutral, dried by anhydrous sodium sulfate, then the organic phase passes through a column, and toluene is recrystallized to obtain 25.3g of intermediate 6-2 totally, and the yield is 79.6%.
Nuclear magnetic spectrum data of intermediate 6-2: 1 H NMR(400MHz,CDCl 3 )δ8.80(s,2H),7.90(d,J＝7.2,1H),7.84(d,J＝7.6,1H),7.77(s,1H),7.54-7.60(m,6H),7.38(t,J＝7.6,1H),7.28(t,J＝7.6,1H),7.14(t,J＝7.6,4H),7.05-7.08(m,6H)。
(2) synthesis of Compound 6:
Figure BDA0002064007070000132
adding 25g of intermediate 6-2, 22.0g of intermediate 6-3, 9.4g of potassium carbonate, 0.73g of tetrabutylammonium bromide, 300ml of toluene, 200ml of ethanol and 100ml of water into a 1L three-necked bottle, introducing nitrogen to remove air in the system, adding 0.26g of tetrakis (triphenylphosphine) palladium, heating to 80 ℃, stirring for reaction for 8 hours, cooling to room temperature for liquid separation, washing an organic phase to be neutral, drying with anhydrous sodium sulfate, passing through a column, and recrystallizing with toluene to obtain 27.3g of compound 6 in total, wherein the yield is 72.6%.
Nuclear magnetic spectrum data of compound 6: 1 H NMR(400MHz,CDCl 3 )δ8.84(s,2H),8.06(d,J＝7.2,1H),7.90(d,J＝7.2,1H),7.84(d,J＝7.6,1H),7.77(s,2H),7.69(m,1H),7.54-7.61(m,7H),7.44-7.46(m,2H),7.24-7.38(m,10H),7.14(t,J＝7.6,4H),7.05-7.08(m,6H),1.67(s,6H)。
the following tests were performed on some of the compounds provided by the present invention and the thermal and orbital level parameters of the existing materials, and the results are shown in table 1:
TABLE 1 thermal and orbital energy level parameters for compounds of the invention and prior materials
Figure BDA0002064007070000141
Note: the thermogravimetric temperature Td is a temperature at which 1% weight loss occurs in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 ml/min; the Tg temperature was measured on a DSC-60 differential scanning calorimeter from Shimadzu corporation, Japan, and the nitrogen flow was 10 ml/min; HOMO/LUOMO energy level is data obtained by simulation calculation in Gaussian 09 software, and the calculation method adopts a B3LYP hybridization functional, and the group is 6-31g (d).
The data in table 1 show that the compound provided by the invention has higher thermal stability, so that the compound has better film-forming property, and the service life of the prepared OLED device containing the compound is prolonged; the compounds of the invention also have different HOMO energy levels and can be applied to different functional layers.
In the following, some of the compounds provided by the present invention are taken as examples, and applied to an organic electroluminescent device as a luminescent layer material (host material and/or dopant material) to verify the excellent effects achieved by the compounds.
Specifically, the excellent effect of the OLED material applied to the device is detailed through the device performances of device examples 1-12 and comparative examples 1 and 2. The structure manufacturing processes of the devices of examples 1 to 12 of the invention are completely the same as those of comparative examples 1 and 2, and the same glass substrate and electrode material are adopted, the thickness of the electrode material film is kept consistent, and the difference is that the material of the luminescent layer is adjusted, which is as follows.
Device application example
Device example 1
The present embodiment provides an organic electroluminescent device, which has a structure as shown in fig. 1, and includes a substrate 1, an anode layer 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, an electron injection layer 6, and a cathode layer 7, which are sequentially stacked.
Wherein, the anode layer 2 material is selected from Indium Tin Oxide (ITO) with high common function; TAPC is selected as the material of the hole transport layer 3, and the thickness is 80 nm; the light-emitting layer 4 uses the compound 1 as a Host (Host) material, Ir (mphmq) 2 (tmd) as a Dopant (Dopant) material, with a Dopant amount ratio of 2%, with a thickness of 30 nm; TPBI is selected as the material of the electron transport layer 5, and the thickness is 40 nm; the material of the electron injection layer 6 is lithium fluoride with the thickness of 1 nm; the cathode layer is made of Al and has a thickness of 80 nm.
The structural formula of the basic material used by each functional layer in the device is as follows:
Figure BDA0002064007070000151
Figure BDA0002064007070000161
the organic electroluminescent device is prepared by the following specific steps:
(1) the transparent substrate layer is a transparent substrate, such as a transparent PI film, glass and the like, the ITO anode layer on the transparent substrate is washed, alkali washing, ultrapure water washing and drying are sequentially carried out, and then ultraviolet-ozone washing is carried out to remove organic residues on the surface of the transparent ITO;
(2) depositing TAPC with a thickness of 80nm as a hole transport layer on the ITO anode layer by using a vacuum deposition apparatus;
(3) after the completion of the evaporation of the hole transport material, a light-emitting layer of an OLED light-emitting device was fabricated by using Compound 1 as the Host material and Ir (mphmq) 2 (tmd) is a Dopant material, the doping ratio of the Dopant material is 2% by weight, and the thickness of the luminescent layer is 30 nm;
(4) continuing vacuum evaporation of an electron transport material TPBI as an electron transport layer with the thickness of 40nm after the light-emitting layer;
(5) on the electron transport layer, a lithium fluoride layer with the film thickness of 1nm is manufactured by vacuum evaporation to be used as an electron injection layer;
(6) on the electron injection layer, an aluminum layer having a film thickness of 80nm was formed as a cathode electrode layer by vacuum evaporation.
After the OLED device is manufactured, the anode and the cathode are connected by a driving circuit, and the current efficiency, the luminous brightness and the service life of the device are measured.
Device example 2
Same as device example 1, except that: compound 2 was substituted for compound 1 as the Host material.
Device example 3
Same as device example 1, except that: compound 3 was used as Host material instead of compound 1.
Device example 4
Same as device example 1, except that: compound 4 was substituted for compound 1 as the Host material.
Device example 5
Same as device example 1, except that: compound 8 was substituted for compound 1 as the Host material.
Device example 6
Same as device example 1, except that: compound 9 was substituted for compound 1 as the Host material.
Device example 7
Same as device example 1, except that: compound 10 was substituted for compound 1 as the Host material.
Device example 8
Same as device example 1, except that: compound 29 was substituted for compound 1 as the Host material.
Device example 9
Same as device example 1, except that: replacement of Compound 1 with CBP as Host Material and Ir (mphmq) with Compound 38 as Dopant Material 2 (tmd)。
Device example 10
Same as device example 9, except that: compound 39 was substituted for compound 38 as the Dopant material.
Device example 11
Same as device example 9, except that: compound 50 was substituted for compound 38 as the Dopant material.
Device example 12
Same as device example 9, except that: compound 51 was substituted for compound 38 as the Dopant material.
Comparative example 1
Same as device example 9, except that: mixing Ir (mphmq) 2 (tmd) as a Dopant material in place of compound 38.
Comparative example 2
Same as device example 9, except that: DPAVBi was substituted for compound 38 as the Dopant material.
In the embodiments 1 to 12, the synthesized compound is used as the main material of the light emitting layer and the doping material of the light emitting layer in the OLED device, compared with the comparative example, the manufacturing processes of the devices in the embodiments 1 to 12 are completely the same, the adopted substrate material and the adopted electrode material are also completely the same, the film thickness of the electrode material is also kept consistent, and the device performance testing method is the same as the comparative example. The test results of the resulting devices are shown in table 2:
table 2 performance results for each group of organic electroluminescent devices
Figure BDA0002064007070000181
Figure BDA0002064007070000191
Note: the half life test in the table is that the device is 1000cd/m 2 Decay time at brightness.
As can be seen from the data in Table 2, compared with a device using the existing material CBP as a Host material, in device embodiments 1 to 8, after the compound is used as a Host material, the driving voltage of the device is reduced by about 25%, the half life is prolonged by about 85%, and the current efficiency and the light-emitting brightness are both improved, so that the material can be applied to an OLED device as the Host material to improve the performance of the device; in addition, compared with a device using the existing material DPAVBi as the dock material, after the material is used as the dock material in device examples 9-12, the driving voltage of the device is reduced by about 25%, the half life is improved by about 2 times, and the current efficiency and the light-emitting brightness are improved, so that the material can be applied to an OLED device as the dock material to improve the performance of the device.
Compared with the existing materials, the material of the invention can greatly improve the performance of the device when being applied to OLED devices, especially Host materials and company materials, and is a novel organic OLED functional material with a development prospect.
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, it is intended that such changes and modifications be included within the scope of the present invention as set forth in the appended claims and their equivalents.

Claims (4)

1. The pyrimidine bipolar compound is characterized by being specifically one of the following compounds:
Figure FDA0003765500520000011
2. use of the pyrimidine bipolar compound according to claim 1 in an organic electroluminescent device.
3. An organic electroluminescent device comprising a light-emitting layer, characterized in that the light-emitting layer material comprises the pyrimidine bipolar compound according to claim 1.
4. Use of the organic electroluminescent device as claimed in claim 3 in an organic electroluminescent display device.
CN201910414853.2A 2019-05-17 2019-05-17 Pyrimidine bipolar compound and application thereof in OLED (organic light emitting diode) device Active CN110041268B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910414853.2A CN110041268B (en) 2019-05-17 2019-05-17 Pyrimidine bipolar compound and application thereof in OLED (organic light emitting diode) device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910414853.2A CN110041268B (en) 2019-05-17 2019-05-17 Pyrimidine bipolar compound and application thereof in OLED (organic light emitting diode) device

Publications (2)

Publication Number Publication Date
CN110041268A CN110041268A (en) 2019-07-23
CN110041268B true CN110041268B (en) 2022-09-30

Family

ID=67282673

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910414853.2A Active CN110041268B (en) 2019-05-17 2019-05-17 Pyrimidine bipolar compound and application thereof in OLED (organic light emitting diode) device

Country Status (1)

Country Link
CN (1) CN110041268B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220033736A (en) * 2020-09-10 2022-03-17 엘지디스플레이 주식회사 Organic compounds having improved luminsecent properties, organic light emitting diode and organic light emitting device including the compounds
CN114605392B (en) * 2022-02-23 2024-04-02 烟台京师材料基因组工程研究院 Compound and ultraviolet absorber and application thereof
CN114671857B (en) * 2022-03-07 2024-02-09 宁波卢米蓝新材料有限公司 Organic compound and application thereof in organic electroluminescent device

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103155201A (en) * 2011-08-25 2013-06-12 株式会社半导体能源研究所 Light-emitting element, light-emitting device, electronic device, lighting device, and novel organic compound
WO2013157886A1 (en) * 2012-04-19 2013-10-24 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20140027030A (en) * 2012-08-23 2014-03-06 (주)씨에스엘쏠라 Organic light compound and organic light device using the same
CN106469790A (en) * 2015-08-21 2017-03-01 三星显示有限公司 Organic light emitting apparatus
CN108864054A (en) * 2018-07-26 2018-11-23 上海天马有机发光显示技术有限公司 A kind of nitrogen heterocyclic and organic light-emitting display device
WO2019083248A1 (en) * 2017-10-27 2019-05-02 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
CN110117276A (en) * 2018-02-05 2019-08-13 北京鼎材科技有限公司 Organic compound and its application in organic electroluminescence device
CN113661582A (en) * 2019-04-26 2021-11-16 罗门哈斯电子材料韩国有限公司 Multiple host materials and organic electroluminescent device comprising the same

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103155201A (en) * 2011-08-25 2013-06-12 株式会社半导体能源研究所 Light-emitting element, light-emitting device, electronic device, lighting device, and novel organic compound
WO2013157886A1 (en) * 2012-04-19 2013-10-24 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20140027030A (en) * 2012-08-23 2014-03-06 (주)씨에스엘쏠라 Organic light compound and organic light device using the same
CN106469790A (en) * 2015-08-21 2017-03-01 三星显示有限公司 Organic light emitting apparatus
WO2019083248A1 (en) * 2017-10-27 2019-05-02 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
CN110117276A (en) * 2018-02-05 2019-08-13 北京鼎材科技有限公司 Organic compound and its application in organic electroluminescence device
CN108864054A (en) * 2018-07-26 2018-11-23 上海天马有机发光显示技术有限公司 A kind of nitrogen heterocyclic and organic light-emitting display device
CN113661582A (en) * 2019-04-26 2021-11-16 罗门哈斯电子材料韩国有限公司 Multiple host materials and organic electroluminescent device comprising the same

Also Published As

Publication number Publication date
CN110041268A (en) 2019-07-23

Similar Documents

Publication Publication Date Title
US20160260907A1 (en) Organic electroluminescent material and organic electroluminescent device
CN109535131B (en) Compound taking cyanopyridine as receptor and application thereof
CN110041268B (en) Pyrimidine bipolar compound and application thereof in OLED (organic light emitting diode) device
JP2014116639A (en) Organic electroluminescent compound and light-emitting diode using the same
CN108774258B (en) Boron-containing heterocyclic compound and application thereof in organic photoelectric device
CN110041366B (en) Indenonanthracene derivative compound and application thereof
CN109608453B (en) Compound taking 4, 7-phenanthroline as receptor and application thereof
Liao et al. Aggregation-induced emission tetraphenylethene type derivatives for blue tandem organic light-emitting diodes
CN113264911A (en) Compound, organic light-emitting material and organic electroluminescent device
CN112174918B (en) Compound, hole transport material, organic electroluminescent device and display device
CN111303149B (en) Benzo five-membered fused heterocycle organic compound and application thereof
WO2023165079A1 (en) Dipyridinophenazine thermally activated delayed fluorescent material doped white electroluminescent device
CN106892903B (en) Organic electroluminescent compound based on phenazine and carbazole and luminescent device thereof
CN111718280A (en) P-type doped hole injection compound and application thereof
CN116332773A (en) Luminescent auxiliary material and preparation method and application thereof
CN110577488A (en) Compound with carbazole as core and application thereof in organic electroluminescent device
CN108864146B (en) Spirofluorene xanthene derivative and application thereof in OLED device
CN110343048A (en) A kind of organic compound and its application fluorene structured containing spiral shell dibenzocycloheptene
CN110577523B (en) Compound containing triarylamine structure and organic electroluminescent device prepared from compound
CN112125813B (en) Compound, hole transport material and organic electroluminescent device
CN109053739A (en) A kind of pyrrolotriazine derivatives and its application in OLED device
CN110963904A (en) Compound with ketone and fluorene as cores, preparation method and application thereof
CN110950846B (en) Benzimidazole bipyrimidine derivative and application thereof
CN101597255B (en) Organic material and application thereof in organic electroluminescence device (OELD)
CN117624171A (en) Organic electronic material and application thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant