CN111662298B - Compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device - Google Patents

Compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device Download PDF

Info

Publication number
CN111662298B
CN111662298B CN202010662496.4A CN202010662496A CN111662298B CN 111662298 B CN111662298 B CN 111662298B CN 202010662496 A CN202010662496 A CN 202010662496A CN 111662298 B CN111662298 B CN 111662298B
Authority
CN
China
Prior art keywords
substituted
unsubstituted
organic electroluminescent
compound
electroluminescent device
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
CN202010662496.4A
Other languages
Chinese (zh)
Other versions
CN111662298A (en
Inventor
梁现丽
程丹丹
范洪涛
段陆萌
杭德余
曹占广
班全志
陈婷
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.)
Beijing Yanhua Jilian Optoelectronic Technology Co ltd
Original Assignee
Beijing Yanhua Jilian Optoelectronic Technology 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 Beijing Yanhua Jilian Optoelectronic Technology Co ltd filed Critical Beijing Yanhua Jilian Optoelectronic Technology Co ltd
Priority to CN202010662496.4A priority Critical patent/CN111662298B/en
Publication of CN111662298A publication Critical patent/CN111662298A/en
Application granted granted Critical
Publication of CN111662298B publication Critical patent/CN111662298B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
    • H10K85/615—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
    • C09K2211/1018—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
    • C09K2211/1037—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
    • C09K2211/1088—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 belongs to the technical field of organic electroluminescent display, and particularly relates to a novel compound containing multiple heterocyclic rings and application thereof in an organic electroluminescent device. The novel polyheterocycle-containing compound provided by the invention has a structure shown as a formula (I). The compound has good thermal stability, and can be applied to OLED devices as a green light main body material to effectively improve the photoelectric properties of the devices. The OLED device containing the polyheterocyclic compound can be applied to the fields of display or illumination.

Description

Compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device
Technical Field
The invention belongs to the technical field of organic electroluminescent display, and particularly relates to a novel organic material with a multi-heterocyclic structure and application thereof in an organic electroluminescent (OLED) device.
Background
The application of the organic electroluminescent (OLED) material in the fields of information display materials, organic optoelectronic materials and the like has great research value and good application prospect. With the development of multimedia information technology, the requirements for the performance of flat panel display devices are higher and higher. The main display technologies at present are plasma display devices, field emission display devices, and organic electroluminescent display devices (OLEDs). The OLED has a series of advantages of self luminescence, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, and compared with a liquid crystal display device, the OLED does not need a backlight source, has a wider viewing angle and low power consumption, has the response speed 1000 times that of the liquid crystal display device, and has a wider application prospect.
Since the first reports of OLEDs, many scholars have been working on how to improve device efficiency and stability. Forrest and Thompson research groups find that the transition metal complex can be applied to Ph OLEDs (phosphorescent OLEDs), the phosphorescent material has strong spin-orbit coupling effect, and singlet excitons and triplet excitons can be simultaneously utilized, so that the quantum efficiency in the phosphorescent electroluminescent device theoretically reaches 100%. However, phosphorescent materials have a longer excited state lifetime, and are prone to form triplet-triplet quenching and triplet-polaron- quenching when the triplet exciton concentration is higher. Therefore, the phosphorescent material is often incorporated as a guest into the host material to reduce the concentration quenching phenomenon itself. Therefore, it is also an important matter to select a suitable host material in Phosphorescent organic electroluminescent devices (Ph OLEDs). Essential characteristics of the host material: (1) possesses a triplet energy level higher than that of the guest dye; (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, in order to meet the requirements, in addition to the refinement on the OLED panel manufacturing process, the development of an OLED material capable of meeting higher device indexes is particularly important. Therefore, a stable and efficient host material is developed, so that the driving voltage is reduced, the luminous efficiency of the device is improved, and the method has important practical application value.
Disclosure of Invention
The invention aims to provide an OLED main body material which has higher triplet state energy level, better carrier mobility, higher thermal stability and film forming stability and can be matched with adjacent energy levels, and application of the organic material in an OLED device.
In particular, the invention finds a novel class of polyheterocyclic compounds useful in organic electroluminescent devices. The parent nucleus of the series of compounds has an electron withdrawing effect, is connected with five-membered heterocyclic groups such as carbazole, furan, thiophene and the like with electron donating capability, can be used as a green light main body material, has good thermal stability and can be well applied to OLED devices. The series of compounds are represented by a general formula (I), and can be applied to OLED devices to achieve the purpose.
In a first aspect, the present invention provides a novel polyheterocycle-containing compound having the structure represented by formula (I):
Figure GDA0003022778810000021
in the formula (I), R1～R12Each independently selected from hydrogen atom, halogen atom, linear or branched alkyl, cycloalkyl, amino, alkylamino, substituted or unsubstituted aromatic group containing benzene ring and/or aromatic heterocyclic ring, and R1～R12Wherein at least one group is an aromatic group containing a five-membered heterocyclic ring.
Preferably, said R is1～R12Wherein at least one group is a substituted or unsubstituted aromatic group containing a five-membered heterocycle, the substituted or unsubstituted aromatic group containing a five-membered heterocycle contains at least one five-membered heterocycle, preferably one, two or three five-membered heterocycles(ii) a The five-membered heterocyclic ring contains at least one heteroatom, preferably one, two or three heteroatoms; the heteroatom is optionally selected from the group consisting of N atoms, S atoms, and O atoms; when the substituted or unsubstituted aromatic group containing a five-membered heterocyclic ring contains a plurality of hetero atoms, the respective hetero atoms may be the same as each other, may be partially the same as each other, or may be different from each other.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from: substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted phenanthrocarbazolyl, substituted or unsubstituted indoloindolyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthofuranyl.
In a preferred embodiment of the present invention, in the substituted aromatic group containing a five-membered heterocycle, the substituent may be optionally selected from: phenyl, naphthyl, biphenyl, benzo, naphtho, phenanthro, indolo (e.g., N-benzaindolo), benzothieno, benzofuro. The number of the substituents is an integer of 1 to 5, preferably 1 to 3.
As a preferred embodiment of the present invention, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure GDA0003022778810000022
Figure GDA0003022778810000031
Figure GDA0003022778810000041
preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure GDA0003022778810000042
Figure GDA0003022778810000051
more preferably, the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure GDA0003022778810000052
in each of the above-mentioned substituent groups, "- - -" represents a substitution position.
As a preferred embodiment of the present invention, the present invention provides a compound represented by the following structure:
Figure GDA0003022778810000061
Figure GDA0003022778810000071
Figure GDA0003022778810000081
Figure GDA0003022778810000091
Figure GDA0003022778810000101
Figure GDA0003022778810000111
the organic compound takes a multi-heterocyclic ring structure as a mother core, the mother core structure has good thermal stability, and simultaneously has proper HOMO and LUMO energy levels and Eg, and a group with strong electron donating capability is introduced into a proper position in the mother core structure, namely, five-membered heterocyclic ring structures such as carbazole, furan, thiophene and the like with strong electron donating capability are introduced into the structure, so that the OLED material with a novel structure is obtained. The material is applied to OLED devices and used as a green light main body material, and the photoelectric property of the device can be effectively improved. The device can be applied to the field of display or illumination.
In a second aspect, the present invention provides the use of an organic compound of formula (I) in the preparation of an organic electroluminescent device. Preferably, the present invention provides the use of the organic compound as a light emitting host material of an electroluminescent layer in an organic electroluminescent device; further preferably, the electroluminescent material is a green host material. The thickness of the electroluminescent layer can be 10-50 nm, and preferably 20-40 nm.
In a third aspect, the present invention provides an organic electroluminescent device comprising an electroluminescent layer comprising a compound according to the present invention.
As a preferable scheme of the invention, the organic electroluminescent device comprises a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer (containing the compound of the invention as a green light main body material), an electron transport layer, an electron injection layer and a cathode layer from bottom to top in sequence. Preferably, the thickness of the electroluminescent layer is 10-50 nm, preferably 20-40 nm.
In a fourth aspect, the present invention provides a display apparatus comprising the organic electroluminescent device.
In a fifth aspect, the present invention provides a lighting apparatus comprising the organic electroluminescent device.
The novel OLED material provided by the invention takes a multi-heterocyclic structure compound as a mother nucleus, and an electron-donating group is introduced into the structure of the mother nucleus, so that the novel OLED 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 material can be applied to the field of organic electroluminescence, can be used as a green light main body material, and can effectively improve the photoelectric property of a device.
Detailed Description
The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the present invention, and other equivalent changes or modifications made without departing from the spirit of the present invention are intended to be included within the scope of the appended claims.
According to the preparation method provided by the present invention, a person skilled in the art can use known common means to implement, such as further selecting a suitable catalyst and a suitable solvent, and determining a suitable reaction temperature, a suitable reaction time, a suitable material ratio, and the like, which are not particularly limited in the present invention. If not specifically stated, the starting materials for the preparation of solvents, catalysts, bases, etc. may be obtained by published commercial routes or by methods known in the art.
Example 1 Synthesis of intermediate M1
Figure GDA0003022778810000121
The synthetic route is as follows:
Figure GDA0003022778810000122
the method comprises the following specific steps:
(1) adding 4-chloro-1-fluoro-2-nitrobenzene (17.5g, 0.1mol) and 2-bromo-4-chloroaniline (30.8g, 0.15mol) into a 2L three-necked bottle with mechanical stirring, protecting with argon, heating to 180 ℃, keeping the temperature for reaction for more than 30 hours, wherein the color of the reaction solution gradually becomes red in the reaction process, and finally gradually becomes deep red. After the reaction is finished, an organic phase is separated, extracted, dried, subjected to column chromatography, and subjected to spin-drying to obtain 30g of orange-red solid M-01 with the yield of 83%.
(2) In a 1L three-necked flask equipped with a mechanical stirrer, M-01(36.0g, 0.1mol), sodium sulfide nonahydrate (96g, 0.4mol), ethanol (200mL), and water (100mL) were added, and the mixture was heated to reflux under nitrogen protection, and the reaction was terminated after refluxing for 3 hours. Separating organic phase, extracting, drying, column chromatography and spin-drying solvent to obtain 26.5g white solid M-02 with yield of 80%.
(3) Adding M-02(33.0g, 0.1mol) and 300mL of acetone into a 1L three-necked flask with mechanical stirring to completely dissolve the mixture, adding a solution of KOH (11.2g,0.2mol) dissolved in water (50mL), slowly dropwise adding 2-bromo-4-chlorobenzoyl chloride (25.2g, 0.1mol) into the reaction flask, gradually precipitating solids in the reaction flask, reacting at normal temperature for 2 hours after the dropwise adding is finished, and finishing the reaction. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 43.8g of white solid M-03 with the yield of 79%.
(4) Adding M-03(54.8g, 0.1mol) into a 1L three-necked bottle, adding 200mL of glycol ether under the protection of nitrogen, gradually heating to reflux, gradually dissolving the solid, magnetically stirring, keeping the temperature and reacting for 3 hours, and finishing the reaction. The organic phase was separated, extracted, dried, column chromatographed, and the solvent was spin-dried to give 40g of M-04 as a pale red solid in 76% yield.
(5) Adding M-04(53.0g, 0.1mol) and THF 800mL into a 2L three-necked flask under the protection of nitrogen, cooling to-78 deg.C, slowly adding n-butyllithium (100mL, 0.25mol) dropwise under stirring for about 30mins, flushing the dropping funnel with 50mL THF after dropping, keeping the temperature at-78 deg.C for 1.5 hr, and adding 20 g of freshly sublimed anhydrous AlCl3The mixture is kept at low temperature for 20 minutes, anhydrous acetone (30mL, 0.4mol) is slowly dropped, then a small amount of THF is used for washing a dropping funnel, the temperature is kept for 1 hour after the addition, then the temperature is slowly raised to room temperature, the mixture is stirred at room temperature for reaction for 4 hours, and the reaction is finished. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 25g of a white solid intermediate M1 with the yield of 61%.
Product MS (m/e): 412.03, respectively; elemental analysis (C)22H15Cl3N2): theoretical value C: 63.87%, H: 3.65%, N: 6.77 percent; found value C: 63.61%, H: 3.42%, N: 6.50 percent.
Example 2 Synthesis of intermediate M2
Figure GDA0003022778810000131
By using
Figure GDA0003022778810000132
Respectively replace
Figure GDA0003022778810000133
Figure GDA0003022778810000134
The intermediate M2 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 378.07, respectively; elemental analysis (C)22H16Cl2N2): theoretical value C: 69.67%, H: 4.25%, N: 7.39 percent; found value C: 69.42%, H: 4.01%, N: 7.12 percent.
Example 3 Synthesis of intermediate M3
Figure GDA0003022778810000135
By using
Figure GDA0003022778810000141
Instead of the former
Figure GDA0003022778810000142
The intermediate M3 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 378.07, respectively; elemental analysis (C)22H16Cl2N2): theoretical value C: 69.67%, H: 4.25%, N: 7.39 percent; found value C: 69.43%, H: 4.00%, N: 7.11 percent.
Example 4 Synthesis of intermediate M4
Figure GDA0003022778810000143
By using
Figure GDA0003022778810000144
Instead of the former
Figure GDA0003022778810000145
The intermediate M4 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 378.07, respectively; elemental analysis (C)22H16Cl2N2): theoretical value C: 69.67%, H: 4.25%, N: 7.39 percent; found value C: 69.41%, H: 4.00%, N: 7.08 percent.
Example 5 Synthesis of intermediate M5
Figure GDA0003022778810000146
By using
Figure GDA0003022778810000147
Respectively replace
Figure GDA0003022778810000148
The intermediate M5 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 344.11, respectively; elemental analysis (C)22H17ClN2): theoretical value C: 76.63%, H: 4.97%, N: 8.12 percent; found value C: 76.39%, H: 4.72%, N: 7.93 percent.
Example 6 Synthesis of intermediate M6
Figure GDA0003022778810000151
By using
Figure GDA0003022778810000152
Respectively replace
Figure GDA0003022778810000153
The intermediate M6 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 344.11, respectively; elemental analysis (C)22H17ClN2): theoretical value C: 76.63%, H: 4.97%, N: 8.12 percent; found value C: 76.39%, H: 4.72%, N: 7.93 percent.
Example 7 Synthesis of intermediate M7
Figure GDA0003022778810000154
By using
Figure GDA0003022778810000155
Respectively replace
Figure GDA0003022778810000156
The intermediate M7 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 344.11, respectively; elemental analysis (C)22H17ClN2): theoretical value C: 76.63%, H: 4.97%, N: 8.12 percent; found value C: 76.36%, H: 4.73%, N: 7.90 percent.
Example 8 Synthesis of intermediate M8
Figure GDA0003022778810000157
By using
Figure GDA0003022778810000158
Instead of the former
Figure GDA0003022778810000159
The intermediate M8 was obtained by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 378.07, respectively; elemental analysis (C)22H16Cl2N2): theoretical value C: 69.67%, H: 4.25%, N: 7.39 percent; found value C: 69.41%, H: 4.00%, N: 7.10 percent.
Example 9 Synthesis of intermediate M9
Figure GDA0003022778810000161
Figure GDA0003022778810000162
(1) Synthesis of intermediate M9-04:
by using
Figure GDA0003022778810000163
Respectively replace
Figure GDA0003022778810000164
Figure GDA0003022778810000165
Selecting a proper material ratio, and obtaining an intermediate M9-04 by the same synthesis method of the intermediate M1 with other raw materials and steps.
(2) Synthesis of intermediate M9:
under the protection of nitrogen, M9-04(51.0g, 0.1mol) and THF 800mL are added into a 2L three-necked bottle, the mixture is cooled to-78 ℃, n-butyllithium (44mL, 0.11mol) is slowly dropped under stirring for about 30mins, the dropping funnel is flushed with 50mL of THF after dropping, the temperature is kept at-78 ℃ for 1.5 hours after dropping, then anhydrous acetone (30mL, 0.4mol) is slowly dropped, then a small amount of THF is used for flushing the dropping funnel, the temperature is kept for 1 hour after adding, then the temperature is slowly raised to room temperature, the reaction is stirred at room temperature for 4 hours, and the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying with anhydrous molecular sieve, and pumping off solvent to obtain yellow solid.
This solid was dissolved in 300ml of dry CH2Cl2The mixture was cooled to 0 ℃ in an ice-water bath, methanesulfonic acid (19.2g, 0.2mol) was slowly added dropwise, after which stirring was continued for 2 hours at 0 ℃ and then increasedWarming to room temperature, stirring for 1 hour, TLC detecting reaction completion, adding saturated NaHCO3 solution to quench the reaction, adjusting to neutral, washing twice with dichloromethane, combining organic solvents, drying over anhydrous magnesium sulfate, column chromatography, spin drying solvent to obtain 29.5g white solid, intermediate M9, yield 70%.
Product MS (m/e): 422.02, respectively; elemental analysis (C)22H16BrClN2): theoretical value C: 62.36%, H: 3.81%, N: 6.61 percent; found value C: 62.10%, H: 3.55%, N: 6.38 percent.
Example 10 Synthesis of intermediate M10
Figure GDA0003022778810000171
By using
Figure GDA0003022778810000172
Respectively replace
Figure GDA0003022778810000173
The intermediate M10 was obtained first by selecting the appropriate material ratio and the other raw materials and procedures were the same as in example 1.
Product MS (m/e): 422.02, respectively; elemental analysis (C)22H16BrClN2): theoretical value C: 62.36%, H: 3.81%, N: 6.61 percent; found value C: 62.11%, H: 3.54%, N: 6.36 percent.
EXAMPLE 11 Synthesis of Compound I-12
Figure GDA0003022778810000174
The synthetic route is as follows:
Figure GDA0003022778810000175
A2L three-necked flask was equipped with magnetic stirring, and after nitrogen substitution, M1(41.2g, 0.1mol), (9-phenyl-9H-carbazol-3-yl) boronic acid (86.1g, 0.3mol), cesium carbonate (117g, 0.36mol) and dioxane 800ml were sequentially added, followed by stirring. After nitrogen replacement again, (2.2g, 11mmol) tri-tert-butylphosphine and (4.1g, 4.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating an organic phase, extracting, drying, performing column chromatography, and spin-drying the solvent to obtain 73.3g of pale yellow solid with the yield of about 71%.
Product MS (m/e): 1033.41, respectively; elemental analysis (C)76H5N5): theoretical value C: 88.26%, H: 4.97%, N: 6.77 percent; found value C: 88.03%, H: 4.72%, N: 6.56 percent.
EXAMPLE 12 Synthesis of Compound I-20
Figure GDA0003022778810000181
Synthesis of (Compound I-20)
The synthetic route is as follows:
Figure GDA0003022778810000182
using M2 instead of M1, (9- (naphthalene-2-yl) -9H-carbazol-3-yl) boronic acid instead of (9-phenyl-9H-carbazol-3-yl) boronic acid, the appropriate material ratios were chosen and the other raw materials and procedures were the same as in example 11 to give 66.9g of a pale yellow solid with a yield of about 75%.
Product MS (m/e): 892.36, respectively; elemental analysis (C)66H44N4): theoretical value C: 88.76%, H: 4.97%, N: 6.27 percent; found value C: 88.51%, H: 4.70%, N: 6.03 percent.
EXAMPLE 13 Synthesis of Compound I-33
Figure GDA0003022778810000183
Synthesis of (Compound I-33)
The synthetic route is as follows:
Figure GDA0003022778810000191
m3 was used in place of M1, and (4- (9H-carbazol-9-yl) phenyl) boronic acid was used in place of (9-phenyl-9H-carbazol-3-yl) boronic acid, and the other raw materials and procedures were the same as in example 11, to give 66.5g of a pale yellow solid with a yield of about 84%, with the selection of an appropriate material ratio.
Product MS (m/e): 792.33, respectively; elemental analysis (C)58H40N4): theoretical value C: 87.85%, H: 5.08%, N: 7.07 percent; found value C: 87.59%, H: 4.86%, N: 6.88 percent.
EXAMPLE 14 Synthesis of Compound I-46
Figure GDA0003022778810000192
Synthesis of (Compound I-46)
The synthetic route is as follows:
Figure GDA0003022778810000193
m4 was used in place of M1, and (5-phenyl-5H-benzo [ b ] carbazol-2-yl) boronic acid was used in place of (9-phenyl-9H-carbazol-3-yl) boronic acid, and the other raw materials and procedures were the same as in example 11, except that the appropriate material ratio was selected, whereby 76.7g of a pale yellow solid was obtained with a yield of about 86%.
Product MS (m/e): 892.36, respectively; elemental analysis (C)66H44N4): theoretical value C: 88.76%, H: 4.97%, N: 6.27 percent; found value C: 88.46%, H: 4.73%, N: 6.01 percent.
EXAMPLE 15 Synthesis of Compound I-59
Figure GDA0003022778810000194
Synthesis of (Compound I-59)
The synthetic route is as follows:
Figure GDA0003022778810000201
using M5 instead of M1 and (4- (7H-dibenzo [ c, g ] carbazol-7-yl) phenyl) boronic acid instead of (9-phenyl-9H-carbazol-3-yl) boronic acid, the appropriate material ratios were chosen and the other raw materials and procedures were the same as in example 11 to give 46.2g of a pale yellow solid with a yield of about 71%.
Product MS (m/e): 651.27, respectively; elemental analysis (C)48H33N3): theoretical value C: 88.45%, H: 5.10%, N: 6.45 percent; found value C: 88.13%, H: 4.86%, N: 6.26 percent.
EXAMPLE 16 Synthesis of Compound I-73
Figure GDA0003022778810000202
Synthesis of (Compound I-73)
The synthetic route is as follows:
Figure GDA0003022778810000203
using M6 instead of M1, (4- (10-phenylindole [3,2-b ] indol-5 (10H) -yl) phenyl) boronic acid instead of (9-phenyl-9H-carbazol-3-yl) boronic acid, the appropriate material ratios were chosen and the other starting materials and procedures were the same as in example 11 to give 55.3g of a pale yellow solid with a yield of about 83%.
Product MS (m/e): 666.28, respectively; elemental analysis (C)48H34N4): theoretical value C: 86.46%, H: 5.14%, N: 8.40 percent; found value C: 86.22%, H: 4.92%, N: 8.19 percent.
EXAMPLE 17 Synthesis of Compound I-85
Figure GDA0003022778810000211
Synthesis of (Compound I-85)
The synthetic route is as follows:
Figure GDA0003022778810000212
the method comprises the following specific steps:
m7 was used in place of M1 and (4- (11H-benzo [4,5] thieno [3,2-b ] carbazol-11-yl) phenyl) boronic acid was used in place of (9-phenyl-9H-carbazol-3-yl) boronic acid, and the other raw materials and procedures were the same as in example 11 except that the appropriate material ratio was selected to obtain 53.9g of a pale yellow solid with a yield of about 82%.
Product MS (m/e): 657.22, respectively; elemental analysis (C)46H31N3S): theoretical value C: 83.99%, H: 4.75%, N: 6.39 percent; found value C: 83.76%, H: 4.53%, N: 6.12 percent.
EXAMPLE 18 Synthesis of Compound I-98
Figure GDA0003022778810000213
Synthesis of (Compound I-98)
The synthetic route is as follows:
Figure GDA0003022778810000214
m8 was used in place of M1, and (3-phenylbenzo [ b ] thiophen-2-yl) boronic acid was used in place of (9-phenyl-9H-carbazol-3-yl) boronic acid, and the other raw materials and procedures were the same as in example 11, except that an appropriate material ratio was selected, whereby 57.4g of a pale yellow solid was obtained in a yield of about 79%.
Product MS (m/e): 726.2, respectively; elemental analysis (C)50H34N2S2): theoretical value C: 82.61%, H: 4.71%, N: 3.85 percent; found value C: 82.39%, H: 4.40%, N: 3.62 percent.
EXAMPLE 19 Synthesis of Compound I-136
Figure GDA0003022778810000221
Synthesis of (Compound I-136)
The synthetic route is as follows:
Figure GDA0003022778810000222
the method comprises the following specific steps:
into a 1L three-necked flask, M9(42.2g, 0.1mol), (4- (9H-carbazol-9-yl) phenyl) boronic acid (28.7g, 0.1mol), sodium carbonate (21.2g,0.2mol), toluene 150mL, ethanol 150mL, and water 150mL were charged, and Pd (PPh) was added after the reaction system was purged with nitrogen3)4(11.5g, 10 mmol). The reaction was heated under reflux (temperature in the system: about 78 ℃ C.) for 3 hours to stop the reaction. The solvent is evaporated off, dichloromethane is extracted, anhydrous magnesium sulfate is dried, filtration is carried out, petroleum ether/ethyl acetate (2:1) column chromatography is carried out, the solvent is dried in a rotating mode, ethyl acetate is pulped, and filtration is carried out to obtain 47.4g of light yellow solid I-136-1 with the yield of about 81%.
A1L three-necked flask is stirred by magnetic force, after nitrogen replacement, I-136-1(70.7g, 0.1mol), (5-phenyl-5H-benzo [ b ] carbazol-2-yl) boric acid (33.7g, 0.1mol), cesium carbonate (39g, 0.12mol) and dioxane 400ml are added in sequence, and stirring is started. After nitrogen replacement again, (0.8g, 4mmol) tri-tert-butylphosphine and (1.4g, 1.5mmol) tris (dibenzylideneacetone) dipalladium were added. After the addition, heating and raising the temperature, controlling the temperature to be 80-90 ℃ for reaction for 4 hours, and cooling after the reaction is finished. Adjusting to neutrality, separating organic phase, extracting, drying, column chromatography, and spin-drying solvent to obtain 64.0g pale yellow solid I-136 with yield of about 76%.
Product MS (m/e): 842.34, respectively; elemental analysis (C)62H42N4): theoretical value C: 88.33%, H: 5.02%, N: 6.65 percent; found value C: 88.10%, H: 4.79%, N: 6.41 percent.
EXAMPLE 20 Synthesis of Compound I-138
Figure GDA0003022778810000231
Synthesis of (Compound I-138)
The synthetic route is as follows:
Figure GDA0003022778810000232
m10 was used in place of M9, (4- (7H-dibenzo [ c, g ] carbazol-7-yl) phenyl) boronic acid in place of (4- (9H-carbazol-9-yl) phenyl) boronic acid, and dibenzo [ b, d ] thiophen-2-ylboronic acid in place of (5-phenyl-5H-benzo [ b ] carbazol-2-yl) boronic acid, and the appropriate material ratios were selected and the other raw materials and procedures were the same as in example 11 to give 62.5g of pale yellow solid I-138 in about 75% yield.
Product MS (m/e): 833.29, respectively; elemental analysis (C)60H39N3S): theoretical value C: 86.40%, H: 4.71%, N: 5.04 percent; found value C: 86.18%, H: 4.49%, N: 4.76 percent.
According to the technical schemes of the examples 1 to 20, other compounds of I-1 to I-140 can be synthesized only by simply replacing corresponding raw materials and not changing any substantial operation.
EXAMPLE 21 use of Compounds of the invention as Green host materials
The embodiment provides a group of OLED green light devices, and the structure of the device is as follows:
ITO/HATCN (1nm)/HT01(40nm)/NPB (30nm)/EML (30nm) (containing any of the compounds provided in examples 11-20)/Bphen (30nm)/LiF (1 nm)/Al.
The molecular structure of each functional layer material is as follows:
Figure GDA0003022778810000233
Figure GDA0003022778810000241
the preparation process of the OLED green light device OLED-1 comprises the following steps:
(1) ultrasonically cleaning a glass substrate coated with an ITO transparent conductive film in cleaning solution, ultrasonically treating the glass substrate in deionized water, ultrasonically removing oil in a mixed solution of acetone and ethanol (the volume ratio is 1: 1), baking the glass substrate in a clean environment until the water is completely removed, carrying out etching and ozone treatment by using an ultraviolet lamp, and bombarding the surface by using low-energy cation beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form HATCN as a first hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then evaporating a second hole injection layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 40 nm; then evaporating a hole transport layer NPB with the evaporation rate of 0.1nm/s and the evaporation film thickness of 30 nm;
(3) vacuum evaporating EML (Electron cyclotron resonance) on the hole transport layer to serve as a light emitting layer of the device, wherein the EML comprises the green light host material (I-12) and the dye material, placing the host material serving as the light emitting layer in a chamber of vacuum vapor deposition equipment by using a multi-source co-evaporation method, and adding Ir (ppy) serving as a dopant3Placing in another chamber of vacuum vapor deposition equipment, and adjusting evaporation rate of main material to 0.1nm/s, Ir (ppy)3The concentration of (2) is 10%, and the total film thickness of evaporation plating is 30 nm;
(4) evaporating Bphen on the luminescent layer in vacuum to form an electron transport layer with the thickness of 30nm, wherein the evaporation rate is 0.1 nm/s;
(5) LiF with the thickness of 1nm is sequentially subjected to vacuum evaporation on the electron transport layer to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
And (4) respectively obtaining the OLED-2-OLED-10 provided by the invention by respectively replacing I-12 in the step (3) with I-20, I-33, I-46, I-59, I-73, I-85, I-98, I-136 and I-138 according to the same steps.
Following the same procedure as above, only replacing I-12 in step (3) with CBP (comparative compound), comparative example OLED-11 provided by the present invention was obtained. The structure of the CBP is specifically as follows:
Figure GDA0003022778810000242
the performance of the obtained devices OLED-1 to OLED-11 is detected, and the detection results are shown in Table 1.
Table 1: performance test result of OLED device
Figure GDA0003022778810000251
From the above, the devices OLED-1 to OLED-10 prepared by using the organic material shown in the formula (I) provided by the invention have higher current efficiency, and under the condition of the same brightness, the working voltage is obviously lower than that of the device OLED-11 using CBP as the main material, so that the organic material is a green light main material with good performance.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (9)

1. A compound of formula (I):
Figure FDA0003022778800000011
wherein the content of the first and second substances,
R1～R12each independently is selected from hydrogen atom, halogen atom, straight chain or branched chain alkyl, cycloalkyl, amino, alkylamino, substituted or unsubstituted aromatic group containing five-membered heterocycle, and R1～R12Wherein at least one group is a substituted or unsubstituted aromatic group containing a five-membered heterocycle;
wherein the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from: substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted phenanthrocarbazolyl, substituted or unsubstituted indoloindolyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthofuranyl;
in the substituted aromatic group containing the five-membered heterocyclic ring, the substituent is selected from the following groups: phenyl, naphthyl, biphenyl, benzo, naphtho, phenanthro, N-benzindolyl, benzothienoyl, benzofuroyl; the number of the substituents is an integer of 1 to 3.
2. The compound of claim 1, wherein the substituted or unsubstituted aromatic group containing a five-membered heterocycle is selected from:
Figure FDA0003022778800000012
Figure FDA0003022778800000021
Figure FDA0003022778800000031
in each substituent group, "- - -" represents a substitution position.
3. The compound of claim 1, selected from the compounds of the following specific structures:
Figure FDA0003022778800000032
Figure FDA0003022778800000041
Figure FDA0003022778800000051
Figure FDA0003022778800000061
Figure FDA0003022778800000071
Figure FDA0003022778800000081
4. use of a compound according to any one of claims 1 to 3 for the preparation of an organic electroluminescent device.
5. Use according to claim 4, wherein the compound according to any one of claims 1 to 3 is used as a light-emitting host material of an electroluminescent layer in an organic electroluminescent device.
6. An organic electroluminescent device comprising an electroluminescent layer containing a compound according to any one of claims 1 to 3.
7. The organic electroluminescent device according to claim 6, wherein the organic electroluminescent device comprises, in order from bottom to top, a transparent substrate, an anode layer, a hole transport layer, an electroluminescent layer comprising the compound according to any one of claims 1 to 3, an electron transport layer, an electron injection layer, and a cathode layer.
8. A display apparatus, wherein the display apparatus comprises the organic electroluminescent device according to claim 6 or 7.
9. An illumination apparatus, wherein the illumination apparatus comprises the organic electroluminescent device according to claim 6 or 7.
CN202010662496.4A 2020-07-10 2020-07-10 Compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device Active CN111662298B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202010662496.4A CN111662298B (en) 2020-07-10 2020-07-10 Compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010662496.4A CN111662298B (en) 2020-07-10 2020-07-10 Compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device

Publications (2)

Publication Number Publication Date
CN111662298A CN111662298A (en) 2020-09-15
CN111662298B true CN111662298B (en) 2021-08-10

Family

ID=72392173

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010662496.4A Active CN111662298B (en) 2020-07-10 2020-07-10 Compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device

Country Status (1)

Country Link
CN (1) CN111662298B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112079867B (en) * 2020-09-27 2022-11-11 北京燕化集联光电技术有限公司 P-containing multi-heterocyclic structure compound and application thereof
CN112159430B (en) * 2020-09-29 2022-11-11 北京燕化集联光电技术有限公司 PO-containing multi-heterocyclic structure compound and application thereof
CN112341499B (en) * 2020-11-05 2022-07-12 北京燕化集联光电技术有限公司 Sulfur-containing organic electrophosphorescent luminescent material and application thereof
CN112521327A (en) * 2020-12-17 2021-03-19 北京燕化集联光电技术有限公司 Organic compound and application thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170237015A1 (en) * 2016-02-11 2017-08-17 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
WO2017210206A1 (en) * 2016-05-31 2017-12-07 The Scripps Research Institute Ultra-potent vina alkaloids: added molecular complexity further disrupts the tublin dimer-dimer interface
CN111039954A (en) * 2019-11-28 2020-04-21 北京燕化集联光电技术有限公司 Novel organic material and application thereof in device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170237015A1 (en) * 2016-02-11 2017-08-17 Samsung Electronics Co., Ltd. Condensed cyclic compound and organic light-emitting device including the same
WO2017210206A1 (en) * 2016-05-31 2017-12-07 The Scripps Research Institute Ultra-potent vina alkaloids: added molecular complexity further disrupts the tublin dimer-dimer interface
CN111039954A (en) * 2019-11-28 2020-04-21 北京燕化集联光电技术有限公司 Novel organic material and application thereof in device

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Highly regioselective synthesis of fused seven-membered rings through copper-catalyzed cross-coupling;Peng Sang等;《ChemComm》;20121203;第49卷(第7期);全文 *
Transition-metal-free synthesis of indole-fused dibenzo[b,f][1,4]oxazepines via Smiles rearrangement;Fangdong Hu等;《Org. Biomol. Chem》;全文;20161108;第14卷(第47期) *

Also Published As

Publication number Publication date
CN111662298A (en) 2020-09-15

Similar Documents

Publication Publication Date Title
CN111689989B (en) Containing SO2Polyheterocyclic compounds and uses thereof
CN111662298B (en) Compound containing multiple heterocyclic rings and application thereof in organic electroluminescent device
CN111689971B (en) Multi-heterocyclic compound and application thereof
CN111689985B (en) Containing SO2Compound with multi-heterocyclic structure and application thereof
CN111689984B (en) Compound containing multi-heterocyclic structure and application thereof
CN111747970B (en) Containing SO2Polyheterocyclic compounds and their use
CN111662308A (en) SO (SO)2Compound with multi-heterocyclic structure and application thereof
CN111635421B (en) Organic material with multi-heterocyclic structure and application thereof
CN111875618B (en) Compound with multi-heterocyclic structure and application thereof
CN112079867A (en) P-containing multi-heterocyclic structure compound and application thereof
CN111635420B (en) Novel polyheterocyclic compound and application thereof
CN114560870B (en) Sulfur-containing polycyclic aromatic compound and application thereof
CN112745322B (en) Organic material and application thereof in organic electroluminescent device
CN113004262B (en) Organic material and application thereof
CN112341465B (en) Novel polyheterocyclic compound and application thereof
CN111747961B (en) Compound containing multiple heterocycles and application
CN111303012A (en) Indeno fluoranthene compound and application thereof
CN111909172B (en) Oxygen-containing multi-heterocyclic compound and application thereof
CN112321648A (en) P-containing organic electrophosphorescent material and application thereof
CN112159430B (en) PO-containing multi-heterocyclic structure compound and application thereof
CN112961142B (en) Organic material and application thereof in OLED device
CN114773360B (en) Organic material and application thereof in electroluminescent device
CN111763210B (en) Compound containing multi-heterocyclic structure and application
CN111961063B (en) Oxygen-containing multi-heterocyclic compound and application thereof
CN112142798B (en) PO-containing multi-heterocyclic compound 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
PE01 Entry into force of the registration of the contract for pledge of patent right

Denomination of invention: A Compound Containing Multiple Heterocycles and Its Application in Organic Electroluminescent Devices

Effective date of registration: 20230524

Granted publication date: 20210810

Pledgee: Agricultural Bank of China Limited Beijing Fangshan Branch

Pledgor: BEIJING YANHUA JILIAN OPTOELECTRONIC TECHNOLOGY Co.,Ltd.

Registration number: Y2023110000201

PE01 Entry into force of the registration of the contract for pledge of patent right
PC01 Cancellation of the registration of the contract for pledge of patent right

Granted publication date: 20210810

Pledgee: Agricultural Bank of China Limited Beijing Fangshan Branch

Pledgor: BEIJING YANHUA JILIAN OPTOELECTRONIC TECHNOLOGY Co.,Ltd.

Registration number: Y2023110000201