CN113444112A - Heterocyclic compounds and their use in organic electroluminescent devices - Google Patents

Heterocyclic compounds and their use in organic electroluminescent devices Download PDF

Info

Publication number
CN113444112A
CN113444112A CN202110711690.1A CN202110711690A CN113444112A CN 113444112 A CN113444112 A CN 113444112A CN 202110711690 A CN202110711690 A CN 202110711690A CN 113444112 A CN113444112 A CN 113444112A
Authority
CN
China
Prior art keywords
substituted
chemical formula
group
unsubstituted
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202110711690.1A
Other languages
Chinese (zh)
Inventor
王湘成
何为
向传义
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.)
Shanghai Yaoyi Electronic Technology Co ltd
Original Assignee
Shanghai Yaoyi Electronic 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 Shanghai Yaoyi Electronic Technology Co ltd filed Critical Shanghai Yaoyi Electronic Technology Co ltd
Priority to CN202110711690.1A priority Critical patent/CN113444112A/en
Publication of CN113444112A publication Critical patent/CN113444112A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
    • 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
    • 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

Landscapes

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

Abstract

The invention discloses a method for preparing a compoundCyclic compounds and their use in organic electroluminescent devices, the heterocyclic compounds having
Figure DDA0003133166100000011
Structure shown, X1Is N, X2To X6Are the same or different from each other, are each independently selected from C or N, and at least one is N; ar is an aromatic ring or an aromatic heterocyclic ring having 5 to 30 carbon atoms; r1From- (L)1)m‑A1Represents: l is1Is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene; m is an integer of 0 to 10, and when m is not less than 2, L1Are the same or different from each other; a. the1Is a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. The heterocyclic compound has high refractive index, heat resistance and light coupling efficiency, and can realize low driving voltage and simultaneously prolong the service life when being used for an organic electroluminescent device.

Description

Heterocyclic compounds and their use in organic electroluminescent devices
Technical Field
The invention belongs to the field of organic electroluminescent materials, and particularly relates to a heterocyclic compound and application thereof in an organic electroluminescent device.
Background
Currently, as the display device using an organic electroluminescent device (OLED) has an increasing area, problems of efficiency or lifetime need to be solved. Efficiency and lifetime, driving voltage, and the like are related to each other, and as the efficiency is increased, the driving voltage is relatively decreased, and when the driving voltage is decreased, crystallization of the organic material caused by joule heat generated during driving becomes less, resulting in an increase in lifetime.
The light efficiency of an organic electroluminescent device is generally divided into internal light emission efficiency and external light emission efficiency. Internal light emission efficiency relates to how excitons are efficiently generated and light conversion is achieved in organic material layers such as a hole transport layer, a light emitting layer, and an electron transport layer disposed between a first electrode and a second electrode (i.e., between an anode and a cathode); the external light emission efficiency (also referred to as "light coupling efficiency") indicates the efficiency of light generated in the organic material layer, extracted outside the organic electroluminescent device. When high light conversion efficiency is obtained in the organic material layer (i.e., when internal light emission efficiency is high), the overall light efficiency of the organic electroluminescent device is still low when external light emission efficiency is low. In order to improve the light coupling efficiency, it has been proposed to mount a capping layer (Cappinglayer) having a high refractive index on the outside of a translucent electrode having a low refractive index of an organic electroluminescent device, and a material for the capping layer is required to have a high refractive index and to have excellent film stability or durability, but the molecular stability of a capping layer material commonly used in the market can satisfy the use requirements, but the refractive index is not high as a whole, and the overall properties are yet to be further improved.
Disclosure of Invention
The main object of the present invention is to provide a heterocyclic compound having a structure represented by chemical formula 1 or chemical formula 2:
[ chemical formula 1]
Figure BDA0003133166080000011
[ chemical formula 2]
Figure BDA0003133166080000012
Wherein, in chemical formula 1 and chemical formula 2,
X1is N;
X2to X6Are the same or different from each other, are each independently selected from C or N, and at least one is N;
ar is an aromatic ring or an aromatic heterocyclic ring having 5 to 30 carbon atoms;
R1from- (L)1)m-A1Represents:
L1is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene;
m is an integer of 0 to 10, and when m is not less than 2, L1Are the same or different from each other;
A1is a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
The heterocyclic compound containing anthryl/phenanthryl has the following advantages: high refractive index, heat resistance and light coupling efficiency.
Compared with the prior art, the invention has the beneficial effects that: the heterocyclic compound provided by the invention has high refractive index under 450nm, can greatly improve the luminous efficiency when being used as a covering layer material of an organic electroluminescent device, realizes low driving voltage and prolongs the service life.
The above-described and other features, aspects, and advantages of the present invention will become more apparent with reference to the following detailed description.
Drawings
Other features, objects and advantages of the invention will become more apparent upon reading of the detailed description of non-limiting embodiments with reference to the following drawings:
fig. 1 is a schematic structural view of an organic electroluminescent device in the example.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the drawings of the embodiments of the present invention. It is to be understood that the embodiments described are only a few embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the described embodiments of the invention without any inventive step, are within the scope of protection of the invention.
The heterocyclic compounds used in the following examples have a structure as shown in chemical formula 1 or chemical formula 2:
[ chemical formula 1]
Figure BDA0003133166080000021
[ chemical formula 2]
Figure BDA0003133166080000031
Wherein, in chemical formula 1 and chemical formula 2,
X1is N;
X2to X6Are the same or different from each other, are each independently selected from C or N, and at least one is N;
ar is an aromatic ring or an aromatic heterocyclic ring having 5 to 30 carbon atoms;
R1from- (L)1)m-A1Represents:
L1is a direct health-care product,A substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene;
m is an integer of 0 to 10, and when m is not less than 2, L1Are the same or different from each other;
A1is a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
The substituents in the compound represented by chemical formula 1 or chemical formula 2 are described below, but not limited thereto.
"substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boryl group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, and a heterocyclic group, or unsubstituted; or a substituent linking two or more of the above substituents, or unsubstituted, e.g., "a substituent linking two or more substituents" includes biphenyl, i.e., biphenyl can be an aryl group or a substituent linking two phenyl groups.
"adjacent group" means a substituent which replaces an atom directly bonded to an atom substituted with the corresponding substituent, a substituent which is located closest to the corresponding substituent in space, or another substituent which replaces an atom substituted with the corresponding substituent, for example, two substituents which substitute for the ortho position in the benzene ring and two substituents which substitute for the same carbon in the aliphatic ring may be "adjacent groups" to each other, or a substituent which substitutes for N in the carbazole and a substituent which substitutes for carbon No. 2 or carbon No. 8 in the carbazole may be "adjacent groups".
"adjacent groups are bonded to each other to form a substituted or unsubstituted ring" means that adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a condensed ring thereof, wherein the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring, and the aromatic heterocyclic ring may be monocyclic or polycyclic.
"amino" includes alkylamino, aralkylamino, heteroarylamino, arylamino or arylheteroarylamino (amino substituted with aryl and heterocyclic groups), and the number of carbon atoms is preferably 1 to 40; wherein: the alkylamino group can include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthracylamino, 9-methyl-anthracylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, triphenylamino; the arylamine group may include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group, and the aryl group in the arylamine group may be a monocyclic aryl group, a polycyclic aryl group, or a combination of a monocyclic aryl group and a polycyclic aryl group, such as a phenylamino group, a naphthylamine group, a biphenylamino group, an anthrylamino group, a 3-methyl-phenylamino group, a 4-methyl-naphthylamine group, a 2-methyl-biphenylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a phenylnaphthylamine group, a ditolylamino group, a phenyltolylamino group, a carbazole, a triphenylamine group; heteroarylamino includes substituted or unsubstituted mono-heteroarylamino, substituted or unsubstituted di-heteroarylamino, or substituted or unsubstituted tri-heteroarylamino, and heteroaryl can be a monocyclic heterocyclyl, a polycyclic heterocyclyl, or a combination of monocyclic and polycyclic heterocyclyls.
The "aryl group" preferably has 6 to 60 carbon atoms. According to some embodiments, the number of carbon atoms of the aryl group is from 6 to 30; according to some embodiments, the number of carbon atoms of the aryl group is from 6 to 20. The aryl group can be monocyclic aryl group or polycyclic aryl group, the monocyclic aryl group comprises phenyl, biphenyl, terphenyl, quaterphenyl and pentabiphenyl group, and the polycyclic aryl group comprises naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl and fluorenyl.
"heterocyclic group" contains N, O, P, S, Si and one or more of Se as a hetero atom, and the number of carbon atoms is preferably 1 to 60. According to some embodiments, the number of carbon atoms in the heterocyclic group is from 1 to 30, including pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiapyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxanyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazindenyl, indolyl, indolinyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, Carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazoloquinazolinyl, benzimidazolophenanthridinyl.
The above description of heterocyclyl groups can be applied to heteroaryl groups, except that the heteroaryl group is aromatic.
The above description of heterocyclyl groups can be applied to heteroarylenes, except that the heteroarylene group is divalent.
The above description of aryl groups applies to arylene groups, except that arylene groups are divalent.
The above description of aryl groups applies to aryl groups in aryloxy, arylthio, arylsulfonyl, arylphosphino, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino, and arylheteroarylamino groups.
According to some embodiments of the present invention, chemical formula 1 or chemical formula 2 may be represented by any one of the following chemical structures:
Figure BDA0003133166080000051
according to some embodiments of the present invention, chemical formula 1 or chemical formula 2 may be represented by a chemical structure of any one of chemical formulae 3 to 8, [ chemical formula 3], [ chemical formula 4], and [ chemical formula 5] are, in order:
Figure BDA0003133166080000052
[ chemical formula 6], [ chemical formula 7], and [ chemical formula 8] are, in order:
Figure BDA0003133166080000053
in chemical formulas 3 to 8, X1To X6、R1Are the same as chemical formula 1 or chemical formula 2.
According to some embodiments of the present invention, in chemical formulas 1 to 8, L1Is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 1 to 60 carbon atoms; a. the1Is a substituted or unsubstituted alkylamino group having 1 to 40 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamine group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 1 to 60 carbon atoms.
According to some embodiments of the present invention, chemical formula 1 or chemical formula 2 may be selected from any one of the following chemical structures numbered 1 to 115:
Figure BDA0003133166080000061
Figure BDA0003133166080000071
Figure BDA0003133166080000081
Figure BDA0003133166080000091
the following synthetic examples 1 to 7 describe in detail the production methods of the heterocyclic compounds 11, 25, 41, 60, 86, 100 and 103, and it is not noted that the raw materials of the production methods are all commercially available, and the synthetic methods of the other heterocyclic compounds are similar to the synthetic examples 1 to 7. Wherein, the synthesis of the heterocyclic bromine compound adopts a ring closing reaction, and the technical route is shown as follows:
Figure BDA0003133166080000101
Figure BDA0003133166080000102
the anthryl/phenanthryl heterocyclic amine or anthryl/phenanthryl heterocyclic boronic acid synthesis can be obtained by functional group conversion.
Synthesis example 1
In the synthesis example, heterocyclic compound 11 is synthesized, and the technical route is as follows:
Figure BDA0003133166080000103
in a three-neck flask, solid raw materials 11-1(15g, 50mmol), 11-2(8.7g, 26mmol), palladium acetate (0.15g, 1%), cesium carbonate (32g, 100mmol) are added, solvents of toluene 100mL, ethanol 10mL, purified water 10mL are added, vacuum pumping, nitrogen protection and replacement are carried out for 3 times, and the reaction is placed in an oil bath kettle with the external temperature of 100 ℃ for reaction for 4 hours.
After cooling, the celite was filtered. The filtrate was spin dried on a rotary evaporator to give crude grey solid which was purified using dichloromethane/ethanol ═ 1: 2(10V), slurried overnight at room temperature, filtered the solid and concentrated in tetrahydrofuran/ethanol ═ 1: 2(100mL), slurried overnight at room temperature. The solid was filtered to give an off-white solid and the crude product was recrystallized by heating with 50mL of toluene. Filtration gave 12g of a white solid in 69.7% yield.
Example 2
In the synthesis example, heterocyclic compound 25 is synthesized, and the technical route is as follows:
Figure BDA0003133166080000104
synthesis of Compounds 25-3: in a three-necked flask, solid starting materials 25-1(30g, 100mmol), 25-2(18.2g, 50mmol), palladium acetate (0.30g, 1%), cesium carbonate (61g, 188mmol) were added, and the solvents toluene 200mL, ethanol 20mL, and purified water 20mL were added. Vacuumizing, protecting with nitrogen and replacing 3 times. The reaction was placed in an oil bath at an external temperature of 100 ℃ and allowed to react for 4 hours. After cooling, the celite was filtered. The filtrate was spin-dried on a rotary evaporator to give a crude grey solid. Crude product was purified with dichloromethane/ethanol ═ 1: 3(10V), slurried at room temperature overnight. The solid was filtered and washed with tetrahydrofuran/ethanol ═ 1: 3(200mL), slurried overnight at room temperature. The solid was filtered to give an off-white solid. The crude product was recrystallized from 100mL of toluene by heating. Filtration gave 22g of a white solid in 70.8% yield.
Synthesis of compound 25: in a three-necked flask, solid 25-3(15g, 24mmol), solid 2-2(6.9g, 24mmol), palladium acetate (0.15g, 1%), cesium carbonate (16.2g, 50mmol) were added, and solvent toluene 100mL, ethanol 10mL, purified water 10mL was added. Vacuumizing, protecting with nitrogen and replacing 3 times. The reaction was placed in an oil bath at an external temperature of 100 ℃ and allowed to react for 4 hours. After cooling, the celite was filtered. The filtrate was spin-dried on a rotary evaporator to give a crude grey solid. Crude product was purified with dichloromethane/ethanol ═ 1: 2(10V), slurried overnight at room temperature. The solid was filtered and washed with tetrahydrofuran/ethanol ═ 1: 2(200mL), slurried overnight at room temperature. The solid was filtered to give an off-white solid. The crude product was recrystallized from 100mL of toluene by heating. Filtration gave 14g of a white solid in 70.7% yield.
Example 3
In the synthesis example, heterocyclic compound 41 is synthesized, and the technical route is as follows:
Figure BDA0003133166080000111
synthesis of Compound 41-3: in a three-necked flask, raw materials 41-1(15g, 50mmol) and 41-2(9.1g, 25mmol), palladium acetate (0.15g, 1%), cesium carbonate (32g, 100mmol) were charged, and solvents of toluene 100mL, ethanol 10mL and purified water 10mL were added. Vacuumizing, protecting by nitrogen and replacing for 3 times, and reacting for 4 hours in an oil bath pan with the external temperature of 100 ℃. After cooling, the mixture was filtered through celite, and the filtrate was spun dry on a rotary evaporator to give crude grey solid which was purified by evaporation with dichloromethane/ethanol ═ 1: 3(10V), slurried overnight at room temperature, filtered the solid and concentrated in tetrahydrofuran/ethanol ═ 1: 2(200mL), slurried overnight at room temperature, filtering the solid to give an off-white solid, heating the crude product with 100mL of toluene to recrystallize, filtering to give 11g of a white solid in 70.7% yield.
Synthesis of compound 41: in a three-necked flask, raw materials 41-3(10g, 16mmol), 4-4(4.6g, 16mmol), palladium acetate (0.15g, 1%), cesium carbonate (9g, 30mmol) were charged, and 100mL of toluene, 10mL of ethanol, and 10mL of purified water as solvents were added. Vacuumizing, protecting by nitrogen and replacing for 3 times, and reacting for 4 hours in an oil bath pan with the external temperature of 100 ℃. After cooling, the mixture was filtered through celite, and the filtrate was spun dry on a rotary evaporator to give crude grey solid which was purified by evaporation with dichloromethane/ethanol ═ 1: 2(10V), slurried overnight at room temperature, filtered the solid and concentrated in tetrahydrofuran/ethanol ═ 1: 2(200mL), slurried overnight at room temperature, filtering the solid to give an off-white solid, heating the crude product with 100mL of toluene to recrystallize, filtering to give 10g of a white solid in 75.1% yield.
Example 4
In the synthesis example, heterocyclic compound 60 is synthesized, and the technical route is as follows:
Figure BDA0003133166080000121
synthesis of Compound 60-3: 60-2(11.5g, 44.8mmol), NaOBu-t (7g, 73mmol) and toluene (100mL) were added to a three-necked flask, the system was replaced with nitrogen, the reaction mixture was heated to 70 ℃ and Pd was added thereto2(dba)3(0.15g, 1% w/w) and t-Bu3P(1.5g，10％w/w), nitrogen substitution. 60-1(15g, 44.8mmol) was dissolved in 15mL of toluene and slowly added dropwise. After the addition, the system was heated to 110 ℃ and reacted for 3 hours. After the reaction was completed, the reaction solution was cooled to 50 ℃, passed through silica gel, rinsed with 100mL of toluene, the resulting filtrate was concentrated to remove half of the volume, 150mL of ethanol was added, stirred at room temperature for 1 hour, and filtered to obtain an off-white solid 60-3(16g, yield 69.8%).
Synthesis of compound 60: in a three-necked flask, 60-3(10g, 19.5mmol), 60-4(6.5g, 19.5mmol), Pd were added2(dba)3(0.1g，1％)，t-Bu3P (1g, 10%), NaOBu-t (2.9g, 30mmol), then toluene (100mL) is added, nitrogen is replaced, the reaction solution is heated to reflux, the reaction is stirred for 2h, the reaction solution is cooled to 80 ℃, and the hot reaction solution passes through a silica gel column and is used by 100 mL. Concentrating the mother liquor to 60mL, adding 100mL of ethanol, stirring at room temperature for 2h, filtering, adding 40mL of toluene into the solid, refluxing to dissolve, adding 60mL of petroleum ether, stirring at room temperature for 2h, filtering, and spin-drying to obtain 10g of white solid with the yield of 67.1%.
Example 5
The heterocyclic compound 86 is synthesized in the synthesis example, and the technical route is as follows:
Figure BDA0003133166080000122
synthesis of Compound 86-3: in a three-necked flask, starting materials 86-1(15g, 62.7mmol) and 86-2(11.4g, 31.4mmol), palladium acetate (0.15g, 1%), cesium carbonate (32g, 100mmol) were charged, and the solvents toluene 100mL, ethanol 10mL, and purified water 10mL were added. Vacuumizing, protecting with nitrogen and replacing 3 times. The reaction was placed in an oil bath at an external temperature of 100 ℃ and allowed to react for 4 hours. After cooling, the celite was filtered. The filtrate was spin-dried on a rotary evaporator to give a crude grey solid. Crude product was purified with dichloromethane/ethanol ═ 1: 2(10V), slurried overnight at room temperature. The solid was filtered and washed with tetrahydrofuran/ethanol ═ 1: 2(150mL), slurried overnight at room temperature. The solid was filtered to give an off-white solid. The crude product was recrystallized from 100mL of toluene by heating. Filtration gave 11g of a white solid in 70.5% yield.
Synthesis of compound 86: in a three-necked flask, raw materials 86-3(10g, 20mmol) and 86-4(6g, 20mmol), palladium acetate (0.1g, 1%), cesium carbonate (13g, 40mmol) were charged, and solvents of toluene 100mL, ethanol 10mL and purified water 10mL were added. Vacuumizing, protecting with nitrogen and replacing 3 times. The reaction was placed in an oil bath at an external temperature of 100 ℃ and allowed to react for 4 hours. After cooling, the mixture was filtered through celite and the filtrate was spun dry on a rotary evaporator to give a crude grey solid. Crude product was purified with dichloromethane/ethanol ═ 1: 1(20V), slurried overnight at room temperature, the solid was filtered and concentrated in tetrahydrofuran/ethanol ═ 1: 3(100mL), slurried overnight at room temperature, the solid filtered to give an off-white solid and the crude product recrystallized by heating with 80mL of toluene. Filtration gave 10g of a white solid in 69.6% yield.
Example 6
In the synthesis example, heterocyclic compound 100 is synthesized, and the technical route is as follows:
Figure BDA0003133166080000131
synthesis of compound 100: in a three-necked flask, 100-1(15g, 44.8mmol), NaOBu-t (9g, 86mmol) and toluene (150mL) were added, the system was replaced with nitrogen, the reaction mixture was heated to 70 ℃ and Pd was added2(dba)3(0.15g, 1% w/w) and t-Bu3P (1.5g, 10% w/w), nitrogen substitution. 100-2(4.6g, 22.2mmol) was dissolved in 40mL of toluene and slowly added dropwise. After the addition, the system was heated to 110 ℃ and reacted for 3 hours. After the reaction was completed, the reaction solution was cooled to 50 ℃, silica gel was passed through the reaction solution, and the reaction solution was rinsed with 150mL of toluene, and the obtained filtrate was concentrated to remove half of the volume, and 100mL of ethanol was added thereto, followed by stirring at room temperature for 1 hour. After filtration, compound 100 was obtained as a white solid (12g, yield 75.4%).
Example 7
In the synthesis example, heterocyclic compound 103 is synthesized, and the technical route is as follows:
Figure BDA0003133166080000132
compound (I)Synthesis of 103-3: in a three-necked flask, 103-2(15g, 71.4mmol) and NaOBu-t (14.8g, 142mmol) were added, toluene (100mL) was then added, the system was replaced with nitrogen, the reaction mixture was heated to 70 ℃ and Pd was added2(dba)3(0.15g, 1% w/w) and t-Bu3P (1.5g, 10% w/w), nitrogen substitution. 103-1(19.1g, 70mmol) was dissolved in 120mL of toluene and slowly added dropwise. After the addition, the system was heated to 110 ℃ and reacted for 3 hours. After the reaction, the reaction solution was cooled to 50 ℃, the reaction solution was passed through silica gel, rinsed with 200mL of toluene, the resulting filtrate was concentrated to remove half of the volume, 150mL of ethanol was added, and the mixture was stirred at room temperature for 1 hour. After filtration, Compound 103-3 was obtained as a white solid (20g, yield 70.9%).
Synthesis of compound 103: in a three-necked flask, 103-3(15g, 37.2mmol), NaOBu-t (7.8g, 74.4mmol) and toluene (100mL) were added, the system was purged with nitrogen, the reaction mixture was heated to 70 ℃ and Pd was added2(dba)3(0.15g, 1% w/w) and t-Bu3P (1.5g, 10% w/w), nitrogen substitution. 103-4(13.4g, 40mmol) was dissolved in 100mL of toluene and slowly added dropwise. After the addition, the system was heated to 110 ℃ and reacted for 3 hours. After the reaction was completed, the reaction solution was cooled to 50 ℃, silica gel was passed through the reaction solution, and the reaction solution was rinsed with 150mL of toluene, and the obtained filtrate was concentrated to remove half of the volume, and 150mL of ethanol was added thereto, followed by stirring at room temperature for 1 hour. After filtration, compound 103 was obtained as a white solid (18g, yield 73.6%).
The invention also provides application of the heterocyclic compound in an organic electroluminescent device, and particularly provides the heterocyclic compound as a material of a covering layer in the organic electroluminescent device. The following device examples prepared organic electroluminescent devices comprising a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode; and a capping layer disposed on the surfaces of the first and second electrodes opposite to the surface of the organic material layer, wherein the heterocyclic compound as a material of the capping layer may be prepared using a common method and material for preparing an organic electroluminescent device. When the organic electroluminescent device is manufactured, the heterocyclic compound may be formed as the capping layer using a solution coating method, which means spin coating, dip coating, ink-jet printing, screen printing, a spray method, roll coating, and the like, as well as a vacuum deposition method. The organic electroluminescent device may be of a top emission type, a bottom emission type, or a dual emission type, and the organic material layer thereof may be of a single layer structure, or may be of a multilayer structure in which two or more organic material layers are laminated, for example, may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as the organic material layer. Device examples 1 to 19 preparation of single-color organic electroluminescent device structures using red, green or blue light, heterocyclic compounds 1, 4, 11, 21, 34, 41, 52, 68, 80, 88, 92, 98, 103, 107, 113, 25, 60, 86 and 100 were used as the capping layer materials, respectively.
Device example 1
The blue light organic electroluminescent device is manufactured according to the structure shown in figure 1, and the preparation process comprises the following steps: a transparent anode ITO film layer was formed on a glass substrate 101 to a film thickness of 150nm to obtain a first electrode 102 as an anode, and then vapor deposition was performed
Figure BDA0003133166080000141
And compounds
Figure BDA0003133166080000142
The mixed material of (2) as the hole injection layer 103 was mixed at a ratio of 3:97 (mass ratio), and then a compound having a thickness of 100nm was deposited by evaporation
Figure BDA0003133166080000143
A first hole transport layer 104 was obtained, and then a compound having a thickness of 20nm was evaporated
Figure BDA0003133166080000151
A second hole transport layer 105 was obtained and then evaporated at an evaporation rate of 95:5
Figure BDA0003133166080000152
And
Figure BDA0003133166080000153
30nm, fabricating a blue light emitting unit 106, and evaporating to deposit 10nm
Figure BDA0003133166080000154
Forming an electron blocking layer 107, and then
Figure BDA0003133166080000155
And
Figure BDA0003133166080000156
an electron transport layer 108 having a thickness of 30nm was formed at a mixing ratio of 4:6 (mass ratio), and then magnesium silver having a thickness of 15nm (mass ratio of 1: 9) was formed as a second electrode 109, and then a layer 110 was formed thereon by evaporating 60nm of the heterocyclic compound 1 prepared in synthesis example 1 as a capping layer material.
Device examples 2 to 19 blue organic electroluminescent devices were fabricated using the heterocyclic compounds 4, 11, 21, 34, 41, 52, 68, 80, 88, 92, 98, 103, 107, 113, 25, 60, 86, 100 prepared in synthesis examples, respectively, instead of the heterocyclic compound 1 used in device example 1, and comparative examples 1 to 4 were fabricated to use the heterocyclic compounds 4, 11, 21, 34, 41, 52, 68, 80, 88, 92, 98, 103, 107, 113, 25, 60, 86, 100 prepared in synthesis examples, respectively, to replace the heterocyclic compound 1 used in device example 1, respectively
Figure BDA0003133166080000157
Figure BDA0003133166080000158
A blue organic electroluminescent device was fabricated in place of the heterocyclic compound 1 used in device example 1, and the obtained organic electroluminescent device was subjected to performance tests of voltage, efficiency, and service life, as specifically shown in table 1.
TABLE 1
Figure BDA0003133166080000161
As can be seen from Table 1, the organic electroluminescent device obtained by using the anthryl/phenanthryl-containing heterocyclic compound of the present invention as a capping layer material has high luminous efficiency, low driving voltage and long service life.

Claims (10)

1. A heterocyclic compound having a structure as shown in chemical formula 1 or chemical formula 2:
[ chemical formula 1]
Figure FDA0003133166070000011
[ chemical formula 2]
Figure FDA0003133166070000012
Wherein, in chemical formula 1 and chemical formula 2,
X1is N;
X2to X6Are the same or different from each other, are each independently selected from C or N, and at least one is N;
ar is an aromatic ring or an aromatic heterocyclic ring having 5 to 30 carbon atoms;
R1from- (L)1)m-A1Represents:
L1is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene;
m is an integer of 0 to 10, and when m is not less than 2, L1Are the same or different from each other;
A1is a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
2. The heterocyclic compound according to claim 1, wherein chemical formula 1 or chemical formula 2 is represented by any one of the following chemical structures:
Figure FDA0003133166070000013
3. the heterocyclic compound according to claim 1, wherein chemical formula 1 or chemical formula 2 is represented by a chemical structure of any one of chemical formulae 3 to 8:
[ chemical formula 3], [ chemical formula 4] and [ chemical formula 5] are, in order:
Figure FDA0003133166070000021
[ chemical formula 6], [ chemical formula 7], and [ chemical formula 8] are, in order:
Figure FDA0003133166070000022
in chemical formulas 3 to 8, X1To X6And R1Are the same as chemical formula 1 or chemical formula 2.
4. The heterocyclic compound according to any one of claims 1 to 3, wherein L is1Is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 1 to 60 carbon atoms; a. the1Is a substituted or unsubstituted alkylamino group having 1 to 40 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylamine group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 1 to 60 carbon atoms.
5. The heterocyclic compound according to claim 1, which is selected from any one of the following chemical structures numbered 1 to 115:
Figure FDA0003133166070000031
Figure FDA0003133166070000041
Figure FDA0003133166070000051
Figure FDA0003133166070000061
6. use of the heterocyclic compound of any of claims 1 to 5 in an organic electroluminescent device.
7. Use according to claim 6, wherein the heterocyclic compound is used as a capping layer material for the organic electroluminescent device.
8. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode;
further comprising a covering layer provided on a surface of the first electrode and the second electrode opposite to the surface of the organic material layer, wherein the heterocyclic compound according to any one of claims 1 to 6 is used as a material of the covering layer.
9. A display panel comprising the organic electroluminescent device according to claim 8.
10. A display device comprising the display panel of claim 9.
CN202110711690.1A 2021-06-25 2021-06-25 Heterocyclic compounds and their use in organic electroluminescent devices Pending CN113444112A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202110711690.1A CN113444112A (en) 2021-06-25 2021-06-25 Heterocyclic compounds and their use in organic electroluminescent devices

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202110711690.1A CN113444112A (en) 2021-06-25 2021-06-25 Heterocyclic compounds and their use in organic electroluminescent devices

Publications (1)

Publication Number Publication Date
CN113444112A true CN113444112A (en) 2021-09-28

Family

ID=77812907

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202110711690.1A Pending CN113444112A (en) 2021-06-25 2021-06-25 Heterocyclic compounds and their use in organic electroluminescent devices

Country Status (1)

Country Link
CN (1) CN113444112A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113735793A (en) * 2021-09-24 2021-12-03 长春海谱润斯科技股份有限公司 Compound containing benzo five-membered heterocycle and organic electroluminescent device thereof
CN114105873A (en) * 2021-11-19 2022-03-01 武汉天马微电子有限公司 Organic compound and application thereof

Citations (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106279148A (en) * 2015-05-22 2017-01-04 上海和辉光电有限公司 Promote OLED high temperature, the material of high current density performance and application thereof
CN106831743A (en) * 2016-12-30 2017-06-13 上海天马有机发光显示技术有限公司 A kind of electroluminescent organic material and organic photoelectric device
CN107513054A (en) * 2017-09-29 2017-12-26 江苏三月光电科技有限公司 It is a kind of using triazine and quinoxaline as the organic compound of core and its application on OLED
CN108178750A (en) * 2017-12-05 2018-06-19 烟台九目化学制品有限公司 A kind of preparation and its application of benzo [g] quinazoline derivative
KR20180119734A (en) * 2017-04-25 2018-11-05 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element comprising the same and electronic device thereof
CN109415324A (en) * 2016-07-06 2019-03-01 喜星素材株式会社 Heterocyclic compound and the organic light emitting apparatus for using this heterocyclic compound
CN109553620A (en) * 2017-09-25 2019-04-02 北京鼎材科技有限公司 General formula compound and organic electroluminescence device
CN109863614A (en) * 2016-10-25 2019-06-07 柯尼卡美能达株式会社 Organic electroluminescent device and organic electroluminescent material
CN109890937A (en) * 2016-10-12 2019-06-14 三星Sdi株式会社 For the compound of Organic photoelectronic components, Organic photoelectronic components and display device
KR20190075322A (en) * 2017-12-21 2019-07-01 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
CN109988160A (en) * 2017-12-29 2019-07-09 三星Sdi株式会社 Organic compound, composition, organic optoelectronic device and display device
CN110229145A (en) * 2019-03-28 2019-09-13 江苏三月光电科技有限公司 A kind of organic compound based on pyridine and its application on OLED
CN110483528A (en) * 2019-07-04 2019-11-22 浙江华显光电科技有限公司 A kind of novel phosphorescence host compound and the electroluminescent device using the compound
CN110903159A (en) * 2019-08-12 2020-03-24 宇瑞(上海)化学有限公司 Phenanthroline and phenanthroline derivative as core compound and OLED device prepared by taking phenanthroline and phenanthroline derivative as CPL layer
CN111100129A (en) * 2018-10-29 2020-05-05 北京夏禾科技有限公司 Organic electroluminescent material and device
CN111560009A (en) * 2020-05-28 2020-08-21 宁波卢米蓝新材料有限公司 Novel organic compound and organic light emitting diode including the same
CN111646983A (en) * 2019-12-30 2020-09-11 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN111995999A (en) * 2020-05-06 2020-11-27 浙江华显光电科技有限公司 Combination of deuterated guest compound and host compound and photoelectric device comprising same
CN112300144A (en) * 2019-07-30 2021-02-02 江苏三月光电科技有限公司 Organic compound based on carbazole as core and application of organic compound in OLED
US20210130383A1 (en) * 2019-11-05 2021-05-06 Luminescence Technology Corporation Organic electroluminescent material and device

Patent Citations (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106279148A (en) * 2015-05-22 2017-01-04 上海和辉光电有限公司 Promote OLED high temperature, the material of high current density performance and application thereof
CN109415324A (en) * 2016-07-06 2019-03-01 喜星素材株式会社 Heterocyclic compound and the organic light emitting apparatus for using this heterocyclic compound
CN109890937A (en) * 2016-10-12 2019-06-14 三星Sdi株式会社 For the compound of Organic photoelectronic components, Organic photoelectronic components and display device
CN109863614A (en) * 2016-10-25 2019-06-07 柯尼卡美能达株式会社 Organic electroluminescent device and organic electroluminescent material
CN106831743A (en) * 2016-12-30 2017-06-13 上海天马有机发光显示技术有限公司 A kind of electroluminescent organic material and organic photoelectric device
KR20180119734A (en) * 2017-04-25 2018-11-05 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element comprising the same and electronic device thereof
CN109553620A (en) * 2017-09-25 2019-04-02 北京鼎材科技有限公司 General formula compound and organic electroluminescence device
CN107513054A (en) * 2017-09-29 2017-12-26 江苏三月光电科技有限公司 It is a kind of using triazine and quinoxaline as the organic compound of core and its application on OLED
CN108178750A (en) * 2017-12-05 2018-06-19 烟台九目化学制品有限公司 A kind of preparation and its application of benzo [g] quinazoline derivative
KR20190075322A (en) * 2017-12-21 2019-07-01 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
CN109988160A (en) * 2017-12-29 2019-07-09 三星Sdi株式会社 Organic compound, composition, organic optoelectronic device and display device
CN111100129A (en) * 2018-10-29 2020-05-05 北京夏禾科技有限公司 Organic electroluminescent material and device
CN110229145A (en) * 2019-03-28 2019-09-13 江苏三月光电科技有限公司 A kind of organic compound based on pyridine and its application on OLED
CN110483528A (en) * 2019-07-04 2019-11-22 浙江华显光电科技有限公司 A kind of novel phosphorescence host compound and the electroluminescent device using the compound
CN112300144A (en) * 2019-07-30 2021-02-02 江苏三月光电科技有限公司 Organic compound based on carbazole as core and application of organic compound in OLED
CN110903159A (en) * 2019-08-12 2020-03-24 宇瑞(上海)化学有限公司 Phenanthroline and phenanthroline derivative as core compound and OLED device prepared by taking phenanthroline and phenanthroline derivative as CPL layer
US20210130383A1 (en) * 2019-11-05 2021-05-06 Luminescence Technology Corporation Organic electroluminescent material and device
CN111646983A (en) * 2019-12-30 2020-09-11 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN111995999A (en) * 2020-05-06 2020-11-27 浙江华显光电科技有限公司 Combination of deuterated guest compound and host compound and photoelectric device comprising same
CN111560009A (en) * 2020-05-28 2020-08-21 宁波卢米蓝新材料有限公司 Novel organic compound and organic light emitting diode including the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WEIGAO HU ET AL.: ""Synthesis of 2,3-Difunctionalized Benzofuran Derivatives through Palladium-Catalyzed Double Isocyanide Insertion Reaction"", 《ORGANIC LETTERS》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113735793A (en) * 2021-09-24 2021-12-03 长春海谱润斯科技股份有限公司 Compound containing benzo five-membered heterocycle and organic electroluminescent device thereof
CN113735793B (en) * 2021-09-24 2022-12-13 长春海谱润斯科技股份有限公司 Compound containing benzo five-membered heterocycle and organic electroluminescent device thereof
CN114105873A (en) * 2021-11-19 2022-03-01 武汉天马微电子有限公司 Organic compound and application thereof

Similar Documents

Publication Publication Date Title
CN107011182B (en) Novel compound and organic electronic device comprising same
CN113429353B (en) Naphthyridine derivative-containing compound and application thereof
CN113717059B (en) Organic compound, electronic element containing organic compound and electronic device
CN111440122A (en) Thermally activated delayed fluorescence material and organic light emitting device
CN109336834A (en) A kind of aryl amine derivatives and its organic electroluminescence device
CN111848417A (en) Organic electroluminescent compound of benzanthracene derivative and preparation method and application thereof
CN111620890A (en) Compound, organic electronic device comprising same, and display device or lighting device
CN113683580A (en) Amine compound containing fluoranthene derivative and organic electroluminescent device comprising same
CN116283909B (en) Organic electronic transmission material and preparation method and application thereof
CN113444112A (en) Heterocyclic compounds and their use in organic electroluminescent devices
CN107759559B (en) Compound and organic electronic device thereof
CN111635413A (en) Compound, organic electronic device comprising same, and display device or lighting device
CN115557920A (en) Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device
CN117355530A (en) Heterocyclic compound, organic light-emitting element comprising same, and composition for organic layer
KR102003366B1 (en) Heterocyclic compound and organic light emitting device comprising the same
CN112500298B (en) Arylamine compound and organic electroluminescent device
CN113845505A (en) Spirofluorene derivative amine compound and organic electroluminescent device comprising same
CN116583506A (en) Organic light-emitting compound and organic electroluminescent element comprising same
CN112759524A (en) Aromatic amine derivative and organic electroluminescent device thereof
CN113563204B (en) Triarylamine compound and application thereof in organic electroluminescent display device
CN113582909B (en) Large steric hindrance carbazole compound and application thereof in organic electroluminescent display device
CN114437108B (en) N-containing spiro organic compound and application thereof in organic light-emitting device and panel
KR102040745B1 (en) Novel compound and organic electronic device comprising the same
CN116813598A (en) Organic electroluminescent compound and organic electroluminescent device
CN114874191A (en) Organic luminescent material and preparation method 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
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20210928