CN111892607A - N-heterobiphenyl organic compound and application thereof - Google Patents

N-heterobiphenyl organic compound and application thereof Download PDF

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CN111892607A
CN111892607A CN202010869423.2A CN202010869423A CN111892607A CN 111892607 A CN111892607 A CN 111892607A CN 202010869423 A CN202010869423 A CN 202010869423A CN 111892607 A CN111892607 A CN 111892607A
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CN111892607B (en
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刘营
姜东�
过宇阳
代文朋
李杨
邓东阳
张磊
高威
牛晶华
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Wuhan Tianma Microelectronics Co Ltd
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Shanghai Tianma AM OLED Co Ltd
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    • C07D487/22—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 four or more hetero rings
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    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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    • C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

Abstract

The invention provides an N-heterobiphenyl organic compound which has a structure shown in a formula I, a formula II or a formula III. The invention provides a series of compounds taking an N-heterobiphenyl structure as an electron accepting group, and the series of organic compounds are taken as main materials in an electroluminescent device and have higher triplet state energy level ETAnd larger molecular density, higher glass transition temperature and molecular thermal stability, effectively improves the balance migration of carriers, widens the exciton recombination area, and effectively improves the lightThe light-emitting efficiency and the service life of the device are greatly improved by the taking-out efficiency, and the device can be well applied to the technical field of electroluminescent devices.

Description

N-heterobiphenyl organic compound and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an N-heterobiphenyl organic compound and application thereof.
Background
Organic electroluminescent materials (OLEDs), as a new generation display technology, have the advantages of being ultra-thin, self-luminescent, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, low energy consumption, and the like, and have been widely used in the industries of flat panel display, flexible display, solid state lighting, vehicle-mounted display, and the like.
The light-emitting mechanism can be divided into two types, namely electroluminescence and electrophosphorescence. Fluorescence is the radiative decay transition of singlet excitons and phosphorescence is the light emitted by radiative decay of triplet excitons to the ground state. According to the spin quantum statistical theory, the formation probability ratio of singlet excitons to triplet excitons is 1: 3. The internal quantum efficiency of the fluorescent material is not more than 25 percent, and the external quantum efficiency is generally lower than 5 percent; the internal quantum efficiency of the electrophosphorescent material theoretically reaches 100%, and the external quantum efficiency reaches 20%. In 1998, the massecuite professor of Jilin university in China and the Forrest professor of Princeton university in USA respectively report that osmium complexes and platinum complexes are used as dyes to be doped into a light-emitting layer, the phosphorescence electroluminescence phenomenon is successfully obtained and explained for the first time, and the prepared phosphorescence material is creatively applied to an electroluminescence device.
Since the phosphorescent heavy metal material has a longer lifetime (μ s) and can cause triplet-triplet annihilation and concentration quenching under high current density, which leads to device performance attenuation, the heavy metal phosphorescent material is usually doped into a suitable host material to form a host-guest doped system, so that energy transfer is optimized, and luminous efficiency and lifetime are maximized. In the current research situation, the commercialization of heavy metal doped materials is mature, and it is difficult to develop alternative doped materials. Therefore, it is a common idea for researchers to place the center of gravity on the research and development of phosphorescent host materials.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide an N-biphenylene organic compound and an application thereof, wherein the prepared N-biphenylene organic compound is used as a host material in an electroluminescent device, such that the device has high light emitting efficiency and long lifetime.
The invention provides an N-heterobiphenyl organic compound which has a structure shown in a formula I, a formula II or a formula III:
Figure BDA0002650664950000021
wherein, A ring is independently selected from any one of the following groups:
Figure BDA0002650664950000022
X1、X2each independently selected from C-R12R13、N-R14O, S or P-R15；
R12～R15Independently selected from H, substituted or unsubstituted alkyl and derivatives thereof, substituted or unsubstituted alkoxy and derivatives thereof, substituted or unsubstituted aromatic ring and derivatives thereof, substituted or unsubstituted aromatic condensed ring and derivatives thereof, substituted or unsubstituted aromatic heterocycle and derivatives thereof, substituted or unsubstituted aromatic amine and derivatives thereof;
L1～L11each independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof;
R1～R11each independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof;
a. b, c, d, e, f, g, h, i, j and k are any integers independently selected from 0-3;
# denotes the fusion position.
The invention provides a display panel, which comprises an organic light-emitting device, wherein the organic light-emitting device comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, the organic thin film layer comprises a light-emitting layer, and the light-emitting layer contains at least one N-heterobiphenyl organic compound.
The invention provides a display device which comprises the display panel.
Compared with the prior art, the invention provides an N-heterobiphenyl organic compound which has a structure shown in a formula I, a formula II or a formula III. The invention provides a series of compounds taking an N-heterobiphenyl structure as an electron accepting group, and the series of organic compounds are taken as main materials in an electroluminescent device and have higher triplet state energy level ETAnd the organic electroluminescent device has higher molecular density, higher glass transition temperature and molecular thermal stability, effectively improves the balance migration of carriers, widens an exciton recombination region, and effectively improves the light extraction efficiency, so that the luminous efficiency and the service life of the device are greatly improved, and the organic electroluminescent device can be well applied to the technical field of electroluminescent devices.
Detailed Description
In order to further illustrate the present invention, the organic compounds of the N-heterobiphenyls and the applications thereof provided by the present invention are described in detail below with reference to examples.
The invention provides an N-heterobiphenyl organic compound which has a structure shown in a formula I, a formula II or a formula III:
Figure BDA0002650664950000041
wherein, A ring is independently selected from any one of the following groups:
Figure BDA0002650664950000042
X1、X2each independently selected from C-R12R13、N-R14O, S or P-R15；
R12～R15Independently selected from H, substituted or unsubstituted alkyl and derivatives thereof, substituted or unsubstituted alkoxy and derivatives thereof, substituted or unsubstituted aromatic ring and derivatives thereof, substituted or unsubstituted aromatic condensed ring and derivatives thereof, substituted or unsubstituted aromatic heterocycle and derivatives thereof, substituted or unsubstituted aromatic amine and derivatives thereof;
L1～L11each independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof;
R1～R11each independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof;
a. b, c, d, e, f, g, h, i, j and k are any integers independently selected from 0-3;
# denotes the fusion position.
According to the invention, an indole ring is condensed in the structure of the carbazole heterocyclic compound, and the introduction of an indole group not only expands the ring of the carbazole heterocyclic compound, but also forms a conjugated structure with the carbazole heterocyclic group, so that the electron cloud arrangement of the carbazole heterocyclic compound is changed, the hole injection and hole transmission performance of the material is obviously improved, and the hole mobility is effectively improved.
Furthermore, a specific electron-withdrawing group is adopted for substitution, and the bipolar main body material with excellent electrical performance and energy level matching can be obtained by combining and matching with other electron-withdrawing groups, so that the charge balance is facilitated; the luminous area is effectively widened, the luminous efficiency is improved, and the service life of the device is prolonged.
Alternative to the invention, R12～R15Independently selected from H, substituted or unsubstituted C1-C10 alkyl and derivatives thereof, substituted or unsubstituted C1-C10 alkoxy and derivatives thereof, substituted or unsubstituted C6-C40 aromatic ring and derivative groups thereof, substituted or unsubstituted C6-C40 aromatic condensed ring and derivative groups thereof, substituted or unsubstituted C5-C40 aromatic heterocyclic ring and derivative groups thereof, and substituted or unsubstituted C6-C40 aromatic amine and derivative groups thereof.
Alternative to the invention, R12～R15Independently selected from H, substituted or unsubstituted C1-C10 alkyl and derivatives thereof, and substituted or unsubstituted six-membered aromatic ring and derivatives thereof.
Alternative to the invention, R12～R15Independently selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl.
Alternative to the invention, R12～R15Independently selected from H, methyl or phenyl.
In some embodiments of the invention, R12～R15Independently selected from phenyl.
Optionally, of the invention, said L1～L11Each independently selected from single bond, substituted or non-substituted aromatic ring of C6-C40 and derivative group thereof, substituted or non-substituted aromatic condensed ring of C6-C40 and derivative group thereof, and substituted or non-substituted aromatic heterocyclic ring of C5-C40 and derivative group thereof.
Optionally, of the invention, said L1～L11Each independently selected from single bond, substituted or unsubstituted six-membered aromatic ring and derivative group thereof, substituted or unsubstituted C6-C20 aromatic condensed ring and derivative group thereof, and substituted or unsubstitutedFive-membered or six-membered aromatic heterocyclic ring and derivative group thereof.
Optionally, the single bond, substituted or unsubstituted phenyl and its derivatives, substituted or unsubstituted biphenyl and its derivatives, substituted or unsubstituted naphthyl and its derivatives, substituted or unsubstituted quinolyl and its derivatives, substituted or unsubstituted isoquinolyl and its derivatives, substituted or unsubstituted anthracenyl and its derivatives, substituted or unsubstituted phenanthryl and its derivatives, substituted or unsubstituted pyrenyl and its derivatives, substituted or unsubstituted pyridyl and its derivatives, substituted or unsubstituted pyrimidyl and its derivatives, substituted or unsubstituted triazinyl and its derivatives.
Alternative to the invention, R1～R11Each independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, and substituted or unsubstituted arylamine and derivative group thereof.
Alternative to the invention, R1～R11Each independently selected from H, substituted or unsubstituted aromatic ring of C6-C40 and derivative group thereof, substituted or unsubstituted aromatic condensed ring of C6-C40 and derivative group thereof, substituted or unsubstituted aromatic heterocyclic ring of C5-C40 and derivative group thereof, and substituted or unsubstituted aromatic amine of C6-C40 and derivative group thereof.
Alternative to the invention, R1～R11Each independently selected from H, substituted or unsubstituted six-membered aromatic ring and derivative group thereof, substituted or unsubstituted C6-C20 aromatic condensed ring and derivative group thereof, substituted or unsubstituted five-membered or six-membered aromatic heterocyclic ring and derivative group thereof, and substituted or unsubstituted C6-C20 arylamine and derivative group thereof.
Alternative to the invention, R1～R11Each independently selected from H, substituted or unsubstituted phenyl and its derivatives, substituted or unsubstituted carbazolyl and its derivatives, substituted or unsubstituted triphenylamine and its derivatives, substituted or unsubstituted diphenylamine and its derivatives, substituted or unsubstituted acridine and its derivativesBiological, substituted or unsubstituted phenoxazinyl and derivatives thereof, substituted or unsubstituted phenothiazinyl and derivatives thereof, substituted or unsubstituted phenanthrolinyl and derivatives thereof.
Optionally, the substituted aromatic ring and its derivative group, substituted aromatic condensed ring and its derivative group, substituted aromatic heterocycle and its derivative group, substituted alkyl and its derivative, substituted alkoxy and its derivative, and the substituent of the substituted aromatic amine and its derivative group is selected from:
one or more of substituted or unsubstituted C6-C40 aromatic rings and derivative groups thereof, substituted or unsubstituted C6-C40 aromatic condensed rings and derivative groups thereof, substituted or unsubstituted C5-C40 aromatic heterocycles and derivative groups thereof, and substituted or unsubstituted C6-C40 aromatic amines and derivative groups thereof.
In an alternative embodiment of the present invention, the above substituents are selected from phenyl.
Optionally, a, b, c, d, e, f, g, h, i, j and k are any integer selected from 0-3 independently.
Optionally, a, b, c, d, e, f, g, h, i, j, k are independently selected from 0, 1, 2 or 3.
In the present invention, # denotes the fusion site.
Optionally, the above N-heterobiphenyl organic compound has a structure represented by formula I-A or formula I-B:
Figure BDA0002650664950000071
wherein M is1、M2Independently selected from C, N, O, S or P.
R19、R23Independently selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl.
Alternative to the invention, R19、R23Independently selected from H, methyl or phenyl.
Alternative to the invention, R19、R23Independently selected from phenyl.
Alternative to the invention, L16、L20Independently selected from substituted or non-substituted pyrimidyl and derivatives thereof, substituted or non-substituted pyridyl and derivatives thereof, substituted or non-substituted quinolyl and derivatives thereof, substituted or non-substituted isoquinolyl and derivatives thereof, substituted or non-substituted phenyl and derivatives thereof, substituted or non-substituted naphthyl and derivatives thereof, substituted or non-substituted biphenyl and derivatives thereof, substituted or non-substituted anthryl and derivatives thereof, substituted or non-substituted phenanthryl and derivatives thereof, and substituted or non-substituted pyrenyl and derivatives thereof.
Alternative to the invention, L16、L20Independently selected from any of the following groups:
Figure BDA0002650664950000081
in the above structural formula, # denotes the position bonded to the benzene ring;
Figure BDA0002650664950000082
is represented by the formula16Or R20The location of the connection.
Alternative to the invention, L17、L18、L21、L22Independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof.
Alternative to the invention, L17、L18、L21、L22Independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl.
Alternative to the invention, R16、R17、R18、R20、R21、R22Independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereofSubstituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, and substituted or unsubstituted arylamine and derivative group thereof.
Alternative to the invention, R16、R17、R18、R20、R21、R22Independently selected from H, substituted or unsubstituted phenyl and derivatives thereof, substituted or unsubstituted carbazolyl and derivatives thereof, substituted or unsubstituted triphenylamine and derivatives thereof, substituted or unsubstituted diphenylamine and derivatives thereof, substituted or unsubstituted acridine and derivatives thereof, substituted or unsubstituted phenoxazinyl and derivatives thereof, substituted or unsubstituted phenothiazinyl and derivatives thereof, substituted or unsubstituted phenanthroline and derivatives thereof.
The method is optional, and l, m, n, o, p and q are any integers of 0-3.
Optionally, l, m, n, o, p and q are 0, 1, 2 or 3.
In the present invention, the indole group is fused at a specific position of the carbazolo heterocyclic compound, and then L is added16、L20The position of the compound is connected with the specific electron-withdrawing substituent group, so that the whole structure has better charge balance, and the prepared compound has larger triplet state energy level ETAnd meanwhile, the organic photoelectric device has high density and high polarizability, and can improve the luminous efficiency, the chromaticity and the service life of the organic photoelectric device when being used as a phosphorescent light-emitting main body material.
Optionally, the above N-heterobiphenyl organic compound has a structure shown in formula ii-a:
Figure BDA0002650664950000091
wherein M is3Selected from C, N, O, S or P.
R27Selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl.
Alternative to the invention, R27Selected from H, methyl or phenyl.
Alternative to the invention, R27Selected from phenyl.
L24Selected from substituted or unsubstituted triazinyl and derivatives thereof, substituted or unsubstituted benzopyrimidinyl and derivatives thereof.
Alternative to the invention, L24Selected from any one of the following groups:
Figure BDA0002650664950000092
in the above structural formula, # denotes the position bonded to the benzene ring;
Figure BDA0002650664950000101
is represented by the formula24The location of the connection.
L25、L26Independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof.
Alternative to the invention, L25、L26Independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl.
R24、R25、R26Independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof.
Alternative to the invention, R24、R25、R26Independently selected from H, substituted or unsubstituted phenyl and its derivatives, substituted or unsubstituted carbazolyl and its derivatives, substituted or unsubstituted triphenylamine and its derivatives, substituted or unsubstituted diphenylamine and its derivatives, substituted or unsubstituted acridine and its derivatives, substituted or unsubstituted pyridineSubstituted or unsubstituted phenothiazinyl and its derivatives, substituted or unsubstituted phenanthrolinyl and its derivatives.
r, s and t are any integers of 0-3.
Optionally, r, s, and t are independently selected from 0, 1, 2, or 3.
In the present invention, an indole group is fused at the above-mentioned specific position of the carbazoloheterocyclic compound, and then L is added24The triazine group or the benzopyrimidinyl group and the derivative group thereof are connected at the position, so that the electron cloud density of the whole structure is balanced, and the prepared compound has a larger triplet state energy level ETAnd meanwhile, the organic photoelectric device has high density and high polarizability, and can improve the luminous efficiency, the chromaticity and the service life of the organic photoelectric device when being used as a phosphorescent light-emitting main body material. Experimental results show that the light-emitting device prepared by using the compound as a main material of a light-emitting layer has higher current efficiency and longer service life.
Optionally, the above N-heterobiphenyl organic compound has a structure shown in formula iii-a:
Figure BDA0002650664950000102
wherein M is4Selected from C, N, O, S or P.
R31Selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl.
Alternative to the invention, R31Selected from H, methyl or phenyl.
Alternative to the invention, R31Selected from phenyl.
L28Selected from substituted or unsubstituted triazinyl and derivatives thereof.
Alternative to the invention, L28Selected from the following groups:
Figure BDA0002650664950000111
in the above structural formula, # denotes the position bonded to the benzene ring;
Figure BDA0002650664950000112
is represented by the formula28The location of the connection.
L29、L30Independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof.
Alternative to the invention, L29、L30Independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl.
R28、R29、R30Independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof.
Alternative to the invention, R28、R29、R30Independently selected from H, substituted or unsubstituted phenyl and derivatives thereof, substituted or unsubstituted carbazolyl and derivatives thereof, substituted or unsubstituted triphenylamine and derivatives thereof, substituted or unsubstituted diphenylamine and derivatives thereof, substituted or unsubstituted acridine and derivatives thereof, substituted or unsubstituted phenoxazinyl and derivatives thereof, substituted or unsubstituted phenothiazinyl and derivatives thereof, substituted or unsubstituted phenanthroline and derivatives thereof.
u, v and w are any integer of 0-3.
Optionally, u, v, w are independently selected from 0, 1, 2 or 3.
In the present invention, an indole group is fused at the above-mentioned specific position of the carbazoloheterocyclic compound, and then L is added28The triazine group is connected in position, so that the electron cloud density of the whole structure is balanced, and the prepared compound hasHaving a larger triplet energy level ETAnd meanwhile, the organic photoelectric device has high density and high polarizability, and can improve the luminous efficiency, the chromaticity and the service life of the organic photoelectric device when being used as a phosphorescent light-emitting main body material. Experimental results show that the light-emitting device prepared by using the compound as a main material of a light-emitting layer has higher current efficiency and longer service life.
Optionally, the N-heterobiphenyl organic compound has any one of the following structures:
Figure BDA0002650664950000121
Figure BDA0002650664950000131
Figure BDA0002650664950000141
Figure BDA0002650664950000151
Figure BDA0002650664950000161
Figure BDA0002650664950000171
Figure BDA0002650664950000181
Figure BDA0002650664950000191
Figure BDA0002650664950000201
the invention provides a preparation method of the N-heterobiphenyl organic compound, which comprises the steps of taking a halogen substituted carbazole compound shown in a formula 1 and derivatives thereof as raw materials, and carrying out condensation reaction with a compound shown in a formula 2 to obtain the N-heterobiphenyl organic compound shown in a formula I;
or taking halogen substituted carbazole compound shown in formula 3 and derivatives thereof as raw materials, and carrying out condensation reaction with compound shown in formula 4 to obtain N hetero biphenyl organic compound shown in formula II;
or taking halogen substituted carbazole compound shown in formula 5 and derivatives thereof as raw materials, and carrying out condensation reaction with compound shown in formula 6 to obtain N hetero biphenyl organic compound shown in formula III;
Figure BDA0002650664950000202
wherein X is halogen;
L1～L9、a～i、R1～R9the scope of ring A is the same as above, and is not described herein.
The N-heterobiphenyl organic compound provided by the invention can be used as a main material, a doping material or an electron transport layer of an organic photoelectric device.
The invention provides a display panel, which comprises an organic light-emitting device, wherein the organic light-emitting device comprises an anode, a cathode and an organic thin film layer positioned between the anode and the cathode, the organic thin film layer comprises a light-emitting layer, and the light-emitting layer contains at least one N-heterobiphenyl organic compound.
In an alternative aspect of the present invention, the organic thin film layer includes an electron transport layer, and the electron transport layer contains at least one of the above N-biphenylyl organic compounds.
The organic light-emitting device provided by the invention can be an organic light-emitting device well known to those skilled in the art, and optionally comprises a substrate, an ITO anode, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light-emitting layer, a first electron transport layer, a second electron transport layer, a cathode (a magnesium-silver electrode, the mass ratio of magnesium to silver is 1:9) and a cap layer (CPL).
In the invention, the anode material of the organic light-emitting device can be selected from metal-copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum and the like and alloys thereof; such as metal oxide-indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), etc.; such as conductive polymers-polyaniline, polypyrrole, poly (3-methylthiophene), and the like, and in addition to the above materials that facilitate hole injection and combinations thereof, include known materials suitable for use as anodes.
In the invention, the cathode material of the organic light-emitting device can be selected from metal-aluminum, magnesium, silver, indium, tin, titanium and the like and alloys thereof; such as multi-layer metal material-LiF/Al, LiO2/Al、BaF2Al, etc.; in addition to the above materials and combinations thereof that facilitate electron injection, known materials suitable for use as cathodes are also included.
In an alternative embodiment of the present invention, the organic optoelectronic device, for example, the organic thin film layer in the organic light emitting device, has at least one light emitting layer (EML), and may further include other functional layers, including a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL).
In an alternative embodiment of the present invention, the organic light emitting device is prepared according to the following method:
an anode is formed on a transparent or opaque smooth substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer.
Alternatively, the organic thin layer may be formed by a known film forming method such as evaporation, sputtering, spin coating, dipping, ion plating, or the like.
The invention also provides a display device comprising the display panel.
In the present invention, an organic light emitting device (OLED device) may be used in a display device, wherein the organic light emitting display device may be a display screen of a mobile phone, a display screen of a computer, a display screen of a television, a display screen of a smart watch, a display panel of a smart car, a display screen of a VR or AR helmet, a display screen of various smart devices, and the like.
The following will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The following (tBu)3PHBF4Abbreviation for tri-tert-butylphosphine tetrafluoroborate.
Example 1
Step (1)
Figure BDA0002650664950000221
In a 250mL round-bottom flask, Compound A (15mmol), Compound B (10mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (35 mL)/ethanol (25mL) and aqueous potassium carbonate (15mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography to obtain the objective product P-1.
Step (2)
Under an argon (Ar) atmosphere, compound P-1(20mmol), compound C (10mmol), Pd (OAc)2(1.6mmol)，(tBu)3PHBF4(5mmol)，K2CO3(6mmol) was placed in a 250mL three-necked flask, which was then heated and refluxed in 150mL of toluene solvent for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was distilled off. The thus-obtained crude product was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane), and then, recrystallization was performed using a mixed solvent of toluene and hexane to obtain a solid compound P-2.
Characterization of the organic compound P-2: molecular formula C54H33N3；
ESI-MS (M/z) [ M +1 ] obtained by liquid-phase mass spectrometry]+: theoretical value 724.27, test value 724.50; yuanTheoretical values of elemental analysis: c89.60, H4.60, N5.81; test values are: c89.54, H4.65, N5.82.
Example 2
Figure BDA0002650664950000231
Compound P-1 was prepared according to the above procedure.
Under an argon (Ar) atmosphere, compound P-1(20mmol), compound E (10mmol), Pd (OAc)2(1.6mmol)，(tBu)3PHBF4(5mmol)，K2CO3(6mmol) was placed in a 250mL three-necked flask, which was then heated and refluxed in 150mL of toluene solvent for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was distilled off. The thus-obtained crude product was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane), and then recrystallized using a mixed solvent of toluene and hexane to obtain a solid compound P-3.
Characterization of the organic compound P-3: molecular formula C54H33N3；
ESI-MS (M/z) [ M +1 ] obtained by liquid-phase mass spectrometry]+: theoretical value 724.27, test value 724.45; theoretical value of elemental analysis: c89.60, H4.60, N5.81; test values are: c89.55, H4.67, N5.81.
Example 3
Figure BDA0002650664950000232
In a 250mL round-bottom flask, Compound A (15mmol), Compound D (10mmol) and Pd (PPh)3)4(0.3mmol) was added to a mixture of toluene (35 mL)/ethanol (25mL) and aqueous potassium carbonate (15mmol) (10mL) and the reaction was refluxed for 12h under a nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, and then filtered through a celite pad, and the filtrate was extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate, filtered and evaporated, and then the crude product was purified by silica gel column chromatography to obtain the objective product P-4.
Under an argon (Ar) atmosphere, compound P-4(20mmol), compound E (10mmol), Pd (OAc)2(1.6mmol)，(tBu)3PHBF4(5mmol)，K2CO3(6mmol) was placed in a 250mL three-necked flask, which was then heated and refluxed in 150mL of toluene solvent for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was distilled off. The thus-obtained crude product was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane), and then recrystallized using a mixed solvent of toluene and hexane to obtain a solid compound P-5.
Characterization of the organic compound P-5: molecular formula C63H38N6；
ESI-MS (M/z) [ M +1 ] obtained by liquid-phase mass spectrometry]+: theoretical value 879.32, test value 879.60; theoretical value of elemental analysis: c86.08, H4.36, N9.56; test values are: c86.11, H4.37, N9.52.
Example 4
Figure BDA0002650664950000241
Under an argon (Ar) atmosphere, compound P-4(20mmol), compound F (10mmol), Pd (OAc)2(1.6mmol)，(tBu)3PHBF4(5mmol)，K2CO3(6mmol) was placed in a 250mL three-necked flask, which was then heated and refluxed in 150mL of toluene solvent for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was distilled off. The thus-obtained crude product was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane), and then recrystallized using a mixed solvent of toluene and hexane to obtain a solid compound P-Y.
Characterization of the organic compounds P-Y: molecular formula C63H38N6；
ESI-MS (M/z) [ M +1 ] obtained by liquid-phase mass spectrometry]+: theoretical value 879.32, test value 879.50; theoretical value of elemental analysis: c86.08, H4.36, N9.56; test values are: c86.10, H4.38, N9.52.
Application example 1
This application example provides an OLED device, OLED device includes in proper order: the LED structure comprises a glass substrate, an Indium Tin Oxide (ITO) anode 15nm, a first hole transport layer 10nm, a second hole transport layer 95nm, a light-emitting layer 30nm, a first electron transport layer 35nm, a second electron transport layer 5nm, a cathode 15nm (a magnesium-silver electrode, the mass ratio of magnesium to silver is 1:9) and a cap layer (CPL)100 nm.
The preparation steps of the OLED device are as follows:
(1) cutting the glass substrate into sizes of 50mm × 50mm × 0.7mm, respectively performing ultrasonic treatment in isopropanol and deionized water for 30min, and cleaning for 10min by exposing to ozone; mounting the obtained glass substrate with the ITO anode on a vacuum deposition device;
(2) under the vacuum degree of 2 x 10 < -6 > Pa, a compound HAT-CN is evaporated on the ITO anode layer in vacuum, the thickness of the compound HAT-CN is 10nm, and the compound HAT-CN is used as a first hole transport layer;
(3) vacuum evaporating a compound TAPC on the first hole transport layer to form a second hole transport layer with the thickness of 95 nm;
(4) co-depositing a light-emitting layer on the hole transport layer, wherein the organic compound P-2 provided by the invention is used as a main material, and Ir (piq)2(acac) as doping material, P-2 and Ir (piq)2(acac) mass ratio 19:1, thickness 30 nm;
(5) a compound BCP is evaporated on the luminous layer in vacuum to be used as a first electron transport layer, and the thickness is 35 nm;
(6) a compound Alq3 is evaporated on the first electron transport layer in vacuum to be used as a second electron transport layer, and the thickness is 5 nm;
(7) a magnesium-silver electrode is evaporated on the second electron transport layer in vacuum to serve as a cathode, the mass ratio of Mg to Ag is 1:9, and the thickness is 15 nm;
(8) a compound CBP having a high refractive index was vacuum-deposited on the cathode to a thickness of 100nm and used as a cathode cover layer (cap layer).
The structure of the compound used in the OLED device is as follows:
Figure BDA0002650664950000261
application examples 2 to 8
The organic compound P-2 in step (4) in application example 1 was replaced with the compound shown in table 1, and the other preparation steps were the same as in application example 1.
Comparative example 1
This comparative example differs from application example 1 only in that the organic compound P-2 in step (4) was used in the same amount as the comparative compound
Figure BDA0002650664950000262
Replacement; the other preparation steps are the same.
Performance evaluation of OLED devices:
testing the current of the OLED device under different voltages by using a Keithley 2365A digital nano-voltmeter, and then dividing the current by the light-emitting area to obtain the current density of the OLED device under different voltages; testing the brightness and radiant energy flux density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; according to the current density and the brightness of the OLED device under different voltages, working voltage and current efficiency (Cd/A) under the same current density (10mA/cm2) are obtained, and Von is the starting voltage under the brightness of 1Cd/m 2; lifetime LT95 (under 50mA/cm2 test conditions) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance; specific data are shown in table 1.
TABLE 1
Figure BDA0002650664950000271
Figure BDA0002650664950000281
According to the embodiments, the structure of the N-heterobiphenyl organic compound is modified and used as a main material in an electroluminescent device, so that the luminous efficiency and the service life of the device are greatly improved.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.

Claims (11)

1. An N-heterobiphenyl organic compound having a structure represented by formula I, formula II or formula III:
Figure FDA0002650664940000011
wherein, A ring is independently selected from any one of the following groups:
Figure FDA0002650664940000012
X1、X2each independently selected from C-R12R13、N-R14O, S or P-R15；
R12～R15Independently selected from H, substituted or unsubstituted alkyl and derivatives thereof, substituted or unsubstituted alkoxy and derivatives thereof, substituted or unsubstituted aromatic ring and derivatives thereof, substituted or unsubstituted aromatic condensed ring and derivatives thereof, substituted or unsubstituted aromatic heterocycle and derivatives thereof, substituted or unsubstituted aromatic amine and derivatives thereof;
L1～L11each independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof;
R1～R11each independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof;
a. b, c, d, e, f, g, h, i, j and k are any integers independently selected from 0-3;
# denotes the fusion position.
2. The Λ/-heterobiphenyl organic compound of claim 1, having the structure of formula i-a or formula i-B:
Figure FDA0002650664940000021
wherein M is1、M2Independently selected from C, N, O, S or P;
R19、R23independently selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl;
L16、L20independently selected from substituted or unsubstituted pyrimidyl and derivatives thereof, substituted or unsubstituted pyridyl and derivatives thereof, substituted or unsubstituted quinolyl and derivatives thereof, substituted or unsubstituted isoquinolyl and derivatives thereof, substituted or unsubstituted phenyl and derivatives thereof, substituted or unsubstituted naphthyl and derivatives thereof, substituted or unsubstituted biphenyl and derivatives thereof, substituted or unsubstituted anthryl and derivatives thereof, substituted or unsubstituted phenanthryl and derivatives thereof, substituted or unsubstituted pyrenyl and derivatives thereof;
L17、L18、L21、L22independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof;
R16、R17、R18、R20、R21、R22independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof;
l, m, n, o, p and q are any integer of 0-3.
3. The Nheterobiphenyl organic compound of claim 2, wherein M is1、M2Independently selected from C, N, O, S or P;
R19、R23independently selected from H, methyl or phenyl;
l16 and L20 are independently selected from any one of the following groups:
Figure FDA0002650664940000031
L17、L18、L21、L22independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl;
R16、R17、R18、R20、R21、R22independently selected from H, substituted or unsubstituted phenyl and its derivatives, substituted or unsubstituted carbazolyl and its derivatives, substituted or unsubstituted triphenylamine and its derivatives, substituted or unsubstituted diphenylamine and its derivatives, substituted or unsubstituted acridine and its derivatives, substituted or unsubstituted phenoxazinyl and its derivatives, substituted or unsubstituted phenothiazinyl and its derivatives, substituted or unsubstituted phenanthroline and its derivatives;
l, m, n, o, p and q are any integer of 0-3;
# represents the position bonded to the benzene ring;
Figure FDA0002650664940000041
is represented by the formula16Or R20The location of the connection.
4. The Λ/-heterobiphenyl organic compound according to claim 1, having the structure of formula ii-a:
Figure FDA0002650664940000042
wherein M is3Selected from C, N, O, S or P;
R27selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl;
L24selected from substituted or unsubstituted triazinyl and derivatives thereof, substituted or unsubstituted benzopyrimidinyl and derivatives thereof;
L25、L26independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof;
R24、R25、R26independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereof, substituted or unsubstituted aromatic heterocycle and derivative group thereof, substituted or unsubstituted arylamine and derivative group thereof;
r, s and t are any integers of 0-3.
5. The Nheterobiphenyl organic compound of claim 4, wherein M is3Selected from C, N, O, S or P;
R27selected from H, methyl or phenyl;
L24selected from any one of the following groups:
Figure FDA0002650664940000051
L25、L26independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl;
R24、R25、R26independently selected from H, substituted or unsubstituted phenyl and its derivatives, substituted or unsubstituted carbazolyl and its derivatives, substituted or unsubstituted triphenylamine and its derivatives, substituted or unsubstituted diphenylamine and its derivatives, substituted or unsubstituted acridine and its derivatives, substituted or unsubstituted phenoxazinyl and its derivatives, substituted or unsubstituted phenothiazinyl and its derivatives, substituted or unsubstituted phenanthroline and its derivatives;
r, s and t are any integers of 0-3;
# represents the position bonded to the benzene ring;
Figure FDA0002650664940000052
is represented by the formula24The location of the connection.
6. The Λ/-heterobiphenyl organic compound according to claim 1, having the structure of formula iii-a:
Figure FDA0002650664940000053
wherein M is4Selected from C, N, O, S or P;
R31selected from H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, phenyl;
L28selected from substituted or unsubstituted triazinyl and derivatives thereof;
L29、L30independently selected from single bond, substituted or non-substituted aromatic ring and derivative group thereof, substituted or non-substituted aromatic condensed ring and derivative group thereof, substituted or non-substituted aromatic heterocyclic ring and derivative group thereof;
R28、R29、R30independently selected from H, substituted or unsubstituted aromatic ring and derivative group thereof, substituted or unsubstituted aromatic condensed ring and derivative group thereofA group, a substituted or unsubstituted aromatic heterocycle and a derivative group thereof, a substituted or unsubstituted arylamine and a derivative group thereof;
u, v and w are any integer of 0-3.
7. The Nheterobiphenyl organic compound of claim 6, wherein M is4Selected from C, N, O, S or P;
R31selected from H, methyl or phenyl;
L28selected from the following groups:
Figure FDA0002650664940000061
L29、L30independently selected from single bond, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, pyridyl, pyrimidyl, quinolyl and isoquinolyl;
R28、R29、R30independently selected from H, substituted or unsubstituted phenyl and its derivatives, substituted or unsubstituted carbazolyl and its derivatives, substituted or unsubstituted triphenylamine and its derivatives, substituted or unsubstituted diphenylamine and its derivatives, substituted or unsubstituted acridine and its derivatives, substituted or unsubstituted phenoxazinyl and its derivatives, substituted or unsubstituted phenothiazinyl and its derivatives, substituted or unsubstituted phenanthroline and its derivatives;
u, v and w are any integer of 0-3;
# represents the position bonded to the benzene ring;
Figure FDA0002650664940000062
is represented by the formula28The location of the connection.
8. The Λ/-heterobiphenyl organic compound according to claim 1, having any of the following structures:
Figure FDA0002650664940000063
Figure FDA0002650664940000071
Figure FDA0002650664940000081
Figure FDA0002650664940000091
Figure FDA0002650664940000101
Figure FDA0002650664940000111
Figure FDA0002650664940000121
Figure FDA0002650664940000131
Figure FDA0002650664940000141
Figure FDA0002650664940000151
9. a display panel comprising an organic light emitting device comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode, the organic thin film layer comprising a light emitting layer containing at least one of the N-heterobiphenyl organic compounds according to any one of claims 1 to 8.
10. The display panel according to claim 9, wherein the organic thin film layer comprises an electron transport layer containing at least one of the N-heterobiphenyls organic compounds according to any one of claims 1 to 8.
11. A display device comprising the display panel according to any one of claims 9 to 10.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021153931A1 (en) * 2020-01-29 2021-08-05 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic device thereof
WO2022215580A1 (en) 2021-04-08 2022-10-13 日鉄ケミカル＆マテリアル株式会社 Light-emitting material, and organic electroluminescent element
CN115368370A (en) * 2021-05-20 2022-11-22 浙江虹舞科技有限公司 Condensed nitrogen heterocyclic compound, application thereof and organic electroluminescent device containing compound
EP4219497A1 (en) * 2022-01-26 2023-08-02 Samsung Display Co., Ltd. Heterocyclic compound, light-emitting device including the heterocyclic compound and electronic apparatus including the light-emitting device

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012234873A (en) * 2011-04-28 2012-11-29 Konica Minolta Holdings Inc Organic electroluminescent element material, organic electroluminescent element, display device, and lighting device
CN102822174A (en) * 2010-03-25 2012-12-12 默克专利有限公司 Materials for organic electroluminescence devices
KR20150098977A (en) * 2014-02-21 2015-08-31 주식회사 두산 Organic compounds and organic electro luminescence device comprising the same
CN104471020B (en) * 2012-07-10 2017-03-08 默克专利有限公司 Material for organic electroluminescence device
CN107922424A (en) * 2015-09-10 2018-04-17 罗门哈斯电子材料韩国有限公司 Organic electroluminescent compounds and the Organnic electroluminescent device for including the compound
CN111269239A (en) * 2020-03-09 2020-06-12 杨曦 Organic compound and application thereof in organic electronic device

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102822174A (en) * 2010-03-25 2012-12-12 默克专利有限公司 Materials for organic electroluminescence devices
JP2012234873A (en) * 2011-04-28 2012-11-29 Konica Minolta Holdings Inc Organic electroluminescent element material, organic electroluminescent element, display device, and lighting device
CN104471020B (en) * 2012-07-10 2017-03-08 默克专利有限公司 Material for organic electroluminescence device
KR20150098977A (en) * 2014-02-21 2015-08-31 주식회사 두산 Organic compounds and organic electro luminescence device comprising the same
CN107922424A (en) * 2015-09-10 2018-04-17 罗门哈斯电子材料韩国有限公司 Organic electroluminescent compounds and the Organnic electroluminescent device for including the compound
CN111269239A (en) * 2020-03-09 2020-06-12 杨曦 Organic compound and application thereof in organic electronic device

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021153931A1 (en) * 2020-01-29 2021-08-05 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic device thereof
WO2022215580A1 (en) 2021-04-08 2022-10-13 日鉄ケミカル＆マテリアル株式会社 Light-emitting material, and organic electroluminescent element
KR20230167351A (en) 2021-04-08 2023-12-08 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 Light-emitting materials, and organic electroluminescent devices
CN115368370A (en) * 2021-05-20 2022-11-22 浙江虹舞科技有限公司 Condensed nitrogen heterocyclic compound, application thereof and organic electroluminescent device containing compound
WO2022242521A1 (en) * 2021-05-20 2022-11-24 浙江虹舞科技有限公司 Condensed azacyclic compound, use thereof, and organic electroluminescent device comprising condensed azacyclic compound
EP4219497A1 (en) * 2022-01-26 2023-08-02 Samsung Display Co., Ltd. Heterocyclic compound, light-emitting device including the heterocyclic compound and electronic apparatus including the light-emitting device

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