CN106467554A - A kind of boracic organic electroluminescent compounds and its application - Google Patents
A kind of boracic organic electroluminescent compounds and its application Download PDFInfo
- Publication number
- CN106467554A CN106467554A CN201610617430.7A CN201610617430A CN106467554A CN 106467554 A CN106467554 A CN 106467554A CN 201610617430 A CN201610617430 A CN 201610617430A CN 106467554 A CN106467554 A CN 106467554A
- Authority
- CN
- China
- Prior art keywords
- formula
- aryl
- independently
- heteroaryl
- alkyl
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
Abstract
The invention discloses a kind of boracic organic electroluminescent compounds and its application, shown in the structural formula such as formula (1) of this compound.This compound has good fluorescence quantum efficiency and electroluminescent efficiency, easily forms armorphous thin film, has good heat stability, therefore such material can use as the luminescent layer dopant material in organic electroluminescence device or material of main part.
Description
Technical field
The present invention relates to technical field of semiconductors, especially relate to a kind of synthesis of fluorescent chemicalses, and as luminous
The application on Organic Light Emitting Diode of layer main body material or dopant material.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used to make
Make new display product it is also possible to be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting,
Application prospect is quite varied.
Currently, in smart mobile phone, the field such as panel computer obtains application to OLED Display Technique, further also will be to electricity
Depending on etc. large scale application extension.But, require to compare with the products application of reality, the luminous efficiency of OLED, use
The performances such as life-span also need to be lifted further.
OLED luminescent device just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it
Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes and collectively constitute OLED luminescent device together.
As current device, when the two end electrodes applied voltage to OLED luminescent device, and pass through electric field action organic layer functional material
Positive and negative charge in film layer, positive and negative charge is compound in luminescent layer further, that is, produce OLED electroluminescent.
High performance research is carried for OLED luminescent device include：Reduce the driving voltage of device, improve the luminous of device
Efficiency, improves service life of device etc..In order to realize the continuous lifting of the performance of OLED, not only need from OLED
Structure and the innovation of processing technology, constantly study with greater need for oled light sulfate ferroelectric functional material and innovate, formulate out higher performance OLED
Functional material.
The oled light sulfate ferroelectric functional material being applied to OLED can be divided into two big class from purposes, i.e. electric charge injection transmission
Material and luminescent material, further, also can inject charge into transmission material and be divided into electron injection transmission material and hole injection to pass
Luminescent material can also be divided into main body luminescent material and dopant material by defeated material.In order to make high performance OLED luminous organ
Part it is desirable to various organic functional material possesses good photoelectric characteristic, such as, as charge transport materials it is desirable to have good
Carrier mobility, high-vitrification conversion temperature etc., the material requirements material as luminescent layer has good fluorescent quantum
Efficiency, material evaporation stability, suitable HOMO/LUMO energy rank etc..
The oled light sulfate ferroelectric functional material film layer constituting OLED at least includes the above structure of two-layer, application in industry
OLED structure, then include multiple film layer such as hole injection layer, hole transmission layer, luminescent layer, electron injecting layer that is to say, that
The photoelectric functional material being applied to OLED includes at least hole-injecting material, hole mobile material, luminescent material, and electronics is noted
Enter material etc., material type and collocation form have rich and multifarious feature.In addition, the OLED device for different structure
For part collocation, the photoelectric functional material being used has stronger selectivity, and identical material is in different structure device
Performance is it is also possible to completely totally different.
At present, fluorescent material research aspect has been achieved for significant progress, disclosure satisfy that the demand of industrialization；Tradition has
Machine fluorescent material can only be lighted using 25% singlet exciton being electrically excited formation, and the internal quantum efficiency of device is relatively low (to be up to
25%) external quantum efficiency, is led to generally to be less than 5%；Particularly in terms of blue lifetime, still there is huge challenge.Cause
And, high efficiency, the research and development of long-life fluorescent material are always the focus of industrialization.
In addition, in host-guest system system, phosphor material or thermal excitation delayed fluorescence material (TADF) conduct are used
The OLED of object, material of main part needs high triplet energy state (T1), thus preventing energy from returning main body from guest materials
Material, improves the quantum efficiency of device.
Hot activation delayed fluorescence (TADF) material is the 3 of development after organic fluorescence materials and organic phosphorescent material
For luminous organic material.Such material typically has poor (the △ E of little singletstate-tripletST), triplet excitons can be led to
Cross anti-intersystem crossing be transformed into singlet exciton light.This can make full use of the singlet exciton being electrically excited lower formation and three lines
State exciton, the internal quantum efficiency of device can reach 100%.Meanwhile, material structure is controlled, stable in properties, and low price need not
Precious metal, in having a extensive future of OLEDs field.
Therefore, for the actual demand that current OLED shows Lighting Industry, the development of fluorescent material is also far from enough,
Lag behind the requirement of panel manufacturing enterprise, the organic functionses fluorescent material as material enterprise development higher performance seems particularly heavy
Will.
Content of the invention
The problems referred to above existing for prior art, the applicant provides a kind of organic electroluminescent compounds and its answers
With.The OLED that the compounds of this invention is produced as luminescent layer material of main part or dopant material has good outer quantum
Efficiency, stability of material and excitation, disclosure satisfy that the requirement of panel manufacturing enterprise.
Technical scheme is as follows：
The applicant provides a kind of boracic organic electroluminescent compounds, structure such as formula (1) institute of described compound
Show：
In formula (1), R1～R11Expression hydrogen independently, aryl, heteroaryl, alkyl, alkoxyl or aryl amine；
A1、A2Independently be expressed as alkyl, replacement or unsubstituted aryl or the heteroaryl that carbon number is 1～6
Base；
X is expressed as O, S, or N-R；R in wherein N-R is aryl, heteroaryl or aryl amine；
X can also be represented by formula (2)：
A3、A4Independently be expressed as alkyl, replacement or unsubstituted aryl or the heteroaryl that carbon number is 1～6
Base.
Preferably, described compound is represented by formula (3) or formula (4)：
In formula (3), (4), R1～R11Expression hydrogen independently, aryl, heteroaryl, alkyl, alkoxyl or arylamine
Base, but hydrogen can not be all shown as；
A1～A4Independently be expressed as the alkyl, cycloalkyl that carbon number is 1～6, replace or unsubstituted virtue
Base or heteroaryl；
R is expressed as aryl, heteroaryl or aryl amine.
Preferably, described compound is represented by formula (5), (6)；
In formula (5), R1～R3Expression hydrogen independently, aryl, heteroaryl, alkyl, alkoxyl or aryl amine, but
Hydrogen can not be all shown as；
A1～A4Independently be expressed as the alkyl, cycloalkyl that carbon number is 1～6, replace or unsubstituted virtue
Base or heteroaryl；
In formula (6), R is aryl, heteroaryl or aryl amine.
Preferably, R in described formula (1)1～R11At least one adopts formula (7) to represent：
In formula (7), R12、R13The substituted or unsubstituted phenyl of expression independently, pyridine radicals, dibiphenylyl, three
Phenyl, anthryl, phenanthryl, triazine radical, pyrimidine radicals, quinolyl, dibenzofuran group, 9,9- dimethyl fluorenyl, 9,9- diphenylfluorene
In base, carbazyl, benzo carbazole base, dibenzothiophenes base, bifurcation piperidinyl, indolocarbazole base, phenazinyl or thiazinyl
A kind of；
R12、R13Identical or different.
Preferably, R in described formula (1)1～R11At least one adopts formula (8) or formula (9) to represent：
In formula (8), X1For oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene of straight or branched alkyl replacement, aryl
One of tertiary amine groups that the alkylidene of replacement, alkyl or aryl replace；
R14、R15Independently be expressed as hydrogen, the alkyl of carbon atom 1-6, replacement or for replace phenyl or carbazole
Base；
R14、R15Can also be represented by formula (10)：
In formula (10), R16、R17The substituted or unsubstituted phenyl of expression independently, pyridine radicals, dibiphenylyl, three
Xenyl, anthryl, phenanthryl, triazine radical, pyrimidine radicals, quinolyl, dibenzofuran group, 9,9- dimethyl fluorenyl, 9,9- diphenyl
In fluorenyl, carbazyl, benzo carbazole base, dibenzothiophenes base, bifurcation piperidinyl, indolocarbazole base, phenazinyl or thiazinyl
One kind；R16、R17Identical or different.
Preferably, described R1～R11Independently be expressed as hydrogen, replacement or unsubstituted diaryl-amine group or nitrogenous
Multicomponent heterocycle aromatic group, but hydrogen can not be all shown as；
A1～A4Independently be expressed as the alkyl, cycloalkyl that carbon number is 1～6, replace or unsubstituted virtue
Base or heteroaryl；
R is aryl, heteroaryl or aryl amine.
Preferably, A in described formula1～A4Being expressed as independently：
In any one.
Preferably, described compound concrete structure is：
In any one.
The applicant additionally provides a kind of organic electroluminescence device containing described boracic organic electroluminescent compounds,
Described compound is applied to organic electroluminescent LED as luminous layer main body or dopant material.
Beneficial the having technical effect that of the present invention：
Compound of the present invention can be applicable to OLED luminescent device and makes, and can obtain good device performance,
When described compound uses as the independent emitting layer material of OLED luminescent device or luminescent layer dopant material, device
Luminous efficiency, power efficiency and external quantum efficiency are all greatly improved；Device color color purity be improved significantly, device lifetime obtains
To lifting.Compound of the present invention has good application effect in OLED luminescent device, before having good industrialization
Scape.
The present invention with boron atom as core, by by different aromatic structures in connection formed poly-ring aromatic compoundses,
Such material has higher triplet (T1) and can use as material of main part；Meanwhile, such material typically have little
Poor (the △ E of singletstate-tripletST), triplet excitons can be transformed into singlet exciton by anti-intersystem crossing and light,
Effectively improve device efficiency.Such material has higher glass transition temperature and decomposition temperature applies to organic light-emitting diodes
Guan Zhong, can effectively improve the life-span of device.
Brief description
The schematic diagram of the OLED that Fig. 1 makes for the compounds of this invention.
In figure：1st, transparent substrate layer, 2, ito anode layer, 3, hole injection layer, 4, hole transmission layer, 5, luminescent layer, 6, electricity
Sub- transport layer, 7, electron injecting layer, 8, negative electrode reflection electrode layer.
Specific embodiment
In order to more be apparent from technological means and the practical purpose of the present invention, by enumerating embodiment and comparative example,
It is aided with accompanying drawing to be illustrated simultaneously.
Embodiment 1 (compound 01)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 0.01mol intermediate A, 0.025mol phenylboric acid, 0.05 gram of pd
(pph3)4(four triphenyl phosphorus close palladium), each 60ml of toluene, ethanol, water, it is heated to reflux 15 hours, reaction is completely；Natural cooling, mistake
Filter, filtrate revolving, cross silicagel column, use toluene:Ethanol=2:1 (volume ratio) mixed solvent is pulled an oar, and obtains white solid after recrystallization
Body, purity (HPLC) is 98.5%, yield 70.6%.
Elementary analysiss structure (molecular formula C36H31B)：Theoretical value C, 91.14；H,6.59；B,2.28；
Test value：C,90.85；H,6.65；B,2.5.
Embodiment 2 (compound 07)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 0.01mol intermediate A, 0.025mol intermediate 1, uncle 0.03mol
Sodium butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 200ml toluene, it is heated to reflux 20 hours, reaction
Completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol=3:1 (volume ratio) mixed solvent is pulled an oar, weight
6.59 grams of white solids are obtained, purity (HPLC) is 98.6%, yield 65.8% after crystallization.
Elementary analysiss structure (molecular formula C66H57BN2O2)：Theoretical value C, 86.07；H,6.24；N,3.04；O, 3.47；B,
1.17
Test value：C,86.12；H,6.15；N,3.08；O,3.35；B,1.30.
Embodiment 3 (compound 18)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 0.01mol intermediate B, 0.025mol diphenylamine, 0.03mol
Sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 200ml toluene, it is heated to reflux 20 hours, instead
Should be completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol=3:1 (volume ratio) mixed solvent is pulled an oar,
6.59 grams of white solids are obtained, purity (HPLC) is 97.9%, yield 64.8% after recrystallization.
Elementary analysiss structure (molecular formula C45H35BN2O)：Theoretical value C, 85.71；H,5.59；N,4.44；O, 2.54；B,
1.71
Test value：C,85.62；H,5.58；N,4.48；O,2.35；B,1.97.
Embodiment 4 (compound 25)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 0.01mol intermediate A, 0.025mol intermediate 2, uncle 0.03mol
Sodium butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 200ml toluene, it is heated to reflux 20 hours, reaction
Completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol=3:1 (volume ratio) mixed solvent is pulled an oar, weight
White solid is obtained, purity (HPLC) is 98.05%, yield 63.8% after crystallization.
Elementary analysiss structure (molecular formula C72H53BN2O2)：Theoretical value C, 87.44；H,5.40；N,2.83；O, 3.24；B,
1.09
Test value：C,87.49；H,5.38；N,2.90；O,3,21；B,1.02.
Embodiment 5 (compound 31)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 0.01mol intermediate D, 0.012mol diphenylamine, 0.03mol
Sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 200ml toluene, it is heated to reflux 20 hours, instead
Should be completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol=3:1 (volume ratio) mixed solvent is pulled an oar,
White solid after recrystallization, purity (HPLC) is 97.85%, yield 62.8%.
Elementary analysiss structure (molecular formula C45H35BNS)：Theoretical value C, 83.58；H,5.46；N,4.33；S, 4.96；B,
1.67
Test value：C,83.49；H,5.58；N,4.32；S,4.92；B,1.69.
Embodiment 6 (compound 42)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 0.01mol intermediate E, double (3, the 4- dimethyl benzenes of 0.012mol
Base) amine, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 200ml toluene, heating
Backflow 20 hours, reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol=3:1 (volume ratio)
Mixed solvent is pulled an oar, white solid after recrystallization, and purity (HPLC) is 98.25%, yield 66.8%.
Elementary analysiss structure (molecular formula C76H66BN2)：Theoretical value C, 89.74；H,6.44；N,1.06；B,2.75
Test value：C,89.82；H,6.38；N,0.98；B,2.82.
Embodiment 7 (compound 46)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 0.01mol intermediate F, 0.025mol phenylboric acid, 0.05 gram of pd
(pph3)4(four triphenyl phosphorus close palladium), each 60ml of toluene, ethanol, water, it is heated to reflux 12 hours, reaction is completely；Natural cooling, mistake
Filter, filtrate revolving, cross silicagel column, use toluene:Ethanol=2:1 (volume ratio) mixed solvent is pulled an oar, and obtains white solid after recrystallization
Body, purity (HPLC) is 98.2%, yield 66.6%.
Elementary analysiss structure (molecular formula C46H35B)：Theoretical value C, 92.30；H,5.89；N,1.81；
Test value：C,92.15；H,5.95；N,1.90.
Embodiment 8 (compound 58)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, addition 0.025mol intermediate A, 0.01mol 3- carbazyl carbazole,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 200ml toluene, it is heated to reflux 20
Hour, reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol=3:1 (volume ratio) mixes molten
Agent is pulled an oar, white solid after recrystallization, and purity (HPLC) is 98.55%, yield 65.8%.
Elementary analysiss structure (molecular formula C72H51BN4)：Theoretical value C, 87.97；H,5.23；N,5.70；B,1.10
Test value：C,88.15；H,5.25；N,5.65；B,0.95.
Embodiment 9 (compound 59)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, addition 0.025mol intermediate A, 0.01mol 3- diphenylamine carbazole,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 200ml toluene, it is heated to reflux 20
Hour, reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol=3:1 (volume ratio) mixes molten
Agent is pulled an oar, white solid after recrystallization, and purity (HPLC) is 98.15%, yield 62.8%.
Elementary analysiss structure (molecular formula C72H55BN4)：Theoretical value C, 87.61；H,5.62；N,5.68；B,1.10
Test value：C,87.55；H,5.55；N,5.60；B,1.30.
Embodiment 10 (compound 62)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 0.01mol intermediate A, 0.025mol azophenlyene, uncle 0.03mol
Sodium butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 200ml toluene, it is heated to reflux 20 hours, reaction
Completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol=3:1 (volume ratio) mixed solvent is pulled an oar, weight
5.44 grams of white solids are obtained, purity (HPLC) is 98.2%, yield 64.8% after crystallization.
Elementary analysiss structure (molecular formula C48H37N2BO2)：Theoretical value C, 84.21；H,5.45；N,4.09；B,1.58；O,
4.67
Test value：C,84.14；H,5.25；N,4.13；B,1.62；O,4.86
Embodiment 11 (compound 71)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, adds 0.01mol intermediate G, 0.012mol3,6- diphenylamine fen
Piperazine, 0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 200ml toluene, it is heated to reflux
25 hours, reaction was completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol=3:1 (volume ratio) mixes
Solvent is pulled an oar, and obtains white solid after recrystallization, and purity (HPLC) is 98.35%, yield 64.7%.
Elementary analysiss structure (molecular formula C61H52N3BO)：Theoretical value C, 85.80；H,6.14；N,4.92；B,1.27；O,
1.87
Test value：C,85.90；H,6.07；N,4.87；B,1.24；O,1.92
Embodiment 12 (compound 76)
The concrete synthetic route of this compound is now provided：
The four-hole bottle of 250ml, under nitrogen protection, addition 0.01mol intermediate H, 0.012mol3,6- diphenylamine carbazole,
0.03mol sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphine, 200ml toluene, it is heated to reflux 20
Hour, reaction is completely；Natural cooling, filters, filtrate revolving, crosses silicagel column, uses toluene:Ethanol=3:1 (volume ratio) mixes molten
Agent is pulled an oar, and obtains white solid after recrystallization, and purity (HPLC) is 97.85%, yield 62.3%.
Elementary analysiss structure (molecular formula C63H47N4B)：Theoretical value C, 86.89；H,5.44；N,6.43；B,1.24
Test value：C,86.80；H,5.47；N,6.37；B,1.36
The compounds of this invention can use as luminous layer main body or dopant material, to the compounds of this invention 07, chemical combination
Thing 76, current material mCP carry out hot property, the mensure of luminescent spectrum, fluorescence quantum efficiency and cyclic voltammetric stability respectively,
Testing result is as shown in table 1.
Table 1
| Compound | Td(℃) | △Est(eV) | λPL(nm) | T1(eV) | Φf | Cyclic voltammetric stability |
| Compound 07 | 390 | 0.1850 | 460 | 2.82 | 60 | Excellent |
| Compound 76 | 420 | 0.1054 | 470 | 2.60 | 92 | Excellent |
| mCP | 360 | 0.7850 | 350 | 2.80 | 24 | Typically |
Note：Thermal weight loss temperature Td is in nitrogen atmosphere weightless 1% temperature, in the TGA-50H heat of Japanese Shimadzu Corporation
It is measured on weight analysis instrument, nitrogen flow is 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, open up Pu Kang using Japan
SR-3 spectroradiometer measures；Φ f is the solid powder fluorescence quantum efficiency (Maya2000Pro using U.S.'s marine optics
Fiber spectrometer, the test solid fluorescence amount of the C-701 integrating sphere of Lan Fei company of the U.S. and marine optics LLS-LED light source composition
Sub- efficiency test system, reference literature Adv.Mater.1997,9,230-232 method is measured)；Cyclic voltammetric stability
It is to be identified by the redox characteristic that cyclic voltammetry observes material；Test condition：Test sample is dissolved in volume ratio
For 2:1 dichloromethane and acetonitrile mixed solvent, concentration 1mg/mL, electrolyte is tetrabutyl ammonium tetrafluoroborate or the hexafluoro of 0.1M
The organic solution of phosphoric acid TBuA.Reference electrode is Ag/Ag+ electrode, is titanium plate to electrode, and working electrode is ITO electrode, follows
Ring number of times is 20 times.
From upper table data, the compounds of this invention has higher heat stability, has higher T1 energy level, has simultaneously
Have higher Φ f, the compounds of this invention can be applied to OLED as luminous layer main body or dopant material, device efficiency and
Life-span gets a promotion.
Describe the material of present invention synthesis below by way of comparative example 1,2 and embodiment 13～24 in detail in OLED
Application effect., compared with comparative example 1,2, the processing technology of device is identical, and is employed for described embodiment 13～24
Identical baseplate material and electrode material, the thickness of electrode material is also consistent, except that to used in device
Portion of material has carried out some adjustment, and comparative example 1,2 employs part OLED material of the present invention.
Comparative example 1
Transparent glass substrate 1, ito anode layer 2 (thickness is 150nm) are washed, carries out neutralizing treatment, pure water successively
Carry out ultraviolet-ozone again after washing, drying to wash to remove the organic residue on transparent ITO surface.
On the ito anode layer 2 having carried out after above-mentioned washing, using vacuum deposition apparatus, it is deposited with HAT-CN, its thickness
For 10nm, this layer of organic material uses as hole injection layer 3.And then evaporation 60nm thickness TCTA (4,4', 4 "-three (clicks
Azoles -9- base) triphenylamine) as hole transmission layer 4.
After above-mentioned hole mobile material evaporation terminates, make the luminescent layer 5 of OLED luminescent device, its structure includes OLED and sends out
The used material mCP of photosphere 5【9,9'- (1,3- phenyl) two -9H- carbazole】As material of main part, GD-19 as dopant material,
Doping ratio is 5% weight ratio, and luminescent layer thickness is 25nm.
After above-mentioned luminescent layer 5, continuation vacuum evaporation electron transport layer materials are Alq3(8-hydroxyquinoline aluminum).This material
The vacuum evaporation thickness of material is 30nm, and this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, make lithium fluoride (LiF) layer that thickness is 1nm, this layer is
Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, make aluminum (Al) layer that thickness is 80nm, this layer is negative electrode
Reflection electrode layer 8 uses.
As shown in table 2, test result is as shown in table 3 for made OLED light emitting device structure.Layers of material structure
As follows：
Comparative example 2
This comparative example is with comparative example 1 difference：GD-19 in the luminescent layer 5 of OLED luminescent device changes into
Real Ir (ppy)3.As shown in table 2, test result is as shown in table 3 for made OLED light emitting device structure.
After OLED luminescent device accomplished as described above, with known drive circuit, anode and negative electrode are coupled together, survey
The luminous efficiency of metering device, glow color, external quantum efficiency and device lifetime (LT95：Original intensity is arrived in brightness decay
95%).
Embodiment 13
The present embodiment is with comparative example 1 difference：MCP in the luminescent layer 5 of OLED luminescent device changes into chemical combination
Thing 01.As shown in table 2, test result is as shown in table 3 for made OLED light emitting device structure.
Embodiment 14
The present embodiment is with part with comparative example 1：MCP in the luminescent layer 5 of OLED luminescent device changes into compound
07.As shown in table 2, test result is as shown in table 3 for made OLED light emitting device structure.
Embodiment 15
The present embodiment is with comparative example 2 difference：MCP in the luminescent layer 5 of OLED luminescent device changes compound
46.As shown in table 2, test result is as shown in table 3 for made OLED light emitting device structure.
Embodiment 16
The present embodiment is with comparative example 3 difference：MCP in the luminescent layer 5 of OLED luminescent device changes into chemical combination
Thing 62.As shown in table 2, test result is as shown in table 3 for made OLED light emitting device structure.
Table 2
Table 3
Embodiment 17
The present embodiment is with comparative example 1 difference：GD-19 in the luminescent layer 5 of OLED luminescent device changes chemical combination
Thing 18.As shown in table 4, test result is as shown in table 5 for made OLED light emitting device structure.
Embodiment 18
The present embodiment is with comparative example 1 difference：GD-19 in the luminescent layer 5 of OLED luminescent device changes chemical combination
Thing 25.As shown in table 4, test result is as shown in table 5 for made OLED light emitting device structure.
Embodiment 19
The present embodiment is with comparative example 1 difference：GD-19 in the luminescent layer 5 of OLED luminescent device changes chemical combination
Thing 31.As shown in table 4, test result is as shown in table 5 for made OLED light emitting device structure.
Embodiment 20
The present embodiment is with comparative example 1 difference：GD-19 in the luminescent layer 5 of OLED luminescent device changes chemical combination
Thing 42.As shown in table 4, test result is as shown in table 5 for made OLED light emitting device structure.
Embodiment 21
The present embodiment is with comparative example 1 difference：GD-19 in the luminescent layer 5 of OLED luminescent device changes chemical combination
Thing 58.As shown in table 4, test result is as shown in table 5 for made OLED light emitting device structure.
Embodiment 22
The present embodiment is with comparative example 1 difference：GD-19 in the luminescent layer 5 of OLED luminescent device changes chemical combination
Thing 59.As shown in table 4, test result is as shown in table 5 for made OLED light emitting device structure.
Embodiment 23
The present embodiment is with comparative example 1 difference：GD-19 in the luminescent layer 5 of OLED luminescent device changes chemical combination
Thing 71.As shown in table 4, test result is as shown in table 5 for made OLED light emitting device structure.
Embodiment 24
The present embodiment is with comparative example 1 difference：GD-19 in the luminescent layer 5 of OLED luminescent device changes chemical combination
Thing 76.As shown in table 4, test result is as shown in table 5 for made OLED light emitting device structure.
Table 4
Table 5
Can be seen that compound of the present invention by the result of table 3 and table 5 to apply as material of main part or dopant material
Make in OLED luminescent device, and good device performance can be obtained.The luminous efficiency of device, external quantum efficiency all obtain
Very big improvement；Device lifetime is lifted clearly simultaneously.Compound of the present invention has good in OLED luminescent device
Application effect, and there is good industrialization prospect.
Although the present invention has been disclosed by embodiment and preferred implementation it should be appreciated that the invention is not restricted to institute's public affairs
The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute
The scope of attached claim should arrangement to cover all such modifications and be similar to consistent with explanation the widest.
Claims (9)
1. a kind of boracic organic electroluminescent compounds are it is characterised in that the structure such as formula (1) of described compound is shown：
In formula (1), R1～R11Expression hydrogen independently, aryl, heteroaryl, alkyl, alkoxyl or aryl amine；
A1、A2Independently be expressed as alkyl, replacement or unsubstituted aryl or the heteroaryl that carbon number is 1～6；
X is expressed as O, S, N-R or formula (2)；R in wherein N-R is aryl, heteroaryl or aryl amine；
A3、A4Independently be expressed as alkyl, replacement or unsubstituted aryl or the heteroaryl that carbon number is 1～6.
2. compound according to claim 1 is it is characterised in that described compound is represented by formula (3) or formula (4)：
In formula (3), (4), R1～R11Expression hydrogen independently, aryl, heteroaryl, alkyl, alkoxyl or aryl amine, but
It is to be all shown as hydrogen；
A1～A4Independently be expressed as the alkyl, cycloalkyl that carbon number is 1～6, replace or unsubstituted aryl or
Heteroaryl；
R is expressed as aryl, heteroaryl or aryl amine.
3. compound according to claim 1 is it is characterised in that described compound is represented by formula (5), (6)；
In formula (5), R1～R3Expression hydrogen independently, aryl, heteroaryl, alkyl, alkoxyl or aryl amine, but can not
It is all shown as hydrogen；
A1～A4Independently be expressed as the alkyl, cycloalkyl that carbon number is 1～6, replace or unsubstituted aryl or
Heteroaryl；
In formula (6), R is aryl, heteroaryl or aryl amine.
4. the compound according to any one of claims 1 to 3 is it is characterised in that R in described formula (1)1～R11At least one
Individual employing formula (7) represents：
In formula (7), R12、R13The substituted or unsubstituted phenyl of expression independently, pyridine radicals, dibiphenylyl, terphenyl,
Anthryl, phenanthryl, triazine radical, pyrimidine radicals, quinolyl, dibenzofuran group, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, click
One of oxazolyl, benzo carbazole base, dibenzothiophenes base, bifurcation piperidinyl, indolocarbazole base, phenazinyl or thiazinyl；
R12、R13Identical or different.
5. the compound according to any one of claims 1 to 3 is it is characterised in that R in described formula (1)1～R11At least one
Individual employing formula (8) or formula (9) represent：
In formula (8), X1For oxygen atom, sulphur atom, selenium atom, C1-10The alkylidene that straight or branched alkyl replaces, aryl replace
Alkylidene, one of the tertiary amine groups that replace of alkyl or aryl；
R14、R15Independently be expressed as hydrogen, the alkyl of carbon atom 1-6, replacement or for replace phenyl, carbazyl or formula
(10)；
In formula (10), R16、R17The substituted or unsubstituted phenyl of expression independently, pyridine radicals, dibiphenylyl, terphenyl
Base, anthryl, phenanthryl, triazine radical, pyrimidine radicals, quinolyl, dibenzofuran group, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl,
In carbazyl, benzo carbazole base, dibenzothiophenes base, bifurcation piperidinyl, indolocarbazole base, phenazinyl or thiazinyl one
Kind；R16、R17Identical or different.
6. the compound according to any one of claims 1 to 3 is it is characterised in that described R1～R11Being expressed as independently
Hydrogen, replacement or unsubstituted diaryl-amine group or nitrogenous multicomponent heterocycle aromatic group, but hydrogen can not be all shown as；
A1～A4Independently be expressed as the alkyl, cycloalkyl that carbon number is 1～6, replace or unsubstituted aryl or
Heteroaryl；
R is aryl, heteroaryl or aryl amine.
7. the compound according to any one of claims 1 to 3 is it is characterised in that A in described formula1～A4Independently
It is expressed as：
In any one.
8. compound according to claim 1 is it is characterised in that described compound concrete structure is：
In any one.
9. a kind of organic electroluminescence device containing described boracic organic electroluminescent compounds is it is characterised in that described chemical combination
Thing is applied to organic electroluminescent LED as luminous layer main body or dopant material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610617430.7A CN106467554A (en) | 2016-07-29 | 2016-07-29 | A kind of boracic organic electroluminescent compounds and its application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610617430.7A CN106467554A (en) | 2016-07-29 | 2016-07-29 | A kind of boracic organic electroluminescent compounds and its application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106467554A true CN106467554A (en) | 2017-03-01 |
Family
ID=58229916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610617430.7A Pending CN106467554A (en) | 2016-07-29 | 2016-07-29 | A kind of boracic organic electroluminescent compounds and its application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106467554A (en) |
Cited By (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180112722A (en) * | 2017-04-03 | 2018-10-12 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| WO2018203666A1 (en) * | 2017-05-02 | 2018-11-08 | 주식회사 엘지화학 | Novel compound and organic light emitting device using same |
| JP2018203622A (en) * | 2017-05-30 | 2018-12-27 | 学校法人関西学院 | Polycyclic aromatic compound having alkenyl group and polymer thereof |
| WO2019009687A1 (en) * | 2017-07-07 | 2019-01-10 | 주식회사 엘지화학 | Novel compound and organic light emitting element comprising same |
| KR20190037176A (en) * | 2017-09-28 | 2019-04-05 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| KR20190078541A (en) * | 2017-12-26 | 2019-07-04 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| CN110034234A (en) * | 2018-01-11 | 2019-07-19 | 北京鼎材科技有限公司 | A kind of white light organic electroluminescent device |
| WO2019239897A1 (en) * | 2018-06-14 | 2019-12-19 | 学校法人関西学院 | Electron transport material or electron injection material containing alkyl-substituted polycyclic aromatic compound |
| CN110590790A (en) * | 2019-08-29 | 2019-12-20 | 武汉华星光电半导体显示技术有限公司 | Hole transport material based on spiro triphenylamine, preparation method thereof and organic electroluminescent device |
| WO2020009467A1 (en) * | 2018-07-03 | 2020-01-09 | 주식회사 엘지화학 | Polycyclic compound and organic light emitting diode comprising same |
| KR20200080188A (en) * | 2018-12-26 | 2020-07-06 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| KR20200090137A (en) * | 2019-01-18 | 2020-07-28 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| WO2020218558A1 (en) * | 2019-04-26 | 2020-10-29 | 学校法人関西学院 | Compound, material for organic device, composition for forming light-emitting layer, organic field-effect transistor, organic thin-film solar cell, organic electroluminescent element, display device, and illumination device |
| KR20210010407A (en) * | 2019-07-19 | 2021-01-27 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| CN112442055A (en) * | 2019-08-30 | 2021-03-05 | 环球展览公司 | Organic electroluminescent material and device |
| CN112534593A (en) * | 2018-12-07 | 2021-03-19 | 株式会社Lg化学 | Organic light emitting diode |
| CN112940026A (en) * | 2021-02-02 | 2021-06-11 | 吉林奥来德光电材料股份有限公司 | Polycyclic compound and preparation method and application thereof |
| CN113594375A (en) * | 2020-04-30 | 2021-11-02 | 江苏三月光电科技有限公司 | Green light organic electroluminescent device |
| CN113748106A (en) * | 2019-06-10 | 2021-12-03 | Sfc株式会社 | Compound for organic light-emitting element and organic light-emitting element comprising same |
| CN113929709A (en) * | 2020-06-29 | 2022-01-14 | 江苏三月科技股份有限公司 | Boron-nitrogen-containing organic compound and organic electroluminescent device comprising same |
| KR20220021418A (en) | 2020-08-12 | 2022-02-22 | 가꼬우 호징 관세이 가쿠잉 | Polycyclic aromatic compounds |
| CN114144420A (en) * | 2019-07-23 | 2022-03-04 | Sfc株式会社 | Organic electroluminescent compounds and organic electroluminescent devices |
| US11299502B2 (en) | 2018-06-12 | 2022-04-12 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device including condensed cyclic compound |
| WO2022074616A1 (en) | 2020-10-09 | 2022-04-14 | Idemitsu Kosan Co., Ltd. | Heterocyclic compound and an organic electroluminescence device comprising the heterocyclic compound |
| US11393985B2 (en) | 2018-07-11 | 2022-07-19 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
| JP2022542130A (en) * | 2019-07-24 | 2022-09-29 | エスエフシー カンパニー リミテッド | Organic light-emitting compound and organic light-emitting device |
| US11502259B2 (en) | 2019-03-05 | 2022-11-15 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
| US11825733B2 (en) | 2019-01-11 | 2023-11-21 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
| US11919914B2 (en) | 2019-10-25 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11950492B2 (en) | 2019-01-29 | 2024-04-02 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103502252A (en) * | 2011-03-03 | 2014-01-08 | 国立大学法人九州大学 | Novel compound, charge transport material, and organic device |
| CN105431439A (en) * | 2014-02-18 | 2016-03-23 | 学校法人关西学院 | Polycyclic aromatic compound |
| EP2248869B1 (en) * | 2005-09-12 | 2016-06-29 | Merck Patent GmbH | Compounds for organic electronic devices |
-
2016
- 2016-07-29 CN CN201610617430.7A patent/CN106467554A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2248869B1 (en) * | 2005-09-12 | 2016-06-29 | Merck Patent GmbH | Compounds for organic electronic devices |
| CN103502252A (en) * | 2011-03-03 | 2014-01-08 | 国立大学法人九州大学 | Novel compound, charge transport material, and organic device |
| CN105431439A (en) * | 2014-02-18 | 2016-03-23 | 学校法人关西学院 | Polycyclic aromatic compound |
Non-Patent Citations (1)
| Title |
|---|
| ZHIGUO ZHOU ET AL.: "Planarized Triarylboranes: Stabilization by Structural Constraint and Their Plane-to-Bowl Conversion", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
Cited By (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180112722A (en) * | 2017-04-03 | 2018-10-12 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| KR102099002B1 (en) | 2017-04-03 | 2020-04-08 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| WO2018203666A1 (en) * | 2017-05-02 | 2018-11-08 | 주식회사 엘지화학 | Novel compound and organic light emitting device using same |
| KR20180122298A (en) * | 2017-05-02 | 2018-11-12 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| US11502261B2 (en) | 2017-05-02 | 2022-11-15 | Lg Chem Ltd. | Compound and organic light emitting device using the same |
| KR102053324B1 (en) | 2017-05-02 | 2019-12-06 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| JP2018203622A (en) * | 2017-05-30 | 2018-12-27 | 学校法人関西学院 | Polycyclic aromatic compound having alkenyl group and polymer thereof |
| JP7018171B2 (en) | 2017-05-30 | 2022-02-10 | 学校法人関西学院 | Polycyclic aromatic compounds with alkenyl groups and their multimers |
| CN110573516A (en) * | 2017-07-07 | 2019-12-13 | 株式会社Lg化学 | Novel compound and organic light emitting device comprising same |
| WO2019009687A1 (en) * | 2017-07-07 | 2019-01-10 | 주식회사 엘지화학 | Novel compound and organic light emitting element comprising same |
| CN110573516B (en) * | 2017-07-07 | 2023-07-28 | 株式会社Lg化学 | Compound and organic light emitting device comprising the same |
| KR20190037176A (en) * | 2017-09-28 | 2019-04-05 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| KR102112411B1 (en) * | 2017-09-28 | 2020-05-18 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| KR20190078541A (en) * | 2017-12-26 | 2019-07-04 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| KR102134523B1 (en) * | 2017-12-26 | 2020-07-16 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| CN110034234B (en) * | 2018-01-11 | 2023-09-05 | 北京鼎材科技有限公司 | White light organic electroluminescent device |
| CN110034234A (en) * | 2018-01-11 | 2019-07-19 | 北京鼎材科技有限公司 | A kind of white light organic electroluminescent device |
| US11299502B2 (en) | 2018-06-12 | 2022-04-12 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device including condensed cyclic compound |
| WO2019239897A1 (en) * | 2018-06-14 | 2019-12-19 | 学校法人関西学院 | Electron transport material or electron injection material containing alkyl-substituted polycyclic aromatic compound |
| JPWO2019239897A1 (en) * | 2018-06-14 | 2021-07-08 | 学校法人関西学院 | Electron-transporting or electron-injecting materials containing alkyl-substituted polycyclic aromatic compounds |
| WO2020009467A1 (en) * | 2018-07-03 | 2020-01-09 | 주식회사 엘지화학 | Polycyclic compound and organic light emitting diode comprising same |
| US11950504B2 (en) | 2018-07-03 | 2024-04-02 | Lg Chem, Ltd. | Polycyclic compound and organic light emitting diode comprising same |
| US11393985B2 (en) | 2018-07-11 | 2022-07-19 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
| CN112534593A (en) * | 2018-12-07 | 2021-03-19 | 株式会社Lg化学 | Organic light emitting diode |
| KR102316064B1 (en) | 2018-12-26 | 2021-10-22 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| KR20200080188A (en) * | 2018-12-26 | 2020-07-06 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| US11825733B2 (en) | 2019-01-11 | 2023-11-21 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
| KR102353148B1 (en) | 2019-01-18 | 2022-01-19 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| KR20200090137A (en) * | 2019-01-18 | 2020-07-28 | 주식회사 엘지화학 | Compound and organic light emitting device comprising same |
| US11950492B2 (en) | 2019-01-29 | 2024-04-02 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
| US11502259B2 (en) | 2019-03-05 | 2022-11-15 | Samsung Display Co., Ltd. | Organic electroluminescence device and polycyclic compound for organic electroluminescence device |
| WO2020218558A1 (en) * | 2019-04-26 | 2020-10-29 | 学校法人関西学院 | Compound, material for organic device, composition for forming light-emitting layer, organic field-effect transistor, organic thin-film solar cell, organic electroluminescent element, display device, and illumination device |
| CN113784972A (en) * | 2019-04-26 | 2021-12-10 | 学校法人关西学院 | Compound, material for organic device, composition for forming light-emitting layer, organic field-effect transistor, organic thin-film solar cell, organic electroluminescent element, display device, and lighting device |
| CN113748106B (en) * | 2019-06-10 | 2024-01-02 | Sfc株式会社 | Compound for organic light-emitting element and organic light-emitting element comprising same |
| CN113748106A (en) * | 2019-06-10 | 2021-12-03 | Sfc株式会社 | Compound for organic light-emitting element and organic light-emitting element comprising same |
| KR102413260B1 (en) * | 2019-07-19 | 2022-06-27 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| KR20210010407A (en) * | 2019-07-19 | 2021-01-27 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| CN114144420B (en) * | 2019-07-23 | 2024-03-26 | Sfc株式会社 | Organic electroluminescent compounds and organic electroluminescent device |
| CN114144420A (en) * | 2019-07-23 | 2022-03-04 | Sfc株式会社 | Organic electroluminescent compounds and organic electroluminescent devices |
| JP2022542130A (en) * | 2019-07-24 | 2022-09-29 | エスエフシー カンパニー リミテッド | Organic light-emitting compound and organic light-emitting device |
| JP7249465B2 (en) | 2019-07-24 | 2023-03-30 | エスエフシー カンパニー リミテッド | Organic light-emitting compound and organic light-emitting device |
| CN110590790A (en) * | 2019-08-29 | 2019-12-20 | 武汉华星光电半导体显示技术有限公司 | Hole transport material based on spiro triphenylamine, preparation method thereof and organic electroluminescent device |
| CN112442055A (en) * | 2019-08-30 | 2021-03-05 | 环球展览公司 | Organic electroluminescent material and device |
| US11919914B2 (en) | 2019-10-25 | 2024-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN113594375A (en) * | 2020-04-30 | 2021-11-02 | 江苏三月光电科技有限公司 | Green light organic electroluminescent device |
| CN113594375B (en) * | 2020-04-30 | 2023-12-01 | 江苏三月科技股份有限公司 | Green light organic electroluminescent device |
| CN113929709A (en) * | 2020-06-29 | 2022-01-14 | 江苏三月科技股份有限公司 | Boron-nitrogen-containing organic compound and organic electroluminescent device comprising same |
| KR20220021418A (en) | 2020-08-12 | 2022-02-22 | 가꼬우 호징 관세이 가쿠잉 | Polycyclic aromatic compounds |
| WO2022074616A1 (en) | 2020-10-09 | 2022-04-14 | Idemitsu Kosan Co., Ltd. | Heterocyclic compound and an organic electroluminescence device comprising the heterocyclic compound |
| CN112940026A (en) * | 2021-02-02 | 2021-06-11 | 吉林奥来德光电材料股份有限公司 | Polycyclic compound and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106467553B (en) | A kind of boracic organic electroluminescent compounds and its application in OLED device | |
| CN106467554A (en) | A kind of boracic organic electroluminescent compounds and its application | |
| CN109748898B (en) | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device | |
| CN106467523B (en) | A kind of organic aromatic compound and its application | |
| CN106467469A (en) | A kind of organic electroluminescent compounds and its application | |
| CN106543205B (en) | A kind of compound containing benzimidazole and its application on OLED | |
| CN106279203A (en) | Compound containing ketone and nitrogen heterocycle and application thereof in organic electroluminescent device | |
| CN106220609A (en) | A kind of compound with pyridine as core and the application on organic electroluminescence device thereof | |
| CN106220649A (en) | Diaryl ketone-based compound and application thereof in organic electroluminescent device | |
| CN106467482A (en) | A kind of compound based on diaryl ketone and its application | |
| CN106467468A (en) | A kind of organic compound with dibenzo heptene structure and its application | |
| CN106467740A (en) | A kind of organic electroluminescence fluorescent chemicalses and its application in electroluminescent device | |
| CN106467544A (en) | A kind of organic fluorescent compounds and its application | |
| CN106432158A (en) | Organic light emitting compound material and application thereof | |
| CN106749200A (en) | Ketone electroluminescent organic material of a kind of chromene 4 and its preparation method and application | |
| CN106749050B (en) | It is a kind of using cyclic diketones as the hot activation delayed fluorescence OLED material of core and its application | |
| CN106467518A (en) | A kind of organic electroluminescent compounds with nitrogenous five-ring heterocycles as core and its application | |
| CN106467458A (en) | A kind of compound based on diaryl ketone and its application on organic electroluminescence device | |
| CN109384726A (en) | A kind of organic luminescent compounds and preparation method thereof and organic electroluminescence device | |
| CN106467524B (en) | A kind of organic aromatic compound and its application on organic electroluminescence device | |
| CN106543071A (en) | A kind of compound with dibenzo heptenone as core and its application on OLED | |
| CN106467510A (en) | A kind of electroluminescent organic material and its application | |
| CN107056770A (en) | A kind of compound as core using nitrogenous five-ring heterocycles and its application on organic electroluminescence device | |
| CN106467511B (en) | It is a kind of using acridone as the compound of core and its application on organic electroluminescence device | |
| CN106467531A (en) | A kind of compound with nitrogenous five-ring heterocycles as core and its application |
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 | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20200331 Address after: 264006 No. 11 Wuzhishan Road, Yantai economic and Technological Development Zone, Shandong Applicant after: VALIANT Co.,Ltd. Address before: 214112 No. 210, Xinzhou Road, New District, Jiangsu, Wuxi Applicant before: JIANGSU SUNERA TECHNOLOGY Co.,Ltd. |
|
| TA01 | Transfer of patent application right | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170301 |
|
| RJ01 | Rejection of invention patent application after publication |