CN106220652A - New Organic Electro Luminescent Materials and the organic light emitting diode device of this luminescent material of use - Google Patents
New Organic Electro Luminescent Materials and the organic light emitting diode device of this luminescent material of use Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- 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
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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Abstract
The present invention relates to new Organic Electro Luminescent Materials and use the organic light emitting diode device of this luminescent material, belonging to organic electronic field of luminescent technology.The new Organic Electro Luminescent Materials of the present invention, its structural formula is Formulas I, one of II, III, during wherein Y is expressed as following carbazole quinoline group one, X is expressed as hydrogen, the aromatic group of substituted or unsubstituted carbon number 6 30, the heteroaromatic group of substituted or unsubstituted carbon number 5 30, Y Yu X are bonded to five yuan or hexatomic ring, and in described heterocycle, hetero atom is N, S, O.Experiment shows, the new Organic Electro Luminescent Materials of the present invention is the phosphorescent compound with high triplet energy, use described phosphorescent compound as the main body of the luminescent layer of Organic Light Emitting Diode, thereby promote the energy transfer in luminescent layer, and improve green emission efficiency and the service life of organic luminous layer.
Description
Technical field
The present invention relates to a kind of new Organic Electro Luminescent Materials and a kind of Organic Light Emitting Diode (OLED) device, more
For body, relate to a kind of because of high triplet energy and wide bandgap, there is the novel electroluminescent of the luminous efficiency of raising
Material and a kind of OLED using this new Organic Electro Luminescent Materials.
Background technology
In recent years, organic electroluminescence device had been carried out widely studied and exploitation.Basic at this light-emitting component
In structure, the layer containing luminescent substance is inserted between pair of electrodes, by, on applying voltage to this element, obtaining from shiner
The light emission of matter.
Owing to this light-emitting component is self-emission device, therefore they relative to liquid crystal display in high pixel observability and
Save the aspect to backlight demand and there is advantage, the most such as, be deemed suitable for flat panel displaying element.Light-emitting component is equally
Ceiling advantage, because they are thin and lightweight.Response very at a high speed is one of feature of this element.
Additionally, due to this light-emitting component can be formed in the form of a film, planar light emission therefore can be provided.Therefore,
Can be readily formed and there is large-area element.This is to be difficult to use the point source with electric filament lamp and LED as representative or with fluorescence
Lamp is the feature of the linear light sorurce acquisition of representative.Therefore, light-emitting component also has big potentiality as can be applicable to the flat of illumination
Area source etc..
The excited state formed by organic compound can be singletstate or triplet state.From singlet excited state (S*)
Transmitting is fluorescence, and from triplet excited states (T*) transmitting be referred to as phosphorescence.Additionally, it is believed that its statistics is raw in light-emitting component
Become ratio for S*:T*=1:3.It is being in photoemissive compound by the energy conversion of singlet excited state, is not the most seeing
Observe the transmitting from triplet excited states, and only observe the transmitting from singlet excited state.It is therefore contemplated that use glimmering
The interior two word efficiency of the light-emitting component of optical compounds have the theoretical limit of 25%, are based upon the S of 1:3*With T*Ratio.Therefore have
Machine electromechanical phosphorescent material is the class material recently attracted attention, and the organic electroluminescence with high luminous efficiency and luminosity is sent out
Luminescent material, it, by the method introducing heavy metal atom, make use of under room temperature the triplet transition originally prohibited, so that internal
Quantum efficiency theory can reach 100%, be single fluorescent material 4 times (1, Cao Y., Parker I.D., Heeger J.,
Nature,1999,397:414-417.2、Wohlgenann M.,et al.Nature,2001,409:494-497.).Organic
The heavy metal atom that electromechanical phosphorescent material is conventional mostly is transition metal, wherein with iridium most widely used, research is the most detailed, this is
Because metal iridium complex has under high efficiency, room temperature stronger phosphorescent emissions and can be by the adjustment of ligand structure
Regulation emission wavelength makes the color of electroluminescent device cover whole visible region.Therefore design studies synthesizing new is golden
Belonging to complex of iridium, split phosphorescing materia is significant.
But, the efficiency of adulterant acutely reduces because of Quenching, thus for the luminescence of the adulterant without main body
There is restriction in layer.Accordingly, it is desirable to carry out shape by adulterant and the main body with more high thermal stability and triplet energy state
Become luminous material layer.
In the OLED comprising phosphorescent compound, the hole from anode and the electronics from negative electrode are at luminescent material
Combine at the main body of layer.There is the singlet exciton singletstate to adulterant or the energy level transition of triplet of main body, and
Carry out the triplet excitons energy level transition to the triplet of adulterant of autonomous agent.Transit to the singletstate energy of adulterant
The exciton of level transits to the triplet of adulterant again.The exciton transition of the triplet of adulterant, to ground state, makes to send out
Photosphere is luminous.
For realizing transitting to the high-effect order transition of adulterant, the triplet energy state of main body should be more than three lines of adulterant
State energy.When the triplet of main body is less than the triplet energy state of adulterant, occur by adulterant to main body energy is anti-
Transition, makes luminous efficiency reduce.
The CBP being widely used in main body has the triplet of 2.6eV, there are about-6.3eV can level, peace treaty-
The lowest energy level of 2.8eV.Hence with triplet 2.8eV, can level-5.8eV and the blue light of lowest energy level-3.0eV
Adulterant FCNIr, it may occur that the anti-transition of energy level of adulterant to main body, makes luminous efficiency reduce.Particularly, luminous efficiency reduces
Generation the most notable.
Summary of the invention
The present invention relates to a kind of new Organic Electro Luminescent Materials and a kind of this new Organic Electro Luminescent Materials that uses
OLED, both solve the one or more problems caused because of restriction and the defect of prior art substantially.
It is an object of the present invention to provide a kind of new Organic Electro Luminescent Materials, described novel electroluminescent
Material has high triplet energy state and wide band gap, and strong electron transport ability.
It is a further object to provide a kind of OLED with higher photoluminescence efficiency.
The new Organic Electro Luminescent Materials of the present invention, its structural formula is Formulas I, one of II, III:
During wherein X is expressed as following carbazole quinoline isomer one, 9 atom N and Y keyed jointing in carbazole quinoline group,
Y is expressed as the aromatic group of substituted or unsubstituted carbon number 6-30, substituted or unsubstituted carbon number 5-
Phenyl ring on the heteroaromatic group of 30, Y Yu X is bonded to five yuan or hexatomic ring, and in described heterocycle, hetero atom is N, S, O.
Described Y is one of following groups:
Described substituted group is the alkyl of C1-C4.
Described Y is substituted or unsubstituted hexatomic ring or five-membered ring, and described Y Yu X is bonded to five yuan or hexatomic ring.
The structure that described Y with X is bonded to five yuan or hexatomic ring is as follows:
Preferential: the atom N in structural formula I, II, III and the C atom keyed jointing on phenyl in carbazole quinoline.
Preferably: structural formula I, II, its atom N and the C atom keyed jointing on phenyl 6 in carbazole quinoline.
Preferred compound is:
Organic light emitting diode device prepared by above-mentioned material.
Experiment shows, the new Organic Electro Luminescent Materials of the present invention is the phosphorescent compound with high triplet energy,
Use described phosphorescent compound as the main body of the luminescent layer of Organic Light Emitting Diode, thereby promote the energy in luminescent layer
Transfer, and improve green emission efficiency and the service life of organic luminous layer.
Accompanying drawing explanation
D intermediate nuclear-magnetism in Fig. 1, main body one.
Fig. 2, the nuclear-magnetism of main body one intermediate E.
Fig. 3, main body one DSC.
Fig. 4, Comparative Example D SC.
Detailed description of the invention
The present invention provides New Phosphorus optical compounds preparation method, for making the purpose of the present invention, technical scheme, effect more clear
Clear, complete, the following is the further description to the present invention.Should be appreciated that embodiment herein only for explaining the present invention,
Be not limiting as the present invention, all meet the scope of the invention all within protection.
The preparation of embodiment the 1, first main body
The synthesis of intermediate C:
0.1mol A, 0.2mol B, sodium tert-butoxide 0.2mol, 0.002mol palladium is separately added into 2L four-hole bottle, 1L first
Benzene adds 2L four-hole bottle, stirring, inflated with nitrogen 30 minutes, adds 1ML tri-butyl phosphine, is heated to reflux 4 hours, cools down, filter
To mother solution.Concentrated mother liquor, obtains light yellow solid.Mass spectrum (ESI, 245.3)
Intermediate D (CAS:1800071-10-6, CN104725373 Phosphorescent compound,
Preparation method and organic light emitting diode device) synthesis:
0.1molC is dissolved in 300ML DMF, 50 degree of CLs, drips 0.1mol NBS, along with dropping, gradually separates out greyish white
Color solid.NBS drips off, and is stirred overnight, cold filtration, obtains pale solid D.Accompanying drawing 1 is shown in detection.
The synthesis of compound 1:
0.1mol D、0.1molE(14H-Benzo[c][1]benzothieno[2,3-a]carbazole,CAS:
1313395-18-4 is prepared according to patent US 20140332793 synthetic method) added 1L four-hole bottle, add toluene
400ML, sodium tert-butoxide 0.2mol, stirring, inflated with nitrogen, it is dividedly in some parts acid chloride 0.02mol, tri-butyl phosphine 0.04mol, nitrogen charging
Gas 30 minutes, backflow is overnight.Cooling, filters, and obtains light yellow solid, simple detection 565.69 (MODI-TOF)
The preparation of embodiment 2: the second main body
The synthesis of intermediate C:
0.1mol A, 0.2mol B, sodium tert-butoxide 0.2mol, 0.002mol palladium is separately added into 2L four-hole bottle, 1L first
Benzene adds 2L four-hole bottle, stirring, inflated with nitrogen 30 minutes, adds 1ML tri-butyl phosphine, is heated to reflux 4 hours, cools down, filter
To mother solution.Concentrated mother liquor, obtains light yellow solid C.Mass spectrum (ESI, 245.3)
The synthesis of intermediate D:
The synthesis of D is referred to document Journal of Organic Chemistry, 76 (9), 2976-2993；2011,
The synthetic method of 9,9-diphenylacridine synthesizes.
The synthesis of intermediate F:
0.1molC is dissolved in 300ML DMF, 50 degree of CLs, drips 0.1mol NBS, along with dropping, gradually separates out greyish white
Color solid.NBS drips off, and is stirred overnight, and cold filtration obtains pale solid.
The synthesis of compound 2:
0.1mol F、0.1mol(14H-Benzo[c][1]benzothieno[2,3-a]carbazole,CAS
1313395-18-4 is prepared according to patent US 20140332793 synthetic method) added 1L four-hole bottle, add toluene
400ML, ethanol 200ML, water 200ML, stirring, it is dividedly in some parts potassium carbonate 0.2mol, inflated with nitrogen 30 minutes, adds acid chloride
0.5G, tri-butyl phosphine 1ML, backflow is overnight.Cooling, filters, and obtains light yellow solid, simple detection 486.5 (MODI-TOF)
Embodiment the 3, the 3rd main body synthesizes
By 2,3-dibromo pyridine, as raw material, according to disclosed patent CN102612518 synthetic route, obtains chemical combination
Thing G.With reference to main body one, two synthetic method, obtain main body three.
Embodiment the 4, the 4th main body synthesizes
According to the synthetic route of main body two, methyl-magnesium-bromide replaces phenyl-magnesium-bromide, obtains material of main part four.
Embodiment the 5, the 5th main body
It is easy to prepare intermediate F according to patent US 20140332793, according to the synthetic method of embodiment 4, is led
Body five.
Comparative example:
2-(4-bromobenzene)-4,6-diphenyl-central Shanxi plain is as raw material, according to synthetic method above, it is easy to compared
Example compound.
Measure according to first to the 5th material of main part prepared by above-mentioned synthesis example of implementation of the present invention and by with
The material of the comparative example that lower chemical formula represents ultra-violet absorption spectrum under low temperature (such as, 77K) and photoluminescence spectra, it shows
Show in result table below.
Comparative example
Table 1:
| Energy level | LUMO(Ev) | HOMO(Ev) | Triplet (Ev) | |
| Comparative example | 2.65 | -3.20 | -5.85 | 2.50 |
| First main body | 2.75 | -3.35 | -6.10 | 2.65 |
| Second main body | 2.78 | -3.31 | -6.09 | 2.67 |
| 3rd main body | 2.82 | -3.30 | -6.12 | 2.71 |
| 4th main body | 2.90 | -3.33 | -6.23 | 2.73 |
| 5th main body | 2.87 | -3.35 | -6.17 | 2.77 |
As it can be seen from table 1 main body two is all higher than 2.65ev to main body five triplet state, red, green phosphorescent material can be met
The requirement of material main body.
Hereinafter describe use by above-mentioned second and the 3rd material of main part formed；Green glow phosphorescent compound and comparing
The material of example is as the manufacture example of the Organic Light Emitting Diode of green body.
Ito substrate is patterned so that it is light-emitting area 3mmX3mm, be then carried out.Ito substrate is put into very
After in empty room, making base pressure is 1X10-6Torr.Then, at the ITO for forming anode, form thickness and be about the HATCN use of 50 angstroms
In hole injection layer, formation thickness is about the NPD of 550 angstroms and is about the TAPC of 100 angstroms uses for hole transmission layer, formation thickness
In hole injection layer, form thickness and be about second material of main part of 300 angstroms and doping content is about the GD of 15% for luminescent layer.
Then, form TmPyPb that thickness is 400 angstroms for electron supplying layer, form thickness and be about the LiF of 5 angstroms and inject for electronics
Layer, and form the Al layer negative electrode of 1100 angstroms.Then, use UV curable encapsulants and hygroscopic agent to be packaged operation, formed and send out
Optical diode.
Manufacture example 2
Use manufacturing process same as described above, manufacture Organic Light Emitting Diode, unique except for the difference that employing the 3rd main body
As light emitting host.
Comparative example
Use the technique identical with manufacturing example 1, manufacture Organic Light Emitting Diode, the most except for the difference that use comparative example main body
As light emitting host.
| Starting voltage (volt) | Luminous efficiency (Cd/A) | Launch wavelength (nm) | Life-span (95%) | |
| Embodiment 1 | 3.2 | 18.2 | 530 | 40000 hours |
| Embodiment 2 | 3.1 | 20.1 | 530 | 38000 hours |
| Comparative example | 4.5 | 15.3 | 531 | 28000 hours |
As shown in table 2, it has been confirmed that compared with comparative example, according to manufacturing the Organic Light Emitting Diode of example 1 manufacture in display
During the chromaticity coordinates of phase same level, demonstrate the improvement in luminous efficiency, quantum efficiency and service life.Particularly, greatly improve
The service life of Organic Light Emitting Diode.
As it has been described above, the implementation of the present invention has manufactured the phosphorescent compound with high triplet energy, and use institute
The phosphorescent compound stated, as the main body of the luminescent layer of Organic Light Emitting Diode, thereby promotes the energy transfer in luminescent layer,
And improve green emission efficiency and the service life of organic luminous layer.
Although embodiments of the present invention are illustrated by the description embodiment numerous with reference to it, but should
Understand, those skilled in the art can design by fall into many within the scope of disclosure principle other improvement and enforcement
Mode.More specifically, various changes and modifications theme combination within the disclosure, accompanying drawing and scope of the following claims
The composition part of arrangement and/or arrangement aspect are possible.Except constituting the changes and improvements partly and/or in terms of arrangement, replace
Transsexual application the most also will be apparent from.
Claims (10)
1. an electroluminescent organic material, its structural formula is Formulas I, one of II, III:
During wherein X is expressed as following carbazole quinoline isomer one, 9 atom N and Y keyed jointing in carbazole quinoline group,
Y is expressed as the aromatic group of substituted or unsubstituted carbon number 6-30, substituted or unsubstituted carbon number 5-30
Phenyl ring on heteroaromatic group, Y Yu X is bonded to five yuan or hexatomic ring, and in described heterocycle, hetero atom is N, S, O.
Electroluminescent organic material the most according to claim 1, described Y is one of following groups:
Electroluminescent organic material the most according to claim 1, described Y is substituted or unsubstituted hexatomic ring or five yuan
Ring, substituted group is the alkyl of C1-C4.
Electroluminescent organic material the most according to claim 1, described Y Yu X is bonded to five yuan or hexatomic ring.
Electroluminescent organic material the most according to claim 4, described Y Yu X is bonded to the structure of five yuan or hexatomic ring such as
Under:
Electroluminescent organic material the most according to claim 1, the atom N in structural formula I, II, III and benzene in carbazole quinoline
C atom keyed jointing on base.
Electroluminescent organic material the most according to claim 6, its structural formula is Formulas I, II, and the N in structural formula I, II is former
Son and the C atom keyed jointing on phenyl 6 in carbazole quinoline.
Electroluminescent organic material the most according to claim 7, its structural formula is:
9. an organic light emitting diode device, comprises the arbitrary described luminescent material of claim 1-8.
Organic light emitting diode device the most according to claim 9, the arbitrary described luminous material of described claim 1-8
Expect the material of main part as luminescent layer.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108570050A (en) * | 2018-05-08 | 2018-09-25 | 马鞍山南大高新技术研究院有限公司 | A kind of nitrogenous heterocyclic organic semiconducting materials and its application |
| CN110546780A (en) * | 2017-04-12 | 2019-12-06 | 柯尼卡美能达株式会社 | Coating liquid, method for producing coating liquid, coating film, and organic electroluminescent element |
| CN110759910A (en) * | 2018-12-06 | 2020-02-07 | 广州华睿光电材料有限公司 | Pyridine compound and use thereof |
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| US20160005979A1 (en) * | 2014-07-02 | 2016-01-07 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US20160013430A1 (en) * | 2014-07-10 | 2016-01-14 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US20160020412A1 (en) * | 2014-07-10 | 2016-01-21 | Samsung Display Co., Ltd. | Organic light-emitting device |
| CN105586030A (en) * | 2014-11-10 | 2016-05-18 | 三星显示有限公司 | Organic Light-Emitting Device |
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| US20150380662A1 (en) * | 2014-06-30 | 2015-12-31 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US20160005979A1 (en) * | 2014-07-02 | 2016-01-07 | Samsung Display Co., Ltd. | Organic light-emitting device |
| US20160013430A1 (en) * | 2014-07-10 | 2016-01-14 | Samsung Display Co., Ltd. | Organic light-emitting device |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110546780A (en) * | 2017-04-12 | 2019-12-06 | 柯尼卡美能达株式会社 | Coating liquid, method for producing coating liquid, coating film, and organic electroluminescent element |
| CN108570050A (en) * | 2018-05-08 | 2018-09-25 | 马鞍山南大高新技术研究院有限公司 | A kind of nitrogenous heterocyclic organic semiconducting materials and its application |
| CN110759910A (en) * | 2018-12-06 | 2020-02-07 | 广州华睿光电材料有限公司 | Pyridine compound and use thereof |
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