CN110256458A - A kind of thermal activation delayed fluorescence molecule and preparation method thereof, electroluminescent hot activation delayed fluorescence device - Google Patents
A kind of thermal activation delayed fluorescence molecule and preparation method thereof, electroluminescent hot activation delayed fluorescence device Download PDFInfo
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- CN110256458A CN110256458A CN201910571320.5A CN201910571320A CN110256458A CN 110256458 A CN110256458 A CN 110256458A CN 201910571320 A CN201910571320 A CN 201910571320A CN 110256458 A CN110256458 A CN 110256458A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent 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
Abstract
The invention discloses a kind of thermal activation delayed fluorescence molecules and preparation method thereof, electroluminescent hot activation delayed fluorescence device, thermal activation delayed fluorescence molecule includes electron donor and electron acceptor, wherein, electron acceptor dioxo containing the trimerization thiochromene ketone groups, the beneficial effects of the present invention are thermal activation delayed fluorescence molecules of the invention and preparation method thereof, electroluminescent hot activation delayed fluorescence device, wherein there are in thermal activation delayed fluorescence molecule trimerization dioxo thiochromene ketone groups, trimerization dioxo thiochromene ketone groups contain carbonyl structure, so that thermal activation delayed fluorescence molecule has high intersystem crossing rate constant and anti-intersystem crossing rate constant, the reduction of the radiation transistion rate as caused by energy gap rule can effectively be inhibited, to obtain high photoluminescence quantum yield.
Description
Technical field
The present invention relates to chemical field, in particular to a kind of thermal activation delayed fluorescence molecule and preparation method thereof, electroluminescent heat
Activate delayed fluorescence device.
Background technique
Organic Light Emitting Diode (organic lighting-emitting diodes, OLEDs), due to actively shining,
Visible angle is big, corresponding speed is fast, Acclimation temperature range is wide, driving voltage is low, small power consumption, brightness are big, simple production process, light
It is thin and can be with Flexible Displays the advantages that, OLED show and lighting area show huge application prospect, attracted scientific research work
The concern of author and company.Currently, Samsung, LG have been carried out OLEDs and apply on mobile phone.In OLED, emitting layer material
Superiority and inferiority be OLED can industrialization play a decisive role.Common emitting layer material is by subject and object luminescent material, and the material that shines
The luminous efficiency of material and service life are two important indicators of luminescent material quality.The OLED luminescent material of early stage is conventional fluorescent material
Material, since the exciton ratio of the singlet state in OLED and triplet is 1:3, and conventional fluorescent material can only utilize singlet excitons
It shines, therefore, the OLED theoretical internal quantum efficiency of conventional fluorescent material is 25%.Metal complex phosphor material is due to heavy atom
Quantum geometrical phase effect, so as to realize 100% utilization rate of singlet excitons and triplet exciton；And now
Also it has been used in feux rouges and green light OLED is shown.But phosphor material will usually use the valuable gold such as heavy metal Ir, Pt, Os
Belong to, it is not only at high cost, but also be more toxic.In addition, efficient, the long-life phosphorescent metal complex material is still greatly to choose
War.2012, Adachi et al. proposed the pure luminescent organic molecule of " thermal activation delayed fluorescence " (TADF) mechanism, by reasonable
D-A structure MOLECULE DESIGN so that molecule have lesser minimum singlet state and triple energy level difference (ΔsEST), such triplet swashs
Son can return to singlet state by anti-intersystem crossing (RISC), then be shone by radiation transistion to ground state, so as to simultaneously
Using list, triplet exciton, 100% utilization rate of exciton may be implemented, while not needing the participation of heavy metal.And TADF
Design on material structure is abundant, and material major part physical property is easy to adjust, and has to obtain meet the requirements efficient, long-life
Machine luminescent material.
For TADF material, small ΔESTAnd high photoluminescence quantum yield (PLQY) prepares high efficiency OLED
Necessary condition.Currently, green light and day blue light TADF material have obtained good external quantum efficiency (EQE)；But wavelength TADF
Material can not obtain excellent device performance since energy gap is regular (Energy gap law).
Summary of the invention
To solve the above-mentioned problems, the present invention provides a kind of thermal activation delayed fluorescence molecules and preparation method thereof, electroluminescent
Hot activation delayed fluorescence device is to solve to be confined to energy gap rule due to thermal activation delayed fluorescence molecule in the prior art
The problem of (Energy gap law) is to obtain excellent device performance.
The technical solution to solve the above problems is: the present invention provides a kind of thermal activation delayed fluorescence molecules, including electronics
Donor and electron acceptor, electron acceptor dioxo containing the trimerization thiochromene ketone groups.
Further, the molecular structural formula of electron acceptor includes one of following structural formula:
Further, the molecular structural formula of the electron donor includes one of following structural formula:
Further, when the structural formula of the electron donor is
The structural formula of electron acceptor is
The corresponding molecular formula of the thermal activation delayed fluorescence molecule are as follows:
It include that electron donor is provided and is had the present invention also provides a kind of preparation method of thermal activation delayed fluorescence molecule
The electron acceptor chemical combination of trimerization dioxo thiochromene ketone groups forms the thermal activation delayed fluorescence molecule.
Further, specific steps include by 3,9,15- tri- bromo- trimerization dioxo thiochromene ketone, 4- (diphenyl amino)-
In the Shrek bottle that phenyl boric acid, toluene and 2.5M wet chemical are added to, is carried out substituting gas with argon gas, it is molten to obtain first
Liquid.Four triphenyl phosphorus palladiums are added in first solution, 80 DEG C at a temperature of back flow reaction for 24 hours, obtain the second solution.
After being cooled to room temperature, second solution with methylene chloride is extracted, is washed, is dried, filtered and is spin-dried for obtain the 4th molten
Liquid；Column is carried out to the 4th solution with silica gel to chromatograph to obtain target compound.
Further, the leacheate of the column chromatography is the mixture of petroleum ether and methylene chloride.
The present invention also provides a kind of electroluminescent hot activation delayed fluorescence devices, with the thermal activation delayed fluorescence point
Son.
Further, electroluminescent hot activation delayed fluorescence device further includes substrate, and the substrate is the glass equipped with conductive film
Glass layer；Implanted layer is set on the substrate；Hole transmission layer is set on the implanted layer；Luminescent layer is set to the hole and passes
On defeated layer, the luminescent layer material therefor is the thermal activation delayed fluorescence molecule；Electron transfer layer is set to the luminescent layer
On；Cathode layer is set on the electron transfer layer.
Further, the material of the implanted layer is 2,3,6,7,10,11- six cyano-Isosorbide-5-Nitrae, 5,8,9,12- six pyridines
And it is luxuriant and rich with fragrance；The material of the hole transport is 4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyl) aniline]；The electron transfer layer
Material be 1,3,5- tri- (3- (3- pyridyl group) phenyl) benzene；The material of the cathode layer is lithium fluoride and aluminium.
The invention has the advantages that thermal activation delayed fluorescence molecule of the invention and preparation method thereof, electroluminescent hot activation delay
Fluorescent device has trimerization dioxo thiochromene ketone groups, trimerization dioxo thiochromene ketone group in thermal activation delayed fluorescence molecule
Carbonyl structure is contained in group, so that thermal activation delayed fluorescence molecule has high intersystem crossing rate constant and anti-intersystem crossing rate
Constant can effectively inhibit the reduction of the radiation transistion rate as caused by energy gap rule, to obtain high luminescence generated by light amount
Sub- yield.
Detailed description of the invention
The present invention is further explained with reference to the accompanying drawings and examples.
Fig. 1 is the fluorescence emission spectrum of the thermal activation delayed fluorescence molecule in embodiment 1.
Fig. 2 is the electroluminescent hot activation delayed fluorescence device schematic diagram in embodiment 2.
Fig. 3 is the electroluminescent hot activation delayed fluorescence device performance figure in embodiment 2.
In figure
1 electroluminescent hot activation delayed fluorescence device；
10 substrates；20 implanted layers；
30 hole transmission layers；40 luminescent layers；
50 electron transfer layers；60 cathode layers；
Specific embodiment
The explanation of following embodiment is to can be used to the particular implementation of implementation to illustrate the present invention with reference to additional schema
Example.Direction term that the present invention is previously mentioned, such as "upper", "lower", "front", "rear", "left", "right", "top", "bottom" etc. are only
With reference to the direction of annexed drawings.Therefore, the direction term used is to illustrate and understand the present invention, rather than to limit this hair
It is bright.
In the present embodiment, thermal activation delayed fluorescence molecule of the invention includes electron donor D and electron acceptor A, electronics by
Body A has trimerization dioxo thiochromene ketone groups, wherein the structure composition of thermal activation delayed fluorescence molecule is Dn- A formula structure, n
For natural number.As shown in Figure 1, for the fluorescence emission spectrum of the thermal activation delayed fluorescence molecule in this implementation.
The electron acceptor A has trimerization dioxo thiochromene ketone groups, since trimerization dioxo thiochromene ketone groups have
There is hydroxyl structure, so the thermal activation delayed fluorescence molecule has super plane, so that the thermal activation delayed fluorescence molecule
With high intersystem crossing rate constant and anti-intersystem crossing rate constant, it can effectively inhibit the spoke as caused by energy gap rule
The reduction of transfer rate is penetrated, to obtain high photoluminescence quantum yield (PLQY).Super plane shows big rigid simultaneously
Property, the stability of " thermal activation delayed fluorescence " (TADF) material is increased, can be improved the service life of device.
In the present embodiment, the molecular structural formula of the electron acceptor A is
The structural formula of the electron donor is
The corresponding molecular formula of the thermal activation delayed fluorescence molecule are as follows:
Its synthetic route is
It is of the invention in the remaining embodiments, the molecular structural formula of the electron acceptor A can also be in following structural formula
At least one:
The molecular structural formula of electron donor D can also be at least one of following structural formula or the derivative of following donor
Object:
By the permutation and combination of electron donor D and electron acceptor A, always there is the thermal activation delayed fluorescence of 108 different structures
Molecular.
In order to preferably explain the present invention, thermal activation delayed fluorescence molecule of the invention is also described in detail in the present embodiment
Preparation method, specific preparation process is as follows:
By 8.13g, the 3 of 10mmol, 9,15- tri- bromo- 5,11,17- trimethyls-trimerization quinolinone, 3.18g, 33mmol's
4- (diphenyl amino)-phenyl boric acid, 30mL toluene and 10mL 2.5M wet chemical is added to the Shrek of 100mL
(schlenk) it in bottle, is carried out substituting gas with argon gas, obtains the first solution.
Then first solution be added 0.48g, the four triphenyl phosphorus palladiums of 0.4mmol, 80 DEG C at a temperature of carry out
Back flow reaction for 24 hours, obtains the second solution.
After second solution is cooled to room temperature, the second solution is extracted three times with DCM (methylene chloride), washing
Three times, and with anhydrous sodium sulfate it dries, filters, is spin-dried for.Column chromatography is carried out with the silica gel of 200-300 mesh, leacheate is petroleum ether
With the mixture of methylene chloride, volume ratio 1:1 obtains the thermal activation delay in dark red solid 12.01g i.e. the present embodiment
Fluorescent molecule material, yield 92%.
Embodiment 2
Electroluminescent hot activation delayed fluorescence device of the invention uses the thermal activation delayed fluorescence molecular material in embodiment 1,
By the high efficiency of the thermal activation delayed fluorescence molecular material, it is weak roll-off, the characteristic of long wavelength preparation electroluminescent hot activation prolong
Slow fluorescent device has the characteristics that the high efficiency, long-life, high-precision.
Specifically, as shown in Fig. 2, the electroluminescent hot activation delayed fluorescence device 1 includes substrate 10, note in the present embodiment
Enter layer 20, hole transmission layer 30, luminescent layer 40, electron transfer layer 50, cathode layer 60.Wherein, the substrate 10 is equipped with conduction
The glassy layer of film 11.
The implanted layer 20 is set on the substrate 10,2,3,6,7,10,11- six cyano of material-Isosorbide-5-Nitrae, and 5,8,9,
Six azepine benzophenanthrene of 12-.
The hole transmission layer 30 is set on the implanted layer 20, material 4, [(the 4- first of N, N- bis- of 4'- cyclohexyl two
Base phenyl) aniline].
The luminescent layer 40 is set on the hole transmission layer 30, and 40 material therefor of luminescent layer is that the thermal activation is prolonged
Slow fluorescent molecule.
The electron transfer layer 50 is set on the luminescent layer 40, material 1,3,5- tri- (3- (3- pyridyl group) phenyl)
Benzene.
The cathode layer 60 is set on the electron transfer layer 50, and material is lithium fluoride and aluminium, wherein lithium fluoride and aluminium
Thickness range be respectively 0.1nm to 500nm.
Wherein, in the present embodiment, the thickness of the lithium fluoride and aluminium is respectively 1nm and 100nm.
Fig. 3 is the performance data table of the electroluminescent hot activation delayed fluorescence device, the electroluminescent hot activation delayed fluorescence device
Current versus brightness-voltage characteristic of part is the source the Keithley measuring system by having corrected silicon photoelectric diode
(Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) is completed, electroluminescent spectrum be by
French JY company SPEX CCD3000 spectrometer measurement, all measurements are completed in atmosphere at room temperature.
The above is merely preferred embodiments of the present invention, be not intended to limit the invention, it is all in spirit of the invention and
Made any modifications, equivalent replacements, and improvements etc., should all be included in the protection scope of the present invention within principle.
Claims (10)
1. a kind of thermal activation delayed fluorescence molecule, which is characterized in that including electron donor and electron acceptor, wherein the electronics
The receptor thiochromene ketone groups of dioxo containing trimerization.
2. thermal activation delayed fluorescence molecule according to claim 1, which is characterized in that the molecular structural formula packet of electron acceptor
Include one of following structural formula:
3. thermal activation delayed fluorescence molecule according to claim 1, which is characterized in that the molecular structure of the electron donor
Formula includes one of following structural formula:
4. thermal activation delayed fluorescence molecule according to claim 1, which is characterized in that
When the structural formula of the electron donor is
The structural formula of electron acceptor is
The corresponding molecular formula of the thermal activation delayed fluorescence molecule are as follows:
5. a kind of preparation method of thermal activation delayed fluorescence molecule, which is characterized in that including providing electron donor and there is trimerization
The electron acceptor chemical combination of dioxo thiochromene ketone groups forms the thermal activation delayed fluorescence molecule.
6. the preparation method of thermal activation delayed fluorescence molecule according to claim 5, which is characterized in that specific steps include
By the bromo- trimerization dioxo thiochromene ketone of 3,9,15- tri-, 4- (diphenyl amino)-phenyl boric acid, toluene and 2.5M potash water
In the Shrek bottle that solution is added to, is carried out substituting gas with argon gas, obtain the first solution.
Four triphenyl phosphorus palladiums are added in first solution, 80 DEG C at a temperature of back flow reaction for 24 hours, it is molten to obtain second
Liquid.
After being cooled to room temperature, second solution is extracted, is washed, is dried, filtered and is spin-dried for methylene chloride to obtain
Four solution；
Column is carried out to the 4th solution with silica gel to chromatograph to obtain target compound.
7. the preparation method of thermal activation delayed fluorescence molecule according to claim 6, which is characterized in that the column chromatography
Leacheate is the mixture of petroleum ether and methylene chloride.
8. a kind of electroluminescent hot activation delayed fluorescence device, which is characterized in that it postpones with thermal activation as described in claim 1
Fluorescent molecule.
9. electroluminescent hot activation delayed fluorescence device according to claim 8, which is characterized in that it further include substrate, the lining
Bottom is the glassy layer equipped with conductive film；
Implanted layer is set on the substrate；
Hole transmission layer is set on the implanted layer；
Luminescent layer is set on the hole transmission layer, and the luminescent layer material therefor is the thermal activation delayed fluorescence molecule；
Electron transfer layer is set on the luminescent layer；
Cathode layer is set on the electron transfer layer.
10. electroluminescent hot activation delayed fluorescence device according to claim 9, which is characterized in that
The material of the implanted layer is six cyano -1,4,5,8,9,12- of 2,3,6,7,10,11-, six azepine benzophenanthrene；
The material of the hole transport is 4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyl) aniline]；
The material of the electron transfer layer is 1,3,5- tri- (3- (3- pyridyl group) phenyl) benzene；
The material of the cathode layer is lithium fluoride and aluminium.
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| CN110015994A (en) * | 2019-04-29 | 2019-07-16 | 武汉华星光电半导体显示技术有限公司 | Thermal activation delayed fluorescence material and preparation method thereof, display device |
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| CN106632404A (en) * | 2016-11-16 | 2017-05-10 | 长春海谱润斯科技有限公司 | Light output material and organic light emitting device (OLED) using same |
| CN107312017A (en) * | 2017-07-13 | 2017-11-03 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device of Han phenoxazines/Sai oxazine analog derivatives |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632404A (en) * | 2016-11-16 | 2017-05-10 | 长春海谱润斯科技有限公司 | Light output material and organic light emitting device (OLED) using same |
| CN107312017A (en) * | 2017-07-13 | 2017-11-03 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device of Han phenoxazines/Sai oxazine analog derivatives |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110015994A (en) * | 2019-04-29 | 2019-07-16 | 武汉华星光电半导体显示技术有限公司 | Thermal activation delayed fluorescence material and preparation method thereof, display device |
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