CN110437229A - Thermal activation delayed fluorescence molecular material and its synthetic method, electroluminescent device - Google Patents
Thermal activation delayed fluorescence molecular material and its synthetic method, electroluminescent device Download PDFInfo
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Abstract
The present invention provides a kind of thermal activation delayed fluorescence molecular material and its synthetic method, organic electroluminescence device, synthesize a series of nitrogenous-carbonyl class thermal activation delayed fluorescence molecules, and nitrogenous-carbonyl class thermal activation delayed fluorescence molecule is since with intramolecular multiple resonance effect, can narrow luminescent spectrum well.And nitrogenous-carbonyl class thermal activation delayed fluorescence molecule has super plane, it can show big rigidity, so that molecule has high intersystem crossing rate constant and anti-intersystem crossing rate constant, the reduction that the radiation transistion rate as caused by energy gap rule can effectively be inhibited, to obtain high PLQY；The stability for increasing TADF material simultaneously, can be improved the service life of device.
Description
Technical field
The present invention relates to field of display technology, specially a kind of thermal activation delayed fluorescence molecular material and its synthetic method,
Electroluminescent 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 differences (Δ EST), such triplet
Exciton can return to singlet state by anti-intersystem crossing (RISC), then be shone by radiation transistion to ground state, so as to same
Shi Liyong is mono-, 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, to obtain efficient, the long-life that meet the requirements
Luminous organic material.
For TADF material, small Δ EST and high photoluminescence quantum yield (PLQY) are to prepare high efficiency OLED
Necessary condition.But currently, the luminous spectrum half-peak breadth (FWHM) of TADF material is wider, it is unfavorable for top emitting device efficiency
It improves.
Summary of the invention
To solve above-mentioned technical problem: the present invention provide a kind of thermal activation delayed fluorescence molecular material and its synthetic method,
Organic electroluminescence device, a series of nitrogenous-carbonyl class thermal activation delayed fluorescence molecules of synthesis, and nitrogenous-carbonyl class thermal activation
Delayed fluorescence molecule is since with intramolecular multiple resonance effect, can narrow luminescent spectrum well.And nitrogenous-carbonyl class
Thermal activation delayed fluorescence molecule has super plane, can show big rigidity, so that molecule has high intersystem crossing speed
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 PLQY；The stability for increasing TADF material simultaneously, can be improved the service life of device.
The technical solution to solve the above problems is: providing a kind of thermal activation delayed fluorescence molecular material, has the following structure
General formula:
Wherein, X includes carbon, oxygen, sulphur；R group includes aryl, alkylaryl and nitrogenous aryl.
Further, the molecular structural formula of the thermal activation delayed fluorescence molecular material includes following one kind:
The present invention also provides a kind of synthetic methods of thermal activation delayed fluorescence molecular material, comprising the following steps: by 2- (9,
9- dimethyl acridinium base) isophathalic acid, oxalyl chloride, solvent and the first catalyst be placed in reaction vessel, be subsequently added into using argon
Gas carries out the reaction vessel to substitute gas progress back flow reaction 0.5h the first mixed solution of formation；The second catalyst is added to institute
It states and carries out back flow reaction 3h in reaction vessel with first mixed solution, cooling obtains the second mixed solution；By described second
Mixed solution is added into sodium hydrate aqueous solution quenching reaction and forms third mixed solution；Using methylene chloride to the third
Mixed solution carries out 3 extractions, 3 washings, and is dried, filters and is concentrated to get target chemical combination by anhydrous sodium sulfate
Object；Column chromatography is carried out to the solution title compound by using the silica gel of 200-300 mesh, and is eluted with leacheate, finally
It isolates and purifies to obtain the thermal activation delayed fluorescence molecular material.
Further, first catalyst includes n,N-Dimethylformamide；Second catalyst includes four chlorinations
Tin；The solvent includes methylene chloride；The leacheate is petroleum ether.
Further, the molar ratio of 2- (9, the 9- dimethyl acridinium base) isophathalic acid and the oxalyl chloride is 10:22.
The present invention also provides a kind of electroluminescent devices, including the thermal activation delayed fluorescence molecular material.
Further, the electroluminescent device includes: first electrode；Hole injection layer is set in the first electrode；
Hole transmission layer is set on the electron injecting layer；Luminescent layer is set on the hole transmission layer, material used in the luminescent layer
Material includes the thermal activation delayed fluorescence molecular material；Electron transfer layer is set on luminescent layer；Second electrode is set to the electricity
In sub- transport layer.
It further, further include 4,4'- bis- (9- carbazole) biphenyl in the luminescent layer.
Further, the first electrode is anode, and material therefor is tin indium oxide；The second electrode is cathode,
Its material therefor is one of lithium fluoride or aluminium.
Further, the hole injection layer material therefor be 2,3,6,7,10,11- six cyano-Isosorbide-5-Nitrae, 5,8,9,12- six
Azepine benzophenanthrene；Described electron transfer layer material therefor 3,3'- [5'- [3- (3- pyridyl group) phenyl] [1,1':3', 1 "-three connection
Benzene] -3,3 "-diyl] two pyridines；The hole transmission layer material therefor is-two [(the 4- methylbenzene of N, N- bis- of 4,4 '-cyclohexyl
Base) aniline].
The beneficial effects of the present invention are: the present invention provide a kind of thermal activation delayed fluorescence molecular material and its synthetic method,
Organic electroluminescence device, a series of nitrogenous-carbonyl class thermal activation delayed fluorescence molecules of synthesis, and nitrogenous-carbonyl class thermal activation
Delayed fluorescence molecule is since with intramolecular multiple resonance effect, can narrow luminescent spectrum well.And nitrogenous-carbonyl class
Thermal activation delayed fluorescence molecule has super plane, can show big rigidity, so that molecule has high intersystem crossing speed
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 PLQY；The stability for increasing TADF material simultaneously, can be improved the service life of device.
Detailed description of the invention
The present invention is further explained with reference to the accompanying drawings and examples.
Fig. 1 be through the embodiment of the present invention in preparation method made from thermal activation delayed fluorescence molecular material fluorescence light
Spectrogram.
Fig. 2 is EL device structure figure in the embodiment of the present invention.
Appended drawing reference:
10 electroluminescent devices；
1 first electrode；2 hole injection layers；
3 hole transmission layers；4 luminescent layers；
5 electron transfer layers；6 second electrodes.
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.
The present invention provides a kind of thermal activation delayed fluorescence molecular material, has the following structure general formula:
Wherein, X includes carbon, oxygen, sulphur；R group includes aryl, alkylaryl and nitrogenous aryl.
Further, the molecular structural formula of the thermal activation delayed fluorescence molecular material includes following one kind:
In order to more clearly explain the present invention, below with reference to the synthesis of thermal activation delayed fluorescence molecular material of the invention
The thermal activation delayed fluorescence molecular material is further expalined in method.
In an embodiment of the present invention, to prepare a kind of (the thermal activation delayed fluorescence molecule of the invention of target compound one
Material) for, the preparation method for the thermal activation delayed fluorescence molecular material that the present invention will be described in detail.Wherein target compound one
General structure is as follows:
Thermal activation delayed fluorescence molecular material preparation method of the invention the following steps are included:
S1 2- (9,9-dimethylacridan base) isophathalic acid, oxalyl chloride, solvent and the first catalyst) are placed in reaction vessel
In, it is subsequently added into and the reaction vessel is carried out using argon gas to substitute gas progress back flow reaction 0.5h the first mixed solution of formation；
First catalyst includes n,N-Dimethylformamide, and the solvent includes methylene chloride.
The molar ratio of 2- (9,9-dimethylacridan base) isophathalic acid and the oxalyl chloride is 10:22.
S2 the second catalyst) is added and carries out back flow reaction 3h with first mixed solution into the reaction vessel, it is cold
But the second mixed solution is obtained；Second catalyst includes tin tetrachloride
S3 quenching reaction) is added into sodium hydrate aqueous solution in second mixed solution and forms third mixed solution；
S4 3 extractions, 3 washings) are carried out to the third mixed solution using methylene chloride, and pass through anhydrous sodium sulfate
It is dried, filters and is concentrated to get target compound；
S5 column chromatography) is carried out to the solution title compound by using the silica gel of 200-300 mesh, and is drenched with leacheate
It washes, is finally separating purifying and obtains the thermal activation delayed fluorescence molecular material.The leacheate is petroleum ether.
By the preparation method of the present embodiment, specific chemical equation is as follows:
2.76g greenish yellow solid, yield 82% are finally obtained by the chemical equation.
Preparation method through this embodiment prepares thermal activation delayed fluorescence molecular material, can be effectively synthesized thermal activation and prolong
Slow fluorescent molecule material, while can be improved combined coefficient.
In order to verify whether the characteristic of thermal activation delayed fluorescence molecular material of the invention meets wanting for electroluminescent device
The thermal activation delayed fluorescence molecular material asked, therefore obtain preparation method through this embodiment in the present embodiment carries out spectrum
Experiment and optical physics Data Detection.Obtain fluorescence spectra and optical physics data as shown in Table 1 as shown in Figure 1.
Table 1 is the optical physics data of thermal activation delayed fluorescence molecular material of the invention.
| PL Peak(nm) | S1(eV) | T1(eV) | ΔEST(eV) | PLQY (%) | |
| Target compound one | 570 | 2.41 | 2.34 | 0.07 | 95 |
Fig. 1 it is found that the effective wavelength range of target compound one of the invention between 500-700nm, therefore, Ke Yi
The luminescent spectrum of molecule is adjusted within the scope of this.As shown in Table 1, thermal activation delayed fluorescence molecular material of the invention has lesser
Minimum singlet state and triple energy level differences (Δ EST)。
As shown in Fig. 2, the present invention also provides a kind of electroluminescent device 10, including the thermal activation delayed fluorescence point
Sub- material.The electronic light emitting devices 10 are yellow light-feux rouges electronic light emitting devices.
Specifically, the electroluminescent device includes first electrode 1, hole injection layer 2, hole transmission layer 3, luminescent layer
4, electron transfer layer 5, second electrode 6.Wherein, the hole injection layer 2 is set in the first electrode 1；The hole transport
Layer 3 is set on the electron injecting layer 2；The luminescent layer 4 is set on the hole transmission layer 3,4 material therefor of luminescent layer
Including the thermal activation delayed fluorescence molecular material and 4,4'- bis- (9- carbazole) biphenyl, based on 4,4'- bis- (9- carbazole) biphenyl
Body molecule, wherein adulterating the thermal activation delayed fluorescence molecular material；The electron transfer layer 5 is set on the luminescent layer 4；Institute
Second electrode 6 is stated on the electron transfer layer 5.
In the present embodiment, the first electrode 1 is anode, and material therefor is tin indium oxide；The second electrode 6 is yin
Pole, material therefor are one of lithium fluoride or aluminium.5 material therefor of electron transfer layer is 3,3'- [5'- [3- (3- pyrrole
Piperidinyl) phenyl] [1,1':3', 1 "-terphenyl] -3,3 "-diyl] two pyridines；3 material therefor of hole transmission layer is 4,4 '-
Cyclohexyl-two [N, N- bis- (4- aminomethyl phenyl) aniline], 2 material therefor of hole injection layer are 2,3,6,7,10,11- six cyanogen
Six azepine benzophenanthrene of base -1,4,5,8,9,12-.
Table 2 is the performance data table using the electroluminescent device 10 of target compound.
| Device | Maximum brightness (cd/m2) | FWHM(nm) | EL peak(nm) | Maximum external quantum efficiency (%) |
| Target compound one | 33395 | 27 | 574 | 24 |
As shown in Table 2, electroluminescent device 10 of the invention, in luminescent layer 4 using the thermal activation delayed fluorescence point
Sub- material effectively produces electroluminescent device, and improves the luminous efficiency of electroluminescent device.
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 molecular material, which is characterized in that have the following structure general formula:
Wherein, X includes carbon, oxygen, sulphur；R group includes aryl, alkylaryl and nitrogenous aryl.
2. thermal activation delayed fluorescence molecular material according to claim 1, which is characterized in that the thermal activation delayed fluorescence
The molecular structural formula of molecular material includes following one kind:
3. a kind of synthetic method of thermal activation delayed fluorescence molecular material, which comprises the following steps: by 2- (9,9-
Dimethyl acridinium base) isophathalic acid, oxalyl chloride, solvent and the first catalyst be placed in reaction vessel, be subsequently added into using argon gas
The reaction vessel is carried out to substitute gas progress back flow reaction 0.5h the first mixed solution of formation；
The second catalyst is added and carries out back flow reaction 3h with first mixed solution into the reaction vessel, it is cooling to obtain the
Two mixed solutions；
Quenching reaction is added into sodium hydrate aqueous solution in second mixed solution and forms third mixed solution；Use dichloro
Methane carries out 3 extractions, 3 washings to the third mixed solution, and is dried by anhydrous sodium sulfate, is filtered and dense
Contracting obtains target compound；
Column chromatography is carried out to the solution title compound by using the silica gel of 200-300 mesh, and is eluted with leacheate, finally
It isolates and purifies to obtain the thermal activation delayed fluorescence molecular material.
4. the synthetic method of thermal activation delayed fluorescence molecular material according to claim 4, which is characterized in that
First catalyst includes n,N-Dimethylformamide；
Second catalyst includes tin tetrachloride；
The solvent includes methylene chloride；
The leacheate is petroleum ether.
5. the synthetic method of thermal activation delayed fluorescence molecular material according to claim 5, which is characterized in that the 2-
The molar ratio of (9,9-dimethylacridan base) isophathalic acid and the oxalyl chloride is 10:22.
6. a kind of electroluminescent device, which is characterized in that including for the described in any item thermal activation delayed fluorescences of claim 1-2
Molecular material.
7. electroluminescent device according to claim 6, which is characterized in that including
First electrode；
Hole injection layer is set in the first electrode；
Hole transmission layer is set on the electron injecting layer；
Luminescent layer is set on the hole transmission layer, and the luminescent layer material therefor includes the thermal activation delayed fluorescence molecule
Material；
Electron transfer layer is set on luminescent layer；
Second electrode is set on the electron transfer layer.
8. electroluminescent device according to claim 7, which is characterized in that
It further include 4,4'- bis- (9- carbazole) biphenyl in the luminescent layer.
9. electroluminescent device according to claim 7, which is characterized in that
The first electrode is anode, and material therefor is tin indium oxide；The second electrode is cathode, and material therefor is fluorine
Change one of lithium or aluminium.
10. electroluminescent device according to claim 7, which is characterized in that
The hole injection layer material therefor is six cyano -1,4,5,8,9,12- of 2,3,6,7,10,11-, six azepine benzophenanthrene；Institute
State electron transfer layer material therefor 3,3'- [5'- [3- (3- pyridyl group) phenyl] [1,1':3', 1 "-terphenyl] -3,3 "-diyl]
Two pyridines；
The hole transmission layer material therefor is 4,4 '-cyclohexyl-two [N, N- bis- (4- aminomethyl phenyl) aniline].
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110845517A (en) * | 2019-11-27 | 2020-02-28 | 常州大学 | Thermal activation delayed fluorescence luminescent material containing nitrogen hetero-spiroalkene parent nucleus and application thereof in electroluminescent device |
| CN111018726A (en) * | 2019-12-05 | 2020-04-17 | 武汉华星光电半导体显示技术有限公司 | Thermal activation delayed fluorescence molecule, preparation method thereof and electrothermal activation delayed fluorescence device |
| CN111606906A (en) * | 2020-06-19 | 2020-09-01 | 苏州久显新材料有限公司 | Polycyclic nitrogen-containing compound and electronic device |
| CN111675709A (en) * | 2020-03-31 | 2020-09-18 | 武汉华星光电半导体显示技术有限公司 | Fluorescent material and synthetic method thereof |
| CN114539287A (en) * | 2020-11-25 | 2022-05-27 | 清华大学 | Polycyclic aromatic compound and application thereof in electroluminescent device |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090295275A1 (en) * | 2005-09-12 | 2009-12-03 | Merck Patent Gmbh | Compounds for organic electronic devices |
| WO2018159662A1 (en) * | 2017-02-28 | 2018-09-07 | 国立大学法人九州大学 | Compound, light emitting material and organic light emitting element |
| CN109456326A (en) * | 2018-12-10 | 2019-03-12 | 苏州大学 | Organic electroluminescence device, the triarylamine derivative of carbonyl bridging and its application |
-
2019
- 2019-07-25 CN CN201910675737.6A patent/CN110437229A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090295275A1 (en) * | 2005-09-12 | 2009-12-03 | Merck Patent Gmbh | Compounds for organic electronic devices |
| WO2018159662A1 (en) * | 2017-02-28 | 2018-09-07 | 国立大学法人九州大学 | Compound, light emitting material and organic light emitting element |
| CN109456326A (en) * | 2018-12-10 | 2019-03-12 | 苏州大学 | Organic electroluminescence device, the triarylamine derivative of carbonyl bridging and its application |
Non-Patent Citations (1)
| Title |
|---|
| F. M. STOYANOVICH 等: "Reactions of arylsulfonyl compounds with excess organolithium reagent 12. 3-lithioarynes as a basis for the synthesis of condensed heterocyclic systems with a central nitrogen atom", 《RUSSIAN CHEMICAL BULLETIN》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110845517A (en) * | 2019-11-27 | 2020-02-28 | 常州大学 | Thermal activation delayed fluorescence luminescent material containing nitrogen hetero-spiroalkene parent nucleus and application thereof in electroluminescent device |
| CN110845517B (en) * | 2019-11-27 | 2021-05-04 | 常州大学 | Thermal activation delayed fluorescence luminescent material containing nitrogen hetero-spiroalkene parent nucleus and application thereof in electroluminescent device |
| CN111018726A (en) * | 2019-12-05 | 2020-04-17 | 武汉华星光电半导体显示技术有限公司 | Thermal activation delayed fluorescence molecule, preparation method thereof and electrothermal activation delayed fluorescence device |
| CN111675709A (en) * | 2020-03-31 | 2020-09-18 | 武汉华星光电半导体显示技术有限公司 | Fluorescent material and synthetic method thereof |
| CN111606906A (en) * | 2020-06-19 | 2020-09-01 | 苏州久显新材料有限公司 | Polycyclic nitrogen-containing compound and electronic device |
| CN114539287A (en) * | 2020-11-25 | 2022-05-27 | 清华大学 | Polycyclic aromatic compound and application thereof in electroluminescent device |
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