CN108329252A - A kind of aggregation inducing hot activation delayed fluorescence material and its organic electroluminescence device - Google Patents
A kind of aggregation inducing hot activation delayed fluorescence material and its organic electroluminescence device Download PDFInfo
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Abstract
The invention discloses a kind of aggregation inducing hot activation delayed fluorescence material and its organic electroluminescence device, the compound with one of structure shown in following three kinds, structural formula is：Wherein, R1‑R3In there are two be H, one be electron donating group.Luminescent layer provided by the invention uses novel hot activation delayed fluorescence material, have many advantages, such as that aggregation inducing effect, high fluorescence quantum yield, easy derivatization and stability are good, preparation method is simple, raw material is cheap, products collection efficiency is high, can prepare on a large scale.Organic electroluminescence device provided by the invention has many advantages, such as high efficiency, low driving voltage, long-life and stable luminescence.
Description
Technical field
The invention belongs to field of organic electroluminescent materials, and in particular to a kind of luminescent layer is warm using novel aggregation inducing
Activate delayed fluorescence material and its organic electroluminescence device.
Background technology
Twentieth century comes into information-based society, organic electroluminescent LED (OLED) due to self-luminous,
The advantages such as high brightness, low energy consumption, ultra-thin, wide viewing angle become the hot spot of research, are known as next generation display.In order to realize
The large-area applications that OLED is shown, it is necessary to the better luminescent material of performance, to further increase device light emitting efficiency, reduce
Energy consumption.Phosphor material can obtain higher device efficiency, but materials synthesis cost is higher；Fluorescent material cost is relatively low, and
Fluorescent material with hot activation delayed fluorescence can break through the theoretical efficiency limitation of conventional fluorescent material, acquisition and phosphor material
Quite even surmount the device efficiency of phosphor material, singlet-triplet state energy gap (Δ E of such materialST) very small, IQE
100% can equally be reached, be expected to become next generation's OLED luminescent materials.
The Enhancement of Fluorescence of aggregation inducing is a research field being concerned recent years, aggregation inducing hot activation
Delayed fluorescence material (AIE-TADF) is a kind of novel luminescent material, starts to be widely studied, it has hot activation simultaneously
Delayed fluorescence property and aggregation-induced emission property, synthetic method is simple, is easy to purify, can be used conveniently to prepare pressure sensing
Undoped emitting layer material in device, anti-false trademark or electroluminescent organic material device, therefore develop efficient AIE-TADF
It is of great significance.
Invention content
Technical problem：In view of above-mentioned analysis, the present invention is intended to provide a kind of aggregation inducing hot activation delayed fluorescence material
And its organic electroluminescence device, existing TADF material low, expensive to solve traditional OLED luminescent materials quantum efficiency
That there are synthesis steps is long for material, preparation efficiency is low, is difficult to the problems such as prepare with scale.
Technical solution：The aggregation inducing hot activation delayed fluorescence material of the present invention has to be tied substantially as shown in formula I-III
Structure,
Wherein, R1-R3In two be H, one be electron donating group.
Wherein, the electron donating group be substituted or unsubstituted carbazyl, substituted or unsubstituted aryl amine, substitution or
Unsubstituted indole carbazole base, substituted or unsubstituted phenoxazine group, substituted or unsubstituted phenothiazinyl or substitution or does not take
The acridinyl in generation.
The electron donating group is the group such as lower structure：
4. aggregation inducing hot activation delayed fluorescence material described in is specially the compound of following C1-C12：
The organic electroluminescence device sequence of the aggregation inducing hot activation delayed fluorescence material preparation of the present invention is set as sun
Pole, hole injection layer, the first exciton barrier-layer, luminescent layer, the second exciton barrier-layer, electron transfer layer, electron injecting layer, the moon
Pole, wherein luminescent layer include only the single aggregation inducing hot activation delayed fluorescence material.
Advantageous effect：Luminescent layer provided by the invention is imitated using novel hot activation delayed fluorescence material with aggregation inducing
Answer, high fluorescence quantum yield, good easy derivatization and stability the advantages that, prepare that synthetic method is simple, raw material is cheap, production
Produce rate is high, can prepare on a large scale.Organic electroluminescence device provided by the invention has high efficiency, low driving voltage, longevity
The advantages that life and stable luminescence.The hot activation delayed fluorescence material of the present invention shines in addition to may be used as organic electroluminescence device
Doping object in layer, applies also for light emitting host layer, it is also possible to make the various organic electroluminescences of fluorescent material and phosphor material
Luminescent device.In addition to preparing the undoped luminescent layer material in pressure sensor, anti-false trademark or electroluminescent organic material device
Material, it may also be used for low-power consumption and efficient lighting use etc..
Specific implementation mode
The preferred embodiment of the present invention is detailed below, so that those skilled in the art can be better understood from this hair
It is bright and can be practiced, but illustrated embodiment is not as limitation of the present invention.
The hot activation delayed fluorescence material of the present invention, has the following structure：
Wherein R1-R3In two be H, one be electron donating group.The electron donating group is selected from following group：
The above-mentioned preferred AIE-TADF materials of the present invention:
Compound experiment
Embodiment 1
Synthesize compound C1.
1. under nitrogen protection, 5g is added in 30mL anhydrous methylene chlorides bromo-acid, it is slowly dropped into 7.6g
Dicyclohexylcarbodiimide, 1.25g 4-dimethylaminopyridine, 70mL anhydrous methylene chlorides mixed solution in, react at room temperature
For 24 hours, it filters, hexane recrystallization, column chromatography purification.It is 90% to obtain intermediate product A yields；
2. 0.16g potassium hydroxide, 1.6mL ethanol solutions under nitrogen protection, are added to 1.04g 4,4'- dibromos
In dibenzoyl, 1.04g intermediate product A, 4mL absolute ethyl alcohol mixed solutions, flow back 40min, is cooled to room temperature, and filters, and use is anhydrous
Ethyl alcohol rinses, and it is 92% to obtain intermediate product B yields；
3. 1g intermediate product B, 0.15g acetonitrile, 40mL anhydrous methylene chloride mixed solutions are cooled to 5 DEG C hereinafter, slowly
0.79mL TiCl are added4, 3.7mL pyridines, stir 3h at room temperature, extract, anhydrous sodium sulfate drying, column chromatography purification, obtain intermediate
Product C yields are 91%；
4. under nitrogen protection, 0.1g intermediate products C is added in 5mL DMF, 160 DEG C are heated to, reacts 1h, is used
Rotary Evaporators hang dry solvent, and it is 94% to obtain intermediate product D yields；
5. 0.013g cuprous iodides, 0.014g 1.10- coffee Luo Lin under nitrogen protection, are added to 0.7g carbazoles, 0.5g
Intermediate product D, 0.4g potassium carbonate, 30mL DMF mixed solution in, react 12h at a temperature of 140-160 DEG C；It is cooled to
After room temperature, it is added distilled water into reaction, then with dichloromethane aqueous layer extracted；Organic layer is dried with anhydrous sodium sulfate, column chromatography
Separating-purifying, it is 92% to obtain product C1 yields.
Mass spectrum：1067.
Elemental analysis：C:88.85 H:4.59 N:6.56
Embodiment 2
Synthesize C2.The reactant carbazole that 1 final step of embodiment is reacted is substituted for tert-butyl carbazole, process and embodiment
1 identical synthetic method obtains C2, yield 91%.
Mass spectrum：1516
Elemental analysis：C:87.88 H:7.51 N:4.62
Embodiment 3
Synthesize C3.By 1 final step of embodiment react reactant carbazole be substituted for phenoxazine, by with 1 phase of embodiment
Same synthetic method, obtains C3, yield 90%.
Mass spectrum：1131
Elemental analysis：C:83.80 H:4.36 N:6.19
Embodiment 4
Synthesize C4.By 1 final step of embodiment react reactant carbazole be substituted for phenthazine, by with 1 phase of embodiment
Same synthetic method, obtains C4, yield 91%.
Mass spectrum：1220
Elemental analysis：C:79.30 H:4.13 N:5.85
Embodiment 5
Synthesize C5.The reactant acetonitrile that the 3rd step of embodiment 1 is reacted is substituted for malononitrile, by same as Example 1
Synthetic method obtains C5, yield 92%.
Mass spectrum：1092.
Elemental analysis：C:87.91 H:4.40 N:7.69
Embodiment 6
Synthesize C6.The reactant acetonitrile that the 3rd step of embodiment 1 is reacted is substituted for malononitrile, the reaction of final step reaction
Object carbazole is substituted for tert-butyl carbazole, by synthetic method same as Example 1, obtains C6, yield 93%.
Mass spectrum：1540
Elemental analysis：C:87.27 H:7.27 N:5.45
Embodiment 7
Synthesize C7.The reactant acetonitrile that the 3rd step of embodiment 1 is reacted is substituted for malononitrile, the reaction of final step reaction
Object carbazole is substituted for phenoxazine, by synthetic method same as Example 1, obtains C7, yield 92%.
Mass spectrum：1156
Elemental analysis：C:83.04 H:4.15 N:7.27
Embodiment 8
Synthesize C8.The reactant acetonitrile that the 3rd step of embodiment 1 is reacted is substituted for malononitrile, the reaction of final step reaction
Object carbazole is substituted for phenthazine, by synthetic method same as Example 1, obtains C8, yield 91%.
Mass spectrum：1220
Elemental analysis：C:78.69 H:3.93 N:6.88
Embodiment 9
Synthesize C9.The reactant acetonitrile that 3rd step in embodiment 1 is reacted is substituted for bromobenzylcyanide, by with embodiment 1
Identical synthetic method obtains C9, yield 93%.
Mass spectrum：1308
Elemental analysis：C:89.00 H:4.58 N:6.42
Embodiment 10
Synthesize C10.The reactant acetonitrile that 3rd step in embodiment 1 is reacted is substituted for bromobenzylcyanide, final step reaction
Reactant carbazole be substituted for tert-butyl carbazole, by synthetic method same as Example 1, obtain C10, yield 92%.
Mass spectrum：1868
Elemental analysis：C:88.00 H:7.49 N:4.50
Embodiment 11
Synthesize C11.The reactant acetonitrile that 3rd step in embodiment 1 is reacted is substituted for bromobenzylcyanide, final step reaction
Reactant carbazole be substituted for phenoxazine, by synthetic method same as Example 1, obtain C11, yield 91%.
Mass spectrum：1388
Elemental analysis：C:83.86 H:4.32 N:6.05
Embodiment 12
Synthesize C12.The reactant acetonitrile that 3rd step in embodiment 1 is reacted is substituted for bromobenzylcyanide, final step reaction
Reactant carbazole be substituted for phenthazine, by synthetic method same as Example 1, obtain C12, yield 90%.
Mass spectrum：1468
Elemental analysis：C:79.29 H:4,.09 N:5.72
The representative instance of organic electroluminescence device structure of the present invention includes but not limited to following several structures：
(1) anode/luminescent layer/cathode；
(2) anode/hole transmission layer/luminescent layer/electron transfer layer/cathode；
(3) anode/hole injection layer/hole transmission layer/electronic barrier layer/luminescent layer/electron transfer layer/electron injection
Layer/cathode；
(4) anode/hole injection layer/hole transmission layer/electronic barrier layer/luminescent layer/hole blocking layer/electron-transport
Layer/electron injecting layer/cathode；
In following embodiments of the present invention, OLED includes anode/hole injection layer/first exciton blocking being sequentially overlapped
Layer/luminescent layer/the second exciton barrier-layer/electron transfer layer/electron injecting layer/cathode.Its Anodic is ITO；Hole injection layer
For NPB；First exciton barrier-layer has TCTA and mCP layers of composition；Luminescent layer includes only the hot activation delayed fluorescence material of the present invention
(C1-C12)；Second exciton barrier-layer is DPEPO；Electron transfer layer is Bphen；Electron injecting layer is LiF；Cathode is Al.
Above-mentioned material is as follows as the OLED performance datas of luminescent layer：
As can be seen from the above table, the organic electroluminescence device luminescent layer based on the present invention uses novel AIE-TADF materials
Material can achieve over the limitation of 5% external quantum efficiency of conventional fluorescent, realize higher efficiency.Embodiment described above be only for
The preferred embodiment for absolutely proving the present invention and being lifted, protection scope of the present invention are without being limited thereto.The technology of the art
Personnel on the basis of the present invention made by equivalent substitute or transformation, within protection scope of the present invention.The protection of the present invention
Range is subject to claims.
Claims (5)
1. a kind of aggregation inducing hot activation delayed fluorescence material, which is characterized in that the material has basic as shown in formula I-III
Structure,
Wherein, R1-R3In two be H, one be electron donating group.
2. aggregation inducing hot activation delayed fluorescence material according to claim 1, which is characterized in that the electron donating group
For substituted or unsubstituted carbazyl, substituted or unsubstituted aryl amine, substituted or unsubstituted indole carbazole base, substitution or not
Substituted phenoxazine groups, substituted or unsubstituted phenothiazinyl or substituted or unsubstituted acridinyl.
3. aggregation inducing hot activation delayed fluorescence material according to claim 2, which is characterized in that the electron donating group
For the group of such as lower structure：
4. aggregation inducing hot activation delayed fluorescence material according to claim 1, which is characterized in that the aggregation inducing
Hot activation delayed fluorescence material is specially the compound of following C1-C12：
5. a kind of organic electroluminescence of aggregation inducing hot activation delayed fluorescence material preparation as described in claim 1 or 4
Part, it is characterised in that the organic electroluminescence device sequence is set as anode, hole injection layer, the first exciton barrier-layer, hair
Photosphere, the second exciton barrier-layer, electron transfer layer, electron injecting layer, cathode, wherein luminescent layer are only lured comprising the single aggregation
Heat conduction activates delayed fluorescence material.
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Cited By (7)
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| CN109244256A (en) * | 2018-08-01 | 2019-01-18 | 华南理工大学 | Efficient undoped ultra-thin light-emitting layer thermal activation delayed fluorescence Organic Light Emitting Diode and preparation method thereof |
| CN110642842A (en) * | 2019-09-30 | 2020-01-03 | 上海天马有机发光显示技术有限公司 | Compound, display panel and display device |
| CN111606841A (en) * | 2020-05-29 | 2020-09-01 | 盐城工学院 | Deep blue photo-thermal crosslinking type thermal activation delayed fluorescence material and preparation method and application thereof |
| CN112151688A (en) * | 2020-09-27 | 2020-12-29 | 京东方科技集团股份有限公司 | Light-emitting device, display substrate and display device |
| CN112480403A (en) * | 2020-11-27 | 2021-03-12 | 江苏海洋大学 | Packaging type delayed fluorescence polymer material |
| CN112679414A (en) * | 2020-10-30 | 2021-04-20 | 苏州大学 | Super-thick non-doped electroluminescent device based on thermal activation delayed fluorescent material and preparation method thereof |
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| CN109244256B (en) * | 2018-08-01 | 2020-05-22 | 华南理工大学 | High-efficiency undoped ultrathin luminous layer thermal activation delayed fluorescence organic light-emitting diode and preparation method thereof |
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| US11758809B2 (en) | 2019-09-30 | 2023-09-12 | Shanghai Tianma AM-OLED Co., Ltd. | Compound, display panel, and display apparatus |
| CN111606841A (en) * | 2020-05-29 | 2020-09-01 | 盐城工学院 | Deep blue photo-thermal crosslinking type thermal activation delayed fluorescence material and preparation method and application thereof |
| CN111606841B (en) * | 2020-05-29 | 2022-07-19 | 山西穿越光电科技有限责任公司 | Deep blue photo-thermal crosslinking type thermal activation delayed fluorescence material and preparation method and application thereof |
| CN112151688A (en) * | 2020-09-27 | 2020-12-29 | 京东方科技集团股份有限公司 | Light-emitting device, display substrate and display device |
| CN112679414A (en) * | 2020-10-30 | 2021-04-20 | 苏州大学 | Super-thick non-doped electroluminescent device based on thermal activation delayed fluorescent material and preparation method thereof |
| CN112480403A (en) * | 2020-11-27 | 2021-03-12 | 江苏海洋大学 | Packaging type delayed fluorescence polymer material |
| CN113527279A (en) * | 2021-07-13 | 2021-10-22 | 京东方科技集团股份有限公司 | Light-emitting film, preparation method thereof, light-emitting device and display device |
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Application publication date: 20180727 |