CN110003194A - Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus - Google Patents
Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus Download PDFInfo
- Publication number
- CN110003194A CN110003194A CN201910305986.6A CN201910305986A CN110003194A CN 110003194 A CN110003194 A CN 110003194A CN 201910305986 A CN201910305986 A CN 201910305986A CN 110003194 A CN110003194 A CN 110003194A
- Authority
- CN
- China
- Prior art keywords
- layer
- thermal activation
- delayed fluorescence
- compound
- activation delayed
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- 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
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to a kind of thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus, the general structure of the thermal activation delayed fluorescence material is as shown in following formula one: formula oneR indicates that the chemical group as electron donor, R are in the 1st, the 3rd, the 4th or the 5th in pyridine groups, and X isOne of.Thermal activation delayed fluorescence material of the invention has ultrafast reversed intersystem crossing rate and high-luminous-efficiency, for the blue green light TADF material with significant TADF characteristic, when it is applied to organic electroluminescent diode apparatus as emitting layer material, the luminous efficiency that can effectively improve organic electroluminescent diode apparatus, the organic electroluminescent diode apparatus based on thermal activation delayed fluorescence material of the invention have very high device efficiency.
Description
Technical field
The invention belongs to electroluminescent material technical field, in particular to a kind of thermal activation delayed fluorescence material and its preparation
Method and organic electroluminescent diode apparatus.
Background technique
Organic electroluminescent LED (Organic Light-Emitting Diode, OLED) display panel is with its active
It shines and does not need that backlight, luminous efficiency are high, visible angle is big, fast response time, Acclimation temperature range are big, production and processing technology
Relatively easy, the advantages that driving voltage is low, energy consumption is small, lighter and thinner, Flexible Displays and huge application prospect, have attracted crowd
The concern of more researchers.
The principle of OLED device is, under electric field action, hole and electronics are injected from anode and cathode respectively, leads to respectively
Hole injection layer, hole transmission layer and electron injecting layer, electron transfer layer are crossed, is compounded to form exciton, exciton radiation in luminescent layer
Decaying shines.
Core component of the electroluminescent organic material as OLED device has the service performance of device very big
It influences.The luminescent layer of OLED device typically contains material of main part and guest materials, wherein the light emitting guest material to play a leading role
It is most important.The light emitting guest material that the OLED device of early stage uses be fluorescent material, due to its in OLED device singlet state
Exciton ratio with triplet is 1:3, therefore the theoretical internal quantum efficiency (IQE) of the OLED device based on fluorescent material can only reach
To 25%, the application of fluorescence electroluminescent device is significantly limited.Heavy metal complex phosphor material due to heavy atom from
Orbit coupling effect is revolved, allows it to realize 100% IQE using singlet state and triplet exciton simultaneously.However, usually
The heavy metal used is all the precious metals such as iridium (Ir), platinum (Pt), and heavy metal complex phosphorescent light-emitting materials are in blue light material
Material aspect still needs to be broken through.Pure organic thermal activation delayed fluorescence (TADF) material has electron donor (D) and electron acceptor (A)
The molecular structure combined, by cleverly MOLECULE DESIGN, so that molecule has the lesser minimum triple energy level differences of list (Δ EST),
Triplet exciton can return to singlet state by reversed intersystem crossing (RISC) in this way, then be sent out by radiation transistion to ground state
Light, so as to which using single, triplet exciton, 100% IQE also may be implemented simultaneously.
For TADF material, quick reversed intersystem crossing constant (kRISC) and high photoluminescence quantum yield
It (PLQY) is the necessary condition for preparing high efficiency OLED device.Currently, having the TADF material of above-mentioned condition relative to heavy metal
It is still deficienter for Ir complex.
Summary of the invention
The purpose of the present invention is to provide a kind of thermal activation delayed fluorescence material, have ultrafast reversed intersystem crossing rate and
High-luminous-efficiency can be used as organic electroluminescent LED for the TADF compound of the blue green light with significant TADF characteristic
Emitting layer material.
Another object of the present invention is to provide a kind of preparation method of thermal activation delayed fluorescence material, and this method is easy to grasp
Make, and the yield for obtaining target product is higher.
Yet another object of that present invention is to a kind of organic electroluminescent diode apparatus is provided, postponed using above-mentioned thermal activation glimmering
Luminescent material is as emitting layer material, to improve the luminous efficiency of device.
For achieving the above object, the present invention provides a kind of thermal activation delayed fluorescence material, has as shown in following formula one
Chemical structure:
Formula one
R indicates that the chemical group as electron donor, R are in the 1st in pyridine groups
Position, the 3rd, the 4th or the 5th, X isOne of.
Any one of the chemical group R of the electron donor in following group:
The thermal activation delayed fluorescence material is compound 1, compound 2 or compound 3, the compound 1, compound
2 and compound 3 structural formula difference it is as follows:
The present invention also provides a kind of preparation method of thermal activation delayed fluorescence material, its chemical synthesis route is as follows:
Specifically: into reaction flask be added molar ratio be 1:2-4:0.05-0.2:0.2-0.4 halogenated raw material, contain electronics
Then donor compound, palladium acetate and tri-tert-butylphosphine tetrafluoroborate are 2- by with halogenated raw material under anhydrous and oxygen-free environment
Sodium tert-butoxide is added in the molar ratio of 4:1, and the toluene of water removal deoxygenation is squeezed under argon atmosphere, small in 110-120 DEG C of reaction 20-30
When；It is cooled to room temperature, reaction solution is poured into ice water, organic phase is merged after extraction, revolve into silica gel, column chromatographic isolation and purification obtains
Product, calculated yield；
The general structure of the halogenated raw material isWherein, Br is in the 1st in pyridine groups
Position, the 3rd, the 4th or the 5th；
The general structure containing electronic donor compound is R-H, wherein R indicates the chemical group as electron donor.
Any one of the chemical group R of the electron donor in following group:
The electronic donor compound that contains is phenoxazine；
The halogenated raw material is raw material 1, raw material 2 or raw material 3, and the structural formula of the raw material 1, raw material 2 and raw material 3 is respectively
The present invention also provides a kind of organic electroluminescent diode apparatus, including substrate, be set on the substrate
One electrode, the organic function layer being set in first electrode and the second electrode being set on the organic function layer；
The organic function layer includes one or more layers organic film, and at least one layer of organic film is luminescent layer；
The luminescent layer includes thermal activation delayed fluorescence compound as described above.
The luminescent layer is formed using the method that vacuum evaporation or solution coat.
The mixture of material and guest materials based on the material of the luminescent layer, the guest materials are selected from as described above
One of thermal activation delayed fluorescence compound or a variety of.
The substrate is glass substrate, and the material of the first electrode is tin indium oxide, and the second electrode is lithium fluoride
The two-layer composite that layer is constituted with aluminium layer；
The organic function layer includes multilayer organic film, which includes hole injection layer, hole transport
Layer, luminescent layer, electron transfer layer, wherein the material of the hole injection layer is molybdenum trioxide, the material of the hole transmission layer
For TCTA, the material of the electron transfer layer is TmPyPB, and the material of main part is mCBP.
Compared to existing material and technology, the invention has the advantages that and the utility model has the advantages that
(1) structure and position of the invention by electronic donor group is finely adjusted, and is designed special with significant TADF
The thermal activation delayed fluorescence material of property, realize material emission spectrum from blue green light to green range in fine tuning；
(2) thermal activation delayed fluorescence material of the invention is altered between inverse system poor, ultrafast with lower single triplet
The more TADF compound of rate and high-luminous-efficiency can be with when it is applied to organic light-emitting display device as luminescent material
Improve the luminous efficiency of organic light-emitting display device, the organic electroluminescent two based on thermal activation delayed fluorescence material of the invention
Pole pipe device all achieves very high device efficiency.
Detailed description of the invention
With reference to the accompanying drawing, by the way that detailed description of specific embodiments of the present invention, technical solution of the present invention will be made
And other beneficial effects are apparent.
In attached drawing,
The HOMO and lumo energy distribution map that Fig. 1 is compound 1-3 prepared in specific embodiment of the invention 1-3；
Fig. 2 is the photic hair in compound 1-3 prepared in specific embodiment of the invention 1-3 at room temperature toluene solution
Light spectrogram；
Fig. 3 is the structural schematic diagram of organic electroluminescent diode apparatus of the present invention.
Specific embodiment
The some raw materials being not specified used in the present invention are commercial goods.The preparation method of some compounds will be in reality
It applies in case and describes.The present invention is more specifically described in detail combined with specific embodiments below, but embodiment party of the invention
Formula is without being limited thereto.
Embodiment 1:
The synthetic route of target compound 1 is as follows:
Raw material 1 (2.09g, 5mmol) is added into bis- mouthfuls of bottles of 100mL, phenoxazine (2.2g, 12mmol), palladium acetate Pb
(OAc) (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (t-Bu)3HPBF4(0.34g, 1.2mmol), then in hand
Sodium tert-butoxide NaOt-Bu (1.16g, 12mmol) is added in casing, the first that 60mL removes water deoxygenation in advance is squeezed under argon atmosphere
Benzene reacts 24 hours at 120 DEG C.It is cooled to room temperature, reaction solution is poured into 200mL ice water, methylene chloride extracts three times, merges
Organic phase, rotation are isolated and purified at silica gel, column chromatography (methylene chloride: n-hexane, v:v, 3:2), obtain the change of 1.8g grass green powder
Close object 1, yield 66%.
1HNMR(300MHz,CD2Cl2, δ): 8.73 (s, 2H), 8.36 (d, J=6.3Hz, 2H), 7.14-6.90 (m,
18H)。
MS(EI)m/z:[M]+calcd for C35H22N4O3,546.17；found,546.10.
Embodiment 2:
The synthetic route of target compound 2 is as follows:
Raw material 2 (2.09g, 5mmol) is added into bis- mouthfuls of bottles of 100mL, phenoxazine (2.2g, 12mmol), palladium acetate
(90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2mmol), is then added the tert-butyl alcohol in glove box
Sodium (1.16g, 12mmol) squeezes into the toluene that 60mL removes water deoxygenation in advance under argon atmosphere, reacts 24 hours at 120 DEG C.It is cold
But to room temperature, reaction solution is poured into 200mL ice water, methylene chloride extracts three times, merges organic phase, rotation is at silica gel, column chromatography
(methylene chloride: n-hexane, v:v, 3:2) isolates and purifies, and obtains the compound 2 of 1.6g grass green powder, yield 59%.
1H NMR(300MHz,CD2Cl2,δ):8.41(s,2H),8.24(s,2H),7.68(s,2H),7.14-6.90(m,
16H)。
MS(EI)m/z:[M]+calcd for C35H22N4O3,546.17；found,546.13.
Embodiment 3:
The synthetic route of target compound 3 is as follows:
Raw material 3 (2.09g, 5mmol) is added into bis- mouthfuls of bottles of 100mL, phenoxazine (2.2g, 12mmol), palladium acetate
(90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2mmol), is then added the tert-butyl alcohol in glove box
Sodium (1.16g, 12mmol) squeezes into the toluene that 60mL removes water deoxygenation in advance under argon atmosphere, reacts 24 hours at 120 DEG C.It is cold
But to room temperature, reaction solution is poured into 200mL ice water, methylene chloride extracts three times, merges organic phase, rotation is at silica gel, column chromatography
(methylene chloride: n-hexane, v:v, 3:2) isolates and purifies, and obtains the compound 3 of 1.3g green powder, yield 48%.
1H NMR(300MHz,CD2Cl2, δ): 8.17 (s, 2H), 7.72 (d, J=6.3Hz, 2H), 7.14-6.90 (m,
16H), 6.75 (d, J=6.6Hz, 2H).
MS(EI)m/z:[M]+calcd for C35H22N4O3,546.17；found,546.15.
Fig. 1 shows the track arrangement situation of compound 1-3, it is apparent that the highest of compound 1-3 from Fig. 1
Electronics occupies track (HOMO) and do not occupy track (LUMO) from minimum electronics to be arranged on different units respectively, has been realized
Full separation, this facilitates the poor Δ EST of energy between reduction system, to improve reversed intersystem crossing ability.Fig. 2 shows compound 1-
3 photoluminescence spectras in toluene solution at room temperature.For compound 1-3, simulation calculates the minimum singlet energy of molecule
Grade S1 and lowest triplet state energy level T1.
The related data of embodiment 1-3 is as shown in table 1.As can be seen from Table 1, the Δ Est of all compounds is respectively less than
0.3ev, realizes lesser singlet and triplet is poor, has obvious delay fluorescent effect.
The photophysical property result of table 1, compound 1-3
In table 1, PL Peak indicates luminescence generated by light peak, and S1 indicates singlet energy level, and T1 indicates triplet, Δ EST table
Show that singlet and triplet are poor.
Embodiment 4:
The preparation of organic electroluminescent LED (OLED) device:
As described in Figure 1, the organic electroluminescent of thermal activation delayed fluorescence material of the invention as luminescent layer guest materials
Diode component, it may include the substrate 9 that sets gradually from top to bottom, hole injection layer 2, hole transmission layer 3, shines at anode layer 1
Layer 4, electron transfer layer 5 and cathode layer 6.Wherein, the substrate 9 is glass substrate, and the material of the anode 1 is tin indium oxide
(ITO), the substrate 9 collectively forms ito glass with anode 1.The material of the hole injection layer 2 is molybdenum trioxide (MoO3),
The material of the hole transmission layer 3 is TCTA, the material of the luminescent layer be activation delayed fluorescence compound of the invention with
The mixture of mCBP, the material of the electron transfer layer 5 are TmPyPB.The cathode is lithium fluoride (LiF) layer and aluminium (Al) layer
The double-layer structure of composition.
Wherein, TCTA refers to that 4,4', 4 "-three (carbazole -9- base) triphenylamines, mCBP refer to 3,3'- bis- (N- carbazyl) -1,1'-
Biphenyl, TmPyPB refer to 1,3,5- tri- (3- (3- pyridyl group) phenyl) benzene.
The organic electroluminescent diode apparatus can be made by means known in the art, method particularly includes: by clear
On the ito glass washed, the MoO of 2nm thickness is successively deposited under high vacuum condition3Film, 35nm thickness TCTA film, DPEPO add activation to prolong
The Al film of fluorescent chemicals, the Tm3PyPB film of 40nm thickness, the LiF film of 1nm thickness and 100nm thickness late.Such as Fig. 3 is made with this method
Shown in device, various specific device architectures are as follows:
Device 1:
ITO/MoO3(2nm)/TCTA (35nm)/mCBP: compound 1 (5%40nm)/TmPyPB (40nm)/LiF (1nm)/
Al(100nm)
Device 2:
ITO/MoO3(2nm)/TCTA (35nm)/mCBP: compound 2 (5%40nm)/TmPyPB (40nm)/LiF (1nm)/
Al(100nm)
Device 3:
ITO/MoO3(2nm)/TCTA (35nm)/mCBP: compound 3 (5%40nm)/TmPyPB (40nm)/LiF (1nm)/
Al(100nm)
Current versus brightness-voltage characteristic of device 1-3 is surveyed by the source Keithley with corrected silicon photoelectric diode
What amount system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) was completed, electroluminescent light
Spectrum is by French JY company SPEX CCD3000 spectrometer measurement, and all measurements are completed in atmosphere at room temperature.Device 1-3's
Performance data see the table below 2.
Table 2, the results of property based on the device that compound 1-3 is luminescent layer guest materials
| Device | Maximum current efficiency (cd/A) | CIEy | Maximum external quantum efficiency (%) |
| Device 1 | 63.4 | 0.22 | 25.7 |
| Device 2 | 58.7 | 0.24 | 23.8 |
| Device 3 | 66.9 | 0.27 | 26.5 |
In table 2, CIEy is the y-coordinate value of standard CIE color space.
In conclusion the present invention carries out isomerism regulation by the position to electron donor, electron donor position is studied
Material property bring is influenced, the thermal activation delayed fluorescence material with significant TADF characteristic is designed, realizes material emission
Spectrum from blue green light to green range in adjusting；Above-mentioned thermal activation delayed fluorescence material is further applied to organic by the present invention
When the guest materials of electroluminescent diode apparatus, the luminous efficiency of organic electroluminescent diode apparatus can effectively improve,
Organic electroluminescent diode apparatus based on thermal activation delayed fluorescence material of the invention has very high device efficiency.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (10)
1. a kind of thermal activation delayed fluorescence material, which is characterized in that have the chemical structure as shown in following formula one:
Formula one
R indicates chemical group as electron donor, R be in the 1st in pyridine groups,
3rd, the 4th or the 5th, X isOne of.
2. thermal activation delayed fluorescence material as described in claim 1, which is characterized in that the chemical group R of the electron donor
Any one in following group:
3. thermal activation delayed fluorescence material as claimed in claim 2, which is characterized in that be compound 1, compound 2 or chemical combination
The structural formula difference of object 3, the compound 1, compound 2 and compound 3 is as follows:
4. a kind of preparation method of thermal activation delayed fluorescence material, which is characterized in that its chemical synthesis route is as follows:
Specifically: into reaction flask be added molar ratio be 1:2-4:0.05-0.2:0.2-0.4 halogenated raw material, contain electron donor
Then compound, palladium acetate and tri-tert-butylphosphine tetrafluoroborate are 2-4:1's by with halogenated raw material under anhydrous and oxygen-free environment
Molar ratio be added sodium tert-butoxide, squeezed under argon atmosphere water removal deoxygenation toluene, 110-120 DEG C reaction 20-30 hours；It is cold
But to room temperature, reaction solution is poured into ice water, organic phase is merged after extraction, is revolved into silica gel, column chromatographic isolation and purification obtains product,
Calculated yield；
The general structure of the halogenated raw material isWherein, Br be in the 1st in pyridine groups,
3rd, the 4th or the 5th；
The general structure containing electronic donor compound is R-H, wherein R indicates the chemical group as electron donor.
5. the preparation method of thermal activation delayed fluorescence material as claimed in claim 4, which is characterized in that the electron donor
Any one of chemical group R in following group:
6. the preparation method of thermal activation delayed fluorescence material as claimed in claim 5, which is characterized in that described to contain electron donor
Compound is phenoxazine；
The halogenated raw material is raw material 1, raw material 2 or raw material 3, and the structural formula of the raw material 1, raw material 2 and raw material 3 is respectively
7. a kind of organic electroluminescent diode apparatus, which is characterized in that including substrate, the first electricity being set on the substrate
Pole, the organic function layer being set in first electrode and the second electrode being set on the organic function layer；
The organic function layer includes one or more layers organic film, and at least one layer of organic film is luminescent layer；
The luminescent layer includes thermal activation delayed fluorescence compound as claimed in any one of claims 1-3.
8. organic electroluminescent diode apparatus as claimed in claim 7, which is characterized in that the luminescent layer is steamed using vacuum
The method of plating or solution coating is formed.
9. organic electroluminescent diode apparatus as claimed in claim 7, which is characterized in that based on the material of the luminescent layer
The mixture of body material and guest materials, the guest materials are selected from thermal activation as claimed in any one of claims 1-3 and prolong
One of slow fluorescent chemicals are a variety of.
10. organic electroluminescent diode apparatus as claimed in claim 9, which is characterized in that the substrate is glass substrate,
The material of the first electrode is tin indium oxide, and the second electrode is the two-layer composite that layer of lithium fluoride and aluminium layer are constituted；
The organic function layer includes multilayer organic film, which includes hole injection layer, hole transmission layer, hair
Photosphere, electron transfer layer, wherein the material of the hole injection layer is molybdenum trioxide, and the material of the hole transmission layer is
TCTA, the material of the electron transfer layer are TmPyPB, and the material of main part is mCBP.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910305986.6A CN110003194A (en) | 2019-04-16 | 2019-04-16 | Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus |
| PCT/CN2019/085638 WO2020211125A1 (en) | 2019-04-16 | 2019-05-06 | Thermally-activated delayed fluorescent material and preparation method therefor, and organic light-emitting diode device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910305986.6A CN110003194A (en) | 2019-04-16 | 2019-04-16 | Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110003194A true CN110003194A (en) | 2019-07-12 |
Family
ID=67172353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910305986.6A Withdrawn CN110003194A (en) | 2019-04-16 | 2019-04-16 | Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN110003194A (en) |
| WO (1) | WO2020211125A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110563633A (en) * | 2019-08-30 | 2019-12-13 | 武汉华星光电半导体显示技术有限公司 | Blue light thermal activation delay fluorescent material, preparation method thereof and electroluminescent device |
| CN113620973A (en) * | 2021-07-16 | 2021-11-09 | 西北工业大学 | Thermal activation delayed fluorescent material and preparation method and application thereof |
| CN114478487A (en) * | 2022-02-21 | 2022-05-13 | 上海天马微电子有限公司 | Organic compound, organic light-emitting display panel and application thereof |
| CN114702446A (en) * | 2022-05-11 | 2022-07-05 | 山西华辉光电科技有限公司 | Efficient narrow-band deep blue photothermal activation type delayed fluorescent material and preparation and application thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105503766A (en) * | 2015-12-18 | 2016-04-20 | 昆山国显光电有限公司 | Thermal activation delayed fluorescent material and organic electroluminescent device |
| CN106380454A (en) * | 2016-08-16 | 2017-02-08 | 盐城工学院 | Organic electroluminescence materials, a luminescent device and a manufacturing method of the device |
| CN106920883A (en) * | 2015-12-25 | 2017-07-04 | 昆山工研院新型平板显示技术中心有限公司 | A kind of organic electroluminescence device |
| CN107445913A (en) * | 2017-08-15 | 2017-12-08 | 武汉大学 | A kind of fluorescent material of structure containing beta diketone and its preparation and application |
| CN108368045A (en) * | 2015-12-04 | 2018-08-03 | 广州华睿光电材料有限公司 | Thermal excitation delayed fluorescence material, high polymer, mixture, composition and organic electronic device |
| CN108695440A (en) * | 2018-05-30 | 2018-10-23 | 昆山国显光电有限公司 | A kind of organic electroluminescence device |
-
2019
- 2019-04-16 CN CN201910305986.6A patent/CN110003194A/en not_active Withdrawn
- 2019-05-06 WO PCT/CN2019/085638 patent/WO2020211125A1/en active Application Filing
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108368045A (en) * | 2015-12-04 | 2018-08-03 | 广州华睿光电材料有限公司 | Thermal excitation delayed fluorescence material, high polymer, mixture, composition and organic electronic device |
| CN105503766A (en) * | 2015-12-18 | 2016-04-20 | 昆山国显光电有限公司 | Thermal activation delayed fluorescent material and organic electroluminescent device |
| CN106920883A (en) * | 2015-12-25 | 2017-07-04 | 昆山工研院新型平板显示技术中心有限公司 | A kind of organic electroluminescence device |
| CN106380454A (en) * | 2016-08-16 | 2017-02-08 | 盐城工学院 | Organic electroluminescence materials, a luminescent device and a manufacturing method of the device |
| CN107445913A (en) * | 2017-08-15 | 2017-12-08 | 武汉大学 | A kind of fluorescent material of structure containing beta diketone and its preparation and application |
| CN108695440A (en) * | 2018-05-30 | 2018-10-23 | 昆山国显光电有限公司 | A kind of organic electroluminescence device |
Non-Patent Citations (1)
| Title |
|---|
| P. RAJAMALLI等: "New Molecular Design Concurrently Providing Superior Pure Blue，Thermally Activated Delayed Fluorescence and Optical Out-Coupling Efficiencies", 《J. AM. CHEM. SOC.》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110563633A (en) * | 2019-08-30 | 2019-12-13 | 武汉华星光电半导体显示技术有限公司 | Blue light thermal activation delay fluorescent material, preparation method thereof and electroluminescent device |
| CN110563633B (en) * | 2019-08-30 | 2022-11-08 | 武汉华星光电半导体显示技术有限公司 | Blue-light thermal activation delay fluorescent material, preparation method thereof and electroluminescent device |
| CN113620973A (en) * | 2021-07-16 | 2021-11-09 | 西北工业大学 | Thermal activation delayed fluorescent material and preparation method and application thereof |
| CN113620973B (en) * | 2021-07-16 | 2024-05-07 | 西北工业大学 | Thermal activation delay fluorescent material and preparation method and application thereof |
| CN114478487A (en) * | 2022-02-21 | 2022-05-13 | 上海天马微电子有限公司 | Organic compound, organic light-emitting display panel and application thereof |
| CN114702446A (en) * | 2022-05-11 | 2022-07-05 | 山西华辉光电科技有限公司 | Efficient narrow-band deep blue photothermal activation type delayed fluorescent material and preparation and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2020211125A1 (en) | 2020-10-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110003194A (en) | Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus | |
| CN102731406B (en) | Phenanthroimidazole derivatives and application of phenanthroimidazole derivatives in preparation of electroluminescent device | |
| CN109503481A (en) | Thermal activation delayed fluorescence compound and preparation method thereof and organic electroluminescent diode apparatus | |
| WO2020211122A1 (en) | Bipolar thermally activated delayed fluorescence material, preparation method therefor, and organic electroluminescent diode device | |
| CN110003222A (en) | Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus | |
| CN110105330B (en) | Efficient photothermal activation delayed fluorescent material from blue green to orange red and preparation method and application thereof | |
| CN101899296A (en) | Red organic electroluminescent phosphorescent material containing aryl united quinazoline metal iridium complexes and organic electroluminescent device thereof | |
| WO2020098146A1 (en) | Blue light thermally activated delayed fluorescence material and use thereof | |
| US20200194682A1 (en) | Thermally activated delayed fluorescence material and method for preparing thereof and organic electroluminescent diode device | |
| CN106800526A (en) | A kind of electroluminescent organic material and its application with cyclic diketones as core | |
| CN106941133B (en) | A kind of organic luminescent device and preparation method thereof | |
| CN106831791A (en) | One class ethylization pyrazine and quinoxaline derivant and preparation method thereof | |
| CN110003208A (en) | Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus | |
| CN110143960A (en) | Green light thermal activation delayed fluorescence material and preparation method thereof, organic electroluminescence device | |
| CN110003223A (en) | Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus | |
| CN109912505A (en) | Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus | |
| CN109678851A (en) | Hot activation delayed fluorescence material, organic electroluminescence device and display panel | |
| CN109206368A (en) | A kind of dihydrobenzo indazole class electroluminescent organic material | |
| CN109206367A (en) | A kind of organic electroluminescence device and display | |
| CN109970641A (en) | Thermal activation delayed fluorescence material and preparation method thereof and organic electroluminescent diode apparatus | |
| CN105237501A (en) | Organic luminescent material containing spirobifluorene and dibenzofuran and luminescent device | |
| CN110240550A (en) | A kind of thermal activation delayed fluorescence material, preparation method and electroluminescent device | |
| CN109897065B (en) | Thermal activation delayed fluorescent material, preparation method thereof and organic light-emitting diode device | |
| CN110256458A (en) | A kind of thermal activation delayed fluorescence molecule and preparation method thereof, electroluminescent hot activation delayed fluorescence device | |
| CN109535159A (en) | Feux rouges thermal activation delayed fluorescence material, preparation method and organic light emitting diode device |
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 | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20190712 |
|
| WW01 | Invention patent application withdrawn after publication |