CN110526904A - Green light thermal activation delayed fluorescence material and preparation method thereof, electroluminescent device - Google Patents
Green light thermal activation delayed fluorescence material and preparation method thereof, electroluminescent device Download PDFInfo
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- CN110526904A CN110526904A CN201910802431.2A CN201910802431A CN110526904A CN 110526904 A CN110526904 A CN 110526904A CN 201910802431 A CN201910802431 A CN 201910802431A CN 110526904 A CN110526904 A CN 110526904A
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- 239000000463 material Substances 0.000 title claims abstract description 91
- 230000003111 delayed effect Effects 0.000 title claims abstract description 61
- 238000007725 thermal activation Methods 0.000 title claims abstract description 59
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 59
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000605 extraction Methods 0.000 claims abstract description 14
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 239000011259 mixed solution Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 230000005540 biological transmission Effects 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 238000012546 transfer Methods 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000962 organic group Chemical group 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 8
- -1 tri-tert-butylphosphine tetrafluoro boric acid Salt Chemical compound 0.000 claims description 8
- 238000006392 deoxygenation reaction Methods 0.000 claims description 7
- 239000012300 argon atmosphere Substances 0.000 claims description 6
- 230000008859 change Effects 0.000 claims description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 abstract description 5
- 150000004892 pyridazines Chemical class 0.000 abstract description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 229960001866 silicon dioxide Drugs 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
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- 239000002585 base Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
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- 238000011049 filling Methods 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
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- 230000035484 reaction time Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N acetic acid;palladium Chemical compound [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
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- 230000005494 condensation Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
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- 238000010168 coupling process Methods 0.000 description 1
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- 238000013461 design Methods 0.000 description 1
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- 239000003814 drug Substances 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical group O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- DENHERDSBFPKKO-UHFFFAOYSA-N sodium;argon;2-methylpropan-2-olate Chemical group [Na+].[Ar].CC(C)(C)[O-] DENHERDSBFPKKO-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- 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
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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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- 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
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The present invention provides a kind of green light thermal activation delayed fluorescence materials and preparation method thereof, electroluminescent device.The present invention passes through on the basis of s-triazine structure, it connects 3 pyridazines and reinforces its electron-withdrawing ability, it is a series of poor with lower single triplet to have synthesized, high-luminous-efficiency, the quickly green light thermal activation delayed fluorescence material of reversed intersystem crossing constant, it includes the aromatic organic radicals of nitrogen.The green light thermal activation delayed fluorescence material is made by reaction solution preparation steps, synthesis step, extraction step, separating-purifying step, and it is applied to the luminescent layer of electroluminescent device, the luminescent layer has lower single triplet poor, to solve the problems, such as that the theoretical internal quantum efficiency of fluorescent material is low, and then improve the luminous efficiency of electroluminescent device.
Description
Technical field
The present invention relates to field of display technology more particularly to a kind of green light thermal activation delayed fluorescence material and its preparation sides
Method, electroluminescent device.
Background technique
Organic electroluminescent LED (organic light-emitting diode, OLED) is shone with its active and is not required to
Want that backlight, luminous efficiency are high, visible angle is big, fast response time, Acclimation temperature range are big, production and processing technology is relatively simple
The advantages that list, driving voltage are low, and energy consumption is small, lighter and thinner, Flexible Displays and huge application prospect, have attracted numerous researchs
The concern of person.
In OLED, the light emitting guest material to play a leading role is most important.The light-emitting guest material that the OLED of early stage is used
Material is fluorescent material, since the exciton ratio of the singlet state in OLED and triplet is 1:3, the OLED based on fluorescent material
Theoretical internal quantum efficiency (IQE) can only achieve 25%, significantly limit the application of fluorescence electroluminescent device.Heavy metal is matched
Object phosphor material is closed due to the Effect of Spin-orbit Coupling of heavy atom, allows it to utilize singlet state and triplet exciton simultaneously
And the IQE of realization 100%.However, usually used heavy metal is all the precious metals such as Ir, Pt, and heavy metal complex phosphorus
Light luminescent material still needs to be broken through in terms of blue light material.Pure organic thermal activation delayed fluorescence (TADF) material, by cleverly
MOLECULE DESIGN, so that molecule has the lesser minimum triple energy level differences of list (Δ EST), such triplet exciton can be by reversed
Intersystem crossing (RISC) returns to singlet state, then is shone by radiation transistion to ground state, so as to utilize single, triplet simultaneously
100% IQE also may be implemented in exciton.For green light thermal activation delayed fluorescence material, quick reversed intersystem crossing constant
(kRISC) and high photoluminescence quantum yield (PLQY) be the necessary condition for preparing high efficiency OLED.Currently, having above-mentioned
The green light thermal activation delayed fluorescence material of condition is still deficienter for heavy metal Ir complex.
The present invention by the basis of s-triazine structure in view of the above-mentioned problems, connecting 3 pyridazines and reinforcing its electrophilic energy
Then power adjusts whole electric charge transfer power by different electron units, synthesized a series of with lower three line of list
State energy level difference, high-luminous-efficiency, quickly the green light thermal activation delayed fluorescence material of reversed intersystem crossing constant, realizes simultaneously
The electron donation of electron unit is finely tuned so that spectrum is finely tuned.Confirmed by structure of the mass spectral analysis to them, then
Their Photophysics are studied in detail, these green light thermal activation delayed fluorescence materials are applied to hair by last base
Photosphere is prepared for a series of high performance OLED.
Summary of the invention
The present invention provides a kind of green light thermal activation delayed fluorescence materials and preparation method thereof, electroluminescent device, pass through
Reinforce its electron-withdrawing ability by the basis of s-triazine structure, connecting 3 pyridazines, then by different electron units come
It is strong and weak to adjust whole electric charge transfer, having synthesized has lower single triplet poor, solves amount in the theory of fluorescent material
The problem of sub- low efficiency, to improve the luminous efficiency of electroluminescent device.
In order to achieve the goal above, chemical structure is logical the present invention provides a kind of green light thermal activation delayed fluorescence material
Formula is as follows:
Wherein, R1, R2, R3 are that the aromatic series comprising nitrogen is organic
Group.
Further, any one of described R1, R2, R3 in following organic groups:
The present invention also provides a kind of preparation methods of green light thermal activation delayed fluorescence material, comprising the following steps:
Electron acceptor, electron donor, catalyst and highly basic are placed in reaction vessel by reaction solution configuration step, are obtained anti-
Answer liquid；The chemical structural formula of the electron acceptor is as follows:
Wherein R4, R5, R6 are expressed as any one of Cl, Br or I；
The electron donor includes the aromatic organic radicals of Nitrogen element；
Green light thermal activation delayed fluorescence materials synthesis step, is reacted at 100 DEG C~140 DEG C, obtains one with described
The mixed solution of green light thermal activation delayed fluorescence material；
The mixed solution is cooled to room temperature by extraction step, extracts the green light thermal activation in the mixed solution
Delayed fluorescence material obtains a mixture；
The mixture made from the extraction step is isolated and purified to obtain a green powder by purification procedures, is obtained
The green light thermal activation delayed fluorescence material, general formula of the chemical structure are
Wherein, R1, R2, R3 are that the aromatic series comprising nitrogen is organic
Group.
Further, any one of described R1, R2, R3 in following organic groups:
Further, in the reaction solution preparation steps, first by the electron donor, the electron acceptor, the acetic acid
Palladium and the tri-tert-butylphosphine tetrafluoroborate are placed in together in the reaction vessel, are then passed through the reaction vessel
The sodium tert-butoxide is added into the glove box of argon atmosphere in transfer chamber in the glove box, and examination is added and first removes water deoxygenation
Toluene obtains the reaction solution.
It further, include: that described will be mixed using solvent by silica gel column chromatography method in the purification procedures
It closes object and carries out purification process, obtain the green light thermal activation delayed fluorescence material；Wherein, the exhibition in the silica gel column chromatography method
Opening agent is methylene chloride and normal hexane.
Further, the molar ratio of the electron acceptor and electron donor is 1:1-1:4.
The present invention also provides a kind of electroluminescent devices comprising above-mentioned blue light thermal activation delayed fluorescence material.
Further, the electroluminescent device includes luminescent layer, and the luminescent layer material therefor is living for the blue light heat
Change delayed fluorescence material.
Further, the electroluminescent device further include: substrate layer；Hole injection layer is set to the substrate layer side
Surface；Hole transmission layer is set to hole injection layer far from one side surface of substrate layer；The luminescent layer is set to the hole transmission layer
Far from one side surface of hole injection layer；Electron transfer layer is set to the luminescent layer far from hole transmission layer side table
Face；Cathode layer is set to electron transfer layer far from one side surface of luminescent layer.
The beneficial effects of the present invention are: the present invention by the basis of s-triazine structure, connecting 3 pyridazines by being reinforced
Its electron-withdrawing ability, it is strong and weak then to adjust whole electric charge transfer by different electron units, and having synthesized a series of has
Lower list triplet is poor, high-luminous-efficiency, quickly the green light thermal activation delayed fluorescence material of reversed intersystem crossing constant,
Simultaneously realize electron unit electron donation finely tune so that spectrum finely tune, effectively increase material luminous efficiency,
At the same time, studying the strong and weak of charge transfer state influences material property bring, is finally postponed based on the thermal activation of target green light
The electroluminescent device of fluorescent material all achieves very high efficiency, improves the luminous efficiency of organic electroluminescence device.
Detailed description of the invention
The present invention is further explained with reference to the accompanying drawings and examples.
Fig. 1 is the synthetic method flow chart of green light thermal activation delayed fluorescence material described in the embodiment of the present invention.
Fig. 2 is the structural schematic diagram of electroluminescent device described in the embodiment of the present invention.
Specific embodiment
Below in conjunction with the attached drawing in the embodiment of the present application, technical solutions in the embodiments of the present application carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of embodiments of the present application, instead of all the embodiments.It is based on
Embodiment in the application, those skilled in the art's every other implementation obtained without creative efforts
Example, shall fall in the protection scope of this application.However the present invention can be emerged from by many various forms of embodiments, this
The protection scope of invention is not limited only to the embodiment mentioned in text, what the explanation of Examples below was not intended to limit the invention
Range.
Referenced herein " embodiment " is it is meant that a particular feature, structure, or characteristic described can wrap in conjunction with the embodiments
It is contained at least one embodiment of the application.Each position in the description occur the phrase might not each mean it is identical
Embodiment, nor the independent or alternative embodiment with other embodiments mutual exclusion.Those skilled in the art explicitly and
Implicitly understand, embodiment described herein can be combined with other embodiments.
The present invention provides a kind of green light thermal activation delayed fluorescence material, general formula of the chemical structure is as follows:
Wherein, R1, R2, R3 are the aromatic organic radicals comprising nitrogen.
Further, any one or more combination of described R1, R2, R3 in following organic groups:
Referring to Fig. 1, Fig. 1 discloses the preparation method of green light thermal activation delayed fluorescence material of the present invention.Green light of the present invention
The preparation of thermal activation delayed fluorescence material includes the following steps that S10 reaction solution configures, S20 green light thermal activation delayed fluorescence material
Synthesis, S30 extraction and S40 are isolated and purified.
Step S10, reaction solution configuration step mix electron acceptor and electron donor with molar ratio for 1:1-1:4 ratio,
Addition catalyst is placed in the reaction vessel of strong alkali environment, obtains reaction solution；The chemical structural formula of the electron acceptor is as follows:
R4, R5, R6 are expressed as any one of Cl, Br or I；
The electron donor includes the aromatic organic radicals of Nitrogen element；The aromatic organic radicals of the Nitrogen element
Any one in following organic groups:
Preferably, the electron donor is carbazole, phenoxazine, 9, at least one of 9 '-dimethyl acridiniums；The catalysis
Agent is palladium acetate and tri-tert-butylphosphine tetrafluoroborate；The highly basic is sodium tert-butoxide.The sodium tert-butoxide, it is extensive as highly basic
Applied in the reaction such as condensation, rearrangement and open loop in chemical industry, medicine, pesticide and organic synthesis；Since the sodium tert-butoxide is high
The performances such as inflammable, chance water reaction is violent are spent, usually the sodium tert-butoxide is stored in the glove box of inert atmosphere.The acetic acid
Palladium and the tri-tert-butylphosphine tetrafluoro boric acid reactant salt produce tri-tert-butylphosphine palladium, and the tri-tert-butylphosphine palladium performance is relatively more living
It sprinkles, is difficult to save, but be the important catalyst of this reaction.
The reaction solution prepares that specific step is as follows, first by the electron acceptor, the electron donor, the palladium acetate with
And the tri-tert-butylphosphine tetrafluoroborate is placed in together in the reaction vessel, and the reaction vessel is then passed through transition
The sodium tert-butoxide is added into the glove box of argon atmosphere in cabin in the glove box, and the toluene that examination first removes water deoxygenation is added,
Obtain the reaction solution.It carries out, needs in order to avoid the sodium tert-butoxide and the tri-tert-butylphosphine palladium chemical activity influence reaction
It tries that glove box internal atmosphere is first changed to argon atmosphere, and the first of water removal deoxygenation is added in glove box reaction vessel simultaneously
Reaction solution is made in benzene.
Step S20, green light thermal activation delayed fluorescence materials synthesis carry out sufficiently reaction 13~25 at 100 DEG C~140 DEG C
Hour, a mixed solution with the green light thermal activation delayed fluorescence material is obtained, in order to guarantee catalyst and the tertiary fourth
The activity and security performance of sodium alkoxide, the reaction process carry out in glove box.Wherein reaction temperature is preferably 120 DEG C, instead
Preferably 24 hours between seasonable.
Step S30, extraction, reaction solution is poured into mixture of ice and water, and methylene chloride is added and is repeatedly extracted；Repeatedly
Merge organic phase after extraction, obtains mixture.
Step S40, isolates and purifies, and using solvent, mixture is carried out purification process by silica gel column chromatography method, system
The mixture obtained isolates and purifies to obtain a green powder, has both been the green light thermal activation delayed fluorescence material；The solvent
For methylene chloride and normal hexane, the volume ratio of the methylene chloride and the nalka is 1:5.
The purification step obtains the green light thermal activation delayed fluorescence material, and general formula of the chemical structure is
Any one of described R1, R2, R3 in following organic groups:
Further the preparation method of the green light thermal activation delayed fluorescence material is carried out with following three specific embodiments
Explanation.
Embodiment 1
The present invention provides a kind of preparation method of cavitation material, synthetic route is as follows:
Synthesis step includes: reaction solution preparation step S10, and electron donor raw material 1 is added into 100mL reaction vessel
(2.74g, 5mmol), carbazole (3.01g, 18mmol), palladium acetate (135mg, 0.6mmol) and tri-tert-butylphosphine tetrafluoro boric acid
Then the reaction vessel is passed through transfer chamber into glove box by salt (0.51g, 1.8mmol), the glove box internal atmosphere is
Sodium tert-butoxide (NaOt-Bu 1.74g, 18mmol) is added in glove box into reaction vessel again for argon atmosphere, continues
The toluene that 120mL removes water deoxygenation in advance is added into reaction vessel, obtains a reaction solution.
The synthesis step S20 of green light thermal activation delayed fluorescence material reacts reaction vessel at 110 DEG C~130 DEG C
13~25 hours obtain a mixed solution.The reaction process carries out in glove box.Wherein reaction temperature is preferably 120
DEG C, the reaction time is preferably 24 hours.
Mixed solution will be cooled to after room temperature and pours into 300mL ice water by extraction step S30, and methylene chloride extracts three times,
Obtain a mixture.
The organic phase of mixture made from extraction step is merged, is put into the silica gel of filling gel by purification procedures S40
In column, by volume ratio be 1:1 methylene chloride and n-hexane mixed liquor carry out silicagel column flushing, by the washing lotion of collection into
The dry evaporation of row, obtains green powder 2.1g, the as described green light thermal activation delayed fluorescence material.Green light heat made from the method is living
Change the yield 52% of delayed fluorescence material, mass spectral analysis MS (EI) m/z:810.18.
Embodiment 2
The present invention provides a kind of preparation method of cavitation material, synthetic route is as follows:
Synthesis step includes: reaction solution preparation step S10, and electron acceptor raw material 1 is added into 100mL reaction vessel
(2.74g, 5mmol), phenoxazine (2.03g, 12mmol), palladium acetate (135mg, 0.6mmol) and tri-tert-butylphosphine tetrafluoro boron
Then reaction vessel is passed through transfer chamber into glove box by hydrochlorate (0.51g, 1.8mmol), the glove box internal atmosphere is argon
Sodium tert-butoxide (NaOt-Bu 1.74g, 18mmol) is added in glove box into reaction vessel again for gas atmosphere, continue to
The toluene that 120mL removes water deoxygenation in advance is added in reaction vessel, obtains a reaction solution.
The synthesis step S20 of green light thermal activation delayed fluorescence material reacts reaction vessel at 110 DEG C~130 DEG C
13~25 hours obtain a mixed solution.The reaction process carries out in glove box.Wherein reaction temperature is preferably 120
DEG C, the reaction time is preferably 24 hours.
Mixed solution will be cooled to room temperature and pours into 300mL ice water by extraction step S30, and methylene chloride extracts three times, obtain
One mixture.
The organic phase of mixture made from extraction step is merged, is put into the silica gel of filling gel by purification procedures S40
In column, by volume ratio be 1:1 methylene chloride and n-hexane mixed liquor carry out silicagel column flushing, by the washing lotion of collection into
The dry evaporation of row, obtains green powder 2.3g, the as described green light thermal activation delayed fluorescence material.Green light heat made from the method is living
Change the yield 54% of delayed fluorescence material, mass spectral analysis MS (EI) m/z:858.12.
Embodiment 3
The present invention provides a kind of preparation method of cavitation material, synthetic route is as follows:
Synthesis step includes: reaction solution preparation step S10, and electron donor raw material 1 is added into 100mL reaction vessel
((2.74g, 5mmol), 9,9 '-dimethyl acridiniums (2.51g, 12mmol), palladium acetate (135mg, 0.6mmol) and three tertiary fourths
Then reaction vessel is passed through transfer chamber into glove box, in the glove box by base phosphine tetrafluoroborate (0.51g, 1.8mmol)
Portion's atmosphere is argon atmosphere, and sodium tert-butoxide (NaOt-Bu 1.74g, 18mmol) is added in glove box to reaction vessel again
In, continue that the toluene that 120mL removes water deoxygenation in advance is added into reaction vessel, obtains a reaction solution.
The synthesis step S20 of green light thermal activation delayed fluorescence material reacts reaction vessel at 110 DEG C~130 DEG C
13~25 hours obtain a mixed solution.The reaction process carries out in glove box.Wherein reaction temperature is preferably 120
DEG C, the reaction time is preferably 24 hours.
Mixed solution will be cooled to room temperature and pours into 300mL ice water by extraction step S30, and methylene chloride extracts three times, obtain
One mixture.
The organic phase of mixture made from extraction step is merged, is put into the silica gel of filling gel by purification procedures S40
In column, by volume ratio be 1:1 methylene chloride and n-hexane mixed liquor carry out silicagel column flushing, by the washing lotion of collection into
The dry evaporation of row, obtains green powder 2.6g, the as described green light thermal activation delayed fluorescence material.Green light heat made from the method is living
Change the yield 56% of delayed fluorescence material, mass spectral analysis MS (EI) m/z:936.29.
The minimum singlet state (S1) of green light thermal activation delayed fluorescence material molecule made from three specific embodiments of the invention
With lowest triplet state energy level (T1), electrochemistry energy level is as shown in table 1 below.
| PL peak value (nm) | S1(eV) | T1(eV) | EST(eV) | HOMO(eV) | LUMO(eV) | |
| Embodiment 1 | 523 | 2.37 | 2.20 | 0.17 | -5.56 | -2.87 |
| Embodiment 2 | 540 | 2.30 | 2.18 | 0.12 | -5.42 | -2.87 |
| Embodiment 3 | 533 | 2.33 | 2.26 | 0.07 | -5.61 | -2.87 |
Table 1
It can thus be appreciated that the minimum singlet state (S1) of green light thermal activation delayed fluorescence material of the method synthesis and minimum triple
State energy level (T1) is lower.
The present invention also provides a kind of electroluminescent devices 100, as shown in Fig. 2, electroluminescent device 100 includes: substrate
Layer 101, hole injection layer 102, hole transmission layer 103, luminescent layer 104, electron transfer layer 105, cathode layer 106.
Hole injection layer 102 is set to 101 1 side surface of substrate layer, and hole transmission layer 103 is set to hole injection layer 102
Far from 101 1 side surface of substrate layer, luminescent layer 104 is set to the hole transmission layer 103 far from 102 side of hole injection layer
Surface, electron transfer layer 105 are set to the luminescent layer 104 far from 103 1 side surface of hole transmission layer, and cathode layer 106 is set
In electron transfer layer 105 far from 104 1 side surface of luminescent layer.
Wherein 101 material therefor of substrate layer is tin indium oxide (ITO), and 102 material therefor of hole injection layer is three oxygen
Change molybdenum (MoO3), 103 material therefor of hole transmission layer be 4,4', 4 "-three (carbazole -9- base) triphenylamines (TCTA), luminescent layer 104
Material therefor is the revealed green light thermal activation delayed fluorescence material (mCBP) of previous embodiment, and electron transfer layer material therefor is
1051,3,5- tri- (3- (3- pyridyl group) phenyl) benzene (Tm3PyPB), 106 material therefor of cathode layer are lithium fluoride/aluminium (LiF/
Al)。
When luminescent layer 104 is using three above specific embodiment material, device 1, device 2 and device 3 are respectively obtained.It is right
The electroluminescent device 100 being made of last time material is tested for the property.The current versus brightness-of electroluminescent device 100 when measurement
Voltage characteristic is the source the Keithley measuring system (Keithley 2400 by having corrected silicon photoelectric diode
2000 Currentmeter of Sourcemeter, Keithley) complete, electroluminescent spectrum is by French JY company SPEX
CCD3000 spectrometer measurement, all measurements are completed in atmosphere at room temperature.Specific device 1 when measurement, device 2, device 3
The parameter of each layer is as follows:
Device 1:
ITO/MoO3(2nm)/TCTA (35nm)/mCBP: compound 1 (10%, 20nm)/Tm3PyPB (40nm)/LiF
(1nm)/Al(100nm)；
Device 2:
ITO/MoO3(2nm)/TCTA (35nm)/mCBP: compound 2 (10%, 20nm)/Tm3PyPB (40nm)/LiF
(1nm)/Al(100nm)；
Device 3:
ITO/MoO3(2nm)/TCTA (35nm)/mCBP: compound 3 (10%, 20nm)/Tm3PyPB (40nm)/LiF
(1nm)/Al(100nm)；
Performance data such as the following table 2 of the measurement gained electroluminescent device 100.
| Device | Maximum current efficiency (cd/A) | Luminescence peak (nm) | Maximum external quantum efficiency (%) |
| Device 1 | 69.5 | 529 | 24.5 |
| Device 2 | 66.3 | 551 | 22.3 |
| Device 3 | 68.0 | 542 | 23.9 |
Table 2
In conclusion the green light thermal activation delayed fluorescence material that the application OLED device uses the application to disclose is as luminous
Layer 104, solves the problems, such as that the theoretical internal quantum efficiency of fluorescent material is low, to improve the luminous efficiency of electroluminescent device.
The present invention reinforces its electron-withdrawing ability by the basis of s-triazine structure, connecting 3 pyridazines, then passes through different electrons
Unit is strong and weak to adjust whole electric charge transfer, and it is a series of poor with lower single triplet to have synthesized, high-luminous-efficiency, fastly
The green light thermal activation delayed fluorescence material of the reversed intersystem crossing constant of speed, while realizing the electron donation of electron unit
Fine tuning is so that spectrum fine tuning at the same time, studies the power of charge transfer state to material in the luminous efficiency for effectively increasing material
Expect that performance bring influences, the electroluminescent device finally based on target green light thermal activation delayed fluorescence material all achieves very
High efficiency improves the luminous efficiency of organic electroluminescence device.
Above to a kind of green light thermal activation delayed fluorescence material provided by the embodiment of the present application and preparation method, electroluminescent hair
Optical device is described in detail, and specific examples are used herein to illustrate the principle and implementation manner of the present application,
The description of the example is only used to help understand the method for the present application and its core ideas；Meanwhile for the skill of this field
Art personnel, according to the thought of the application, there will be changes in the specific implementation manner and application range, in conclusion this
Description should not be construed as the limitation to the application.
Claims (10)
1. a kind of green light thermal activation delayed fluorescence material, which is characterized in that its general formula of the chemical structure is as follows:
Wherein, R1, R2, R3 are the aromatic organic radicals comprising nitrogen.
2. green light thermal activation delayed fluorescence material according to claim 1, which is characterized in that described R1, R2, R3 are selected from down
State any one in organic group:
3. a kind of preparation method of green light thermal activation delayed fluorescence material, which comprises the following steps:
Electron acceptor, electron donor, catalyst and highly basic are placed in reaction vessel by reaction solution configuration step, obtain reaction solution；
The chemical structural formula of the electron acceptor is as follows:
Wherein R4, R5, R6 are expressed as any one of Cl, Br or I；It is described
Electron donor includes the aromatic organic radicals of Nitrogen element；
Green light thermal activation delayed fluorescence materials synthesis step, is reacted at 100 DEG C~140 DEG C, and obtaining one has the green light
The mixed solution of thermal activation delayed fluorescence material；
The mixed solution is cooled to room temperature by extraction step, extracts the green light thermal activation delay in the mixed solution
Fluorescent material obtains a mixture；
The mixture made from the extraction step is isolated and purified to obtain a green powder, described in acquisition by purification procedures
Green light thermal activation delayed fluorescence material, general formula of the chemical structure areWherein
R1, R2, R3 are the aromatic organic radicals comprising nitrogen.
4. the preparation method of green light thermal activation delayed fluorescence material according to claim 3, which is characterized in that the R1, R2,
Any one of R3 in following organic groups:
5. the preparation method of green light thermal activation delayed fluorescence material according to claim 3, which is characterized in that the reaction solution
In preparation steps, first by the electron donor, the electron acceptor, the palladium acetate and the tri-tert-butylphosphine tetrafluoro boric acid
Salt is placed in together in the reaction vessel, and the reaction vessel is then passed through transfer chamber into the glove box of argon atmosphere,
The sodium tert-butoxide is added in the glove box, the toluene that examination first removes water deoxygenation is added, obtains the reaction solution.
6. the preparation method of green light thermal activation delayed fluorescence material according to claim 3, which is characterized in that the separation is pure
Change in step and includes:
Using solvent, the mixture is carried out by purification process by silica gel column chromatography method, obtains the green light thermal activation
Delayed fluorescence material；
Wherein, the solvent in the silica gel column chromatography method is methylene chloride and normal hexane.
7. the preparation method of blue light thermal activation delayed fluorescence material according to claim 3, which is characterized in that the electronics by
The molar ratio of body and electron donor is 1:1-1:4.
8. a kind of electroluminescent device comprising blue light thermal activation delayed fluorescence material described in claim 1.
9. electroluminescent device according to claim 8, which is characterized in that including
Luminescent layer, the luminescent layer material therefor are the blue light thermal activation delayed fluorescence material.
10. electroluminescent device according to claim 8, which is characterized in that further include:
Substrate layer；
Hole injection layer is set to one side surface of substrate layer；
Hole transmission layer is set to hole injection layer far from one side surface of substrate layer；
The luminescent layer is set to the hole transmission layer far from one side surface of hole injection layer；
Electron transfer layer is set to the luminescent layer far from one side surface of hole transmission layer；And
Cathode layer is set to electron transfer layer far from one side surface of luminescent layer.
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