CN110128443A - A kind of thermal activation delayed fluorescence compound, preparation method and its application - Google Patents
A kind of thermal activation delayed fluorescence compound, preparation method and its application Download PDFInfo
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- CN110128443A CN110128443A CN201910481789.XA CN201910481789A CN110128443A CN 110128443 A CN110128443 A CN 110128443A CN 201910481789 A CN201910481789 A CN 201910481789A CN 110128443 A CN110128443 A CN 110128443A
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- delayed fluorescence
- thermal activation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
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- 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
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Abstract
The present invention provides a kind of thermal activation delayed fluorescence compounds comprising donor monomer D and receptor unit A, the general structure used are as follows: Dn- A (n=1 or 2 or 3).Wherein include diphenylamino molecular structure in the molecular structure of the donor monomer D, and in the molecular structure of the receptor unit A includes trimerization dioxo benzothiophene kind molecular structure.The present invention provides a kind of thermal activation delayed fluorescence compounds, structure between its novel donor used and receptor, so that the compound molecule has high intersystem crossing rate constant and anti-intersystem crossing rate constant, so as to effectively inhibit the reduction of the radiation transistion rate as caused by energy gap rule, to obtain high PLQY, so realize high efficiency, it is weak roll-off, application of the dark red smooth TADF compound-material in electroluminescent device.
Description
Technical field
The present invention relates to the functional layer in OLED display panel be related to using Material Field, in particular, it is therein shine
Layer be related to using thermal activation delayed fluorescence (TADF) compound-material.
Background technique
It is known that Organic Light Emitting Diode (organic lighting-emitting diodes, OLEDs) is sent out due to active
Light, visible angle are big, corresponding speed is fast, Acclimation temperature range is wide, driving voltage is low, small power consumption, brightness is big, production technology is simple
It is single, frivolous and can be with Flexible Displays the advantages that, show huge application prospect, attracted the pass of researcher and company
Note.
Currently, Samsung, LG have been carried out and apply OLEDs on mobile phone screen.Further, in OLED display panel
In, it is conclusive that can luminescent layer use the superiority and inferiority of material realize that industrialization is played the role of to OLED display panel.It is specific next
It says, OLED display panel emitting layer material is usually made of subject and object luminescent material, wherein the luminous efficiency of luminescent material
It is two important indicators of luminescent material quality with the service life.
The OLED luminescent material of early stage is conventional fluorescent material, and the exciton ratio of singlet state therein and triplet is 1:3,
Its due to be can only using singlet excitons shine, using the OLED display panel theoretical internal quantum of conventional fluorescent material
Efficiency is only 25%.
In this regard, industry introduces heavy metal cooperation phosphor material in luminescent material, wherein due to the weight being introduced into material
The Quantum geometrical phase effect of atom, so as to realize 100% utilization rate of singlet excitons and triplet exciton；And
It also has been used in feux rouges now and green light OLED is shown.
But the usually used heavy metal of phosphor material generally comprises the heavy metals such as Ir, Pt, Os, these heavy metals are also
Noble metal, it is not only at high cost, but also be more toxic.In addition, the volume production of efficient, the long-life phosphorescent metal complex material uses
Still there is greatly challenge to industry.
2012, Adachi et al. proposed the pure luminescent organic molecule of " thermal activation delayed fluorescence " (TADF) mechanism, led to
Reasonable D-A structure MOLECULE DESIGN is crossed, so that molecule has lesser minimum singlet state and triple energy level differences (Δ EST), in this way
Triplet exciton can return to singlet state by anti-intersystem crossing (RISC), then be shone by radiation transistion to ground state, thus
100% utilization rate of exciton can may be implemented, while not needing the participation of heavy metal simultaneously using single, triplet exciton.
Further, for TADF material, small Δ EST and high photoluminescence quantum yield (PLQY) are systems
The necessary condition of standby high efficiency OLED.Currently, green light and day blue light TADF material have obtained the external quantum efficiency more than 30%
(EQE)；But long wavelength TADF material can not obtain excellent device performance since energy gap is regular (Energy gap law).
Therefore, in the prior art to overcome it is necessory to research and develop a kind of novel thermal activation delayed fluorescence compound
Defect.
Summary of the invention
It is an aspect of the invention to provide a kind of thermal activation delayed fluorescence compound, the novel donor and receptor that use
Between structure so that complex molecule have high intersystem crossing rate constant and anti-intersystem crossing rate constant, so as to
Enough reductions for effectively inhibiting the radiation transistion rate as caused by energy gap rule to obtain high PLQY, and then are realized efficient
Rate, it is weak roll-off, application of the dark red smooth TADF material in electroluminescent device.
The technical solution adopted by the invention is as follows:
A kind of thermal activation delayed fluorescence compound comprising donor monomer D and receptor unit A, the general structure used
Are as follows: Dn- A, wherein n=1 or 2 or 3.It wherein include diphenylamino structure in the structure of the donor monomer D, and the receptor list
It include trimerization dioxo benzothiophene class formation in the structure of first A.
Further, in different embodiments, wherein the general formula of molecular structure that uses of the donor monomer D for following formula or
It is one of following formula derivative:
Further, in different embodiments, wherein the general formula of molecular structure that the receptor unit A is used is led to be following
One of formula:
Further, it is a further aspect of the present invention to provide a kind of thermal activation delayed fluorescence chemical combination of the present invention
The preparation method of object, comprising the following steps:
It step S1, will be using the donor monomer material for including diphenylamino molecular structure and including trimerization dioxo benzo thiophene
The receptor unit material of pheno class molecular structure, which is dissolved in solvent, forms mixed solution；
Step S2, the described mixed solution carries out 20~30h of back flow reaction in 70~95 DEG C of temperature ranges；
Step S3, it is cooled to 15~40 DEG C of temperature ranges after reaction, the reaction solution is extracted, wash, is done
It is dry, filter and be spin-dried for processing obtain surplus materials；And
Step S4, to the surplus materials using 200-300 mesh silica gel carry out column chromatography, and then obtain the present invention relates to
The thermal activation delayed fluorescence compound.
Further, in different embodiments, wherein further including to the mixed solution argon in the step S1
Gas carries out substituting gas disposal.
Further, in different embodiments, wherein in the step S1, the solvent includes toluene and potassium carbonate
Aqueous solution.
Further, in different embodiments, wherein in the step S2, also added with catalysis in the mixed solution
Four triphenyl phosphorus palladium of agent.
Further, in different embodiments, wherein in the step S3, the extractant that the extraction processing uses
Including DCM (dichloromethane, methylene chloride).
Further, in different embodiments, it wherein in the step S4, is drenched used in the column Image processing
Washing lotion includes petroleum ether and the mixed liquor of DCM.
Further, in different embodiments, wherein in the step S4, in the petroleum ether and DCM mixed liquor
The volume ratio of the two is (0.8~1.5): 1.
Further, it is a further aspect of the present invention to provide a kind of thermal activation delayed fluorescence chemical combination of the present invention
The application of object, for for constituting the luminescent layer being arranged in a kind of OLED display panel electroluminescent device.
Further, in different embodiments, wherein the luminescent layer further includes another material of main part 4,4 '-N, N '-
Two carbazole biphenyls (CBP).
Compared with the existing technology, the beneficial effects of the present invention are: a kind of thermal activation delayed fluorescence chemical combination of the present invention
Object uses cleverly Molecular Design, has synthesized a series of long wavelength's heat of the benzothiophene of dioxo containing trimerization receptoroids
Activate delayed fluorescence molecule.
Due to containing sulfuryl structure in the receptor unit molecular structure in this kind of molecule, while there is super plane configuration,
So that the complex molecule has high intersystem crossing rate constant and anti-intersystem crossing rate constant, and then can have
Effect inhibits the reduction of the radiation transistion rate as caused by energy gap rule, to obtain high PLQY.
Further, since super plane shows biggish rigidity again, to effectively increase the steady of the compound
It is qualitative, and then the service life of its applied electroluminescent device can be effectively improved.
Detailed description of the invention
To describe the technical solutions in the embodiments of the present invention more clearly, make required in being described below to embodiment
Attached drawing is briefly described, it should be apparent that, drawings in the following description are only some embodiments of the invention, for
For those skilled in the art, without creative efforts, it can also be obtained according to these attached drawings other attached
Figure.
Fig. 1 is a kind of thermal activation delayed fluorescence compound that the specific embodiment of the present invention is related to, fluorescence hair
Penetrate spectrogram；
Fig. 2 is the thermal activation delayed fluorescence compound of the present invention, is applied to involved in OLED display panel
Electroluminescent device structural schematic diagram.
Specific embodiment
Below with reference to drawings and examples, to a kind of thermal activation delayed fluorescence (TADF) compound of the present invention,
Preparation method and its technical solution of application are described in further detail.
It is an aspect of the invention to provide a kind of thermal activation delayed fluorescence compounds comprising donor monomer D and receptor
Unit A, wherein the donor monomer D and receptor unit A are combined into Dn- A structure, wherein n=1,2 or 3.The wherein donor list
Include diphenylamino molecular structure in the structure of first D, and in the structure of the receptor unit A includes trimerization dioxo benzothiophene
Class molecular structure.
Specifically, wherein the general formula of molecular structure that the donor monomer D is used is in following formula or following formula derivative
It is a kind of:
Further, in different embodiments, wherein the general formula of molecular structure that uses of the receptor unit A for following formula or
It is one of following formula derivative:
Further, due to inventive concept according to the present invention, the thermal activation delayed fluorescence chemical combination of the present invention
Object is long wavelength's thermal activation delayed fluorescence compound of a series of benzothiophene of dioxo containing trimerization receptoroid, therefore, below
The explanation of a citing formula will be done by taking one such specific molecular structure of compounds as an example.
A kind of long wavelength TADF compound of the benzothiophene of dioxo containing trimerization receptoroid of the present invention is (for convenient for after
Continuous description, is denoted as target compound 1), the general formula of molecular structure used is as follows:
Further, the synthetic route that the target compound 1 uses is as follows:
Specifically comprising step in detail below:
Step S1, by the receptor unit A:3 of selection, 8,13- tri- bromo- trimerization dioxo benzothiophenes (7.29g,
10mmol), the 2.5M carbon of receptor unit D:4- (diphenyl amino)-phenyl boric acid (3.18g, 33mmol), 30mL toluene and 10mL
Sour aqueous solutions of potassium is added in the schlenk bottle of 100mL, is carried out substituting gas with argon gas.
Step S2, then to addition four triphenyl phosphorus palladium (0.48g, 0.4mmol) of catalyst in schlenk bottle described,
Back flow reaction is for 24 hours under 80 DEG C of reaction temperature；
Step S3, it is cooled to room temperature after the reaction was completed, extraction three is carried out with DCM to the reaction solution in schlenk bottles described
Secondary, washing three times, is then used for anhydrous sodium sulfate drying, filters and be spin-dried for, obtain surplus materials.
Step S4, column chromatography is carried out with the silica gel of 200~300 mesh to the surplus materials, the leacheate being directed to is
Petroleum ether: DCM (1:1, V/V) obtains red solid 10.68g, yield 92%.HRMS[M+H]+calcd.for
C78H51N3O6S3:1221.2940；found:1221.2952.
Further, the target compound 1 is tested, wherein
1, the photophysical property of 1 molecule of target compound:
Refering to Figure 1, which illustrates the fluorescence emission spectras of the target compound 1.
2, the optical physics data of target molecule:
The 1 minimum singlet state (S1) of target compound and lowest triplet state energy level (T1) and its energy level difference and PLQY
Data, shown in table specific as follows:
| PL Peak(nm) | S1(eV) | T1(eV) | ΔEST(eV) | PLQY (%) | |
| Target compound 1 | 636 | 2.25 | 2.16 | 0.09 | 94 |
Further, it is a further aspect of the present invention to provide a kind of thermal activation delayed fluorescence chemical combination of the present invention
The application of object, for for the luminescent layer in the electroluminescent device in OLED display panel.
It please refers to shown in Fig. 2, wherein the electroluminescent device includes substrate layer 1, implanted layer 2, hole transmission layer 3, hair
Photosphere 4, electron transfer layer 5 and cathode layer 6.
Specifically, wherein the substrate layer 1 is glass and electro-conductive glass (ITO) layer；The material that the implanted layer 2 uses
For six cyano -1,4,5,8,9,12- of 2,3,6,7,10,11-, six azepine benzophenanthrene (HATCN)；What the hole transmission layer used
Material is 4,4'- cyclohexyl two [N, N- bis- (4- aminomethyl phenyl) aniline] (TAPC)；The material that the luminescent layer 4 uses is this hair
The bright thermal activation delay compound and another 4,4 '-N of material of main part being related to ,-two carbazole biphenyl of N ' (CBP)；The electronics
The material that transport layer 5 uses is 1,3,5- tri- (3- (3- pyridyl group) phenyl) benzene (Tm3PyPB)；And the cathode layer 6 uses
Material be lithium fluoride/aluminium.
Further, wherein the specific preparation method of the electroluminescent device can be with are as follows: in the conductive glass through over cleaning
On glass (ITO) substrate 1 in high vacuum conditions, the implanted layer (HATCN) is successively deposited, hole transmission layer (TAPC), shines
Layer, electron transfer layer (TmPyPB), 1nm LiF and 100nm Al.Following (the wherein institute of the present invention of structure after the completion
Emitting layer material is stated by taking the target compound 1 as an example):
ITO/HATCN (30nm)/TAPC (40nm)/CBP:5% target compound 1 (40nm)/TmPyPB (40nm)/LiF
(1nm)/Al(100nm)
Further, relevant current versus brightness-voltage characteristic is carried out to the target devices to test, be specially to use
With corrected silicon photoelectric diode the source Keithley measuring system (2400 Sourcemeter of Keithley,
Keithley 2000Currentmeter) it carries out, electroluminescent spectrum is surveyed by French JY company SPEX CCD3000 spectrometer
Amount obtains, and all measurements are completed in atmosphere at room temperature.
The performance data of the target devices see the table below:
| Device | Maximum brightness (cd/m2) | EL peak(nm) | Maximum external quantum efficiency (%) |
| Target devices | 6395 | 642 | 24 |
A kind of thermal activation delayed fluorescence compound of the present invention, uses cleverly Molecular Design, synthesis
A series of long wavelength's thermal activation delayed fluorescence molecule of the benzothiophene of dioxo containing trimerization receptoroids.
Due to containing sulfuryl structure in the receptor unit molecular structure in this kind of molecule, while there is super plane configuration,
So that the complex molecule has high intersystem crossing rate constant and anti-intersystem crossing rate constant, and then can effectively press down
The reduction for making the radiation transistion rate as caused by energy gap rule, to obtain high PLQY.
Further, since super plane shows biggish rigidity again, to effectively increase the steady of the compound
It is qualitative, and then the service life of its applied electroluminescent device can be effectively improved.
Technical scope of the invention is not limited solely to the content in above description, and those skilled in the art can not take off
Under the premise of from technical thought of the invention, many variations and modifications are carried out to above-described embodiment, and these deformations and modification should all
When within the scope of the present invention.
Claims (10)
1. a kind of thermal activation delayed fluorescence compound, including donor monomer D and receptor unit A；It is characterized in that, its knot for using
Structure general formula are as follows: Dn- A, wherein n=1 or 2 or 3；
It wherein include diphenylamino molecular structure in the molecular structure of the donor monomer D, and the molecule knot of the receptor unit A
It include trimerization dioxo benzothiophene kind molecular structure in structure.
2. thermal activation delayed fluorescence compound according to claim 1；It is characterized in that, wherein the donor monomer D is adopted
General formula of molecular structure is one of following formula or following formula derivative:
3. thermal activation delayed fluorescence compound according to claim 1；It is characterized in that, wherein the receptor unit A is adopted
General formula of molecular structure is one of following formula or following formula derivative:
4. a kind of preparation method for preparing thermal activation delayed fluorescence compound according to claim 1；It is characterized in that, packet
Include following steps:
It step S1, will be using the donor monomer material for including diphenylamino molecular structure and including trimerization dioxo benzothiophene kind
The receptor unit material of molecular structure, which is dissolved in solvent, forms mixed solution；
Step S2, the described mixed solution carries out 20~30h of back flow reaction in 70~95 DEG C of temperature ranges；
Step S3, it is cooled to 15~40 DEG C of temperature ranges after reaction, the reaction solution is extracted, is washed, is dried, mistake
It filters and is spin-dried for processing and obtain surplus materials；And
Step S4, column chromatography is carried out using the silica gel of 200-300 mesh to the surplus materials, and then obtains institute of the present invention
State thermal activation delayed fluorescence compound.
5. a kind of preparation method of thermal activation delayed fluorescence compound according to claim 4；It is characterized in that, wherein existing
It further include being carried out substituting gas disposal with argon gas to the mixed solution in the step S1；Wherein the solvent include toluene and
Wet chemical.
6. a kind of preparation method of thermal activation delayed fluorescence compound according to claim 4；It is characterized in that, wherein existing
In the step S2, being added in the mixed solution has four triphenyl phosphorus palladium of catalyst.
7. a kind of preparation method of thermal activation delayed fluorescence compound according to claim 4；It is characterized in that, wherein existing
In the step S3, the extractant that the extraction processing uses includes DCM.
8. a kind of preparation method of thermal activation delayed fluorescence compound according to claim 4；It is characterized in that, wherein existing
In the step S4, leacheate used in the column Image processing includes petroleum ether and the mixed liquor of DCM.
9. a kind of preparation method of thermal activation delayed fluorescence compound according to claim 8；It is characterized in that, wherein existing
In the step S4, the volume ratio both in the petroleum ether and DCM mixed liquor is (0.8~1.5): 1.
10. a kind of electroluminescent device, substrate layer, hole transmission layer, implanted layer, luminescent layer, electronics including setting gradually are passed
Defeated layer and cathode layer；It is characterized in that, the material that wherein luminescent layer uses includes that heat according to claim 1 is living
Change delayed fluorescence compound.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021088243A1 (en) * | 2019-11-06 | 2021-05-14 | 武汉华星光电半导体显示技术有限公司 | Thermally activated delayed fluorescent material and preparation method therefor |
| CN113402524A (en) * | 2021-07-26 | 2021-09-17 | 中国科学院宁波材料技术与工程研究所 | Thermal activation delayed fluorescence micromolecule material, organic electroluminescent device and manufacturing method |
| WO2021189528A1 (en) * | 2020-03-23 | 2021-09-30 | 武汉华星光电半导体显示技术有限公司 | Thermally activated delayed fluorescent material and synthesis method therefor, and electroluminescent device |
| WO2022230574A1 (en) * | 2021-04-26 | 2022-11-03 | 株式会社Kyulux | Charge transport material, composition, and organic luminescent element |
-
2019
- 2019-06-04 CN CN201910481789.XA patent/CN110128443A/en not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021088243A1 (en) * | 2019-11-06 | 2021-05-14 | 武汉华星光电半导体显示技术有限公司 | Thermally activated delayed fluorescent material and preparation method therefor |
| US11444253B2 (en) | 2019-11-06 | 2022-09-13 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Thermally activated delayed fluorescent material and preparation method thereof |
| WO2021189528A1 (en) * | 2020-03-23 | 2021-09-30 | 武汉华星光电半导体显示技术有限公司 | Thermally activated delayed fluorescent material and synthesis method therefor, and electroluminescent device |
| WO2022230574A1 (en) * | 2021-04-26 | 2022-11-03 | 株式会社Kyulux | Charge transport material, composition, and organic luminescent element |
| CN113402524A (en) * | 2021-07-26 | 2021-09-17 | 中国科学院宁波材料技术与工程研究所 | Thermal activation delayed fluorescence micromolecule material, organic electroluminescent device and manufacturing method |
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