CN108191867A - A kind of thermal activation delayed fluorescence material and its application - Google Patents
A kind of thermal activation delayed fluorescence material and its application Download PDFInfo
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- 0 CCCC1(CC1)c(c(CC)c1)cc(*(c2c(*3C4=C(C56C(C=C(*I=C)C(N*)=C(*)C7)=C7C(C(*)=NCC=CC)=C5C=C(C)C)C=C(*)C5[C@@]4(C)C5*)c6ccc2)C2=C3C=CC)c1C(C=C(C)CC(C)=S)=C(C(C)*C)[C@@]1C(*)=C(C)C(C)C(C)=CC1*C2=C Chemical compound CCCC1(CC1)c(c(CC)c1)cc(*(c2c(*3C4=C(C56C(C=C(*I=C)C(N*)=C(*)C7)=C7C(C(*)=NCC=CC)=C5C=C(C)C)C=C(*)C5[C@@]4(C)C5*)c6ccc2)C2=C3C=CC)c1C(C=C(C)CC(C)=S)=C(C(C)*C)[C@@]1C(*)=C(C)C(C)C(C)=CC1*C2=C 0.000 description 6
- PGHPVJDKKJBVGZ-UHFFFAOYSA-N CNc1cc(N2C(C(C34c(cccc5)c5-c5c3cccc5)=CCC3)=C3N3c5c2cccc5C(CCC=C2)=C2C(C=CCC2)=C2C2C=CC(C#N)=CC32)c4cc1 Chemical compound CNc1cc(N2C(C(C34c(cccc5)c5-c5c3cccc5)=CCC3)=C3N3c5c2cccc5C(CCC=C2)=C2C(C=CCC2)=C2C2C=CC(C#N)=CC32)c4cc1 PGHPVJDKKJBVGZ-UHFFFAOYSA-N 0.000 description 1
- RHGZZGHQHMVHMC-UHFFFAOYSA-N Cc(cc12)ccc1-c1ccc(C)cc1C21c(cccc2N3c4cc(C#N)ccc4C4(c5cc(C)ccc5-c5c4cc(C)cc5)c4c3cccc4)c2Nc2cc(C#N)ccc12 Chemical compound Cc(cc12)ccc1-c1ccc(C)cc1C21c(cccc2N3c4cc(C#N)ccc4C4(c5cc(C)ccc5-c5c4cc(C)cc5)c4c3cccc4)c2Nc2cc(C#N)ccc12 RHGZZGHQHMVHMC-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a kind of thermal activation delayed fluorescence material and its applications, belong to organic photoelectrical material technical field.The thermal activation delayed fluorescence material has the structure as shown in formula I：Wherein, R1、R2、R3、R4、R5One kind in H atom, methyl, cyano, and R are represented each independently1、R2、R3、R4、R5In at least one represent cyano.The invention also discloses the applications of above-mentioned thermal activation delayed fluorescence material.The material of the present invention has D A types molecular structures and very small Δ Est, it can be achieved that thermal activation delayed fluorescence shines, can be applied in field of organic electroluminescence as the luminescent layer of small molecule organic electroluminescence device.
Description
Technical field
The present invention relates to a kind of thermal activation delayed fluorescence material and its applications, belong to organic photoelectrical material technical field.
Background technology
Organic electroluminescent diode (OLED) results from the eighties in last century, it has self-luminous, wide viewing angle, corresponding speed
Degree is fast, colour gamut is broad, many advantages, such as Flexible Displays can be achieved, and by the continuous development of 30 years, which gradually moved towards
Maturation, at present, organic electroluminescent technology has been widely used in many commodity such as smart mobile phone, flat panel TV, virtual reality
In.
Organic electroluminescence device is a kind of luminescent device of electric current driving, according to the difference of luminous mechanism, can be divided into
Two kinds of fluorescent device and phosphorescent devices, when charge is from electrode injection device, due to the randomness in electron spin direction, singlet state
The ratio of exciton only has 25%, and in addition 75% is triplet exciton, and under normal circumstances, fluorescent device can only utilize singlet excited
Excitonic luminescence, and phosphorescent devices can be simultaneously using singlet excitons and the energy of triplet exciton, therefore, the effect of phosphorescent devices
Rate is much larger than fluorescent device.
The efficiency of phosphorescent devices is higher than fluorescent device, and but, phosphorescent devices also have its shortcoming, as phosphor material is main
It is the complex of the complex containing noble metal, particularly metal iridium and platinum, since metal iridium and platinum itself are expensive, because
This, the price of phosphor material is extremely expensive, and which also limits the application spaces of phosphor material.
Therefore, exploitation uses fluorescent material as light emitting molecule, and can realize the OLED device of High Efficiency Luminescence, such
Research direction seems very attractive.
2012, C.Adachi published thesis (Nature., 2012,492,234) on Nature, reports one for the first time
Kind realizes the fluorescent device of High Efficiency Luminescence, since such material can be sharp simultaneously based on thermal activation delayed fluorescence (TADF) mechanism
It is shone with the energy of singlet excitons and triplet exciton, therefore its device efficiency shines far above traditional fluorescent material
Efficiency, it is suitable with phosphor material in theory, therefore, the exploitation of novel TADF materials, for the making of high efficiency fluorescent device, band
Direction newly is come.
In order to realize that TADF shines, organic material needs have minimum triplet excited state-singlet excited energy level difference (Δ
Est), it can ensure that, in excitation, triplet exciton can carry out anti-intersystem crossing in this way, postpone so as to fulfill thermal activation
Fluorescence radiation.On molecular structure, TADF materials are usually needed with electron donor structural unit (abbreviation D) and electron acceptor knot
Structure unit (abbreviation A), the D-A type molecular structure thus formed are advantageously implemented thermal activation delayed fluorescence and shine.
Invention content
An object of the present invention is to provide a kind of thermal activation delayed fluorescence material.The material of the present invention is with D-A type point
Minor structure and very small Δ Est, it can be achieved that thermal activation delayed fluorescence shines, small molecule organic electroluminescence device can be used as
Luminescent layer, apply in field of organic electroluminescence.
The scheme that the present invention solves above-mentioned technical problem is as follows：A kind of thermal activation delayed fluorescence material has as shown in formula I
Structure：
Wherein, R1、R2、R3、R4、R5One kind in H atom, methyl and cyano, and R are represented each independently1、R2、R3、R4、
R5In at least one represent cyano.
Based on the above technical solution, the present invention can also be improved as follows.
Further, the concrete structure formula of the thermal activation delayed fluorescence material is：
Any one of.
The second object of the present invention is to provide the application of above-mentioned thermal activation delayed fluorescence material.The thermal activation of the present invention is prolonged
Slow fluorescent material can be used for preparing organic electroluminescence device, illustrate preferable efficiency, the maximum brightness 6500- of device
7750cd/m2, maximum current efficiency 22.6-25.9cd/A, device efficiency is excellent.
The technical solution that the present invention solves above-mentioned technical problem is as follows：A kind of above-mentioned thermal activation delayed fluorescence material is used to make
Have organic electroluminescence devices.
The third object of the present invention is to provide a kind of organic electroluminescence device.Compared with contrast material DCTP, with this hair
The organic electroluminescence device that the bright material makes, device efficiency promote 3-4 times, significance difference of the two in device performance
Different, also further confirmation, material of the present invention have a clear superiority on luminous mechanism.
The technical solution that the present invention solves above-mentioned technical problem is as follows：A kind of organic electroluminescence device, at least one layer of work(
Ergosphere contains above-mentioned thermal activation delayed fluorescence material.
Based on the above technical solution, the present invention can also be improved as follows.
Further, the functional layer is luminescent layer.
The specific synthesis side that the present invention in embodiment later, will provide thermal activation delayed fluorescence material of the present invention
Method, meanwhile, the present invention will also provide application example of the above-mentioned material for the functional layer of organic electroluminescence device, prepared
Organic electroluminescence device generally comprises the ITO Conducting Glass (anode) being sequentially overlapped, hole injection layer (HAT-CN), sky
Cave transport layer (TAPC), luminescent layer (mCP adulterates material of the present invention), electron transfer layer (TpPyPB), electron injecting layer
(LiF) and cathode layer (Al).All functional layers are made of vacuum evaporation process, some used are organic in such device
The molecular structural formula of compound is as follows：
In the present invention, the functional layer structure of OLED device, it is not limited to above-mentioned functional layer structure, the function of OLED device
Layer material is also not limited to using above-mentioned material, these materials can be replaced with other materials, to device to be further improved
Part performance.
It should be appreciated that implementation process of the present invention with as a result, be intended merely to preferably explain the present invention, be not to this
The limitation of invention.
The beneficial effects of the invention are as follows：
1. the present invention provides a kind of new small molecule electroluminescent organic material with Shuan Luo carbon center, such material
With larger steric hindrance and excellent thin film stability, in addition, the molecular mass 750-820 of such material, it is appropriate to have
Molecular mass and excellent thermal stability, be suitble to the vapor deposition processing procedure of small molecule organic electroluminescence device.
2. the material of the present invention has cyano benzene, cyano fluorenes and triaromatic amine structural unit simultaneously, wherein, cyano benzene, cyanogen
Base fluorene structural units have drawing electro, and triaromatic amine structural unit has electron donating property, thus constitutes D-A type molecule knot
Structure, this structure feature cause target molecule to have very small triplet excited state-singlet excited energy level difference (Δ Est), have
Conducive to realizing in excitation, the anti-intersystem crossing of triplet exciton is real so as to be effectively utilized the energy of triplet exciton
Show thermal activation delayed fluorescence to shine, obtain very high device efficiency.
3. the organic electroluminescence device made using material of the present invention as the luminescent layer of organic electroluminescence device,
Illustrate preferable efficiency, the maximum brightness 6500-7750cd/m of device2, maximum current efficiency 22.6-25.9cd/A, device
Good efficiency.
4. due to material according to the present invention, there is thermal activation delayed fluorescence luminosity, triplet can be efficiently used
Excitonic luminescence, therefore, compared with contrast material DCTP, with the organic electroluminescence device that material of the present invention makes, device
3-4 times of improved efficiency, significant difference of the two in device performance, also further confirmation, material of the present invention are shining
It has a clear superiority in mechanism.
Description of the drawings
Fig. 1 is the structure diagram of the organic electroluminescence device made by the present invention, by lower floor to upper strata, is followed successively by
ITO Conducting Glass (101), hole injection layer (102), hole transmission layer (103), luminescent layer (104), electron transfer layer
(105), electron injecting layer (106) and cathode layer (107), wherein luminescent layer (104) be related to it is of the present invention and thermal activation
Delayed fluorescence material.
Specific embodiment
The principle of the present invention and feature are described below in conjunction with specific attached drawing, example is served only for explaining this hair
It is bright, it is not intended to limit the scope of the present invention.
Compound prepares embodiment：
Embodiment 1：The preparation of compound C01
The preparation of compound S2：In 500mL there-necked flasks, compound S1 (19.7g, 0.04mol), tetrahydrofuran are added in
(210g), is cooled to -78 DEG C, the hexane solution (2.2mol/L, 36.5mL, 0.08mol) of n-BuLi is added dropwise, 1h is dripped
Finish, -78 DEG C of heat preservation 1.5h, by solid 2,7- dichloros Fluorenone (20.0g, 0.08mol) is added portionwise in reaction bulb, -78 DEG C of heat preservations
3h is reacted, reaction bulb is moved into ice-water bath, warms naturally to -5 DEG C, the dilute hydrochloric acid that 80g mass concentrations 5% are added dropwise is quenched instead
Should, 0.5h is stirred, organic phase is collected in liquid separation, and removed under reduced pressure solvent obtains S2 crude product 36.2g, and gained crude product no longer carries out
It is refined, it direct plunges into reacting in next step.
The preparation of compound S3：In 500mL there-necked flasks, compound S2 crude product 36.2g prepared by previous step are added in, are added in
Glacial acetic acid 190g, the concentrated hydrochloric acid 0.5g of mass concentration 37%, is warming up to 100 DEG C, is stirred to react 3h, is naturally cooling to 40 DEG C, has
A large amount of solids are precipitated, and filter, and gained crude product is collected in absolute ethyl alcohol 300g elution, cross silica gel column chromatography refinement, eluant, eluent for just oneself
Alkane：Dichloromethane=1:1 (v/v) further uses toluene as solvent recrystallization, obtains object S3 fine work 9.2g, yield
28.8%, high resolution mass spectrum, positive ion mode, molecular formula C50H26Cl4N2, theoretical value 796.0821, test value 796.0827.
The preparation of compound C01：In 500mL autoclaves, compound S2 (9.15g, 11.5mmol), Isosorbide-5-Nitrae-dioxy are added in
Six ring 100mL, deionized water 100mL, K4[Fe(CN)6] (29.5g, 80mmol), potassium carbonate (11.0g, 80mmol), bis- rings of 2-
Hexyl phosphino- -2,6- diisopropyl -4- sulfonate radical -1,1- biphenyl sodium salt hydrates (1.1g, 2mmol), palladium (0.22g,
1mmol), 125 DEG C, insulation reaction 16h are warming up to, is cooled to 25 DEG C, filtering, gained crude product crosses silica gel column chromatography refinement, elutes
Agent is n-hexane：Dichloromethane=1:1 (v/v), gained object C01 crude products are further distilled using chemical gas-phase deposition system
Purification, 355 DEG C of sublimation temperature obtain 2.61g object C01 fine work, yield 30%, high resolution mass spectrum, positive ion mode, molecule
Formula C54H26N6, theoretical value 758.2219, test value 758.2211, elemental analysis (C54H26N6), theoretical value C：85.47 H：
3.45 N：11.08 measured value C：85.42 H：3.51 N：11.07.
Embodiment 2：The preparation of compound C03
Using S4 as raw material, with reference to 1 the method for embodiment, prepare compound C03 obtains object 1.7g, high-resolution matter
Spectrum, positive ion mode, molecular formula C56H30N6, theoretical value 786.2532, test value 786.2538, elemental analysis (C56H30N6), reason
By value C：85.48 H：3.84 N：10.68 measured value C：85.43 H：3.92 N：10.65.
Embodiment 3：The preparation of compound C04
Using S5 as raw material, with reference to 1 the method for embodiment, prepare compound C04 obtains object 1.9g, high-resolution matter
Spectrum, positive ion mode, molecular formula C58H34N6, theoretical value 814.2845, test value 814.2841, elemental analysis (C58H34N6), reason
By value C：85.48 H：4.21 N：10.31 measured value C：85.41 H：4.24 N：10.35.
Embodiment 4：The preparation of compound C05
With 3,6- dichloros Fluorenone for raw material, with reference to 1 the method for embodiment, prepare compound C05 obtains object
2.3g, high resolution mass spectrum, positive ion mode, molecular formula C54H26N6, theoretical value 758.2219, test value 758.2213, element point
Analyse (C54H26N6), theoretical value C：85.47 H：3.45 N：11.08 measured value C：85.45 H：3.54 N：11.01.
Embodiment 5：The preparation of compound C07
With S6 and 3,6- dichloros Fluorenone is raw material, and with reference to 1 the method for embodiment, prepare compound C07 obtains object
1.8g, high resolution mass spectrum, positive ion mode, molecular formula C56H30N6, theoretical value 786.2532, test value 786.2529, element point
Analyse (C56H30N6), theoretical value C：85.48 H：3.84 N：10.68 measured value C：85.47 H：3.91 N：10.62.
Embodiment 6：The preparation of compound C09
With 4,5- dichloros Fluorenone for raw material, with reference to 1 the method for embodiment, prepare compound C09 obtains object
1.6g, high resolution mass spectrum, positive ion mode, molecular formula C54H26N6, theoretical value 758.2219, test value 758.2210, element point
Analyse (C54H26N6), theoretical value C：85.47 H：3.45 N：11.08 measured value C：85.49 H：3.49 N：11.02.
Embodiment 7：The preparation of compound C13
Using S7 and 9-Fluorenone as raw material, with reference to 1 the method for embodiment, prepare compound C13 obtains object 1.8g,
High resolution mass spectrum, positive ion mode, molecular formula C52H28N4, theoretical value 708.2314, test value 708.2318, elemental analysis
(C52H28N4), theoretical value C：88.11 H：3.98 N：7.90, measured value C：88.09 H：4.00 N：7.91.
Embodiment 8：The preparation of compound C14
With S8 and 2,7- dimethyl -9-Fluorenone is raw material, and with reference to 1 the method for embodiment, prepare compound C14 is obtained
Object 1.8g, high resolution mass spectrum, positive ion mode, molecular formula C56H36N4, theoretical value 764.2940, test value 764.2937,
Elemental analysis (C56H36N4), theoretical value C：87.93 H：4.74 N：7.32, measured value C：88.01 H：4.68 N：7.31.
Embodiment 9：The preparation of compound C15
Using S9 and 9-Fluorenone as raw material, with reference to 1 the method for embodiment, prepare compound C15 obtains object 1.7g,
High resolution mass spectrum, positive ion mode, molecular formula C52H28N4, theoretical value 708.2314, test value 708.2319, elemental analysis
(C52H28N4), theoretical value C：88.11 H：3.98 N：7.90, measured value C：88.07 H：3.99 N：7.94.
Embodiment 10：The preparation of compound C17
With S8 and 2, bis- chloro- 9-Fluorenones of 7- are raw material, and with reference to 1 the method for embodiment, prepare compound C17 obtains mesh
Mark object 0.8g, high resolution mass spectrum, positive ion mode, molecular formula C56H24N8, theoretical value 808.2124, test value 808.2129, member
Element analysis (C56H24N4), theoretical value C：83.16 H：2.99 N：13.85 measured value C：83.13 H：3.00 N：13.87.
Embodiment 11：The preparation of compound C19
Using S10 and 9-Fluorenone as raw material, with reference to 1 the method for embodiment, prepare compound C19 obtains object 1.1g,
High resolution mass spectrum, positive ion mode, molecular formula C54H26N6, theoretical value 758.2219, test value 758.2211, elemental analysis
(C54H26N6), theoretical value C：85.47 H：3.45 N：11.08 measured value C：85.51 H：3.46 N：11.03.
Organic electroluminescence device embodiment：
The present invention chooses the compound C01 of above-described embodiment preparation, compound C04, compound C05, compound C13, changes
Object C19 is closed as emitting layer material, making organic electroluminescence device, device architecture as shown in Figure 1, meanwhile, known to selection
Material DCTP makes comparative example as control material, and DCTP structural formulas see below literary comparative example 1, it should be understood that device implementation process
With as a result, being intended merely to preferably explain the present invention, not limitation of the present invention.
Embodiment 12：Applications of the compound C01 in organic electroluminescence device
The present embodiment prepares organic electroluminescence device one as shown in Figure 1 by the following method：
A) ITO (tin indium oxide) glass is cleaned：Respectively each 30 points of ito glass is cleaned with deionized water, acetone, EtOH Sonicate
Then clock handles 5 minutes in plasma cleaner, obtains ITO Conducting Glass 101；
B) the vacuum evaporation hole injection layer HAT-CN in ITO Conducting Glass 101, thickness 10nm obtain hole
Implanted layer 102；
C) on hole injection layer 102, vacuum evaporation hole transmission layer TAPC, thickness 30nm obtain hole transport
Layer 103；
D) on hole transmission layer 103, vacuum mixing vapor deposition emitting layer material CBP and compound C01, wherein CBP with
The mass ratio of compound C01 is 95:5, thickness 30nm obtain luminescent layer 104；
E) on luminescent layer 104, vacuum evaporation electron transfer layer TpPYPB, thickness 50nm obtain electron transfer layer
105；
F) on electron transfer layer 105, vacuum evaporation electron injecting layer LiF, thickness 1nm obtain electron injecting layer
106；
G) on electron injecting layer 106, vacuum evaporation cathode Al, thickness 100nm obtain cathode layer 107.
The structure of device one is ITO/HAT-CN (10nm)/TAPC (30nm)/CBP+ compounds C01 (mass ratioes 95:5,
30nm)/TpPYPB (50nm)/LiF (1nm)/Al (100nm), during vacuum evaporation, pressure<1.0×10-3Pa, device one
The photooptical datas such as bright voltage, maximum brightness, maximum current efficiency, luminescent color are opened to be listed in table 1 hereinafter.
Embodiment 13：Applications of the compound C04 in organic electroluminescence device
Embodiment is substantially the same manner as Example 12, the difference is that replacing applying the change in example 12 with compound C04
Object C01 is closed, obtains device two, the structure of device two is ITO/HAT-CN (10nm)/TAPC (30nm)/CBP+ compound C04 (matter
Measure ratio 95:5,30nm)/TpPYPB (50nm)/LiF (1nm)/Al (100nm), during vacuum evaporation, pressure<1.0X10-3Pa,
The photooptical datas such as bright voltage, maximum brightness, maximum current efficiency, luminescent color that open of device two are listed in table 1 hereinafter.
Embodiment 14：Applications of the compound C05 in organic electroluminescence device
Embodiment is substantially the same manner as Example 12, the difference is that replacing applying the change in example 12 with compound C05
Object C01 is closed, obtains device three, the structure of device three is ITO/HAT-CN (10nm)/TAPC (30nm)/CBP+ compound C04 (matter
Measure ratio 95:5,30nm)/TpPYPB (50nm)/LiF (1nm)/Al (100nm).
Applications of the 15 compound C13 of embodiment in organic electroluminescence device
Embodiment is substantially the same manner as Example 12, the difference is that replacing applying the change in example 12 with compound C13
Object C01 is closed, obtains device four, the structure of device four is ITO/HAT-CN (10nm)/TAPC (30nm)/CBP+ compound C13 (matter
Measure ratio 95:5,30nm)/TpPYPB (50nm)/LiF (1nm)/Al (100nm).
Embodiment 16：Applications of the compound C19 in organic electroluminescence device
Embodiment is substantially the same manner as Example 12, the difference is that replacing applying the change in example 12 with compound C19
Object C01 is closed, obtains device five, the structure of device five is ITO/HAT-CN (10nm)/TAPC (30nm)/CBP+ compound C19 (matter
Measure ratio 95:5,30nm)/TpPYPB (50nm)/LiF (1nm)/Al (100nm).
Comparative example 1：Applications of the compound DCTP in organic electroluminescence device
Compound DCTP is a kind of known electroluminescent organic material, and the present invention chooses DCTP compounds as a comparison, and
Compound C01 is replaced with compound DCTP, according to 12 the method for embodiment, makes organic electroluminescence device six, device six
Structure be ITO/HAT-CN (10nm)/TAPC (30nm)/CBP+ compounds DCTP (mass ratioes 95:5,30nm)/TpPYPB
(50nm)/LiF (1nm)/Al (100nm), device one to device six open bright voltage, maximum brightness, maximum current efficiency, shine
The photooptical datas such as color are as shown in table 1 below：
1 device one of table is to six photooptical data table of device
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all the present invention spirit and
Within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention.
Claims (5)
1. a kind of thermal activation delayed fluorescence material, which is characterized in that there is the structure as shown in formula I：
Wherein, R1、R2、R3、R4、R5One kind in H atom, methyl and cyano, and R are represented each independently1、R2、R3、R4、R5In
At least one represents cyano.
A kind of 2. thermal activation delayed fluorescence material according to claim 1, which is characterized in that the thermal activation delayed fluorescence
The concrete structure formula of material is：
Any one of.
3. a kind of thermal activation delayed fluorescence material as described in claim 1 or 2 is any is used to prepare organic electroluminescence device.
4. a kind of organic electroluminescence device, which is characterized in that at least one functional layer contains any institute of claims 1 or 2
The thermal activation delayed fluorescence material stated.
5. a kind of organic electroluminescence device according to claim 4, which is characterized in that the functional layer is luminescent layer.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293661A (en) * | 2018-10-22 | 2019-02-01 | 武汉华星光电半导体显示技术有限公司 | Near infrared light hot activation delayed fluorescence material and preparation method thereof, display device |
| CN109575038A (en) * | 2017-09-28 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of compound of the fluorenes of xanthene containing spiral shell and its application on organic electroluminescence device |
| CN109575037A (en) * | 2017-09-28 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of compound of the fluorenes of dimethylanthracene containing spiral shell and its application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107098919A (en) * | 2017-03-13 | 2017-08-29 | 华南理工大学 | The molten conjugation small molecule of A D A types water/alcohol and its application in organic electronic device |
-
2017
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107098919A (en) * | 2017-03-13 | 2017-08-29 | 华南理工大学 | The molten conjugation small molecule of A D A types water/alcohol and its application in organic electronic device |
Non-Patent Citations (2)
| Title |
|---|
| MEHES G,ET AL: "Enhanced Electroluminescence Efficiency in a Spiro-Acridine Derivative through Thermally Activated Delayed Fluorescence", 《CHEM.INT.EDIT》 * |
| 张静: "HAT-CN作为空穴注入层的高效白色荧光有机电致发光二极管", 《液晶与显示》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109575038A (en) * | 2017-09-28 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of compound of the fluorenes of xanthene containing spiral shell and its application on organic electroluminescence device |
| CN109575037A (en) * | 2017-09-28 | 2019-04-05 | 江苏三月光电科技有限公司 | A kind of compound of the fluorenes of dimethylanthracene containing spiral shell and its application |
| CN109293661A (en) * | 2018-10-22 | 2019-02-01 | 武汉华星光电半导体显示技术有限公司 | Near infrared light hot activation delayed fluorescence material and preparation method thereof, display device |
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