CN108047228A - A kind of new hot activation delayed fluorescence luminescent material and its application and device - Google Patents
A kind of new hot activation delayed fluorescence luminescent material and its application and device Download PDFInfo
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- CN108047228A CN108047228A CN201711200214.3A CN201711200214A CN108047228A CN 108047228 A CN108047228 A CN 108047228A CN 201711200214 A CN201711200214 A CN 201711200214A CN 108047228 A CN108047228 A CN 108047228A
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- 0 C[n]1c2ccccc2c-2c1C*c1ccccc-21 Chemical compound C[n]1c2ccccc2c-2c1C*c1ccccc-21 0.000 description 8
- AKPREGTZVUSLLS-UHFFFAOYSA-N BrC(CC=C1C2=NC3=NC(c(ccc(Br)c4)c4Br)=NC3=N2)C=C1Br Chemical compound BrC(CC=C1C2=NC3=NC(c(ccc(Br)c4)c4Br)=NC3=N2)C=C1Br AKPREGTZVUSLLS-UHFFFAOYSA-N 0.000 description 1
- PHAOWALUGLMCBX-UHFFFAOYSA-N CC1(C)c(cc(c(CCC=C2)c2[o]2)c2c2)c2N(C)c2c1cccc2 Chemical compound CC1(C)c(cc(c(CCC=C2)c2[o]2)c2c2)c2N(C)c2c1cccc2 PHAOWALUGLMCBX-UHFFFAOYSA-N 0.000 description 1
- GDTFHYKBSJOMPL-UHFFFAOYSA-N CC1(C)c(cccc2)c2N(c(cc2)cc3c2[n](C)c2ccccc32)c2c1cccc2 Chemical compound CC1(C)c(cccc2)c2N(c(cc2)cc3c2[n](C)c2ccccc32)c2c1cccc2 GDTFHYKBSJOMPL-UHFFFAOYSA-N 0.000 description 1
- IAPVCAYMSZOIPJ-UHFFFAOYSA-N CN(C1C=CC=CC11)c(cc2)c1cc2N1c(cccc2)c2N(c2ccccc2)c2c1cccc2 Chemical compound CN(C1C=CC=CC11)c(cc2)c1cc2N1c(cccc2)c2N(c2ccccc2)c2c1cccc2 IAPVCAYMSZOIPJ-UHFFFAOYSA-N 0.000 description 1
- ZOEBDPIWXOMEHW-UHFFFAOYSA-N CN(C1C=CC=CC11)c(cccc2)c2N1c1ccccc1 Chemical compound CN(C1C=CC=CC11)c(cccc2)c2N1c1ccccc1 ZOEBDPIWXOMEHW-UHFFFAOYSA-N 0.000 description 1
- YVUJALYDFBLEOD-UHFFFAOYSA-N CN1c(cccc2)c2OC2C=CC=CC12 Chemical compound CN1c(cccc2)c2OC2C=CC=CC12 YVUJALYDFBLEOD-UHFFFAOYSA-N 0.000 description 1
- QXBUYALKJGBACG-UHFFFAOYSA-N CN1c(cccc2)c2Sc2c1cccc2 Chemical compound CN1c(cccc2)c2Sc2c1cccc2 QXBUYALKJGBACG-UHFFFAOYSA-N 0.000 description 1
- XXQOYGJLMWPAKC-UHFFFAOYSA-N C[n]1c(C=CC(C2)N(C3C=CC=CC3C3)C4=C3C=CCC4)c2c2cc(C(C3)C4C=CC(C5)C5C4Oc4c3cccc4)ccc12 Chemical compound C[n]1c(C=CC(C2)N(C3C=CC=CC3C3)C4=C3C=CCC4)c2c2cc(C(C3)C4C=CC(C5)C5C4Oc4c3cccc4)ccc12 XXQOYGJLMWPAKC-UHFFFAOYSA-N 0.000 description 1
- UCGJIZSVLHVPJE-UHFFFAOYSA-N C[n]1c(cc2[o]c(cccc3)c3c2c2)c2c2ccccc12 Chemical compound C[n]1c(cc2[o]c(cccc3)c3c2c2)c2c2ccccc12 UCGJIZSVLHVPJE-UHFFFAOYSA-N 0.000 description 1
- GXZPCWDPYMTIMA-UHFFFAOYSA-N C[n]1c(ccc(N(c2ccccc2)c2ccccc2)c2)c2c2ccccc12 Chemical compound C[n]1c(ccc(N(c2ccccc2)c2ccccc2)c2)c2c2ccccc12 GXZPCWDPYMTIMA-UHFFFAOYSA-N 0.000 description 1
- ASTQBSGMWVCVEY-UHFFFAOYSA-N C[n]1c(ccc(N2c(cccc3)c3Sc3c2cccc3)c2)c2c2ccccc12 Chemical compound C[n]1c(ccc(N2c(cccc3)c3Sc3c2cccc3)c2)c2c2ccccc12 ASTQBSGMWVCVEY-UHFFFAOYSA-N 0.000 description 1
- SDFLTYHTFPTIGX-UHFFFAOYSA-N C[n]1c(cccc2)c2c2ccccc12 Chemical compound C[n]1c(cccc2)c2c2ccccc12 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 1
- PGSVNTIDEZRNES-UHFFFAOYSA-N O=Cc(c(Br)c1)ccc1Br Chemical compound O=Cc(c(Br)c1)ccc1Br PGSVNTIDEZRNES-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to a kind of new hot activation delayed fluorescence luminescent material and its application and device, the material is it is characterised in that it includes with formula（1）Shown structure,Wherein, R1、R2、R3、R4It is hydrogen atom, C1~C10Acyclic straight or branched paraffin, C3~C30Substituted or non-substituted carbazole group, C3~C30Substituted or non-substituted arylamine group, C3~C30Substituted or non-substituted phenthazine group, C3~C30Substituted or non-substituted phenoxazine group, C3~C30Substituted or non-substituted azophenlyene group and C3~C30Any one in substituted or non-substituted acridine group, the material character provided by the invention are stablized, and have good luminescent properties, luminescent material can be used as, applied in organic electroluminescence device.
Description
Technical field
The invention belongs to field of organic electroluminescent materials, and in particular to a kind of new hot activation delayed fluorescence luminescent material
And its application and device.
Background technology
Hot activation delayed fluorescence (TADF) is a kind of special fluorescence phenomenon, and principle of luminosity is triplet state T1 excitons in heat
Reversed intersystem crossing generation singlet S1 excitons under activation, S1 excitons radiation transistion generates fluorescence, due to the TADF of early stage
Molecular fluorescence inefficiency, therefore enough attention are not obtained, 2009, Adachi seminars of Kyushu University were for the first time
Observe TADF phenomenons in tin complex, and by unremitting effort, 2012, Adachi seminars using carbazole as donor,
Dicyanobenzenes are receptor, and design has synthesized the hair of a series of TADF molecules, wherein green light molecule 4CzIPN with different colours
Optical property is the most superior, and the external quantum efficiency of device is 19.3 ± 1.5%, and the exciton utilization rate of device has reached 100%,
Achievement in research is published in the same year nature periodical.Afterwards, it is further excellent to cause the extensive concern of researcher, Kim etc. by TADF
The device architecture of 4CzIPN is changed so that the current efficiency of device has reached 94.5cd/A, and power efficiency is 88.6 lm/W, outside
Quantum efficiency 29.6%, device efficiency have approached the best level of phosphorescent devices, are that the efficiency reported so far is highest glimmering
Optical device.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of new hot activation delayed fluorescence luminescent material and its application
And device, there is good thermodynamic stability, higher glass transition temperature applied to organic electroluminescence field luminescent material
Degree, good film forming.
The technical solution that the present invention solves above-mentioned technical problem is as follows：A kind of new hot activation delayed fluorescence organic electroluminescence hair
Luminescent material, which is characterized in that including the structure shown in formula (1),
Wherein, R1、R2、R3、R4It is respectively and independently selected from hydrogen atom, C1~C10Acyclic straight or branched paraffin, C3~
C30Substitution or non-substituted carbazole group, C3~C30Substitution or non-substituted arylamine group, C3~C30Substitution is non-
Substituted phenthazine group, C3~C30Substitution or non-substituted phenoxazine group, C3~C30Substitution or non-substituted azophenlyene
Group, C3~C30Substitution or non-substituted acridine group in any one.
Based on the above technical solutions, the present invention can also be improved as follows.
R1、R2、R3、R4It is independently selected from lower structure：
The present invention provides a kind of application of new hot activation delayed fluorescence luminescent material in organic electroluminescence device.
The present invention also provides a kind of organic electroluminescence devices, prolong including at least one layer containing a kind of above-mentioned new hot activation
The functional layer of slow fluorescence luminescent material.
Further, the functional layer is luminescent layer.
Further, the new hot activation delayed fluorescence luminescent material is made luminous as green or yellow green luminescent material
Layer.
Further, the organic electroluminescence device is OLED device.
Following compounds C01-C40 is the representative structure for meeting spirit and principle of the invention, it should be understood that following chemical combination
Object structure is intended merely to more fully understand the present invention, is not limitation of the present invention.
The beneficial effects of the invention are as follows：
The present invention provides a kind of new hot activation delayed fluorescence luminescent material, which has good luminescent properties, heat
Mechanical stability, higher glass transition temperature.
The present invention also provides a kind of application of new hot activation delayed fluorescence luminescent material in field of organic electroluminescence.
The hot activation delayed fluorescence luminescent material is as green or yellow green dopant material.
Using above-mentioned material as green light dopant material for field of organic electroluminescence, in particular for organic electroluminescent
The luminescent layer of device.During specific application, the implementation process with as a result, being intended merely to preferably explain this hair
It is bright, it is not limitation of the present invention.
The present invention using above-mentioned hot activation delayed fluorescence OLED device, the electroluminescent device have open bright voltage it is low,
The advantages that luminous efficiency is high, stability is good, service life is long, so that the hot activation delayed fluorescence material has well
Industrialization prospect using material provided by the invention as functional layer, makes organic electroluminescence device.
By taking green light OLED device as an example, the ITO Conducting Glass (anode) being sequentially overlapped, hole injection layer are generally comprised
(HATCN), hole transmission layer (TAPC), luminescent layer (electroluminescent organic material of the present invention), electron transfer layer
(TmPyPB), electron injecting layer (LiF) and cathode layer (Al).All functional layers are made of vacuum evaporation process.Such device
The molecular structural formula of some used organic compounds is as follows in part.
In the present invention, the functional layer of device is not limited to using above-mentioned material, these materials can be replaced with other materials,
Can be replaced to device performance to be further improved, such as hole transmission layer with NPB, electron transfer layer can use TpPyPB,
The replacements such as TPBi, the molecular structural formula of these materials are as follows：
It should be appreciated that making the purpose of OLED device in the present invention, it is intended merely to be better described, heretofore described material
Material has good luminescent properties, and is not the limitation to material application range of the present invention.
Description of the drawings
Fig. 1 is the structure diagram of organic electroluminescence device prepared by the present invention, by lower floor to upper strata, be followed successively by 101,
ITO Conducting Glass, 102, hole injection layer, 103, hole transmission layer, 104, luminescent layer, 105, electron transfer layer, 106,
Electron injecting layer, 107, cathode layer, wherein, luminescent layer is related to electroluminescent organic material of the present invention.
Specific embodiment
The principles and features of the present invention are described below, and the given examples are served only to explain the present invention, is not intended to limit
Determine the scope of the present invention.
Embodiment 1：The preparation of intermediate M1
1,1,2,2- ethylene urotropines of 0.88g, 3.7g 4- bromobenzaldehydes, 30mL DMF are added in into 100mL autoclaves.
Closed system, oxygen pressure 1.5-2.0atm are stirred to react 1h under the conditions of 50-60 DEG C.Reaction finishes, and cooling is overnight.It will reaction
Liquid, which is poured into water, to be quenched, and pale solid is precipitated, and is filtered, and filter cake is eluted successively using absolute ethyl alcohol, n-hexane, and column chromatography carries
Pure isolated 1.20g white solids M1, yield：28.8%.
Mass spectrum MS (m/e), molecular formula C16H8Br2N4, theoretical value 413.91, test value 417.60.
Elemental analysis (C16H8Br2N4), theoretical value：C, 46.19%；H, 1.94%；Br, 38.41%；N, 13.47%；It is real
Measured value：C, 46.21%；H, 1.95%；Br, 38.39%；N, 13.45%.
Embodiment 2：The preparation of intermediate M2
Using the method similar with embodiment 1,4- bromobenzaldehydes are replaced using 3, the 5- dibromo benzaldehydes of equivalent,
His condition is constant, obtains intermediate M2, white solid 2.6g, yield 45.4%.
Mass spectrum MS (m/e), molecular formula C16H6Br4N4, theoretical value 569.73, test value 571.22.
Elemental analysis (C16H6Br4N4), theoretical value：C, 33.49%；H, 1.05%；Br, 55.70%；N, 9.76%；Actual measurement
Value：C, 33.51%；H, 1.07%；Br, 55.65%；N, 9.77%.
Embodiment 3：The preparation of intermediate M3
Using the method similar with embodiment 1,4- bromobenzaldehydes are replaced using 2, the 4- dibromo benzaldehydes of equivalent,
His condition is constant, obtains intermediate M3, white solid 1.9g, yield 33.1%.
Mass spectrum MS (m/e), molecular formula C16H6Br4N4, theoretical value 569.73, test value 571.62.
Elemental analysis (C16H6Br4N4), theoretical value C, 33.49%；H, 1.05%；Br, 55.70%；N, 9.76%；Actual measurement
Value：C, 33.48%；H, 1.04%；Br, 55.72%；N, 9.76%.
Embodiment 4：The preparation of intermediate M4
Using the method similar with embodiment 1,4- bromobenzaldehydes are replaced using 2, the 4- dibromo benzaldehydes of equivalent,
His condition is constant, obtains intermediate M4, white solid 1.7g, yield 40.8%.
Mass spectrum MS (m/e), molecular formula C16H8Br2N4, theoretical value 413.91, test value 415.00.
Elemental analysis (C16H8Br2N4), theoretical value：C, 46.19%；H, 1.94%；Br, 38.41%；N, 13.47%；It is real
Measured value：C, 46.17%；H, 1.96%；Br, 38.40%；N, 13.47%.
Embodiment 5：The preparation of intermediate M5
Using the method similar with embodiment 1,4- bromobenzaldehydes are replaced using the 2- bromobenzaldehydes of equivalent, other
Part is constant, obtains intermediate M5, white solid 1.5g, yield 36.1%.
Mass spectrum MS (m/e), molecular formula C16H8Br2N4, theoretical value 413.91, test value 414.86.
Elemental analysis (C16H8Br2N4), theoretical value：C, 46.19%；H, 1.94%；Br, 38.41%；N, 13.47%；It is real
Measured value：C, 46.18%；H, 1.95%；Br, 38.43%；N, 13.44%.
Embodiment 6：The preparation of compound C1
Under nitrogen environmental protection, successively into 100ml there-necked flasks add in M1 (2.08g, 5mmol), carbazole (2.00g,
12mmol), ortho-xylene (25mL), sodium tert-butoxide (0.96g, 10mmol), palladium (112mg, 0.5mmol), tri-tert
Phosphine tetrafluoroborate (290mg, 1.0mmol).Nitrogen strictly replaces air 3 times in system, heating reflux reaction 5-6h, TLC prison
Survey raw material is cooled to room temperature after the reaction was complete.Washing organic phase to neutrality, liquid separation, anhydrous sodium sulfate drying organic phase filters,
Filtrate desolventizing.Column chromatography purifies, and purification ＆ isolation obtains 2.60g yellow greenish powder shape solids, yield 88.4%.
Embodiment 7：The preparation of compound C2
Using the method similar with embodiment 6, M1 is replaced using the M4 of equimolar equivalent, other conditions are constant, obtain
C2, yellow greenish powder shape solid 1.80g, yield 61.2%.
Embodiment 8：The preparation of compound C3
Using the method similar with embodiment 6, M1 is replaced using the M5 of equimolar equivalent, other conditions are constant, obtain
C3, yellow powdery solid 1.20g, yield 40.8%.
Embodiment 9：The preparation of compound C4
Under nitrogen environmental protection, successively into 100ml there-necked flasks add in M1 (2.08g, 5mmol), acridine (2.50g,
12mmol), toluene (50mL), 400 mesh potassium carbonate (1.38g, 10mmol), palladium (112mg, 0.5mmol), tri-tert
Phosphine tetrafluoroborate (290mg, 1.0mmol).Nitrogen strictly replaces air 3 times in system, heating reflux reaction 3-4h, TLC prison
Survey raw material is cooled to room temperature after the reaction was complete.Washing organic phase to neutrality, liquid separation, anhydrous sodium sulfate drying organic phase filters,
Filtrate desolventizing.Column chromatography purifies, and purification ＆ isolation obtains 2.40g light yellow powder solids, yield 71.4%.
Embodiment 10：The preparation of compound C31
Under nitrogen environmental protection, successively into 100ml there-necked flasks add in M2 (1.15g, 2mmol), carbazole (1.67g,
10mmol), ortho-xylene (50mL), sodium tert-butoxide (1.15g, 12mmol), palladium (180mg, 0.8mmol), tri-tert
Phosphine tetrafluoroborate (464mg, 1.6mmol).Nitrogen strictly replaces air 3 times in system, and heating reflux reaction 16~for 24 hours,
TLC monitorings raw material is cooled to room temperature after the reaction was complete.Washing organic phase to neutrality, liquid separation, anhydrous sodium sulfate dries organic phase,
It filters, filtrate desolventizing.Column chromatography purifies, and purification ＆ isolation obtains 1.20g light yellow powder solids, yield 65.2%.
Embodiment 11：The preparation of compound C38
Under nitrogen environmental protection, successively into 100ml there-necked flasks add in M3 (1.15g, 2mmol), acridine (2.09g,
10mmol), ortho-xylene (50mL), sodium tert-butoxide (1.15g, 12mmol), palladium (180mg, 0.8mmol), tri-tert
Phosphine tetrafluoroborate (464mg, 1.6mmol).Nitrogen strictly replaces air 3 times in system, and heating reflux reaction 16~for 24 hours,
TLC monitorings raw material is cooled to room temperature after the reaction was complete.Washing organic phase to neutrality, liquid separation, anhydrous sodium sulfate dries organic phase,
It filters, filtrate desolventizing.Column chromatography purifies, and purification ＆ isolation obtains 1.60g light yellow powder solids, yield 73.7%.
Embodiment 12：The preparation of compound C40
Using the method similar with embodiment 6, carbazole is replaced using 9, the 9- diphenylacridines of equimolar equivalent, other
Condition is constant, obtains C40, light yellow powder solid 3.30g, yield 71.7%.Compound mass spectrum and elemental analysis：
Here is the Application Example of the compounds of this invention：
Embodiment 13：Device one is prepared to device seven
Preparation 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 is handled 5 minutes in plasma cleaner；
B) the vacuum evaporation hole injection layer HAT-CN on anode ito glass, thickness 10nm；
C) the vacuum evaporation hole transmission layer TAPC on hole injection layer, thickness 30nm；
D) on hole transmission layer, vacuum evaporation luminescent layer mCP:5%wt the compounds of this invention, thickness 20nm；
E) on luminescent layer, TmPyPB, thickness 30nm of the vacuum mixing vapor deposition as electron transfer layer；
F) on electron transfer layer, vacuum evaporation electron injecting layer LiF, thickness 1nm；
G) on electron injecting layer, vacuum evaporation cathode Al, thickness 100nm.
The structure of device is ITO/HAT-CN (10nm)/TAPC (30nm)/mCP:5%wt the compounds of this invention (20nm)/
TmPyPB (30nm)/LiF (1nm)/Al (100nm), during vacuum evaporation, pressure<4.0×10-4Pa, the test of obtained device
It the results are shown in Table shown in 1.
1 device photoelectric tables of data of table
As shown in table 1, the organic electroluminescence device based on hot activation delayed fluorescence material preparation of the present invention, illustrate compared with
Good luminescent properties, device open bright voltage 2.7-3.2V, high-high brightness 9842-20784cd/m2, maximum current efficiency 8.6-
18.2cd/A, maximum power efficiency 7.7-15.6 lm/W.Wherein, using compound C4 as luminescent material, device opens bright voltage and is
2.9V, high-high brightness 20784cd/m2, maximum power efficiency 15.6lm/W, maximum current efficiency 18.2cd/A are shown excellent
Device performance.
The foregoing is merely preferred embodiments of the present invention, are not limitation of the present invention.The present invention is intended to provide one
Kind hot activation delayed fluorescence electroluminescent organic material, with the electroluminescent device that material provided by the present invention makes, device
Performance has the space further promoted, such as uses other materials that TAPC is replaced to be replaced as hole transmission layer using other materials
TmPyPB makes luminescent layer etc. as electron transfer layer, using the mode of other doping, it is similar improve all it should be understood that
Belong to the protection category of the present invention.
Claims (5)
1. a kind of new hot activation delayed fluorescence electroluminescent organic material, which is characterized in that including the knot shown in formula (1)
Structure,
Wherein, R1、R2、R3、R4It is respectively and independently selected from hydrogen atom, C1~C10Acyclic straight alkane, C1~C10Aliphatic branched alkane
Hydrocarbon, C3~C30Substituted carbazole group, C3~C30Non-substituted carbazole group, C3~C30Substituted arylamine group, C3~C30It is non-
Substituted arylamine group, C3~C30Substituted phenthazine group, C3~C30Non-substituted phenthazine group, C3~C30Substituted fen
Oxazine group, C3~C30Non-substituted phenoxazine group, C3~C30Substituted azophenlyene group, C3~C30Non-substituted phenazinyl
Group, C3~C30Substituted acridine group and C3~C30Any one in non-substituted acridine group.
2. new hot activation delayed fluorescence organic electroluminescence device according to claim 1, which is characterized in that at least one layer of
Functional layer containing the new hot activation delayed fluorescence luminescent material.
3. new hot activation delayed fluorescence organic electroluminescence device according to claim 2, which is characterized in that the function
Layer is luminescent layer.
4. new hot activation delayed fluorescence organic electroluminescence device according to claim 3, which is characterized in that described to shine
Layer is made of new hot activation delayed fluorescence luminescent material as green or yellow green luminescent material.
5. new hot activation delayed fluorescence organic electroluminescence device according to claim 1, which is characterized in that described organic
Electroluminescent device is OLED device.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134520A (en) * | 2018-09-30 | 2019-01-04 | 上海天马有机发光显示技术有限公司 | A kind of hot activation delay material and the organic photoelectric device comprising it |
| 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 |
| CN109503508A (en) * | 2018-11-15 | 2019-03-22 | 武汉华星光电半导体显示技术有限公司 | Green light thermal activation delayed fluorescence material and its synthetic method, electroluminescent device |
| CN110015994A (en) * | 2019-04-29 | 2019-07-16 | 武汉华星光电半导体显示技术有限公司 | Thermal activation delayed fluorescence material and preparation method thereof, display device |
| CN110818727A (en) * | 2018-08-10 | 2020-02-21 | 上海和辉光电有限公司 | Thermal activation delayed fluorescent material, preparation method and application thereof, and OLED device comprising thermal activation delayed fluorescent material |
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2018
- 2018-03-13 CN CN201711200214.3A patent/CN108047228A/en not_active Withdrawn
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110818727A (en) * | 2018-08-10 | 2020-02-21 | 上海和辉光电有限公司 | Thermal activation delayed fluorescent material, preparation method and application thereof, and OLED device comprising thermal activation delayed fluorescent material |
| CN109134520A (en) * | 2018-09-30 | 2019-01-04 | 上海天马有机发光显示技术有限公司 | A kind of hot activation delay material and the organic photoelectric device comprising it |
| CN109134520B (en) * | 2018-09-30 | 2021-08-03 | 上海天马有机发光显示技术有限公司 | Thermal activation delay material and organic photoelectric device comprising same |
| 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 |
| WO2020082600A1 (en) * | 2018-10-22 | 2020-04-30 | 武汉华星光电半导体显示技术有限公司 | Near-infrared photothermal activation delayed fluorescent material and preparation method therefor, and display device |
| CN109503508A (en) * | 2018-11-15 | 2019-03-22 | 武汉华星光电半导体显示技术有限公司 | Green light thermal activation delayed fluorescence material and its synthetic method, electroluminescent device |
| US11485905B2 (en) | 2018-11-15 | 2022-11-01 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Green light thermally activated delayed fluorescent material and synthesizing method thereof, and electroluminescent device |
| CN110015994A (en) * | 2019-04-29 | 2019-07-16 | 武汉华星光电半导体显示技术有限公司 | Thermal activation delayed fluorescence material and preparation method thereof, display device |
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