CN118546277B - A flexible cyclic thermally activated delayed fluorescent polymer - Google Patents
A flexible cyclic thermally activated delayed fluorescent polymer Download PDFInfo
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- CN118546277B CN118546277B CN202410517230.9A CN202410517230A CN118546277B CN 118546277 B CN118546277 B CN 118546277B CN 202410517230 A CN202410517230 A CN 202410517230A CN 118546277 B CN118546277 B CN 118546277B
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- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 21
- 230000003111 delayed effect Effects 0.000 title claims abstract description 15
- 229920001109 fluorescent polymer Polymers 0.000 title abstract description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 31
- 239000000463 material Substances 0.000 claims abstract description 21
- 238000010030 laminating Methods 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 239000011521 glass Substances 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 230000000903 blocking effect Effects 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 239000002019 doping agent Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 229920005565 cyclic polymer Polymers 0.000 abstract description 4
- 229910000510 noble metal Inorganic materials 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 238000005401 electroluminescence Methods 0.000 abstract 1
- 238000005538 encapsulation Methods 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 230000004001 molecular interaction Effects 0.000 abstract 1
- 238000006862 quantum yield reaction Methods 0.000 abstract 1
- 238000010129 solution processing Methods 0.000 abstract 1
- 230000007704 transition Effects 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 8
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- -1 4- (oct-7-en-1-yloxy) -N-phenylaniline Chemical compound 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 241001085205 Prenanthella exigua Species 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004512 die casting Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
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- General Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a novel flexible annular heat-activated delayed fluorescent polymer, which contains annular TADF molecules, so that the material has TADF characteristics, is a novel polymer TADF material with simple synthesis process, and can be used for constructing solution processing type organic light-emitting diodes (OLED); the novel flexible cyclic polymer has the advantages that the solution processability of the polymer is improved due to the fact that the novel flexible cyclic polymer contains a large number of flexible cyclic TADF molecules, and meanwhile, radiation transition and high PLQY (fluorescence quantum yield) are not sacrificed; in addition, the molecular interactions are greatly limited due to the encapsulation of the polymer chains into space, thereby inhibiting the ACQ effect. Thus, polymers containing cyclic TADF molecules have a very high PLQY, while electroluminescent devices based on cyclic TADF polymers have a very high maximum external quantum efficiency. The invention realizes the synthesis of the whole annular polymer without using any catalyst and noble metal, has very wide application prospect in the field of organic electroluminescence, and is expected to be widely applied in the fields of display, solid-state lighting and the like.
Description
Technical Field
The invention belongs to the technical field of compounds, and particularly relates to a novel flexible annular heat-activated delayed fluorescence polymer.
Background
Organic Light Emitting Diodes (OLEDs) are important in display and lighting technologies due to their high efficiency, flexible and versatile device structure and multi-color emission. However, the Internal Quantum Efficiency (IQE) of conventional fluorescent organic light emitting diodes is only 25% due to the spin influence, whereas phosphorescent organic light emitting diodes can achieve IQE of 100% using rare noble metals such as Ir and Pt. To overcome these drawbacks, thermally Activated Delayed Fluorescence (TADF) organic light emitting diodes that do not contain noble metals are becoming next generation OLEDs. TADF organic light emitting diodes may be used in display and illumination technology as well as fluorescence microscopy and sensing applications.
The organic micromolecular TADF material has the advantages of accurate molecular structure, high purity (realized by recrystallization and vacuum sublimation), wide chemical modification application, high luminous efficiency and the like. However, the small molecule TADF film is usually prepared by thermal evaporation, and the film quality is reduced due to easy crystallization and aggregation of molecules, thereby reducing the efficiency and long-term stability of the OLED. OLEDs having solution-processed light-emitting layers are therefore of great interest in large-area displays because of their simple manufacturing processes and relatively low costs. The polymer and dendritic TADF materials are suitable for forming thin films by low cost solution processes such as spin coating, die casting or ink jet printing. However, the preparation of polymers and dendritic TADF materials remains challenging, which is also an expanding area of research. The cause of this difficulty is twofold. First, in macromolecules containing a large number of atoms, it is difficult to achieve both a small Δest and suppression of non-radiative internal switching. Second, triplet excitons generated by TADF are more readily annihilated by intermolecular and intramolecular triplet states in polymers than in small molecules. Furthermore, a common feature of TADF polymers reported to date is their low molecular weight, high polydispersity, which means that they are not well-defined materials. To address these problems, many strategies have been employed in designing TADF polymers.
One simple method of producing TADF polymers is to functionalize monomer units that already have TADF characteristics and excellent (small molecule) device properties, followed by polymerization. Using this strategy we designed and synthesized cyclic TADF molecules and side chain polymerized cyclic TADF as pendant units. Cyclic TADF has proven to be effective for achieving organic light emitting diodes, but its design concept is still limited to rigid pi-conjugated structures, which may limit the potential advantages of such cyclic molecular configurations in the construction of future multifunctional emitters. The constructed flexible cyclic TADF with alkyl chains as the linking agent of the present invention shows that flexible linkages significantly improve solution processibility without sacrificing radiation conversion and high PLQY through detailed photophysical analysis. Meanwhile, interaction among TADF luminous units is inhibited to a certain extent due to a chain space block, so that an efficient flexible OLED device can be prepared.
Disclosure of Invention
The invention aims to design a novel flexible annular heat-activated delayed fluorescence polymer.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
A novel flexible cyclic heat activated delayed fluorescence polymer characterized by: after the fluorenyl groups and TADF molecules form a ring, the vinyl groups are subjected to self-polymerization or copolymerization to form a polymer with a side chain containing a cyclic TADF, and the structural general formula is as follows:
wherein n is a degree of polymerization, which is an integer of 10 to 10000, Is a different group comprising triazine, carbazole, aniline, bisphenol fluorene and derivatives thereof,Is an alkyl chain.
Further, the saidThe independent structure of (2) is:
wherein n is an integer greater than 1;
The said The independent structure of (2) is:
The said process The independent structure of (2) is:
The application of the novel flexible cyclic heat-activated delayed fluorescence polymer is characterized in that: the compound is applied to the cyclic heat-activated delayed fluorescence polymer luminescent material.
The utility model provides an electroluminescent device, includes glass, adheres to the electrically conductive glass substrate layer on glass, with the hole injection layer of electrically conductive glass substrate layer laminating, with the hole transport layer of hole injection layer laminating, with the luminescent layer of hole transport layer laminating, with the hole blocking layer of luminescent layer laminating, with the electron transport layer of hole blocking layer laminating, with the cathode layer of electron transport layer laminating, its characterized in that: the light-emitting layer contains the compound according to claim 1.
Further, the light-emitting layer is composed of a host material and a dopant material as a guest, and the guest material of the light-emitting layer is the compound according to claim 1.
The technical scheme can obtain the following beneficial effects:
The invention has very simple whole synthesis process through nucleophilic substitution and vinyl self-polymerization, avoids using noble metal catalyst and reduces production cost. Since 75% of triplet excitons can be up-converted to singlet states by reverse intersystem crossing, TADF devices can theoretically achieve 100% IQE. The cyclic polymer has higher thermal decomposition temperature and glass transition temperature, and is beneficial to the preparation and daily use of devices. The TADF material is a polymer, has large molecular weight and a large number of flexible alkyl chains, has good solubility in common solvents, can be prepared into a solution-processable organic electroluminescent material by a wet method, and is beneficial to large-area preparation of devices.
Drawings
Fig. 1 is a graph of light transmittance.
Fig. 2 is an intensity wavelength plot.
Detailed Description
The invention is further described with reference to the accompanying drawings:
As shown in fig. 1-2, a novel flexible cyclic heat-activated delayed fluorescence polymer is characterized in that: after the fluorenyl groups and TADF molecules form a ring, the vinyl groups are subjected to self-polymerization or copolymerization to form a polymer with a side chain containing a cyclic TADF, and the structural general formula is as follows:
wherein n is a degree of polymerization, which is an integer of 10 to 10000, Is a different group comprising triazine, carbazole, aniline, bisphenol fluorene and derivatives thereof,Is an alkyl chain.
Further, the saidThe independent structure of (2) is:
wherein n is an integer greater than 1;
The said The independent structure of (2) is:
The said process The independent structure of (2) is:
The block-packaged delayed fluorescence macromolecular material has the advantages of low cost, environmental friendliness, high device efficiency, simplicity in synthesis, easiness in device preparation by a wet method and the like, and is a TADF material for preparing OLED devices by the wet method with great development prospect in the future.
The thermally activated delayed fluorescence polymer material C1 is a compound having the following structure:
example synthesis of polymer C1:
4- (oct-7-en-1-yloxy) -N-phenylaniline and 2,4, 6-trifluoro-1, 3, 5-triazine were dissolved with Cs 2CO3 in DMSO in an N 2 atmosphere and reacted at 130 ℃ for 24h. After cooling to room temperature, the mixture was added dropwise to saturated NaCl ice water, suction filtration was performed, and then a solid was obtained by column chromatography. Subsequently, it was dried in a vacuum oven to obtain Ar 1 as a bright white solid powder.
9,9' -Spirodi [ fluorene ] -2, 7-diol and 4- ((6-bromohexyl) oxy) -N-phenylaniline were dissolved in acetone with K 2CO3 in an N 2 atmosphere, N 2 was vented for 15min and reacted at 65℃for 36h. After cooling to room temperature, the solvent acetone was removed by rotary evaporation, and then a white solid was obtained by column chromatography. Subsequently, it was dried in a vacuum oven to obtain Ar 2 as a white solid.
Ar 1 and Ar 2 were dissolved with Cs 2CO3 in dehydrated DMSO in an atmosphere of N 2 and reacted at 130℃for 24h. After cooling to room temperature, the mixture was added dropwise to saturated NaCl ice water, suction filtration was performed, and then a final pale yellow solid was obtained by column chromatography. Subsequently, it was dried in a vacuum oven to obtain the cyclic TADF monomer as a pale yellow solid powder.
The polymer was synthesized by free radical polymerization in THF using Azobisisobutyronitrile (AIBN) as the free radical initiator. The cyclic TADF monomer and AIBN (2 mol% of the total monomer) were dissolved in freshly distilled THF solvent (total concentration about 0.2g mL -1), N 2 was vented for 15min, and reacted at 60 ℃ for 48 hours. Cooling to room temperature, column chromatography to obtain crude product, and dripping excessive methanol for 3 times to precipitate pure solid. Subsequently, it was centrifuged and dried in a vacuum oven to obtain the desired cyclic polymer in the form of a pale yellow solid.
The invention also aims to provide a preparation method of the flexible annular polymer-based organic electroluminescent material, which comprises the following specific steps:
and mixing the trifluoro triazine, the diphenylamine derivative, the Cs 2CO3 and the solvent, then carrying out reaction, and separating the obtained product system to obtain an intermediate product.
Ar 1 and Ar 2 (see specific embodiments) are mixed with K 2CO3 solvent and then react, and the obtained product system is separated to obtain a final product;
The reaction is carried out in a protective atmosphere, preferably the temperature of the reaction is preferably greater than 60 ℃, and more preferably 65 ℃; the reaction time is 24 to 48 hours, preferably 36 hours.
It is a further object of the present invention to provide the use of a triazine-based organic electroluminescent material obtained by a triazine-based organic electroluminescent preparation method in an organic electroluminescent display;
preferably, the triazine-based organic electroluminescent material is doped or undoped as a light emitting layer of an organic electroluminescent display.
Preferably, the organic electroluminescent display further comprises a cathode, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection layer.
Preferably, the organic electroluminescent display is provided with an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode in this order.
The foregoing is a preferred embodiment of the present application, and modifications, obvious to those skilled in the art, of the various equivalent forms of the present application can be made without departing from the principles of the present application, are intended to be within the scope of the appended claims.
Claims (4)
1. A flexible cyclic heat activated delayed fluorescence polymer characterized by: after the fluorenyl groups and the TADF molecules form a ring, the vinyl groups are subjected to self-polymerization or copolymerization to form a polymer with a side chain containing a cyclic TADF, and the independent structure of the TADF unit is as follows:
；
the fluorenyl unit independent structure is as follows:
；
wherein n is a degree of polymerization, and the degree of polymerization is an integer of 10 to 10000.
2. Use of a flexible cyclic heat activated delayed fluorescence polymer characterized by: use of a polymer according to claim 1 in a cyclic heat activated delayed fluorescence polymer luminescent material.
3. The utility model provides an electroluminescent device, includes glass, adheres to the electrically conductive glass substrate layer on glass, with the hole injection layer of electrically conductive glass substrate layer laminating, with the hole transport layer of hole injection layer laminating, with the luminescent layer of hole transport layer laminating, with the hole blocking layer of luminescent layer laminating, with the electron transport layer of hole blocking layer laminating, with the cathode layer of electron transport layer laminating, its characterized in that: the light-emitting layer comprising the polymer of claim 1.
4. An electroluminescent device as claimed in claim 3, characterized in that: the light-emitting layer is composed of a host material and a dopant material as a guest, and the guest material of the light-emitting layer is the polymer according to claim 1.
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| CN114057922A (en) * | 2021-12-09 | 2022-02-18 | 江苏海洋大学 | Thermally activated delayed fluorescence polymer host material with aggregation-induced fluorescence property |
| CN116891481A (en) * | 2023-01-31 | 2023-10-17 | 江苏海洋大学 | Annular white light thermal activation delayed fluorescence macromolecule |
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| KR102648402B1 (en) * | 2018-06-12 | 2024-03-18 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light emitting device including the same |
| US10954245B2 (en) * | 2019-04-16 | 2021-03-23 | Wuhan China Star Optoelectronics | Thermal active delay fluorescent material, method for manufacturing same, and organic light-emitting diode device |
| CN117264106A (en) * | 2023-09-20 | 2023-12-22 | 江苏海洋大学 | Efficient thermal-activation delayed fluorescence single-molecule white light polymer with vinyl main chain |
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| CN114057922A (en) * | 2021-12-09 | 2022-02-18 | 江苏海洋大学 | Thermally activated delayed fluorescence polymer host material with aggregation-induced fluorescence property |
| CN116891481A (en) * | 2023-01-31 | 2023-10-17 | 江苏海洋大学 | Annular white light thermal activation delayed fluorescence macromolecule |
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