WO2022088123A1 - Matériau à fluorescence retardée à activation thermique vert et son procédé de préparation - Google Patents

Matériau à fluorescence retardée à activation thermique vert et son procédé de préparation Download PDF

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Publication number
WO2022088123A1
WO2022088123A1 PCT/CN2020/125604 CN2020125604W WO2022088123A1 WO 2022088123 A1 WO2022088123 A1 WO 2022088123A1 CN 2020125604 W CN2020125604 W CN 2020125604W WO 2022088123 A1 WO2022088123 A1 WO 2022088123A1
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Prior art keywords
activated delayed
fluorescent material
delayed fluorescent
thermally activated
organic electroluminescent
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PCT/CN2020/125604
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English (en)
Chinese (zh)
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唐建新
谢凤鸣
李艳青
周经雄
曾馨逸
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苏州大学
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Priority to PCT/CN2020/125604 priority Critical patent/WO2022088123A1/fr
Publication of WO2022088123A1 publication Critical patent/WO2022088123A1/fr

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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the invention relates to the field of organic electroluminescent materials, in particular to a thermally activated delayed fluorescent material that can be industrialized and has good performance and an electroluminescent device thereof.
  • OLEDs Organic Light Emitting Diodes
  • the first-generation light-emitting device OLEDs based on conventional fluorescent materials show internal quantum efficiencies (IQEs) as high as 25% and external quantum efficiencies (EQEs) of 5–7.5%, because the emissive materials can only obtain singlet excitons.
  • IQEs internal quantum efficiencies
  • EQEs external quantum efficiencies
  • Second-generation phosphorescent materials containing noble metal atoms can effectively utilize singlet and triplet excitons for spin-orbit coupling, and their IQE can reach 100%; however, considering that iridium (Ir) and platinum (Pt) are scarce and Expensive, their application in the field of organic light-emitting materials is greatly limited.
  • the emerging third-generation light-emitting materials-thermally activated delayed fluorescence (TADF) materials do not contain metals, and TADF materials can pass triplet excitons from the lowest triplet excited state (T 1 ) through the inverse intersystem to single In the reexcited state (S 1 ), the IQE can also reach 100% by converting into photons, which is a promising and promising alternative to phosphorescent luminescent materials. big attention.
  • TADF materials For the vast majority of TADF materials, they suffer from a serious aggregation concentration quenching (ACQ) phenomenon.
  • ACQ aggregation concentration quenching
  • OLED devices When preparing OLED devices, they are doped in the host material as a guest material at a low concentration. Doped high-efficiency TADF materials are very rare. Therefore, if a TADF material that does not suffer from concentration quenching can be designed and synthesized, and high-efficiency undoped electroluminescent devices can be realized at the same time, it will have huge application prospects and economic value. .
  • the invention discloses a high-efficiency green thermally activated delayed fluorescent material and a preparation method thereof.
  • the chemical name of the thermally activated delayed fluorescent material is 3,5-bis(9H-carbazol-9-yl)-2,4,6-tris (3,6-di-tert-butyl-9H-carbazol-9-yl) benzonitrile, to solve the problems of serious concentration quenching of thermally activated delayed fluorescent materials and low efficiency of non-doped electroluminescent devices;
  • the existing TADF materials have many synthesis and preparation steps, expensive raw materials, complex synthesis and purification processes, low yields, and difficulty in mass production; especially, the OLED prepared by the high-concentration doped light-emitting layer of the thermally activated delayed fluorescent material , to achieve its goal of EQE exceeding 20% with low efficiency roll-off.
  • the thermally activated delayed fluorescent material of the present invention is 3,5-bis(9H-carbazol-9-yl)-2,4,6-tris(3,6-di-tert-butyl-9H-carbazol-9-yl) Benzonitrile, its chemical formula is: C 91 H 88 N 6 , and its chemical structural formula is as follows.
  • the preparation method of the above thermally activated delayed fluorescent material comprises the following steps: using 2,3,4,5,6-pentafluorobenzonitrile, 3,6-di-tert-butyl-9H-carbazole and 9H-carbazole as raw materials,
  • the green thermally activated delayed fluorescent material is prepared by a continuous one-pot reaction; the reaction can be referred to as follows.
  • reaction solution is poured into water, and then a large amount of solid is obtained by suction filtration.
  • product is separated and purified by column chromatography (petroleum ether/dichloromethane, volume ratio is 4:1) to obtain the thermal activation delay. fluorescent material.
  • the invention discloses the application of the above thermally activated delayed fluorescent material in the preparation of organic electroluminescence devices.
  • the light-emitting layer of the organic electroluminescence device includes the above-mentioned thermally activated delayed fluorescent material, and the thermally activated delayed fluorescent material is used as a guest material doped with a host material as the light-emitting layer, or directly used as the light-emitting layer; further, the thermally activated delayed fluorescent material is used as the light-emitting layer.
  • the doping concentration of the fluorescent material is 10-100 wt %.
  • the organic electroluminescent device based on the thermally activated delayed fluorescent material disclosed in the present invention is that indium tin oxide (ITO) is used as the anode, bispyrazino[2,3-f:2',3'-h]quinoxa Lino-2,3,6,7,10,11-capronitrile (HATCN) was used as a hole injection layer (HIL), 4,4'-(cyclohexane-1,1-diyl)bis(N, N-di-p-tolylaniline) (TAPC) was used as the hole transport layer (HTL) and 1,3-bis(9H-carbazol-9-yl)benzene (mCP) was used as the electron/exciton blocking layer ( EBL), the thermally activated delayed fluorescent material is used as a guest material doped with 1,3-bis(9H-carbazol-9-yl)benzene (mCP) host material and used as an emissive layer (EML), 4,6-bis (3,5-
  • the invention provides a method for synthesizing and preparing a novel thermally activated delayed fluorescent material; and an OLED based on the thermally activated delayed fluorescent material, which achieves the goal of having an EQE exceeding 20% and a low-efficiency roll-off; and is used to solve the problem of the thermally activated delayed fluorescent material.
  • the organic thin film formed by the invention has high surface smoothness, stable chemical and physical properties, high luminous efficiency and low concentration quenching properties, and the formed organic electroluminescent device has excellent performance.
  • Thermally activated delayed fluorescent materials are characterized by twisted internal charge transfer (TICT), thermally activated delayed fluorescence properties (TADF), 100% high fluorescence quantum yield (PLQY), good thermal stability, and a pure membrane state Advantages such as no aggregation concentration quenching (ACQ) effect.
  • TICT twisted internal charge transfer
  • TADF thermally activated delayed fluorescence properties
  • PLQY 100% high fluorescence quantum yield
  • ACQ no aggregation concentration quenching
  • the OLED device based on the thermally activated delayed fluorescent material provided by the present invention has the advantages of low driving voltage, high luminescence brightness and high luminescence stability, and the external quantum efficiency EQE of the doped device is as high as 26.8%.
  • the external quantum efficiency EQE is as high as 21.8%, and the external quantum efficiency EQE of the ultra-thick undoped device (80 nm light-emitting layer) is as high as 21.0%.
  • the efficiency roll-off of these devices is very small.
  • the thermally activated delayed fluorescent material provided by the present invention has few synthesis and preparation steps, cheap and readily available raw materials, simple synthesis and purification processes, high yield, and can be synthesized and prepared on a large scale.
  • Organic electroluminescent devices based on it have great application prospects and economic value in the fields of lighting and flat panel displays.
  • Figure 1 is the hydrogen NMR spectrum of Compound A prepared in Example 1.
  • FIG. 2 is the carbon nuclear magnetic spectrum of compound A prepared in Example 1.
  • FIG. 3 is the mass spectrum of Compound A prepared in Example 1.
  • FIG. 4 is an efficiency graph of an example device.
  • FIG. 5 is an efficiency plot of compound A undoped devices.
  • FIG. 6 is a graph of the efficiency of an undoped device of Compound B.
  • the raw materials involved in the present invention are all conventional commercial products, and the specific operation methods and testing methods are conventional methods in the field; especially the specific preparation process and the materials of each layer of the organic electroluminescent device based on the thermally activated delayed fluorescent material of the present invention are existing techniques, such as vacuum evaporation, the vacuum degree is ⁇ 2 ⁇ 10 -4 Pa, the deposition rate of the functional layer is 2 ⁇ /s, the deposition rate of the host material is 1 ⁇ /s, the deposition rate of the LiF layer is 0.1 ⁇ /s, and the deposition rate of the Al The deposition rate was 8 ⁇ /s.
  • the inventive step of the present invention is to provide a new thermally activated delayed fluorescent material with non-doped properties, which can be used as a light-emitting layer of an organic electroluminescent device alone by doped host material or by non-doped material.
  • the present invention provides an efficient green thermally activated delayed fluorescent material 3,5-bis(9H-carbazol-9-yl)-2,4,6-tris(3,6-di-tert-butyl-9H-carbazole- 9-yl) benzonitrile (compound A).
  • the reaction formula is as follows.
  • the reaction is specifically as follows.
  • Fig. 1 is the hydrogen nuclear magnetic spectrum of the compound A obtained above
  • Fig. 2 is the carbon nuclear magnetic spectrum of the compound A obtained above
  • Fig. 3 is the mass spectrum of the compound A obtained above.
  • the structure detection of compound A is as follows:
  • the fabrication steps of the organic electroluminescent device with A doping concentration of 10 wt% as the light-emitting layer are as follows.
  • Pretreatment of glass anode select a glass substrate (3 ⁇ 3 mm) with an indium tin oxide (ITO) film pattern as a transparent electrode; after cleaning the glass substrate with ethanol, UV-ozone processing to obtain a pretreated glass substrate.
  • ITO indium tin oxide
  • Vacuum evaporation carry out vacuum evaporation of each layer on the pretreated glass substrate by vacuum evaporation method, put the treated glass substrate into a vacuum evaporation chamber, and the degree of vacuum is ⁇ 2 ⁇ 10 ⁇ 4 Pa
  • the device structure is as follows: ITO/HAT-CN (10 nm)/TAPC (60 nm)/mCP (10 nm)/mCP: 10 wt% A (30 nm)/TMPYPB (45 nm)/LiF (1 nm )/Al (100 nm); the specific layer evaporation is a conventional technique.
  • Device packaging seal the fabricated organic electroluminescent device in a nitrogen atmosphere glove box with a water oxygen concentration of less than 1 ppm, and then cover the above-mentioned film formation with a sealing cover with epoxy UV-curable resin glass.
  • the substrate is sealed by UV curing; the specific encapsulation is conventional technology.
  • the fabrication steps of the organic electroluminescent device with A doping concentration of 15 wt% as the light-emitting layer are as follows.
  • Pretreatment of glass anode select a glass substrate (3 ⁇ 3 mm) with an indium tin oxide (ITO) film pattern as a transparent electrode; after cleaning the glass substrate with ethanol, UV-ozone processing to obtain a pretreated glass substrate.
  • ITO indium tin oxide
  • Vacuum evaporation carry out vacuum evaporation of each layer on the pretreated glass substrate by vacuum evaporation method, put the treated glass substrate into a vacuum evaporation chamber, and the degree of vacuum is ⁇ 2 ⁇ 10 ⁇ 4 Pa
  • the device structure is as follows: ITO/HAT-CN (10 nm)/TAPC (60 nm)/mCP (10 nm)/mCP: 15 wt% A (30 nm)/TMPYPB (45 nm)/LiF (1 nm )/Al (100 nm); the specific layer evaporation is a conventional technique.
  • Device packaging seal the fabricated organic electroluminescent device in a nitrogen atmosphere glove box with a water oxygen concentration of less than 1 ppm, and then cover the above-mentioned film formation with a sealing cover with epoxy UV-curable resin glass.
  • the substrate is sealed by UV curing; the specific encapsulation is conventional technology.
  • the fabrication steps of the organic electroluminescent device with A doping concentration of 20 wt% as the light-emitting layer are as follows.
  • Pretreatment of glass anode select a glass substrate (3 ⁇ 3 mm) with an indium tin oxide (ITO) film pattern as a transparent electrode; after cleaning the glass substrate with ethanol, UV-ozone processing to obtain a pretreated glass substrate.
  • ITO indium tin oxide
  • Vacuum evaporation carry out vacuum evaporation of each layer on the pretreated glass substrate by vacuum evaporation method, put the treated glass substrate into a vacuum evaporation chamber, and the degree of vacuum is ⁇ 2 ⁇ 10 ⁇ 4 Pa
  • the device structure is as follows: ITO/HAT-CN (10 nm)/TAPC (60 nm)/mCP (10 nm)/mCP: 20 wt% A (30 nm)/TMPYPB (45 nm)/LiF (1 nm) )/Al (100 nm); the specific layer evaporation is a conventional technique.
  • Device packaging seal the fabricated organic electroluminescent device in a nitrogen atmosphere glove box with a water oxygen concentration of less than 1 ppm, and then cover the above-mentioned film formation with a sealing cover with epoxy UV-curable resin glass.
  • the substrate is sealed by UV curing; the specific encapsulation is conventional technology.
  • the fabrication steps of the organic electroluminescent device with A doping concentration of 30 wt% as the light-emitting layer are as follows.
  • Pretreatment of glass anode select a glass substrate (3 ⁇ 3 mm) with an indium tin oxide (ITO) film pattern as a transparent electrode; after cleaning the glass substrate with ethanol, UV-ozone processing to obtain a pretreated glass substrate.
  • ITO indium tin oxide
  • Vacuum evaporation carry out vacuum evaporation of each layer on the pretreated glass substrate by vacuum evaporation method, put the treated glass substrate into a vacuum evaporation chamber, and the degree of vacuum is ⁇ 2 ⁇ 10 ⁇ 4 Pa
  • the device structure is as follows: ITO/HAT-CN (10 nm)/TAPC (60 nm)/mCP (10 nm)/mCP: 30 wt% A (30 nm)/TMPYPB (45 nm)/LiF (1 nm )/Al (100 nm); the specific layer evaporation is a conventional technique.
  • Device packaging seal the fabricated organic electroluminescent device in a nitrogen atmosphere glove box with a water oxygen concentration of less than 1 ppm, and then cover the above-mentioned film formation with a sealing cover with epoxy UV-curable resin glass.
  • the substrate is sealed by UV curing; the specific encapsulation is conventional technology.
  • the fabrication steps of the organic electroluminescent device with A doping concentration of 50 wt% as the light-emitting layer are as follows.
  • Pretreatment of glass anode select a glass substrate (3 ⁇ 3 mm) with an indium tin oxide (ITO) film pattern as a transparent electrode; after cleaning the glass substrate with ethanol, UV-ozone processing to obtain a pretreated glass substrate.
  • ITO indium tin oxide
  • Vacuum evaporation carry out vacuum evaporation of each layer on the pretreated glass substrate by vacuum evaporation method, put the treated glass substrate into a vacuum evaporation chamber, and the degree of vacuum is ⁇ 2 ⁇ 10 ⁇ 4 Pa
  • the device structure is as follows: ITO/HAT-CN (10 nm)/TAPC (60 nm)/mCP (10 nm)/mCP: 50 wt% A (30 nm)/TMPYPB (45 nm)/LiF (1 nm )/Al (100 nm); the specific layer evaporation is a conventional technique.
  • Device packaging seal the fabricated organic electroluminescent device in a nitrogen atmosphere glove box with a water oxygen concentration of less than 1 ppm, and then cover the above-mentioned film formation with a sealing cover with epoxy UV-curable resin glass.
  • the substrate is sealed by UV curing; the specific encapsulation is conventional technology.
  • the fabrication steps of the organic electroluminescent device with A doping concentration of 100 wt% as the light-emitting layer are as follows.
  • Pretreatment of glass anode select a glass substrate (3 ⁇ 3 mm) with an indium tin oxide (ITO) film pattern as a transparent electrode; after cleaning the glass substrate with ethanol, UV-ozone processing to obtain a pretreated glass substrate.
  • ITO indium tin oxide
  • Vacuum evaporation carry out vacuum evaporation of each layer on the pretreated glass substrate by vacuum evaporation method, put the treated glass substrate into a vacuum evaporation chamber, and the degree of vacuum is ⁇ 2 ⁇ 10 ⁇ 4 Pa
  • the device structure is as follows. ITO/HAT-CN (10 nm)/TAPC (60 nm)/mCP (10 nm)/100 wt% A (30 nm)/TMPYPB (45 nm)/LiF (1 nm)/Al (100 nm); specific Evaporation of the layers is a conventional technique.
  • Device packaging seal the fabricated organic electroluminescent device in a nitrogen atmosphere glove box with a water oxygen concentration of less than 1 ppm, and then cover the above-mentioned film formation with a sealing cover with epoxy UV-curable resin glass.
  • the substrate is sealed by UV curing; the specific encapsulation is conventional technology.
  • the fabrication steps of the organic electroluminescent device with 80 nm material A as the light-emitting layer are as follows.
  • Pretreatment of glass anode select a glass substrate (3 ⁇ 3 mm) with an indium tin oxide (ITO) film pattern as a transparent electrode; after cleaning the glass substrate with ethanol, UV-ozone processing to obtain a pretreated glass substrate.
  • ITO indium tin oxide
  • Vacuum evaporation carry out vacuum evaporation of each layer on the pretreated glass substrate by vacuum evaporation method, put the treated glass substrate into a vacuum evaporation chamber, and the degree of vacuum is ⁇ 2 ⁇ 10 ⁇ 4 Pa, the device structure is as follows: ITO/HAT-CN (10 nm)/TAPC (40 nm)/mCP (10 nm)/A (80 nm)/TMPYPB (45 nm)/LiF (1 nm)/Al (100 nm) nm); the specific layer evaporation is a conventional technique.
  • Device packaging seal the fabricated organic electroluminescent device in a nitrogen atmosphere glove box with a water oxygen concentration of less than 1 ppm, and then cover the above-mentioned film formation with a sealing cover with epoxy UV-curable resin glass.
  • the substrate is sealed by UV curing; the specific encapsulation is conventional technology.
  • Direct current was applied to the fabricated organic electroluminescent device, and the luminescence performance was evaluated by using an integrating sphere; the current-voltage characteristics were measured by a computer-controlled Keithley 2400 digital source meter.
  • the luminescence properties of the organic electroluminescent device were measured under the condition of changing the applied DC voltage.
  • the device performance is shown in Figure 5.
  • the turn-on voltage is 3.0 V
  • the maximum external quantum efficiency is 21.0%
  • the electroluminescence peak is 510 nm.
  • Pretreatment of glass anode select a glass substrate (3 ⁇ 3 mm) with an indium tin oxide (ITO) film pattern as a transparent electrode; after cleaning the glass substrate with ethanol, UV-ozone processing to obtain a pretreated glass substrate.
  • ITO indium tin oxide
  • Vacuum evaporation carry out vacuum evaporation of each layer on the pretreated glass substrate by vacuum evaporation method, put the treated glass substrate into a vacuum evaporation chamber, and the degree of vacuum is ⁇ 2 ⁇ 10 ⁇ 4 Pa, the device structure is as follows: ITO/HAT-CN (10 nm)/TAPC (40 nm)/mCP (10 nm)/B (80 nm)/TMPYPB (45 nm)/LiF (1 nm)/Al (100 nm); the specific layer evaporation is a conventional technique.
  • Device packaging seal the fabricated organic electroluminescent device in a nitrogen atmosphere glove box with a water oxygen concentration of less than 1 ppm, and then cover the above-mentioned film formation with a sealing cover with epoxy UV-curable resin glass.
  • the substrate is sealed by UV curing; the specific encapsulation is conventional technology.
  • Direct current was applied to the fabricated organic electroluminescent device, and the luminescence performance was evaluated by using an integrating sphere; the current-voltage characteristics were measured by a computer-controlled Keithley 2400 digital source meter.
  • the luminescence properties of the organic electroluminescent device were measured under the condition of changing the applied DC voltage.
  • the device performance is shown in Figure 6, the turn-on voltage is 3.5 V, the maximum external quantum efficiency is 9.2%, and the electroluminescence peak is 522 nm.
  • the organic electroluminescence device based on the material provided by the present invention can emit sky blue to green fluorescence (luminescence peak at 488 to 504 nm), the maximum external quantum efficiency of the doped device is as high as 26.8%, and the maximum external quantum efficiency of the non-doped device is as high as 21.8% , and has the advantages of low driving voltage and good luminous stability.
  • Organic electroluminescent devices based on it have great application prospects and economic value in the fields of lighting and flat panel displays.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un matériau à fluorescence retardée à activation thermique vert ayant des propriétés de non dopage et son procédé de préparation. Le matériau est le 3,5-bis(9H-carbazol-9-yl)-2,4,6-tris(3,6-ditert-Butyl-9H-carbazol-9-yl)benzonitrile. Le composé selon l'invention a un grand angle de torsion entre un donneur et un accepteur, et est caractérisé par un transfert de charge interne torsadé (TICT), et par les avantages d'avoir des propriétés typiques de fluorescence retardée à activation thermique (TADF), un haut rendement quantique de fluorescence (PLQY) de 100 %, et une stabilité thermique élevée. De surcroît, le composé n'a pas d'effet d'extinction par concentration d'agrégat (ACQ) lorsqu'il est dans un état de film pur. De plus, le matériau a peu d'étapes de synthèse et de préparation, des matières premières facilement disponibles, des procédés de synthèse et de purification simples, et un haut rendement, et peut être synthétisé et préparé à grande échelle.
PCT/CN2020/125604 2020-10-30 2020-10-30 Matériau à fluorescence retardée à activation thermique vert et son procédé de préparation WO2022088123A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105602553A (zh) * 2016-03-18 2016-05-25 太原理工大学 基于4-氟苯乙腈的热活化型延迟荧光材料及其制备和应用
CN110366548A (zh) * 2017-02-24 2019-10-22 国立大学法人九州大学 化合物、发光材料及发光元件
CN111100060A (zh) * 2019-12-11 2020-05-05 江苏大学 一种咔唑类热激活延迟荧光材料及制备方法
CN111777542A (zh) * 2020-05-20 2020-10-16 东南大学 一种可溶液加工的热激活延迟荧光材料及其制法和应用

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CN105602553A (zh) * 2016-03-18 2016-05-25 太原理工大学 基于4-氟苯乙腈的热活化型延迟荧光材料及其制备和应用
CN110366548A (zh) * 2017-02-24 2019-10-22 国立大学法人九州大学 化合物、发光材料及发光元件
CN111100060A (zh) * 2019-12-11 2020-05-05 江苏大学 一种咔唑类热激活延迟荧光材料及制备方法
CN111777542A (zh) * 2020-05-20 2020-10-16 东南大学 一种可溶液加工的热激活延迟荧光材料及其制法和应用

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Title
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