WO2020237885A1 - Matériau à fluorescence retardée bleu foncé à activation thermique, son procédé de préparation et dispositif électroluminescent - Google Patents

Matériau à fluorescence retardée bleu foncé à activation thermique, son procédé de préparation et dispositif électroluminescent Download PDF

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WO2020237885A1
WO2020237885A1 PCT/CN2019/103503 CN2019103503W WO2020237885A1 WO 2020237885 A1 WO2020237885 A1 WO 2020237885A1 CN 2019103503 W CN2019103503 W CN 2019103503W WO 2020237885 A1 WO2020237885 A1 WO 2020237885A1
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electron
dark blue
donating group
fluorescent material
mixed solution
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罗佳佳
张曲
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武汉华星光电半导体显示技术有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
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    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

Definitions

  • the invention relates to a display field technology, in particular to a dark blue thermally activated delayed fluorescent material, a preparation method thereof, and an electroluminescent device.
  • OLEDs Organic light-emitting diodes
  • OLEDs do not require a backlight for active light emission, have high luminous efficiency, large viewing angle, fast response speed, large temperature adaptation range, relatively simple production and processing technology, and low driving voltage.
  • Low energy consumption, lighter and thinner, flexible display and other advantages and huge application prospects have attracted the attention of many researchers.
  • the light-emitting guest material is very important.
  • the light-emitting guest materials used in early OLEDs were fluorescent materials. Since the ratio of singlet and triplet excitons in OLEDs is 1:3, the theoretical internal quantum efficiency (IQE) of OLEDs based on fluorescent materials is only It can reach 25%, which greatly limits the application of fluorescent electroluminescent devices.
  • IQE theoretical internal quantum efficiency
  • heavy metal complex phosphorescent materials can simultaneously utilize singlet and triplet excitons to achieve 100% IQE.
  • the commonly used heavy metals are all precious metals such as Ir and Pt, which are expensive, and phosphorescent luminescent materials still need a breakthrough in blue light materials.
  • Organic thermally activated delayed fluorescence (TADF) materials through clever molecular design, make the molecules have a small minimum single triplet energy difference ( ⁇ E ST ), so that the triplet excitons can cross through the reverse system (reverse intersystem crossing, RISC) returns to the singlet state, and then emits light through the radiation transition to the ground state, thereby simultaneously using singlet and triplet excitons to achieve 100% IQE.
  • TADF organic thermally activated delayed fluorescence
  • TADF materials For TADF materials, fast reverse intersystem crossing constant (k RISC ) and high photoluminescence quantum yield (PLQY) are necessary conditions for the preparation of high-efficiency OLEDs. At present, TADF materials with the above conditions are still relatively scarce compared to phosphorescent heavy metal complex materials. In the dark blue field where phosphorescent heavy metal complex materials need to be broken, TADF materials are even rarer.
  • k RISC fast reverse intersystem crossing constant
  • PLQY photoluminescence quantum yield
  • the present invention synthesizes a series of dark blue TADF materials with high yield and high PLQY through clever molecular design, which can effectively reduce the highest occupied molecular orbital (HOMO) and the lowest potential. Occupy the molecular orbital (lowest occupied molecular orbital, LUMO) degree of overlap, thereby obtaining a small ⁇ E ST , thereby improving the efficiency of the device.
  • HOMO highest occupied molecular orbital
  • LUMO lowest occupied molecular orbital
  • Their structures were confirmed by NMR and carbon spectroscopy, and then their photophysical properties were studied in detail.
  • a series of high-performance dark blue TADF OLEDs were prepared based on these luminescent materials.
  • the present invention conducts in-depth research on the hot thermally activated delayed fluorescent materials currently studied, and designs and synthesizes molecular systems of D1-A-D2 structures with different electron donors, in which D1 is the first The electron group, D2 is the second electron donating group, and A is the electron acceptor.
  • the present invention provides a dark blue thermally activated delayed fluorescent material.
  • the dark blue thermally activated delayed fluorescent material consists of a first electron-donating group, a second electron-donating group, and 2,-6-dibromo-4-methylpyridine Combined with nitrogen oxides, its general structural formula is:
  • D1 is the first electron-donating group
  • D2 is the second electron-donating group
  • the first electron-donating group is different from the second electron-donating group.
  • the first electron donating group is selected from one of the following materials:
  • the second electron donating group is selected from one of the following materials:
  • the present invention also provides a method for synthesizing dark blue thermally activated delayed fluorescent material, which includes the following steps:
  • the raw materials of the first electron-donating group, the electron acceptor, and the catalyst are placed in a reaction vessel to fully react to obtain a first mixed solution.
  • the first mixed solution includes the first electron-donating group.
  • the first mixed solution is cooled to room temperature, the mixed solution is extracted to obtain the first compound, and the first compound is combined and purified to obtain the intermediate;
  • the raw materials of the second electron donating group, the intermediate and the catalyst are placed in a reaction vessel to obtain a second mixed solution, and the second mixed solution includes the intermediate and the The raw material of the second electron donating group;
  • the second mixed solution is cooled to room temperature, the mixed solution is extracted to obtain a second compound, and the second compound is combined and purified to obtain a dark blue thermally activated delayed fluorescent material.
  • the raw material of the first electron-donating group is selected from 4-carbazole phenylboronic acid, 4-(3,6-dimethylcarbazole)-phenylboronic acid, 4-(3,6-diphenylcarbazole) Azole)-a kind of phenylboronic acid.
  • the electron acceptor is 2,-6-dibromo-4-methylpyridine oxynitride.
  • the raw material of the second electron donating group is 4-(9,10-dihydro-9,9-diphenylacridine)-phenylboronic acid.
  • the catalyst used in the first mixing configuration step includes K 2 CO 3 and Pd(PPh 3 ) 4 .
  • the catalyst used in the second mixing configuration step includes K2CO3 and Pd(PPh3)4.
  • the molar ratio of the electron acceptor to the raw material of the first electron donating group is 1:1 to 1:5.
  • the molar ratio of the intermediate to the raw material of the second electron donating group is 1:1 to 1:5.
  • reaction temperature of the first mixed solution preparation step is 80-90 degrees Celsius, and the reaction time is at least 12 hours.
  • reaction temperature of the second mixed solution preparation step is 80-90 degrees Celsius, and the reaction time is at least 12 hours.
  • the step of preparing the first mixed solution includes combining the raw material of the first electron-donating group, 2,-6-dibromo-4-methylpyridine oxynitride, K 2 CO 3 and Pd(PPh 3 ) 4 Placed together in the reaction vessel, pumped through three times, then placed the reaction vessel in an argon atmosphere, and added deoxygenated glycol dimethyl ether to the reaction vessel at 80°C. Perform reflux reaction at 90 degrees for at least 12 hours and then cool to room temperature to obtain a first mixed solution.
  • the step of preparing the second mixed solution includes placing the raw material of the second electron donating group, the intermediate, K 2 CO 3 and Pd(PPh 3 ) 4 together in the reaction vessel, and pumping Pass three times, then place the reaction vessel in an argon atmosphere, add deoxygenated ethylene glycol dimethyl ether to the reaction vessel, reflux for at least 12 hours at 80-90 degrees Celsius, and then cool to room temperature , To obtain the second mixed solution.
  • the first extraction step includes pouring the first mixed solution into ice water, using dichloromethane for multiple extractions, and combining the organic phases to obtain the first compound; using a developing agent, passing through a silica gel column The first compound is purified by chromatography to obtain the intermediate.
  • the developing agent in the silica gel column chromatography method comprises dichloromethane and n-hexane, and the volume ratio of the dichloromethane and the n-hexane is 1:3.
  • the second extraction step includes pouring the second mixed solution into ice water, using dichloromethane for multiple extractions, and combining the organic phases to obtain the second compound; using a developing agent, passing through a silica gel column
  • the chromatographic method is used to purify the second compound for the first time to obtain the initial purified product, and the initial purified product is purified using a sublimation apparatus, and finally the dark blue thermally activated delayed fluorescent material is obtained.
  • the developing agent in the silica gel column chromatography method comprises dichloromethane and n-hexane, and the volume ratio of the dichloromethane and the n-hexane is 1:1.
  • the present invention also provides an electroluminescent device, including:
  • the luminescent material of the luminescent layer has a general structural formula as follows:
  • D1 is a first electron-donating group
  • D2 is a second electron-donating group
  • the first electron-donating group is different from the second electron-donating group.
  • the first electron donating group is selected from one of the following materials:
  • the second electron donating group is selected from one of the following materials:
  • the present invention adjusts the torsion angle between the electron donor and the electron acceptor and the charge transfer characteristics, so as to achieve the purpose of reducing the lowest single triplet energy level difference and deep blue emission of molecules. Make the molecules have excellent luminescence properties.
  • the electroluminescent device made based on the dark blue TADF material provided by the present invention achieves very high luminous efficiency.
  • Figure 1 is a photoluminescence spectrum of a dark blue thermally activated delayed fluorescent material synthesized in an embodiment of the present invention in a toluene solution at room temperature;
  • Figure 2 is a schematic diagram of the structure of the electroluminescent device described in the embodiment of the present invention.
  • the present invention provides a dark blue thermally activated delayed fluorescent material.
  • the dark blue thermally activated delayed fluorescent material consists of a first electron donating group, a second electron donating group, and 2,-6-dibromo-4-methylpyridine Combined with nitrogen oxides, its general structural formula is:
  • D1 is the first electron-donating group
  • D2 is the second electron-donating group
  • the first electron-donating group is different from the second electron-donating group
  • the first electron donating group is selected from one of the following materials:
  • the second electron donating group is selected from one of the following materials:
  • the present invention also provides a method for synthesizing dark blue thermally activated delayed fluorescence.
  • the following specific descriptions are given through Examples 1-3.
  • the first mixed solution preparation step wherein, in this implementation, the raw material of the first electron-donating group (4-carbazole phenylboronic acid, 2.87 g, 10 mmol) and 2,-6-dibromo-4-methylpyridine nitrogen oxide (2.67g, 10mmol) and the catalyst (K2CO3, 2.76g, 20mmol and Pd(PPh3)4, 0.575g, 0.5mmol) were placed in the reaction vessel, pumped three times, and injected the previously deoxygenated ethyl acetate under an argon atmosphere. Glycol dimethyl ether (100ml), followed by reflux reaction at 85 degrees Celsius for 12 hours to obtain a first mixed solution.
  • the raw material of the first electron-donating group (4-carbazole phenylboronic acid, 2.87 g, 10 mmol) and 2,-6-dibromo-4-methylpyridine nitrogen oxide (2.67g, 10mmol) and the catalyst (K2CO3, 2.76g, 20mmol and Pd(PPh
  • the first mixed solution includes 4-carbazole phenylboronic acid and 2,-6-dibromo- Intermediate produced by the reaction of 4-picoline nitrogen oxide (2-bromo-4-methyl-6-(4-carbazolephenyl)-pyridine nitrogen oxide).
  • the first mixed solution is cooled to room temperature and poured into ice water (200ml), and extracted three times (100ml of methylene chloride is added each time), and the organic phases are combined to obtain compound 1;
  • the compound 1 was first purified by silica gel column chromatography to obtain 3.17 g of the intermediate with a yield of 74%.
  • the developing agent is made by dichloromethane and n-hexane in a volume ratio of 1:3.
  • the intermediate is a white powder
  • the white powder is analyzed according to the detection requirements by the detection equipment.
  • the raw material for the second electron donating group (4-(9,10-dihydro-9,9-diphenylacridine)-phenylboronic acid, 2.7g, 6mmol) and the intermediate Body (2-bromo-4-methyl-6-(4-carbazolephenyl)-pyridine nitrogen oxide, 2.15g, 5mmol) and catalyst (K2CO3, 1.38g, 10mmol and Pd(PPh3) 4, 0.29g) , 0.25mmol) was placed in the reaction vessel, pumped three times, injected in the previously deoxygenated ethylene glycol dimethyl ether (100ml) under an argon atmosphere, and then refluxed at 85 degrees Celsius for 12 hours to obtain the second A mixed solution, the second mixed solution includes the intermediate (2-bromo-4-methyl-6-(4-carbazolephenyl)-pyridine oxynitride) and 4-(9,10-bis Hydro-9,9-diphenylacridine)-phenylboronic acid.
  • the second extraction step is to cool the second mixed solution to room temperature and pour it into ice water (200ml), perform three extractions (add 100ml of dichloromethane each time), combine the organic phases to obtain compound 2; use
  • the developing solvent was used to purify the compound 2 for the first time by silica gel column chromatography to obtain 2.28 g of the first initial purified product with a yield of 60%.
  • the first initial purified product 1 was purified using a sublimation apparatus to obtain 1.3g of the deep blue thermally activated delayed fluorescent material of formula (1).
  • the developing agent is made by dichloromethane and n-hexane with a volume ratio of 1:1.
  • the dark blue thermally activated delayed fluorescent material of formula (1) is a white powder, and the white powder is analyzed by a detection device according to the detection requirements.
  • Example 1 The chemical reaction process of Example 1 is as follows:
  • a dark blue thermally activated delayed fluorescent material with high synthesis yield and high photoluminescence efficiency is designed.
  • the first mixed solution preparation step wherein, in this implementation, the raw material of the first electron donating group (4-(3,6-dimethylcarbazole)-phenylboronic acid, 3.15g, 10mmol) and 2,-6-di Bromo-4-methylpyridine nitrogen oxide (2.67g, 10mmol) and catalyst (K2CO3, 2.76g, 20mmol and Pd(PPh3)4, 0.575g, 0.5mmol) were placed in the reaction vessel, pumped three times, Glycol dimethyl ether (100ml) deoxygenated in advance was injected in an air atmosphere, and then refluxed at 85 degrees Celsius for 12 hours to obtain a first mixed solution.
  • the raw material of the first electron donating group (4-(3,6-dimethylcarbazole)-phenylboronic acid, 3.15g, 10mmol) and 2,-6-di Bromo-4-methylpyridine nitrogen oxide (2.67g, 10mmol) and catalyst (K2CO3, 2.76g, 20mmol and Pd(PP
  • the first mixed solution contained 4-(3, The intermediate (2-bromo-4-methyl-6-(4-(3) produced by the reaction of 6-dimethylcarbazole)-phenylboronic acid and 2,-6-dibromo-4-methylpyridine nitrogen oxide ,6-Dimethylcarbazole)-phenyl)-pyridine oxynitride).
  • the first mixed solution is cooled to room temperature and poured into ice water (200ml), and extracted three times (each time adding 100ml of dichloromethane), and the organic phases are combined to obtain compound 3;
  • the compound 3 was first purified by silica gel column chromatography to obtain 3.01 g of the intermediate with a yield of 66%.
  • the developing agent is made by dichloromethane and n-hexane in a volume ratio of 1:3.
  • the intermediate is a white powder
  • the white powder is analyzed by testing equipment according to the testing requirements.
  • the analysis results are: 1H NMR (300MHz, CD2Cl2, ⁇ ): 8.80 (s, 1H), 8.03 (s, 1H), 7.89-7.92 (m, 5H), 7.53 (m, 2H), 7.38 (m, 1H), 7.19 (s, 1H), 6.96 (m, 1H), 2.45(s, 3H).
  • the second mixed solution is cooled to room temperature and poured into ice water (200ml), and extracted three times (each time adding 100ml of dichloromethane), and the organic phases are combined to obtain compound 4;
  • the compound 4 was first purified by silica gel column chromatography using a developing solvent to obtain 2.20 g of the initial purified product 2 with a yield of 56%.
  • the initial purified product 2 was purified using a sublimation apparatus to obtain 1.1 g The dark blue thermally activated delayed fluorescent material of formula (2).
  • the developing agent is made by dichloromethane and n-hexane with a volume ratio of 1:1.
  • the compound is a white powder.
  • the white powder is analyzed by the detection equipment according to the detection requirements. The analysis results are: 1H NMR (300MHz, CD2Cl2, ⁇ ): 8.80( s, 1H), 8.03 (s, 1H), 7.89-7.92 (m, 5H), 7.73 (m, 2H), 7.53 (m, 1H), 7.38 (m, 3H), 7.19-7.26 (m, 16H) , 6.96 (m, 5H), 2.46 (s, 6H), 2.45 (s, 3H).
  • Example 2 The chemical reaction process of Example 2 is as follows:
  • a dark blue thermally activated delayed fluorescent material with high synthesis yield and high photoluminescence efficiency is designed.
  • the first mixed solution preparation step wherein, in this implementation, the raw material of the first electron donating group (4-(3,6-diphenylcarbazole)-phenylboronic acid, 4.39g, 10mmol) and 2,-6-di Bromo-4-methylpyridine nitrogen oxide (2.67g, 10mmol) and catalyst (K2CO3, 2.76g, 20mmol and Pd(PPh3)4, 0.575g, 0.5mmol) were placed in the reaction vessel, pumped three times, Glycol dimethyl ether (100ml) deoxygenated in advance was injected in an air atmosphere, and then refluxed at 85 degrees Celsius for 12 hours to obtain a first mixed solution.
  • the raw material of the first electron donating group (4-(3,6-diphenylcarbazole)-phenylboronic acid, 4.39g, 10mmol) and 2,-6-di Bromo-4-methylpyridine nitrogen oxide (2.67g, 10mmol) and catalyst (K2CO3, 2.76g, 20mmol and Pd
  • the first mixed solution contained 4-(3, 6-Diphenylcarbazole)-phenylboronic acid and 2,-6-dibromo-4-methylpyridine nitrogen oxide reaction intermediate (2-bromo-4-methyl-6-(4-(3 ,6-Dimethylcarbazole)-phenyl)-pyridine oxynitride).
  • the first extraction step the first mixed solution was cooled to room temperature and poured into ice water (200ml), and extracted three times (each time adding 100ml of dichloromethane), and the organic phases were combined to obtain compound 5; Using a developing solvent, the compound 5 was first purified by silica gel column chromatography to obtain 3.60 g of the intermediate with a yield of 62%.
  • the developing agent is made by dichloromethane and n-hexane in a volume ratio of 1:3.
  • the intermediate is a white powder
  • the obtained white powder is analyzed by testing equipment according to the testing requirements.
  • the results of the analysis are: 1H NMR (300MHz, CD2Cl2, ⁇ ): 8.30 (m, 1H), 8.13 (m, 1H), 7.89-7.99 (m, 7H), 7.75-7.77 (m, 5H), 7.49-7.53 (m, 7H), 7.19 (s, 1H) ,2.45(s,3H).
  • the raw material for the second electron donating group (4-(9,10-dihydro-9,9-diphenylacridine)-phenylboronic acid, 2.7g, 6mmol) and the intermediate Body (2-bromo-4-methyl-6-(4-(3,6-dimethylcarbazole)-phenyl)-pyridine nitrogen oxide, 2.90g, 5mmol) and catalyst (K2CO3, 1.38g, 10mmol and Pd(PPh3)4, 0.29g, 0.25mmol) were placed in the reaction vessel, pumped through three times, injected in ethylene glycol dimethyl ether (50ml) deoxygenated in an argon atmosphere, and then heated at 85°C The reflux reaction was continued for 12 hours to obtain a second mixed solution, the second mixed solution including the intermediate (2-bromo-4-methyl-6-(4-(3,6-dimethylcarbazole) )-Phenyl)-pyridine oxynitride) and 4-(9,10-
  • the second extraction step cool the second mixed solution to room temperature and pour it into ice water (200ml), and perform three extractions (each adding 100ml of dichloromethane), and combine the organic phases to obtain compound 6;
  • the initial purification of the compound 6 was performed by silica gel column chromatography using a developing solvent to obtain 2.05 g of the initial purified product 3 with a yield of 45%.
  • the initial purified product 3 was purified using a sublimation apparatus to obtain 1.0 g is the dark blue thermally activated delayed fluorescent material of formula (3).
  • the developing agent is made by dichloromethane and n-hexane with a volume ratio of 1:1.
  • the compound 3 is a white powder, and the obtained white powder is analyzed by the detection equipment according to the detection requirements.
  • the analysis results are: 1H NMR (300MHz, CD2Cl2, ⁇ ): 8.30 (m, 1H), 8.13 (m, 1H), 7.89-7.99 (m, 7H), 7.75-7.77 (m, 7H), 7.37-7.49 (m, 8H), 7.19-7.26 (m, 16H), 6.95 (m, 2H), 2.45 (s, 3H).
  • a dark blue thermally activated delayed fluorescent material with high synthesis yield and high photoluminescence efficiency is designed.
  • Example 1 The following is a parameter analysis of the dark blue thermally activated delayed fluorescent materials synthesized in Example 1, Example 2 and Example 3.
  • the analysis data is shown in Table (1) below.
  • the present invention also provides an electroluminescent device.
  • an electroluminescent device In order to make the description clearer, the following specific descriptions are given through Examples 4-6.
  • the present invention also provides a first electroluminescent device, comprising: a substrate layer 1; a hole transport and injection layer 2 disposed on the substrate layer 1; and a light emitting layer 3, It is provided on the hole transport and injection layer 2; an electron transport layer 4 is provided on the light-emitting layer 3; and a cathode layer 5 is provided on the electron transport layer 4.
  • the material of the substrate layer 1 includes glass and conductive glass (ITO), and a layer of 50nm poly 3,4-ethylenedioxythiophene: polystyrene sulfonate is spin-coated on the substrate layer 1 after cleaning.
  • ITO glass and conductive glass
  • a layer of 50nm poly 3,4-ethylenedioxythiophene: polystyrene sulfonate is spin-coated on the substrate layer 1 after cleaning.
  • the material of the light-emitting layer 3 is the dark blue thermally activated fluorescent material synthesized in Example 1.
  • the present invention also provides a first electroluminescent device, comprising: a substrate layer 1; a hole transport and injection layer 2 disposed on the substrate layer 1; and a light emitting layer 3, It is provided on the hole transport and injection layer 2; an electron transport layer 4 is provided on the light-emitting layer 3; and a cathode layer 5 is provided on the electron transport layer 4.
  • the material of the substrate layer 1 includes glass and conductive glass (ITO), and a layer of 50nm poly 3,4-ethylenedioxythiophene: polystyrene sulfonate is spin-coated on the substrate layer 1 after cleaning.
  • ITO glass and conductive glass
  • a layer of 50nm poly 3,4-ethylenedioxythiophene: polystyrene sulfonate is spin-coated on the substrate layer 1 after cleaning.
  • the material of the light-emitting layer 3 is the deep blue thermally activated fluorescent material synthesized in Example 2.
  • the present invention also provides a third electroluminescent device, including: a substrate layer 1; a hole transport and injection layer 2 disposed on the substrate layer 1, and a light emitting layer 3, It is provided on the hole transport and injection layer 2; an electron transport layer 4 is provided on the light-emitting layer 3; and a cathode layer 5 is provided on the electron transport layer 4.
  • the material of the substrate layer 1 includes glass and conductive glass (ITO), and a layer of 50nm poly 3,4-ethylenedioxythiophene: polystyrene sulfonate is spin-coated on the substrate layer 1 after cleaning.
  • ITO glass and conductive glass
  • a layer of 50nm poly 3,4-ethylenedioxythiophene: polystyrene sulfonate is spin-coated on the substrate layer 1 after cleaning.
  • the material of the light-emitting layer 3 is the dark blue thermally activated fluorescent material synthesized in Example 3.
  • the current-brightness-voltage characteristics of the first electroluminescent device, the second electroluminescent device, and the third electroluminescent device are measured by a Keithley source measurement system with a calibrated silicon photodiode (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter), the electroluminescence spectrum was measured by the French JY company SPEX CCD3000 spectrometer, all measurements were done in the atmosphere at room temperature.
  • the performance data of the first electroluminescent device, the second electroluminescent device and the third electroluminescent device are shown in the following table (2):
  • the electroluminescent device manufactured by using the dark blue thermally activated delayed fluorescent material provided by the present invention has higher luminous brightness, high manufacturing efficiency and long service life.

Abstract

Matériau à fluorescence retardée bleu foncé à activation thermique, son procédé de préparation et dispositif électroluminescent. Selon la présente invention, une série de matériaux TADF bleus foncés avec un rendement élevé et un PLQY élevé sont synthétisés au moyen d'une conception moléculaire ingénieuse. Le matériau TADF bleu foncé a un rendement élevé et est synthétisé par des étapes simples. De plus, le matériau TADF bleu foncé est utilisé en tant qu'objet d'une couche luminescente du dispositif électroluminescent, une série de dispositifs électroluminescents ayant une luminance élevée, une efficacité de production élevée et une longue durée de vie sont développés.
PCT/CN2019/103503 2019-05-24 2019-08-30 Matériau à fluorescence retardée bleu foncé à activation thermique, son procédé de préparation et dispositif électroluminescent WO2020237885A1 (fr)

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