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Aggregation-induced room-temperature phosphorescent orange-red electroluminescent compound and preparation method and application thereof

A room-temperature phosphorescence and orange-red technology, which is applied in the field of aggregation-induced room-temperature phosphorescence orange-red electroluminescent compounds and their preparation, can solve problems such as device efficiency reduction, electroluminescent spectrum blue shift, and restrictions on commercial production, and achieve production High efficiency, strong stability, simple method and easy operation

Inactive Publication Date: 2020-05-08
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In organic electroluminescent devices (OLEDs), the molecular packing of the light-emitting layer molecules in the solid state leads to a decrease in the efficiency of the device, so the molecules are usually dispersed in the host material to suppress emission quenching and exciton annihilation to face the well-known fast in OLED devices. Efficiency rolls down. In the commercial production process, batch devices cannot be guaranteed because of the precise control of doping concentration. At the same time, the electroluminescence spectrum of doped devices undergoes a significant blue shift with the decrease of doping concentration. Therefore restricts commercial production

Method used

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  • Aggregation-induced room-temperature phosphorescent orange-red electroluminescent compound and preparation method and application thereof
  • Aggregation-induced room-temperature phosphorescent orange-red electroluminescent compound and preparation method and application thereof
  • Aggregation-induced room-temperature phosphorescent orange-red electroluminescent compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The general formula of the aggregation-induced room temperature phosphorescence orange-red organic light-emitting material prepared in this example is shown in formula I, and the representative compound is shown in formula II, wherein specific compounds are used as examples: 6-(4-([1, 1'-diphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)-2-(2'-methyl-[1,1': 3',1"-terphenyl]-5'-yl)-1H-benzisoquinoline-1,3-dione, whose molecular formula is C 64 h 46 N 2 o 2 , the structural formula is:

[0045]

[0046] Concrete preparation steps are as follows:

[0047]

[0048] 1. Preparation of precursor 2,6-diphenyl-4-aminotoluene

[0049] Under the protection of argon, 3g of 2,6-dibromo-4-nitrotoluene, 3g of sodium tetraphenyl boride, 8g of potassium carbonate, 0.3g of tetrabutylammonium bromide and 0.030g of palladium chloride were mixed and placed in In 20 mL of anhydrous acetone, stir overnight in an oil bath at 55°C. After the reaction was finished, the soluti...

Embodiment 2

[0055] The aggregation-induced room temperature phosphorescence orange-red organic light-emitting material 6-(4-(9H-carbazolyl-9-yl)phenyl)-2-(4-(tert-butyl)phenyl)-1H prepared in this example - Benzisoquinoline-1,3-dione, whose molecular formula is C 40 h 30 N 2 o 2 , the structural formula is:

[0056]

[0057] The preparation method comprises the following steps:

[0058]

Embodiment 3

[0060] Aggregation-induced room temperature phosphorescence orange-red organic luminescent material 6-(4-([1,1'-diphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino )phenyl)-2-(2'-methyl-[1,1':3',1"-terphenyl]-5'-yl)-1H-benzisoquinoline-1,3-dione Prepare the non-doped electroluminescent device A as the light-emitting layer material, and the specific steps are as follows:

[0061] 1. Clean the ITO glass in an organic solvent, dry it with nitrogen, and expose it to an ultraviolet-ozone atmosphere for 30 minutes.

[0062] 2. At 4.0 x 10 –4 Under the vacuum degree of Pa, the materials of the hole blocking layer, the hole transport layer, the light-emitting layer and the electron transport layer are sequentially evaporated at a rate of 0.1nm / s, and finally LiF / Al is used as the cathode. The structure of the device is as follows: ITO|HATCN(20nm)|TAPC(40nm)|luminescent material 7(20nm)|TMPYPB(40nm)|LiF(1nm)|Al(150nm), see Figure 6 . Among them, TAPC is 4,4'-cyclohexylbis[N,N-bis(4-...

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Abstract

The invention discloses an aggregation-induced room-temperature phosphorescent orange-red electroluminescent compound and a preparation method and application thereof. The invention belongs to the field of organic electroluminescence, and relates to a compound which is an organic molecule with aggregation-induced emission (AIE) and room-temperature phosphorescence (RTP), and has a structure shownas a formula I. In the formula I, R1 is H, alkyl, alkoxy, phenyl or carbazole, R2 is H, methyl, methoxyl, phenyl or tert-butyl, and R3 or R4 is phenyl, 9, 9-dimethylfluorenyl, naphthyl or biphenyl. The preparation method comprises the following steps: preparing a donor unit N-aryl precursor, and connecting donor N-aryl units through a C-4 site of naphthalene anhydride to form an orange light molecule with D-A configuration. The service life of the molecule at room temperature is 9.09 microseconds, and the molecule belongs to room-temperature phosphorescent molecules (RTP). A doped OLED deviceprepared by taking the material as a luminescent material has orange emission, the maximum external quantum efficiency is 8.74%, and the material is a multifunctional luminescent material with excellent performance.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to an orange-red electroluminescence compound induced by room-temperature phosphorescence in an aggregation state and a preparation method and application thereof. Background technique [0002] Traditional luminescent materials have strong emission intensity and high quantum yield in dilute solution. In organic electroluminescent devices (OLEDs), the molecular packing of the light-emitting layer molecules in the solid state leads to a decrease in the efficiency of the device, so the molecules are usually dispersed in the host material to suppress emission quenching and exciton annihilation to face the well-known fast in OLED devices. Efficiency rolls down. In the commercial production process, batch devices cannot be guaranteed because of the precise control of doping concentration. At the same time, the electroluminescence spectrum of doped devices undergoes a s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C07D401/10C09K11/06H01L51/50H01L51/54
CPCC07D221/14C07D401/10C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029H10K85/615H10K85/631H10K85/633H10K85/6572H10K50/11
Inventor 陈硕彭争春蒋月曾鹏举林鹏举
Owner SHENZHEN UNIV
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