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A kind of compound based on monosubstituent acridine, preparation method and application thereof

A technology based on acridine and compound, applied in the field of organic optoelectronic materials, can solve the problems of insufficient triplet energy level of CBP, low glass transition temperature, affecting the application of CBP, etc., and achieve good industrialization prospects, improved device life, and device performance. excellent effect

Active Publication Date: 2019-04-30
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The application of organic light-emitting diodes (OLEDs) in flat-panel displays has attracted widespread attention from industry and academia. However, traditional organic fluorescent materials can only use 25% of the singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low. Low, the highest is 25%, and the internal quantum efficiency of phosphorescent devices can theoretically reach 100%. At present, commercialized OLED display panels, green and red parts, all use phosphorescent materials to achieve high-efficiency light emission
[0005] Due to the concentration quenching problem, the light-emitting layer of a phosphorescent device usually needs to be doped with a luminescent dye in other materials at a certain concentration. This organic substance that disperses the phosphorescent luminescent dye is called a phosphorescent host. Material, 4,4'-bis(9H-carbazole)-1,1'-biphenyl, referred to as CBP, is one of the most widely used phosphorescent host materials at present, CBP has a certain hole transport ability, and the device performance is excellent , but CBP also has the problem of insufficient triplet energy level and low glass transition temperature. The above deficiencies also affect the application of CBP to a certain extent.

Method used

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  • A kind of compound based on monosubstituent acridine, preparation method and application thereof
  • A kind of compound based on monosubstituent acridine, preparation method and application thereof
  • A kind of compound based on monosubstituent acridine, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Compound C01

[0050]

[0051]In a 250mL three-necked flask, under an atmosphere of nitrogen gas, add 9-bromoacridine (2.58g, 0.01mol), compound M1 (4.24g, 0.011mol), potassium carbonate (4.15g, 0.03mol), tetratriphenyl Palladium phosphine (0.12g, 0.1mmol), 18-C-6 (0.08g, 0.3mmol), 100mL toluene, 100mL water, heated to 80-85°C for 12 hours. Naturally cooled to room temperature, separated, the organic phase was washed with water until neutral, dried over anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated to obtain the crude product. Through column chromatography, the target product was obtained with a yield of 78%.

[0052] Elemental analysis structure (molecular formula C 31 h 20 N 2O ): theoretical value C, 85.30; H, 4.62; N, 6.42; O, 3.67. Test values: C, 85.31; H, 4.59; N, 6.44; O, 3.66.

[0053] HPLC-MS: material theoretical value 436.16, actual value 436.31.

Embodiment 2

[0054] Example 2 Compound C06

[0055]

[0056] 250mL there-necked flask, under nitrogen atmosphere, add 9-bromoacridine (2.58g, 0.01mol), compound M2 (4.96g, 0.011mol), potassium carbonate (4.15g, 0.03mol), tetratriphenyl Palladium phosphine (0.23g, 0.2mmol), 18-C-6 (0.08g, 0.3mmol), 100mL toluene, 100mL water, heated to 80-85°C for 12 hours. Naturally cooled to room temperature, separated, the organic phase was washed with water until neutral, dried over anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated to obtain the crude product. By column chromatography, the target product was obtained with a yield of 80%.

[0057] Elemental analysis structure (molecular formula C 35 h 22 N 2 S): theoretical value C, 83.64; H, 4.41; N, 5.57; S, 6.38. Test values: C, 83.66; H, 4.40; N, 5.59; S, 6.35.

[0058] HPLC-MS: material theoretical value 502.15, actual value 502.50.

Embodiment 3

[0059] Example 3 Compound C14

[0060]

[0061] 250mL there-necked flask, under nitrogen atmosphere, add 9-bromoacridine (2.58g, 0.01mol), compound M3 (5.89g, 0.011mol), potassium carbonate (4.15g, 0.03mol), tetratriphenyl Palladium phosphine (0.12g, 0.1mmol), 18-C-6 (0.08g, 0.3mmol), 100mL toluene, 100mL water, heated to 80-85°C for 12 hours. Naturally cooled to room temperature, separated, the organic phase was washed with water until neutral, dried over anhydrous sodium sulfate, filtered, and the filtrate was rotary evaporated to obtain the crude product. Through column chromatography, the target product was obtained with a yield of 76%.

[0062] Elemental analysis structure (molecular formula C 44 h 30 N 2 ): theoretical value C, 90.07; H, 5.15; N, 4.77; test value: C, 90.15; H, 5.12; N, 4.73.

[0063] HPLC-MS: Material theoretical value 586.24, actual value 586.39.

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Abstract

The invention discloses a compound based on a single substituent acridine, a preparation method and an application thereof, and belongs to the technical field of organic photoelectric materials. It has the structure shown in formula I: the invention also discloses the preparation method and application of the above compound. The compound of the present invention uses the single substituent acridine as the mother nucleus, and connects the aromatic heterocyclic group to form an asymmetric structure, thereby destroying the crystallinity of the molecule, avoiding the aggregation between molecules, and having good film-forming properties. At the same time, the electron transport unit and the hole transport unit are introduced to form a bipolar structure. This structural feature is conducive to improving the efficiency and life of the phosphorescent device.

Description

technical field [0001] The invention relates to a compound based on a single substituent acridine, a preparation method and an application thereof, and belongs to the technical field of organic photoelectric materials. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] Small-molecule OLED light-emitting devices are like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/10C07D417/10C07D219/02C07D401/10C07D491/048C07D495/04C07D471/04C07D498/04C07D487/04C07D513/04C07D491/056C07D517/04C07D491/14C09K11/06H01L51/54
CPCC09K11/06C07D219/02C07D401/10C07D413/10C07D417/10C07D471/04C07D487/04C07D491/048C07D491/056C07D491/14C07D495/04C07D498/04C07D513/04C07D517/04C09K2211/1092C09K2211/1096C09K2211/1088C09K2211/1029C09K2211/1044C09K2211/1037C09K2211/1033H10K85/6576H10K85/657H10K85/6572
Inventor 高宪鹏于琳宋涛胡葆华孙戈亮张鹏
Owner VALIANT CO LTD