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Derivatives of naphthalene benzofuran and anthracene, preparation method, application and device thereof

A technology of naphthalene benzofuran and its derivatives, applied in the field of organic photoelectric materials, can solve the problems of lifespan not meeting commercial needs, low glass transition temperature, low electron mobility, etc., and achieve high-efficiency luminescence and high glass transition temperature , the effect of high quantum efficiency

Active Publication Date: 2020-06-09
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Blue-light materials can be divided into fluorescent and phosphorescent systems. At present, the efficiency of phosphorescent devices is higher than that of fluorescent devices, but the efficiency roll-off is very serious, and the service life cannot meet commercial needs. In order to improve device efficiency more effectively, the material itself requires higher requirements. Excellent quantum efficiency, good thermal stability and film-forming properties, and suitable electron mobility, which facilitates the balance of carrier recombination and light emission
[0005] Anthracycline has an aromatic structure with a high degree of conjugation. Many blue light materials use anthracene as the center, but there are disadvantages such as low glass transition temperature, poor film-forming property, and low electron mobility.

Method used

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  • Derivatives of naphthalene benzofuran and anthracene, preparation method, application and device thereof
  • Derivatives of naphthalene benzofuran and anthracene, preparation method, application and device thereof
  • Derivatives of naphthalene benzofuran and anthracene, preparation method, application and device thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The preparation method of compound 2 of the present invention, the method comprises the following four steps:

[0048] (1) 2.22g of 9-anthraceneboronic acid and 2.58g of 2-bromo-1,1'-biphenyl were fed according to the molar ratio of 1 to 1.1, adding an appropriate amount of tetrahydrofuran and 60ml of 2mol / L potassium carbonate solution, ultrasonically removed the air, and added Tetrakis(triphenylphosphine)palladium 50 mg was reacted under nitrogen protection for 12 hours. After cooling to room temperature, extract 3 times with dichloromethane, wash 3 times with water, dry over anhydrous magnesium sulfate for 2 hours, distill off the solvent under reduced pressure, and recrystallize to obtain 9-([2-1,1'-biphenyl] Base) anthracene 2.64g, yield 80%.

[0049] (2) Under the condition of nitrogen protection, in a 1000mL single-necked bottle, add 3.3g of 9-([2-1,1'-biphenyl]yl)anthracene, 50mL of anhydrous chloroform to promote dissolution, and then add 100mL of N,N -Dimeth...

Embodiment 2

[0053] The preparation method of compound 5 of the present invention, the method comprises the following steps:

[0054] 10-(2-[1,1'-biphenyl]yl)9-anthracenylboronic acid 3.7g and 2-bromo-5a,11a-dihydronaphthalene[2,3-b]benzofuran 2.7g according to the molar ratio 1. 1 to 1 feeding, add an appropriate amount of tetrahydrofuran and 2mol / L potassium carbonate solution 30ml, ultrasonically remove the air, add tetrakis (triphenylphosphine) palladium 50mg, react under nitrogen protection for 12 hours. After cooling to room temperature, extract with dichloromethane 3 times, wash with water 3 times, dry over anhydrous magnesium sulfate for 2 hours, distill off the solvent under reduced pressure, recrystallize with dichloromethane and n-hexane, and finally obtain 3.5 g of white compound 5 , yield 72%. MS(APCI)(m / z):[M+H + ] Calculated to get 549.21; actual measurement, 549.21. Elemental analysis calculated to get C 42 h 28 O: C, 91.94; H, 5.14; O, 2.92 Found: C, 91.89; H, 5.16; O,...

Embodiment 3

[0056] The preparation method of compound 8 of the present invention, the method comprises the following steps:

[0057] 10-(2-[1,1'-biphenyl]yl)9-anthracenylboronic acid 3.7g and 3-bromo-5a,11a-dihydronaphthalene[2,3-b]benzofuran 2.7g according to the molar ratio 1. 1 to 1 feeding, add an appropriate amount of tetrahydrofuran and 2mol / L potassium carbonate solution 30ml, ultrasonically remove the air, add tetrakis (triphenylphosphine) palladium 50mg, react under nitrogen protection for 12 hours. After cooling to room temperature, extract 3 times with dichloromethane, wash 3 times with water, dry over anhydrous magnesium sulfate for 2 hours, distill off the solvent under reduced pressure, recrystallize with dichloromethane and n-hexane, and finally obtain 3.2 g of white compound 8 , yield 64%. MS(APCI)(m / z):[M+H + ] Calculated to get 549.21; actual measurement, 549.21. Elemental analysis calculated to get C 42 h 28 O: C, 91.94; H, 5.14; O, 2.92 Found: C, 91.91; H, 5.15; O,...

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Abstract

The invention belongs to the field of applied science and technology of organic photoelectric materials, and in particular relates to derivatives of naphthalene benzofuran and anthracene and their preparation methods, applications and devices. The derivatives of naphthalene benzofuran and anthracene provided by the present invention take naphthalene benzofuran and anthracene as basic structural units, can be used as the main material of the blue fluorescent light-emitting layer, and have good performance. At the same time, its synthetic route is simple and easy. As a blue fluorescent material, it has a high glass transition temperature, high quantum efficiency, good electron transport ability, good film-forming property and stable properties. In blue light devices, it shows high luminous efficiency and stability, which is an ideal blue fluorescent material.

Description

technical field [0001] The invention belongs to the field of applied science and technology of organic photoelectric materials, and in particular relates to derivatives of naphthalene benzofuran and anthracene and their preparation methods, applications and devices. Background technique [0002] Organic electroluminescent devices (OLEDs) have become more and more commercialized. As the next generation of displays, they have the following characteristics: low driving voltage, fast response, ultra-thin devices, wide luminous viewing angle, light weight and luminous brightness, and can be made into flexible devices, easy to use. Realize large-area display. [0003] In order to realize OLED full-color display, blue light material, as one of the three primary colors, can realize efficient and stable blue light emission, and as the main material, green light and red light can be obtained through energy transfer. At present, Blu-ray materials are still the bottleneck. [0004] Bl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/77C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D307/77C09K2211/1011C09K2211/1007C09K2211/1088H10K85/615H10K85/6574H10K50/11
Inventor 穆广园庄少卿
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD