Thermal activation delayed fluorescence material containing 1, 10 phenanthroline unit and application of material

A technology for thermally activated delay and fluorescent materials, applied in luminescent materials, compounds of group 4/14 elements of the periodic table, organic chemistry, etc., can solve problems such as poor thermal stability, fast efficiency roll-off, high cost of electroluminescent device materials, etc. Problems, to achieve high energy utilization, high RISC rate, improve luminous efficiency and stability

Inactive Publication Date: 2016-08-17
WUHAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the problems of high material cost, poor thermal stability and fast efficiency roll-off of electroluminescent devices existing in existing thermally activated delayed fluorescent materials and thermally activated delayed fluorescent OLED devices, the present invention provides a thermally activated delayed fluorescent material and OLED devices prepared using this type of thermally activated delayed fluorescent material

Method used

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  • Thermal activation delayed fluorescence material containing 1, 10 phenanthroline unit and application of material
  • Thermal activation delayed fluorescence material containing 1, 10 phenanthroline unit and application of material
  • Thermal activation delayed fluorescence material containing 1, 10 phenanthroline unit and application of material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Preparation of 2,9-di-N-phenoxazinyl-1,10-phenanthroline

[0035]

[0036] 2,9-di-N-phenoxazinyl-1,10-phenanthroline

[0037] Add 1.3 g of phenoxazine, 240 mg of 70% oil-dispersed sodium hydride and 20 ml of tetrahydrofuran into a 50 ml single-necked round-bottom flask, reflux for 30 minutes under argon protection, and then add 0.75 g of 2,9-dichloro-1, 10 phenanthroline, then refluxed at 60 degrees Celsius for 24 hours, cooled to room temperature, quenched with saturated brine, extracted with dichloromethane, dried the organic phase with anhydrous sodium sulfate, filtered, and spin-dried. The product was passed through the column with methanol:dichloromethane volume ratio 1:20 to obtain 1.35 g of the product. Yellow-green solid, yield 83%. 1H NMR (CDCl 3 ,400MHz): δ[ppm]8.17(d,J=8Hz,2H),7.77(d,J=8Hz,4H),7.71(s,2H),7.65(d,J=8Hz,2H),6.96( d,J=4Hz,8H),6.88-6.84(m,4H).MS(EI):m / z 542.3[M] + .

Embodiment 2

[0038] Example 2: Preparation of 4,7-di-N-phenoxazinyl-1,10-phenanthroline

[0039]

[0040] 4,7-di-N-phenoxazinyl-1,10-phenanthroline

[0041] Add 1.30 g of phenoxazine, 240 mg of 70% oil-dispersed sodium hydride and 20 ml of tetrahydrofuran into a 50 ml single-necked round-bottomed flask, and add 0.75 g of 4,7-dichloro-1 after reflux for 30 minutes under argon protection. 10 phenanthroline, then refluxed at 60 degrees Celsius for 24 hours, cooled to room temperature, quenched with saturated brine, extracted with dichloromethane, dried the organic phase with anhydrous sodium sulfate, filtered, and spin-dried. The product was passed through the column at a volume ratio of methanol:dichloromethane of 1:30 to obtain 1.40 g of the product. Pale yellow solid, yield 86%. 1 H NMR (CDCl 3 ,400MHz): δ[ppm]9.47(d,J=8Hz,2H),8.07(s,2H),7.77(d,J=4Hz,2H),6.77(d,J=8Hz,4H),6.71- 6.67(m,4H),6.54-6.50(m,4H),5.73(d,J=8Hz,4H).MS(EI):m / z 542.4[M] + .Example 3: Preparation of 4,7-di-N-phen...

Embodiment 3

[0041] Add 1.30 g of phenoxazine, 240 mg of 70% oil-dispersed sodium hydride and 20 ml of tetrahydrofuran into a 50 ml single-necked round-bottomed flask, and add 0.75 g of 4,7-dichloro-1 after reflux for 30 minutes under argon protection. 10 phenanthroline, then refluxed at 60 degrees Celsius for 24 hours, cooled to room temperature, quenched with saturated brine, extracted with dichloromethane, dried the organic phase with anhydrous sodium sulfate, filtered, and spin-dried. The product was passed through the column at a volume ratio of methanol:dichloromethane of 1:30 to obtain 1.40 g of the product. Pale yellow solid, yield 86%. 1 H NMR (CDCl 3 ,400MHz): δ[ppm]9.47(d,J=8Hz,2H),8.07(s,2H),7.77(d,J=4Hz,2H),6.77(d,J=8Hz,4H),6.71- 6.67(m,4H),6.54-6.50(m,4H),5.73(d,J=8Hz,4H).MS(EI):m / z 542.4[M] + .Example 3: Preparation of 4,7-di-N-phenothiazinyl-1,10-phenanthroline

[0042]

[0043] 4,7-di-N-phenothiazinyl-1,10-phenanthroline

[0044] Add 1.41 g of phenothiazine, 240 mg...

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Abstract

The invention provides a thermally-induced delayed fluorescence material and a preparation method of an organic electroluminescent device. The preparation method includes: using 1, 10 phenanthroline which is rigid as a strong-pull electron centronucleus and a diphenylamine derivative with high electron donating capability as a peripheral connecting group to form a D-A-D strong charge transfer state compound, wherein R1, R2 R3, R4, R5, R6, R7 and R8 are one of aromatic diphenylamine derivatives. The thermal activation delayed fluorescence material is simple to prepare and suitable for wide application. An organic compound obtained by the material can serve as a luminous layer material in OLEDs, and luminous efficiency and stability of the electroluminescent device can be improved by doping proper main materials.

Description

technical field [0001] The invention relates to a thermally activated delayed fluorescent material and an OLED device prepared by using the thermally activated delayed fluorescent material. In particular, it relates to a thermally activated delayed fluorescent material with phenanthroline as the central core and an OLED device prepared by using the thermally activated delayed fluorescent material. Background technique [0002] Compared with inorganic semiconductor materials, organic semiconductor materials have lower preparation cost, better controllability and excellent optoelectronic properties. Organic light-emitting diodes (OLEDs) have great potential in the application of optoelectronic devices in display and lighting. [0003] Photoelectric conversion efficiency is an important parameter for evaluating OLEDs. Since the advent of organic light-emitting diodes, in order to improve the luminous efficiency of organic light-emitting diodes, various light-emitting material s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07F7/10C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D471/04C07F7/0816C09K2211/104C09K2211/1033C09K2211/1037C09K2211/1029H10K85/6572H10K85/657H10K50/00
Inventor 杨楚罗吴凯龙龚少龙詹丽斯
Owner WUHAN UNIV
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