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Anthraquinone organic electroluminescent material, and preparation method and application thereof

A luminescent, anthraquinone-based technology, applied in the field of anthraquinone-based organic electroluminescent materials and their preparation, can solve the problems of efficiency roll-off, low S1 state radiation transition rate, difficult high exciton utilization rate and high fluorescence radiation efficiency and other problems, to achieve the effects of reducing efficiency roll-off, good industrialization prospects, improving exciton utilization and high fluorescence radiation efficiency

Active Publication Date: 2017-05-31
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although theoretically TADF materials can achieve 100% exciton utilization, there are actually the following problems: (1) The T1 and S1 states of the designed molecules have strong CT characteristics, and the very small S1-T1 state energy gap, although it can A high T1→S1 state exciton conversion rate is achieved through the TADF process, but at the same time it leads to a low S1 state radiative transition rate. Therefore, it is difficult to achieve both (or simultaneously) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) even Doped devices have been used to alleviate the T-exciton concentration quenching effect, and most devices made of TADF materials have a serious efficiency roll-off at high current densities

Method used

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  • Anthraquinone organic electroluminescent material, and preparation method and application thereof
  • Anthraquinone organic electroluminescent material, and preparation method and application thereof
  • Anthraquinone organic electroluminescent material, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1 Preparation of intermediate M1

[0055]

[0056] A 1000ml three-necked flask, in an atmosphere of nitrogen, add 0.02mol (7.28g) 2,3-dibromoanthraquinone, 0.02mol (2.44g) phenylboronic acid, 0.06mol (6.36g) sodium carbonate, 2×10 -4mol(0.14g)Pd(PPh 3 ) 2 Cl 2 , 360ml of toluene, 360ml of H2O, heating and refluxing for 6 hours, sampling point plate, the reaction is complete; natural cooling, liquid separation, the organic phase is washed once with 300ml of water, the organic phases are combined, and the organic phase is spin-dried to obtain 7.0g of brown solid; Add 140g of toluene to the solid and beat it at 50°C for 1h; filter, the target product 2-bromo-3-phenylanthraquinone 6.12g, purity 99.1%, yield 85%;

[0057] Take another 500mL three-necked flask, add 0.01mol (3.61g) 2-bromo-3-phenylanthraquinone, 0.01mol (2.00g) p-bromophenylboronic acid, 0.03mol (4.14g) potassium carbonate under a nitrogen atmosphere , 1×10-5mol(0.012g)Pd(PPh 3 ) 4 , 200mL of toluene, 150m...

Embodiment 2

[0060] Example 2 Preparation of intermediate M2

[0061]

[0062] The preparation method of intermediate M2 is the same as that of M1, except that 4-biphenylboronic acid is used instead of phenylboronic acid.

[0063] Elemental analysis structure (molecular formula C 32 H 19 BrO 2 ): Theoretical value C, 74.57; H, 3.72; Br, 15.50; O, 6.21; Test value: C, 74.77; H, 3.81; O, 6.15;

[0064] HPLC-MS: The theoretical value of the material is 514.06, and the actual value is 514.25.

Embodiment 3

[0065] Example 3 Preparation of intermediate M3

[0066]

[0067] The preparation method of intermediate M3 is the same as that of M1, except that 9-phenanthrene boronic acid is used instead of phenylboronic acid.

[0068] Elemental analysis structure (molecular formula C 34 H 19 BrO 2 ): Theoretical value C, 75.70; H, 3.55; Br, 14.81; O, 5.93; Test value: C, 75.50; H, 3.66; O, 5.94;

[0069] HPLC-MS: The theoretical value of the material is 538.06, and the actual value is 538.25.

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Abstract

The invention discloses an anthraquinone organic electroluminescent material, and a preparation method and application thereof. The organic electroluminescent material uses anthraquinone as the parent nucleus, and the structural formula is disclosed in the specification. In the anthraquinone organic electroluminescent material disclosed by the invention, HOMO and LUMO energy level electron clouds can be effectively separated, thereby implementing the smaller S1-T1-state energy gap, effectively enhancing the exciton utilization ratio and high fluorescent radiation efficiency, and lowering the efficiency roll-off under high current density. When the anthraquinone organic electroluminescent material is used for manufacturing OLED (organic light-emitting diode) light-emitting devices, the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved. The anthraquinone organic electroluminescent material disclosed by the invention has favorable application effects in OLED light-emitting devices, and has favorable industrialization prospects.

Description

Technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an anthraquinone organic electroluminescent material, and a preparation method and application thereof. Background technique [0002] Organic Light Emission Diodes (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products as well as new lighting products. It is expected to replace the existing liquid crystal display and fluorescent lighting, and has a broad application prospect. [0003] The OLED light-emitting device is 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 purpose 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 light-emitting device, and the positive an...

Claims

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Application Information

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IPC IPC(8): C07D265/38C07D265/34C07D279/22C07D279/14C07D219/02C07D221/18C07D241/46C07D241/38C07D491/048C07D495/04C07D471/04C07D498/04C07D513/04C07D487/04C07D491/056C07D517/04C07D209/94C09K11/06H01L51/54
CPCC09K11/06C07D209/94C07D219/02C07D221/18C07D241/38C07D241/46C07D265/34C07D265/38C07D279/14C07D279/22C07D471/04C07D487/04C07D491/048C07D491/056C07D495/04C07D498/04C07D513/04C07D517/04C09K2211/1096C09K2211/1092C09K2211/1088C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1029H10K85/657H10K85/6572
Inventor 石宇王岩胡葆华王兵邢宗仁李彩霞
Owner VALIANT CO LTD