Dicyanopyrazine-containing compound and application thereof in organic electroluminescent devices

A technology of dicyanopyrazine and compounds, applied to organic electroluminescent devices, in the field of compounds containing dicyanopyrazine, can solve different problems

Pending Publication Date: 2019-12-10
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Dicyanopyrazine-containing compound and application thereof in organic electroluminescent devices
  • Dicyanopyrazine-containing compound and application thereof in organic electroluminescent devices
  • Dicyanopyrazine-containing compound and application thereof in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0150] When Ar 1 、Ar 2 When not represented as a single bond, the intermediate boronic acid compound or Synthesis:

[0151]

[0152] (1) Under nitrogen atmosphere, weigh R 1 -H and Br-Ar 1 -Cl was dissolved in toluene, and then Pd 2 (dba) 3 Add tri-tert-butylphosphine, stir the mixture, then add sodium tert-butoxide, heat the mixed solution of the above reactants at a reaction temperature of 95-110°C for 10-24 hours, cool to room temperature after the reaction, and filter The reaction solution, the filtrate was rotary evaporated to no solvent, and passed through a neutral silica gel column to obtain the intermediate R 1 -Ar 1 -Cl; the Pd 2 (dba) 3 with R 1 The molar ratio of -H is 0.005~0.01:1, the tri-tert-butylphosphine and R 1 The molar ratio of -H is 0.005~0.02:1, the sodium tert-butoxide and R 1 The molar ratio of -H is 1.5~3.0:1;

[0153]

[0154] (2) Under a nitrogen atmosphere, weigh the intermediate R 1 -Ar 1 -Cl was dissolved in tetrahydrofura...

Embodiment 2

[0170] Embodiment 2: the synthesis of compound 1:

[0171]

[0172] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of raw material A, namely 5,6-dibromopyrazine-2,3-dicarbonitrile, 0.024mol of raw material D1, 150ml of toluene, stir and mix, and then add 0.06mol of tert-butyl Sodium alkoxide, 1 x 10 -4 molPd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, heated to 110°C, refluxed for 24 hours, sampling plate, showed that no raw material A remained, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C ), through a neutral silica gel column, to obtain the target product, HPLC purity 98.7%, yield 58.9%;

[0173] Elemental analysis structure (molecular formula C 48 h 32 N 6 ): theoretical value C, 83.21; H, 4.66; N, 12.13; test value: C, 83.25; H, 4.68; N, 12.10. ESI-MS(m / z)(M + ): The theoretical value is 692.27, and the measured value...

Embodiment 3

[0174] Embodiment 3: the synthesis of compound 5:

[0175]

[0176] 1) In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of raw material A, namely 5,6-dibromopyrazine-2,3-dinitrile, 0.012mol of raw material D1, 150ml of toluene, stir and mix, and then add 0.03mol Sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, heated to 110°C, refluxed for 24 hours, sampling plate, showed that no raw material A remained, and the reaction was complete; naturally cooled to room temperature, filtered, and the filtrate was subjected to vacuum rotary evaporation (-0.09MPa, 85°C ), through a neutral silica gel column to obtain intermediate M1, with a HPLC purity of 99.1% and a yield of 65.7%;

[0177] 2) In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of intermediate M1, 0.012mol of raw material D2, and 150ml of toluene, stir and mix, then add 0.03mol of sodium tert-butoxide, 5×10 -5 molPd 2 (dba) 3...

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Abstract

The invention discloses a dicyanopyrazine-containing compound and application thereof on organic light-emitting devices. The compound contains a dicyanopyrazine structure, has strong rigidity, and hasthe characteristics of difficult crystallization between molecules, difficult aggregation and good film-forming property after being connected with a carbazole derivative long-chain branch structure;the compound disclosed by the invention has double polarity, branched chains are electron-donating groups, and the HOMO energy levels of the material are different due to different electron-donatingcapacities of the groups, so that the compound can be used as different functional layer materials; in addition, the compound provided by the invention has a high triplet state energy level, can effectively block energy loss, and is beneficial to energy transfer, therefore, after the compound is applied to OLED devices as an organic electroluminescent functional layer material, the current efficiency, the power efficiency and the external quantum efficiency of the devices are greatly improved; and meanwhile, the service life of the devices is obviously prolonged.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing dicyanopyrazine and its application in organic electroluminescent devices. 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. 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 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 light-emitting device, and the positive a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D519/00C07D401/14C07D413/14H01L51/50H01L51/54
CPCC07D403/14C07D519/00C07D401/14C07D413/14H10K85/654H10K85/657H10K85/6572H10K50/11
Inventor 蔡啸张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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