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Organic compound based on pyridine and quinoxaline and application thereof

An organic compound and azabenzene technology, applied in the field of organic compounds and its application in OLED, can solve the problems affecting the angular distribution of OLED radiation spectrum and complex manufacturing process, etc.

Inactive Publication Date: 2018-01-26
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first two structures will affect the angular distribution of the radiation spectrum of the OLED. The third structure has a complicated manufacturing process, but the use of a surface covering layer has a simple process and increases the luminous efficiency by more than 30%, which has attracted widespread attention.

Method used

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  • Organic compound based on pyridine and quinoxaline and application thereof
  • Organic compound based on pyridine and quinoxaline and application thereof
  • Organic compound based on pyridine and quinoxaline and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1: the synthesis of intermediate I

[0074] Taking the synthesis of intermediate A1 as an example

[0075]

[0076] In a 250mL three-necked flask, blow nitrogen gas, add 0.04mol raw material 2,3-dibromo-5,6-dichloropyrazine, 100ml THF, 0.1mol phenylboronic acid, 0.0008mol tetrakis(triphenylphosphine)palladium, Stir, then add 0.12mol of K 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 5 hours, sampled and plated, the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain intermediate A1 with a HPLC purity of 99.7% and a yield of 87.2%.

[0077] Elemental analysis structure (molecular formula C 16 h 10 Cl 2 N 2 ): theoretical value C, 63.81; H, 3.35; Cl, ​​23.54; N, 9.30; test value: C, 63.79; H, 3.34; Cl, ​​23.55; N, 9.32. ESI-MS(m / z)(M + ): The theoretical value is 300.02, ...

Embodiment 2

[0086] Embodiment 2: the synthesis of intermediate II

[0087] Take the synthesis of intermediate B1 as an example

[0088]

[0089] In a 250mL three-necked flask, nitrogen gas was introduced, and 0.02mol of intermediate A6, 100ml of THF, 0.03mol of (4-(9-H-carbazol-9-yl)phenyl)boronic acid, and 0.0004mol of tetrakis(triphenyl) Phosphine) palladium, stir, then add the K of 0.06mol 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 5 hours, sampled and plated, the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain intermediate B1 with a HPLC purity of 99.4% and a yield of 75.3%.

[0090] Elemental analysis structure (molecular formula C 34 h 22 ClN 3 ): theoretical value C, 80.38; H, 4.36; Cl, ​​6.98; N, 8.27; test value: C, 80.41; H, 4.35; Cl, ​​6.99; N, 8.25. ESI-MS(m / z)(M + ): The theoretic...

Embodiment 3

[0095] Embodiment 3: intermediate Synthesis

[0096] When R 1 When expressed as a structure of general formula (5),

[0097]

[0098] (1) Under a nitrogen atmosphere, weigh 2,3-dibromoquinoxaline and dissolve it in tetrahydrofuran, and then Ar 5 -B(OH) 2 And tetrakis (triphenylphosphine) palladium is added, the mixture is stirred, and then saturated potassium carbonate aqueous solution is added, and the mixed solution of the above reactants is heated and refluxed at a reaction temperature of 70-90°C for 10-20 hours; after the reaction is completed, cool and mix The liquid was extracted with dichloromethane, the extract was dried with anhydrous sodium sulfate, and concentrated under reduced pressure, and the concentrated solid was purified by silica gel column to obtain compound intermediate M;

[0099]

[0100] (2) Under a nitrogen atmosphere, weigh the intermediate M and dissolve it in N,N-dimethylformamide (DMF), then add bis(pinacolyl)diboron, (1,1'-bis(diphenyl ...

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Abstract

The invention relates to an organic compound based on pyridine and quinoxaline and application thereof on an OLED device. The compound provided by the invention has relatively high glass transition temperature and molecular thermostability, and is low in absorption and high in refractive index in the field of visible light. When the organic compound is applied to a CPL layer of the OLED device, the light extraction efficiency of the OLED device can be effectively improved; the compound provided by the invention also has deep HOMO energy level and high electron mobility, can be used as a hole blocking / electron transport layer material of the OLED device, and can effectively block the transfer of holes or energy from a light-emitting layer to one side of an electron layer, thereby improvingthe recombination efficiency of the holes and electrons in the light-emitting layer, further improving the light-emitting efficiency of the OLED device and prolonging the service life of the OLED device.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound based on azabenzene and quinoxaline and its application in OLED. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and new lighting products, and is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. OLED light-emitting devices mostly adopt a sandwich structure, that is, the organic layer is sandwiched between the electrodes on both sides. Holes and electrons are injected from the anode and cathode respectively, and transported in the organic layer, and form excitons after meeting, and the excitons recombine to emit light. [0003] At present, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size appl...

Claims

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Application Information

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IPC IPC(8): C07D241/42C07D401/14C07D403/14C07D403/10C07D471/04C07D405/14C09K11/06H01L51/52H01L51/54
Inventor 王芳张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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