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Substituted pyridine compound and application thereof

A compound, pyridine technology, applied in the field of substituted pyridine compounds, can solve the problems of phase separation of mixed host materials, complex device preparation, etc., achieve high triplet energy level and glass transition temperature, improve transport performance, and reduce conjugation degree Effect

Pending Publication Date: 2019-02-22
AAC TECH NANJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these two strategies complicate the fabrication of devices, and the mixed host materials cause phase separation problems.

Method used

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  • Substituted pyridine compound and application thereof
  • Substituted pyridine compound and application thereof
  • Substituted pyridine compound and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0102] The preparation methods of the compounds disclosed in the present invention are provided below. However, the present disclosure is not intended to be limited to any of the methods described herein. One skilled in the art can readily modify the described methods or utilize a different method to prepare one or more of the disclosed compounds. The following aspects are exemplary only, and are not intended to limit the scope of the present disclosure. Temperature, catalyst, concentration, reactant composition, and other process conditions may vary, and one skilled in the art of this disclosure can readily select appropriate reactants and conditions for a desired complex.

[0103] The meaning of the abbreviations in the embodiments of the present invention: PE: petroleum ether; DCM: dichloromethane; EA: ethyl acetate; DMSO-d6, deuterated dimethyl sulfoxide; CDCl3, deuterated chloroform; MeTHF: methyl tetrahydrofuran; Pb(dba) 2 : Tris(dibenzylideneacetone)dipalladium; S-Ph...

Embodiment 1

[0104] Embodiment 1: the synthesis of H-1 compound

[0105] Step 1: Synthesis of 9-(3-methyl-5-bromopyridin-2-yl)-9H-pyridin[2,3-b]indole

[0106] 9-(3-methyl-5-bromopyridin-2-yl)-9H-pyridin[2,3-b]indole is synthesized by the following reaction scheme 1:

[0107]

[0108] 2,5-dibromo-3-methylpyridine (2.51g, 10.0mmol), carboline (1.82g, 11.0mmol), CuI (381mg, 2.0mmol), 1-methylimidazole (246mg, 3.0mmol) , potassium carbonate (2.76g, 20.0mmol), and toluene (25mL) were placed in a 38mL sealed tube. After bubbling nitrogen for 5min, the temperature was raised to 120°C, and the reaction was refluxed for 48h. After the reaction was completed, filter and rinse the filter cake with ethyl acetate. The obtained filtrate was distilled under reduced pressure to remove the solvent, and then the resultant was purified through a silica gel column (petroleum ether: ethyl acetate = 10:1 → 5:1) to obtain a white solid 9-(3-methyl-5-bromo Pyridin-2-yl)-9H-pyridin[2,3-b]indole (1.75 g, 52%...

Embodiment 2

[0113] Embodiment 2: the synthesis of H-2 compound

[0114] The H-2 compound is synthesized by the following reaction formula 3

[0115]

[0116] 9-(3-methyl-5-bromopyridin-2-yl)-9H-pyridin[2,3-b]indole (109mg, 0.32mmol), 3,6-di-tert-butylcarbazole (99mg , 0.35mmol), Pb (dba) 2 (59mg, 0.06mmol), S-Phos (26mg, 0.06mmol), sodium tert-butoxide (61mg, 0.64mmol), and toluene (3mL) were placed in a 38mL sealed tube, heated to 120°C after nitrogen bubbling for 5min, and reacted Reflux for 28h. After the reaction was completed, it was filtered with celite, and the filter cake was rinsed with ethyl acetate. The obtained filtrate was evaporated under reduced pressure to remove the solvent, and then the resultant was purified by silica gel column (petroleum ether: ethyl acetate = 10:1) to obtain a light yellow solid (158 mg, yield 92%). 1 H-NMR (400MHz, DMSO-d 6 )δ: 8.86 (d, J = 2.7Hz, 1H), 8.71 (dd, J = 7.7, 1.6Hz, 1H), 8.48 (dd, J = 4.8, 1.6Hz, 1H), 8.42–8.38 (m, 1H ),8.38–8.3...

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Abstract

The invention belongs to the field of organic electroluminescent materials, and discloses a substituted pyridine compound and application thereof. The compound has a structure as shown in a general formula (I) in the specification, and can be used for improving the transmission performance of electrons and holes inside the compound by the embedded combination of a pyridine group and carbazole / carboline group; the angle between the pyridine linked substituted group and the pyridine group can be increased by introducing a steric hindrance group onto the pyridine substitute group, and the conjugated degree in molecules can be reduced, so that the compound has extremely high triplet level and glass temperature and is suitable for blue light and dark blue light main body materials.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, in particular to a substituted pyridine compound and its application. Background technique [0002] In the field of organic electroluminescent device technology, efficient and long-life luminescence can be achieved in different ways. For the light-emitting layer that emits a spectrum, one of the ways is to use host-guest doping to improve efficiency and life. [0003] In order to achieve high-efficiency luminescence, avoid the reverse energy transfer from the guest material to the host material, and confine the triplet excitons in the light-emitting layer, the triplet energy level of the host material should be greater than that of the dopant material. When the triplet energy level of the host material is smaller than the triplet energy of the dopant material, a reverse transition from the dopant material to the energy level of the host material will occur, resulting in a decre...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00C09K11/06H01L51/54
CPCC09K11/06C07D471/04C07D519/00C09K2211/1029C09K2211/1088C09K2211/1092H10K85/654H10K85/6572H10K85/6574H10K85/6576
Inventor 刘九州黄达马腾达曹辰辉陈少海
Owner AAC TECH NANJING
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