Organic light-emitting material based on phenanthroimidazole derivatives and application of organic light-emitting material in electroluminescent device

A luminescent material, phenanthroimidazole technology, applied in the field of organic electroluminescence, can solve the problems of chemical instability, high price, large efficiency roll-off, etc., and achieve the effect of high efficiency, low roll-off, and high glass transition temperature

Inactive Publication Date: 2021-01-26
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, on the one hand, noble metals such as iridium and platinum are generally used as phosphorescent materials, which are expensive. On the other hand, for deep blue phosphorescent materials, there are still problems such as chemical instability and large efficiency roll-off of devices at high current densities. Therefore, the development of An OLED device that uses cheap and stable organic small molecule materials and can achieve high-efficiency light emission is extremely important

Method used

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  • Organic light-emitting material based on phenanthroimidazole derivatives and application of organic light-emitting material in electroluminescent device
  • Organic light-emitting material based on phenanthroimidazole derivatives and application of organic light-emitting material in electroluminescent device
  • Organic light-emitting material based on phenanthroimidazole derivatives and application of organic light-emitting material in electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The concrete preparation method of phenanthroimidazole intermediate is as follows:

[0061]

[0062] 2,7-dibromophenanthrenequinone (10mmol), R 1 -CHO (i.e. R 1 -1 to R 1 -10)(10mmol), R 2 -NH 2 (i.e. R 2 -1 to R 2 -25) (50mmol), ammonium acetate (40mmol), and acetic acid (50mL) were added into a three-necked flask, and heated to reflux in an oil bath at 130°C for 12h under nitrogen protection. The reaction was stopped, the reaction mixture was poured into distilled water, stirred and filtered, and the obtained gray filter cake was washed with water, glacial acetic acid and ethanol in sequence, and dried to obtain the p-bromo-substituted phenanthroimidazole intermediate.

[0063] The specific preparation method of carbon-carbon coupling compound is as follows

[0064] The phenanthroimidazole intermediate (3mmol) substituted by para-bromine, organoboronic acid (i.e. R 3 -1 to R 3 -58) (7mmol), potassium carbonate (24mmol), tetrakis (triphenylphosphine) pallad...

Embodiment 2～27

[0069] As in Example 1, different raw materials were used to prepare compounds 2-27.

Embodiment 28

[0071] The preparation of phenanthroimidazole intermediate is as in Example 1.

[0072] The concrete preparation method of carbon-nitrogen coupling compound is as follows

[0073] The phenanthroimidazole intermediate (3mmol) substituted by para bromine, aromatic amine (ie R 4 -1 to R 4 -21) (7mmol), cesium carbonate (24mmol), three (dibenzylideneacetone) dipalladium (0.1mmol), tri-tert-butylphosphine (0.1mmol), o-xylene (30mL) add in the there-necked flask, N 2 Under protection, heat and reflux in an oil bath at 130°C for 12 hours to stop the reaction, pour the reaction mixture into distilled water, extract with dichloromethane, concentrate and separate by column chromatography (silica gel, dichloromethane) to obtain the powdery target product

[0074] Taking compound 28 as an example to illustrate the specific details of the synthesis example: the phenanthrene imidazole intermediate (3 mmol) substituted by para-bromine, R 4 -3 (7mmol), cesium carbonate (24mmol), three (dib...

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Abstract

The invention discloses an organic light-emitting material based on phenanthroimidazole derivatives and application of the organic light-emitting material in an electroluminescent device, and belongsto the technical field of organic electroluminescence. The structural formula of the organic light-emitting material is shown as (I), and R1R4 are the same or different and are C1-C30 alkyl, C3-C10 naphthenic base, C6-C48 aryl, C2-C30 heteroaryl selected from one or more atoms of O, N, Se and S, and C6-C40 aromatic amino. The phenanthroimidazole derivative has the advantages of good bipolar transmission capability, excellent thermal stability, high glass transition temperature and good film-forming property. The derivative can be used in the field of organic electroluminescence, and an organiclight-emitting diode device prepared from the derivative has the advantages of low turn-on, low roll-off, high efficiency and the like, and is further used for preparing an organic light-emitting display, an organic light-emitting lighting source or a decorative light source.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to an organic luminescent material based on phenanthroimidazole derivatives and its application in electroluminescent devices. Background technique [0002] In 1963, Pope et al. of New York University discovered for the first time that hundreds of volts were applied to organic aromatic anthracene crystals, and the weak blue light emission of anthracene could be observed (see M.Pope, H.Kallmann and P.Magnante, J.Chem Phys., 1963, 38, 2042). However, due to the high driving voltage and low luminous efficiency, it was not taken seriously at that time. Until 1987, C.W.Tang of Kodak used vacuum evaporation for the first time, using 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC) as the hole transporter. layer, tris(8-hydroxyquinoline)aluminum (AlQ 3 ) as the electron transport layer and light-emitting layer, a double-layer device was prepared,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C07D401/14C07D403/04C07D403/10C07D403/14C07D413/04C07D413/14C07D417/14C09K11/06H01L51/54H01L51/50
CPCC07D235/02C07D403/14C07D401/14C07D417/14C07D413/14C07D403/10C07D403/04C07D413/04C09K11/06C09K2211/1044C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037H10K85/626H10K85/636H10K85/631H10K85/657H10K85/6572H10K50/11
Inventor 李成龙王悦刘宇
Owner JILIN UNIV
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