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Benzanthracene derivatives containing pyrimidinyl, pyrazinyl or triazinyl groups and applications thereof

A derivative, benzanthracene technology, applied in the field of new organic materials, can solve the problems of molecular formation crystallization and difficult film formation, and achieve the effects of increasing film formation, good film formation, and improving electron accepting ability and mobility.

Active Publication Date: 2014-02-12
KUNSHAN VISIONOX DISPLAY TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, if the condensed ring system is too large, it is easy to cause the molecules to form crystals and not easy to form a film.

Method used

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  • Benzanthracene derivatives containing pyrimidinyl, pyrazinyl or triazinyl groups and applications thereof
  • Benzanthracene derivatives containing pyrimidinyl, pyrazinyl or triazinyl groups and applications thereof
  • Benzanthracene derivatives containing pyrimidinyl, pyrazinyl or triazinyl groups and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] The synthesis of embodiment 1 compound 1

[0076] (1) The first step

[0077]

[0078] Under the protection of Ar gas, 18.2 g of 2,4,6-trichloropyrimidine (molecular weight 182, 0.10 mol), 14.2 g of benzanthracene-7,12-diboronic acid (molecular weight 316, 0.045 mol), tetrakis(triphenylphosphine) palladium 6.0g (0.0052mol), THF 600ml, toluene 400ml, potassium carbonate 60g (0.435mol) dissolved in 400ml water to form a solution into the reaction flask. After repeated ventilation under reduced pressure, start the electric stirring, monitor the reaction with TLC (thin layer chromatography), and the reaction is complete after refluxing for 5 hours. After cooling, the reaction system was divided into two layers. The organic layer was separated and evaporated to dryness to obtain a solid product, which was recrystallized with toluene to obtain 18.8 g of an intermediate with a molecular weight of 522 and a yield of 80%.

[0079] (2) The second step

[0080]

[0081] U...

Embodiment 2

[0083] The synthesis of embodiment 2 compound 2

[0084] (1) The first step

[0085]

[0086] Under the protection of Ar gas, 18.2 g of 2,4,6-trichloropyrimidine (molecular weight 182, 0.10 mol), 28.1 g of phenylboronic acid (molecular weight 122, 0.23 mol), tetrakis(triphenyl Phosphine) Palladium 12.0g (0.0104mol), 600ml of THF, 400ml of toluene, potassium carbonate 60g (0.435mol) dissolved in 400ml of water to form a solution into the reaction flask. After repeated ventilation under reduced pressure, start the electric stirring, monitor the reaction with TLC (thin layer chromatography), and the reaction is complete after reflux for 8 hours. After cooling, the reaction system was divided into two layers. The organic layer was separated and evaporated to dryness to obtain a solid product, which was recrystallized with toluene to obtain 19.9 g of an intermediate with a molecular weight of 266 and a yield of 75%.

[0087] (2) The second step

[0088]

[0089] Under the ...

Embodiment 3

[0091] The synthesis of embodiment 3 compound 3

[0092] (1) The first step

[0093]

[0094] Under the protection of Ar gas, carbazole 16.7g (molecular weight 167, 0.1mol) was dissolved in anhydrous DMF 180ml, a solution of 5.64g NaH (content 55%, 0.235mol) in 180ml DMF was added dropwise for 20min, stirred for 1h, and then 18.2g of 2,4,6-trichloropyrimidine (molecular weight 182, 0.1mol) dissolved in 180ml of DMF was added in 20min, stirred for 3h, poured into 1000ml of water, filtered and dried in vacuo, the product was purified by silica gel column, 25.4 g of the target molecule (0.081 mol) was obtained with a molecular weight of 313 and a yield of 81%.

[0095] (2) The second step

[0096]

[0097] Under the protection of Ar gas, add 15.6g of the reaction product of the previous step (molecular weight 313, 0.05mol), 6.71g of phenylboronic acid (molecular weight 122, 0.055mol), tetrakis (triphenylphosphine) palladium 3.0 g (0.0026mol), 150ml of THF, 100ml of tolue...

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Abstract

The invention provides a novel compound which is represented by the formula (I), wherein the R1 to R5 are independently selected from a C1-C20 aliphatic alkyl group or a C6-C20 aromatic group; the Ar is selected from: a C4-C30 aromatic ring, a C4-C30 N-containing heterocycle, a C4-C30 condensed heterocyclic aromatic hydrocarbon, a C4-C30 aromatic amino group, or a C4-C30 aromatic oxy group; n is 1 or 2; A1 to A4 represent N atoms or C atoms, when the A1 and A3 represent N atoms at the same time, the A2 and A4 represent C atoms; or when the A1 and A4 represent N atoms at the same time, the A2 and A3 represent C atoms; or when the A2 and A4 represent N atoms at the same time, the A1 and A3 represent C atoms; or when the A3 and A4 represent N atoms at the same time, the A1 and A2 represent C atoms; or when the A1, A3, and A 4 represent N atoms at the same time, the A2 represents a C atom; and L represents a single bond, or a C6-C10 aromatic ring, or a C4-C10 N-containing heterocycle. The compounds are used as an electron transmission layer material or a luminous main material in organic electroluminescence devices.

Description

technical field [0001] The invention relates to a novel organic material, in particular to a compound used for organic electroluminescent devices, a preparation method thereof and the application of the compound in the technical field of organic electroluminescent display. Background technique [0002] The electron transport material traditionally used in electroluminescent devices is Alq 3 , but Alq 3 The electron mobility is relatively low (about 10 -6 cm 2 / Vs). In order to improve the electron transport performance of electroluminescent devices, researchers have done a lot of exploratory research work. Yang Yang et al. used nano-scale cesium carbonate as electron transport and injection materials in electroluminescent devices, which improved the luminous efficiency of the devices (Advanced Functional Materials, 2007, 17, 1966–1973). Cao Yong and others synthesized FFF-Blm4 (J.Am.Chem.Soc.; (Communication); 2008; 130(11); 3282-3283.) as an electron transport and inje...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/26C07D403/14C07D239/42C07D241/12C07D241/20C07D251/24C07D251/22C09K11/06H01L51/54
CPCC09K11/06C07D239/26C07D239/42C07D241/12C07D241/20C07D251/18C07D251/22C07D251/24C07D403/14C09K2211/1059C09K2211/1044C09K2211/1029C09K2211/1011C09K2211/1007H10K85/622H10K85/636H10K85/654H10K85/6572
Inventor 邱勇李银奎段炼范洪涛任雪艳
Owner KUNSHAN VISIONOX DISPLAY TECH
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