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A kind of benzanthracene derivative containing pyrimidine or pyrazine or triazine group and its application

A derivative, benzanthracene technology, applied in the field of new organic materials, can solve the problems of difficult film formation and molecular crystallization, etc., and achieve the effects of increased film formation, good film formation and good thermal stability

Active Publication Date: 2015-10-07
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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  • A kind of benzanthracene derivative containing pyrimidine or pyrazine or triazine group and its application
  • A kind of benzanthracene derivative containing pyrimidine or pyrazine or triazine group and its application
  • A kind of benzanthracene derivative containing pyrimidine or pyrazine or triazine group and its application

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, in a 5000ml three-necked flask, 18.2g of 2,4,6-trichloropyrimidine (molecular weight 182, 0.10mol), 14.2g of benzanthracene-7,12-diboronic acid (molecular weight 316, 0.045 mol), tetrakis(triphenylphosphine) palladium 6.0g (0.0052mol), 600ml of THF, 400ml toluene, potassium carbonate 60g (0.435mol) dissolved in 400ml water to form a reaction flask. After repeated air exchange under reduced pressure, electric stirring was started, and the reaction was monitored by TLC (thin layer chromatography). After reflux for 5 hours, the reaction was complete. 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

...

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), THF 600ml, 400ml toluene, potassium carbonate 60g (0.435mol) dissolved in 400ml water to form a solution into the reaction flask. After repeated ventilation under reduced pressure, the electric stirring was started, and the reaction was monitored by TLC (thin layer chromatography). After reflux for 8 hours, the reaction was complete. 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 t...

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 DMF180ml, and a solution of 5.64g NaH (content 55%, 0.235mol) in 180ml DMF was added dropwise for 20min, stirred for 1h, and then Dissolve 18.2 g of 2,4,6-trichloropyrimidine (molecular weight 182, 0.1 mol) in 180 ml of DMF, add it in 20 min, stir for 3 h, pour into 1000 ml of water, filter the precipitate, and dry it in vacuum. The product is 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, in a 5000ml three-necked flask, add 15.6g (molecular weight 313, 0.05mol) of the reaction product of the previous step, 6.71g (molecular weight 122, 0.055mol) of phenylboronic acid, tetrakis (triphenylphosphine) palladiu...

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Abstract

The present invention provides a novel compound whose structure is represented by formula (I). Among them, R1 to R5 are independently selected from C1-C20 aliphatic alkyl groups or C6-C20 aromatic groups; Ar is selected from C4-C30 aromatic rings, C4-C30 N-containing heterocycles, and C4-C30 condensed Heterocyclic aromatic hydrocarbons, C4-C30 arylamino or C4-C30 aryloxy; n is 1 or 2; A1 to A4 are N atoms or C atoms; when A1 and A3 are N atoms at the same time, A2 and A4 are C atom; or, when A1 and A4 are N atoms at the same time, A2 and A3 are C atoms; or, when A2 and A4 are N atoms at the same time, A1 and A3 are C atoms; or, when A3 and A4 are N atoms at the same time A1 and A2 are C atoms; or, when A1, A3, and A4 are N atoms at the same time, A2 is a C atom; L is a single bond or a C6-C10 aromatic ring or a C4-C10 N-containing heterocycle. Such compounds are used as electron transport layer materials or light-emitting host materials in organic electroluminescent 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 Patents(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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