Indenofluorene derivative containing pyrimidyl or pyrazinyl or triazinyl group, and its application

A technology of derivatives and compounds, applied in the field of new organic materials, can solve the problems of increasing the complexity of the device manufacturing process, reducing the cost of OLEDs, disadvantages, etc., and achieve good thermal stability, good film-forming performance, and high electron 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

Benefits of technology

This patented inventive compound described by this patents provides technical benefits such as excellent heat resistance, strong electric field effectiveness, ability for forming films on various substrates like plastics or paper, and being able to function well as both electronic transmission layers (ETL) and light emitting hosts within displays made from these polymers.

Problems solved by technology

This patented technical problem addressed in this patent relates to developing better electronic transport layers for organic light emitting diodes (EL displays) due to their superior hole conductivity compared to traditional methods like ammonia or chloride ion sources. Current EL display technology uses expensive rare metals, while current liquid crystal display technologies require complex processes involving multiple steps. There is thus a demand for more effective electron injectors and transistors suitable for future applications without increasing costs associated therefrom.

Method used

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  • Indenofluorene derivative containing pyrimidyl or pyrazinyl or triazinyl group, and its application
  • Indenofluorene derivative containing pyrimidyl or pyrazinyl or triazinyl group, and its application
  • Indenofluorene derivative containing pyrimidyl or pyrazinyl or triazinyl group, and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] The synthesis of embodiment 1 compound 1

[0096] (1) The first step

[0097]

[0098] Under the protection of Ar gas, 18.2 g of 2,4,6-trichloropyrimidine (molecular weight 182, 0.10 mol), 17.92 g of indenofluorene-2,7-diboronic acid (molecular weight 398, 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 reflux for 4 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 23.65 g of an intermediate with a molecular weight of 604 and a yield of 87%.

[0099] (2) The second step

[0100]

[0101] Und...

Embodiment 2

[0103] The synthesis of embodiment 2 compound 2

[0104] (1) The first step

[0105]

[0106] 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%.

[0107] (2) The second step

[0108]

[0109] Under the ...

Embodiment 3

[0111] The synthesis of embodiment 3 compound 3

[0112] (1) The first step

[0113]

[0114] 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 20 minutes and stirred for 1h. Then, 18.2g of 2,4,6-trichloropyrimidine (molecular weight 182, 0.1mol) dissolved in 180ml of DMF was added in 20 minutes, stirred for 3 hours, poured into 1000ml of water, filtered and dried in vacuum, and the product was washed with silica gel After column purification, 25.4 g of the target molecule (0.081 mol) was obtained with a molecular weight of 313 and a yield of 81%.

[0115] (2) The second step

[0116]

[0117] 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 (...

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Abstract

The invention provides a novel compound having a structure represented by formula (I). In the formula (I), R1 to R5 are respectively 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 heterocyclic rings, C4-C30 condensed heterocyclic aromatic hydrocarbons, C4-C30 arylamino groups or C4-C30 aryloxy groups; n is 1 or 2; A1 to A4 are N atoms or C atoms, A2 and A4 are the C atoms when the A1 and the A3 are the N atoms, or A2 and A3 are the C atoms when A1 and the A4 are the N atoms, or A1 and A3 are the C atoms when A2 and A4 are the N atoms, or A1 and A2 are the C atoms when A3 and A4 are the N atoms, or A2 is the C atom when A1, A3 and A4 are the N atoms; and L is a singly-bonded or C6-C10 aromatic ring or a C4-C10 N-containing heterocyclic ring. The compound is used in organic electroluminescent devices as an electron transfer layer material or a luminescent host material.

Description

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Claims

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Application Information

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Owner KUNSHAN VISIONOX DISPLAY TECH
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