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Phenanthrene benzene derivative and polymer thereof, copolymer containing phenanthrene benzene derivative and luminous material composition

A technology of phenanthrene benzene derivatives and luminescent materials, which is applied in the field of new phenanthrene benzene derivatives. It can solve the problems of inability to reach deep luminescence wavelengths, poor light stability, and poor photoelectric efficiency, so as to improve photoelectric efficiency and prevent aggregation. , the effect of increasing stability

Active Publication Date: 2010-02-24
IND TECH RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] From the molecular structure disclosed in the patent, it can be seen that the core molecule with molecular steric barrier is a large hard molecule, and the two sides of the molecule are connected by triple bonds, so the solubility is not good
And because it is the main chain of benzene ring molecules connected by three bonds, the light stability is not good, and the electroluminescent wavelength will not reach the deep blue field (400 ~ 430nm) due to the long electron resonance.
However, if thiophene is used as the main molecule to connect benzene ring molecules with triple bonds, there will be a problem of poor photoelectric efficiency.

Method used

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  • Phenanthrene benzene derivative and polymer thereof, copolymer containing phenanthrene benzene derivative and luminous material composition
  • Phenanthrene benzene derivative and polymer thereof, copolymer containing phenanthrene benzene derivative and luminous material composition
  • Phenanthrene benzene derivative and polymer thereof, copolymer containing phenanthrene benzene derivative and luminous material composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] [Example 1] Synthetic compound 1

[0091] 9,10: 9,10-bis(cyclopentane)-9,10-dihydrophenanthrene

[0092] (9,10:9,10-bis(cyclopenta)-9,10-dihydrophenanthrene)

[0093] First prepare reactant 1, its reaction formula is as follows:

[0094]

[0095] Mix 2 g of NaOH with 200 ml of methanol and heat to 60°C. After the NaOH is completely dissolved, add 3 grams of phenanthrene-9,10-diketone and 4 grams of 1,3-acetone dicarboxylate (diethyl1,3-acetonedicarboxylate) (manufactured by ACROS, 95%), and maintain 60°C . After reacting for 36 hours, 10% HCl aqueous solution was added to neutralize the precipitate and filter it. The collected precipitate was dissolved with acetic acid, and then 300 ml of 10% HCl aqueous solution was added, and the reaction was heated for 18 hours. Acetic acid and water were removed, neutralized with aqueous sodium bicarbonate solution, and the precipitate was separated by filtration to obtain the product of reactant 1 with a yield of 17%.

[0...

Embodiment 2

[0100] [Example 2] synthetic compound 2:

[0101] 9,10:9,10-bis(cyclopenta)-2,7-diboron-9,10-dihydrophenanthrene (9,10:9,10-bis(cyclopenta)-2,7-diboron- 9,10-dihydrophenanthrene)

[0102] Its synthetic reaction formula is as follows:

[0103]

[0104] Dissolve 2 grams of compound 1 in 20 ml of dichloromethane (DCM) solvent, then add 20 ml of acetic acid solvent, drop 3 grams of bromine water (Br 2 , manufactured by Lancaster Company), stirred at room temperature for three hours to obtain a white crystalline solid product with a yield of 75%.

[0105] Under nitrogen, 6.66 g of bis(4,4,5,5-tetramethyl-1,3,2 dioxyboron) (Bis(pinacolato)diboron) (manufactured by Boron molecular company) and 5 g of the above-mentioned white crystals were dissolved In 100ml of toluene (TEDIA) solvent, add 4.72 grams of potassium acetate (J.T, Baker, 98%) and 0.1 gram of dichloro[1,1'-bis(phenylphosphino)phenanthrene]palladium(II) dichloromethane Adduct (Dichloro[1,1'-bis(diphenylphosphino)fer...

Embodiment 3

[0106] [Example 3] synthetic compound 3:

[0107] Bromo-2-ethylhexyloxy-methylbenzene bromo-(2-ethylhexyloxy)-4-methylbenzene)

[0108] Its synthetic reaction formula is as follows:

[0109]

[0110] Get 17.5 grams of 2-bromo-4-methyl-phenol (2-bromo-4-methylphenol, 1eq, Alfa Aesar, 98%) in a three-neck reactor, add 250ml of acetone (acetone, J.T.Baker), feed nitrogen heating Stir at reflux. Add 26 g K 2 CO 3 (2eq, SHOWA) and 0.4 grams of 18-crown-6 (18-crown-6, 0.015eq., Lancaster, 99%), after 10 minutes, 23 grams of 2-ethylhexane bromide (1.2eq.Aldrich , 96%) reacted for 28 hrs and left to cool, filtered the filtrate, and removed most of the solvent with a rotary evaporator (rota-vapor). Extract with absolute ethanol (EA, Mallinckrodt Co.), NaOH (aq, Aldrich) and deionized water twice to remove ions, then add MgSO 4 (Aldrich), filter the filtrate to remove the solvent with a rotary evaporator, set up a vacuum distillation device, remove the remaining 2-ethyl hexane ...

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PUM

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Abstract

The invention relates to phenanthrene benzene derivatives with a structure of a formula (I), polymers thereof, copolymers containing the phenanthrene benzene derivatives and luminous material compositions, wherein R1, R2, R3 and R4 are independent substituted groups of alkyl or alkoxy with long chains. The phenanthrene benzene derivatives are co-synthesized by phenanthrene derivative molecules with stereo obstacles and benzene derivative molecules with high solubility, and can be copolymerized with other electrophilic or vugular conjugated molecules to form the copolymers of which energy gap is positioned between 1.8 and 3.0eV. The polymers of the phenanthrene benzene derivatives or the copolymers containing the phenanthrene benzene derivative can be doped with other luminous materials to form luminous materials emitting red, blue and green and full-color light.

Description

technical field [0001] The invention relates to a novel phenanthrene derivative and a luminescent material containing the polymer of the phenanthrene derivative. Background technique [0002] At present, the polymer electroluminescent diode (PLED) component has been gradually developed into one of the future light sources because of its simple product structure and component manufacturing process, and it is easy to make a large-area and flexible component. The light color stability and component life of PLEDs depend on the polymer materials used, and molecular aggregation is the main reason for the instability of PLED light color. At the same time, due to the requirements of the component manufacturing process, the polymer materials need to have good solubility. [0003] A novel molecular structure is disclosed in U.S. Patent No. 6967255, as follows: [0004] [0005] , which can be applied to the field of organic photoelectric materials, is the patent of the inventor of...

Claims

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Application Information

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IPC IPC(8): C07C43/205C07F5/02C08G61/02C08G61/12C09K11/06
Inventor 段启圣邓宛容黄坤源杜安邦王炳杰
Owner IND TECH RES INST
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