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Phenanthrene series derivatives and organic light-emitting diode containing the same

A derivative and organic technology, applied in the field of organic light-emitting diodes, can solve the problem that the energy gap is not enough to be used as organic phosphorescent molecules, and achieve the effects of improving carrier transport speed, best electroluminescent efficiency, and wide applicability

Inactive Publication Date: 2008-07-02
IND TECH RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the energy gaps of the materials disclosed in the above patents are not sufficient to be used as the matrix of organic phosphorescent molecules

Method used

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  • Phenanthrene series derivatives and organic light-emitting diode containing the same
  • Phenanthrene series derivatives and organic light-emitting diode containing the same
  • Phenanthrene series derivatives and organic light-emitting diode containing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Synthesis of compound 1:

[0068] 9,10: 9,10-bis(trimethylene)-9,10-dihydrophenanthrene (9,10:9,10-bis(trimethylene)-9,10-dihydrophenanthrene)

[0069] First, reactant 1 is prepared, and the reaction formula is as follows:

[0070]

[0071] Mix 2 grams 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-dione and 4 grams of 1,3-acetonedicarboxylate (diethyl1,3-acetonedicarboxylate) (manufactured by ACROS, 95%), and maintain at 60°C . After 36 hours of reaction, 10% HCl aqueous solution was added to neutralize the precipitate and filter. The collected precipitate was dissolved in acetic acid, and then 300 ml of 10% HCl aqueous solution was added, and the reaction was heated for 18 hours. The acetic acid and water were removed, neutralized with sodium bicarbonate aqueous solution, and separated by precipitation and filtration to obtain the product of reactant 1 with a yield of 17%.

[0072] Next, compoun...

Embodiment 2

[0077] Synthesis of compound 2:

[0078] 9,10: 9,10-bis(trimethylene)-2,7-dibromo-9,10-dihydrophenanthrene (9,10:9,10-bis(trimethylene)-2,7-dibromo-9 , 10-dihydrophenanthrene)

[0079] The synthesis reaction formula is as follows:

[0080]

[0081] 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), stirred at room temperature for three hours to obtain compound 2 as a white crystalline solid product, with a yield of 75%.

[0082] Measured for compound 2 1 H NMR(CDCl 3 ) The spectral data are as follows: δ(ppm) 1.44~1.48(m,2H), 1.57~1.65(m,2H), 1.92~1.99(m,4H), 2.10~2.16(m,4H), 7.31~7.33(d , 2H), 7.48 (s, 2H), 7.68-7.70 (d, 2H).

Embodiment 3

[0084] Synthesis of compound 3:

[0085] 9,10: 9,10-bis(trimethylene)-2,7-biscarbazole-9,10-dihydrophenanthrene (9,10:9,10-bis(trimethylene)2,7-biscarbazole-9 , 10-dihydrophenanthrene)

[0086] The synthesis reaction formula is as follows:

[0087]

[0088] Under nitrogen, 0.4 g of carbazole (manufactured by Aldrich, 96%) and 0.5 g of compound 2 were dissolved in 40 ml of o-xylene solvent, and 0.005 g of palladium (II) acetate (Palladium(II) acetate) was added. (Manufactured by Aldrich, 98%) catalyst, 0.32 g of sodium t-Butoxide (manufactured by Aldrich, 97%) and tri-tert-butyl phosphine (manufactured by Across, 99%) for reflux reaction In 12 hours, compound 3 was obtained as a white solid with a yield of 90%. This compound 3 is a novel phenanthrene derivative of the present invention.

[0089] Compound 3 measured 1H NMR(400MHz, CDCl 3 ) The spectral data are as follows: δ (ppm) 1.58-1.64 (m, 2H), 1.69-1.75 (m, 2H), 2.15-2.23 (m, 4H), 2.22-2.29 (m, 4H), 7.30-7.33 (t , 4H), 7.44-...

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Abstract

The invention relates to phenanthrene derivatives that have a structure in formula (I) and formula (II), wherein, A is respectively selected from hetero atoms of nitrogen, silicon, oxygen, phosphor and boric and B is respectively selected from phenyl, naphthyl, phenanthreny base, anthracene base, pyrenyl, heterocyclic radical, polycyclic aromatic base and polycyclic heterocyclic radical that at least have a conjugate base. The phenanthrene derivatives of the invention can effectively prevent aggregation among molecules and can improve the injection efficiency of the carriers (electron / cavity) of components and promote photopeak efficiency when being taken as maternal luminous compound of an organic electroluminescence diode.

Description

Technical field [0001] The invention relates to a novel phenanthrene series derivative and an organic light emitting diode containing the phenanthrene series derivative as a light-emitting material. Background technique [0002] The molecular materials used in organic light-emitting diodes (OLED), organic electroluminescence (EL) components, or photovoltaic components are conjugated molecules in structure, and the molecular structure is formed by the interaction of single and double bonds. Has SP 2 Hybrid orbitals, so the structure is easier to become a plane; and the unpaired electrons of the PZ orbital on the carbon atom form π-π * Unlocalized conjugated bonds, electrons can be transferred in the form of single-bond double-bond resonance to achieve the purpose of conduction. This kind of conjugated molecule has an energy gap (E) between the highest occupied molecular orbital (HOMO) occupied by electrons and the lowest unoccupied molecular orbital (LUMO) occupied by electrons. g...

Claims

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Application Information

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IPC IPC(8): C07D209/82C07C211/61C07C211/54C07C211/57C07F7/08H01L51/50H01L51/54
Inventor 段启圣邓宛容陈亮年王汝雯郑煜芬徐幸铃
Owner IND TECH RES INST
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