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Fluorene and spiro-fluorene substituted phenylpyridine iridium complex and preparation method and application thereof

A technology of phenylpyridine iridium and phenylpyridine, which is applied in the field of organic electroluminescent materials, can solve the problems of short phosphorescence lifetime and high quantum efficiency, and achieve the effects of low cost, easy synthesis, and reduced concentration quenching

Inactive Publication Date: 2011-02-16
EAST CHINA NORMAL UNIV
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  • Abstract
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Problems solved by technology

Among them, metal iridium complexes are an important and widely studied organic electrophosphorescent material ([1] M.A.Baldo, S.Lamansky, P.E.Burrows, M.E.Thompon.S.R.Forrest.Appl.Phys.Lett.1999.75.4. [2] A. Tsuboyama, H. Iwawaki, M. Furugori, T. Mukaide, J. Kamatani, S. Igawa. T. Moriyama, S. Miura, T. Takiguchi. S. Okada, M. Hoshino, K. Ueno .J.Am.Chem.Soc.2003, 125, 12971.), due to the relatively short phosphorescence lifetime of metal iridium complexes, high quantum efficiency

Method used

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  • Fluorene and spiro-fluorene substituted phenylpyridine iridium complex and preparation method and application thereof
  • Fluorene and spiro-fluorene substituted phenylpyridine iridium complex and preparation method and application thereof
  • Fluorene and spiro-fluorene substituted phenylpyridine iridium complex and preparation method and application thereof

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Experimental program
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Embodiment 1

[0016] 1. Preparation of bis-[5-(9,9-dihexylfluorene)-2-phenylpyridine]iridium (acetylacetonate) complex 6b

[0017] (1) Preparation of 2-bromoacetyl-9,9'-dihexylfluorene 2a

[0018] Under ice bath, bromoacetyl bromide (2.07ml, 23.91mmol) was added dropwise to hexylfluorene (8g, 23.91mmol) and AlCl 3 (3.83g, 28.69mmol) of CH 2 Cl 2 solution, stirred for 20 min, then placed at room temperature and stirred for 1-2 hours. Pour into an ice bath of hydrochloric acid and stir, CH 2 Cl 2 Extracted, washed with water, saturated with Na 2 CO 3 Aqueous solution washing, water washing, anhydrous MgSO 4 After drying and concentration under reduced pressure, the residue was subjected to column chromatography (DCM:PE=1:4) to obtain a yellow liquid. 1 H NMR (CDCl 3 , 500MHz) δ: 8.02(d, J=6.6Hz, 2H), 7.81(m, 2H), 7.40(d, J=7.5Hz, 3H), 4.58(s, 2H), 2.07-2.02(m, 4H ), 1.14-1.04(m, 12H), 0.79-0.77(m, 6H), 0.64-0.61(m, 4H). 13 C NMR (CDCl 3 ,125MHz)δ:191.23,152.07,151.25,146.96,139.43...

Embodiment 2

[0028] Preparation of Bis-[5-(9,9')-dihexylfluorene-2-(4-methoxyphenyl)pyridine]iridium(acetylacetonate) 6a

[0029] (1) Preparation of 4-methoxybenzoic hydrazide 1a

[0030] Add ethyl p-methoxybenzoate (11.4g), 85% hydrazine hydrate (25ml), methanol (35ml) successively in a 250ml flask, heat to reflux for 24 hours, cool to precipitate a white solid, filter, and recrystallize from a small amount of ethanol. Melting point: 139-141°C. 1 HNMR (CDCl 3 , 500MHz) δ: 9.61(s, 1H), 7.81(d, J=8.8Hz, 2H), 6.98(d, J=8.7Hz, 2H), 4.41(s, 2H), 3.79(s, 3H).

[0031] (2) Preparation of 3-(4-methoxyphenyl)-6-(9,9'-dihexylfluorene)-1,2,4-triazine 3a

[0032] In a 100ml flask, add p-methoxybenzohydrazide (3.00g, 18.04mmol), 2-bromoacetyl-9,9'-dihexylfluorene (4.11g, 9.02mmol), sodium acetate (0.88g, 10.82mmol) ), ethanol (35ml), acetic acid (15ml). Add to reflux for 24 hours, cool, CH 2 Cl 2 Extraction, washing with water, saturated NaHCO 3 Aqueous wash, water wash, MgSO 4 After drying a...

Embodiment 3

[0040] Preparation of Bis-(5-(2-spirobifluorenyl)-2-phenylpyridine)iridium(acetylacetonate) 6c

[0041] (1) Preparation of 2-bromoacetylspirobifluorene 2b

[0042] In a 250ml three-necked flask, spirobifluorene (12g, 37.97mmol) was added to AlCl 3 (6.08g, 45.57mmol) in the dry dichloromethane solution, under ice-bath stirring, the dichloromethane (20ml) solution of bromoacetyl bromide (7.66g, 37.97mmol) is slowly added dropwise in the three-necked flask, After stirring at room temperature for 10 hours, pour into an ice bath of hydrochloric acid and stir, CH 2 Cl 2 Extracted, washed with water, saturated with Na 2 CO 3 Aqueous wash, water wash, MgSO 4 After drying and concentration under reduced pressure, the residue was subjected to column chromatography (DCM:PE=2:3) to obtain 11.35 g of a white solid, yield (68.35%). Melting point: 175-177°C. 1 H NMR (CDCl 3 , 500MHz) δ: 8.04(d, J=8.1Hz, 1H), 7.91(d, J=8.1Hz, 2H), 7.87(d, J=7.7Hz, 2H), 7.41-7.36(m, 3H), 7.35(s, 1H), ...

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Abstract

The invention belongs to the field of organic electroluminescent materials and relates to a fluorene and spiro-fluorene substituted phenylpyridine iridium complex and a preparation method and application thereof. The preparation method comprises the following steps of: synthesizing various fluorene and spiro-fluorene substituted phenylpyridine iridium ligands; reacting the ligands with iridium(III) chloride hydrate (IrCl3.3H2O) to obtain a chlorine-bridged dimer intermediate; and reacting the intermediate with acetylacetone in a proper solvent to obtain the fluorene and spiro-fluorene substituted phenylpyridine iridium complex. The iridium complex can change types and positions of the substituent of phenyl in a bidentateligand, can adjust luminous wavelength in a certain range and can be widely applied in the field of organic electroluminescence.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials. Specifically, it relates to iridium complex molecular materials, especially a phenylpyridine iridium complex with fluorene and spirobifluorene as substituents, its preparation method and application. Background technique [0002] Organic electroluminescence materials and devices are the international frontier research field. At present, after years of hard work in the industry, organic electroluminescent materials have been commercialized in some lighting, backlight and other fields. The developed organic display devices have been applied in mobile phones, MP3, audio display panels, etc. Organic electroluminescent materials can be divided into fluorescent materials and phosphorescent materials according to different light emitting principles. Compared with fluorescent materials, phosphorescent materials can make full use of all energy forms including singlet and tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00H01L51/54C09K11/06
Inventor 刘乾才吴国洪
Owner EAST CHINA NORMAL UNIV
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