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Compound having spiro bond, material for luminescent coating formation and organic electroluminescence element including the same
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A compound and luminescent technology, which is applied in luminescent materials, electroluminescent light sources, electrical components, etc., can solve the problems of high driving voltage of components, less blue light-emitting materials, and poor luminescent performance
Inactive Publication Date: 2006-06-21
IDEMITSU KOSAN CO LTD
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Abstract
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Problems solved by technology
[0005] However, among these compounds, polymer-based materials have poor luminescent properties due to the presence of impurities or unreacted residues at the end of the polymer; There are still many problems, such as visible color tone changes due to thermal decomposition products.
Therefore, the status quo is that there are still relatively few blue light-emitting materials that provide high-reliability and stable components.
Method used
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Embodiment 1
[0159] Example 1 (synthesis of compound (A11))
[0160] The synthetic route of compound (A11) is shown below.
[0161]
[0162] Intermediate 11-1
[0163]
[0164] Intermediate 11-2
[0165]
[0166] Intermediate 11-3
[0167]
[0168] Intermediate 11-4
[0169]
[0170] Intermediate 11-5
[0171]
[0172] Compound (A11)
[0173] (1) Synthesis of intermediate 11-1
[0174] Add 3,5-dibromobenzene-1-boronic acid (5.0g, 17.9mmol), 9-iodoanthracene (6.53g, 21.5mmol), Pd(PPh 3 ) 4 (0.62g, 0.54mmol), replaced with argon. An aqueous solution (27 mL) of toluene (50 mL) and sodiumcarbonate (5.69 g, 53.7 mmol) was added thereto, and heated to reflux for 8 h. The reaction solution was extracted with toluene and concentrated under reduced pressure. The obtained solid was purified by silica gel column chro...
Embodiment 2
[0185] Embodiment 2 (synthesis of compound (A12))
[0186] The synthetic route of compound (A12) is as follows.
[0187]
[0188] Intermediate 12-1
[0189]
[0190] Intermediate 12-2
[0191]
[0192] Intermediate 12-3
[0193]
[0194] Intermediate 12-4
[0195]
[0196] Compound (A12)
[0197] (1) Synthesis of intermediate 12-1
[0198] Add 2-bromofluorene (10g, 40.8mmol), dimethyl sulfoxide (15mL), benzyltriethylammonium chloride (0.19g, 0.82mmol), α, α' -Dibromoxylene (10.8g, 40.8mmol), was added dropwise to 50wt% sodiumhydroxideaqueous solution (6.5mL) with stirring, and stirred at 80°C for 2d. Water (100 mL) and toluene (100 mL) were added to the reaction solution, the organic layer was separated, and the organic layer was dried over anhydrousmagnesiumsulfate. Concentrate under reduced pressure in an evaporator to obtain 9....
Embodiment 3
[0207] Embodiment 3 (synthesis of compound (A26))
[0208] The synthetic route of compound (A26) is as follows.
[0209]
[0210] Compound (A26)
[0211] (1) 1-(10-(spiro[dihydroindene-2,9'-fluorene-2'-yl]))anthracene-9-yl)-3,5-bis(spiro[dihydroindene-2, Synthesis of 9'-fluoren-2'-yl])benzene (Compound A26)
[0212] Except that 4-(2,2-diphenylvinyl) phenylboronic acid in embodiment 2(5) is replaced with intermediate 12-2 (0.39g, 1.26mmol), and embodiment 2(5) The same synthesis was carried out to obtain 0.80 g of compound (A26), with a yield of 72.5%. Obtain m / z=1052 (M + , 100), and calculate C 83 h 56 =1052 consistent, confirmed to be the target product.
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Abstract
The present invention provides a novel spiro bond-containing compound of a specific structure, a material for forming a luminous coating film containing an organic solvent solution containing the spiro bond-containing compound, and excellent heat resistance, high stability of a thin film constituting an element, and uniform emission. Blue light, even at low voltage, an organic electroluminescent element with high luminance and luminous rate, a spiro bond-containing compound for realizing it, and a material for forming a luminescent coating film, the organic electroluminescent element is composed of at least a light-emitting layer One or more organic thin-film layers are sandwiched between a pair of electrodes consisting of an anode and a cathode, and at least one of the organic thin-film layers is an organic electroluminescence device containing the aforementioned spiro bond-containing compound.
Description
technical field [0001] The present invention relates to a spirobond-containing compound, a material for forming a luminous coating film, and an organic electroluminescence device using the material, and particularly relates to an organic electroluminescent device having excellent heat resistance, high stability of a thin film constituting the device, uniform blue light emission, and an An organic electroluminescence element with high luminance and luminous efficiency even under voltage, and a spiro bond-containing compound and a material for forming a luminescent coating film to realize it. Background technique [0002] Organic electroluminescence element (hereinafter, electroluminescence is abbreviated as EL) is a self-luminous element, the principle of which is to use the recombination energy of holes injected from the anode and electrons injected from the cathode under the action of an external electric field to cause fluorescence Sexual substances glow. Since C.W.Tang e...
Claims
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Application Information
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