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Preparation method for metal coordinated polymer long-life luminescent material and application

A compound and metal salt technology, which is applied in the field of metal coordination polymer long-life luminescent materials and its preparation, can solve the problems of high price, environmental pollution, and limited storage of rare heavy metals

Inactive Publication Date: 2019-04-12
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although phosphorescent materials have achieved a leap in brightness and efficiency and accelerated the process of industrialization and practical application of organic electroluminescence technology, these rare heavy metals such as Pt and Ir have very limited storage capacity, are expensive, pollute the environment, and are in the process of realizing high The performance of blue light, especially the relatively deep blue light emitting materials, still has a big technical bottleneck

Method used

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  • Preparation method for metal coordinated polymer long-life luminescent material and application
  • Preparation method for metal coordinated polymer long-life luminescent material and application
  • Preparation method for metal coordinated polymer long-life luminescent material and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] Synthesis of Example 1 Compound L1 (5,10-bis(pyridin-4-yl)-5,10-dihydrophenazine)

[0113]

[0114] Under nitrogen protection, 5,10-dihydrophenazine (0.92g, 5mmol), 4-bromopyridine (1.9g, 12mmol), Pd(OAc) 2 (68mg, 0.3mmol), t-BuONa (3.46g, 36mmol), [(t-Bu) 3 PH]BF 4 (262mg, 0.9mmol) and toluene (50mL) were stirred at 110°C for 16 hours. After cooling to room temperature, water (100 mL) was added. layered. The aqueous phase was extracted with DCM (3 x 50 mL), the combined organic phases were dried over anhydrous sodium sulfate, filtered and the solvent was removed. Using dichloromethane as eluent, pass Al 2 o 3 The residue was purified by column chromatography to obtain the product L1 as a green solid (0.82 g, 48.7%), and its hydrogen and carbon spectra were as follows: figure 1 , 2 As shown, the CIE diagram is shown as Figure 12 As shown, the fluorescence emission pattern of PL (photoluminescence) is shown as Figure 13 shown.

[0115] 1 H NMR (400MHz,...

Embodiment 2

[0116] Synthesis of Example 2 Compound L2 (10,10'-bis(pyridin-3-yl)-10H,10'H-9,9'-spiroacridine)

[0117]

[0118] Under nitrogen protection, 10H, 10'H-9,9'-spiroacridine (1.04g, 3mmol), 3-bromopyridine (1.26g, 8mmol), Pd(OAc) 2 (68mg, 0.3mmol) mixture, add t-BuONa (3.46g, 36mmol), [(t-Bu) 3 PH]BF 4 (262mg, 0.9mmol) and toluene (50mL) were stirred at 110°C for 16 hours. After cooling to room temperature, water (100 mL) was added, the layers were separated, the aqueous phase was extracted with DCM (3 x 50 mL), the combined organic phases were dried over sodium sulfate, filtered and the solvent was removed. The residue was purified by silica gel column chromatography, using dichloromethane: acetone (v / v=10:1) as eluent to obtain white solid product L2 (1.06g, 70.6%), and its hydrogen and carbon spectra were as follows: image 3 , 4 As shown, the CIE diagram is shown as Figure 12 As shown, the fluorescence emission pattern of PL (photoluminescence) is shown as Figure...

Embodiment 3

[0120] Example 3 Compound R-1 (i.e. 4,4'-(10H,10'H-9,9'-spirobis[acridine]-10,10'-diyl)diphenylcarbaline Acid methyl ester) synthesis

[0121]

[0122] Under nitrogen protection, 10H, 10H'-9,9-spiroacridine (1mmol, 0.34g), methyl 4-bromobenzoate (3mmol, 0.65g), cesium carbonate (5mmol, 1.64g), palladium acetate ( 0.13mmol, 30mg) was placed in a 100mL three-necked bottle, 50mL of anhydrous toluene was added, and 1.2mL (0.41mmol) (tBu) was injected into the syringe 3 P, stirred at 110°C for 24h. After cooling to room temperature, the whole system was poured into 100 mL of water, and the layers were separated. Extract with dichloromethane (3 x 50 mL), combine the organic phases, dry over anhydrous magnesium sulfate, and filter. The solvent was removed under reduced pressure, and silica gel column chromatography (CH 2 Cl 2 ) to obtain white solid 0.4g, productive rate is 65%, and its hydrogen spectrum, carbon spectrum are as Figure 5 , 6 shown.

[0123] 1 H NMR (400M...

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Abstract

The invention provides a metal coordinated polymer material capable of rapidly transmitting phosphorescence, a preparation method for the metal coordinated polymer material and an application of the metal coordinated polymer material. According to the material, a compound represented by a formula (I) shown in the description is a ligand compound, wherein X, Y and Z each is independently selected from N and C; ~Q-R2 is selected from a formula shown in the description and a formula shown in the description; when the ~Q-R2 is the formula shown in the description, the structure is directly connected with the Z; when the ~Q-R2 is the formula shown in the description, the structure is connected with the Z through a single bond; R1 is selected from H, -COOH and -COOCH3; R2 is selected from H, a formula shown in the description and a formula shown in the description; and R3 is selected from -COOH and -COOCH3. The invention provides a series of efficient novel D-A long-life luminescent materials, novel ways of think and novel methods for material synthesis of efficient novel D-A long-life luminescent devices are provided, and a new breakthrough for achieving further development of full-color display and solid-state luminescence is found.

Description

technical field [0001] The invention relates to the field of novel phosphorescent materials and new OLED materials for photoelectric display, in particular to a metal coordination polymer long-life luminescent material and its preparation method and application. Background technique [0002] In the past two decades, polymers (CPs) or metal-organic frameworks (MOFs) have attracted considerable interest due to their diversity, remarkable structural properties, multifunctionality, and applications in gas storage, separation, catalysis, sensing, display, and in optical Many applications in equipment and other fields have received great attention. In these fields, functionalized organic-inorganic hybrid materials can accomplish the multifunctional synergy of inorganic linkers and organic ligands. Compared with noble metal-based light-emitting coordination polymers, such as Os(II), Ir(III), and Pt(II), copper(I) coordination polymers show attractive photoluminescent properties. ...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D471/10C08G83/00C09K11/06C07F1/08C07F3/08C07F1/10
CPCC07B2200/07C07B2200/13C07D401/14C07D471/10C07F1/005C07F3/003C08G83/008C09K11/06C09K2211/188
Inventor 耿琰李岗元朱福成任秀辉张凯宁董育斌
Owner SHANDONG NORMAL UNIV
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