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Sulfur-bridged quinazoline-based tetradentate platinum complex phosphorescent material and preparation method thereof

A technology of quinazolines and platinum complexes, applied in the direction of luminescent materials, platinum group organic compounds, platinum organic compounds, etc., can solve the problems of low quantum efficiency, improve luminous efficiency, reduce self-quenching phenomenon, improve Solubility effect

Active Publication Date: 2019-07-16
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Initially, the tetradentate platinum complex was connected to the ligand by nitrogen atom, although the blue shift effect of luminescence was achieved, but the quantum efficiency was low

Method used

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  • Sulfur-bridged quinazoline-based tetradentate platinum complex phosphorescent material and preparation method thereof
  • Sulfur-bridged quinazoline-based tetradentate platinum complex phosphorescent material and preparation method thereof
  • Sulfur-bridged quinazoline-based tetradentate platinum complex phosphorescent material and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of embodiment 1,2-(3-bromophenyl)-4-diphenylaminoquinazoline qba

[0030] Weigh 0.35g (1mmol) of 2-(3-bromophenyl)-4-chloroquinazoline, 0.08g (2mmol) of 60% sodium hydride, and 0.25g (1.5mmol) of diphenylamine in a two-necked bottle, and add Solvent dimethyl sulfoxide, react at 30°C for 10h. After the reaction was completed, the reaction solution was poured into water, a large amount of white precipitate was produced, suction filtered, column chromatography, separated by petroleum ether:ethyl acetate=20:1 developer chromatography, and 0.3g (0.67mmol) of white solid qba was obtained , the yield was 67%. 1H NMR (400MHz, CDCl3) δ7.93 (m, 8H), 7.46 (dd, J = 5.3, 3.2Hz, 4H), 7.12 (dd, J = 5.4, 3.1Hz, 4H), 5.84 (S, 2H) .

[0031]

Embodiment 2

[0032] Embodiment 2, the quinazoline S (qba) of ligand sulfur atom bridging 2 preparation of

[0033] Weigh 2-(3-bromophenyl)-4-diphenylaminoquinazoline qba 0.225g (0.5mmol), potassium phosphate 0.064g (0.3mmol), potassium thioacetate 0.029g (0.25mmol), bis( Dibenzylideneacetone)palladium 0.023g (0.025mmol), 1,1-bis(diphenylphosphino)ferrocene 0.02g (0.035mmol), add toluene 3ml, acetone 1.5ml mixed solvent under nitrogen protection, 110℃ Reaction 7h. After the reaction was completed, it was cooled to room temperature, extracted with dichloromethane, dried by adding anhydrous sodium sulfate, and separated by column chromatography with petroleum ether: ethyl acetate = 10:1 developer chromatography to obtain 0.1 g of white solid S(qba) 2 , the yield was 52%. 1H NMR (400MHz, CDCl3) δ = 8.38 (S, 2H), 8.11 (d, J = 7.6, 2H), 7.96 (d, J = 7.9, 2H), 7.65 (t, J = 7.7, 2H), 7.39 –7.28(m,17H),7.17(t,J=11.1,16H).

[0034]

Embodiment 3

[0035] Embodiment 3, complex S (qba) 2 Preparation of Pt

[0036] Weigh quinazoline S(qba) bridged by sulfur atom 2 0.077g (0.1mmol), 0.05g (0.1mmol) potassium tetrachloroplatinate, 4mg tetrabutylammonium bromide, 5ml acetic acid was added under nitrogen protection, stirred at room temperature for 12 hours, heated to 120°C for 70h. After the reaction was completed, cool to room temperature, add 15ml of deionized water, a precipitate precipitated out, filter with suction, dry, column chromatography, and use dichloromethane: ethyl acetate = 5:1 developer chromatography to obtain 0.032g orange-red solid S(qba) 2 Pt, 25% yield. 1H NMR (400MHz, CDCl3) δ=8.14–8.07(m,2H),7.47(t,J=7.7,4H),7.42–7.28(m,9H),7.09(t,J=7.6,1H),6.99 –6.93(m,2H).MALDI-TOF-MS(m / z):calcd for[M]+C 52 h 34 N 6 SPt: 969.37, found: 969.594.

[0037]

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PUM

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Abstract

The invention discloses a sulfur-bridged quinazoline-based tetradentate platinum complex phosphorescent material and a preparation method thereof. The phosphorescent material has a general structure represented by formulae (I) and (II) as shown in the specification. In the formulae, R can be one selected from the group consisting of phenyl, 4-fluoro-substituted phenyl, 2,4-difluoro-substituted phenyl, 3,4,5-trifluoro-substituted phenyl, 4-trifluoromethyl-substituted phenyl, 2-trifluoromethyl-substituted phenyl, 2,6-dimethyl-substituted phenyl, 4-methoxy-substituted phenyl, 4-nitro-substitutedphenyl, 4-N,N-dimethylamino-substituted phenyl, 2-benzothienyl, 2-benzofuryl, 9-(4-substituted phenyl)carbazole, 9-(4-substituted-phenyl)phenothiazine, 2-substituted 9,9-dimethylfluorenyl, tert-butoxy, 2,6-dimethyl-substituted phenoxy, hexahydropyridyl, N-carbazolyl, N-diphenylamino, N-bis(4-a tertiary butyl phenyl)amino, N-phenothiazinyl, 9,9-methylacridanyl radicals.

Description

technical field [0001] The invention relates to the technical field of electroluminescence, and is a kind of quinazoline tetradentate platinum complex phosphorescent material based on a sulfur bridge with a rigid structure. Background technique [0002] Organic light-emitting diodes (OLEDs) are widely used in flat panel displays, solid-state lighting and various fields because of their advantages such as self-illumination, bendability, thinness, high luminous efficiency and brightness, low driving voltage, full solid-state, and wide temperature range. in electronic equipment. At the same time, the demand for OLEDS functional materials, especially the light-emitting layer materials that play a decisive role in the efficiency and lifetime of OLEDs, is also growing rapidly. [0003] Blu-ray materials are indispensable in the fields of full-color display and lighting. On the one hand, blue-light materials can not only directly prepare three-color displays to achieve full-color ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06
CPCC07F15/0086C09K11/06C09K2211/185
Inventor 梅群波何颖张嘉威童碧海封雯雅刘磊
Owner NANJING UNIV OF POSTS & TELECOMM
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