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4-aryl pyrimidine or 4-heterocyclic aryl pyrimidine compound luminescent material and preparation method thereof

A technology of heterocyclic arylpyrimidine and arylpyrimidine, which is applied in the field of optoelectronic materials and can solve the problems that the efficiency cannot reach flexible large-area display screens

Active Publication Date: 2011-10-05
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although more and more novel organic electroluminescent materials have been developed and applied to organic electroluminescent devices, including small molecules and polymers, and their performance has been continuously improved, their efficiency still cannot reach the real high-efficiency flexible large-area Display, improving the luminous efficiency and service life of materials is still the key

Method used

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  • 4-aryl pyrimidine or 4-heterocyclic aryl pyrimidine compound luminescent material and preparation method thereof
  • 4-aryl pyrimidine or 4-heterocyclic aryl pyrimidine compound luminescent material and preparation method thereof
  • 4-aryl pyrimidine or 4-heterocyclic aryl pyrimidine compound luminescent material and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 2.3730g (10mmol) 3-acetyl-N-ethylcarbazole, 1.5416g (20mmol) ammonium acetate and 0.1363g (1mmol) zinc chloride to the two-neck flask, seal the device and protect the reaction system with nitrogen. Inject 5ml (30mmol) of triethyl orthoformate and 10ml (94mmol) of toluene under the protection of nitrogen. The reaction mixture was heated to 100 °C and stirring was continued at this temperature for 24 h. After cooling to room temperature, slowly add saturated sodium carbonate solution, stir for 30 min, and extract with dichloromethane. The organic phase was collected and dried with anhydrous sodium sulfate, concentrated, and separated by column chromatography. The obtained white solid was 4-pyrimidine luminescent material substituted with N-ethylcarbazole (ECzPM), and the yield was 20.5%. 1 HNMR (400MHz, CDCl 3 ): δ9.27(s, 1H), 8.90(s, 1H), 8.72-8.71(d, 1H), 8.22-8.18(t, 2H), 7.81-7.80(d, 1H), 7.54-7.43(m , 3H), 7.32-7.28 (m, 3H), 4.41-4.36 (q, 2H), 1.48-1.46 (t, 3H...

Embodiment 2

[0030] Add 1.3950g (5mmol) 3,6-diacetyl-N-ethylcarbazole, 1.9270g (25mmol) ammonium acetate and 0.2045g (1.5mmol) zinc chloride to the two-necked flask, seal the device and protect the reaction system with nitrogen . Under nitrogen protection, 5ml (46mmol) of trimethyl orthoformate and 12ml (113mmol) of toluene were injected. The reaction mixture was heated to 95 °C and stirring was continued at this temperature for 12 h. After cooling to room temperature, slowly add saturated sodium carbonate solution, stir for 40 min, and extract with dichloromethane. The organic phase was collected and dried with anhydrous sodium sulfate, concentrated, and separated by column chromatography. The obtained white solid was N-ethylcarbazole-substituted bis-4-pyrimidine luminescent material (ECzDPM), with a yield of 14.5%. 1 H NMR (400MHz, CDCl 3 ): δ9.27(s, 2H), 8.97(s, 2H), 8.75-8.74(d, 2H), 8.28-8.25(d, 2H), 7.83-7.82(d, 2H), 7.52-7.50(d , 2H), 4.44-4.39 (q, 2H), 1.51-1.47 (m, 3H). 13 C ...

Embodiment 3

[0032] Add 2.6900g (10mmol) of 3-acetyl-N-ethylphenothiazine, 2.3124g (30mmol) of ammonium acetate and 0.6818g (5mmol) of zinc chloride into the two-necked flask, seal the device and protect the reaction system with nitrogen. Inject 10ml (60mmol) of triethyl orthoformate and 5ml (47mmol) of toluene under the protection of nitrogen. The reaction mixture was heated to 120 °C, and stirring was continued at this temperature for 72 h. After cooling to room temperature, slowly add saturated sodium carbonate solution, stir for 20 min, and extract with dichloromethane. The organic phase was collected and dried with anhydrous sodium sulfate, concentrated, and separated by column chromatography. The obtained yellow viscous material was 4-pyrimidine luminescent material (EPzPM) substituted with N-ethylphenothiazine, and the yield was 13.5%. 1 H NMR (400MHz, CDCl 3 ): δ9.19(s, 1H), 8.70-8.69(d, 1H), 7.92-7.89(d, 1H), 7.85(s, 1H), 7.62-7.60(d, 1H), 7.18-7.12(m , 2H), 6.96-6.88 (m, 3H), ...

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Abstract

The invention relates to a 4-aryl pyrimidine or 4-heterocyclic aryl pyrimidine compound luminescent material and a preparation method thereof, and the structure can be represented as general formula (1), general formula (2), general formula (3), or general formula (4), wherein Ar represents an aryl group, a substituted aryl group, a heterocyclic aryl group, and a substituted heterocyclic aryl group. The method of the invention allows an acetyl-containing aryl or heterocyclic aryl compound to react with trimethyl orthoformate and ammonium acetate through a three-component coupling reaction under the action of a catalyst by using a one-pot method so as to obtain a series of aryl or heterocyclic aryl-containing 4-substituted pyrimidine compounds. The luminescent material of the invention has good dissolvability, film forming ability and stability, has high internal quantum efficiency, has a fluorescence emmission spectrum which can be adjusted from blue light to yellow light, can be used independently as a luminescent material, is expected to become a host material with excellent performance, and has important significance in the development of panel display devices with superior performance.

Description

technical field [0001] The invention relates to a luminescent material and belongs to the technical field of photoelectric materials. Specifically, it relates to a kind of luminescent material of 4-aryl pyrimidine or 4-heterocyclic aryl pyrimidine compound and a preparation method thereof. Background technique [0002] With the rapid development of information technology, new, efficient, and lightweight flexible organic electroluminescent displays (OLEDs) have attracted more and more attention, and have become one of the research focuses at home and abroad in recent years. This kind of flexible large-area display must have properties such as self-illumination, wide viewing angle, fast response time, high brightness, low operating voltage, full color, wide temperature range, and simple preparation. The requirements are almost harsh. The light-emitting materials used in organic electroluminescent devices not only require the materials to have good stability, good film-formin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04C07D403/14C07D417/04C07D417/14C07D239/26C09K11/06
Inventor 凌启淡黄维梅群波翁洁娜
Owner NANJING UNIV OF POSTS & TELECOMM
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