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Organic electroluminescent material, preparation method and applications thereof

An electroluminescent material and electroluminescent technology, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve problems such as poor spectral color purity, achieve good current efficiency, low lighting voltage, and reduced lighting voltage Effect

Active Publication Date: 2015-03-11
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fluorescent devices emit light in a singlet state, while phosphorescent devices emit light in a triplet state. Due to different light-emitting mechanisms, phosphorescent devices usually have higher luminous efficiency. However, as blue phosphorescent devices, due to the lower triplet energy, so The spectral color purity is usually poor. The blue phosphorescent devices that have been reported so far are mainly sky blue light, and there are few reports on dark blue light emitting devices.

Method used

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  • Organic electroluminescent material, preparation method and applications thereof
  • Organic electroluminescent material, preparation method and applications thereof
  • Organic electroluminescent material, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of compound 1

[0042]

[0043] In a 2L three-necked flask, add 2,6-dibromo-1,5 naphthyridine (80.6g, 0.28mol), 2-nitro-phenylboronic acid ester (154g, 0.62mol), K 2 CO 3 (138g, 1.0mol), toluene (800mL), absolute ethanol (120mL), deionized water (240mL), N 2 protection, adding Pd(PPh 3 ) 4 (8.4g, 0.0072mol), heat up to reflux, keep the temperature for 30h, cool down to room temperature, add 300mL deionized water to the reaction bottle, stir for 5min, separate liquid, wash the organic phase once with 300mL deionized water, collect the organic phase, Anhydrous Na 2 SO4 Dry, filter, remove the solvent, the crude product is purified by silica gel column chromatography, the eluent is ethyl acetate:petroleum ether=1:1, to obtain compound 1, the total weight is 88.2g, the yield is 84.6%, MS (m / s ): 372.3.

Embodiment 2

[0044] Embodiment 2: the preparation of compound 2

[0045]

[0046] In a 2L three-necked flask, add compound 1 (85.6g, 0.23mol), triphenylphosphine (262.2g, 1.0mol), 600mL o-dichlorobenzene, N 2 Protect, heat up to internal temperature 165-170°C, keep warm for 10h, stop heating, cool down to room temperature, remove solvent under reduced pressure, the obtained crude product is purified by silica gel column chromatography, and the eluent is petroleum ether: ethyl acetate = 1: 1. Further recrystallization using methyl ethyl ketone as a solvent to obtain compound 2, brown-yellow crystals, with a total weight of 54.0 g, a yield of 76.2%, and MS (m / s): 308.1.

Embodiment 3

[0047] Embodiment 3: the preparation of compound 3 and compound C01

[0048]

[0049] In a 500mL three-necked flask, add compound 2 (30.8g, 0.10mol), iodobenzene (22.4g, 0.11mol), cuprous iodide (1.9g, 0.01mol), potassium carbonate (27.5g, 0.2mol), DMF (280mL), under the protection of nitrogen, raise the temperature to an internal temperature of 110-115°C, keep it warm for 16 hours, then cool down to room temperature, slowly pour the reaction solution into 1L of deionized water, stir at room temperature for 1 hour, filter with suction, collect the filter cake, and remove it to 400L Wash with ionic water, suction filter, rinse with 100mL methanol, collect the solid, purify by silica gel column chromatography, gradient elution, eluent first use petroleum ether:ethyl acetate=3:1, collect compound C01, slightly yellow Solid 11.2g, yield 24%; then the eluent was replaced with petroleum ether: ethyl acetate = 1:1, compound 3 was collected, light brown solid 18.7g, yield 48.6%, MS...

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Abstract

The invention relates to an organic electroluminescent material, a preparation method and applications thereof. The material is an organic micromolecular material, which takes 1,5-naphthyridine as the center and has a parallel ring structure, and the structure of the material is represented in the description. In the structural formula, the Ar1 and Ar2 individually represent an aromatic ring with / without a substituent or an aromatic heterocyclic ring with / without a substituent, and further represent a benzene ring, naphthalene ring, pyridine, [1,8]naphthyridine, pyrimidine or triazine with / without a substituent, wherein the Ar1 and Ar2 can be same or different. The provided material has a proper molecular energy level and high glass-transition temperature, so the material can be used as a phosphorescent main material and can be used to prepare the functional layer and especially the luminescent layer of an organic electroluminescent device in the organic electroluminescent field.

Description

technical field [0001] The invention relates to an organic electroluminescence material, a preparation method and application thereof, and belongs to the field of organic electroluminescence. Background technique [0002] Organic electroluminescent diodes (OLEDs) were produced in the 1980s. OLED devices are self-luminous components. A variety of products based on OLED display technology have been industrialized. At present, OLED displays are gradually moving from small screens to large screens. A series of OLED products with brand-new visual impact are gradually realizing mass production. [0003] The basic structural unit of an OLED display is an OLED device, which can be divided into fluorescent devices and phosphorescent devices according to different light-emitting mechanisms. Fluorescent devices emit light in a singlet state, while phosphorescent devices emit light in a triplet state. Due to different light-emitting mechanisms, phosphorescent devices usually have highe...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D471/22C07D519/00H01L51/54
Inventor 盛磊高自良董鹏超巨成良张钊杨腾
Owner VALIANT CO LTD
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