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Bisindenophenoxazine organic electroluminescence materials and application thereof

A phenoxazine and electroluminescence technology, applied in the fields of luminescent materials, organic chemistry, circuits, etc., can solve problems such as the reduction of quantum efficiency, and achieve the effect of enhanced conjugation effect, good film stability, and difficulty in crystallization

Inactive Publication Date: 2016-09-14
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, the phenoxazine molecule has a non-planar structure, which is significantly different from the planar carbazole molecule. This non-planar structure can prevent the aggregation of π bonds and the formation of intermolecular exciplexes that lead to the reduction of the quantum efficiency of the device.

Method used

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  • Bisindenophenoxazine organic electroluminescence materials and application thereof
  • Bisindenophenoxazine organic electroluminescence materials and application thereof
  • Bisindenophenoxazine organic electroluminescence materials and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of compound C02

[0042]

[0043]

[0044] Preparation of Compound 1: In a 1L three-necked flask, add iodomethane (21.29g, 0.15mol), phenoxazine (18.32g, 0.1mol), xylene (450g), under nitrogen protection, add sodium tert-butoxide (19.20 g, 0.2mol), palladium acetate (0.246g, 1%mol), Xantphos (1.161g, 2%mol), heat up, keep the temperature at 120°C for 12h, cool down to 30°C, wash the reaction solution with water, separate the liquid, and anhydrous sulfuric acid Magnesium is dried, and desolvation, and gained brownish-yellow oily thing uses 50g sherwood oil to dissolve, carries out column chromatography (petroleum ether washing) by 25cm thick silica gel column, collects the passing column liquid that contains product, then desolvation, sherwood oil room temperature Slurry, filter with suction and dry to obtain compound 1, 12.88 g of light yellow solid, yield 65.3%, MS (m / s): 197.1.

[0045]Preparation of Compound 2: In a 1L three-neck ...

Embodiment 2

[0051] Embodiment 2: the preparation of compound C03

[0052]

[0053] Preparation of Compound 6: Using 4,4'-dicyanobenzophenone instead of benzophenone as a raw material, according to the method described in Example 1 (preparation of Compound 5), 4.64g (0.02mol) 4,4 '-Dicyanobenzophenone, the crude product of compound 6 was obtained, which was directly used in the next reaction without further purification.

[0054] Preparation of Compound C03: Using Compound 6 instead of Compound 5 as a raw material, according to the method described in Example 1 (preparation of Compound C01), 0.01mol (theoretical value) of Compound 6 was added to obtain Compound C03, a light yellow solid 4.70g, yield 60.4%.

[0055] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 55 h 31 N 5 O, theoretical value 777.25, test value 777.39. Elemental analysis (C 55 h 31 N 5 O), theoretical value C: 84.92, H: 4.02, N: 9.00, O: 2.06, measured value C: 84.89, H: 4...

Embodiment 3

[0056] Embodiment 3: the preparation of compound C05

[0057]

[0058] The preparation of compound 7: use bromoethane instead of methyl iodide as raw material, according to the method described in Example 1 (preparation of compound 1), put in 16.35g (0.15mol) bromoethane to obtain the refined product of compound 7, 9.53g of light yellow solid , yield 45.1%, MS (m / s): 211.1.

[0059] Preparation of Compound 8: Using Compound 7 instead of Compound 1 as a raw material, according to the method described in Example 1 (preparation of Compound 2), 21.13 g (0.1 mol) of Compound 7 was added to obtain the refined product of Compound 8, 16.64 g of a light yellow solid, and the yield was Rate 45.1%, MS (m / s): 368.9.

[0060] Preparation of Compound 9: Using Compound 8 instead of Compound 2 as a raw material, according to the method described in Example 1 (preparation of Compound 3), 36.91 g (0.1 mol) of Compound 8 was added to obtain the refined product of Compound 9, 37.24 g of light...

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PUM

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Abstract

The invention discloses bisindenophenoxazine organic electroluminescence materials and an application thereof, and belongs to the technical field of organic photoelectric materials. The bisindenophenoxazine organic electroluminescence materials have a molecular structure represented by formula 1 shown in the description; and in the formula 1, R1, R2, R3 and R4 are same, R1, R2, R3 and R4 are an alkyl group or an aromatic substituent group, and R5 is one of an alkyl group, an aromatic substituent group, a nitrogen-containing heterocyclic group or an oxygen-containing heterocyclic group. The invention also discloses an application of the bisindenophenoxazine organic electroluminescence materials. The materials have the characteristics of electron richness, non-planar structure, proper molecular mass, good film stability and suitable energy level. The materials can be applied to the organic electroluminescence field as a micro-molecular OLED device luminescence layer.

Description

technical field [0001] The invention relates to a class of bisindenophenoxazine organic electroluminescent materials and applications thereof, belonging to the technical field of organic photoelectric materials. Background technique [0002] Pope et al first discovered the electroluminescent properties of single crystal anthracene in 1965, which is the first electroluminescent phenomenon of organic compounds; while Tang et al. Formed organic light-emitting devices with separate functional layers that can deliver 1000 cd / cm even at 10 V or lower 2 High brightness above. After years of continuous development, organic electroluminescent devices can be used not only to manufacture new display products, but also to make new lighting products, which are expected to replace the existing liquid crystal display and fluorescent lighting. [0003] At present, products based on OLED display technology have been industrialized. Compared with liquid crystal display technology, OLED dis...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D265/34C07D413/04C07D413/10H01L51/54
CPCC09K11/06C07D265/34C07D413/04C07D413/10C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1088H10K85/615H10K85/654H10K85/6574H10K85/6572H10K85/657
Inventor 高树坤王正盛磊张鑫鑫胡葆华燕移寒
Owner VALIANT CO LTD
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